KR840001119A - 하이드람포로밀화에 의한 알데히드의 제조방법 - Google Patents

하이드람포로밀화에 의한 알데히드의 제조방법 Download PDF

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KR840001119A
KR840001119A KR1019820003668A KR820003668A KR840001119A KR 840001119 A KR840001119 A KR 840001119A KR 1019820003668 A KR1019820003668 A KR 1019820003668A KR 820003668 A KR820003668 A KR 820003668A KR 840001119 A KR840001119 A KR 840001119A
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조오지 아바트조글로우 안토니 (외 1)
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에드워드 지. 그리어
유니온 카및이드 코포레이션
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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
    • B01J31/24—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
    • B01J31/2495—Ligands comprising a phosphine-P atom and one or more further complexing phosphorus atoms covered by groups B01J31/1845 - B01J31/1885, e.g. phosphine/phosphinate or phospholyl/phosphonate ligands
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO 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
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • 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
    • B01J2531/822—Rhodium
    • 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
    • B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=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
    • B01J31/16—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

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
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  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

내용 없음

Description

하이드람포로밋화에 의한 알데히드의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (16)

  1. 올레핀성 불포화화합물을, 가용성 로듐-포스포러스 배위자 착염 촉매 및 유리 포스포러스 배위자가 함유된 반응 매체내에서 일산화탄소 및 수소와 하이드로포르밀화 반응시켜 알데히드를 제조함에 있어서, 상기 착염촉매의 포스포러스 배위자 및 유리 포스포러스 배위자로서 다음 일반식의 유기 3급 비스포스핀 모노옥사이드 배위자를 사용함을 특징으로 하는 개선된 하이드로포르밀화방법에 의한 알데히드의 제조방법.
    상기 일반식에서
    Ar은 같거나 다르며, 각각 치환 또는 비치환된 아릴기이고
    R1및 R2는 같거나 다르며, 각각 치환 또는 비치환된 1가의 탄화수소기이고 Y는 2가의 가교기이다.
  2. 제1항에 있어서, 온도가 45°내지 200℃, 수소, 일산화탄소 및 올레핀성 불포화 화합물의 총가스압력이 500psia이하, 일산화탄소의 분압이 1내지 50psia, 수소의 분압이 20내지 200psia가 되도록 하이드로포르밀화반응조건을 조절하고, 상기 반응 매체가 매체 내 촉매적 활성 로듐 금속 몰당 3내지 80몰의 유리유기 3급 비스포스핀 모노옥사이드 배위자를 함유하는 방법.
  3. 제1항에 있어서, Ar기가 같거나 다르며, 각각 탄소수 6내지 12의 치환 또는 비치환된 4아릴기를 나타내고, R1및 R2가 같거나 다르며, 각각 탄소수 1내지 30의 치환 또는 비치환된 1가의 탄화수소기로서 알킬, 아릴, 알크아릴, 아르알킬 또는 지환족기를 나타내고, Y가 탄소수 1내지 30의 2가의 가교기로서 탄화수소기, 산소함유 탄화수소기, 황함유 탄화수소기 또는 질소함유 탄화수소기를 나타내는 방법.
  4. 제3항에 있어서, R1및 R2가 탄소수 1내지 12의 알킬기 및 탄소수 6내지 12의 아릴기중에서 선택된, 치환 또는 비치환된 1가의 탄화수소기이고 Y가 1내지 12개의 탄소수를 함유하는 방법.
  5. 제4항에 있어서, Ar기가 각각 비치환된 아릴기이고 R1및 R2가 비치환된 알킬 또는 아릴기이고 Y가 2가의 탄화수소기인 방법.
  6. 제5항에 있어서, 상기 비스포스핀 모노옥사이스가 다음 구조식의 배위자인 방법.
    상기 일반식에서
    n은 2내지 8의 정수이다.
  7. 제6항에 있어서, n이 2인 방법
  8. 주로 용해된 로듐 카보닐 비스포스핀 모노옥사이드 아세틸아세토네이트 착염, 유기용매 및 유리 비스포스핀모노옥사이드 배위자로 이루어지며 상기 착염의 비스포스핀 모노옥사이드와 상기 유리 비스포스핀 모노옥사이드 배위자가 다음 일반식의 유기 3급 비스포스핀 모노옥사이드 배위자인로듐 착염 하이드로포르밀화 촉매 전구체 조성물.
    상기 일반식에서
    Ar은 같거나 다르며, 각각 치환 또는 비치환된 아릴기이고
    R1및 R2는 같거나 다르며, 각각 치환 또는 비치환된 1가의 탄화수소기이고 Y는 2가의 가교기이다.
  9. 제8항에 있어서, Ar기가 같거나 다르며, 각각 탄소수 6내지 12의 치환 또는 비치환된 아릴기를 나타내고, R1및 R2가 같거나 다르며, 각각 탄소수 1내지 30의 치환 또는 비치환된 1가의 탄화수소기로서 알킬, 아릴, 알크아릴, 아르알킬 또는 지환족기를 나타내고 Y가 탄소수 1내지 30의 2가의 가교기로서 탄화수소기, 산소함유 탄화수소기, 황함유 탄화수소기 또는 질소함유 탄화수소기를 나타내는 조성물.
  10. 제9항에 있어서, 로듐 디카보닐 아세틸아세토네이트 형태로 도입되는 50내지 400ppm의 로듐(유리금속으로서계산), 로듐몰당 3내지 80몰의 유리비스포스핀 모노옥사이드 배위자와 전구체 조성물 총중량을 기준하여 5내지 95중량%의 용매를 함유하는 조성물.
  11. 제10항에 있어서, R1및 R2가 탄소수 1내지 12의 알킬기 및 탄소수 6내지 12의 아릴기중에서 선택된 치환 또는 비치환된 1가의 탄화수소기이고 Y가 1내지 12개의 탄소수를 함유하는 조성물.
  12. 제11항에 있어서, Ar기가각각 비치환된 아릴기이고 R1및 R2가 비치환된 알킬 또는 아릴기이고 Y가 2가의 탄화수소기인 조성물.
  13. 제12항에 있어서, 상기 유기 3급 비스포스핀 모노옥사이드 배위자가 다음 구조식의 배위자인조성몰.
    상기 일반식에서
    n은 2내지 8의 정수이다.
  14. 제13항에 있어서, n이 2인 조성물.
  15. 제1항에 있어서, 올레핀성 불포화화합물이 2내지 20개의 탄소수를 함유하는 방법.
  16. 제3항에 있어서, 올레핀성 불포화 화합물이 탄소수 4내지 20의 α-알켄 또는 탄소수 4내지 20의 작용성올 레핀인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR8203668A 1981-08-17 1982-08-16 하이드로포르밀화에 의한 알데히드의 제조방법 KR870000201B1 (ko)

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US293,190 1981-08-17
US06/293,190 US4400548A (en) 1981-08-17 1981-08-17 Hydroformylation process using bisphosphine monooxide ligands
US293190 1981-08-17

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KR840001119A true KR840001119A (ko) 1984-03-28
KR870000201B1 KR870000201B1 (ko) 1987-02-16

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US (1) US4400548A (ko)
EP (1) EP0073961B1 (ko)
JP (1) JPS5839636A (ko)
KR (1) KR870000201B1 (ko)
CA (1) CA1183122A (ko)
DE (1) DE3265617D1 (ko)

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EP0073961A1 (en) 1983-03-16
KR870000201B1 (ko) 1987-02-16
CA1183122A (en) 1985-02-26
US4400548A (en) 1983-08-23
DE3265617D1 (en) 1985-09-26
JPS5839636A (ja) 1983-03-08
EP0073961B1 (en) 1985-08-21

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