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(12) United States Patent (10) Patent No.: US 8,614,267 B2 Hill Et Al

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(12) United States Patent (10) Patent No.: US 8,614,267 B2 Hill Et Al 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. (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 151 days. FOREIGN PATENT DOCUMENTS This patent is Subject to a terminal dis AT 243952 12/1965 claimer. DE 1494922 6, 1969 (21) Appl. No.: 13/121,889 (Continued) OTHER PUBLICATIONS (22) PCT Filed: Oct. 6, 2009 PCT International Search Report for PCT/EP2009/007 145, mailed Jan. 25, 2010. (86). PCT No.: PCT/EP2009/007124 English Translation of the PCT International Preliminary Report on Patentability PCT/EP2009/007 145 mailed Jun. 30, 2011. S371 (c)(1), English abstract for JP 05230085, Sep. 7, 1993. (2), (4) Date: Mar. 30, 2011 Russian Journal of General Chemistry (translation of Zhurnal Obschchei Khimi), 74(6) pp. 864-872: XP002561442 (2004). (87) PCT Pub. No.: WO2010/051884 PCT International Search Report for PCT/EP2009/007 123, mailed Jan. 29, 2010. PCT Pub. 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. R. are the same or 3,784,638 A * 1/1974 Lambert ....................... 562,594 different and stand independently of each other, among other 3,875,263. A 4/1975 Herwig et al. 3,939,050 A 2f1976 Kleiner et al. things, for H. C-Cls alkyl, C-Cls aryl, C-Cls aralkyl, 3,941,752 A 3, 1976 Kleiner et al. C-Cls alkylaryl, and X stands for H. C-Cs alkyl, C-Cls 3,962,194 A 6, 1976 Bollert et al. aryl, C-C saralkyl, C-C alkylaryl, Mg, Ca, Al, Sb, Sn, Ge. 4,001,352 A 1/1977 Kleiner et al. Ti, Fe, Zr, Zn, Ce, Bi, Sr., Mn, Cu, Ni, Li, Na, K and/or a 4,035,343 A 7, 1977 Bollert et al. protonized nitrogen base, and the catalyst A is formed by 4,069,245 A 1/1978. Dursch et al. 4,069,247 A 1/1978 Kleiner transition metals and/or transition metal compounds and/or 4,079,049 A 3/1978 Ramsey et al. catalyst systems composed of a transition metal and/or a 4,168.267 A 9, 1979 Petrillo transition metal compound and at least one ligand, and cata 4,235,991 A 11/1980 Digiacomo lyst B is formed by compounds forming peroxides and/or 4,337,201 A 6, 1982 Petrillo peroxo compounds and/or azo compounds. 4,374,131 A 2, 1983 Petrillo 4,381,297 A 4, 1983 Karanewsky et al. 11 Claims, No Drawings US 8,614,267 B2 Page 2 (56) References Cited EP 1832596 9, 2007 EP 1905776 4/2008 U.S. PATENT DOCUMENTS GB 1045684 10, 1966 JP O5230085 9, 1993 6,090,968 A 7/2000 Horold et al. WO WO99,28327 6, 1999 6.214,812 B1 4/2001 Karpeisky WO WOO1/42252 6, 2001 6,355,832 B1 3/2002 Weferling et al. WO WOO157.050 8, 2001 6,384,022 B1 5/2002 Jackson et al. WO WO O2/10O871 12/2002 6,569,974 B1 5/2003 Sicken et al. WO WO 2005/O14604 2, 2005 6,727,335 B2 4/2004 Sicken et al. 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Amsterdam, NL vol. 48, No. 33, pp. 5755-5759, XPO22163552 (Jul. 2006/0264654 A1 11, 2006 Wehner 19, 2007). 2007/0210288 A1 9, 2007 Maas et al. Sylvine Deprele et al.: “Environmentally Benign Synthesis of 2007/021343.6 A1 9, 2007 Maas et al. H-Phosphinic Acids. Using a Water Tolerant, Recyclable Polymer 2007/0213563 A1 9, 2007 Maas et al. Supported Catalyst.” Organic Letters, American Chemical Society, 2008. O183009 A1 7, 2008 Wehner et al. US, vol. 6, No. 21, pp. 3805-3808 XP002500861 (Jan. 1, 2004). 2008, 0214708 A1 9, 2008 Bauer et al. Patrice Ribiere et al: "NiCL2-Catalyzed Hydrophosphinylation.” 2009/0286759 A1 1 1/2009 Gallop et al. Journal of Organic Chemistry, American Chemical Society, Easton, 2010/00932.39 Al 4, 2010 Bauer et al. US, vol. 70, No. 10, pp. 4064-4072, XP002530191 (Jan. 1, 2005). 2011/02130522011/0201732 A1 9,8/2011 2011 HillHill et al. Courdravourdray L. et al.:al.:"Allvlic Allylic PhosphinatesPhospinnates via Fd-UatalyzedPd-Catalvzed AllylationAllvilati 2011/0213059 A1 9, 2011 Hill et al. of H-Phosphinic Acids with Allylic Alcohols:”Organic letters, vol. 2011/0213060 A1 9, 2011 Hill et al. 10, No. 6, pp. 1123-1126 XP002561368 (Feb. 21, 2008). 2011/0213061 A1 9, 2011 Hill et al. MastalerZ: Synthesis of some ethylene-(PP-Dialkyl)-Diphosphic 2011/0213062 A1 9, 2011 Hill et al. Acids as new Potential Antimetabolites of Succinic Acid; Roczniki 2011/0213078 A1 9, 2011 Hill et al. Chemii Ann. Soc. Chim. Polonorum, vol. 38 pp. 61-66 XP 2011/0213079 A1 9, 2011 Hill et al. 009 126234 (1964). 2011/0213080 A1 9, 2011 Hill et al. Kurdyumova et al.: “Synthesis of Phosphinic Acids from 2011/0224339 A1 9, 2011 Hill et al. Hypophosphites I Acrylates as an Unsaturated Component; Russian 2011/0234340 A1 9, 2011 Hill et al. Journal of General Chemistry (Translation of Zhurnal Obshchei 2011/0237720 A1 9, 2011 Hill et al. 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