JP6635948B2 - 不飽和カルボン酸塩を調製する方法 - Google Patents
不飽和カルボン酸塩を調製する方法 Download PDFInfo
- Publication number
- JP6635948B2 JP6635948B2 JP2016567978A JP2016567978A JP6635948B2 JP 6635948 B2 JP6635948 B2 JP 6635948B2 JP 2016567978 A JP2016567978 A JP 2016567978A JP 2016567978 A JP2016567978 A JP 2016567978A JP 6635948 B2 JP6635948 B2 JP 6635948B2
- Authority
- JP
- Japan
- Prior art keywords
- sodium
- alkyl
- carbon atoms
- catalytic method
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims description 75
- 150000007942 carboxylates Chemical class 0.000 title claims description 30
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 82
- -1 ethylene, ethenylene, 1,2-phenylene Chemical group 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 150000001336 alkenes Chemical class 0.000 claims description 53
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 48
- 239000007791 liquid phase Substances 0.000 claims description 44
- 239000001569 carbon dioxide Substances 0.000 claims description 41
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 41
- 230000021523 carboxylation Effects 0.000 claims description 40
- 238000006473 carboxylation reaction Methods 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 239000003446 ligand Substances 0.000 claims description 38
- 229910052698 phosphorus Inorganic materials 0.000 claims description 32
- 229910052723 transition metal Inorganic materials 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 29
- 230000003197 catalytic effect Effects 0.000 claims description 28
- 239000012429 reaction media Substances 0.000 claims description 28
- 150000003624 transition metals Chemical class 0.000 claims description 28
- 125000004429 atom Chemical group 0.000 claims description 26
- 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 description 25
- 239000003960 organic solvent Substances 0.000 claims description 22
- 239000002798 polar solvent Substances 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 238000005191 phase separation Methods 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 229910052759 nickel Inorganic materials 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000011734 sodium Substances 0.000 claims description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 13
- 230000036961 partial effect Effects 0.000 claims description 13
- 229910052708 sodium Inorganic materials 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000004437 phosphorous atom Chemical group 0.000 claims description 8
- 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 description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 230000001172 regenerating effect Effects 0.000 claims description 4
- UGPKJFUWKPOBIQ-UHFFFAOYSA-M sodium;2,6-dimethylphenolate Chemical group [Na+].CC1=CC=CC(C)=C1[O-] UGPKJFUWKPOBIQ-UHFFFAOYSA-M 0.000 claims description 4
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 3
- GQFIWFPBDXSASA-UHFFFAOYSA-M sodium;2-chlorophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1Cl GQFIWFPBDXSASA-UHFFFAOYSA-M 0.000 claims description 3
- WUZZQZFCCNASOJ-UHFFFAOYSA-M sodium;2-fluorophenolate Chemical group [Na+].[O-]C1=CC=CC=C1F WUZZQZFCCNASOJ-UHFFFAOYSA-M 0.000 claims description 3
- JWYMWHGENDPLFG-UHFFFAOYSA-M sodium;3-chlorophenolate Chemical compound [Na+].[O-]C1=CC=CC(Cl)=C1 JWYMWHGENDPLFG-UHFFFAOYSA-M 0.000 claims description 3
- YQGVYIMRLTVHSN-UHFFFAOYSA-M sodium;3-fluorophenolate Chemical compound [Na+].[O-]C1=CC=CC(F)=C1 YQGVYIMRLTVHSN-UHFFFAOYSA-M 0.000 claims description 3
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 150000001983 dialkylethers Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 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 description 2
- RCRTYTYLKJZPQL-UHFFFAOYSA-M sodium 4-butan-2-yl-2,6-ditert-butylphenolate Chemical compound C(C)(C)(C)C1=C([O-])C(=CC(=C1)C(C)CC)C(C)(C)C.[Na+] RCRTYTYLKJZPQL-UHFFFAOYSA-M 0.000 claims description 2
- HDXKVYIJMWDYTQ-UHFFFAOYSA-M sodium 4-tert-butyl-2,6-dimethylphenolate Chemical compound [Na+].CC1=CC(=CC(C)=C1[O-])C(C)(C)C HDXKVYIJMWDYTQ-UHFFFAOYSA-M 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
- NXXYKOUNUYWIHA-UHFFFAOYSA-M 2,6-dimethylphenolate Chemical compound CC1=CC=CC(C)=C1[O-] NXXYKOUNUYWIHA-UHFFFAOYSA-M 0.000 claims 1
- 125000005841 biaryl group Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 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
- 239000002585 base Substances 0.000 description 68
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 39
- 229910052783 alkali metal Inorganic materials 0.000 description 38
- 150000001340 alkali metals Chemical class 0.000 description 37
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 150000001342 alkaline earth metals Chemical class 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
- 239000007795 chemical reaction product Substances 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 150000004703 alkoxides Chemical group 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 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 5
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000011049 filling Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 150000004678 hydrides Chemical class 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 230000008929 regeneration Effects 0.000 description 5
- 238000011069 regeneration method Methods 0.000 description 5
- 229940047670 sodium acrylate Drugs 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 4
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000003627 8 membered carbocyclic group Chemical group 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- BARUNXKDFNLHEV-UHFFFAOYSA-N [3-diphenylphosphanyl-2-(diphenylphosphanylmethyl)-2-methylpropyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CC(CP(C=1C=CC=CC=1)C=1C=CC=CC=1)(C)CP(C=1C=CC=CC=1)C1=CC=CC=C1 BARUNXKDFNLHEV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000005347 biaryls Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000003950 cyclic amides Chemical class 0.000 description 2
- 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 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 150000004707 phenolate Chemical class 0.000 description 2
- 125000005538 phosphinite group Chemical group 0.000 description 2
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 2
- 150000008300 phosphoramidites Chemical class 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002577 pseudohalo group Chemical group 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- JRTIUDXYIUKIIE-KZUMESAESA-N (1z,5z)-cycloocta-1,5-diene;nickel Chemical compound [Ni].C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 JRTIUDXYIUKIIE-KZUMESAESA-N 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-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
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DJMUYABFXCIYSC-UHFFFAOYSA-N 1H-phosphole Chemical compound C=1C=CPC=1 DJMUYABFXCIYSC-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- BDDNYDPRCCDQQJ-UHFFFAOYSA-N 3'-(3-hydroxyphenyl)-4-methylspiro[1h-1,4-benzodiazepine-3,2'-oxirane]-2,5-dione Chemical compound CN1C(=O)C2=CC=CC=C2NC(=O)C11OC1C1=CC=CC(O)=C1 BDDNYDPRCCDQQJ-UHFFFAOYSA-N 0.000 description 1
- QRPNDOFSVHOGCK-UHFFFAOYSA-N 3-di(propan-2-yl)phosphanylpropyl-di(propan-2-yl)phosphane Chemical compound CC(C)P(C(C)C)CCCP(C(C)C)C(C)C QRPNDOFSVHOGCK-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- HRZSNESBRSONNG-UHFFFAOYSA-N 4-di(propan-2-yl)phosphanylbutyl-di(propan-2-yl)phosphane Chemical compound CC(C)P(C(C)C)CCCCP(C(C)C)C(C)C HRZSNESBRSONNG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VFEWYNYROHESJO-UHFFFAOYSA-N C(C)(C)P(C(C)C)C1(C=CC=C1)[Fe] Chemical compound C(C)(C)P(C(C)C)C1(C=CC=C1)[Fe] VFEWYNYROHESJO-UHFFFAOYSA-N 0.000 description 1
- GBLQNFPULYFTDK-UHFFFAOYSA-N C1(CCCCC1)P(C1CCCCC1)C1(C=CC=C1)[Fe] Chemical compound C1(CCCCC1)P(C1CCCCC1)C1(C=CC=C1)[Fe] GBLQNFPULYFTDK-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical group [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 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
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 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
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 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
- HLLUWVKDDQIKNF-UHFFFAOYSA-N [2-[2-di(propan-2-yl)phosphanyl-6-methoxyphenyl]-3-methoxyphenyl]-di(propan-2-yl)phosphane Chemical group COC1=CC=CC(P(C(C)C)C(C)C)=C1C1=C(OC)C=CC=C1P(C(C)C)C(C)C HLLUWVKDDQIKNF-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 229940048053 acrylate Drugs 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 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
- RSJBEKXKEUQLER-UHFFFAOYSA-N dicyclohexyl(3-dicyclohexylphosphanylpropyl)phosphane Chemical compound C1CCCCC1P(C1CCCCC1)CCCP(C1CCCCC1)C1CCCCC1 RSJBEKXKEUQLER-UHFFFAOYSA-N 0.000 description 1
- WNZGLXFLSFWPMP-UHFFFAOYSA-N dicyclohexyl(4-dicyclohexylphosphanylbutyl)phosphane Chemical compound C1CCCCC1P(C1CCCCC1)CCCCP(C1CCCCC1)C1CCCCC1 WNZGLXFLSFWPMP-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
- XNDWOYYSZZBBEJ-UHFFFAOYSA-N dicyclopentyl(3-dicyclopentylphosphanylpropyl)phosphane Chemical compound C1CCCC1P(C1CCCC1)CCCP(C1CCCC1)C1CCCC1 XNDWOYYSZZBBEJ-UHFFFAOYSA-N 0.000 description 1
- FUWRLRPUJPPSAO-UHFFFAOYSA-N dicyclopentyl(4-dicyclopentylphosphanylbutyl)phosphane Chemical compound C1CCCC1P(C1CCCC1)CCCCP(C1CCCC1)C1CCCC1 FUWRLRPUJPPSAO-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- NLHWCTNYFFIPJT-UHFFFAOYSA-N disodium bis(trimethylsilyl)azanide Chemical compound [Na+].[Na+].C[Si](C)(C)[N-][Si](C)(C)C.C[Si](C)(C)[N-][Si](C)(C)C NLHWCTNYFFIPJT-UHFFFAOYSA-N 0.000 description 1
- UIYGJYHQLCCIQS-UHFFFAOYSA-N ditert-butyl(4-ditert-butylphosphanylbutyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CCCCP(C(C)(C)C)C(C)(C)C UIYGJYHQLCCIQS-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 229910012375 magnesium hydride Inorganic materials 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 150000004857 phospholes Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- XMQSRWZOMVIXEG-UHFFFAOYSA-M sodium 2,6-difluorophenolate Chemical compound FC1=C(C(=CC=C1)F)[O-].[Na+] XMQSRWZOMVIXEG-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- ONFAAMBUOAGWSG-UHFFFAOYSA-M sodium;2-methylphenolate Chemical compound [Na+].CC1=CC=CC=C1[O-] ONFAAMBUOAGWSG-UHFFFAOYSA-M 0.000 description 1
- JYCDILBEUUCCQD-UHFFFAOYSA-N sodium;2-methylpropan-1-olate Chemical compound [Na+].CC(C)C[O-] JYCDILBEUUCCQD-UHFFFAOYSA-N 0.000 description 1
- CFPLEOLETMZLIB-UHFFFAOYSA-M sodium;4-chlorophenolate Chemical compound [Na+].[O-]C1=CC=C(Cl)C=C1 CFPLEOLETMZLIB-UHFFFAOYSA-M 0.000 description 1
- FENGEGUDMXHOBU-UHFFFAOYSA-M sodium;4-fluorophenolate Chemical compound [Na+].[O-]C1=CC=C(F)C=C1 FENGEGUDMXHOBU-UHFFFAOYSA-M 0.000 description 1
- ZBNNKSSSCSTNNK-UHFFFAOYSA-M sodium;naphthalen-1-olate Chemical compound [Na+].C1=CC=C2C([O-])=CC=CC2=C1 ZBNNKSSSCSTNNK-UHFFFAOYSA-M 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical class [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 238000010507 β-hydride elimination reaction Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
-
- 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
-
- 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
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
アルケン、及び二酸化炭素をカルボキシル化触媒の存在下で反応させる工程、並びにα,β−エチレン性不飽和カルボン酸塩を塩基によって放出する工程を含み、前記カルボキシル化触媒が、構造的に制約された二座P,X配位子を含む遷移金属錯体であり、上記中、Xは、P、N、O、及びカルベンからなる群から選択され、前記P、及びX原子は、2〜4個の架橋原子によって離され、且つ前記架橋原子は、少なくとも1個の5〜7員の環状部分構造の一部である方法を提供する。
Mは、遷移金属であり、
Lは、配位子であり、
qは、1、又は2であり、且つ
Ra、Rb、及びRcは、それぞれ独立して、水素、C1 〜C 12 アルキル、C2 〜C 12 アルケニルであるか、又はRa、及びRbは、それらが結合される炭素原子と一緒になった、モノ、若しくはジエチレン性不飽和の、5〜8員の炭素環である]
によって説明することができる。
R6は、CHR7 2、CR7 3、及びC3 〜C 8 シクロアルキルから独立して選択され、
R7は、直鎖C1−C4−アルキルから独立して選択され、
A1は、それが結合する炭素原子、及び介在するリン原子と一緒になって、5〜7員の環状部分構造を形成し、且つ
R8は、水素、C1 〜C 12 アルキル、C3 〜C 12 シクロアルキル、C 3 〜C 12 ヘテロシクロアルキル、C6 〜C 14 アリール、C6 〜C 14 ヘテロアリール、C1 〜C 12 アルコキシ、C 3 〜C 12 シクロアルコキシ、C3 〜C 12 ヘテロシクロアルコキシ、C6 〜C 14 アリールオキシ、及びC6 〜C 14 ヘテロアリールオキシから独立して選択される]、
である。
mは、2又は3であり、且つnは、1又は2である。
R10は、C1 〜C 8 アルキル、及びC3 〜C 8 シクロアルキルから独立して選択され、
R11は、CHR10 2、CR10 3、及びC 3 〜C 8 シクロアルキルから独立して選択され、
Xは、C−H、C−CH3、及びNから独立して選択され、且つ
A2は、それが結合する部分X、及び介在する炭素原子と一緒になって、5〜7員の環状部分構造を形成する]
の配位子である。
R13、及びR14は、C3 〜C8シクロアルキル、例えば、C5 〜C7シクロアルキルから独立して選択され、且つ
R15は、H、O−C1 〜C 6 アルキルであるか、又は両方のR15が一緒になって、−CH=CH−架橋を構成する]
の配位子である。
[式中、
Xは、ハロゲン化物、擬ハロゲン化物、カルボン酸塩、アルコキシド、炭酸塩、硫酸塩、硝酸塩、水酸化物、アセチルアセトネート、シクロペンタジエン、アルキル、及びアリールから選択され、且つ
Lは、ホスフィン、アミン、オレフィン、カルボニル、及びニトリル、
並びにエーテル、DMSO、又は水等の溶媒との対応する付加体から選択される中性配位子である]を含む。
Ra、Rb、及びRcは、それぞれ独立して、水素、C1 〜C 12 アルキル、C2 〜C 12 アルケニルであるか、又はRa、及びRbは、それらが結合される炭素原子と一緒になった、モノ、若しくはジエチレン性不飽和の、5〜8員の炭素環である]
のものである。
Rは、F、Cl、Br、I、C1 〜C 16 アルキル、C 3 〜C 16 シクロアルキル、及びC1 〜C 16 フルオロアルキルから選択され、2個の隣接するRは、F、Cl、Br、I、C1 〜C 16 アルキル、C3 〜C 16 シクロアルキル、及びC1 〜C 16 フルオロアルキルから独立して選択される1〜4個の置換基によって、任意に置換されるC3 〜C 5 ヒドロカルビレン架橋を構成してもよく、且つ
rは、1〜5から選択される整数であり、
最大でも2個のRが、Fである]
に対応するアリールオキシドであってもよい。
xは、0、1、又は2であり、
R2は、メチルであり、
R3は、独立してC1 〜C 16 アルキル、C3 〜C 16 シクロアルキルである]
の1式に対応してもよい。
Rは、C1 〜C 16 アルキル、及びC3 〜C 16 シクロアルキルから独立して選択され、
rは、2〜5から選択される整数であり、
且つ1個のRは、一般式(I)のフェニル環の2位で、別のRは6位である]
に対応する。これは、両方のRが、O-に対して、オルト位であることを意味する。
・4〜8個の炭素原子を有する環状アルキルエーテル、
・2〜12個の炭素原子を有するジアルキルエーテル、
・4〜12個の炭素原子を有するシクロアルキルアルキルエーテル、
・7〜16個の炭素原子を有するアリールアルキルエーテル、
・12〜16個の炭素原子を有するビアリール、
・12〜16個の炭素原子を有するジアリールオキシド
・C6 〜C 10 アリールモノカルボン酸のC1 〜C 8 アルキルエステル、
・C6 〜C 10 アリールジカルボン酸のジ−C1 〜C 8 アルキルエステル、
・3〜13個の炭素原子を有するジアルキルカーボネート、
・2〜8個の炭素原子を有するジオキシアルキレン残基、及びC1 〜C 8 アルキル残基からなるジエーテル、
・1〜4個の水素原子が、1〜4個のC1 〜C 4 アルキル残基に置換されたベンゼン、
・ハロゲン化ベンゼン、
・5〜18個の炭素原子を有するアルカン、
及びそれらの混合物
から選択される。
・7〜16個の炭素原子を有するアリールアルキルエーテル、
・12〜16個の炭素原子を有するビアリール、
・12〜16個の炭素原子を有するジアリールオキシド
・C 6 〜C 10 アリールモノカルボン酸のC1 〜C 8 アルキルエステル、
・C6 〜C 10 アリールジカルボン酸のジ−C1 〜C 8 アルキルエステル、
・1〜4個の水素原子が、1〜4個のC1 〜C 4 アルキル残基に置換されたベンゼン、
及びそれらの混合物;
から選択される。
・反応領域、例えば、カルボキシル化反応器中で実施する第一工程であり、
前記アルケン、例えば、エテン、及び二酸化炭素のカルボキシル化触媒の存在下での反応、並びに前記塩基による前記α,β−エチレン性不飽和カルボン酸塩の放出を、前記非プロトン性有機溶媒を含む反応媒体中で実施し、
・第二液相を、第二工程から再生利用し、前記アルケン、及び前記二酸化炭素を、前記反応領域中へ供給し、且つ
・粗反応生成物を、前記反応領域から排出する第一工程、並びに
・相分離領域、すなわち、液−液相分離器(separator)中で実施する第二工程であり、
・第一工程から得られる前記粗反応生成物を、前記相分離領域中へ供給し、
・前記α,β−エチレン性不飽和カルボン酸塩が濃縮された第一液相を、前記相分離領域から排出し、且つ
・前記カルボキシル化触媒、未反応のアリールオキシド、及び前記アリール水酸化物が、濃縮された第二液相を、前記相分離領域から排出し、前記第二液相によって含まれる前記極性溶媒の一部、又は全部、例えば水を除去して、又は前記極性溶媒のいずれも除去することなく、第一工程中へ再利用する第二工程
を含む連続的な方法であって、
前記第一液相、及び前記第二液相を得るために、前記粗反応生成物を、前記相分離領域中へ供給する前に、及び/又は前記相分離領域中へ供給する際に、前記極性溶媒と混合し、且つ
前記アルカリ性物質、例えば、水酸化ナトリウムを、前記反応領域から放出される前記粗反応生成物へ、及び/又は前記相分離領域中へ、及び/又は前記相分離領域から放出される第二液相中へ添加する方法である。
Ex. 例
NaHMDS ナトリウムビス(トリメチルシリル)アミド
NaOtBu ナトリウムtert−ブトキシド
NaOMe ナトリウムメトキシド
Ni(COD)2 ビス(シクロオクタジエン)ニッケル(0)
PhCl モノクロロベンゼン
THF テトラヒドロフラン
TON 遷移金属に関する転換数(turnover number)
dtbpe 1,2−ビス(ジ−tert−ブチルホスフィノ)エタン
dtbpb 1,4−ビス(ジ−tert−ブチルホスフィノ)ブタン
dcppe 1,2−ビス(ジシクロペンチルホスフィノ)エタン
dcppp 1,3−ビス(ジシクロペンチルホスフィノ)プロパン
dcppb 1,4−ビス(ジシクロペンチルホスフィノ)ブタン
dcpe 1,2−ビス(ジシクロヘキシルホスフィノ)エタン
dcpp 1,3−ビス(ジシクロヘキシルホスフィノ)プロパン
dcpb 1,4−ビス(ジシクロヘキシルホスフィノ)ブタン
diprpe 1,2−ビス(ジイソプロピルホスフィノ)エタン
diprpp 1,3−ビス(ジイソプロピルホスフィノ)プロパン
diprpb 1,4−ビス(ジイソプロピルホスフィノ)ブタン
Ferrocene−1 1―ジフェニルホスフィノ−2−ジフェニルホスフィノ−4−tert−ブチル−シクロペンタジエニル−1’−ジイソプロピルホスフィノ−3’−tert−ブチル−シクロペンタジエニル鉄
Ferrocene−2 1−ジフェニルホスフィノ−2−ジフェニルホスフィノ−4−tert−ブチル−シクロペンタジエニル−1’−ジフェニルホスフィノ−3’−tert−ブチル−シクロペンタジエニル鉄
Ferrocene−3 1,1’−ビス(ジイソプロピルホスフィノシクロペンタジエニル)鉄
Ferrocene−4 1,1’−ビス(ジシクロヘキシルホスフィノシクロペンタジエニル)鉄
iPr―MeOBIPHEP 2,2’−ビス(ジイソプロピルホスフィノ)−6,6’−ジメトキシ−1,1’−ビフェニル
Ph−BPE 1,2−ビス−((2R,5R)−ジフェニルホスホラノ)エタン
Triphos 1,1,1−トリス(ジフェニルホスフィノメチル)エタン
グローブボックス中で、表1〜8に示したように、30mLの溶媒、遷移金属源、配位子、塩基、任意にアルカリ性物質を、アルゴン雰囲気下で、両端でバルブによって密封可能な充填カートリッジ中へ移した。亜鉛(微細粉末、<10μm、Sigma Aldrich Cat. No.209988)を添加した際、それを直接オートクレーブ中に移した。
粗反応生成物から、水相中へ移行される塩基、及び強役酸の量について試験した。粗反応生成物によって含まれる非プロトン性有機溶媒(THF)、塩基、及び共役酸の量を、表8に示す。
Claims (19)
- アルケン、及び二酸化炭素をカルボキシル化触媒の存在下で反応させる工程、並びにα,β−エチレン性不飽和カルボン酸塩を塩基によって放出する工程を含み、前記カルボキシル化触媒が、構造的に制約された二座P,P配位子を含む遷移金属錯体であり、
前記P,P配位子のP原子は、2〜4個の架橋原子によって相互に離され、且つ前記架橋原子は、少なくとも1個の5〜7員の環状部分構造の一部である、α,β−エチレン性不飽和カルボン酸塩を調製する触媒的方法であって、
前記構造的に制約された二座P,P配位子が、
i)直接P原子に結合され、それが結合するP原子と一緒になって、5〜7員の環状部分構造の一部である各架橋原子を有するP,P配位子であるか、
又は
ii)5〜7員の環状部分構造の一部である2個の隣接する架橋原子を有するP,P配位子であり、
前記2〜4個の架橋原子が炭素原子である、触媒的方法。 - 前記構造的に制約された二座リン配位子が、
式(IIa)
R6は、CHR7 2、CR7 3、及びC3〜C8シクロアルキルから独立して選択され、
R7は、直鎖C1〜C4アルキルから独立して選択され、
A1は、それが結合する炭素原子、及び介在するリン原子と一緒になって、5〜7員の環状部分構造を形成し、且つ
R8は、水素、C1〜C12アルキル、C3〜C12シクロアルキル、C3〜C12ヘテロシクロアルキル、C6〜C14アリール、C6〜C14ヘテロアリール、C1〜C12アルコキシ、C3〜C12シクロアルコキシ、C3〜C12ヘテロシクロアルコキシ、C6〜C14アリールオキシ、及びC6〜C14ヘテロアリールオキシから独立して選択される]、
式(IIb)
R10は、C1〜C8アルキル、及びC3〜C8シクロアルキルから独立して選択され、
R11は、CHR10 2、CR10 3、及びC3〜C8シクロアルキルから独立して選択され、
Xは、C−H、C−CH3、及びNから独立して選択され、且つ
A2は、それが結合する部分X、及び介在する炭素原子と一緒になって、5〜7員の環状部分構造を形成する]、
及び式(IIc)
R13、及びR14は、C3〜C8シクロアルキルから独立して選択され、且つ
R15は、H、O−C1〜C6アルキルであるか、又は両方のR15が一緒になって、−CH=CH−架橋を構成する]
の配位子から選択される請求項1に記載の触媒的方法。 - 式(IIa)において、R6が、CR7 3である請求項2に記載の触媒的方法。
- 式(IIb)において、各R10が、C1〜C6アルキル、及びC3〜C7シクロアルキルから独立して選択され、R11が、CR10 3である請求項2〜4のいずれか1項に記載の触媒的方法。
- 式(IIb)において、A2が、−CH=CH−架橋である請求項2〜5のいずれか1項に記載の触媒的方法。
- 式(IIc)において、R15が、H、又はOCH3である請求項2〜6のいずれか1項に記載の触媒的方法。
- 式(IIb)において、Xが、CHである請求項2〜7のいずれか1項に記載の触媒的方法。
- 前記遷移金属錯体が、ニッケル錯体である請求項1〜9のいずれか1項に記載の触媒的方法。
- 前記アルケンが、エテンであり、前記α,β−エチレン性不飽和カルボン酸がアクリル酸である請求項1〜10のいずれか1項に記載の触媒的方法。
- 前記アルケン、及び二酸化炭素を、還元剤の存在下で反応させる請求項1〜11のいずれか1項に記載の触媒的方法。
- 前記反応媒体が、非プロトン性有機溶媒を含む請求項1〜12のいずれか1項に記載の触媒的方法。
- 前記非プロトン性有機溶媒が、
・4〜8個の炭素原子を有する環状アルキルエーテル、
・2〜12個の炭素原子を有するジアルキルエーテル、
・4〜12個の炭素原子を有するシクロアルキルアルキルエーテル、
・7〜16個の炭素原子を有するアリールアルキルエーテル、
・12〜16個の炭素原子を有するビアリール、
・12〜16個の炭素原子を有するジアリールオキシド
・C6〜C10アリールモノカルボン酸のC1〜C8アルキルエステル、
・C6〜C10アリールジカルボン酸のジ−C1〜C8アルキルエステル、
・3〜13個の炭素原子を有するジアルキルカーボネート、
・2〜8個の炭素原子を有するジオキシアルキレン残基、及び2個のC1〜C8アルキル残基からなるジエーテル、
・1〜4個の水素原子が、1〜4個のC1〜C4アルキル残基に置換されたベンゼン、
・ハロゲン化ベンゼン、
・5〜18個の炭素原子を有するアルカン、
及びそれらの混合物
から選択される請求項13に記載の触媒的方法。 - 前記塩基が、アリールオキシドから選択される請求項1〜14のいずれか1項に記載の触媒的方法。
- 前記アリールオキシドが、ナトリウム2−フルオロフェノラート、ナトリウム3−フルオロフェノラート、ナトリウム2−クロロフェノラート、及びナトリウム3−クロロフェノラートから選択される請求項15に記載の触媒的方法。
- 前記アリールオキシドが、ナトリウム2,6−ジメチルフェノラート、ナトリウム2,6−ジイソプロピルフェノラート、ナトリウム2−メチル−6−tert−ブチルフェノラート、ナトリウム2,6−ジ−tert−ブチルフェノキシド、ナトリウム2,6−ジメチルフェノラート、ナトリウム2,6−ジメチル−4−tert−ブチルフェノラート、ナトリウム2,4,6−トリメチルフェノラート、ナトリウム2,6−ジ−tert−ブチル−4−メチルフェノラート、ナトリウム2,6−ジ−tert−ブチル−4−sec−ブチルフェノラート、及び2,4,6−トリ−tert−ブチルフェノラートから選択される請求項15に記載の触媒的方法。
- 前記α,β−エチレン性不飽和カルボン酸塩を、前記反応媒体から除去し、前記反応媒体からの前記α、β−エチレン性不飽和カルボン酸塩の除去が、前記α,β−エチレン性不飽和カルボン酸塩が濃縮された第一液相と、前記カルボキシル化触媒、前記塩基、及び前記塩基の共役酸が濃縮された第二液相への液−液相分離を含み、前記第一、及び第二液相を、極性溶媒を前記反応媒体と接触させることによって得る請求項1〜17のいずれか1項に記載の触媒的方法。
- アルカリ性物質を添加することによって、前記アリールオキシドを再生する工程を含む請求項15〜18のいずれか1項に記載の触媒的方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14168612 | 2014-05-16 | ||
EP14168612.1 | 2014-05-16 | ||
PCT/EP2015/060535 WO2015173276A1 (en) | 2014-05-16 | 2015-05-13 | Process for preparing an unsaturated carboxylic acid salt |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017523127A JP2017523127A (ja) | 2017-08-17 |
JP6635948B2 true JP6635948B2 (ja) | 2020-01-29 |
Family
ID=50731956
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016567978A Active JP6635948B2 (ja) | 2014-05-16 | 2015-05-13 | 不飽和カルボン酸塩を調製する方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US10011551B2 (ja) |
EP (1) | EP3142992B2 (ja) |
JP (1) | JP6635948B2 (ja) |
KR (1) | KR20170010800A (ja) |
CN (1) | CN106458823B (ja) |
RU (1) | RU2016149428A (ja) |
SG (1) | SG11201609591PA (ja) |
WO (1) | WO2015173276A1 (ja) |
Families Citing this family (15)
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 |
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 |
EP3325457B1 (en) | 2015-07-22 | 2020-01-01 | Basf Se | Process for preparing furan-2,5-dicarboxylic acid |
US10428039B2 (en) | 2015-11-04 | 2019-10-01 | Basf Se | Process for preparing furan-2,5-dicarboxylic acid |
BR112018008730A8 (pt) | 2015-11-04 | 2019-02-26 | Basf Se | ?processo para preparar uma mistura e uso de um éster de ácido carboxílico? |
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 |
CN108368017B (zh) | 2015-12-15 | 2021-07-09 | 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 |
EP3426627A1 (en) * | 2016-04-06 | 2019-01-16 | Chevron Phillips Chemical Company LP | Methods for the production of , -unsaturated carboxylic acids and salts thereof |
EP3442939B1 (en) * | 2016-04-11 | 2020-08-26 | Basf Se | Process for preparing an unsaturated carboxylic acid salt |
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 |
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 |
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 |
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 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4792620A (en) * | 1983-10-14 | 1988-12-20 | Bp Chemicals Limited | Carbonylation catalysts |
US7169953B2 (en) | 2001-11-09 | 2007-01-30 | The Penn State Research Foundation | P-chiral phospholanes and phosphocyclic compounds and their use in asymmetric catalytic reactions |
US7608709B2 (en) | 2005-07-25 | 2009-10-27 | National University Corporation Chiba University | 2, 3-bis(dialkylphosphino)pyrazine derivative, process of producing the same, and metal complex having the same as ligand |
CN102884025A (zh) * | 2010-03-03 | 2013-01-16 | 巴斯夫欧洲公司 | 通过链烯的羧基化制备烯属不饱和羧酸盐的方法 |
US8642803B2 (en) * | 2010-03-03 | 2014-02-04 | Basf Se | Preparation of ethylenically unsaturated carboxylic salts by carboxylation of alkenes |
JP6122030B2 (ja) | 2011-12-29 | 2017-04-26 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | アルケンの触媒的カルボキシル化によるα,β−エチレン性不飽和カルボン酸塩の調製 |
WO2014012908A1 (de) * | 2012-07-17 | 2014-01-23 | Basf Se | Übergangsmetallcarbenkomplex- katalysiertes verfahren zur herstellung von carbonsäureestern aus alkoholen unter dehydrierung |
-
2015
- 2015-05-13 EP EP15722197.9A patent/EP3142992B2/en active Active
- 2015-05-13 WO PCT/EP2015/060535 patent/WO2015173276A1/en active Application Filing
- 2015-05-13 SG SG11201609591PA patent/SG11201609591PA/en unknown
- 2015-05-13 KR KR1020167035121A patent/KR20170010800A/ko unknown
- 2015-05-13 JP JP2016567978A patent/JP6635948B2/ja active Active
- 2015-05-13 CN CN201580025354.4A patent/CN106458823B/zh active Active
- 2015-05-13 RU RU2016149428A patent/RU2016149428A/ru unknown
- 2015-05-13 US US15/311,012 patent/US10011551B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
JP2017523127A (ja) | 2017-08-17 |
EP3142992B1 (en) | 2018-09-26 |
US20170217869A1 (en) | 2017-08-03 |
EP3142992B2 (en) | 2022-02-16 |
KR20170010800A (ko) | 2017-02-01 |
SG11201609591PA (en) | 2016-12-29 |
CN106458823B (zh) | 2022-04-19 |
EP3142992A1 (en) | 2017-03-22 |
US10011551B2 (en) | 2018-07-03 |
CN106458823A (zh) | 2017-02-22 |
RU2016149428A (ru) | 2018-06-19 |
WO2015173276A1 (en) | 2015-11-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6635948B2 (ja) | 不飽和カルボン酸塩を調製する方法 | |
US9758461B2 (en) | Process for preparing an unsaturated carboxylic acid salt using an aryloxide | |
US10138196B2 (en) | Process for preparing an unsaturated carboxylic acid salt | |
KR102346316B1 (ko) | 불포화 카복시산 염의 제조 방법 | |
US8697909B2 (en) | Preparation of α,β-ethylenically unsaturated carboxylic salts by catalytic carboxylation of alkenes | |
JP6122030B2 (ja) | アルケンの触媒的カルボキシル化によるα,β−エチレン性不飽和カルボン酸塩の調製 | |
JP2013521261A (ja) | アルケンのカルボキシル化によるエチレン性不飽和カルボン酸塩の製造 | |
WO2015173307A1 (en) | Preparing an unsaturated carboxylic acid salt from an alkene and carbon dioxide using a heterogeneous alkalinity reservoir | |
WO2015173295A1 (en) | Preparing an unsaturated carboxylic acid salt from an alkene and carbon dioxide using a covalently immobilized transition metal complex | |
JP2018515535A5 (ja) | ||
Brill et al. | Transition metal-catalyzed carboxylation of organic substrates with carbon dioxide | |
EP4121407B1 (en) | Catalytic process for preparing an alpha, beta-ethylenically unsaturated carboxylic acid salt |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170705 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180511 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20190410 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190416 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190704 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190806 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20191025 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20191119 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20191217 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6635948 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |