CA2343456A1 - Novel phosphonium phosphinate compounds and their methods of preparation - Google Patents
Novel phosphonium phosphinate compounds and their methods of preparation Download PDFInfo
- Publication number
- CA2343456A1 CA2343456A1 CA002343456A CA2343456A CA2343456A1 CA 2343456 A1 CA2343456 A1 CA 2343456A1 CA 002343456 A CA002343456 A CA 002343456A CA 2343456 A CA2343456 A CA 2343456A CA 2343456 A1 CA2343456 A1 CA 2343456A1
- Authority
- CA
- Canada
- Prior art keywords
- phosphonium
- tetradecyl
- trihexyl
- compound
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- SZGFTJKRZLDFRR-UHFFFAOYSA-N [PH4+].[O-][PH2]=O Chemical class [PH4+].[O-][PH2]=O SZGFTJKRZLDFRR-UHFFFAOYSA-N 0.000 title abstract description 35
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
- 239000002904 solvent Substances 0.000 claims description 32
- -1 n-tetradecyl Chemical group 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000002608 ionic liquid Substances 0.000 abstract description 41
- 150000004714 phosphonium salts Chemical class 0.000 abstract description 6
- 239000002798 polar solvent Substances 0.000 abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 18
- 239000012071 phase Substances 0.000 description 18
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 16
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 16
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 16
- 239000008346 aqueous phase Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 12
- JCQGIZYNVAZYOH-UHFFFAOYSA-M trihexyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC JCQGIZYNVAZYOH-UHFFFAOYSA-M 0.000 description 12
- 235000010290 biphenyl Nutrition 0.000 description 11
- 239000004305 biphenyl Substances 0.000 description 11
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 11
- HQIPXXNWLGIFAY-UHFFFAOYSA-M decanoate;trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC HQIPXXNWLGIFAY-UHFFFAOYSA-M 0.000 description 10
- 238000009815 homocoupling reaction Methods 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000002411 thermogravimetry Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- XPYRLSOSTBBOGC-UHFFFAOYSA-M dicyclohexylphosphinate;trihexyl(tetradecyl)phosphanium Chemical compound C1CCCCC1P(=O)([O-])C1CCCCC1.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC XPYRLSOSTBBOGC-UHFFFAOYSA-M 0.000 description 8
- GJEGLSXURCDNRF-UHFFFAOYSA-M trifluoromethanesulfonate;trihexyl(tetradecyl)phosphanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC GJEGLSXURCDNRF-UHFFFAOYSA-M 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000005191 phase separation Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- ZKQLVOZSJHOZBL-UHFFFAOYSA-M bis(2,4,4-trimethylpentyl)phosphinate;trihexyl(tetradecyl)phosphanium Chemical compound CC(C)(C)CC(C)CP([O-])(=O)CC(C)CC(C)(C)C.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC ZKQLVOZSJHOZBL-UHFFFAOYSA-M 0.000 description 6
- OVJFGYWYBOKNNF-UHFFFAOYSA-M bis(2-methylpropyl)phosphinate;trihexyl(tetradecyl)phosphanium Chemical compound CC(C)CP([O-])(=O)CC(C)C.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC OVJFGYWYBOKNNF-UHFFFAOYSA-M 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- QUXFOKCUIZCKGS-UHFFFAOYSA-N bis(2,4,4-trimethylpentyl)phosphinic acid Chemical compound CC(C)(C)CC(C)CP(O)(=O)CC(C)CC(C)(C)C QUXFOKCUIZCKGS-UHFFFAOYSA-N 0.000 description 5
- 238000005810 carbonylation reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 5
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 150000005347 biaryls Chemical class 0.000 description 4
- 230000006315 carbonylation Effects 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- AGRZMISFMOWGQL-UHFFFAOYSA-M bis(2-methylpropyl)-sulfanylidene-sulfido-$l^{5}-phosphane;trihexyl(tetradecyl)phosphanium Chemical compound CC(C)CP([S-])(=S)CC(C)C.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC AGRZMISFMOWGQL-UHFFFAOYSA-M 0.000 description 3
- DRDKFCAHTAHYER-UHFFFAOYSA-N bis(2-methylpropyl)phosphinic acid Chemical compound CC(C)CP(O)(=O)CC(C)C DRDKFCAHTAHYER-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- OJNSBQOHIIYIQN-UHFFFAOYSA-M sodium;bis(2-methylpropyl)-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Na+].CC(C)CP([S-])(=S)CC(C)C OJNSBQOHIIYIQN-UHFFFAOYSA-M 0.000 description 3
- IVHVNMLJNASKHW-UHFFFAOYSA-M Chlorphonium chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC1=CC=C(Cl)C=C1Cl IVHVNMLJNASKHW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- QUXFOKCUIZCKGS-UHFFFAOYSA-M bis(2,4,4-trimethylpentyl)phosphinate Chemical compound CC(C)(C)CC(C)CP([O-])(=O)CC(C)CC(C)(C)C QUXFOKCUIZCKGS-UHFFFAOYSA-M 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ILYLJTAIQODOTI-UHFFFAOYSA-N cyclohexylphosphinic acid Chemical compound OP(=O)C1CCCCC1 ILYLJTAIQODOTI-UHFFFAOYSA-N 0.000 description 2
- NPEWVJINTXPNRF-UHFFFAOYSA-N dicyclohexylphosphinic acid Chemical compound C1CCCCC1P(=O)(O)C1CCCCC1 NPEWVJINTXPNRF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004679 31P NMR spectroscopy Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- XJTXBUKLGQCZHC-UHFFFAOYSA-N Steganacin Natural products C1=C2C=3C(OC)=C(OC)C(OC)=CC=3CC3C(=O)OCC3C(OC(C)=O)C2=CC2=C1OCO2 XJTXBUKLGQCZHC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- CZAVUHAYANOAQJ-UHFFFAOYSA-N [PH4+].[O-][PH2]=S Chemical class [PH4+].[O-][PH2]=S CZAVUHAYANOAQJ-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- PTZADPBANVYSTR-UHFFFAOYSA-N bis(2-methylpropyl)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)CP(S)(=S)CC(C)C PTZADPBANVYSTR-UHFFFAOYSA-N 0.000 description 1
- LIBORZSZYLFBQN-UHFFFAOYSA-L bis(2-methylpropyl)phosphinate trihexyl(tetradecyl)phosphanium Chemical compound C(C(C)C)P([O-])(=O)CC(C)C.C(CCCCC)[P+](CCCCCCCCCCCCCC)(CCCCCC)CCCCCC.C(C(C)C)P([O-])(=O)CC(C)C.C(CCCCC)[P+](CCCCCCCCCCCCCC)(CCCCCC)CCCCCC LIBORZSZYLFBQN-UHFFFAOYSA-L 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UFAPWKAOPUPYRD-UHFFFAOYSA-L dicyclohexylphosphinate trihexyl(tetradecyl)phosphanium Chemical compound C1(CCCCC1)P([O-])(=O)C1CCCCC1.C(CCCCC)[P+](CCCCCCCCCCCCCC)(CCCCCC)CCCCCC.C1(CCCCC1)P([O-])(=O)C1CCCCC1.C(CCCCC)[P+](CCCCCCCCCCCCCC)(CCCCCC)CCCCCC UFAPWKAOPUPYRD-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical compound O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XJTXBUKLGQCZHC-GCKMJXCFSA-N steganacin Chemical compound C1=C2C=3C(OC)=C(OC)C(OC)=CC=3C[C@@H]3C(=O)OC[C@H]3[C@H](OC(C)=O)C2=CC2=C1OCO2 XJTXBUKLGQCZHC-GCKMJXCFSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
- C07B37/04—Substitution
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002343456A CA2343456A1 (en) | 2001-03-30 | 2001-03-30 | Novel phosphonium phosphinate compounds and their methods of preparation |
| US10/473,271 US20040106823A1 (en) | 2001-03-30 | 2002-02-28 | Novel phosphonium phosphinate compounds and their methods of preparation |
| RU2003131897/04A RU2003131897A (ru) | 2001-03-30 | 2002-02-28 | Соединения фосфония фосфината и их получения |
| EP02707923A EP1373280A1 (en) | 2001-03-30 | 2002-02-28 | Phosphonium phosphinate compounds and their preparation |
| BR0208199-7A BR0208199A (pt) | 2001-03-30 | 2002-02-28 | Composto, método para preparar um composto de fosfinato de fosfÈnio, e, uso do composto |
| PCT/US2002/006104 WO2002079212A1 (en) | 2001-03-30 | 2002-02-28 | Phosphonium phosphinate compounds and their preparation |
| CNB028074505A CN1297560C (zh) | 2001-03-30 | 2002-02-28 | 次膦酸鏻化合物及其制备 |
| KR10-2003-7012520A KR20030093282A (ko) | 2001-03-30 | 2002-02-28 | 포스포늄 포스피네이트 화합물 및 이의 제법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002343456A CA2343456A1 (en) | 2001-03-30 | 2001-03-30 | Novel phosphonium phosphinate compounds and their methods of preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2343456A1 true CA2343456A1 (en) | 2002-09-30 |
Family
ID=4168780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002343456A Abandoned CA2343456A1 (en) | 2001-03-30 | 2001-03-30 | Novel phosphonium phosphinate compounds and their methods of preparation |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1373280A1 (ru) |
| KR (1) | KR20030093282A (ru) |
| CN (1) | CN1297560C (ru) |
| BR (1) | BR0208199A (ru) |
| CA (1) | CA2343456A1 (ru) |
| RU (1) | RU2003131897A (ru) |
| WO (1) | WO2002079212A1 (ru) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006007703A1 (en) * | 2004-07-16 | 2006-01-26 | Simon Fraser University | Phosphonium ionic liquids as recyclable solvents for solution phase chemistry |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2598156C (en) * | 2002-08-16 | 2011-02-08 | Cytec Canada Inc. | Phosphonium and imidazolium salts and methods of their preparation |
| CA2424215C (en) * | 2003-03-31 | 2008-11-18 | Cytec Canada Inc. | Phosphonium salts and methods of their preparation |
| DK1658262T3 (da) | 2003-08-27 | 2013-05-13 | Proionic Production Of Ionic Substances Gmbh & Co Kg | Fremgangsmåde til fremstilling af ioniske væsker, ioniske faste stoffer eller blandinger deraf |
| US20070129568A1 (en) * | 2005-12-06 | 2007-06-07 | Ngimat, Co. | Ionic liquids |
| US8375768B2 (en) | 2006-03-30 | 2013-02-19 | Oakland University | Ionic liquid thin layer sensor for electrochemical and/or piezoelectric measurements |
| US7886577B2 (en) * | 2006-03-30 | 2011-02-15 | Oakland University | Devices with surface bound ionic liquids and method of use thereof |
| EP1970432A1 (en) * | 2006-12-19 | 2008-09-17 | Castrol Limited | Lubricating oil compositions and uses |
| EP3233871B1 (en) * | 2014-12-19 | 2020-04-01 | Eastman Chemical Company | Quaternary phosphinates with co-solvents for extracting c1 to c4 carboxylic acids from aqueous streams |
| US9611209B1 (en) | 2015-12-18 | 2017-04-04 | Eastman Chemical Company | Quaternary arylcarboxylate compositions for extracting C1 to C4 carboxylic acids from aqueous streams |
| EP3470444A1 (de) | 2017-10-13 | 2019-04-17 | Basf Se | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung |
| CN108767314A (zh) * | 2018-04-16 | 2018-11-06 | 兰州大学 | 一种阻燃离子液体的制备及应用方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1442581A (en) * | 1975-01-28 | 1976-07-14 | Du Pont | Antistatic filaments |
| CA2308896A1 (en) * | 2000-05-18 | 2001-11-18 | Allan James Robertson | Phosphonium salts |
-
2001
- 2001-03-30 CA CA002343456A patent/CA2343456A1/en not_active Abandoned
-
2002
- 2002-02-28 WO PCT/US2002/006104 patent/WO2002079212A1/en not_active Application Discontinuation
- 2002-02-28 BR BR0208199-7A patent/BR0208199A/pt not_active Application Discontinuation
- 2002-02-28 RU RU2003131897/04A patent/RU2003131897A/ru not_active Application Discontinuation
- 2002-02-28 KR KR10-2003-7012520A patent/KR20030093282A/ko not_active Application Discontinuation
- 2002-02-28 EP EP02707923A patent/EP1373280A1/en not_active Withdrawn
- 2002-02-28 CN CNB028074505A patent/CN1297560C/zh not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006007703A1 (en) * | 2004-07-16 | 2006-01-26 | Simon Fraser University | Phosphonium ionic liquids as recyclable solvents for solution phase chemistry |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2003131897A (ru) | 2005-01-10 |
| WO2002079212A1 (en) | 2002-10-10 |
| EP1373280A1 (en) | 2004-01-02 |
| KR20030093282A (ko) | 2003-12-06 |
| CN1529708A (zh) | 2004-09-15 |
| BR0208199A (pt) | 2004-03-02 |
| CN1297560C (zh) | 2007-01-31 |
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