KR890700564A - 디올레핀의 선택적 히드로포르밀화 방법 - Google Patents

디올레핀의 선택적 히드로포르밀화 방법

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Publication number
KR890700564A
KR890700564A KR1019880701428A KR880701428A KR890700564A KR 890700564 A KR890700564 A KR 890700564A KR 1019880701428 A KR1019880701428 A KR 1019880701428A KR 880701428 A KR880701428 A KR 880701428A KR 890700564 A KR890700564 A KR 890700564A
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phenyl
formula
ethylphenyl
catalyst
ethylene
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KR1019880701428A
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English (en)
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KR960002599B1 (ko
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이소오 시미즈
야스오 마쯔무라
유다까 아라이
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기다야마 유다까
니혼 세끼유 가가꾸 가부시끼가이샤
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/50—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
    • C07C47/232—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/28—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/32—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings with a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
    • C07C5/333—Catalytic processes
    • C07C5/3332—Catalytic processes with metal oxides or metal sulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/245—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of keto groups or secondary alcohol groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/373—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in doubly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

내용 없음.

Description

디올레핀의 선택적 히드로포르밀화 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (11)

  1. 하기식(I)로 표시되는 (1-아릴에텐일)비닐벤젠을, 반응온도 : 40∼200℃, 반응압력 : 5kg/cm2이상의 조건에서 전이금속 카르보닐화 촉매의 존재하에 일산화탄소 및 수소와 반응시킴으로써 하기 식(II)로 표시되는 α-((1-아릴에텐일)페닐)프로피온알데히드를 제조하는 것을 특징으로하는 선택적 히드로포르밀화 방법.
    (식중, Ar은 비닐기 이외의 치환기로 치환될 수 있는 치환 아릴기)
  2. 제1항에 있어서, 3-(1-페닐에텐일)비닐벤젠을 전이금속 착체 카르보닐화 촉매의 존재하에 수소 및 일산화 탄소와 반응시킴으로써 α-(3-(1-페닐에텐일)페닐)프로피온알데히드를 제조하는 것을 특징으로하는 선택적 히드로포르밀화 방법.
  3. 제1항에 있어서, 상기식(I)의 (1-아릴에텐일)비닐벤젠이 하기 식(III)으로 표시되는 1, 1-디(치환아릴)에틸렌과의 혼합물인 것을 특징으로하는 방법.
    식중, Ar, Ar2는 동일 또는 상이한 치환 아릴기이고 모두 비닐기 이외의 치환기로 치환될 수 있다.
  4. 제3항에 있어서, 상기 식(III)의 1, 1-디(치환아릴)에틸렌이 1-페닐-1-에틸페닐에틸렌인 것을 특징으로하는 방법.
  5. 제3항에 있어서, 하기 공정(I) 및 공정(II)로 ((1-페닐에텐일)페닐)프로피온알데히드를 제조하는 것을 특징으로하는 방법. 공정(I) : 식(A)로 표시되는 1-페닐-1-에틸페닐-에탄을 비활성 기체의 공존하에 온도 400℃ 내지 650℃에 있어서 산화철계 및/또는 산화크롬계 탈수소 촉매와 접촉시켜 적어도 식(B)로 표시되는 1-페닐-1-에틸페닐-에틸렌 및 식(C)로 표시되는 1-페닐-1-비닐페닐-에틸렌을 함유하는 탈수소 반응물을 얻는 공정 및, 공정(II) : 상기 공정(I)에서 얻은 적어도 식(B)로 표시되는 1-페닐-1-에틸페닐-에틸렌 및 식(C)로 표시되는 1-페닐-1-비닐페닐-에틸렌을 함유하는 탈수소 반응물을 반응온도 : 40∼200℃, 반응압력 5kg/cm2이상의 조건하에서 전이금속 카르보닐화 촉매의 존재하에 일산화탄소 및 수소에 의해 히드로포르밀화하는 공정.
  6. 제5항에 있어서, 상기 공정(I)의 탈수소 촉매가 산화철 및/또는 산화크롬을 함유하는 탈수소 촉매인 것을 특징으로하는 방법.
  7. 제5항에 있어서, 상기 히드로포르밀화 공정후에 증류에 의해 고순도로((1-페닐에텐일)페닐)프로피온 알데히드를 함유하는 유분을 회수하는 것을 특징으로하는 방법.
  8. 제5항에 있어서, 상기 히드로포로밀화 공정후에 미반응분인 1-페닐-1-에틸페닐-에탄 및/또는 1-페닐-1-에틸페닐-에틸렌을 분리, 회수하고 이어서 상기 탈수소 공정(I)으로 되돌리는 것을 특징으로하는 방법.
  9. 제5항에 있어서, 1-페닐-1-에틸페닐-에탄이 에틸렌을 벤젠에 알칼화하는 것에 의하는 에틸벤젠을 제조함에 있어서 부생하는 중질분에서 회수된 1-페닐-1-에틸페닐-에탄을 함유하는 유분인 것을 특징으로 하는 방법.
  10. 제9항에 있어서, 알칼화에 쓰이는 촉매가 염화알루미늄 또는 합성 제올라이트 촉매인 것을 특징으로 하는 방법.
  11. 제1항 내지 제10항중 어느 한 항에 있어서, 전이금속 카르보닐화 촉매가 Pt, Rh, Ir, Ru, Co 및 Ni에서 선택되는 적어도 일종의 금속을 활성종으로 하는 촉매인 것을 특징으로하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880701428A 1987-03-12 1988-03-12 디올레핀의 선택적 히드로포르밀화 방법 KR960002599B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP62057098A JPH07100678B2 (ja) 1987-03-12 1987-03-12 α−（３−ベンゾイルフエニル）プロピオン酸の製造方法
JP62-57098 1987-03-12
PCT/JP1988/000263 WO1988007033A1 (en) 1987-03-12 1988-03-12 Process for selectively hydroformylating diolefin

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KR890700564A true KR890700564A (ko) 1989-04-25
KR960002599B1 KR960002599B1 (ko) 1996-02-23

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KR1019880002405A KR930010405B1 (ko) 1987-03-12 1988-03-08 α-(3-(1-페닐에테닐)페닐)프로피온알데히드
KR1019880701428A KR960002599B1 (ko) 1987-03-12 1988-03-12 디올레핀의 선택적 히드로포르밀화 방법

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US (2) US4889952A (ko)
EP (2) EP0282066B1 (ko)
JP (1) JPH07100678B2 (ko)
KR (2) KR930010405B1 (ko)
CA (1) CA1304401C (ko)
DE (2) DE3871410D1 (ko)
WO (1) WO1988007033A1 (ko)

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JPH07100678B2 (ja) * 1987-03-12 1995-11-01 日本石油化学株式会社 α−（３−ベンゾイルフエニル）プロピオン酸の製造方法
JPS63233945A (ja) * 1987-03-23 1988-09-29 Nippon Petrochem Co Ltd ジオレフインの選択的ヒドロフオルミル化方法
CA2005845C (en) * 1988-12-21 2001-01-09 Isoo Shimizu Method for preparing a-(4-isobutylphenyl) propionic acid or its precursor
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JPH07100679B2 (ja) * 1987-03-12 1995-11-01 日本石油化学株式会社 α−（３−ベンゾイルフエニル）プロピオン酸またはそのエステルの製造方法
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Also Published As

Publication number Publication date
EP0311689A4 (en) 1989-07-24
EP0282066A3 (en) 1989-09-27
US4982007A (en) 1991-01-01
CA1304401C (en) 1992-06-30
WO1988007033A1 (en) 1988-09-22
KR930010405B1 (ko) 1993-10-23
US4889952A (en) 1989-12-26
DE3871410D1 (de) 1992-07-02
EP0282066B1 (en) 1992-05-27
EP0282066A2 (en) 1988-09-14
JPH07100678B2 (ja) 1995-11-01
EP0311689A1 (en) 1989-04-19
KR880011061A (ko) 1988-10-26
DE3871898T2 (de) 1993-02-04
DE3871898D1 (de) 1992-07-16
EP0311689B1 (en) 1992-06-10
KR960002599B1 (ko) 1996-02-23
JPS63225334A (ja) 1988-09-20

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