KR970707079A - 비공액 2-알킬-3-모노알켄니트릴의 촉매화 기상 이성질화(catalyzed gas phase isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles) - Google Patents
비공액 2-알킬-3-모노알켄니트릴의 촉매화 기상 이성질화(catalyzed gas phase isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles)Info
- Publication number
- KR970707079A KR970707079A KR1019970703330A KR19970703330A KR970707079A KR 970707079 A KR970707079 A KR 970707079A KR 1019970703330 A KR1019970703330 A KR 1019970703330A KR 19970703330 A KR19970703330 A KR 19970703330A KR 970707079 A KR970707079 A KR 970707079A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- starting
- isomerization
- nitrile
- catalyst
- Prior art date
Links
- 238000006317 isomerization reaction Methods 0.000 title claims abstract 8
- 230000003197 catalytic effect Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract 13
- 239000003054 catalyst Substances 0.000 claims abstract 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000003446 ligand Substances 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims abstract 2
- 229910052759 nickel Inorganic materials 0.000 claims abstract 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002015 acyclic group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 150000002825 nitriles Chemical class 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical group C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- -1 aliphatic nitriles Chemical class 0.000 claims 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 239000012808 vapor phase Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
-
- 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
- B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/02—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C255/03—Mononitriles
-
- 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
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/52—Isomerisation reactions
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
본 발명은 2-알킬-3-모노알켄니트릴을 3-모노알켄니트릴 및/또는 4-모노알켄니트릴로 촉매 이성질화 하는 기상 방법에 관한 것으로, 영가 니켈 및 이배위 아인산염 리간드의 지지 조성물은 촉매로서 사용된다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- 약 135℃ 내지 약 170℃의 범위의 온도에서 영가 니켈 및 하기 화학식(Ⅰ) 및 화학식(Ⅱ)로 이루어지는 그룹으로부터 선택되는 하나 이상의 이배위 아인산염 리간다를 포함하는 지지 촉매 조성물과 비환식, 지방족, 비공액 2-알킬-3-모노알켄니트릴의 출발 니트릴을 접촉시켜 비공액, 선형, 비환식 3-모노알켄 니트릴 및/또는 4-모노알켄 니트릴을 생성하는 것을 포함하는, 비환식, 지방족, 비공액 2-알킬-3-모노알켄니트릴의 기상 이성질화 방법 :상기 식에서, 각각의 R1은 독립적으로 3 내지 12개의 탄소원자의 2급 또는 3급 하이드로카빌이고; 각각의 R2는 독립적으로 H, C1내지 C12알킬 또는 OR3(R3는 C1내지 C12알킬이다)이고; 및상기 식에서, 각각의 R4는 독립적으로 12개 이하의 탄소원자의 3급 탄화수소 또는 OR5(R5는 C1내지 C12알킬이다)이고; 및 각각의 R6는 독립적으로 12개 이하의 탄소원자의 3급 탄화수소이다.
- 제1항에 있어서, 반응온도가 140℃ 내지 160℃인 방법.
- 제2항에 있어서, 반응온도가 145℃ 내지 150℃인 방법.
- 제1항에 있어서, 출발 2-알킬-3-모노알켄니트릴이 하기 화학식으로 나타내어지는 화합물인 방법 :상기 식에서, R7은 H 또는 C1내지 C3알킬이다.
- 제4항에 있어서, 출발 니트릴이 2-메틸-3-부텐니트릴인 방법.
- 제1항에 있어서, 출발 2-알킬-3-모노알켄니트릴이 촉매에 해로운 영향을 주지 않는 하나 이상의 다른 기로 추가로 치환되는 방법.
- 제1항에 있어서, 이성질화가 101.3kPa 내지 1013kPa의 압력에서 수행되는 방법.
- 제1항에 있어서, 출발 2-알킬-3-알켄니트릴 대 촉매의 몰비가 5 :1/시간 내지 100 : 1/시간이 되도록 하는 공급속도에서 연속적 방법으로 이성질화가 수행되는 방법.
- 제1항에 있어서, 촉매가 실리카, 알루미나 및 탄소로 이루어지는 그룹으로부터 선택되는 캐리어상에서 지지되는 방법.
- 제1항에 있어서, 출발 2-알킬-3-알켄니트릴 순수한 증기로서 이성절화 반응에 도입되는 방법.
- 제1항에 있어서, 출발 2-알킬-3-알켄니트릴이 휘발성 용매중의 증발 용액으로서 이성질화 반응에 도입되는 방법.
- 제11항에 있어서, 상기 용매가 이성질화 반응온도에서 기체성인 포화 및 방향족 탄화수소 및 지방족 니트릴로 이루어지는 그룹으로부터 선택되는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/341,726 US5440067A (en) | 1994-11-18 | 1994-11-18 | Catalyzed gas phase isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles |
US08/341,726 | 1994-11-18 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR970707079A true KR970707079A (ko) | 1997-12-01 |
KR100267821B1 KR100267821B1 (ko) | 2000-10-16 |
Family
ID=23338763
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019970703330A KR100267821B1 (ko) | 1994-11-18 | 1995-11-01 | 비공액2-알킬-3모노알켄니트릴의촉매화된기상이성질화 |
Country Status (13)
Country | Link |
---|---|
US (1) | US5440067A (ko) |
EP (1) | EP0792260B1 (ko) |
JP (1) | JP3478400B2 (ko) |
KR (1) | KR100267821B1 (ko) |
CN (1) | CN1077883C (ko) |
AT (1) | ATE182136T1 (ko) |
BR (1) | BR9510346A (ko) |
CA (1) | CA2200302C (ko) |
DE (1) | DE69510816T2 (ko) |
ES (1) | ES2136320T3 (ko) |
IN (1) | IN186365B (ko) |
MY (1) | MY112489A (ko) |
WO (1) | WO1996016025A1 (ko) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK0730574T3 (da) * | 1993-11-23 | 1999-05-25 | Du Pont | Fremgangsmåder og katalysatorsammensætninger til hydrocyanering af monoolefiner |
JP3519410B2 (ja) | 1994-04-14 | 2004-04-12 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | モノオレフィン類のヒドロシアン化用二座ホスファイトとニッケル触媒の組成物 |
US5512696A (en) * | 1995-07-21 | 1996-04-30 | E. I. Du Pont De Nemours And Company | Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor |
TW315370B (ko) * | 1994-10-07 | 1997-09-11 | Du Pont | |
IN187044B (ko) * | 1995-01-27 | 2002-01-05 | Du Pont | |
US5821378A (en) * | 1995-01-27 | 1998-10-13 | E. I. Du Pont De Nemours And Company | Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles |
US5693843A (en) * | 1995-12-22 | 1997-12-02 | E. I. Du Pont De Nemours And Company | Process for hydrocyanation of diolefins and isomerization of nonconjugated 2 alkyl-3-monoalkenenitriles |
IN191158B (ko) * | 1996-04-02 | 2003-10-11 | Du Pont | |
DE19825212A1 (de) | 1998-06-05 | 1999-12-09 | Basf Ag | Katalysator, umfassend einen Komplex eines Metalls der VIII. Nebengruppe auf Basis eines zweizähnigen Phosphonitliganden und Verfahren zur Herstellung von Nitrilen |
FR2823746B1 (fr) * | 2001-04-20 | 2003-05-23 | Rhodia Polyamide Intermediates | Procede d'isomerisation de mononitriles insatures ramifies en mononitriles insatures lineaires |
FR2849027B1 (fr) * | 2002-12-23 | 2005-01-21 | Rhodia Polyamide Intermediates | Procede de synthese de composes comprenant des fonctions nitriles a partir de composes a insaturations ethyleniques |
FR2850966B1 (fr) | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
DE10311119A1 (de) * | 2003-03-12 | 2004-09-23 | Basf Ag | Verfahren zur Isomerisierung von 2-Methyl-3-butennitril zu linearem Pentennitril |
DE10323803A1 (de) * | 2003-04-22 | 2004-11-11 | Basf Ag | Verfahren zur Isomerisierung von cis-2-Pentennitril zu trans-3-Pentennitril |
FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
FR2854892B1 (fr) * | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
US7709674B2 (en) | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L | Hydrocyanation process with reduced yield losses |
DE102008043584A1 (de) | 2008-11-07 | 2010-05-12 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von 6-Chlorodibenzo(d,f) (1,3,2)-dioxaphosphepin |
DE102008043582A1 (de) | 2008-11-07 | 2010-05-12 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von 6-Chlorodibenzo(d,f) (1,3,2)-dioxaphosphepin |
DE102011002640B4 (de) | 2011-01-13 | 2021-10-07 | Evonik Operations Gmbh | Verfahren zur Aufreinigung von Biphephos |
DE102011002639A1 (de) | 2011-01-13 | 2012-07-19 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von Biphephos |
ES2772074T3 (es) | 2014-05-20 | 2020-07-07 | Evonik Operations Gmbh | Procedimiento para la reducción del contenido en cloro de organomonofosfitos usando dimetilaminobutano, trietilamina o trietanolamina |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3853948A (en) * | 1965-11-23 | 1974-12-10 | Du Pont | Catalytic isomerization of 2-methyl-3-butenenitrile to linear pentene-nitriles |
US3526654A (en) * | 1968-05-17 | 1970-09-01 | Du Pont | Isomerization of 2-pentenenitrile to 3-pentenenitrile |
US3676481A (en) * | 1970-06-29 | 1972-07-11 | Du Pont | Catalytic isomerization of 2-methyl-3-butenenitrile to linear pentenenitriles in the presence of certain metal salt and/or tri(hydrocarbyl)boron promoters |
US3739011A (en) * | 1971-04-30 | 1973-06-12 | Du Pont | Catalytic isomerization of 2-methyl-3-butenenitrile to linear pentenenitriles |
US3766237A (en) * | 1972-01-25 | 1973-10-16 | Du Pont | Hydrocyanation of olefins |
US3852325A (en) * | 1973-08-29 | 1974-12-03 | Du Pont | Selective isomerization of pentenenitriles |
US3852328A (en) * | 1973-09-26 | 1974-12-03 | Du Pont | Catalytic isomerization of 2-methyl-3-butenenitrile to a linear pentenenitrile |
US3852329A (en) * | 1973-10-02 | 1974-12-03 | Du Pont | Process for isomerization of 2-methyl-3-butene-nitrile to a linear pentenenitrile |
US4298546A (en) * | 1980-08-05 | 1981-11-03 | E. I. Du Pont De Nemours And Company | Isomerization of 2-methyl-3-butenenitrile |
US4783546A (en) * | 1987-06-02 | 1988-11-08 | E. I. Du Pont De Nemours And Company | Preparation of 4-pentenenitrile by isomerization |
-
1994
- 1994-11-18 US US08/341,726 patent/US5440067A/en not_active Expired - Lifetime
-
1995
- 1995-10-26 IN IN1321CA1995 patent/IN186365B/en unknown
- 1995-11-01 EP EP95941392A patent/EP0792260B1/en not_active Expired - Lifetime
- 1995-11-01 KR KR1019970703330A patent/KR100267821B1/ko not_active IP Right Cessation
- 1995-11-01 ES ES95941392T patent/ES2136320T3/es not_active Expired - Lifetime
- 1995-11-01 BR BR9510346A patent/BR9510346A/pt not_active IP Right Cessation
- 1995-11-01 DE DE69510816T patent/DE69510816T2/de not_active Expired - Lifetime
- 1995-11-01 CA CA002200302A patent/CA2200302C/en not_active Expired - Fee Related
- 1995-11-01 WO PCT/US1995/014790 patent/WO1996016025A1/en active IP Right Grant
- 1995-11-01 JP JP51695496A patent/JP3478400B2/ja not_active Expired - Fee Related
- 1995-11-01 AT AT95941392T patent/ATE182136T1/de not_active IP Right Cessation
- 1995-11-01 CN CN95196268A patent/CN1077883C/zh not_active Expired - Lifetime
- 1995-11-18 MY MYPI95003526A patent/MY112489A/en unknown
Also Published As
Publication number | Publication date |
---|---|
BR9510346A (pt) | 1998-06-02 |
CA2200302A1 (en) | 1996-05-30 |
DE69510816D1 (de) | 1999-08-19 |
ES2136320T3 (es) | 1999-11-16 |
JPH10509175A (ja) | 1998-09-08 |
EP0792260A1 (en) | 1997-09-03 |
ATE182136T1 (de) | 1999-07-15 |
EP0792260B1 (en) | 1999-07-14 |
WO1996016025A1 (en) | 1996-05-30 |
MY112489A (en) | 2001-06-30 |
CA2200302C (en) | 2007-01-09 |
CN1077883C (zh) | 2002-01-16 |
CN1168664A (zh) | 1997-12-24 |
JP3478400B2 (ja) | 2003-12-15 |
DE69510816T2 (de) | 2000-02-17 |
US5440067A (en) | 1995-08-08 |
KR100267821B1 (ko) | 2000-10-16 |
IN186365B (ko) | 2001-08-18 |
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