KR970706240A - 하이드로시안화 공정 및 이의 다좌 아인산염 및 니켈 촉매 조성물(hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor) - Google Patents
하이드로시안화 공정 및 이의 다좌 아인산염 및 니켈 촉매 조성물(hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor) Download PDFInfo
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- KR970706240A KR970706240A KR1019970702236A KR19970702236A KR970706240A KR 970706240 A KR970706240 A KR 970706240A KR 1019970702236 A KR1019970702236 A KR 1019970702236A KR 19970702236 A KR19970702236 A KR 19970702236A KR 970706240 A KR970706240 A KR 970706240A
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- 238000000034 method Methods 0.000 title claims abstract 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims 6
- 238000005669 hydrocyanation reaction Methods 0.000 title abstract 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract 6
- 239000002841 Lewis acid Substances 0.000 claims abstract 5
- 150000001875 compounds Chemical class 0.000 claims abstract 5
- 150000007517 lewis acids Chemical class 0.000 claims abstract 5
- 239000005977 Ethylene Substances 0.000 claims abstract 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 3
- 239000010949 copper Substances 0.000 claims 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- 239000007858 starting material Substances 0.000 claims 3
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 229910007926 ZrCl Inorganic materials 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 2
- 229910052759 nickel Inorganic materials 0.000 claims 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
- YPGLWPWPVJBCEM-UHFFFAOYSA-K [Pt+3].[O-]P([O-])([O-])=O Chemical compound [Pt+3].[O-]P([O-])([O-])=O YPGLWPWPVJBCEM-UHFFFAOYSA-K 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 150000001336 alkenes Chemical group 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 229910052793 cadmium Inorganic materials 0.000 claims 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 239000011733 molybdenum Substances 0.000 claims 1
- 150000004682 monohydrates Chemical class 0.000 claims 1
- 229910052758 niobium Inorganic materials 0.000 claims 1
- 239000010955 niobium Substances 0.000 claims 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims 1
- 150000002895 organic esters Chemical group 0.000 claims 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims 1
- 239000007774 positive electrode material Substances 0.000 claims 1
- 229910052706 scandium Inorganic materials 0.000 claims 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
- 239000003426 co-catalyst Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
-
- 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
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
-
- 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- 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
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
-
- 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
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
- B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
0가 니켈 및 다좌 아인산염 리간드를 포함하는 촉매 조성물을 루이스산 조촉매의 존재하에 사용하는, 에틸렌 이중 결합이 분자내의 서로 다른 불포화된 그룹에 공액되지 않은 지방족 모노에틸렌계 불포화 화합물, 또는 에틸렌 이중 결합이 에스테르 그룹에 공액된 모노에틸렌계 불포화 화합물의 하이드로시안화 공정.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (13)
- 에틸렌의 이중 결합이 분자내의 다른 올레핀 그룹에 공액되지 않은 지환족, 지방족, 모노에틸렌계 불포화 화합물, 또는 에틸렌의 이중 결합이 유기 에스테르 그룹에 공액된 모노에틸린계 불포화 화합물을, 루이스산, 0가 니켈, 및 하기 화학식(Ⅰ),(Ⅱ),(Ⅲ),(Ⅳ),(Ⅴ),(Ⅵ) 및 (Ⅶ)로 표시되는 그룹으로부터 선택되는 하나 이상의 다좌 아인산염 리간드를 포함하는 촉매 조성물의 존재하에 HCN원과 반응시킴을 포함하는 하이드로시안화 공정 ;상기 식에서, R1은 각각 독립적으로 H, 할로겐, C1-C6알킬, 또는 R3가 C1-C6알킬인 OR3이고; R2는 각각 독립적으로 탄소수 3 내지 6의 2급 또는 3급 하이드로카빌이고; R2'는 각각 독립적으로, H, 할로겐, R3가 C1-C6알킬인 OR3, 또는 탄소수 1 내지 6의 1급, 2급 또는 3급 하이드로카빌이고; 화학식(Ⅱ),(Ⅲ),(Ⅳ),(Ⅵ) 및 (Ⅶ)의 경우 R2'는 산소에 메타 또는 파라 위치이고; R5′는 각각 독립적으로 H 또는 산소에 대해 오르토 또는 메타 위치인 탄소수 1 내지 3의 1급 또는 2급 하이드로카빌, 또는 CO2R3´이고, 이때 R3'는 C1-C4알킬이고; X는 각각 독립적으로 0 또는 CH(R4′)이고, 이때 R4′는 H, 치환된 페닐 또는 C1-C6알킬이고; 단, ″2급″ 및 ″3급″란 용어는 방향족 환에 결합된 탄소원자를 의미하고, 추가로 화학식(Ⅰ),(Ⅱ) 및 (Ⅴ)에서는 하나 이상의 R2가 3급 하이드로카빌일 수 없다.
- 제1항에 있어서, 에틸렌계 불포화 출발 화합물이 하기 화학식(Ⅷ) 및 (X)의 화합물로 구성된 그룹에서 선택되는 공정;CH3-(CH2)Y-CH=CH-(CH2)X-R4(Ⅷ)CH2=CH-(CH2)X-R4 (X)상기 식에서, R4는 H, CN, CO2R5또는 퍼플루오로알킬이고; y는 0 내지 12의 정수이고; x는 R4가 H, CO2R5또는 퍼플루오로알킬의 경우 0 내지 12의 정수이고; x는 R4가 CN일 경우 1 내지 12의 정수이고; 및 R5는 알킬이다.
- 제1항에 있어서, 에틸렌계 불포화 출발 화합물이 3-펜텐니트릴, 4-펜텐니트릴; 알킬 2,3-및 4-펜테노에이트 및 z가 1 내지 12의 정수인 CxF2x+1CH=CH2로 구성된 그룹에서 선택되는 공정.
- 제3항에 있어서, 에틸렌계 불포화 출발 화합물이 3-펜텐니트릴 또는 4-펜텐니트릴인 공정.
- 제1항에 있어서, -25℃ 내지 200℃의 온도 및 50.6 내지 1013kPa의 압력에서 수행되는 공정.
- 제5항에 있어서, 대기압 및 0 내지 150℃의 온도에서 수행되는 공정.
- 제1항에 있어서, 루이스산이, 스칸듐, 티탄, 바나듐, 크로뮴, 망간, 철, 코발트, 구리, 아연, 붕소, 알루미늄, 이트륨, 지르코늄, 니오븀, 몰리브덴, 카드뮴, 레늄 및 주성으로부터 양 이온이 선택되는 무기 또는 유기금속 화합물로 구성되는 그룹에서 선택되는 공정.
- 제7항에 있어서, 루이스산이 ZnBr2, ZnI2, ZnCl2, ZnSO4, CuCl, CuCl, Cu(O3SCF3)2, CoCl2, Col2, FeI3, FeCl2(테트라하이드로푸란)2, TiCl4(테트라하이드로푸란)2, TiCl4, TiCl3, ClTi(OiPr)3, MnCl2, ScCl3, AlCl3, (C8H17)AlCl2, (C8H17)2AlCl, (이소-C4H9)2AlCl, (페닐)2AlCl, 페닐AlCl2, ReCl5, ZrCl4, NbCl5, VCl3, CrCl2, MoCl5, YCl3, CdCl2, LaCl3, Er(O3SCF3)3, Yb(O2CCF3)3, Yb(O2CCF3)3, SmCl5, TaCl5, CdCl2, B(C6H5)3, 및 X가 CF3SO3, CH3C6H5SO3또는 (C6H5)3BCN인 (C6H5)3SnX로 구성된 그룹에서 선택되는 공정.
- 본질적으로 0가 니켈 및 하기 화학식(Ⅰ),(Ⅱ),(Ⅲ),(Ⅳ),(Ⅴ),(Ⅵ) 및 (Ⅶ)로 표시되는 그룹으로부터 선택되는 하나 이상의 다좌 아인산염으로 구성되는 촉매 조성물;상기 식에서, R1은 각각 독립적으로 H, 할로겐, C1-C6알킬, 또는 R3가 C1-C6알킬인 OR3이고; R2는 각각 독립적으로 탄소수 3 내지 6의 2급 또는 3급 하이드로카빌이고; R2'는 각각 독립적으로, H, 할로겐, R3가 C1-C6알킬인 OR3, 또는 탄소수 1 내지 6의 1급, 2급 또는 3급 하이드로카빌이고; 화학식(Ⅱ),(Ⅲ),(Ⅳ),(Ⅵ) 및 (Ⅶ)의 경우 R2'는 산소에 메타 또는 파라 위치이고; R5'는 각각 독립적으로 H 또는 산소에 대해 오르토 또는 메타 위치인 탄소수 1 내지 3의 1급 또는 2급 하이드로카빌, 또는 CO2R3´이고, 이때 R3'는 C1-C4알킬이고; X는 각각 독립적으로 0 또는 CH(R4′)이고, 이때 R4′는 H,치환된 페닐 또는 C1-C6알킬이고; 단, “2급” 및 “3급”란 용어는 방향족 환에 결합된 탄소원자를 의미하고, 추가로 화학식(Ⅰ),(Ⅱ) 및 (Ⅴ)에서는 하나 이상의 R2가 3급 하이드로카빌일 수 없다.
- 제9항에 있어서, 또한, 루이스산이 존재하는 촉매 조성물.
- 제10항에 있어서, 루이스산이 ZnBr2, ZnI2, ZnCl2, ZnSO4, CuCl, Cu(O3SCF3)2, CoCl2, CoI2, FeI2, FeCl3, FeCl2(테트라하이드로푸란)2, TiCl4(테트라하이드로푸란)2, TiCl4, TiCl3, ClTi(OiPr)3, MnCl2, ScCl3, AlCl3, (C8H17)AlCl2, (C8H17)2AlCl, (이소-C4H9)2AlCl, (페닐)2AlCl, 페닐AlCl2, ReCl5, ZrCl4, NbCl5, VCl3, CrCl5, MoCl5, YCl3, CdCl2, LaCl3, Er(O3SCF3)3, Yb(O2CCF3)3, SmCl3, TaCl5, CdCl2, B(C6H5)3, 및 X가 CF3SO3, CH3C6H5SO3또는 (C6H5)3BCN인 (C6H5)3SnX로 구성된 그룹에서 선택되는 촉매 조성물.
- 제9항에 있어서, 0가 니켈 및 다좌 아인산염 리간드가 서로 결합된 촉매 조성물.
- 제9항에 있어서, 0가 니켈 및 다좌 아인산염 리간드가 동일한 고형 지지체상에 지지되는 촉매 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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US8/505,137 | 1995-07-21 | ||
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US08/505,137 | 1995-07-21 | ||
PCT/US1995/012214 WO1996011182A1 (en) | 1994-10-07 | 1995-09-29 | Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor |
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-
1995
- 1995-09-26 TW TW084110060A patent/TW315370B/zh not_active IP Right Cessation
- 1995-09-29 KR KR1019970702236A patent/KR100257363B1/ko not_active IP Right Cessation
- 1995-09-29 WO PCT/US1995/012214 patent/WO1996011182A1/en active IP Right Grant
- 1995-09-29 CN CN95195429A patent/CN1047163C/zh not_active Expired - Lifetime
- 1995-09-29 DE DE69507819T patent/DE69507819T2/de not_active Expired - Lifetime
- 1995-09-29 BR BR9509494A patent/BR9509494A/pt not_active IP Right Cessation
- 1995-09-29 AT AT95935101T patent/ATE176665T1/de not_active IP Right Cessation
- 1995-09-29 JP JP51259296A patent/JP3535172B2/ja not_active Expired - Fee Related
- 1995-09-29 EP EP95935101A patent/EP0784610B1/en not_active Expired - Lifetime
- 1995-09-29 ES ES95935101T patent/ES2129234T3/es not_active Expired - Lifetime
- 1995-09-29 CA CA002200303A patent/CA2200303C/en not_active Expired - Fee Related
- 1995-10-06 MY MYPI95003002A patent/MY112815A/en unknown
- 1995-10-16 US US08/543,672 patent/US5663369A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CN1159799A (zh) | 1997-09-17 |
JP3535172B2 (ja) | 2004-06-07 |
CA2200303A1 (en) | 1996-04-18 |
US5663369A (en) | 1997-09-02 |
ATE176665T1 (de) | 1999-02-15 |
EP0784610B1 (en) | 1999-02-10 |
TW315370B (ko) | 1997-09-11 |
JPH10506911A (ja) | 1998-07-07 |
DE69507819T2 (de) | 1999-08-12 |
ES2129234T3 (es) | 1999-06-01 |
CA2200303C (en) | 2007-01-09 |
DE69507819D1 (de) | 1999-03-25 |
CN1047163C (zh) | 1999-12-08 |
MY112815A (en) | 2001-09-29 |
EP0784610A1 (en) | 1997-07-23 |
WO1996011182A1 (en) | 1996-04-18 |
KR100257363B1 (ko) | 2000-05-15 |
BR9509494A (pt) | 1997-10-14 |
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