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KR970704672A - 아크릴로니트릴의 2량화반응생성물의 제조방법 - Google Patents

아크릴로니트릴의 2량화반응생성물의 제조방법

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Publication number
KR970704672A
KR970704672A KR1019970700932A KR19970700932A KR970704672A KR 970704672 A KR970704672 A KR 970704672A KR 1019970700932 A KR1019970700932 A KR 1019970700932A KR 19970700932 A KR19970700932 A KR 19970700932A KR 970704672 A KR970704672 A KR 970704672A
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KR
South Korea
Prior art keywords
dimerization reaction
producing
reaction product
acrylonitrile
product according
Prior art date
Application number
KR1019970700932A
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English (en)
Inventor
야수히꼬 쓰즈끼
요시히사 끼소
Original Assignee
고다 시게노리
미쓰이세키유 가가쿠고교 가부시끼가이샤
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Application filed by 고다 시게노리, 미쓰이세키유 가가쿠고교 가부시끼가이샤 filed Critical 고다 시게노리
Publication of KR970704672A publication Critical patent/KR970704672A/ko

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2291—Olefins
    • 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
    • C07C255/06—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and unsaturated carbon skeleton
    • C07C255/09—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and unsaturated carbon skeleton containing at least two cyano groups bound to the carbon skeleton
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • B01J31/146—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of boron
    • 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
    • B01J31/22—Organic complexes
    • 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
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • 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
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • 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
    • 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • 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
    • B01J2531/821—Ruthenium
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • 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
    • 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
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    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

고활성으로 우수한 촉매를 사용하고, 분리곤란한 부생생물을 발생시키지 않고, 아크릴로니트릴의 직쇄 2량체를 간단하게 효율 좋고, 또 고수율로 제조할 수 있는 공업적으로 바람직한 제조방법을 제공한다.
루테늄을 중심원자로서 시클로펜타디엔 또는 그 유도체가 배위된 루테늄착체의 존재하에 아크릴로니트릴을 반응시킨다.
생성물의 아디포니트릴, 1,4-디시아노부텐 또는 1,4-디시아노부타디엔은 나일론-66 원료인 헥사메틸렌디아민 및 아디핀산의 중간체로서 또는 녹방지제, 고무의 가황촉진제 등의 중간체로서 유용한 화합물이다.

Description

아크릴로니트릴의 2량화반응생성물의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (9)

  1. 루테늄을 중심원자로서 시클로펜타디엔 또는 그 유도체가 배위된 루테늄착체의 존재하에 아크릴로니트릴을 2량화반응 시키는 공정을 포함하는 것이 특징인 아크릴로니트릴의 2량화반응 생성물의 제조방법.
  2. 제1항에 있어서, 2량화 반응을 수소공존하에서 행하는 것이 특징인 2량화반응생성물의 제조방법.
  3. 제1항 또는 제2항에 있어서, 루테늄착체는 시클로펜타디엔 또는 그 유도체의 외에 RD(R은 탄화수소기임)로 표시되는 옥시탄화수소기가 배위되어 있는 것이 특징인 2량화반응생성물의 제조방법.
  4. 제3항에 있어서, 옥시탄화수소기가 알콕실기인 것이 특징인 2량화반응 생성물의 제조방법.
  5. 제4항에 있어서, 알콕실기가 에톡시기인 것이 특징인 2량화반응 생성물의 제조방법.
  6. 제1항 또는 제2항에 있어서, 루테늄착체는 시클로펜타디엔 또는 그 유도체외에 할로겐원자 및/또는 올레핀화합물이 배위되어 있는 것이 특징인 2량화반응생성물의 제조방법.
  7. 제6항에 있어서, 2량화반응을 루테늄착체외에 금속염 및/또는 환원제의 공존하에서 행하는 것이 특징인 2량화반응생성물의 제조방법.
  8. 제1항 내지 제7항 중 어느 한 항에 있어서, 아크릴로니트릴의 2량화반응에서 의해서 얻은 화합물이 아디포니트릴,1,4-디시아노부텐 및 1,4-디시아노부타디엔으로 되는 군으로부터 선택된 1이상의 화합물인 것이 특징인 2량화반응생성물의 제조방법.
  9. 제1항 내지 제8항 중 어느 한 항에 있어서, 2량화 반응을 용매로서 지방족알콜을 사용하여 행하는 것이 특징인 2량화반응생성물의 제조방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019970700932A 1995-06-29 1996-06-26 아크릴로니트릴의 2량화반응생성물의 제조방법 KR970704672A (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP16433995 1995-06-29
JP164339 1995-06-29
PCT/JP1996/001760 WO1997001531A1 (fr) 1995-06-29 1996-06-26 Procede de production de dimeres d'acrylonitrile

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KR970704672A true KR970704672A (ko) 1997-09-06

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KR1019970700932A KR970704672A (ko) 1995-06-29 1996-06-26 아크릴로니트릴의 2량화반응생성물의 제조방법

Country Status (7)

Country Link
US (1) US5922901A (ko)
EP (1) EP0795542B1 (ko)
KR (1) KR970704672A (ko)
CN (1) CN1047164C (ko)
CA (1) CA2198081A1 (ko)
DE (1) DE69608657T2 (ko)
WO (1) WO1997001531A1 (ko)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002022560A1 (fr) * 2000-09-11 2002-03-21 Ube Industries, Ltd. 4,8-dodecadienedinitrile et son procede de fabrication
GB0504851D0 (en) * 2005-03-09 2005-04-13 E2V Tech Uk Ltd Biosensor labelling groups

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR89767E (fr) * 1965-03-18 1967-08-18 Rhone Poulenc Sa Procédé de dimérisation linéaire de l'acrylonitrile
JPS52133968A (en) * 1976-05-06 1977-11-09 Japan Synthetic Rubber Co Ltd Cyclopentadiene derivatives
US4422980A (en) * 1981-08-10 1983-12-27 Standard Oil Company Acrylic dimerization using supported catalysts
DE3337294A1 (de) * 1983-10-13 1985-04-25 Bayer Ag, 5090 Leverkusen Verfahren zur selektiven hydrierung von c-c-doppelbindungen in gegenwart von reduzierbaren, stickstoffhaltigen gruppen und neue ruthenium-komplexverbindungen
JP2830959B2 (ja) * 1991-08-23 1998-12-02 宇部興産株式会社 アクリロニトリル二量体の製法
DE69302844T2 (de) * 1992-03-06 1996-10-24 Ube Industries Verfahren zur Herstellung von geradkettigen Acrylnitril-Dimeren
JP3317038B2 (ja) * 1993-09-03 2002-08-19 宇部興産株式会社 アクリロニトリル二量体の製造法
JPH08245539A (ja) * 1995-03-15 1996-09-24 Asahi Chem Ind Co Ltd アクリロニトリル二量体の製造方法

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Publication number Publication date
CN1163607A (zh) 1997-10-29
DE69608657D1 (de) 2000-07-06
WO1997001531A1 (fr) 1997-01-16
US5922901A (en) 1999-07-13
EP0795542B1 (en) 2000-05-31
EP0795542A1 (en) 1997-09-17
CN1047164C (zh) 1999-12-08
DE69608657T2 (de) 2001-02-08
CA2198081A1 (en) 1997-01-16
EP0795542A4 (en) 1999-04-07

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