KR930019596A - 알콜 또는 아민의 제조방법 - Google Patents

알콜 또는 아민의 제조방법 Download PDF

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KR930019596A
KR930019596A KR1019930002541A KR930002541A KR930019596A KR 930019596 A KR930019596 A KR 930019596A KR 1019930002541 A KR1019930002541 A KR 1019930002541A KR 930002541 A KR930002541 A KR 930002541A KR 930019596 A KR930019596 A KR 930019596A
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호른 게르하르트
디터 프로닝 카를
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페티스, 라이헬트
훽스트 아크티엔게젤샤프트
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    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
    • F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
    • F25B43/00—Arrangements for separating or purifying gases or liquids; Arrangements for vaporising the residuum of liquid refrigerant, e.g. by heat
    • F25B43/04—Arrangements for separating or purifying gases or liquids; Arrangements for vaporising the residuum of liquid refrigerant, e.g. by heat for withdrawing non-condensible gases
    • F25B43/043—Arrangements for separating or purifying gases or liquids; Arrangements for vaporising the residuum of liquid refrigerant, e.g. by heat for withdrawing non-condensible gases for compression type systems
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/03—Precipitation; Co-precipitation
    • B01J37/031—Precipitation
    • 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
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
    • 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
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B01J35/391—Physical properties of the active metal ingredient
    • B01J35/392—Metal surface area
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
    • 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
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • 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
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/177—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of a carboxy group
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/613—10-100 m2/g
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/615—100-500 m2/g

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

Abstract

본 발명은 가압 및 승온에서 촉매에 의해 에스테르, 지방산 또는 니티릴을 수소와 반응시켜 알콜 또는 아민을 제조함에 있어서, 당해 촉매는 CuO 100중량부당 ZaO 40 내지 130중량부, Al2O32내지 50중량부 및 경우에 따라 Mn, Mo, V, Zr 및/또는 알카리 토금속의 산화물 0.5 내지 8중량부를 포함하고 환원되지 않은 상태에서 촉매 1g당 BET 총 면적(이때, BET총 며적의 75내지 95%는 반경(rp)이 15nm이하인 공극으로 형성된다)이 80내지 175m2인 방법에 관한 것이다.

Description

알콜 또는 아민의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (12)

  1. 에스테르, 지방산 또는 니트릴을 구리 함유 촉매(당해 촉매는 환원되지 않은 상태에서 CuO 100중량부당 ZnO 40내지 130중량부, Al2O32 내지 50중량부 및 경우에 따라 Mn, Mo, V,Zr 및/또는 알칼리 토금속의 산화물 0.5 내지 8중량부를 포함하고 환원되지 않은 상태에서 촉매 1g당 BET 총 면적 (이때, BET 총 면적의 75 내지 95%는 반경(rp)이 15mn이하인 공극으로 형성된다)이 80 내지 175m2이다.)의 존재하에 가압 및 승온에서 수소와 반응시켜 알콜 또는 아민을 제조하는 방법.
  2. 제1항에 있어서, 완원된 촉매의 활성 구리 금속 표면적이 Cu 1g당 30 내지 125m2, 특히 35 내지 100m2, 바람직하게는 40 내지 85m2방법.
  3. 제1항 또는 제2항에 있어서, 촉매가 환원되지 않은 상태에서 CuO 100중량부당 ZnO 45내지 100중량부, 특히 45내지 80중량부와 Al2O33내지 40중량부, 특히 4 내지 30중량부, 바람직하게는 4 내지 11중량부를 포함하는 방법.
  4. 제1항 내지 제3항중의 어느 한항에 있어서, 촉매의 BET 총 면적이 환원되지 않은 상태에서 촉매 1g당 85 내지 160m2, 특히 90 내지 155m2인 방법.
  5. 제1항 내지 제4항 중의 어느 한 항에 있어서, BET 총 면적의 80 내지 92%, 특히 84내지 90%가 반경(rp)이 15nm이하인 공극으로 형성된 방법.
  6. 제1항 내지 제5항 중의 어느 한 항에 있어서. 촉매가 CuO 100중량부당 수불용성 지지체, 특히 규조토 또는 실리카겔과 같은 SiO2및/또는 Al2O3를 2내지 80중량부, 특히 4내지 60중량부, 바람직하게는 5내지 35중량부 포함하는 방법.
  7. 제1항 내지 제6항중의 어느 한항에 있어서. 에스테르 또는 지방산이 200 내지 350℃ 측히 220내지 330℃,바람직하게는 230 내지 320℃의 온도및 15내지 40MPa, 특히 18 내지 35MPa, 바람직하게는 20내지 32MPa의 압력에서 반응하는 방법.
  8. 제1항 내지 제7항 중의 어느 한 항에 있어서, 카복실산의 에스테르, 특히 탄소수가 8 내지 30, 특히 10 내지 24, 바람직하게는 12 내지 22 인 천연적으로 발생하는 카복실산의 에스케르가 반응하는 방법.
  9. 제1항 내지 제7항중의 어느 한 항에 있어서. 탄소수가 8 내지 30, 특히 10 내지 24, 바람직하게는 12 내지 22인 지방산이 반응하는 방법.
  10. 제1항 내지 제6항중의 어느 한항에 있어서, 니트릴이 160 내지 250℃, 특히 190 내지 240℃, 바람직하게는 210 내지 230℃의 온도 및 0.5 내지 10MPa, 특히 1.0 내지 5.0MPa, 바람직하게는 1.2 내지 3.0MPa의 압력에서 반응하는 방법.
  11. 제1항 내지 제6항 및 제10항중의 어느 한 항에 있어서. 탄소수가 4 내지 30, 특히 8 내지 24, 바람직하게는 10 내지 22인 니트릴이 반응하는 방법.
  12. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930002541A 1992-03-04 1993-02-24 알콜의 제조방법 KR100283706B1 (ko)

Applications Claiming Priority (2)

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DE4206750A DE4206750A1 (de) 1992-03-04 1992-03-04 Verfahren zur herstellung von alkoholen oder aminen
DEP4206750.2 1992-03-04

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KR100283706B1 KR100283706B1 (ko) 2001-04-02

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EP (1) EP0559053B2 (ko)
JP (1) JP2721633B2 (ko)
KR (2) KR100283706B1 (ko)
CN (1) CN1040743C (ko)
CA (1) CA2090770C (ko)
DE (2) DE4206750A1 (ko)
ES (1) ES2103039T5 (ko)
MX (1) MX9301052A (ko)
MY (1) MY109406A (ko)
SG (1) SG44835A1 (ko)

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MY129140A (en) * 1994-11-07 2007-03-30 Shell Int Research Process and a catalyst for the direct hydrogenation of carboxylic esters
KR100457066B1 (ko) * 2002-04-22 2004-11-12 애경유화 주식회사 수소화 반응촉매 및 그의 제조방법, 및 이 촉매를이용하여 무수말레인산으로부터 감마-부티로락톤을제조하는 방법
US20150018572A1 (en) * 2012-03-13 2015-01-15 Benefuel Inc. Solid Acid Catalyst, Method of Manufacturing the Same and Method of Manufacturing Fatty Acid Alkyl Ester Using the Same
DE102014013530A1 (de) 2014-09-12 2016-03-17 Clariant International Ltd. Extrudierter Cu-Al-Mn-Hydrierkatalysator
EP3294453A4 (en) * 2015-03-26 2018-10-24 BASF Corporation Hydrogenolysis catalysts with high acid tolerance
GB201905293D0 (en) * 2019-04-15 2019-05-29 Johnson Matthey Plc Copper-containing catalysts

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EP0175558A1 (en) * 1984-09-17 1986-03-26 EASTMAN KODAK COMPANY (a New Jersey corporation) Process for the vapor phase hydrogenation of carboxylic acids to esters and alcohols
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US5008235A (en) * 1989-12-21 1991-04-16 Union Carbide Chemicals And Plastics Technology Corporation Catalysts of Cu-Al-third metal for hydrogenation

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EP0559053A3 (ko) 1994-04-13
DE59306359D1 (de) 1997-06-12
CA2090770C (en) 1999-06-29
MX9301052A (es) 1993-09-01
EP0559053B2 (de) 2005-12-14
JPH069452A (ja) 1994-01-18
JP2721633B2 (ja) 1998-03-04
ES2103039T3 (es) 1997-08-16
EP0559053B1 (de) 1997-05-07
ES2103039T5 (es) 2006-06-01
CN1076438A (zh) 1993-09-22
EP0559053A2 (de) 1993-09-08
KR100283975B1 (ko) 2001-02-15
US5550297A (en) 1996-08-27
MY109406A (en) 1997-01-31
DE4206750A1 (de) 1993-09-09
CA2090770A1 (en) 1993-09-05
KR100283706B1 (ko) 2001-04-02
US5663445A (en) 1997-09-02
CN1040743C (zh) 1998-11-18
SG44835A1 (en) 1997-12-19

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