(IO)  Patent No.:  US 7,902,392 B2  (45)  Date of Patent:  Mar.8,2011  c12)  United States Patent  Ochs et al.  (54)  METHOD FOR THE PRODUCTION OF  ORGANOSILICON COMPOUNDS  COMPRISING CARBOXY RADICALS  (75)  Inventors:  Christian Ochs,  Burghausen (DE);  Elke  Fritz-Langhals,  Ottobrunn (DE)  (73)  Assignee:  Wacker Chemie AG,  Munich (DE)  ( *)  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U .S.C. 154(b) by 1118 days.  (21)  Appl. No.:  11/568,050  (22)  PCT Filed:  Apr. 11, 2005  (86)  PCT No.:  PCT /EP2005/051588  § 371 (c)(l),  (2), ( 4) Date:  Oct. 18, 2006  (87)  PCT Pub. No.:  WO2005/103060  (51)  Int. Cl.  C07F  7104  (2006.01)  C07F  7108  (2006.01)  (52)  U.S. Cl.  .........................................  556/439;  205/420  (58)  Field of Classification Search  ........................ None  See application file for complete search history.  (65)  Prior Publication Data  (30)  Foreign Application Priority Data  17 Claims, No Drawings  (57)  ABSTRACT  OTHER PUBLICATIONS  FOREIGN PATENT DOCUMENTS  U.S. PATENT DOCUMENTS  (56)  References Cited  2,763,675  A  9/1956 Porchaska et al.  2,875,177  A  2/1959 Bluestein et al.  2,900,363  A  8/1959 Bluestein et al.  2,957,899  A  10/1960 Black et al.  3,143,524 A  8/1964 Cooper et al.  3,391,177 A  7/1968 Niederprum et al.  4,990,643  A  2/1991 Traver  5,504,233  A  4/1996 Bind! et al.  5,637,746  A  6/1997 Knebelkamp et al.  6,127,573  A  *  10/2000 Li et al. ......................... 562/419  6,169,213 Bl  1/2001 Fritz-Langhals et al.  6,750,371 B2  *  6/2004 Fritz-Langhals et al. ..... 568/471  2003/0073871 Al  4/2003 Fritz-Langhals et al.  EP  O  196 169 Bl  3/1993  EP  O  569 189 Al  11/1993  EP  1 302 456 Al  4/2003  WO  WO 99/52849 A  10/1999  PCT Pub. Date:  Nov. 3, 2005  US 2009/0221842 Al  Sep.3,2009  Apr. 21, 2004  (DE) ......................... 10 2004 019 376  US007902392B2  English Abstract corresponding to EP 1 302 456 Al.  Anelli, et al.: "Fast and Selective Oxidation of Primary Alcohols to  Aldehydes or Tocarboxylic Acids and of Secondary Alcohols to  Ketones Mediated by Oxoammonium Salts under Two-Phase Con› ditions", Journal of Organic Chemistry, American Chemical Society.  Easton, US, vol. 52, No. 12, Jun. 12, 1987, pp. 2559-2562.  Enzyme Nomenclature, Academic Press, Inc., 1992, pp. 24-154.  *  cited by examiner  Primary Examiner  - Daniel M Sullivan  Assistant Examiner  - Chukwuma O Nwaonicha  (74)  Attorney, Agent, or Firm  - Brooks Kushman P.C.  Organosilicon compounds bearing carboxylic acid groups are  easily and economically replaced in high yield by oxidation  of a carbinol-functional organosilicon compound with an  oxidizer in the presence ofa moderator at a pH~3. Carboxyl› functional organopolysiloxanes highly useful as textile soft› eners may be obtained by this method. 