RU2016149428A - Способ получения соли ненасыщенной карбоновой кислоты - Google Patents
Способ получения соли ненасыщенной карбоновой кислоты Download PDFInfo
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- RU2016149428A RU2016149428A RU2016149428A RU2016149428A RU2016149428A RU 2016149428 A RU2016149428 A RU 2016149428A RU 2016149428 A RU2016149428 A RU 2016149428A RU 2016149428 A RU2016149428 A RU 2016149428A RU 2016149428 A RU2016149428 A RU 2016149428A
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- sodium
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- 150000003839 salts Chemical class 0.000 title claims 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 230000003197 catalytic effect Effects 0.000 claims 20
- 238000000034 method Methods 0.000 claims 19
- 125000004432 carbon atom Chemical group C* 0.000 claims 11
- 239000003446 ligand Substances 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 229910052698 phosphorus Inorganic materials 0.000 claims 5
- 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 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 4
- 150000001735 carboxylic acids Chemical class 0.000 claims 4
- 239000007791 liquid phase Substances 0.000 claims 4
- 150000001336 alkenes Chemical class 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 230000021523 carboxylation Effects 0.000 claims 3
- 238000006473 carboxylation reaction Methods 0.000 claims 3
- 150000001734 carboxylic acid salts Chemical class 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 125000004437 phosphorous atom Chemical group 0.000 claims 3
- 239000012429 reaction media Substances 0.000 claims 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 2
- 239000001569 carbon dioxide Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- UGPKJFUWKPOBIQ-UHFFFAOYSA-M sodium;2,6-dimethylphenolate Chemical group [Na+].CC1=CC=CC(C)=C1[O-] UGPKJFUWKPOBIQ-UHFFFAOYSA-M 0.000 claims 2
- 229910052723 transition metal Inorganic materials 0.000 claims 2
- 150000003624 transition metals Chemical class 0.000 claims 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- BFZOTKYPSZSDEV-UHFFFAOYSA-N 4-butan-2-yl-2,6-ditert-butylphenol Chemical compound CCC(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BFZOTKYPSZSDEV-UHFFFAOYSA-N 0.000 claims 1
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 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 claims 1
- 150000005690 diesters Chemical class 0.000 claims 1
- -1 ethylene, ethenylene, 1,2-phenylene Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 238000005191 phase separation Methods 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- UWBSYPQUGZLORA-UHFFFAOYSA-M sodium 2-tert-butyl-6-methylphenolate Chemical compound [Na+].CC1=C([O-])C(=CC=C1)C(C)(C)C UWBSYPQUGZLORA-UHFFFAOYSA-M 0.000 claims 1
- SOAKNXMTFUXRJI-UHFFFAOYSA-M sodium;2,4,6-trimethylphenolate Chemical compound [Na+].CC1=CC(C)=C([O-])C(C)=C1 SOAKNXMTFUXRJI-UHFFFAOYSA-M 0.000 claims 1
- WYHABHVOLSCIOQ-UHFFFAOYSA-M sodium;2,4,6-tritert-butylphenolate Chemical compound [Na+].CC(C)(C)C1=CC(C(C)(C)C)=C([O-])C(C(C)(C)C)=C1 WYHABHVOLSCIOQ-UHFFFAOYSA-M 0.000 claims 1
- MMIGMVBXZUIMCT-UHFFFAOYSA-M sodium;2,6-di(propan-2-yl)phenolate Chemical compound [Na+].CC(C)C1=CC=CC(C(C)C)=C1[O-] MMIGMVBXZUIMCT-UHFFFAOYSA-M 0.000 claims 1
- AOIQNBCUUALSSZ-UHFFFAOYSA-M sodium;2,6-ditert-butyl-4-methylphenolate Chemical compound [Na+].CC1=CC(C(C)(C)C)=C([O-])C(C(C)(C)C)=C1 AOIQNBCUUALSSZ-UHFFFAOYSA-M 0.000 claims 1
- XFMBKGCZPCVSIE-UHFFFAOYSA-M sodium;2,6-ditert-butylphenolate Chemical compound [Na+].CC(C)(C)C1=CC=CC(C(C)(C)C)=C1[O-] XFMBKGCZPCVSIE-UHFFFAOYSA-M 0.000 claims 1
- GQFIWFPBDXSASA-UHFFFAOYSA-M sodium;2-chlorophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1Cl GQFIWFPBDXSASA-UHFFFAOYSA-M 0.000 claims 1
- WUZZQZFCCNASOJ-UHFFFAOYSA-M sodium;2-fluorophenolate Chemical group [Na+].[O-]C1=CC=CC=C1F WUZZQZFCCNASOJ-UHFFFAOYSA-M 0.000 claims 1
- JWYMWHGENDPLFG-UHFFFAOYSA-M sodium;3-chlorophenolate Chemical compound [Na+].[O-]C1=CC=CC(Cl)=C1 JWYMWHGENDPLFG-UHFFFAOYSA-M 0.000 claims 1
- YQGVYIMRLTVHSN-UHFFFAOYSA-M sodium;3-fluorophenolate Chemical compound [Na+].[O-]C1=CC=CC(F)=C1 YQGVYIMRLTVHSN-UHFFFAOYSA-M 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
- B01J31/2428—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom
- B01J31/2433—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
- B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
- B01J31/2471—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring with more than one complexing phosphine-P atom
- B01J31/2476—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
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Claims (61)
1. Каталитический способ получения соли α,β-этиленненасыщенной карбоновой кислоты, включающий
реакцию алкена и диоксида углерода в присутствии катализатора карбоксилирования и высвобождение соли α,β-этиленненасыщенной карбоновой кислоты с основанием, причем катализатор карбоксилирования представляет собой комплекс переходного металла, который содержит структурно затрудненный бидентатный Р,Х лиганд, где X выбирают из группы, состоящей из Р, N, О и карбена, причем Р и X атомы разделены 2-4 мостиковыми атомами, и где мостиковые атомы являются частью по меньшей мере одной 5-7-членной циклической подструктуры.
2. Каталитический способ по п. 1, в котором указанный структурно затрудненный бидентатный Р,Х лиганд представляет собой Р,Р лиганд,
причем каждый мостиковый атом, непосредственно связанный с Р атомом, вместе с Р атомом, с которым он связан, является частью 5-7-членной циклической подструктуры;
или
причем два соседних мостиковых атома являются частью 5-7-членной циклической подструктуры.
3. Каталитический способ по п. 1, в котором структурно затрудненный бидентатный фосфор-содержащий лиганд выбирают из лигандов формулы (IIa)
в которой
R6 независимо выбирают из CHR7 2, CR7 3 и С3-С8-циклоалкила,
R7 независимо выбирают из линейного С1-С4-алкила,
А1 вместе с атомами углерода, с которыми она связана, и
промежуточным атомом фосфора образует 5-7-членную циклическую подструктуру, и
R8 независимо выбирают из водорода, С1-С12-алкила, С3-С12-циклоалкила, С3-С12-гетероциклоалкила, С6-С14-арила, С6-С14-гетероарила, С1-С12-алкокси, С3-С12-циклоалкокси, С3-С12-гетероциклоалкокси, С6-С14-арилокси и С6-С14-гетероарилокси,
формулы (IIb)
в которой
R10 независимо выбирают из C1-C8-алкила и С3-С8-циклоалкила,
R11 независимо выбирают из CHR10 2, CR10 3 и С3-С8-циклоалкила,
X независимо выбирают из С-Н, С-СН3 и N, и
А2 вместе с составляющими X, с которыми она связана, и промежуточными атомами углерода образует 5-7-членную циклическую подструктуру,
и формулы (IIc)
в которой
R13 и R14 независимо выбирают из С3-С8-циклоалкила, и
R15 представляет собой Н, O-C1-С6-алкил, или оба R15 вместе составляют -СН=СН- мостик.
4. Каталитический способ по п. 3, в котором в формуле (IIa) R6 представляет собой CR7 3.
5. Каталитический способ по п. 3, в котором в формуле (IIa), А1 выбирают из этилена, этенилена, 1,2-фенилена, 1,2-нафтилена, 2,3-нафтилена и следующих формул:
6. Каталитический способ по п. 3, в котором в формуле (IIb), каждый R10 независимо выбирают из C1-С6-алкила и С3-С7-циклоалкила, и R11 представляет собой CR10 3.
7. Каталитический способ по п. 3, в котором в формуле (IIb), А2 представляет собой -СН=СН- мостик.
8. Каталитический способ по п. 3, в котором в формуле (IIc), R15 представляет собой Н или ОСН3.
9. Каталитический способ по п. 3, в котором в формуле (IIb), X представляет собой СН.
10. Каталитический способ по п. 1, в котором структурно затрудненный бидентатный фосфор-содержащий лиганд выбирают из
где Су представляет собой циклогексил.
11. Каталитический способ по п. 1, в котором комплекс переходного металла представляет собой комплекс никеля.
12. Каталитический способ по п. 1, в котором алкен представляет собой этен, и α,β-этиленненасыщенная карбоновая кислота карбоновая кислота представляет собой акриловую кислоту.
13. Каталитический способ по п. 1, в котором алкен и диоксид углерода реагируют в присутствии восстановителя.
14. Каталитический способ по п. 1, в котором реакционная среда содержит апротонный органический растворитель.
15. Каталитический способ по п. 14, где апротонный органический растворитель выбирают из
- циклических алкиловых простых эфиров с 4-8 атомами углерода,
- диалкиловых простых эфиров с 2-12 атомами углерода,
- циклоалкилалкиловых простых эфиров с 4-12 атомами углерода,
- арилалкиловых простых эфиров с 7-16 атомами углерода,
- биарилов с 12-16 атомами углерода,
- диарилоксидов с 12-16 атомами углерода,
- C1-C8-алкиловых сложных эфиров С6-С10-арилмонокарбоновых кислот,
- ди-С1-С8-алкиловых сложных эфиров С6-С10-арилдикарбоновых кислот,
- диалкилкарбонатов с 3-13 атомами углерода,
простых диэфиров, состоящих из диоксиалкиленового остатка с 2-8 атомами углерода и двух C1-C8-алкильных остатков,
- бензолов, в которых 1-4 атомов водорода замещены 1-4 С1-С4-алкильными остатками,
- галогенированных бензолов,
- алканов с 5-18 атомами углерода, и их смесей.
16. Каталитический способ по п. 1, в котором основание выбирают из арилоксидов.
17. Каталитический способ по п. 16, в котором арилоксид выбирают из 2-фторфенолята натрия, 3-фторфенолята натрия, 2-хлорфенолята натрия и 3-хлорфенолята натрия.
18. Каталитический способ по п. 16, в котором арилоксид выбирают из 2,6-диметилфенолята натрия, 2,6-диизопропилфенолята натрия, 2-метил-6-трет.-бутилфенолята натрия, 2,6-ди-трет.-бутилфеноксида натрия, 2,6-диметилфенолята натрия, 2,6-диметил-4-трет.-бутилфенолята натрия, 2,4,6-триметилфенолята натрия, 2,6-ди-трет.-бутил-4-метилфенолята натрия, 2,6-ди-трет.-бутил-4-втор.-бутилфенолята и 2,4,6-три-трет.-бутилфенолята натрия.
19. Каталитический способ по п. 1, в котором соль α,β-этиленненасыщенной карбоновой кислоты удаляют из реакционной среды, причем указанное удаление соли α,β-этиленненасыщенной карбоновой кислоты из реакционной среды включает фазовое разделение типа жидкость-жидкость на первую жидкую фазу, которая обогащена солью α,β-этиленненасыщенной карбоновой кислоты, и вторую жидкую фазу, которая обогащена катализатором карбоксилирования, основанием и сопряженной с основанием кислотой, где первую и вторую жидкие фазы получают путем приведения реакционной среды в контакт с полярным растворителем.
20. Каталитический способ по любому из пп. 16-19, включающий регенерацию арилоксида посредством добавления щелочного материала.
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| US9416087B2 (en) | 2014-10-08 | 2016-08-16 | Chevron Phillips Chemical Company Lp | Methods for the production of α,β-unsaturated carboxylic acids and salts thereof |
| 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 |
| RU2732326C2 (ru) | 2015-07-22 | 2020-09-15 | Басф Се | Способ получения фуран-2,5-дикарбоновой кислоты |
| US10259797B2 (en) | 2015-11-04 | 2019-04-16 | Basf Se | Process for preparing a mixture comprising 5-(hydroxymethyl) furfural and specific HMF esters |
| US10428039B2 (en) | 2015-11-04 | 2019-10-01 | Basf Se | Process for preparing furan-2,5-dicarboxylic acid |
| EP3170828A1 (de) | 2015-11-23 | 2017-05-24 | Basf Se | Verfahren zur herstellung von verbindungen mit 16-oxabicyclo[10.3.1]pentadecengerüst und deren folgeprodukten |
| CN113402375B (zh) | 2015-12-15 | 2024-04-02 | 切弗朗菲利浦化学公司 | 由金属内酯和阴离子聚电解质形成α,β-不饱和羧酸和其盐 |
| CN109071398B (zh) | 2016-04-06 | 2022-09-27 | 切弗朗菲利浦化学公司 | 产生α,β-不饱和羧酸和其盐的方法 |
| WO2017178282A1 (en) * | 2016-04-11 | 2017-10-19 | Basf Se | Process for preparing an unsaturated carboxylic acid salt |
| 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 |
| US20180362435A1 (en) * | 2017-06-14 | 2018-12-20 | Chevron Phillips Chemical Company Lp | High porosity aromatic resins as promoters in acrylate production from coupling reactions of olefins and carbon dioxide |
| 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 |
| CN111587246B (zh) | 2017-12-25 | 2023-05-26 | Ptt全球化学公共有限公司 | 一种用于得自二氧化碳和烯烃的不饱和羧酸盐及其衍生物的生产方法的催化剂组合物 |
| 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 |
| US12162829B2 (en) | 2021-12-16 | 2024-12-10 | Chevron Phillips Chemical Company Lp | Gas phase process for acrylate production from ethylene and carbon dioxide |
| CN114956979B (zh) * | 2022-06-06 | 2023-04-28 | 中国科学技术大学 | 一种甲苯合成苯乙酸的催化剂体系 |
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