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(12) United States Patent (10) Patent No.: US 9,018,413 B2 Hill Et Al

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(12) United States Patent (10) Patent No.: US 9,018,413 B2 Hill Et Al USOO90 18413B2 (12) United States Patent (10) Patent No.: US 9,018,413 B2 Hill et al. (45) Date of Patent: Apr. 28, 2015 (54) METHOD FOR THE PRODUCTION OF 4,079,049 A 3/1978 Ramsey et al. 4,168.267 A 9, 1979 Petrillo ALKYLPHOSPHONIC ACIDS, ESTERS, AND 4,235,991 A 11/1980 Digiacomo SALTS BY OXDZING 4,337,201 A 6, 1982 Petrillo ALKYLPHOSPHONOUS ACIDS, AND USE 4,374,131 A 2, 1983 Petrillo THEREOF 4,381,297 A 4, 1983 Karanewsky et al. 4.427,665 A 1/1984 Karanewsky et al. (75) Inventors: Michael Hill, Cologne (DE); Werner 4,555,506 A 11/1985 Karanewsky et al. 4,594,199 A 6, 1986 Thottathil et al. Krause, Huerth (DE); Martin Sicken, 4,602,092 A 7/1986 Thottathil et al. Cologne (DE) 4,634,689 A 1/1987 Witkowski et al. 4,670,193 A * 6/1987 Thottathil ......................... 562/8 (73) Assignee: Clariant Finance (BVI) Limited, 5,013,863. A 5/1991 Baylis et al. Tortola (VG) 5,153,347 A 10/1992 Lloyd 5, 190,934 A 3, 1993 Mickel et al. 5,229,379 A 7/1993 Marescaux et al. (*) Notice: Subject to any disclaimer, the term of this 5,391,743 A 2f1995 Ebitino et al. patent is extended or adjusted under 35 5,407,922 A 4, 1995 Marescaux et al. U.S.C. 154(b) by 402 days. 5,545,631 A 8, 1996 Marescaux 5,739,123 A 4/1998 Norcini et al. (21) Appl. No.: 13/140,225 5,780,534 A 7/1998 Kleiner et al. 6,013,707 A 1/2000 Kleiner et al. (22) PCT Filed: Oct. 6, 2009 (Continued) (86). PCT No.: PCT/EP2009/007 142 FOREIGN PATENT DOCUMENTS S371 (c)(1), AT 243952 12/1965 (2), (4) Date: Jun. 16, 2011 DE 1494922 6, 1969 (87) PCT Pub. No.: WO2010/069418 (Continued) PCT Pub. Date: Jun. 24, 2010 OTHER PUBLICATIONS (65) Prior Publication Data Montchamp et al. J. Organomet. Chem. 690 (2005), 2388-2406.* US 2011 FO251314 A1 Oct. 13, 2011 (Continued) (30) Foreign Application Priority Data Primary Examiner — Susannah Chung Dec. 18, 2008 (DE) ......................... 10 2008 O63 668 Assistant Examiner — Robert T. Butcher (51) Int. Cl. (74) Attorney, Agent, or Firm — Anthony A. Bisulca C07F 9/22 (2006.01) C09K2L/2 (2006.01) (57) ABSTRACT C07F 9/38 (2006.01) C07F 9/40 (2006.01) The invention relates to a method for producing monocar C07F 9/48 (2006.01) boxy-functionalized dialkylphosphinic acids, esters, and CSK 5/537 (2006.01) salts, characterized in that a) a phosphinic acid source (I) is (52) U.S. Cl. reacted with olefins (IV) in the presence of a catalyst A to CPC ............... C09K21/12 (2013.01); C07F 9/3808 (2013.01); C07F 9/4006 (2013.01); C07F obtain an alkylphosphonous acid, the salt or ester(II) thereof, 9/4816 (2013.01); C07F 9/4866 (2013.01); and b) the obtained alkylphosphonous acid, the salt or ester C08K 5/5317 (2013.01) (II) thereof is reacted with an oxidizing agent or with an (58) Field of Classification Search oxidizing agent and water or with oxygen and water in the None presence of a catalyst B to obtain the alkylphosphonic acid See application file for complete search history. derivative (III), wherein R', R. R. Rare identical or differ ent from each other and independently represent, interalia, H. (56) References Cited C-Cls-alkyl, C-C-aryl, C-Cls-aralkyl, C-Cls-alkylaryl, X and Y are identical or different from each other and inde U.S. PATENT DOCUMENTS pendently represent H, C-Cls-alkyl, C-C-aryl, C-Cls 3,345,432 A 10, 1967 Gillham et al. aralkyl, C-C-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge. Ti, Fe, Zr, 3,784,638 A 1/1974 Lambert Zn, Ce, Bi, Sr., Mn, Cu, Ni, Li, Na, K and/or a protonated 3,875,263. A 4/1975 Herwig et al. nitrogenous base, and catalysts A and B are transition metals 3,939,050 A 2f1976 Kleiner et al. and/or transition metal compounds and/or catalyst systems 3,941,752 A 3, 1976 Kleiner et al. 3,962,194 A 6, 1976 Bollert et al. composed of a transition metal and/or a transition metal com 4,001,352 A 1/1977 Kleiner et al. pound and at least one ligand. 4,035,343 A 7, 1977 Bollert et al. 4,069,245 A 1/1978. Dursch et al. 4,069,247 A 1/1978 Kleiner 4 Claims, No Drawings US 9,018,413 B2 Page 2 (56) References Cited EP 1693.403 8, 2006 EP 1832594 9, 2007 U.S. PATENT DOCUMENTS EP 1832595 9, 2007 EP 1832596 9, 2007 6,090,968 A 7/2000 Horold et al. EP 1905776 4/2008 6.214,812 B1 4/2001 Karpeisky GB 1045684 10, 1966 6,278,012 B1* 8/2001 Horold et al. ................. 558/110 JP O5230085 9, 1993 6,355,832 B1 3/2002 Weferling et al. WO WO99,28327 6, 1999 6,384,022 B1 5/2002 Jackson et al. WO WOO1/42252 6, 2001 6,569,974 B1 5/2003 Sicken et al. WO WOO157.050 8, 2001 6,727,335 B2 4/2004 Sicken et al. WO WO O2/10O871 12/2002 6,855,757 B2 2/2005 Horold et al. WO WO 2005/O14604 2, 2005 7,446,140 B2 11/2008 Bauer WO WO 2005/032494 4/2005 7,473,794 B2 1/2009 Wehner et al. WO WO 2005/044830 5, 2005 7,485,745 B2 2/2009 Maas et al. WO WO 2007/0521.69 5/2007 7,749,985 B2 7/2010 Gallop et al. WO WO 2008/033572 3, 2008 7,829,736 B2 11/2010 Wehner et al. WO WO 2008/043499 4/2008 8,084,518 B2 12/2011 Bauer 8,097,753 B2 1/2012 Maas et al. OTHER PUBLICATIONS 2002fO187977 A1 12, 2002 Pearlman et al. 2003/0171466 A1 9, 2003 Horold et al. US 6,248.921, 06/2001, Weferling et al. (withdrawn). 2003/0216533 A1 11/2003 Sicken et al. PCT International Search Report for PCT/EP2009/007 145, mailed 2005/O1871.96 A1 8, 2005 Madrid et al. Jan. 25, 2010. 2006, OO84734 A1 4/2006 Bauer et al. English Translation of the PCT International Preliminary Report on 2006/0194973 A1 8/2006 Gainer et al. Patentability PCT/EP2009/007 145 mailed Jun. 30, 2011. 2006/0264654 A1 11/2006 Wehner et al. 2007/0029532 A1 ck 2, 2007 Hansel et al. 252/.609 English abstract for JP 05230085, Sep. 7. 1993. 2007/0210288 A1 9, 2007 Maas et al. Russian Journal of General Chemistry (translation of Zhurnal 2007021343.6 A1* 9, 2007 Maas et al. .................... 524f133 Obschchei Khimil), 74(6) pp. 864-872; XP002561442 (2004). 2007/0213563 A1 9, 2007 Maas et al. PCT International Search Report for PCT/EP2009/007 123, mailed 2008. O183009 A1 7/2008 Wehner et al. Jan. 29, 2010. 2008, 0214708 A1 9, 2008 Bauer et al. English Translation of the PCT International Preliminary Report on 3.283 A. 1 58 Stepal. Patentability PCT/EP2009/007 123 mailed May 19, 2011. 2011/0201732 A1 8, 2011 Hill et al. Montchamp; "Recent advances in phosphorus-carbon bond forma 2011/0201733 A1 8, 2011 Hill et al. tion: synthesis of H-phosphinic acid derivatives from hypophosphus 2011/0213052 A1 9, 2011 Hill et al. compounds” Journal of Organometallic Chemistry Elsevier-Sequoua 2011/0213059 A1 9, 2011 Hill et al. S.A. Lausanne, CH, vol. 690; pp. 2388-2406; XP004877374 (May 2011/0213060 A1 9/2011 Hill et al. 16, 2005). 2011/0213061 A1 9/2011 Hill et al. Sylvine Deprele et al. “Palladium-Catalyzed Hydrophosphinylation 2011/0213062 A1 9, 2011 Hill et al. »s 2011/0213078 A1 9, 2011 Hill et al. of Alkenes and Alkynes; Journal of the American Chemical Society, 2011/0213079 A1 9, 2011 Hill et al. American Chemical Society, Washington DC, US vol. 124, No.32 p. 2011/0213080 A1 9, 2011 Hill et al. 9387, XP002500862 (Jan. 1, 2002). 2011/0224339 A1 9, 2011 Hill et al. Bravo-Altamirano et al.: “A Novel Approach to Phosphinic Acids 2011/022434.0 A1 9, 2011 Hill et al. from Hypophosphorus Acid:” Tetrahedron Letters, Elsevier, 2011/0237720 A1 9, 2011 Hill et al. Amsterdam, NL vol. 48, No. 33, pp. 5755-5759, XP022163552 (Jul. 2011/0237721 A1 9, 2011 Hill et al. 19, 2007). 2011/0237722 A1 9, 2011 Hill et al. Sylvine Deprele et al.: “Environmentally Benign Synthesis of 2011/0245385 A1 10, 2011 Hill et al. H-Phosphinic Acids. Using a Water Tolerant, Recyclable Polymer 2011/0245386 A1 10, 2011 Hill et al. Supported Catalyst.” Organic Letters, American Chemical Society, 2011/025 1310 Al 10/2011 Hill et al. US, vol. 6, No. 21, pp. 3805-3808 XP002500861 (Jan. 1, 2004). 2011/0251312 A1 10, 2011 Hill et al. Patrice Ribiere et al: "NiCL2-Catalyzed Hydrophosphinylation.” 2011/02757442011/0251315 A1 11,10, 2011 Hill et al. Journal 1 of OrganicO ic Chemistry,Chemistry. AmeriAmerican Chemical Society,Soci EastEaston, 2011/0281983 A1 11, 2011 Hill et al. US, vol. 70, No. 10, pp. 4064-4072, XP002530191 (Jan. 1, 2005). 2012,0064790 A1 3/2012 Bauer et al. Courdray L. et al.:"Allylic Phosphinates via Pd-Catalyzed Allylation of H-Phosphinic Acids with Allylic Alcohols;” Organic letters, vol. 10, No. 6, pp. 1123-1126 XP002561368 (Feb. 21, 2008). FOREIGN PATENT DOCUMENTS MastalerZ: Synthesis of some ethylene-(PP-Dialkyl)-Diphosphic Acids as new Potential Antimetabolites of Succinic Acid; Roczniki RE 2: 32; Chemii Ann.
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