JP2018515535A5 - - Google Patents
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- JP2018515535A5 JP2018515535A5 JP2017559352A JP2017559352A JP2018515535A5 JP 2018515535 A5 JP2018515535 A5 JP 2018515535A5 JP 2017559352 A JP2017559352 A JP 2017559352A JP 2017559352 A JP2017559352 A JP 2017559352A JP 2018515535 A5 JP2018515535 A5 JP 2018515535A5
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 31
- 229910052698 phosphorus Inorganic materials 0.000 description 24
- 239000003446 ligand Substances 0.000 description 23
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 22
- 150000004703 alkoxides Chemical class 0.000 description 20
- 229910052799 carbon Inorganic materials 0.000 description 19
- 239000007791 liquid phase Substances 0.000 description 19
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 16
- 230000021523 carboxylation Effects 0.000 description 15
- 238000006473 carboxylation reaction Methods 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- 150000001721 carbon Chemical group 0.000 description 14
- 125000004429 atom Chemical group 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 13
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000001569 carbon dioxide Substances 0.000 description 11
- 229910002092 carbon dioxide Inorganic materials 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- -1 alkali metal salts Chemical class 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 125000004437 phosphorous atom Chemical group 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000002798 polar solvent Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 6
- 150000003624 transition metals Chemical class 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- NONFLFDSOSZQHR-CQOLUAMGSA-N d4-trimethyl silyl propionic acid Chemical compound OC(=O)C([2H])([2H])C([2H])([2H])[Si](C)(C)C NONFLFDSOSZQHR-CQOLUAMGSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000005191 phase separation Methods 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000001734 carboxylic acid salts Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000002452 interceptive effect Effects 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- HCBRTCFUVLYSKU-URFUVCHWSA-N (1r)-2-tert-butyl-1-[(1r)-2-tert-butyl-1,3-dihydroisophosphindol-1-yl]-1,3-dihydroisophosphindole Chemical compound CC(C)(C)P1CC2=CC=CC=C2[C@@H]1[C@H]1C2=CC=CC=C2CP1C(C)(C)C HCBRTCFUVLYSKU-URFUVCHWSA-N 0.000 description 1
- SJNUZTRUIDRSJK-KNCCTNLNSA-N (1s,2r)-1-tert-butyl-2-[(1s,2r)-1-tert-butylphospholan-2-yl]phospholane Chemical compound CC(C)(C)[P@]1CCC[C@@H]1[C@@H]1[P@@](C(C)(C)C)CCC1 SJNUZTRUIDRSJK-KNCCTNLNSA-N 0.000 description 1
- 125000006657 (C1-C10) hydrocarbyl group Chemical group 0.000 description 1
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- RMFRFTSSEHRKKW-UHFFFAOYSA-N 1,2-bis(diisopropylphosphino)ethane Chemical compound CC(C)P(C(C)C)CCP(C(C)C)C(C)C RMFRFTSSEHRKKW-UHFFFAOYSA-N 0.000 description 1
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- 125000003627 8 membered carbocyclic group Chemical group 0.000 description 1
- ADPVRCNXMMRNNI-UHFFFAOYSA-N C(=CCCCCCCCCCC)P(CCP(C=CCCCCCCCCCC)C=CCCCCCCCCCC)C=CCCCCCCCCCC Chemical compound C(=CCCCCCCCCCC)P(CCP(C=CCCCCCCCCCC)C=CCCCCCCCCCC)C=CCCCCCCCCCC ADPVRCNXMMRNNI-UHFFFAOYSA-N 0.000 description 1
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 description 1
- 101100189618 Caenorhabditis elegans pdi-2 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([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
- BOUYBUIVMHNXQB-UHFFFAOYSA-N dicyclohexyl(2-dicyclohexylphosphanylethyl)phosphane Chemical compound C1CCCCC1P(C1CCCCC1)CCP(C1CCCCC1)C1CCCCC1 BOUYBUIVMHNXQB-UHFFFAOYSA-N 0.000 description 1
- JBFJGFRJSFPTJL-UHFFFAOYSA-N dicyclopentyl(2-dicyclopentylphosphanylethyl)phosphane Chemical compound C1CCCC1P(C1CCCC1)CCP(C1CCCC1)C1CCCC1 JBFJGFRJSFPTJL-UHFFFAOYSA-N 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- MWVXFEZPEPOQRE-UHFFFAOYSA-N ditert-butyl(2-ditert-butylphosphanylethyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CCP(C(C)(C)C)C(C)(C)C MWVXFEZPEPOQRE-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940047670 sodium acrylate Drugs 0.000 description 1
- WUZZQZFCCNASOJ-UHFFFAOYSA-M sodium;2-fluorophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1F WUZZQZFCCNASOJ-UHFFFAOYSA-M 0.000 description 1
- YQGVYIMRLTVHSN-UHFFFAOYSA-M sodium;3-fluorophenolate Chemical compound [Na+].[O-]C1=CC=CC(F)=C1 YQGVYIMRLTVHSN-UHFFFAOYSA-M 0.000 description 1
- 239000004032 superbase Substances 0.000 description 1
- 150000007525 superbases Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15167626 | 2015-05-13 | ||
| EP15167626.9 | 2015-05-13 | ||
| PCT/EP2016/060328 WO2016180775A1 (en) | 2015-05-13 | 2016-05-09 | Process for preparing an unsaturated carboxylic acid salt |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018515535A JP2018515535A (ja) | 2018-06-14 |
| JP2018515535A5 true JP2018515535A5 (enExample) | 2019-06-13 |
| JP6808649B2 JP6808649B2 (ja) | 2021-01-06 |
Family
ID=53177201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017559352A Active JP6808649B2 (ja) | 2015-05-13 | 2016-05-09 | 不飽和カルボン酸塩の製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10138196B2 (enExample) |
| EP (1) | EP3294701B1 (enExample) |
| JP (1) | JP6808649B2 (enExample) |
| KR (1) | KR20180008621A (enExample) |
| CN (1) | CN107580593B (enExample) |
| WO (1) | WO2016180775A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9725393B2 (en) | 2014-10-08 | 2017-08-08 | Chevron Phillips Chemical Company Lp | Methods for the production of α,β-unsaturated carboxylic acids and salts thereof |
| US10160711B2 (en) | 2015-12-15 | 2018-12-25 | Chevron Phillips Chemical Company Lp | Formation of α,β-unsaturated carboxylic acids and salts thereof from metalalactones and anionic polyelectrolytes |
| US10618873B2 (en) | 2016-02-01 | 2020-04-14 | Basf Se | Method for producing C4-C15 lactams |
| US10544080B2 (en) | 2017-06-14 | 2020-01-28 | Chevron Phillips Chemical Company Lp | Continuous process for the conversion of olefins and carbon dioxide to acrylates via solution phase reactor |
| US10550061B2 (en) | 2017-06-14 | 2020-02-04 | Chevron Phillips Chemical Company Lp | Sulfur oxoacid-substituted and phosphorus oxoacid-substituted polyaromatic resins and salts thereof as promoters in acrylate production from coupling reactions of olefins and carbon dioxide |
| WO2019053541A1 (en) | 2017-09-14 | 2019-03-21 | Sabic Global Technologies B.V. | ACRYLATES BY OLEFIN COUPLING / CARBON DIOXIDE |
| EP3732175B1 (en) * | 2017-12-25 | 2023-08-16 | PTT Global Chemical Public Company Limited | A catalyst composition for a producing process of an unsaturated carboxylic acid salt and its derivatives from carbon dioxide and olefin |
| JPWO2019188507A1 (ja) * | 2018-03-28 | 2021-03-18 | 積水化学工業株式会社 | α，β−不飽和カルボン酸塩の製造方法 |
| US11174213B2 (en) | 2018-10-12 | 2021-11-16 | Chevron Phillips Chemical Company, Lp | Effects of catalyst concentration and solid activator on nickel-mediated olefin/carbon dioxide coupling to acrylates |
| WO2021185879A1 (en) | 2020-03-20 | 2021-09-23 | Basf Se | CATALYTIC PROCESS FOR PREPARING AN α,β-ETHYLENICALLY UNSATURATED CARBOXYLIC ACID SALT |
| US12162829B2 (en) | 2021-12-16 | 2024-12-10 | Chevron Phillips Chemical Company Lp | Gas phase process for acrylate production from ethylene and carbon dioxide |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE968903C (de) | 1952-05-13 | 1958-04-10 | Huels Chemische Werke Ag | Verfahren zur kontinuierlichen Herstellung von Alkalialkoholaten |
| US4792620A (en) * | 1983-10-14 | 1988-12-20 | Bp Chemicals Limited | Carbonylation catalysts |
| DE59906877D1 (de) * | 1998-06-12 | 2003-10-09 | Basf Ag | Verfahren zur herstellung von alkalimetallalkoholaten |
| US8642803B2 (en) | 2010-03-03 | 2014-02-04 | Basf Se | Preparation of ethylenically unsaturated carboxylic salts by carboxylation of alkenes |
| WO2013098772A1 (en) | 2011-12-29 | 2013-07-04 | Basf Se | PREPARATION OF α,β-ETHYLENICALLY UNSATURATED CARBOXYLIC SALTS BY CATALYTIC CARBOXYLATION OF ALKENES |
-
2016
- 2016-05-09 EP EP16722636.4A patent/EP3294701B1/en active Active
- 2016-05-09 WO PCT/EP2016/060328 patent/WO2016180775A1/en not_active Ceased
- 2016-05-09 JP JP2017559352A patent/JP6808649B2/ja active Active
- 2016-05-09 US US15/573,276 patent/US10138196B2/en active Active
- 2016-05-09 CN CN201680027140.5A patent/CN107580593B/zh active Active
- 2016-05-09 KR KR1020177035937A patent/KR20180008621A/ko not_active Withdrawn
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