USOO8614267B2 (12) United States Patent (10) Patent No.: US 8,614,267 B2 Hill et al. (45) Date of Patent: *Dec. 24, 2013 (54) METHOD FOR PRODUCING 4.414,352 A * 1 1/1983 Cohen et al. .................. 524. 443 MONO-HYDROXYFUNCTIONALIZED 4,555,5064.427,665 A 1 1/19851/1984 Karanewsky et al. DALKYLPHOSPHINCACDS AND ESTERS 4,594,199 A 6, 1986 Thottathil et al. AND SALTS THEREOF BY MEANS OF ALLYL 4,602,092 A 7/1986 Thottathil et al. ALCOHOLS AND USE THEREOF 4,634,689 A 1/1987 Witkowski et al. 5,013,863. A 5/1991 Baylis et al. 5,153,347 A 10, 1992 Lloyd (75) Inventors: Michael Hill, Cologne (DE), Werner 5, 190,934 A 3, 1993 Mi3. et al. Krause, Huerth (DE); Martin Sicken, 5,229,379 A 7/1993 Marescaux et al. Cologne (DE) 5,391,743 A 2f1995 Ebetino et al. 5,407,922 A 4, 1995 Marescaux et al. (73) Assignee: Clariant Finance (BVI) Limited, 5,739,1235,545,631 A 4,8, 19981996 NEl.M Tortola (VG) 5,780,534. A 7/1998 Kleiner et al. 6,013,707 A 1/2000 Kleiner et al. 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Date: May 14, 2010 English Translation of the PCT International Preliminary Report on Patentability PCT/EP2009/007 123 mailed May 19, 2011. (65) Prior Publication Data Montchamp; "Recent advances in phosphorus-carbon bond forma tion: synthesis of H-phosphinic acid derivatives from hypophosphus US 2011 FO2O1733 A1 Aug. 18, 2011 compounds' Journal of Organometallic Chemistry Elsevier-Sequoua S.A. Lausanne, CH, vol. 690; pp. 2388-2406; XP004877374 (May (30) Foreign Application Priority Data 16, 2005). Nov. 5, 2008 (DE) ......................... 10 2008 O55,916 (Continued) Primary Examiner — Doris Lee (51) Int. Cl. (74) Attorney, Agent, or Firm — Anthony A. Bisulca CSK 5/533 (2006.01) (52) U.S. Cl. (57) ABSTRACT USPC .............. 524/115:524/133; 558/208; 558/87 The invention relates to a method for producing mono-hy (58) Field of Classification Search droxyfunctionalized dialkylphosphinic acids and esters and USPC .......................................................... 524/115 salts thereof by means of allyl alcohols, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to See application file for complete search history. yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic (56) References Cited acid, salt or ester (II) thereof is reacted with compounds of U.S. PATENT DOCUMENTS formula (V) to yield a mono-hydroxyfunctionalized dialky lphosphinic acid derivative (III) in the presence of a catalyst 3,345,432 A 10, 1967 Gillham et al. B, wherein R', R. R. R. R. R. R. R. 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