KR940014286A - 알데히드의 제조방법 - Google Patents

알데히드의 제조방법 Download PDF

Info

Publication number
KR940014286A
KR940014286A KR1019930027167A KR930027167A KR940014286A KR 940014286 A KR940014286 A KR 940014286A KR 1019930027167 A KR1019930027167 A KR 1019930027167A KR 930027167 A KR930027167 A KR 930027167A KR 940014286 A KR940014286 A KR 940014286A
Authority
KR
South Korea
Prior art keywords
carbon atoms
radical
different
same
catalyst
Prior art date
Application number
KR1019930027167A
Other languages
English (en)
Other versions
KR100280760B1 (ko
Inventor
바르만 헬무트
라페 페터
Original Assignee
페터스, 라이헬트
훽스트 아크티엔게젤샤프트
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 페터스, 라이헬트, 훽스트 아크티엔게젤샤프트 filed Critical 페터스, 라이헬트
Publication of KR940014286A publication Critical patent/KR940014286A/ko
Application granted granted Critical
Publication of KR100280760B1 publication Critical patent/KR100280760B1/ko

Links

Classifications

    • 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
    • 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
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0239—Quaternary ammonium compounds
    • 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
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
    • B01J31/0268—Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • 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
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/10—Non-coordinating groups comprising only oxygen beside carbon or hydrogen
    • B01J2540/12—Carboxylic acid 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
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/30—Non-coordinating groups comprising sulfur
    • B01J2540/32—Sulfonic acid groups or their salts

Abstract

본 발명은 촉매로서 수용성 로듐-포스핀 착화합물 및 가용화제로서 4급 포스포늄 화합물의 염을 포함하는 수용액의 존재하에 액상으로 수행하는 올레핀의 하이드로포밀화 방법에 관한 것이다.

Description

알데히드의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (8)

  1. 일산화탄소 및 수소를 촉매로서의 수용성 로듐-포스핀 착화합물 및 가용화제 [여기서, 가용화제는 4급 포스포늄 화합물의 염이다]를 포함하는 수용액과 존재하에서 C6-내지 C20-올레핀과 액상으로 반응시킴으로써 알데히드를 제조하는 방법.
  2. 제 1 항에 있어서, 포스포늄 염이 하기 일반식의 화합물인 방법.
    상기식에서, A는 각각의 경우에 탄소원자수가 6 내지 18인 알킬 또는 아릴 라디칼이고, B,C 및 D는 탄소원자수가 1 내지 4인 직쇄 또는 측쇄의 알킬 라디칼이며, E는 음이온을 나타낸다.
  3. 제 2 항에 있어서, 포스포늄 염의 음이온이 할라이드, 설페이트, 테트라플루오로보레이트, 아세테이트, 메토설페이트, 벤젠술포네이트, 톨루엔설포네이트, 락테이트, 또는 시트레이트인 방법.
  4. 제 2 항에 있어서, 포스포늄 염의 음이온이 착화합물의 성분으로서 사용된 설폰화 또는 카복실화 포스핀인 방법.
  5. 제 1 항 내지 제 4 항 중의 어느 한 항에 있어서, 촉매로서 사용된 로듐 화합물이, 착체로서 결합된, 일반식(1)의 트리설폰화 및/또는 트리카복실화 트리아릴포스핀을 포함하는 방법.
    상기식에서, Ar1, Ar2및 Ar3은 각각 페닐 또는 나프틸 그룹이고, Y1, Y2및 Y3은 각각 탄소원자수가 1 내지 4인 직쇄 또는 측쇄 알킬 그룹, 알콕시 그룹, 할로겐 원자, OH, CN, NO2또는 R1R2N그룹 [여기서, Ru및 R2는 각각 탄소원자수가 1 내지 4인 직쇄 또는 측쇄 알킬 그룹이다]이고, X1, X2및 X3은 각각의 경우에 카복실레이트(COO-) 및/또는 설포네이트 (SO3 -)라디칼이고, n1, n2 및 n3은 동일하거나 상이하고, 0 내지 5의 정수이며, M은 알칼리 금속, 알칼리 토금속, 아연, 암모늄 또는 일반식 N(R3R4R5R6)+의 4급 암모늄 이온 [여기서, R3, R4, R5및 R6은 각각 탄소원자수가 1 내지 4인 직쇄 또는 측쇄 알킬 그룹이다]이다.
  6. 제 5 항에 있어서, Ar1, Ar2및 Ar3이 각각 페닐 라디칼이고, X1, X2및 X3이 각각 설포네이트 라디칼인 방법.
  7. 제 1 항 내지 제 5 항 중의 어느 한 항에 있어서, 촉매로서 사용된 로듐 화합물이, 착체로서 결합된, 하나 이상의 설포네이트(SO3 -) 라디칼 또는 카볼실레이트(COO-) 라디칼에 의해 치환된 하기 일반식(2)의 디아릴 화합물을 포함하는 방법.
    상기식에서, R1은 각각 동일하거나, 상이하고, 알킬, 사이클로알킬, 페닐 톨릴 또는 나프틸 라디칼이고, R2는 동일하거나 상이하고, 수소, 탄소원자수 1 내지 14의 알킬 또는 알콕시 라디칼, 탄소원자수 6 내지 15의 사이클로알킬, 아릴 또는 아르옥시 라디칼, 또는 융합된 벤젠 환이고, m은 동일하거나 상이하고, 0 내지 5의 정수이며, n은 유사하게 동일하거나 상이하고, 0 내지 4의 정수이다.
  8. 제 1 항 내지 제 7 항 중의 어느 한 항에 있어서, 수성 촉매 용액 중의 가용화제의 농도가 촉매 용액을 기준으로 하여 0.5 내지 10중량%인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930027167A 1992-12-17 1993-12-10 알데히드의 제조방법 KR100280760B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4242723A DE4242723A1 (de) 1992-12-17 1992-12-17 Verfahren zur Herstellung von Aldehyden
DEP4242723.1 1992-12-17

Publications (2)

Publication Number Publication Date
KR940014286A true KR940014286A (ko) 1994-07-18
KR100280760B1 KR100280760B1 (ko) 2001-02-01

Family

ID=6475614

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019930027167A KR100280760B1 (ko) 1992-12-17 1993-12-10 알데히드의 제조방법

Country Status (11)

Country Link
US (1) US5367107A (ko)
EP (1) EP0602463B1 (ko)
JP (1) JP2577187B2 (ko)
KR (1) KR100280760B1 (ko)
AU (1) AU661257B2 (ko)
BR (1) BR9305009A (ko)
CA (1) CA2111032C (ko)
DE (2) DE4242723A1 (ko)
ES (1) ES2096187T3 (ko)
MX (1) MX9307867A (ko)
TW (1) TW243442B (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100521661B1 (ko) * 1996-08-13 2005-12-30 셀라네제 쉐미칼스 오이로페 게엠베하 균질한하이드로포르밀화의반응혼합물로부터포스틴옥사이드와알킬아릴포스핀을분리하는방법

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4440552A1 (de) * 1994-11-12 1996-05-15 Hoechst Ag Verfahren zur Herstellung von Formylcarbonsäureestern
FR2727637B1 (fr) * 1994-12-06 1997-01-03 Rhone Poulenc Chimie Procede de preparation electrochimique de catalyseurs a base de metal de transition et de phosphine
FR2735399B1 (fr) * 1995-06-16 1997-07-25 Inst Francais Du Petrole Nouvelle composition catalytique a base de complexes de metaux de transition et procede pour l'hydrogenation des composes insatures
FR2743010B1 (fr) * 1995-12-29 1998-02-20 Rhone Poulenc Fibres Procede de preparation par hydrogenation de catalyseurs a base de metal de transition et de phosphine
DE19610869A1 (de) * 1996-03-20 1997-09-25 Hoechst Ag Verfahren zur Herstellung von Aldehyden
DE19625168A1 (de) * 1996-06-24 1998-01-08 Hoechst Ag Katalysator und ein Verfahren zur Herstellung von Aldehyden in Gegenwart dieses Katalysators
FR2813305B1 (fr) * 2000-08-23 2004-02-13 Inst Francais Du Petrole Procede ameliore d'hydroformylation mettant en oeuvre un catalyseur a base de cobalt et/ou de rhodium dans un solvant ionique non aqueux
GR20000100460A (el) * 2000-12-27 2002-10-09 Celanese Chemicals Europe Gmbh Μεθοδος για την παρασκευη αλδευδων
KR101559082B1 (ko) 2013-12-18 2015-10-08 한화케미칼 주식회사 올레핀계 화합물의 하이드로포밀화 반응용 수용성 촉매 조성물

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US526942A (en) 1894-10-02 Food-screen
US4013700A (en) * 1974-11-25 1977-03-22 Union Carbide Corporation Catalytic process for polyhydric alcohols and derivatives
JPS6332079B2 (ko) * 1979-02-12 1988-06-28 Exxon Research Engineering Co
GB2085874B (en) * 1980-09-04 1984-08-08 Johnson Matthey Plc Hydroformylation of olefins
EP0107430B1 (en) * 1982-10-21 1986-08-13 Texaco Development Corporation Method for the preparation of alcohols and aldehydes by reacting olefins with carbon monoxide and hydrogen
US4599206A (en) * 1984-02-17 1986-07-08 Union Carbide Corporation Transition metal complex catalyzed reactions
US4945185A (en) * 1987-12-24 1990-07-31 Union Carbide Chemicals And Plastics Company Inc. Process for producing mixtures of ketones and aldehydes
US4960949A (en) * 1988-12-22 1990-10-02 Eastman Kodak Company Low pressure rhodium catalyzed hydroformylation of olefins

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100521661B1 (ko) * 1996-08-13 2005-12-30 셀라네제 쉐미칼스 오이로페 게엠베하 균질한하이드로포르밀화의반응혼합물로부터포스틴옥사이드와알킬아릴포스핀을분리하는방법

Also Published As

Publication number Publication date
CA2111032C (en) 2000-05-02
US5367107A (en) 1994-11-22
CA2111032A1 (en) 1994-06-18
AU661257B2 (en) 1995-07-13
DE59304480D1 (de) 1996-12-19
MX9307867A (es) 1994-06-30
EP0602463B1 (de) 1996-11-13
AU5243793A (en) 1994-06-30
ES2096187T3 (es) 1997-03-01
DE4242723A1 (de) 1994-06-23
EP0602463A1 (de) 1994-06-22
JPH06293692A (ja) 1994-10-21
TW243442B (ko) 1995-03-21
JP2577187B2 (ja) 1997-01-29
BR9305009A (pt) 1994-07-05
KR100280760B1 (ko) 2001-02-01

Similar Documents

Publication Publication Date Title
KR940014286A (ko) 알데히드의 제조방법
KR850008480A (ko) 알데히드의 제조방법
SE8704533D0 (sv) Hydroformylation using low volatile phosphine ligands
RU2000132219A (ru) Металлоорганические комплексы, способ их получения, катализатор гидроформилирования на их основе и промежуточный продукт
KR970700156A (ko) 5-포르밀발레르 산 및 5-포르밀발러레이트 에스테르의 제조 방법(process for the preparation of 5-formylvaleric acid and 5-formylvalerate ester)
KR880001557A (ko) 저휘발성/유기 가용성 포스핀 리간드를 사용한 하이드로 포밀화 방법
KR910011727A (ko) 알데히드의 제조공정
Brown et al. Hydroformylation catalysed by rhodium complexes of trehalose-derived ligands aa and ββ-tredip; a highly recioselective route to α-methylarylpropionaldehydes
KR860000237A (ko) 알데히드의 제조방법
AU598502B2 (en) Process for the preparation of aldehydes
ATE244213T1 (de) Verfahren zur herstellung von aldehyden
CA1337098C (en) Process for recovering rhodium
JPS63150239A (ja) アルデヒドの製法
DE3870078D1 (de) Verfahren zur herstellung von aldehyden.
KR970015552A (ko) 펜텐알의 제조방법
US6069253A (en) Process for the preparation of new transition metal complexes
KR970065496A (ko) 알데히드의 제조방법
KR960005498B1 (ko) 수용성 히드로포르밀화 촉매의 재활성화 방법
US4593011A (en) Hydroformylation process using triarylphosphine and bisphosphine monooxide ligands
KR960022426A (ko) 알데히드의 제조방법
US4522933A (en) Hydroformylation catalyst containing bisphosphine monooxide ligands
JP2002533467A (ja) 水溶性スルホン化有機燐化合物の製造法、及び二相触媒反応実施する有機反応
Nonoyama et al. Cyclopalladation compounds of the 2-pyridylhydrazone derivatives of p-substituted acetophenones and acetylthiophenes
CA2245486A1 (en) Hydroformylation process
Yang et al. X-ray diffraction structure of the 1, 1′-bis (diphenylphosphino) ferrocene (dppf)-bridged complex [(dppf) AgCl] 2: An unexpected product from the reaction between cis-(bpy) 2RuCl2 and dppf in the presence of AgBF4

Legal Events

Date Code Title Description
A201 Request for examination
N231 Notification of change of applicant
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
LAPS Lapse due to unpaid annual fee