CA2862155A1 - Preparation de sels d'acides carboxyliques a insaturation ?,?-ethylenique par carboxylation catalytique d'alcenes - Google Patents

Preparation de sels d'acides carboxyliques a insaturation ?,?-ethylenique par carboxylation catalytique d'alcenes Download PDF

Info

Publication number: CA2862155A1
Authority: CA; Canada
Prior art keywords: alkaline earth; metal; earth metal; alkali metal; transition metal
Prior art date: 2011-12-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA2862155A

Other languages

English (en)

Inventor

Michael Limbach

Ronald LINDNER

Michael Ludwik LEJKOWSKI

Takeharu KAGEYAMA

Gabriella Eva BODIZS

Stephan Schunk

Cornelia FUTTER

Jorg Rother

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

2011-12-29

Filing date

2012-12-27

Publication date

2013-07-04

2012-12-27 Application filed by BASF SE filed Critical BASF SE

2013-07-04 Publication of CA2862155A1 publication Critical patent/CA2862155A1/fr

Status Abandoned legal-status Critical Current

Links

150000001336 alkenes Chemical class 0.000 title claims abstract description 45
150000003839 salts Chemical class 0.000 title claims description 6
230000003197 catalytic effect Effects 0.000 title description 16
230000021523 carboxylation Effects 0.000 title description 10
238000006473 carboxylation reaction Methods 0.000 title description 10
238000002360 preparation method Methods 0.000 title description 6
-1 alkaline earth metal salt Chemical class 0.000 claims abstract description 79
150000001340 alkali metals Chemical class 0.000 claims abstract description 64
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 61
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 60
239000003446 ligand Substances 0.000 claims abstract description 48
229910052723 transition metal Inorganic materials 0.000 claims abstract description 43
150000003624 transition metals Chemical class 0.000 claims abstract description 43
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 34
239000002585 base Substances 0.000 claims abstract description 33
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 claims abstract description 31
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 29
230000007704 transition Effects 0.000 claims abstract description 28
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 27
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims abstract description 9
239000004032 superbase Substances 0.000 claims abstract description 8
238000004519 manufacturing process Methods 0.000 claims abstract description 7
229910000272 alkali metal oxide Inorganic materials 0.000 claims abstract description 4
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract 3
238000000034 method Methods 0.000 claims description 26
230000008569 process Effects 0.000 claims description 25
239000000203 mixture Chemical class 0.000 claims description 22
150000001342 alkaline earth metals Chemical class 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 12
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 11
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
125000004437 phosphorous atom Chemical group 0.000 claims description 11
239000007791 liquid phase Substances 0.000 claims description 10
229910052751 metal Inorganic materials 0.000 claims description 10
239000002184 metal Substances 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000012429 reaction media Substances 0.000 claims description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical class CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
238000005191 phase separation Methods 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 3
WBMJFMFJCWPAIT-UHFFFAOYSA-N ditert-butyl(ditert-butylphosphanylmethyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CP(C(C)(C)C)C(C)(C)C WBMJFMFJCWPAIT-UHFFFAOYSA-N 0.000 claims description 3
150000002170 ethers Chemical class 0.000 claims description 3
239000008346 aqueous phase Substances 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
230000000737 periodic effect Effects 0.000 claims description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract description 38
229910052759 nickel Inorganic materials 0.000 abstract description 8
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 63
229910002092 carbon dioxide Inorganic materials 0.000 description 32
239000005977 Ethylene Substances 0.000 description 24
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
125000000217 alkyl group Chemical group 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 17
229910052739 hydrogen Inorganic materials 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 15
239000001257 hydrogen Substances 0.000 description 15
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 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
238000005481 NMR spectroscopy Methods 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
125000003118 aryl group Chemical group 0.000 description 12
YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 12
230000014509 gene expression Effects 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 10
238000007792 addition Methods 0.000 description 10
UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
229940047670 sodium acrylate Drugs 0.000 description 9
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 9
JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
239000007788 liquid Substances 0.000 description 8
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
238000000926 separation method Methods 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 7
150000007942 carboxylates Chemical class 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
150000002431 hydrogen Chemical group 0.000 description 7
125000001624 naphthyl group Chemical group 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
238000012982 x-ray structure analysis Methods 0.000 description 7
238000004009 13C{1H}-NMR spectroscopy Methods 0.000 description 6
UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 6
150000001721 carbon Chemical group 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
150000002596 lactones Chemical class 0.000 description 6
229910052744 lithium Inorganic materials 0.000 description 6
239000000376 reactant Substances 0.000 description 6
125000003944 tolyl group Chemical group 0.000 description 6
125000005023 xylyl group Chemical group 0.000 description 6
125000000753 cycloalkyl group Chemical group 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
229910052742 iron Inorganic materials 0.000 description 5
239000012071 phase Substances 0.000 description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
229910052703 rhodium Inorganic materials 0.000 description 5
239000010948 rhodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
239000007810 chemical reaction solvent Substances 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
230000007017 scission Effects 0.000 description 4
125000004400 (C1-C12) alkyl group Chemical group 0.000 description 3
PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
229910052707 ruthenium Inorganic materials 0.000 description 3
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 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
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 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
230000008859 change Effects 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
238000001816 cooling Methods 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
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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
230000006837 decompression Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
ARSGXAZDYSTSKI-UHFFFAOYSA-N diphenyl(2-pyridin-2-ylethyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCC1=CC=CC=N1 ARSGXAZDYSTSKI-UHFFFAOYSA-N 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
150000002148 esters Chemical group 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
125000001072 heteroaryl group Chemical group 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 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
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-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
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
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 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
125000002524 organometallic group Chemical group 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
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 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
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000000607 proton-decoupled 31P nuclear magnetic resonance spectroscopy Methods 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000008929 regeneration Effects 0.000 description 2
238000011069 regeneration method Methods 0.000 description 2
150000007525 superbases Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000009466 transformation Effects 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
229910052721 tungsten Inorganic materials 0.000 description 2
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
125000005919 1,2,2-trimethylpropyl group Chemical group 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
125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 1
239000004912 1,5-cyclooctadiene Substances 0.000 description 1
125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
MUOQGMMQUSHAOW-UHFFFAOYSA-N 2-dimethylphosphanyl-n,n-dimethylethanamine Chemical compound CN(C)CCP(C)C MUOQGMMQUSHAOW-UHFFFAOYSA-N 0.000 description 1
GJOGRUGECVQJBK-UHFFFAOYSA-N 2-diphenylphosphanylacetic acid Chemical compound C=1C=CC=CC=1P(CC(=O)O)C1=CC=CC=C1 GJOGRUGECVQJBK-UHFFFAOYSA-N 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005917 3-methylpentyl group Chemical group 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
ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 description 1
125000003627 8 membered carbocyclic group Chemical group 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
102220519703 Cytosolic phospholipase A2 gamma_H44N_mutation Human genes 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 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
150000007513 acids Chemical class 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
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 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
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 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
125000002619 bicyclic group Chemical group 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
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940052810 complex b Drugs 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
150000001925 cycloalkenes Chemical class 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000001514 detection method Methods 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
AAXGWYDSLJUQLN-UHFFFAOYSA-N diphenyl(propyl)phosphane Chemical compound C=1C=CC=CC=1P(CCC)C1=CC=CC=C1 AAXGWYDSLJUQLN-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 description 1
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002390 heteroarenes Chemical class 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000003317 industrial substance Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000002608 ionic liquid Substances 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
238000000622 liquid--liquid extraction Methods 0.000 description 1
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 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
AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 1
YDGSUPBDGKOGQT-UHFFFAOYSA-N lithium;dimethylazanide Chemical compound [Li+].C[N-]C YDGSUPBDGKOGQT-UHFFFAOYSA-N 0.000 description 1
229910012375 magnesium hydride Inorganic materials 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229940017219 methyl propionate Drugs 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
238000002156 mixing Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000000178 monomer Substances 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052756 noble gas Inorganic materials 0.000 description 1
150000002835 noble gases Chemical class 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000005010 perfluoroalkyl group Chemical group 0.000 description 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
125000005538 phosphinite group Chemical group 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
150000004857 phospholes Chemical class 0.000 description 1
XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
150000008300 phosphoramidites Chemical class 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
WKFBZNUBXWCCHG-UHFFFAOYSA-N phosphorus trifluoride Chemical compound FP(F)F WKFBZNUBXWCCHG-UHFFFAOYSA-N 0.000 description 1
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 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
FCLYZQXPJKJTDR-UHFFFAOYSA-N potassium;diphenylphosphanide Chemical compound C=1C=CC=CC=1P([K])C1=CC=CC=C1 FCLYZQXPJKJTDR-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 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
229910052701 rubidium Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
IJLDUKQEDMJQTR-UHFFFAOYSA-M sodium ditert-butyl(2-ditert-butylphosphanylethyl)phosphane prop-2-enoate Chemical compound C(C)(C)(C)P(CCP(C(C)(C)C)C(C)(C)C)C(C)(C)C.C(C=C)(=O)[O-].[Na+] IJLDUKQEDMJQTR-UHFFFAOYSA-M 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
230000003068 static effect Effects 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 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
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/08—Formation or introduction of functional groups containing oxygen of carboxyl groups or salts, halides or anhydrides thereof
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/08—Formation or introduction of functional groups containing oxygen of carboxyl groups or salts, halides or anhydrides thereof
- C07B41/10—Salts, halides or anhydrides of carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CA2862155A 2011-12-29 2012-12-27 Preparation de sels d'acides carboxyliques a insaturation ?,?-ethylenique par carboxylation catalytique d'alcenes Abandoned CA2862155A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP11196025.8		2011-12-29
EP11196025		2011-12-29
PCT/IB2012/057750 WO2013098772A1 (fr)	2011-12-29	2012-12-27	Préparation de sels d'acides carboxyliques à insaturation α,β-éthylénique par carboxylation catalytique d'alcènes

Publications (1)

Publication Number	Publication Date
CA2862155A1 true CA2862155A1 (fr)	2013-07-04

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Application Number	Title	Priority Date	Filing Date
CA2862155A Abandoned CA2862155A1 (fr)	2011-12-29	2012-12-27	Preparation de sels d'acides carboxyliques a insaturation ?,?-ethylenique par carboxylation catalytique d'alcenes

Country Status (6)

Country	Link
EP (1)	EP2797869A4 (fr)
JP (1)	JP6122030B2 (fr)
CN (1)	CN104011004B (fr)
CA (1)	CA2862155A1 (fr)
IN (1)	IN2014CN04656A (fr)
WO (1)	WO2013098772A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111051272A (zh) *	2017-06-14	2020-04-21	切弗朗菲利浦化学公司	用于通过溶液相反应器将烯烃和二氧化碳转化为丙烯酸盐的连续工艺

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Publication number	Priority date	Publication date	Assignee	Title
JP6290195B2 (ja)	2012-06-13	2018-03-07	ビーエーエスエフソシエタス・ヨーロピアＢａｓｆＳｅ	大環状ケトンの製造方法
CN104418719B (zh) *	2013-08-30	2016-04-13	中国石油化工股份有限公司	一种丙烯酸的合成方法
DE102014203951A1 (de) *	2014-03-05	2015-09-10	Evonik Degussa Gmbh	Synthese von alpha,beta-ungesättigten Carbonsäuren (Meth)acrylaten aus Olefinen
WO2015173295A1 (fr) *	2014-05-16	2015-11-19	Basf Se	Préparation d'un sel d'acide carboxylique insaturé à partir d'un alcène et de dioxyde de carbone à l'aide d'un complexe de métal de transition immobilisé de manière covalente
WO2015173307A1 (fr)	2014-05-16	2015-11-19	Basf Se	Préparation d'un sel d'acide carboxylique insaturé à partir d'un alcène et de dioxyde de carbone faisant appel à un réservoir d'alcalinité hétérogène
WO2015173296A1 (fr) *	2014-05-16	2015-11-19	Basf Se	Préparation d'un sel d'acide carboxylique insaturé à partir d'un alcène et de dioxyde de carbone à l'aide d'une base hétérogène
SG11201609591PA (en)	2014-05-16	2016-12-29	Basf Se	Process for preparing an unsaturated carboxylic acid salt
EP3142995B1 (fr) *	2014-05-16	2018-03-21	Basf Se	Procédé de préparation d'un sel d'acide carboxylique insaturé à l'aide d'un oxyde d'aryle
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
JP6253570B2 (ja) *	2014-12-15	2017-12-27	旭化成株式会社	有機酸の製造方法
JP6272791B2 (ja) *	2015-02-24	2018-01-31	旭化成株式会社	有機酸の製造方法
EP3294701B1 (fr) *	2015-05-13	2020-08-12	Basf Se	Procédé de préparation d'un sel d'acide carboxylique insaturé
US10160711B2 (en)	2015-12-15	2018-12-25	Chevron Phillips Chemical Company Lp	Formation of α,β-unsaturated carboxylic acids and salts thereof from metalalactones and anionic polyelectrolytes
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
KR102346316B1 (ko) *	2016-04-11	2022-01-03	바스프 에스이	불포화 카복시산 염의 제조 방법
JP6814573B2 (ja) *	2016-08-26	2021-01-20	株式会社日本触媒	不飽和カルボン酸塩の製造方法
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
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
US10934243B2 (en)	2017-12-25	2021-03-02	Ptt Global Chemical Public Company Limited	Catalyst composition for a producing process of an unsaturated carboxylic acid salt and its derivatives from carbon dioxide and olefin
CN111587236A (zh) *	2018-03-28	2020-08-25	积水化学工业株式会社	α,β-不饱和羧酸盐的制备方法
US11174213B2 (en)	2018-10-12	2021-11-16	Chevron Phillips Chemical Company, Lp	Effects of catalyst concentration and solid activator on nickel-mediated olefin/carbon dioxide coupling to acrylates
CN112745210B (zh) *	2019-10-30	2022-02-15	中国科学院大连化学物理研究所	一种制备α,β-不饱和羧酸化合物的方法
JP2023518539A (ja) *	2020-03-20	2023-05-02	ベーアーエスエフ・エスエー	α，β－エチレン性不飽和カルボン酸塩を調製するための触媒法
CN115959987B (zh) *	2022-12-16	2025-05-09	华东理工大学	一种用于二氧化碳和乙烯制备不饱和羧酸盐的催化剂组合物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4435598A (en) *	1977-10-28	1984-03-06	National Distillers And Chemical Corporation	Process for the catalytic oxidation of propylene to acrylic acid
US20090299094A1 (en) *	2005-06-13	2009-12-03	Mitsubishi Rayon Co., Ltd.	Process for producing alpha, beta-unsaturated carboxylic acid
EP2542516A2 (fr) *	2010-03-03	2013-01-09	Basf Se	Préparation de sels d'acides carboxyliques éthyléniquement insaturés par carboxylation d'alcènes

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- 2012-12-27 CA CA2862155A patent/CA2862155A1/fr not_active Abandoned
- 2012-12-27 JP JP2014549615A patent/JP6122030B2/ja active Active
- 2012-12-27 WO PCT/IB2012/057750 patent/WO2013098772A1/fr not_active Ceased
- 2012-12-27 CN CN201280064974.5A patent/CN104011004B/zh not_active Expired - Fee Related
- 2012-12-27 EP EP12861287.6A patent/EP2797869A4/fr not_active Withdrawn
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111051272A (zh) *	2017-06-14	2020-04-21	切弗朗菲利浦化学公司	用于通过溶液相反应器将烯烃和二氧化碳转化为丙烯酸盐的连续工艺

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IN2014CN04656A (fr)	2015-09-18
WO2013098772A1 (fr)	2013-07-04
EP2797869A1 (fr)	2014-11-05
CN104011004A (zh)	2014-08-27
CN104011004B (zh)	2016-04-20
EP2797869A4 (fr)	2015-08-05
JP2015503547A (ja)	2015-02-02
JP6122030B2 (ja)	2017-04-26

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US8697909B2 (en)	2014-04-15	Preparation of α,β-ethylenically unsaturated carboxylic salts by catalytic carboxylation of alkenes
JP6122030B2 (ja)	2017-04-26	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
JP6635948B2 (ja)	2020-01-29	不飽和カルボン酸塩を調製する方法
EP3294701B1 (fr)	2020-08-12	Procédé de préparation d'un sel d'acide carboxylique insaturé
CN106458824B (zh)	2020-10-16	使用芳基氧化物制备不饱和羧酸盐的方法
TWI473785B (zh)	2015-02-21	使用金屬螯配位體催化劑用於醋酸之生產的羰基化方法
CN108884010B (zh)	2022-11-08	制备不饱和羧酸盐的方法
CA2791834A1 (fr)	2011-09-09	Preparation de sels d'acides carboxyliques ethyleniquement insatures par carboxylation d'alcenes
WO2015173307A1 (fr)	2015-11-19	Préparation d'un sel d'acide carboxylique insaturé à partir d'un alcène et de dioxyde de carbone faisant appel à un réservoir d'alcalinité hétérogène
EP4121407B1 (fr)	2024-03-06	Procédé catalytique pour la préparation d'un sel d'acide carboxylique alpha, beta-insaturé

CA2862155A1 - Preparation de sels d'acides carboxyliques a insaturation ?,?-ethylenique par carboxylation catalytique d'alcenes - Google Patents

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