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#3038 Jul 25, 2013
The boss 500 tf funnycar engine is a all ford design. Look it up on realities I've posted many times. The part from the moose hemi won't bolt up to the Ford boss. The ford and force designed heads, are made different than the molars. Plus like I said, the boss 500 is a numbered part in ford catologs. Do you think if there making cash and fame from a mopar design, that mopar would just sit back and watch, and not sue them for fraud? Are ford and force would put that much time and cash into making the same designed engine? Don't listen to these mopar fans tell you lies, the nhra ford boss500 is all ford design.just like a ford motor had hemi style heads on a ford engine 4-5 years before molar ever had a Hein head on a engine. Here's to the all ford designed boss 500
#3039 Jul 26, 2013
Also, Courtney force ran 322mph in 1000ft track.fastest speed to 1000ft. In a test session. It's on YouTube. With boss 500 engine.faster than the 320mph record, but don't count as record. because it was in test session but on nhra track scoreboard. John force has the e.t and speed record for true 1/4th mile at 4.66st 333.75mph. Which his teammate Robert hight beat with a 4.63e.t @ 334mph in his ford designed boss 500 mustang but didn't have fast enough. Backup run to change record if you watch nhra, you know what I'm talking about.the reason it's 1000ft now is to slow them down
#3040 Jul 26, 2013
The all ford designed boss 500 has e.t and speed record in true 1/4th mile. And has ran faster speed in 1000ft pass with Courtney forces 322mph pass in test session is faster than mopars Jack beckman 320mph record pass. Plus ford set the fastest street legal record with twin turbo ford by @282 mph in Texas mile run. Plus has world record for a door driven reaches at 5.95e.t@ 260mph 1/4mile. Corey Arran or something. Look it up, I go by facts not forums or hearsay but real sites I can see. Go all ford designed boss 500 fastest engine in car made
Ottawa, Canada
#3041 Jul 26, 2013
There is only "ONE" engine in the NHRA Top Fuel classes, whether it be in a Funny Car or a Dragster.
It is called the NHRA Top Fuel Regulation Engine. This has been and continues to be mandated (read strictly enforced) by the NHRA.
The NHRA Top Fuel Regulation Engine platform (read base architecture) is the exclusive domain of the 1964, 426 Chrysler factory race HEMI®.
All of the engines running nitromethane fuel in the NHRA are closely scrutinized variants of the second generation Chrysler Hemi including John Force's Boss 500.
The Boss 500 conforms to the NHRA Top Fuel Regulation platform or it would not be allowed to compete. Force's engine was introduced during an NHRA engine development moratorium that has not been lifted. Moratorium means exactly that. No engine development.
To call that engine the Ford Boss 500 nitro engine is deliberately misleading. It does not matter how much Ford money has gone into the engine any more than it matters where it is produced.
By way of appearances it is the Boss 500, however it is not a Ford. It is a poorly disguised, cosmetically altered, customized Chrysler style Hemi.
There are no Ford parts or Ford engineering in it. Even the supposedly Ford main bearings available from the Ford racing catalogue aren't Ford. They're MAHLE/Clevite.
The same bearings developed for use in the nitro Hemi.
All of John Force's wins in Top Fuel regardless of the body style on the car were powered by Chrysler type Hemi engines and that continues to this day.
To call the Boss 500 a "Ford" engine is an insult to the Chrysler engineers responsible for an architecture that Ford can only envy.
The most recent publication that addresses this directly is the April 2013 edition of Mopar Action Magazine. The article by Paul Stenquist runs from pages 66 thru 71.
If a Mopar magazine seems too biased for your enlightenment then I recommend that you go to page 62 of the February 2013 Popular Hotrodding Magazine.
Read about the CHRYSLER SECOND-GEN HEMI.
Absolutely nothing in NHRA Top Fuel is Ford "powered" and hasn't been for over four decades. To believe otherwise is just poisonously and infectiously stupid.
To promote otherwise is fraud!
#3042 Jul 30, 2013
Ok, if you think so,lol. Just like you said you where getting mopar dodge to sue ford for false statements and fraud? Lol. It's the same engine, the heads, won't work on the boss engine from the mopar engine. The insides are different, the boss engine has part numbers in ford catalog, yet it's dodges design,lol.Yea, sure ford, dodge would let that happen,lol. You might fool some people, but it don't work with me. You say ford losing,force teams losing,nhra losing, magazines talking about its losing. For what reason would that help them? That's like saying Henry Ford quildcycle was copied by all car makers in usa
#3043 Jul 30, 2013
Envy,lol. Funny you know ford engine had first Hemi style head on car,5 years before molar ever had Hein heads on there car engines. So who copied who, talking about fraud. Henry Ford had first gasolined car style in USA, called quildcycle 1896, so every car company to make one , copied Ford's design= fact. So really mopar copycated Henry Ford car design. He made first gas powered car in usa, they can only be one first maker of anything. So mopar is the one commiting fraud.by copying car design,and copying a hemi style head off a ford engine. Because ford motor had hemi head before mopar. 427 cammer ford engine had more horsepower than a mopar Hein engine. 657hp from factory
#3044 Jul 30, 2013
Like I said. Ford, force made new engine, with new insides,New heads and is all ford designed engine. Think what you want, but the fact is, boss 500 is all ford designed, and has run faster speed in 1/4 mile,and 1000ft.than a molar hemi. Mopar only dreams of running faster. All ford powered boss500 ford engine, eating mopars
Ottawa, Canada
#3045 Jul 30, 2013
The set of parameters in which the BOSS 500 is based is to follow the pattern of the generation 2 Chrysler HEMI® as mandated by the NHRA.
So what makes it a Chrysler pattern?
Sanctioned by Chrysler, former Chrysler engineer Bob Tarozzi amended the Chrysler factory engineers 1964, 426 race HEMI® blueprint to allow for the properties of aluminum. Engine builder Keith Black worked from that blueprint to produce the Chrysler top fuel race HEMI®. Blacks motor wore a MOPAR® part number. The NHRA adopted that engine as their top fuel regulation platform. All engines conforming to that platform are Chrysler variants. This becomes easy to understand when you know that pattern is a synonym for design.
How is the BOSS 500 a Chrysler HEMI® design?
The Chrysler HEMI® variant TFX and the BOSS 500 share the same bore spacing, cylinder bank offset/vee inclination, camshaft centerline, block deck height, main bearing and camshaft bore diameters, lifter bore spacing, head stud positioning; the exact same pattern of 4 main cap bolts (2 vertical, 2 horizontal), with studs of the same material and dimension, thread pattern and depth of engagement.
The cylinder bore diameter is the same between the BOSS 500 and the Chrysler HEMI® at 4.1875(4.19). The BOSS has the same diameter dry cylinder liners as the HEMI®, same depth, retained by a flange at the top, the same Hussy Copper head gaskets, the same 13 head studs, 5 taller toward the inside, the other 8 on the outside in the same pattern.
The camshaft and crankshaft will interchange. The TFX HEMI® variant ran a 3 main bearing for years before it was used also in the BOSS 500.
According to Dean Antonelli of John Force Racing the 3 bearing is the Clevite Nitro V series bearing developed for the top fuel HEMI®. The crankshaft is from Sonny Bryant and Winberg and the cam is from Competition Cams (9310 billet).
The intake valve is 35 degrees from vertical, exhaust valve 21 degrees, with a 56 degree included angle. Bore spacing on the BOSS 500 and the Chrysler HEMI® is 4.80.
The NHRA imposed a moratorium on engine development on November 11, 2003. Engine development moratorium means exactly that, no engine development. Four years into that moratorium which still stands, the BOSS 500 first ran in Las Vegas on October 18, 2007.
Ottawa, Canada
#3046 Jul 30, 2013
In 2006, Computer Assisted Design (CAD) specialist James Gregg drew the BOSS 500 based on the parameters of the NHRA regulation engine.
In other words he drew an existing architecture so that it could be studied for alterations.
To suggest that this was a clean sheet approach does not make it a clean sheet design. That drawing was functionally-based on the existing and proven design of the Chrysler HEMI®.
Working to make changes within the confines of an existing architecture is nothing more than customizing, and identifying the finished product defaults to the base (read parent) architecture.
The BOSS 500 is a Chrysler HEMI® variant. It is not a clean sheet engine, never was.
The TFX top fuel engine was approved by the NHRA to run a 3 main bearing. Other than that concession it is still a Chrysler HEMI® variant. After having run that bearing for a few years in the TFX, JFR decided that since the 385 series Ford 429/460 use a 3 main bearing they could give the engine some other identity by way of a Ford part number for the bearing, never mind that the bearing is produced by Clevite and was developed for the top fuel HEMI®.
As the architecture signifies the designation of the bearings, then the 3 Clevites that JFR use in the BOSS 500 are actually Chrysler bearings as they reside in a Chrysler style architecture.
How did JFR "transmogrify" the HEMI®?
They modified the main cap and put metal in the area where it resides. They put metal into the pockets in the block above the pan rail. They moved the intake lifter a full 100 thou because nothing in the rules said they couldnt. When this put the pushrod right up against its guide through the cylinder head they (John Medlen) explained that this is to prevent deflection of the pushrod, never mind that no such consideration is given to the exhaust side. Holes in the block pan rail were relocated to provide for mounting a Ford oil pan. Apparently this is to promote better sealing, whilst the unmolested HEMI® has no sealing problem in this area. The block is externally ribbed to suggest an all-new-engine never mind that all of the engine internals are dimensionally the same HEMI® pieces and will interchange.
There are a select few external differences to distinguish the BOSS 500 in an attempt to keep it exclusive unto itself, like the rocker covers for example, and the normal cut-out in the flange for the starter has been eliminated for a more symmetrical bolt pattern to attach the block to the clutch bellhousing, but the parent architecture is indelible.
In spite of the pretty blue paint the BOSS 500 is a Mopar® style HEMI® through and through.
#3047 Jul 30, 2013
Dodge hands down they were the first to come out with a fourwheel drive and they last forever me and my buddy tried to blow up an old 225 slant six we did everything short of drain the oil the old power wagons are beasts they will out pull anything just about Chevys 1 tons are pretty damn good trucks to if you have a 292 straight six and a 4 speed bulldog with 1 ton axles it will last forever love the old 292's so Chevy and dodge hands down ford just dosnt have much goin for them
#3048 Jul 30, 2013
I'm not saying your wrong on ford and there engines but cummins isn't the fastest it's a straight six a duramax will have not hp then a cummins almost always but the cummins is gonna have 10 times more low end torque them ford or Chevy and the tranny issues arnt realy takin care of it or not its faulty on dodges part the sensors go out but this is only for the auto trannys if you get a 5 speed or 6 speed your fine
#3049 Jul 31, 2013
The parts will not innerchange, the heads are designed different to. Plus like I said, a ford engine had Hemi style heads 4-5 before dodge mopar put hemi heads on any of the cars. So mopar copycated a ford design. Boss 500 is all ford design. All the engines are 500 cubic inches plus.mopars and Ford's boss engines. They changed the insides you named, made new designed heads.so what's mopar about it? All the engines have aftermarket upgraded parts, better cranks, thicker stronger blocks. On mopar and ford engines, ford changed parts on inside and made new designed heads, so what's mopar about it? Plus hemi heads where on a ford engine before mopar ever had them. So mopar is really copying a ford engine. Nice try, the all ford designed boss 500 engine
#3050 Jul 31, 2013
Plus ford 427 cammer engine was faster than a mopar hemi, the underrated mopar hemi made over 500hp.same as a regular 427 sideoiler ford engine and the boss 429 engine.But the 427 ford cammer engines made 657hp from factory was highest hp engine non supercharged or turbocharged from any of big 3. Plus you said it best when you said Keith black changed the block.which added stronger thicker metal, stronger aftermarket crank,bigger higher lift aftermarket cam.punched block to 500 cubic inches, so what's mopar about engine? Ford went in and changed spacers, made new heads which will not bolt to a mopar engine or work on it. So yes it is a all ford designed engine. In fact I read where ford and force wanted to build a whole new block and all,nhra would"nt let them. The engines now are as much ford as they are mopar. Both having thicker punch to 500 inch stronger metal blocks. Ford changed the parts you named and made the new better head, ford design, New and old. So yes the boss 500 is all ford designed engine.
Ottawa, Canada
#3051 Jul 31, 2013
ALL of the BOSS 500 specific data in post 3045 originates IN HARD COPY from JOHN MEDLEN!
Absolutely everything that was done to the BOSS 500 was done under the auspices of John Medlen.
All of John Medlen's oral utterings through interview concerning the BOSS 500 are retrievable in hard copy and I have done exactly that.
Even John Medlen cannot deny or ARGUE any of the content of post 3045 for the simple reason
that John Medlen dictated all of that information himself while it was physically recorded; in other
words, it was all written down.
The Fraud/Farce Boss 500 is a poorly disguised, cosmetically altered, customized Chrysler style HEMI® that has no Ford parts or Ford engineering in it. There is no Ford power in NHRA Top Fuel and there hasn't been for over forty years.
#3052 Jul 31, 2013
The only fraud is mopar"s copycating ford to begin with with ford engine having hemi heads on a engine 4-5 years before mopar ever had them on there engines. The boss 500 is a ford engine. Parts changed on inside that they added, that were parts numbers in ford catalog that you even posted on. All new ford designed ford hemi heads that won't bolt up, or match up with the mopar engines. The only thing mopar has to do with there engines are the heads. The block, crank,rods, pistons, cams are aftermarket. The blocks are made 500 cubic inches made by machine to start with.Ford went through made new bearings,oiling system, and more and new designed heads. Which won't match up or bolt to a mopar hemi engine. So yes boss500engine is all. Ford designed engine
Innisfil, Canada
#3053 Jul 31, 2013
Paradigm. There's no point in knocking yourself out trying to convince mustang of anything. He's made up his mind that he's right and nothing that you ever say will change that.
I'm quite capable of making up my own mind about this and from what you've said in your last few posts I am convinced that John Force's fueler engine is a Chrysler copy.
I have had my own suspicions about this for a while. I will forward what you have written to others whom I know are open to the truth and connected to do something about it. "Squeaky wheel gets the grease"!
Thankyou for a most revealing look at the Boss 500 and more importantly the blatent skullduggery with all concerned. Fraud you say? Yes it is.
#3054 Jul 31, 2013
Wow, make new screenname and agree with yourself,lol. I pointed out the truth.the guy named Ellis was going to his buddy over a year ago, that worked at Chrysler to sue force and ford. Never heard anything about it again. Can't sue someone for making changes to a engine with ford parts. Funny you yell fraud, when ford engines had hemi combustion chambers in head before mopar did. My last post pretty much explained the whole deal.I proved I'm right, by sites I posted pages ago.you still haven't explain why all the drag racing sites and other sites are lieing as you say? Why they would post lies to hurt them, to help ford out?how does lieing help there cause? When they change parts on inside you can find in ford catalog,make new heads that won't work are even bolt to a mopar hemi engine. How you get its a mopar? That's like a nascar engine, they say pistons, rods, crank, and cams will work in all three blocks now.same as funnycar& top fuel engines. Nothing is mopar on eengines. Keith black machined thicker,stronger 500+ cubic inch blocks.bigger lift aftermarket cams, stronger bigger cranks aftermarket, aftermarket pistons, aftermarket rods. Nothing mopar mopar about it.Ford and team force changed bearings, oiling system,and so on.made brand new designed heads from ford and force blueprints,that I repeat,that won't work,match up, or bolt on mopar dodges funnycar engine. So yes it is a all new ford designed engine
Ottawa, Canada
#3055 Aug 1, 2013
The stupid, mouthy "thing" thinks I drove 430 miles to make a "new screenname" and post to "it".
Oxygen wasting mud-monkey. Imbecile!!
#3056 Aug 1, 2013
Lol , mad bro? Truth hurts huh
#3057 Aug 1, 2013
Check out this that I wrote and posted.
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|Publication number
|Publication type
|Publication date
|Jul 12, 1960
|Filing date
|Jun 10, 1954
|Priority date
|Jun 10, 1954
|Publication number
|De Groote Melvin, Pettingil Owen H
|Original Assignee
|Petrolite Corp
|Export Citation
|BiBTeX, EndNote, RefMan
|Patent Citations (7), Referenced by (15), Classifications (8)
|External Links: USPTO, USPTO Assignment, Espacenet
y 12, 1 M. DE GROOTE ETAI. 2,944,982
PROCESS FOR BREAKING PETROLEUM EMULSIONS EMPLOYING CERTAIN OXYALKYLATED ACYCLIC DIGLYCEROLS Filed June 10, 1954 BUTYLENE OXIDE I00% ACYCLIC DIGLYCEROL ETHYIIENl-E !00 OXIDE I00 4 INVENTORS el t t Patsfl PROCESS FOR BREAKING PETROLEUIVI EMUL- SIONS EMPLOYING CERTAIN OXYALKYLATED ACYCLIC DIGLYCEROLS Melvin Decroote, University City, and Owen H. Pet-' tingill, Kirkwood, Mo., ,assignors to Petrolite Corporation, Wilmington, DeL, a corporation of Delaware Filed June 10, 19s4,ser.No. 435,663
20 Claims crass-s31 invention relatesto processes or procedures particularly adapted for preventing, breaking or resolving emulsions of thewater-in-oil type, and particularly petroleum. emulsions. x o r Our invention provides an economical and .rapid processfor resolving cpetroleum femulsions of the water-in-t oiltype "that are commonly referred. to as cut on," roily oil, emulsified oil, etc., and which comprise fine droplets of naturally-occurring waters or brines dispersed in a more or less permanent state throughout the oil which constitutes the continuous phase of theemulsion.
It also provides'an economical and rapid process for' separating emulsions which have been prepared under controlled conditions from mrl'deral oil, such as'cr' ude oil and relatively soft waters or weak brines. Controlled glycerol. The cogeneric mixture is derived exclusively from acyclic diglycerol, ethylene oxide andbutylene oxide in such weight proportions so the average composition of said cogeneric mixture statedin terms of in itial reactants lies approximately within the 5 -si,dcd figure of the accompanying drawing in which the minimum acyclic diglycerol content is at least 1.5% and which 5-sidedfigur'e is identified by thefact that its area lies within. the straight lines connecting A, B, C, D, and H.
All references to diglycerol, unless the text indicates con-,-
trariwise, means acyclic diglycelrol having 4 hydroxyl radicals.
We have, found that when (ii glycerol is v combinedwith butyleneoxide and ethylene oxide incertain proportions and particularly when the butylene oxide is employed first, followed by use of ethylene oxide and morefespecially if the butylene oxide employed is one of the straightchain isomers or a mixture of the two audit the composition falls with-- in thelimits indicated by the S-sided figure on the hereto attached triangular chart, said derivatives are of unusual eifectiveness for a number of purposes particularly when surface activity, is a factor,
tion of petroleum emulsions of the water-in-oil type.
been treated with about 11 to.39 parts of butylene oxide, by weight, and then reacted with 27 to 58.5 parts of ethylene oxide. I w V V In another series 10 parts of diglycerol have been reacted with 5 parts by weight of butylene oxide and parts by weight of ethyene oxide. In anotherseries 1.5 parts by weight of diglycerol have been reacted with 13.5 parts-by Weight of butylene oxide and 85 parts by weight of ethylene oxide. Similarly, in another series the following combinations have been 'used: 1.5 parts of diglycerol combined with 58.5'partsby weight of butylene oxide and 40 parts by weight of ethylene oxide; 20 parts by weight of diglycerol, reactedwith 40 parts by weight of butylene' oxide and then with 40 partsby weight of ethylene oxide! In another series 20 parts by weightof .diglycerol were reacted with 10 parts by weight of butylene oxide and then 70 parts byweight of ethylene oxide. f
it is of interest ,to note in some instances asflittle" as 1. S parts of diglycerol may be combined with 9815 parts of-the two oxides to produce very valuable deriv-.j
' We have alsofound that where part of the butylene oxide is replaced by propyleneoxide, i.e., where' acorn bination of diglycerol, butyle'ne oxide, .propylenei'oxide and ethylene oxide are used, efiectiveand valuable sur- This, "however,
least the test set forth in US. PatentfNof 2,499,368,
dated March 7, 1950, to De Groote and Keiser. V In said patent such test for emulsification using a water-insola uble solvent, generally xylene, is described as an index ofsurface activity. on p a The above mentioned test, i.e., a conventional emulsification test, simply means that the preferred product. for deniulsification is soluble in a solvent having hydro phobe properties or in an oxygenated water insoluble or even a fraction of a water-soluble hydrocarbon solvent or even a \fraction of a water-soluble hydrocarbon .solvent and that when shaken with waterthe product may remainxin the nonaqueous solvent or, 'for that matter it may pass into the aqueous solvent. .In other words, al-) though it is xylene soluble, for'example, .it' may also be water soluble to an equal'or greater degree.
For will be divided into three parts:
Part 1 is concerned with the oxyalkylation of diglycerol in general; a 7
Part 2 is concerned with the oxyalkylation of diglycerol using two difierent oxides, i.e., butylene oxide and ethylene oxide so as to produce derivatives falling within certain composition limitations hereinafter noted in detail. For convenience, Part 2 is divided into two sections, Section A is concerned with oxybutylation and oxyethylation broadly, and Section Bis concerned with the particular compositions corresponding to the herein specified compositions and illustrate such combinations;.-
Part 3 is concerned "with the resolution of petroleum Pa e t either directly or indirectly. One example-is the use of such derivatives in the 'r esolupurpose of convenience what issaid .hereinafte emulsions of the water-in-oil type by means of the previously described chemical compounds.
PART 1 At the present time there is available butylene oxide which includes isomeric mixtures, for instance, one manufacturer has previously supplied a mixed butylene oxide which is in essence a mixture of l-butene oxide, 2-butene oxide isomers and approximately isobutylene oxide. Another manufacturer has supplied an oxide which is roughly a fifty-fifty mixture of the cisand trans-isomers of 2-butene oxide.
There is also available a butylene oxide which is characterized as straight chain isomers being a mixture of the 1,2 and the 2,3 isomers and substantially free from the isobutylene oxide.
This latter product appears to consist of 80% of the 1,2 isomer and of the mixed 2,3 cisand 2,3 transisomer. We have obtained the best results by using an oxide that is roughly 80% or more of the 1,2 isomer and with either none, or just a few percent if any, of the isobutylene oxide, the difference being either form of the 2,3 or a mixture of the two forms.
Our preference is to use an oxide substantially free from the isobutylene oxide, or at least having minimum amounts of isobutylene oxide present.
Since the varying solubility of different butanols is well known, it is unnecessary to comment on the effect that the varying structure has on solubility of derivatives obtained by butylene oxide. Purely by way of example, the applicants have tested the solubility of the first two available butylene oxides and noted in one instance the butylene oxide would dissolve to the extent of 23 grams in 100 grams of water, whereas the other butylene oxide would only dissolve to the extent of 6 grams in 100 grams of water. These tests were made at 25 C.
As to further reference in regard to the isomeric butylene oxides see Chemistry of Carbon Compounds, volume 1, part A, Aliphatic Compounds," edited by E. H. Rod-d, Elsevier Publishing Company, New York, 1951, page 671.
As to the dilference in certain proportions of the cisand trans-form of straight chain isomers 2,3-ep0xybutane see page 341 of A Manual of Organic Chemistry, volume 1, G. Malcolm Dyson, Longmans, Green and Company, New York, 1950.
Reference to butylene oxide herein of course is to the compound or compounds having the oxirane ring and thus excludes 1,4-butylene oxide (tetrahydrofurane) or a trimethylene ring compound.
When reference is made to the oxides, for instance, ethylene oxide and butylene oxide, one can use the corresponding carbonates. Ethylene carbonate is available commercially. Butylene carbonate, or the carbonate corresponding to a particular oxide, is not avilable commercially but can be prepared by the usual methods in the laboratory. For this reason further reference to the.
alkylene carbonates will be ignored although it is, understood when oxyethylation takes place by means of ethylene carbonate one could, of course, use butylene carbonate for oxybutylation.
In the present invention we have found that outstanding products are obtained by the use of certain preferred butylene oxides, i.e., those entirely free or substantially free (usually 1% or less) and composed of approximately 85% or more of the 1,2 isomer with the remainder, if any, being the 2,3 isomer.
In the preparation of the outstanding compounds we have studiously avoided the presence of the isobutylene oxide as far as practical. When any significant amount of isobutylene oxide happens to be present, the results are not as satisfactory regardless of the point when the butylene oxide is introduced. One explanation may be the following. The initial oxybutylation which may be simplified by reference to a monohydric alcohol, produces a a tertiary alcohol. Thus the oxybutylation in the presence of an alkaline catalyst may be shown thus:
Further oxyalkylation becomes difficult when a tertiary alcohol is involved although the literature records successful oxyalkylation of tertiary alcohols. This does not necessarily apply when oxyalkylation takes place in the presence of an acidic catalyst, for instance, a metallic chloride such as ferric chloride, stannic chloride, aluminum chloride, etc.
The difliculty is that there is some tendency on the part of digylcerol to convert to a higher polyglycerol such as the tetraglycerol or form acyclic compounds in which hydroxyl groups are lost. If one proceeds under such circumstances one would be oxyalkylating not only acylic diglycerol but possibly cyclic triglycerol to say nothing of higher polyglycerols such as tetraglycerols (cyclic or non-cyclic) and water. We have tried procedures using an alkaline catalyst and diglycerol employing 4 to 6 moles of isobutylene oxide per mole of diglycerol. Afterwards an amount of acid was added equal to the amount of caustic employed as a catalyst and the reaction mass dried and then stannic chloride added. Under such circumstances results suggest more satisfactory oxybutylation as such although the procedure becomes cumbersome, uneconomical, and perhaps even impractical.
This, however, seems to be only a partial explanation. Another explanation may rest with the fact that isobutylene oxide may show a tendency to revert back to isobutylene and oxygen and this oxygen may tend to oxidize the terminal hydroxyl radicals. This possibility is purely a matter of speculation, but may account for the reason we obtain much better results using a butylene oxide as specified. In regard to this reaction, i.e., possible conversion of an alkylene oxide back to the olefine and nascent oxygen, see Tall Oil Studies II, Decolorization of Polyethenoxy Tallates With Ozone and Hydrogen Peroxide, J. V. Karabinos et al.,-I. Am. Oil Chem. Soc. 31, 71 (1954).
In order to illustrate why the herein contemplated compounds or said products are cogeneric mixtures and not single chemical compounds, and why they must be described in terms of manufacture, and molal ratio or percentage ratio of reactants, reference is made to a monohydric alcohol. Diglycerol, of course, is a polyhydric alcohol having 4 hydroxyls. However, one need only consider what happens when a monohydric alcohol is subjected to oxyalkylation.
If one selects any hydroxylated compound and subjects such compound to: oxyalkylation, such as oxyethylation, it' becomes obvious that one is really producing a polymer of the alkylene oxide except for the terminal group. Thisisfparticularly true where the amount of oxide added is comparatively large, for instance, 10, 20,
30, 40, or 50 units. If such a compound is subjected to oxyethylation so as to introduce units of ethylene oxide, it is well known that one does not obtain a single constituent which, for sake of convenience, may be indicated a RO( C H O) I-I. Instead, one obtains a cogeneric mixture of closely relates homologues in which the formula may be shown as the following:
wherein n, as far as the statistical average goes, is 30, but the individual members present in significant amount may vary from instances where n has a value of 25 and 75 perhaps less, to a point where 11 may represent or alkylation.
aeiisi more; mixture is', as stated, a cogeneric closely,
related series of touchin'ghomologous compounds, C9 17 siderable investigation has been made in regar to. t e;
distribution curves for'linear'po lymers Attention is directed, to the article entitled Fundamental Principlesof Condensation Polymerization, by'Paul I. Flory, which appeared in Chemical Reviews, yolume 39, No. 1, page 137. r
Unfortunately, as has fbcen'rtrpointed out by Flory and other investigatorgthereds no s tisit'actory method based a l thsr x i ent r me a en. q a in frt vqrt cn condensation products ot thekind described." that from the practicall standpoint, re, th A describe how to make the p'rodi1ct under consideration and how to repeat such production time after time with} out difliculty it is necessary to resort to some other mthodof description. 'f '1 What has been said in regard 'to a monohydric conipoundof course is multiplied many 'timesin the case of a tetrahydric compound such as digtlycerol. This is particularly true even in regard to ethyleneoxide alone but becomes even more complicated when butylene oxide is used in light of what has been said previously in regard to the isomers of butylene oxide.
'P nT 2 Section A V The oxyalkylation of glycerol or polyglycerol, including acyclic diglycerol, has been described in the literature.
The procedure is the same as the oxyalkylationof ethyl ene -glycol, propylene glycol; butylene glycol or the like.
. v h a i u mwb r of touching homologous series which appearincog eric;
parts by weight of butylene oxide toonepart of diglycerol.v The xylenepresent represented approximately .6 of one part by weight.
i l i Example 2a Th r a lm w st ans fl m t a sera it v (s aci ygfi e s). iYY hg tnadd a o lvent.
or anyfmore xylene the procedure'was repeated so as to.
add another 1500 grams of butylene oxide under substan'{ tially the same operating condi tiqns but requiring about 2% hoursfor the addition. "At the end of this step ;the rati' representedapproximately 6 to 1 (ratio butylene QXidfiJQ ig y flm lt t v Example 3a In a third s tep in'stead of-adding 1500 grams of'but ylene oxide, 1625 grams were added. Thereaction slowed up and required approximately hours, using the same operating temperatures "and pressures. The ratio at the Instead, no particular problem is involved because the product is a liquid at 'oxyalkylation. temperatures, for-instance, 120. C.-to 130 C. J p 1 a 7 Purely as a matter of convenience it is not unusual to add a solvent,such as xylene, which-only'forms a suspension or emulsion with diglycerol. when agitationis employed. ,However, as soon as the product becomes oxybutylated or oxypropylated to anydegree the reaction massis xylene-soluble andithus thereis some benefit by the reduction in viscosity of the reaction mass. We have employed xylene although it isv not necessary and may be omitted if desired. It is purely a convenience in oxy- Itjis not 'believed any examples are necessary to illustrate such well known procedure butfor purpose of illustration the following are included:
I I Exampl'Ja 5 p c The reaction vessel employed was, a stainless steel autoclave with the usual devices for, heating, heat control, stirrer, inlet, outlet, etc., which is conventional in this type of apparatus. The capacity was approximately 4 liters. I The stirrer operated at a speedof approximately 250 'r.-p.m. There were charged'irito the autoclave 500' end of the third step was 925 parts by weight of butylene oxide per'weight of diglycerol.
Example 4a At the end of this step the autoclave was'opened and an additional 5 grams "of sodium methylate' added, the autoclave flushed out as before, and the fourth and final oxyalkylation completed, using 1625 grams of butylene oxide, and the oxyalkylation was complete within 3 hours using the same temperature range and pressure as previously. At the end of the reaction the product represented approximately 12.5 parts of butylene oxide by weight to one part of diglycerol.
All the examples, except the first step, were substantially water-insoluble and xylene-soluble.
MAs'hasbeen pointed out previously these oxybutylated diglycerols were subjectedto oxyethylation in the same manner. described in respect to the oxybutylated digly- I cerol; Indeed, the procedure is comparatively simple for the. reason that one isWOrking with a liquid and also that ethylene oxide is more reactive than butylene oxide. As
a result,.using the same amount of catalyst one can oxyethylate more rapidly than usually at a lower pressure.
There is no substantial difference as far as operating procedure goes Whether one is oxyethylated digly'cerol or oxybutylated diglycerol.
Thesame procedure using a slurry of finely powdered diglycerol in xylene was employed in connection with W ethylene oxide and the same mixture on a percentage basis was obtained as in the above examples where butylene oxide'and. diglycerol were used.
The same procedures have been employed using other butyleneoxides including mixtures having considerable -isobutylene oxide and mixtures of the straight chain -isomers with greater or lesser amounts of the 2,3 isomer.
grams'of diglycerol, 300 grams of xylene,and .15 grams a of sodium niethylate. The autoclave was sealed-sweptwith nitrogen gas and stirring started immediately and; e temperature was allowedto rise to approximately .14? C. At this particulartime the addir; tionpf butylene oxide was started; The butylene-oxide. employed-was .amixture of the straight chain isomersub stantiallytreeijfrom isobutyleneioxide It was addedcom,
l tinuously at such speed that it was absorbed by the reaction 'as added. The amount added in this operation was heat applied; 4
1500 grams; The time required to add the butylene oxide and then the other.
was 1% hours; During this period the temperatureuwas' l maintained at 130 to 145 C., using cooling water applying heatif required. The maximum pressure during the. reaction 47 pounds per squareinch. Ignoring the X e e dsdi mm h ste n .s n r e diglycw erol for convenience, the resultant product represents 3 through the inner coils when necessary and otherwise.
Where reference has been made in previous examples to the straight chamisomer, the product used fwas one which wasv roughly 85% or more of the 1,2'isomer andapproximately' 15%-of the 2,3-cisandqthe *2,-3-trans- 1 isomerwith substantially none or not over- 1%, of'the,
as a matter of fact, we have used such methods in connection with molten sorbitol. I i: H W If desired, one may and part of one oxide and all ot:
"'5 the other and then return to the use of the firstoxide,
for instance; or one may use the procedure as previously,
' be added in portions so that firstzone oxide is added, then the other, then the first oxide is added again, and then the s'econd oxide. We have 'found no advantage in so doing. Indeed, our preference has been to add all the butylene oxide first and then the required amount'of ethylene oxide. t
As "pointed out previously,diglycerolcan be oxyethylated in the same way 'it is oxybutylated, i.e., by preparing a slurry in xylene orin'a siriiilar'solventfand using a suitable alkaline catalyst such as caustic soda, sodium methylate, or the like, and then adding the ethylene oxide. The changes previously mentioned are of difference in degree only. In other words, oxyethylation will take place at a lower temperature, for instance, a top temperature of probably 130 to 135 C. instead of 145 to 150 C. The same weight of ethylene oxide could be added in 75% to 85% of the time required for. butylene oxide. The pressure during the reaction, instead of being 35 to 45 pounds as in the case of butylene oxide, is apt to be to pounds and at times a little higher. Otherwise, there is no difference.
trace of moisture. Our preference is to prepare the slurry with an excess of xylene and distill 01f a part of the out the "mass nitrogen. Even so,' th'ere may be a fewtenths of a percentcfmoistureremain although at times ex'aifriination indicates at the 'rrio's't it is merely a trace. 5 I
' PART 2 Secti0'n'B In light of'what has been said "previously, particularly Section A, it is obvious that hardly any directions are .to produce the compounds herein specified. However, referring to the composition of the initial reactants; based on the S-sided figure in the attached drawing, it will be noted we have calculated the percentage of the three initial reactants for the points A, B, C, D,
E, F, G, H, I and I which appear on the boundary of. the S-sided figure and also determine t-he five sub-divided parts of theS-Sided figure, two parts being triangles and i the others being two parallelograms and one trapezoid.-
Likewise, we have calculated the composition for a nurn berof examples within the area of the-graph andcorresponding to points 1 to 18, inclusive. Note these data are included in Table I, immediately following:v
TABLE I Tertiary Mixture, Binary Intermediate Mixtures,
Percent Basis Percent Basis Points on Boundary of Area Acycllc Butyl- Ethyl- Acyclic Butyl- Acyclic Ethyl- Dlene ene Diene Diene glycerol Oxide Oxide glycerol Oxide glycerol 7 Oxide 10.0 5. 0 85.0 66. 6 33. 4 10. 5 89. 5 1. 5 13. 5 85.0 10.0 90. 0 1. 7 98. 3 1. 5 58. 5 40.0 2. 5 97. 5 3.6 96.4 Y 20.0 40.0 40. 0 38. 4 66. 6 33. 4 66. 6 1. 5 40. 0 58. 5 3. 6 96. 4 2. 5 97. 5 1. 5 30.0 68. 5 4t 75 95. 2.14 97. 86 1. 5 20.0 78. 5 7.0 93. 0 1. 87 98.13 20.0 10.0 70.0 66. 6 33. 4 22. 2 77. 8 20.0 20.0 60.0 50.0 50.0 25.0 75.0 20.0 30.0 50.0 40.0 60.0 28.6 71. 4 5.0 52. 5 42. 5 8. 68 91. 32 10.5 89. 5 8.0 44.0 48. 0 15. 4 84. 5 l4. 3 85. 7 1. 5 54. 5 44. 0 2. 68 97.32 3.3 96. 7 18.0 36. 5 45. 5 33. 0 67.0 28. 3 71. 7 15.0 33. 5 51. 5 31.0 69. 0 22. 6 77.4 7. 5 36. 5 56.0 17. 1 82. 9 11. 8 88. 2 1. 5 34. 5 64. 0 4.16 95. 84 2. 3 97.7 17. 0 28.0 55.0 37. 7 62. 3 23. 6 76. 4 7.0 26.0 67.0 21. 2 78. 8 9. 5 90. 5 13. 5 22. 5 64. 0 37. 5 62. 5 17. 4 82.6 15.5 19.0 65. 5 44. 8 55. 2 19.2 80. 8
Also, if desired, the use of ethylene carbonate is a very convenient way of oxyethylating diglycerol. In fact, it can be oxyethylatedwithout the use of pressure. Such procedure, and particularly melting the carbonatefirst and adding the powdered diglycerol slowly permits the production of a' reaction mass which is a 'liquid'or which melts readily at comparatively low temperatures to yield a liquid. Such reaction should be conducted in such a way that there is no residual ethylene carbonate when the mass is transferred to an autoclave.
One can oxyalkylate using an acid catalyst or an alkaline catalyst or at least in part, without the use of any catalyst although such procedure is extremely slow and uneconomical. In other words, any one of the conventionalcatalysts used in oxyalkylation may be employed. It is our preference, however, to'use an alkaline catalyst such as sodium methylate, caustic soda, orthe like.
Actually; vfiliely Pbwdfe'd dig y may contain a ouspoints onthe boundary and within the 5-sided figure propriate number of pounds of oxide; for instance, in
regard to point A all that would be necessary would be to mix 5 pounds of butylene oxide with pounds of ethylene oxide and use the mixture to oxyalkylate 10 pounds of diglycerol.
Similarly, in Example B, one need only mix 13.5
0 pounds of butylene oxide with 85 pounds of ethylene oxide and use the mixture to oxyalkylate 1.5 pounds of diglycerol in the manner previously indicated.
Note the fifth and sixth columns represent binary intermediate mixtures. For instance, in regard to the vari- Thus it is apparent that one ene.
flied, we have calculated'the initial mixture using glycerol and butylene oxide in the first case, "and using diglycerol and ethylene oxide in the second case, which would be employed for subsequent oxyal-kylation to give the particular composition required. Note that a binary. intermediate for the preparation of point A can be pre-. paredany suitable manner involving 66.6% of diglyc-i erol and 33.4% of butylene oxide. Thus, for example one could use 66.6-pounds of diglycerol and 33.4pounds of butylene oxide, or on a larger scale one could use 666'pounds of diglycerol and 334 pounds of butylene oxide. i "i 1 Referring now to the tertiary mixture table, it is ap-; parent that for point A diglycerol and butylene oxide together represent 15 and ethylene oxide 85%. Therefore, one could employ ,15 pounds of the binary mixture and react it with 85pounds ofethylene oxide. I
Similarly, in regard to the fifth and sixthcolumns for point B, the initial mixture involved diglycerol and butylenef'oxide, representing 10% of diglycerol, and 90% of butyleneoxide. i If desired; 10 pounds of diglycerol could be? reacted with 90 pounds of butylene oxide. Such mixture needionly be reacted with ethylene oxide by re- 1 acting ,15 pounds of the mixture with 85 pounds of ethyl- This is obvious from the data in regardto the tertiarymixtures. a 1 L1,. 1
:1 Referrihg now to columns 7and 8, it is obyious one could readily produce an oxyethylated diglycerol and then subject it toreaction with butylene oxide; --Using this procedure inregard to A, it is obvious that the mixture represents 10.5% of diglycerol and 89.5% of ethyleneoXi deiL-This product could be obtained from a binary mixture of 105 pounds of' diglycerol and 895 pounds of ethylene oxide. I
:uerer ng-now to the tertiary mixture table, {it is-ob- V vious-that 95 pounds of'such mixture could'be reacted with 5 pounds of butylene oxide to give point A. :Simi-'' larly, in regard 'to point'B theoxye thylated diglycerol represents 1.7% of diglycerol and 98.3 ethylene oxide. The mixture so obtained by referring to the tertiary mix ture tablewouldbe-reactedwith butylene oxide in.the proportion of 86.5 pounds of the mixture and 13.5 pounds of butylene oxidenj 7f ,Aspreviously pointed out, the oxyalkylationof diglyc erol has" been described inthe literature and is de-l TABLE II Composition Composition Composition where Butylwhere' Ethyl- Composltion Corresponding where, Oxides ene Oxide -ene Oxide' to Following Point are Mixed Used First Used First Prior to Oxy- Followed by Followed by alkylation Ethylene Butylene Oxide Oxide A Aa Ab Ac B Ba Bb Be Ca Cb Cc D Da Db Dc E- Ea Eb Ec F Fa Fb Fa G Ga Gb Gc H Ha Hb Hc I- Ia Ib I0 I. lo J1: J0 1a 1b 1c 2- 2a 2b 2c 3. 3a 3b 3c 4a 4b 4c 5 5a 5b 5c 6a 6b 6c 7a 7b 7c 8a 8b 86 9a 9b 9c 10a 10b 100 11a 11b 11c 12a 12b 120 13a 13b 131: 14a 14b 140 15a 15b 150 16a 16b 16c 17a 17b 17a 18a 18b 18c inabove... All on'e'need do is employ such conventional oxyalkylation procedure to obtain products corresponding to the compositions as defined. :At- 3 tention is; again directed to the fact that one need notadd the entire amountof either oxide atone time but that asmall' portion of one could be added and then another.
small portionof the other, and the process repeated.
butylene oxides and ethylene oxide were mixed; this series isindicatedasAa, Ba, through and including 18a; in the second series butylene voxide was used first followed -rby ethylene oxide and this series indicated Ab, Eb,
through and including 18b; and finally in the third series ethylene oxide was used followed by butylene oxide and the series identified as Ac, Bc, through and including 18C.
-:The products obtained by the above procedure usually .show some color varying from a light amber to a pale straw. They can be bleached in the usual fashion using bleaching clays, charcoal, or an organic bleach, such as peroxide or peracetic acid, or the like.
. Such products also have present a small amount of alkaline catalyst which can be removed by conventional means,'"or...they can be neutralizedby adding an equivalent amount-of .acid, such as hydrochloricacid'. :For
many purposes the slightamountof residual alkalinity is not objectionable. V
There are certain variants which can be employed without detractingxfroin the .metes and bounds of the invention, but for'all practical purposes there is nothing to be gained by. such variants and the result is merely increased cost; For instance, any one of the two oxides can be replaced to a minor percentage and usually to a very small degree, by oxide which would introduce substantially the same; group along with aside chain, for I instance, one could employ glycidyl methyl ether, glycidyl ethyl ether,;glycidyl isopropyl ether, glycidyl butyl ether or. the likeJ-"c;
Increasedbranching also may be effected by the use of animine instead of a glycide, or a methyl glycide.
Thus onefcan useethylene imine, or propylene imine in thesame' wa described for glycide or methyl glycide. An additional efiectis obtained due to the basicity of the ,nitrogenatorn. The same thing is true as far as the inclusion of nitrogen atoms if one uses a compound of the kind previously describedsuch as 'a dialkylaminoepoxypropane; Excellent products areobtained by reacting diglycerol with one to six moles of ethylene' irnine and then proceeding in the same manner herein described.
11111] the hereto appended claims reference. has been made to glycol ethers of diglycerol. Actually it well may be that the products should be referred to as polyol ethers or diglycero in order to emphasize the fact that the final products of reaction have more than two hydroxyl radicals. However, the products may be considered as hypothetically derived by reaction'of diglycerol with the glycols, such as ethylene glycol, butylene glycol, propylene glycol, or polyglycols. For this reason there seems to be a preference to use the terminology'glycol ethers of diglycerol.
PART 3 As to the use of conventional demulsifying agents, reference is made to U.S. Patent No. 2,626,929, dated January 7, 1953, to De Groote, and particularly to Part 3. Everything that appears therein applies with equal force and efiect to the instant process, noting only that where reference is made to Example 13b in said text beginning in. column 15 and ending in column 18, reference should be to Example 18b, herein described. I
Having thus described our invention, what we claim as new and desire to secure by Letters Patent is:
1. A process for breaking petroleum emulsions of the water-in-oil type characterized by subjecting the emulsion to a demulsifying agent including a cogeneric mixture of a homologous series of glycol ethers of acyclic diglycerol; said cogeneric mixture being derived exclusively from acyclic diglycerol, ethylene oxide and butylene oxide in such weight proportions so the average composition of said cogeneric mixture, stated in terms of initial reactants, lies approximately Within the S-Sided figure of the accompanying drawing in which the minimum acyclic diglycerol content is at least 1.5% and which S-sided figure is identified by the fact that its area lies within the straight lines connecting A, B, C, D, and H.
2. The process of claim 1 with the proviso that oxyalkylation takes place in presence of an alkaline catalyst.
3. The process of claim 1 with the proviso that oxyalkylation takes place in presence of an alkaline catalyst and that the butylene oxide be added first.
4. Theprocess of claim 1 with the proviso that oxya-lkylation takes place in presence of an alkaline catalyst and that the butylene oxide be added first, and with the further proviso that the-butylene oxide is substantially free from isobutylene oxide.
5. The process of claim 1 with the proviso that oxyalkylation takes place in presence of an alkaline catalyst and that the butylene oxide be added first, and with the further proviso that the butylene oxide consists of 85% or more of the 1,2-isomer and approximately 15% or less of the 2,3-isomeric form, and is substantially free from isobutylene oxide.
- 6. The process of claim with the proviso that the reactant composition falls within the triangular area defined by C, D, and E.
' 7. The process of claim 5 with the proviso that the reactant composition falls within the parallelogram D, E, F, and J.
8. The process of claim 5 with the proviso that the reactant composition falls within the parallelogram J, F, G, and I.
- 9. The process of claim 5 within the proviso that the reactant composition falls Within the trapezoid I, G, B, and H.
. 10. The process of claim 5 with the proviso that the reactant composition falls within the triangle H, B, A.
11. A process for breaking petroleum emulsions of the water-in-oil' type characterized by subjecting the emulsion to a demulsifying agent including a cogeneric mixture of a homologous series of glycol ethers. of acyclic diglycerol; said cogeneric mixture being derived exclusively from acyclic diglycerol, ethylene oxide and butylene oxide in such weight proportions so the average composition of said cogeneric mixture, stated in terms of initial reactants, lies approximately Within the S-Sided figure of the accompanying drawing in which the minwhich 5-sided figure is identified by the fact that its area lies Within the straight lines connecting A, B, C, -D,
and H; with the proviso that the, hydrophile properties of said cogeneric mixture in an equal weight of xylene are sufiicient to produce an emulsion when said xylene solution is shaken vigorously with one to three volumes of water.
12. The process of claim 11 with the proviso that oxyalkylation takes place in presence of an alkaline catalyst.
13. The process of claim 11 withthe proviso that oxyalkylation takes place in presence of an alkaline catalyst and that the butylene oxide be added first.
14. The process of claim 11 with the proviso that oxyalkylation takes place in presence of an alkaline catalyst and that the butylene oxide be added first, and with the further proviso that the butylene oxide is substantially free from isobutylene oxide.
15. The process of claim 11 with the proviso that oxyalkylation takes place in presence of an alkaline catalyst and that the butylene oxide be added first, and with the further proviso that the butylene oxide consists of or more of the 1,2-isomer and approximately 15% or less 'of the 2,3:isomeric form, and is substantially free from isobutylene oxide.
16. The process of claim 15 with the proviso that the reactant composition falls Within the triangular area defined by C, D, and E.
17. The process of claim 15 with the proviso that the reactant composition falls within the parallelogram D, E, F, and J.
18. The process of claim 15 with the proviso that the reactant composition falls within the parallelogram J, F, G, and I.
19. The process of claim 15 with the proviso that the reactant composition falls within the trapezoid I, G, B, and H.
20. The process of claim 15 with the proviso that the reactant. composition falls within the triangle H, B, A.
References Cited in the file of this patent UNITED STATES PATENTS 2,507,910 Keiser et a1. May 16, 1950 2,552,528 De Groote May 15, 1951 2,574,544 De Groote Nov. 13, 1951 2,617,830 Kosmin Nov. 11, 1952 2,624,766 Butler Jan. 6, 1953 2,662,859 Kirkpatrick Dec. 15, 1953 2,677,700 Jackson et al May 4, 1954
|Cited Patent
|Filing date
|Publication date
|Jan 26, 1949
|May 16, 1950
|Petrolite Corp
|Process for breaking petroleum emulsions
|Jul 14, 1949
|May 15, 1951
|Petrolite Corp
|Process for breaking petroleum emulsions
|Jul 11, 1950
|Nov 13, 1951
|Petrolite Corp
|Process for breaking petroleum emulsions
|Jun 30, 1950
|Nov 11, 1952
|Monsanto Chemicals
|Polyglycol ethers of 7-ethyl-2-methyl-undecanol-4
|Oct 15, 1949
|Jan 6, 1953
|Monsanto Chemicals
|Tridecenyl alcohols
|Jun 15, 1949
|Dec 15, 1953
|Visco Products Co
|Compositions and process for emulsion breaking
|May 31, 1951
|May 4, 1954
|Wyandotte Chemicals Corp
|Polyoxyalkylene surface active agents
|Citing Patent
|Filing date
|Publication date
|Jan 10, 1967
|Mar 10, 1970
|Henkel & Cie Gmbh
|Low foaming washing and cleansing agents
|Oct 29, 1976
|May 5, 1981
|Basf Wyandotte Corporation
|Oxyalkylated polyglycerols and water-based lubricants prepared therefrom
|May 18, 1994
|Apr 9, 1996
|Exxon Chemical Patents Inc.
|Method of demulsifying water-in-oil emulsions
|Jul 3, 1996
|Jul 7, 1998
|Safety-Kleen Corp.
|Enhanced solvent composition
|Jul 7, 1994
|Dec 21, 1999
|Safety-Kleen Corp.
|Method of recycling cleaning solvent
|Feb 9, 2002
|Apr 11, 2006
|Clariant Gmbh
|Alkoxylated polyglycerols and their use as demulsifiers
|May 25, 2004
|Mar 2, 2010
|Clariant Produkte (Deutschland) Gmbh
|Alkoxylated, cross-linked polyglycerols and use thereof as biodegradable demulsifier
|Jan 29, 2002
|Mar 18, 2004
|Dirk Leinweber
|Use of cardanol aldehyde resins as asphalt dispersants in crude oil
|Feb 9, 2002
|Apr 15, 2004
|Dirk Leinweber
|Alkoxylated polyglycerols and their use as demulsifiers
|Jan 29, 2002
|Apr 22, 2004
|Hendrik Ahrens
|Alkyl and aryl alkoxylates as emulsifiers in emulsion polymerisation
|Nov 2, 2001
|May 27, 2004
|Dirk Leinweber
|Resins comprised of alkyl phenols and of glyoxylic acid derivatives, and their use as demulsifiers
|May 25, 2004
|Dec 14, 2006
|Dirk Leinweber
|Alkoxylated, cross-linked polyglycerols and use thereof as biodegradable demulsifier
|Apr 18, 2013
|Sep 5, 2013
|Baker Hughes Incorporated
|Incorporation of Lactones Into Crosslinked-Modified Polyols for Demulsification
|Feb 9, 2002
|Aug 29, 2002
|Clariant Gmbh
|Alkoxylated polyglycerols and their use as demulsifiers
|Feb 9, 2002
|Nov 7, 2002
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|Alkoxylated polyglycerols and their use as demulsifiers
|U.S. Classification
|516/191, 568/624, 568/623, 568/620
|International Classification
|Cooperative Classification
|European Classification


text:
PITTSBURGH: Chatham University's Bachelor's and MBA programs earned a Best Online Program ranking by U.S. News & World Reports in their 2016 Best Online Programs edition.
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Murah, where did you get your figure of $120m a year, is that a random number? Amendment increased total net interest rates 400 basis points. On $3.1B that is $12.4M (not over $100M!). And the $100M was pre-paid debt.In any case, if this is an example of the worst that can happen due to MTW's debt convenants I am moving on to other concerns.
That is not the worst that can happen. Bankrupcy would be the worst case scenario, and in fact, very possible, if MTW starts breaking the debt covenants.
why would there be a dividend if there was talks of bankruptcy the stock was just dragged down with the market... nice bear rally and we should be back in business
and if they don't, wise one?


text:
Rose's Turn Lyrics
Rose's Turn Song Lyrics
Here she is, boys!
Here she is, world!
Here's Rose!
Curtain up!
Light the lights!
Play it, boys!
Ya either got it, or ya ain't.
And, boys, I got it!
Ya like it?
Well, I got it!
Some people got it and make it pay.
Some people can't even give it away.
This people's got it
and this people's spreadin' it around!
You either have it
or you've had it!
Hello, everybody! My name is Rose! What's yours?
How do you like them eggrolls, Mr. Goldstone?
Hold your hats and hallelujah.
Mama's gonna show it to you.
Ready or not, shhh, here comes Mama.
Mama's talkin' loud.
Mama's doin' fine.
Mama's gettin' hot.
Mama's goin' stong.
Mama's movin' on.
Mama's all alone.
Mama doesn't care.
Mama's lettin' loose.
Mama's got the stuff.
Mama's lettin' go.
Mama's got the stuff.
Mama's gotta move.
Mama's gotta go.
Mama? Mama?
Mama's gotta let go.
Why did I do it?
What did it get me?
Scr*pbooks full of me in the background.
Give 'em love and what does it get ya?
What does it get ya?
One quick look as each of 'em leaves you.
All your life and what does it get ya?
Thanks a lot and out with the garbage,
They take bows and you're battin' zero.
I had a dream.
I dreamed it for you, June.
It wasn't for me, Herbie.
And if it wasn't for me
then where would you be,
Miss Gypsy Rose Lee?
Well, someone tell me, when is it my turn?
Don't I get a dream for myself?
Starting now it's gonna be my turn.
Gangway, world, get off of my runway!
Starting now I bat a thousand!
This time, boys, I'm taking the bows and
everything's coming up Rose!
Everything's coming up roses!
Everything's coming up roses
this time for me!
For me! For me! For me! For me! For me!
For me! Yeah!
[Rose takes the silent bows as Gypsy enters and applauds]
I was...trying out for you...New ideas you might wanna use...
You really would have been something, momma!
Do you think so?
If you had someone to push you like I had...
If I could have been...I would have been...
And that's show business!
I guess I did it for me...
Why, momma?
Just wanted to be noticed...
Like I wanted you to notice me!
I still do, momma!
[They embrace each other. Rose cries]
It's OK, momma! OK, Rose!
See... You look like you should speak French!
You're coming to that party with me...
Come on!
Not like this.
Wear my fur I have a stole in my cabinet.
Well, maybe just for an hour or two...Hey, it looks better on me than it
does on you. Funny how we can both wear the same size!
Specially in mink.
You know...I had a dream last night. There was a big poster of a mother
and daughter, like the covers of the ladies magazines...
Yes, momma!
Only it was you and me wearing exactly the same gowns. It was an add for
Minsky, and the headline said: "MADAM ROSE...AND HER DAUGHTER GYPSY".
[They laugh, embrace each other and leave. Rose stops for a while and
take one last look at the stage as if she said good-bye.]
Gypsy Lyrics
Soundtrack for Musical, 2003
Rose's Turn Lyrics from Gypsy Soundtrack (2003). Rating: 4.2/5 (21 votes)
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ssh: Could not resolve hostname xxx: Name or service not known
Type: Posts; User: Karlas; Keyword(s):
ssh: Could not resolve hostname xxx: Name or service not known
Oh Is there a way to find out username and hostname of that computer?????
Ok I got the idea,1 more question,I could just run downstairs and check my other computers IP,but is there anyway to see it without doing that?Im using wlan.
Yes the other computer has Ubuntu too,can you explain a bit more?
So yeah,the title says it all,is there anyway to do it?
CPU intel Celeron T3500 2.1 Ghz Dual.
Graphic Card Intel GMA 4500M
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oK guys Thank for all the answers!I guess Ill try it some time .future
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destination directory: hg.barrelfish.org
abort: destination 'hg.barrelfish.org' is not empty
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text:
Crazy Substitute Teachers
Enjoy, NG4.02 / 5.00 2,532 Views
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This dude and his Megazord vacuum cleaner4.01 / 5.00 2,813 Views
Markiplier Animated | Mark Of The Survey Corps
This took far too long to make...3.96 / 5.00 6,966 Views
shit lol
One of the best series here on NG! It's emotional factor nearly made me cry. Not many animations can do that.It's sad that this ended the series, but it was a great finale. The dad was a prick, the omo was a sweetheart, and Jerry was...JERRY. I'm glad this one had a good ending. I wished Jerry could've gotten a better end to his life. He should've gone to heaven, and his dad should've been getting his dick roasted in hell. But it was your series, so cudos, HDD, you made a great series that'll remain in our hearts for eternity.
Finally Jerry gets a happy ending, great series
A MUCH better conclusion than Wacky Game Jokez's
To be honest, you really played a lot with the emotional factor of this series in this finale. We FINALLY see the biggest event in Jerry's childhood. I mean, you did a great job showing why he's so depressed and everything. I also love that heart to heart talk with Jerry and his mom. The voice you chose for her was superb, absolutely fitting.
I was also surprised to hear Jerry talk, too. Good voice actor, and you show good emotion yourself, man.
I also love Jason in this one. We see an entirely different side to him in serious situations.
While Wacky Game Jokez isn't my favorite series, I like this series a bit.
You concluded this show on such a great note.
I just wish you didn't have that ending with Jackie. Just a personal opinion, not big problem.
Its a great ending to a fantastic series...


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Procrastination is one of the top reasons students are in academic difficulty. So why do students continue to do it despite knowing its outcomes? Learn more about strategies to reduce and eliminate this behavior and how to prepare for next semester.
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Skip to comments.June 5, 1968 - On This Day In History: Robert F. Kennedy Shot
Posted on 06/05/2007 9:38:26 AM PDT by DogByte6RER
1968 - Robert F. Kennedy shot
At 12:50 a.m. PDT, Senator Robert F. Kennedy, a presidential candidate, is shot three times in a hail of gunfire in the Ambassador Hotel in Los Angeles. Five others were wounded. The senator had just completed a speech celebrating his victory in the California presidential primary. The shooter, Palestinian Sirhan Sirhan, had a smoking .22 revolver wrested from his grip and was promptly arrested. Kennedy, critically wounded, was rushed to the hospital, where he fought for his life in the next 24 hours. On the morning of June 6, he died. He was 42 years old.
(Excerpt) Read more at history.com ...
Sirhan Sirhan was one of the first Islamofascist terrorists. He fired the first shot 39 years ago that has since put Western Civilization in a clash against radical Islamofascism.
Not to dispute the threat of the Islamists but Sirhan was Christian.
Maybe that's why "the swimmer" hates us so much
Man, that was 40 years ago? And I'm still being told to mow the lawn.
The Swimmer has killed as many people as Sirhan Sirhan.
Prayers to the family on this difficult day.
I watched his victory speech on TV then went to bed when he finished. Good thing since I had to get to my summer job at 7:00am. Was trying to date a girl I was working with who was a RFK fan, but when she found out I supported Reagan, it was over.
Silly Borges! Never let facts get in the way of an anti-Islamic rant.
From his Wikipedia article:
Sirhan was born to Palestinian Christian parents in Jerusalem and was raised in the Maronite Church. In his adult life, however, he made several religious conversions, joining Baptist and Seventh-day Adventist Churches, and dabbled in the occult.(P.S.: I know, Wikipedia isn't always reliable)
My God, thirty nine years ago....imagine....I remember it like it happened yesterday, still sends shivers down my spine, wonder what this country would be like now if Jack and Bobby lived.............
Not to be crude, but I always thought that photo of the waiter appeared a bit staged, why isn't someone trying to help the Senator - if he is still alive in that photo? I had no idea Bobby was only 42.
I met, or at least witnessed, RFK at a party the summer before this happened. What a prima donna.
He was up in his room after all the guests arrived, and the host and hostess were frantic because it looked as if he would refuse to come down and be seen.
Then Mike Mansfield arrived. When RFK heard he was there, he decided he had better come down after all, because Mansfield wasn't someone he could afford to cross.
"My God, thirty nine years ago....imagine....I remember it like it happened yesterday, still sends shivers down my spine, wonder what this country would be like now if Jack and Bobby lived............."
...a complete socialist state. With Teddy at the helm. Teddy would've had strict instructions from Jack and Bobby to keep his big red nose clean so as to not hurt the name. Jack, being unable to keep his trouser snake where it belonged, would've been the extent of "released" controversy in the family.
Why all the fawning over this dead POS??? He was one of the most crooked AG's ever.
I read a book recently whose author theorizes that Sirhan was a pawn and Onassis was actually behind RFK's murder. I'm not sure I buy it, but the book is pretty well documented.
I watched the re-running of From the Earth to the Moon on the Science channel...(originally run on HBO in 1998).
the episode was called 1968.
So much came down that year.....it was a never ending mess, set in motion, for the most part, by LBJ.
one scene depicted the death of RFK.
the end depicted the Christmas orbiting of the Moon in Apollo 8, by Borman, Lovell and Anders. On Christmas eve they read from the Bible and wished everyone on the earth a Merry Christmas. It brought a tear watching the show, as it did to me in 1968 when it actually happened.
The flight to the moon that saved 1968.
I know that his isn't the subject of this thread, but couldn't help adding to what you said. I had a friend (not even a dating relationship) who cut me off because we didn't agree on politics. Seems to be a liberal thing: I know of no conservatives who act that way.
I fell asleep in front of the TV. When I began to hear the words "Kennedy shot" I thought I was reliving November 1963.
Actually, he was crooked but in an honest way. JFK and Bobby got the Mafia to help steal the Presidential election, then they turned on the Mafia with hearings and investigations.
The karmic part of the assassination was that without Ted Kennedy's screwing up immigration laws, his brother would not have been assassinated - Teddy put through the 1965 immigration bill that let turd worlders into America - like Sirhan Sirhan.
You quoted from Wikipedia to dispell an Islamofacinaziwhatever rant? Are you going to let simple facts get in the way of whipping up another mindless frenzy?!?
I'm just being honest, plus you are missing the difference. The Rev Falwell was never in a position of (governmental) power over other people, while RFK choose to seek that power. Nobody was ever under Falwell's thumb, but Bobby lived for control over others.
There is no way I could have ever dated, much less married a liberal.
It's surprising they even mention who clipped him.
As a wise Freeper said (I don't recall their name) perhaps Ted is still around to show us.
They double-crossed the mob, tried to kill Fidel, angered the Russians, slept with all sorts of different women - some married to powerful men. The list of suspects in the Kennedy assassinations should be quite lenghty.
Oh, I'm with you on that one. As I said, this wasn't even a dating relationship, let alone one that might have led to marriage.
BTW, I'm grateful that my conservative wife didn't take that approach. When we met, and even during the early years of our marriage, I considered myself liberal.
soulless ones.
I remember that well too, as well as the Kennedy assassination and the King assassination two months earlier. 1968 was certainly a tumultuous year. God Bless Borman, Lovell, and Anders.
He was Christian, as were a number of the terrorists of the early 70s. Sirhan was a loner, but the PFLP was a Christian founded terrorist group to be reckoned with, a PLO member, responsible for a large number of hijackings and airport attacks in the late 60s and 70s. Suicide bombing didn't seem to catch on with them.
JFK would have been a Reagan Democrat.
Sorry, I don't ever think it's good to see a candidte murdered.
'My God, thirty nine years ago....imagine....I remember it like it happened yesterday, still sends shivers down my spine, wonder what this country would be like now if Jack and Bobby lived.............'
Two geopolitical virgins, the older of which damn near blew the world up twice, was heavily drugged, and carrying on a half dozen affairs at the same time....the younger of which its been said despised anyone that was brighter than he (JFK allegedly said it twice)?
Sorry, THAT thought sends shivers up my spine. They were the two 'genius's' that got us heavily into Vietnam.
No thanks, we're lucky we survived the Kennedy 'era'.
A pan-Arab Marxist group, as were all of the original PLO members, enamored of Che, more accurate to call them athiests. Over the years it's become Islamist.
I've always wondered if Jack was such a stoner, how could he get it "up" so often for all his chicks?
'Ive always wondered if Jack was such a stoner, how could he get it up so often for all his chicks?'
Depends on the drug and the constitution of the person taking it in my experience.
Directly. That we know of.
If you count the results of policies he's either devised, advocated or supported, the number reaches into the millions in SE asia alone....
This film suggests at least one possibility.....
"Suicide bombing didn't seem to catch on with them.
Without the virgins, it probably doesn't seem like such a good idea.
He was no prima donna, just a good man like the West makes'um.
For those too young to know: Senator Mike Mansfield represented his home state of Montana for several terms as a Republican, then was appointed ambassador to Japan.
The way I saw it, Bobby Kennedy stole the thunder of Gene McCartney in his anti-war pursuit of the presidency. He was a prima donna for that reason alone (but your story adds to my beliefs about him).
And then there's the stories about Marilyn......
Mansfield was a Democrat (and was Senate Majority Leader when the Democrats held the Senate).
But they held a special hatred for...GUNS!
The JFK, Medgar Evers and Martin Luther King shootings were used to kindle the fire, and the Bobby Kennedy killing set off a conflagration.
The result was ,
less violent comic books for a while, a very short while.
Dumbed down TV shows, More kid friendly, less shooting or adult themes.
Movie moguls declared they would police themselves with a rating system (Censorship is gone! More violence and nudity! have at it boys).
And that travesty imposed on us, the 1968 Gun Control Act (the Nazi Weapons act of the 1930's rewritten by Thomas J. Dodd.)
Dodd had been trying for seven years to get gun control in the US. And the 1968 law was mild compared to what he really wanted. The NRA managed to cool things down a little.
In that year I learned the worst legislation can be bought by PORK! The 1968 GCL was passed only because it contained a large amount of money for each state to be used for "Crime Control"
It's like another law in 1994 that only passed because it contained a large amount of money for "crime control", the AWB.
To get a feeling what it was like in 1968, you should go to a public library and take a look at their magazine archives for LIFE, LOOK and SATURDAY EVENING POST to to see what madness we were up against.
Mafia, StoneCutters, LBJ, Castro, Space Aliens, Right Wing Conspiracy....
Oops. Sorry. Wrong Thread.
Disclaimer: Opinions posted on Free Republic are those of the individual posters and do not necessarily represent the opinion of Free Republic or its management. All materials posted herein are protected by copyright law and the exemption for fair use of copyrighted works.


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text: > So clearly they're allowed, in 1.2_3 the underscore is simply=20 > ignored and > the parser should undestand 1.23. If I fancy to write my own=20 > YAML by hand > and make it easily readable (which is kind of the original=20 > purpose) I could > write 100_000_000.03 which would be a nice looking float. Hence the > ambiguity with "1.2_3" Hmmmm... I just noticed that the specification (http://yaml.org/type/float.html) isn't just unclear, it's inconsistent. The examples listed include: exponentioal: 685.230_15e+03 Notwithstanding the spelling of exponential, that example is not consistent with the regular expression (which allows underscores only if they preceed the decimal point - [-+]?([0-9][0-9_]*)?\.[0-9.]*([eE][-+][0-9]+)?). Dan.


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Lynne Graham lives in Northern Ireland and has been a keen romance reader since her teens. Happily married, Lynne has five children. Her eldest is her only natural child. Her other children, who are every bit as dear to her heart, are adopted. The family has a variety of pets, and Lynne loves gardening, cooking, collecting allsorts and is crazy about every aspect of Christmas.
Una noche con su mujer (One Night with His Wife) (Harlequin Bianca Series #986)by Lynne Graham
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- Harlequin
- Publication date:
- 05/06/2014
- Series:
- Harlequin Bianca Series, #986
- Edition description:
- Spanish Language Edition
- Pages:
- 160
- Product dimensions:
- 4.20(w) x 6.60(h) x 0.50(d)
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JAA prepping for Embraer decision with 50 jobs hanging in the balance
Friday, December 21, 2012
Jacksonville Business Journal
by Michael Clinton, Web Producer
The Jacksonville Aviation Authority is renovating the former Piedmont hangar in preparation for a decision on a contract that could bring 50 high-paying jobs to Jacksonville.
JAA is expecting the U.S. Air Force to make a contract decision for the construction of light attack aircraft — the same contract that Embraer and Sierra Nevada Corp. won a year ago and were planning to build the A-29 Super Tucano at the Jacksonville International Airport, the Daily Record & Financial News reports.
Sierra Nevada asked a federal court to reinstate the defense contract awarded to the company in June.
The Air Force chose Sierra Nevada over competitor aircraft manufacturer Hawker Beechcraft, but canceled the Light Air Support contract at the end of February and decided to rebid the contract to both companies.
Hawker Beechcraft, based in Wichita, Kan., filed a lawsuit contesting the bidding process with the U.S. Court of Federal Claims in December 2011.
Source: http://bit.ly/Wuj5XW