KR970010721A - 시클로헥산올 및 시클로헥산온의 제조방법 - Google Patents

시클로헥산올 및 시클로헥산온의 제조방법 Download PDF

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KR970010721A
KR970010721A KR1019950026858A KR19950026858A KR970010721A KR 970010721 A KR970010721 A KR 970010721A KR 1019950026858 A KR1019950026858 A KR 1019950026858A KR 19950026858 A KR19950026858 A KR 19950026858A KR 970010721 A KR970010721 A KR 970010721A
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South Korea
Prior art keywords
cyclohexanone
cyclohexanol
iron
palladium
weight
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KR1019950026858A
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English (en)
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KR0169189B1 (ko
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전기원
김상범
김성보
이규완
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강박광
제단법인 한국화학연구소
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Priority to KR1019950026858A priority Critical patent/KR0169189B1/ko
Priority to JP51013997A priority patent/JP3218044B2/ja
Priority to DE69522968T priority patent/DE69522968T2/de
Priority to EP95940477A priority patent/EP0857169B1/en
Priority to PCT/KR1995/000162 priority patent/WO1997008119A1/en
Priority to US09/029,661 priority patent/US6075170A/en
Publication of KR970010721A publication Critical patent/KR970010721A/ko
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Publication of KR0169189B1 publication Critical patent/KR0169189B1/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—Iron group metals
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
    • C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/303—Saturated compounds containing keto groups bound to rings to a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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

Abstract

본 발명은 시클로헥산올 및 시클로헥산온의 제조방법에 관한 것으로서, 더욱 상세하게는 아세톤과 아세트산의 혼합용매 중에서 철-팔라듐 2중 촉매를 사용하고 산소와 수소 기체의 존재하에 시클로헥산을 선택적으로 산화시켜 시클로헥산올 및 시클로헥산온을 동시에 제조하는 방법에 관한 것이다.

Description

시클로헥산올 및 시클로헥산온의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 반응매체에 산소의 수소기체를 통과시켜 주면서 철-팔라듐 촉매 존재하에 시클로헥산을 산화시켜 시클로헥산올과 시클로헥산온을 제조함에 있어서, 상기 반응매체로 아세톤 1 중량부와 아세트산 0.05∼1.5중량부를 혼합한 혼합용액을 사용하는 것을 특징으로 하는 시클로헥산올과 시클로헥산온의 제조방법.
  2. 제1항에 있어서, 상기 반응매체는 철-팔라듐 촉매 대하여 4∼50중량배 사용하는 것을 특징으로 하는 시클로헥산올과 시클로헥산온의 제조방법.
  3. 제1항에 있어서, 상기 시클로헥산은 철-팔라듐 촉매 대하여 1∼20중량배 사용하는 것을 특징으로 하는 시클로헥산올과 시클로헥산온의 제조방법.
  4. 제1항에 있어서, 상기 철-팔라듐 촉매로는 철(iron)계 화합물과 지지체에 지지된 팔라듐을 혼합 사용하는 것을 특징으로 하는 시클로헥산올과 시클로헥산온의 제조방법.
  5. 제4항에 있어서, 상기 철(iron)계 화합물로는 FeCl2, FeCl3, FeO, Fe2O3, FeSO4, Fe2(SO4)3및 Fe(OAc)2중에서 선택하여 사용하는 것을 특징으로 하는 시클로헥산올과 시클로헥산온의 제조방법.
  6. 제4항에 있어서, 상기 지지체로는 알루미나, 실리카, 실리카-알루미나 및 탄소 중에서 선택하여 사용하는 것을 특징으로 하는 시클로헥산올과 시클로헥산온의 제조방법.
  7. 제1항에 있어서, 상기 철-팔라듐 촉매로는 산화철(iron oxide)에 팔라듐 화합물을 침윤시킨 다음 건조하고 공기 또는 수소분위기에서 소성시켜 제조한 고체 촉매를 사용하는 것을 특징으로 하는 시클로헥산올과 시클로헥산온의 제조방법.
  8. 제7항에 있어서, 상기 산화철(iron oxide)으로는 FeO, Fe3O4또는 Fe2O3를 사용하는 것을 특징으로 하는 시클로헥산올과 시클로헥산온의 제조방법.
  9. 제7항에 있어서, 상기 팔라듐 화합물로는 염화팔라듐(PdCl2)또는 질산팔라듐[Pd(NO3)2]을 사용하는 것을 특징으로 하는 시클로헥산올과 시클로헥산온의 제조방법.
  10. 제7항에 있어서, 상기 고체촉매 1중량부를 시클로헥산 1∼20중량부, 아세톤과 아세트산 혼합용액 4∼50중량부 내에서 수소와 산소 혼합기체에 접촉시킨 후 80∼150℃에서 건조시켜 활성화시킨 것을 사용하는 것을 특징으로 하는 시클로헥산올과 시클로헥산온의 제조방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019950026858A 1995-08-28 1995-08-28 시클로헥산올 및 시클로헥산온의 제조방법 KR0169189B1 (ko)

Priority Applications (6)

Application Number Priority Date Filing Date Title
KR1019950026858A KR0169189B1 (ko) 1995-08-28 1995-08-28 시클로헥산올 및 시클로헥산온의 제조방법
JP51013997A JP3218044B2 (ja) 1995-08-28 1995-12-14 シクロヘキサノールおよびシクロヘキサノンの製造方法
DE69522968T DE69522968T2 (de) 1995-08-28 1995-12-14 Verfahren zur herstellung von cyclohexanol und cyclohexanon
EP95940477A EP0857169B1 (en) 1995-08-28 1995-12-14 Process for preparing cyclohexanol and cyclohexanone
PCT/KR1995/000162 WO1997008119A1 (en) 1995-08-28 1995-12-14 Process for preparing cyclohexanol and cyclohexanone
US09/029,661 US6075170A (en) 1995-08-28 1995-12-14 Process for preparing cyclohexanol and cyclohexanone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019950026858A KR0169189B1 (ko) 1995-08-28 1995-08-28 시클로헥산올 및 시클로헥산온의 제조방법

Publications (2)

Publication Number Publication Date
KR970010721A true KR970010721A (ko) 1997-03-27
KR0169189B1 KR0169189B1 (ko) 1999-03-20

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KR1019950026858A KR0169189B1 (ko) 1995-08-28 1995-08-28 시클로헥산올 및 시클로헥산온의 제조방법

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US (1) US6075170A (ko)
EP (1) EP0857169B1 (ko)
JP (1) JP3218044B2 (ko)
KR (1) KR0169189B1 (ko)
DE (1) DE69522968T2 (ko)
WO (1) WO1997008119A1 (ko)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002292282A (ja) * 2001-03-29 2002-10-08 Sud-Chemie Catalysts Inc シクロヘキサノール脱水素触媒及びその製造方法
US7358401B2 (en) 2005-03-31 2008-04-15 Sumitomo Chemical Company, Limited Method for manufacturing cycloalkanol and/or cycloalkanone

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2522322A1 (fr) * 1982-03-01 1983-09-02 British Petroleum Co Procede d'oxydation catalytique d'hydrocarbures paraffiniques en alcools
JPS6092236A (ja) * 1983-10-26 1985-05-23 Sumitomo Chem Co Ltd シクロヘキサノンの製造方法
IT1243772B (it) * 1990-08-01 1994-06-28 Eniricerche Spa Procedimento per l'ossidazione di composti paraffinici con ossigeno
KR950010785B1 (ko) * 1992-03-13 1995-09-23 재단법인한국화학연구소 시클로헥산올 및 시클로헥산온의 제조방법과 그에 사용되는 촉매

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JPH11509859A (ja) 1999-08-31
EP0857169B1 (en) 2001-09-26
DE69522968D1 (de) 2001-10-31
JP3218044B2 (ja) 2001-10-15
US6075170A (en) 2000-06-13
KR0169189B1 (ko) 1999-03-20
WO1997008119A1 (en) 1997-03-06
EP0857169A1 (en) 1998-08-12
DE69522968T2 (de) 2002-04-25

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