KR830007611A - 1,4-부탄디올 및 테트라하이드로푸란의 제조방법 - Google Patents

1,4-부탄디올 및 테트라하이드로푸란의 제조방법 Download PDF

Info

Publication number
KR830007611A
KR830007611A KR1019810005041A KR810005041A KR830007611A KR 830007611 A KR830007611 A KR 830007611A KR 1019810005041 A KR1019810005041 A KR 1019810005041A KR 810005041 A KR810005041 A KR 810005041A KR 830007611 A KR830007611 A KR 830007611A
Authority
KR
South Korea
Prior art keywords
butyrolactone
weight
psi
oxygenated
maleic anhydride
Prior art date
Application number
KR1019810005041A
Other languages
English (en)
Other versions
KR880000544B1 (ko
Inventor
안토니 페사 프레드릭
마리 그래함 앤
Original Assignee
래리 윌리엄 에반스
더 스탠다드 오일 컴패니
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 래리 윌리엄 에반스, 더 스탠다드 오일 컴패니 filed Critical 래리 윌리엄 에반스
Publication of KR830007611A publication Critical patent/KR830007611A/ko
Application granted granted Critical
Publication of KR880000544B1 publication Critical patent/KR880000544B1/ko

Links

Classifications

    • 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
    • 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
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/60—Platinum group metals 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
    • B01J23/89—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
    • B01J23/8933—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 also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/8953—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 also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D307/08—Preparation of tetrahydrofuran

Landscapes

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

Abstract

내용 없음

Description

1,4-부탄디올 및 테트라하이드로푸란의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 말레산 무수물, 말레산, 썩신산 무수물, 썩신산, γ-부티로락톤 및 이들을 2이상 함유하는 혼합물 중에서 선택된 산소화 C4탄화수소를, 약 175℃ 내지 약 275℃의 온도 및 약 750psi내지 약 1500psi의 압력에서, 약 25중량% (산소화 탄화수소의 중량에 대한 비율임) 이하의 물 및 하기 구조식(I)의 촉매 존재하에, 수소와 접촉시켜 산소화 C4탄화수소로 부터 테트라하이드로푸란 및 1,4-부탄디올중 적어도 어느 하나를 제조하는 방법.
    (상기 구조식에서,
    M은 니켈과 팔라듐중 적어도 어느 하나이고,
    M′는 철, 코발트, 로듐, 오스뮴, 이리듐 및 백금중 적어도 어느 하나이고,
    M″는 아연과 카드뮴중 적어도 어느 하나이며
    x는 포함된 다른 원소들의 원자가 요구에 알맞는 숫자이다).
  2. γ-부티로락톤에 용해시킨 말레산 무수물 약 1내지 약 20중량% (혼합물의 총중량에 대한 비율)의 혼합물을, 약 230℃내지 약 250℃의 온도 및 약 1000psi내지 약 1300psi의 압력에서, 약 10중량%(산소화 탄화수소 혼합물의 총중량에 대한 비율) 이하의 물 및 하기 구조식(Ⅳ)의 촉매 존재하에, 수소와 접촉시켜 말레산 무수물로부터 1,4-부탄디올을 제조하는 방법.
    (상기 구조식에서,
    M은 니켈과 팔라듐 중 적어도 어느 하나이고,
    M′는 철, 코발트 및 로듐중 적어도 어느 하나이며,
    x는 포함된 다른 원소들의 원자가 요구에 알맞는 숫자이다).
  3. γ-부티로락톤을, 약 175℃ 내지 약 230℃의 온도 및 약 750psi 내지 약 1300psi의 압력에서 약 10중량% (γ-부티로락톤의 총중량에 대한 비율) 이하의 물 및 하기 구조식(V)의 촉매 존재하에 수소와 접촉시켜 γ-부티로 락톤으로 부터 테트라하이드로푸란을 제조하는 방법.
    (상기 구조식에서, M은 니켈과 팔라듐중 적어도 어느 하나이고,
    M′는 철, 코발트 및 로듐중 적어도 어느 하나이며
    x는 포함된 다른 원소들의 원자가 요구에 알맞는 숫자이다.)
  4. 특허청구범위 제1항에서, 루테늄의 몰비가 약 0.01내지 1.5이고, M 및 M′의 몰비가 약 0.1내지 1.5이며 M″의 몰비가 약 0.05내지 0.8인 제조방법.
  5. 특허청구범위 제4항에서, M′이 철, 코발트 또는 로듐인 제조방법.
  6. 특허청구범위 제5항에서 M″가 아연인 제조방법.
  7. 특허청구범위 제6항에서, M이 니켈인 제조방법.
  8. 특허청구범위 제7항에서, M′가 코발트인 제조방법.
  9. 특허청구범위 제8항에서, 산소화 C4탄화수소가 말레산 무수물, γ-부티로락톤 또는 말레산 무수물과 γ-부티로 락톤의 혼합물인 제조방법.
  10. 특허청구범위 제9항에서, 산소화 C4가γ-부티로락톤에 용해시킨 약 1내지 약 20중량%(혼합물의 중량에 대한 비율임)의 말레산 무수물인 제조방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019810005041A 1980-12-22 1981-12-21 1,4-부탄디올 및 테트라하이드로푸란의 제조방법 KR880000544B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US06/218,856 US4301077A (en) 1980-12-22 1980-12-22 Process for the manufacture of 1-4-butanediol and tetrahydrofuran
US218856 1980-12-22
US218,856 1980-12-22

Publications (2)

Publication Number Publication Date
KR830007611A true KR830007611A (ko) 1983-11-04
KR880000544B1 KR880000544B1 (ko) 1988-04-13

Family

ID=22816767

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019810005041A KR880000544B1 (ko) 1980-12-22 1981-12-21 1,4-부탄디올 및 테트라하이드로푸란의 제조방법

Country Status (6)

Country Link
US (1) US4301077A (ko)
EP (1) EP0055512B1 (ko)
JP (1) JPS57109736A (ko)
KR (1) KR880000544B1 (ko)
CA (1) CA1157031A (ko)
DE (1) DE3166724D1 (ko)

Families Citing this family (64)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4863890A (en) * 1983-09-09 1989-09-05 Berol Kemi Ab Process for preparing a ruthenium-promoted, halogen-containing nickel and/or cobalt catalyst and a catalyst prepared by the process
SE461095B (sv) * 1983-09-09 1990-01-08 Berol Kemi Ab Amineringsfoerfarande med anvaendning av en ruteniumdopad nickel och/eller kovoltkatalysator
SE457608B (sv) * 1986-07-11 1989-01-16 Berol Kemi Ab Foerfarande foer framstaellning av en ruteniumdopad nickel- och/eller koboltkatalysator paa en poroes metalloxidbaerare samt anvaendning av katalysatorn i en hydrerings- och/eller dehydreringsreaktion
US4656297A (en) * 1985-03-11 1987-04-07 Amoco Corporation Coproduction of butanediol and tetrahydrofuran and their subsequent separation from the reaction product mixture
US4652685A (en) * 1985-11-15 1987-03-24 General Electric Company Hydrogenation of lactones to glycols
DE3610698A1 (de) * 1986-03-29 1987-10-01 Henkel Kgaa Katalysator und verfahren zur katalytischen hydrierung von fettsaeuremethylestern im festbett
GB8623233D0 (en) * 1986-09-26 1986-10-29 British Petroleum Co Plc Syngas conversion catalyst
US5149680A (en) * 1987-03-31 1992-09-22 The British Petroleum Company P.L.C. Platinum group metal alloy catalysts for hydrogenation of carboxylic acids and their anhydrides to alcohols and/or esters
US4810807A (en) * 1987-10-13 1989-03-07 The Standard Oil Company Hydrogenation of maleic anhydride to tetrahydrofuran
US4827001A (en) * 1987-11-02 1989-05-02 The Standard Oil Company Preparation of γ-butyrolactone and 1,4-butanediol by catalytic hydrogenation of maleic acid
US4885411A (en) * 1987-11-27 1989-12-05 Gaf Corporation Hydrogenation process for converting lactones to diols
GB8811009D0 (en) * 1988-05-10 1988-06-15 Bp Chem Int Ltd Chemical process
JPH075489B2 (ja) * 1988-05-17 1995-01-25 三菱化学株式会社 ジオール及び／又は環状エーテルの製造法
JP2596604B2 (ja) * 1988-12-14 1997-04-02 東燃株式会社 １，４−ブタンジオールおよびテトラヒドロフランの製造方法
US5030773A (en) * 1990-07-25 1991-07-09 General Electric Company Process for the production of butanediol
WO1992002298A1 (en) * 1990-07-27 1992-02-20 E.I. Du Pont De Nemours Company Hydrogenation catalyst and method for preparing tetrahydrofuran
US5196602A (en) * 1991-12-30 1993-03-23 The Standard Oil Company Two-stage maleic anhydride hydrogenation process for 1,4-butanediol synthesis
DE4228884A1 (de) * 1992-08-29 1994-03-03 Basf Ag Verfahren zur Herstellung von Reduktionsprodukten von Derivaten der 4-Hydroxybuttersäure
DE10061558A1 (de) * 2000-12-11 2002-06-13 Basf Ag Verfahren zur Hydrierung von Maleinsäureanhydrid und verwandten Verbindungen in einem Wirbelschichtreaktor
US20040030199A1 (en) * 2002-01-29 2004-02-12 Maughon Robert R. Process for reducing alpha-haloketones to secondary alpha-haloalcohols
GB0210143D0 (en) * 2002-05-02 2002-06-12 Davy Process Techn Ltd Process
DE10225927A1 (de) * 2002-06-11 2003-12-24 Basf Ag Verfahren zur Herstellung von Butandiol durch kombinierte Gasphasen- und Flüssigphasensynthese
DE10225926A1 (de) * 2002-06-11 2003-12-24 Basf Ag Verfahren zur Herstellung von Butandiol
DE10225929A1 (de) * 2002-06-11 2003-12-24 Basf Ag Zweistufiges Verfahren zur Herstellung von Butandiol mit Zwischenabtrennung von Bernsteinsäureanhydrid
GB0325526D0 (en) * 2003-10-31 2003-12-03 Davy Process Techn Ltd Process
WO2006067171A1 (en) * 2004-12-23 2006-06-29 Shell Internationale Research Maatschappij B.V. A process for the hydrogenation of a lactone or of a carboxylic acid or an ester having a gamma-carbonyl group
WO2008091627A2 (en) * 2007-01-22 2008-07-31 Genomatica, Inc. Methods and organisms for growth-coupled production of 3-hydroxypropionic acid
LT2821494T (lt) 2007-03-16 2017-04-25 Genomatica, Inc. 1,4-butandiolio ir jo pirmtakų biosintezės būdai ir kompozicijos
WO2009045637A2 (en) * 2007-08-10 2009-04-09 Genomatica, Inc. Methods for the synthesis of acrylic acid and derivatives from fumaric acid
US7947483B2 (en) 2007-08-10 2011-05-24 Genomatica, Inc. Methods and organisms for the growth-coupled production of 1,4-butanediol
JP2011509691A (ja) 2008-01-22 2011-03-31 ジェノマティカ， インコーポレイテッド 合成ガスまたは他のガス状炭素源およびメタノールを利用するための方法および生物体
EP2262901B1 (en) 2008-03-05 2018-11-21 Genomatica, Inc. Primary alcohol producing organisms
KR100922998B1 (ko) * 2008-03-06 2009-10-22 한국화학연구원 모노카르복실산 또는 그의 유도체로부터 일가 알콜의 제조방법
CN102066551B (zh) 2008-03-27 2013-10-09 基因组股份公司 用于产生己二酸和其他化合物的微生物
JP2011519561A (ja) * 2008-05-01 2011-07-14 ジェノマティカ， インコーポレイテッド メタクリル酸の産生のための微生物
EP2304039B1 (en) * 2008-06-17 2019-08-21 Genomatica, Inc. Microorganisms and methods for the biosynthesis of fumarate, malate, and acrylate
US20100021978A1 (en) * 2008-07-23 2010-01-28 Genomatica, Inc. Methods and organisms for production of 3-hydroxypropionic acid
WO2010030711A2 (en) 2008-09-10 2010-03-18 Genomatica, Inc. Microorganisms for the production of 1,4-butanediol
AU2009327490A1 (en) 2008-12-16 2011-07-28 Genomatica, Inc. Microorganisms and methods for conversion of syngas and other carbon sources to useful products
JP2012525156A (ja) 2009-04-30 2012-10-22 ゲノマチカ， インク． イソプロパノール、ｎ−ブタノール、及びイソブタノールの産生のための微生物
US9017983B2 (en) 2009-04-30 2015-04-28 Genomatica, Inc. Organisms for the production of 1,3-butanediol
JP5773990B2 (ja) 2009-05-07 2015-09-02 ゲノマチカ， インク． アジペート、ヘキサメチレンジアミン、及び６−アミノカプロン酸の生合成のための微生物及び方法
WO2010132845A1 (en) * 2009-05-15 2010-11-18 Genomatica, Inc. Organisms for the production of cyclohexanone
CN107384846B (zh) 2009-06-04 2021-08-10 基因组股份公司 生产1,4-丁二醇的微生物和相关方法
CA2764368C (en) 2009-06-04 2017-08-01 Genomatica, Inc. Process of separating components of a fermentation broth
EP2440669A4 (en) 2009-06-10 2013-08-28 Genomatica Inc MICROOGANISMS AND PROCEDURES FOR THE CARBON EFFECTIVE BIOSYNTHESIS MEK AND 2-BUTANOL
WO2011017560A1 (en) 2009-08-05 2011-02-10 Genomatica, Inc. Semi-synthetic terephthalic acid via microorganisms that produce muconic acid
US8580978B2 (en) * 2009-08-07 2013-11-12 Shell Oil Company Process for preparing a hydroxyacid or hydroxyester
US20110112326A1 (en) * 2009-08-07 2011-05-12 Jean-Paul Lange Process for hydrogenation
JP2013504326A (ja) 2009-09-09 2013-02-07 ジェノマティカ・インコーポレイテッド イソプロパノールならびに第一級アルコール、ジオールおよび酸の共生成のための微生物ならびに方法
CN105441374A (zh) 2009-10-13 2016-03-30 基因组股份公司 生产1,4-丁二醇、4-羟基丁醛、4-羟基丁酰-coa、腐胺和相关化合物的微生物及其相关方法
KR20180014240A (ko) 2009-10-23 2018-02-07 게노마티카 인코포레이티드 아닐린의 제조를 위한 미생물
WO2011066076A1 (en) 2009-11-25 2011-06-03 Genomatica, Inc. Microorganisms and methods for the coproduction of 1,4-butanediol and gamma-butyrolactone
WO2011071682A1 (en) 2009-12-10 2011-06-16 Genomatica, Inc. Methods and organisms for converting synthesis gas or other gaseous carbon sources and methanol to 1,3-butanediol
MX2012008738A (es) 2010-01-29 2012-08-31 Genomatica Inc Microorganismos y metodos para la biosintesis de p-toluato y tereftalato.
US8637286B2 (en) 2010-02-23 2014-01-28 Genomatica, Inc. Methods for increasing product yields
US8048661B2 (en) 2010-02-23 2011-11-01 Genomatica, Inc. Microbial organisms comprising exogenous nucleic acids encoding reductive TCA pathway enzymes
US9023636B2 (en) 2010-04-30 2015-05-05 Genomatica, Inc. Microorganisms and methods for the biosynthesis of propylene
WO2011140171A2 (en) 2010-05-05 2011-11-10 Genomatica, Inc. Microorganisms and methods for the biosynthesis of butadiene
MX2013001071A (es) 2010-07-26 2013-06-28 Genomatica Inc Microorganismos y metodos para la biosintesis de aromaticos, 2, 4-pentadienoato y 1, 3-butadieno.
WO2013184602A2 (en) 2012-06-04 2013-12-12 Genomatica, Inc. Microorganisms and methods for production of 4-hydroxybutyrate, 1,4-butanediol and related compounds
US9834491B2 (en) * 2013-03-20 2017-12-05 Cj Cheiljedang Corporation Method for producing bio-based homoserine lactone and bio-based organic acid from O-acyl homoserine produced by microorganisms
EP2989113B1 (en) 2013-04-26 2024-04-10 Genomatica, Inc. Microorganisms and methods for production of 4-hydroxybutyrate, 1,4-butanediol and related compounds
US20200071286A1 (en) * 2016-12-20 2020-03-05 Sabic Global Technologies B.V. Utilization of normal carbon 4 (nc4) recycle stream for secondary and tertiary products

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2607807A (en) * 1950-02-24 1952-08-19 Du Pont Preparation of alcohols from carboxylic acids
US2772292A (en) * 1953-07-13 1956-11-27 Du Pont Hydrogenation of maleic anhydride
US3055840A (en) * 1958-01-13 1962-09-25 Engelhard Ind Inc Ruthenium-containing catalysts and methods of making said catalysts and increasing their activity
US3370067A (en) * 1967-04-07 1968-02-20 Shell Oil Co Hydrogenolysis of butyrolactone and gamma-valerolactone to the corresponding cyclic ethers
DE1939882A1 (de) * 1968-08-10 1970-02-19 Mitsubishi Chem Ind Verfahren zur Herstellung von Ta?rahydrofuran
DE2715667A1 (de) * 1977-04-07 1978-10-12 Hoechst Ag Verfahren zur herstellung von butandiol-(1.4)
NL7704658A (nl) * 1977-04-28 1978-10-31 Shell Int Research Werkwijze voor de bereiding van koolwaterstoffen.

Also Published As

Publication number Publication date
JPS57109736A (en) 1982-07-08
CA1157031A (en) 1983-11-15
EP0055512B1 (en) 1984-10-17
KR880000544B1 (ko) 1988-04-13
US4301077A (en) 1981-11-17
JPH0459303B2 (ko) 1992-09-21
DE3166724D1 (en) 1984-11-22
EP0055512A1 (en) 1982-07-07

Similar Documents

Publication Publication Date Title
KR830007611A (ko) 1,4-부탄디올 및 테트라하이드로푸란의 제조방법
KR860004002A (ko) 3-펜테노산의 제조방법
KR830004281A (ko) 피롤리돈을 제조하는 방법 및 촉매
DE2420555A1 (de) Verfahren zur erzeugung eines methanreichen gases
US1979841A (en) Nonknocking motor fuel
ES431970A1 (es) Un procedimiento para la conversion de monoxido de carbono y vapor de agua en hidrogeno y dioxido de carbono.
KR840005422A (ko) 글리옥실산 및 글리옥실산 유도체의 제조방법
GB1318248A (en) Method for reforming paraffinic and naphthenic hydrocarbon feed streams
DE1545438A1 (de) Verfahren zur Wasserdampfreformierung von zwischen 30 und 400 deg.C siedenden Kohlenwasserstoffen
KR840001941A (ko) 에틸렌 글리콜의 제조방법
KR860008144A (ko) 1,3- 디알킬 -2- 이미다졸리디논의 제조방법
DE2449448C2 (de) Verfahren zur Herstellung von Kohlenmonoxid und/oder Wasserstoff enthaltenden Gasen
KR880011054A (ko) 산화티탄 담지 팔라듐 촉매의 제조방법
KR840000457A (ko) 합성가스로부터 알칸올을 제조하는 방법
ES375412A1 (es) Un procedimiento para producir fracciones de queroseno no combustible para motores a reaccion.
KR880013872A (ko) 이성화에 의한 4-펜터노에이트의 제조방법
KR830003933A (ko) 함유황 차아지 스톡(Charge stock)의 재생방법
DE1545434A1 (de) Katalysator zur Umwandlung von Kohlenwasserstoffen
JPS56140948A (en) Fixation of carbon dioxide
DE765790C (de) Verfahren zur Herstellung von Sulfonsaeurechloriden
DE1055533B (de) Verfahren zur Herstellung von Divinylzinnoxyd
FR2545481B1 (fr) Procede de preparation de perfluoroalcanols
ES8202528A1 (es) Un procedimiento para la hidrogenacion de un disolvente
DE339493C (de) Verfahren zur Darstellung von Aethan aus Acetylen und Wasserstoff
KR870009984A (ko) 방향족 디아민의 제조방법