CN1090532C - 催化剂、其制备方法和在合成甲硫醇中的应用 - Google Patents

催化剂、其制备方法和在合成甲硫醇中的应用 Download PDF

Info

Publication number: CN1090532C
Authority: CN; China
Prior art keywords: wolframic acid; catalyst; aluminum oxide; catalyzer; weight
Prior art date: 1996-09-26
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

CN97119568A

Other languages

English (en)

Chinese (zh)

Other versions

CN1178137A (zh

Inventor

J·萨尤尔

W·保克

L·冯黑派尔

W·布克哈特

S·拉坦伯格

D·阿恩兹

W·霍芬

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Evonik Operations GmbH

Original Assignee

Degussa GmbH

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.)

1996-09-26

Filing date

1997-09-25

Publication date

2002-09-11

1997-09-25 Application filed by Degussa GmbH filed Critical Degussa GmbH

1998-04-08 Publication of CN1178137A publication Critical patent/CN1178137A/zh

2002-09-11 Application granted granted Critical

2002-09-11 Publication of CN1090532C publication Critical patent/CN1090532C/zh

2017-09-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 title claims abstract description 32
239000003054 catalyst Substances 0.000 title claims abstract description 25
230000015572 biosynthetic process Effects 0.000 title claims abstract description 9
238000003786 synthesis reaction Methods 0.000 title claims abstract description 9
238000002360 preparation method Methods 0.000 title claims description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 51
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims abstract description 31
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims abstract description 18
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 14
229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 14
229910052792 caesium Inorganic materials 0.000 claims abstract 3
239000002253 acid Substances 0.000 claims description 42
238000000034 method Methods 0.000 claims description 14
238000007598 dipping method Methods 0.000 claims description 11
238000000465 moulding Methods 0.000 claims description 9
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
-1 alkali metal salt Chemical class 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 11
AAQNGTNRWPXMPB-UHFFFAOYSA-N dipotassium;dioxido(dioxo)tungsten Chemical compound [K+].[K+].[O-][W]([O-])(=O)=O AAQNGTNRWPXMPB-UHFFFAOYSA-N 0.000 abstract description 4
PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 abstract description 3
239000012190 activator Substances 0.000 abstract 2
238000004519 manufacturing process Methods 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 15
239000001103 potassium chloride Substances 0.000 description 15
235000011164 potassium chloride Nutrition 0.000 description 15
230000000052 comparative effect Effects 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000002245 particle Substances 0.000 description 10
239000011148 porous material Substances 0.000 description 8
239000011248 coating agent Substances 0.000 description 7
238000000576 coating method Methods 0.000 description 7
239000012530 fluid Substances 0.000 description 7
239000003513 alkali Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000008187 granular material Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007789 gas Substances 0.000 description 3
238000005554 pickling Methods 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
238000006424 Flood reaction Methods 0.000 description 2
238000013019 agitation Methods 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000002585 base Substances 0.000 description 2
HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
235000011194 food seasoning agent Nutrition 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
239000012495 reaction gas Substances 0.000 description 2
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000007704 transition Effects 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
206010013786 Dry skin Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
239000012018 catalyst precursor Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000000975 co-precipitation Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000007599 discharging Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000007667 floating Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
238000007669 thermal treatment Methods 0.000 description 1

Classifications

- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/30—Tungsten
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/08—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by replacement of hydroxy groups or etherified or esterified hydroxy groups

Landscapes

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

CN97119568A 1996-09-26 1997-09-25 催化剂、其制备方法和在合成甲硫醇中的应用 Expired - Lifetime CN1090532C (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19639584.4		1996-09-26
DE19639584A DE19639584A1 (de)	1996-09-26	1996-09-26	Katalysator, Verfahren zu seiner Herstellung und Verwendung zur Synthese von Methylmercaptan

Publications (2)

Publication Number	Publication Date
CN1178137A CN1178137A (zh)	1998-04-08
CN1090532C true CN1090532C (zh)	2002-09-11

Family

ID=7806976

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN97119568A Expired - Lifetime CN1090532C (zh)	1996-09-26	1997-09-25	催化剂、其制备方法和在合成甲硫醇中的应用

Country Status (8)

Country	Link
US (1)	US5852219A (2)
EP (1)	EP0832687B1 (2)
JP (1)	JP3976852B2 (2)
CN (1)	CN1090532C (2)
BR (1)	BR9704898A (2)
DE (2)	DE19639584A1 (2)
ES (1)	ES2166029T3 (2)
RU (1)	RU2191069C2 (2)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1072523C (zh) *	1998-09-10	2001-10-10	厦门大学	一种含高硫化氢浓度的合成气制甲硫醇的催化剂
CN1072522C (zh) *	1998-09-10	2001-10-10	厦门大学	一种由含硫化氢的合成气合成甲硫醇的催化剂
GB2368672A (en) *	2000-04-19	2002-05-08	Ford Global Tech Inc	Online invention disclosure system
DE60117198T2 (de) *	2000-06-27	2006-07-27	Saudi Basic Industries Corp. (Sabic)	Verfahren für die Herstellung von Olefinen durch oxidative Dehydrierung
JP3757267B2 (ja) *	2001-07-23	2006-03-22	独立行政法人産業技術総合研究所	多元系固体触媒の迅速探索方法
JP3572548B2 (ja)	2002-05-24	2004-10-06	日本酸素株式会社	ガス精製方法及び装置
DE10319739A1 (de) *	2003-04-30	2004-11-18	Basf Ag	Katalysator zur Herstellung von Methylmercaptan aus Methanol und Schwefelwasserstoff
DE10338887A1 (de) *	2003-08-23	2005-03-17	Degussa Ag	Katalysator zur Synthese von Alkylmercaptan und Verfahren zu seiner Herstellung
CN100345629C (zh) *	2003-10-10	2007-10-31	德古萨股份公司	一种由含高浓度硫化氢的合成气合成甲硫醇的催化剂
DE102004037739A1 (de)	2004-08-04	2006-03-16	Degussa Ag	Wolframat enthaltende Katalysatoren zur Synthese von Alkylmercaptan und Verfahren zu ihrer Herstellung
DE102004061016A1 (de) *	2004-12-18	2006-06-22	Degussa Ag	Halogenidhaltige Alkaliwolframate enthaltende Katalysatoren zur Synthese von Alkylmercaptan und Verfahren zu ihrer Herstellung
DE102005016369A1 (de) *	2005-04-09	2006-10-12	Degussa Ag	Verfahren zur kontinuierlichen Herstellung von Methylmercaptan
DE102006032635A1 (de)	2006-07-13	2008-01-17	Evonik Degussa Gmbh	Verfahren zur Herstellung von Alkylmercaptanen in einem Mehrzonenfestbettreaktor
AR066468A1 (es)	2007-05-09	2009-08-19	Shell Int Research	Un catalizador de epoxidacion, un proceso para preparar el mismo, y un proceso para producir un oxido de olefina , un 1,2- diol, un 1,2 - diol eter, un 1,2- carbonato, o una alcanolamina
DE102007024576A1 (de)	2007-05-25	2009-05-20	Evonik Degussa Gmbh	Verfahren zur kontinuierlichen Herstellung von Methylmercaptan aus kohlenstoff- und wasserstoffhaltigen Verbindungen
SG171866A1 (en)	2008-12-23	2011-07-28	Basf Se	Method for compressing gases containing hydrogen sulfide
DE102009027837A1 (de)	2009-07-20	2011-01-27	Evonik Degussa Gmbh	Verfahren zur kontinuierlichen Herstellung von Methylmercaptan aus kohlenstoffhaltigen Verbindungen, Schwefel und Wasserstoff
KR101068112B1 (ko) *	2010-02-22	2011-09-27	한국에너지기술연구원	텅스텐 옥사이드 알루미나 촉매의 제조 방법, 텅스텐 옥사이드 알루미나 촉매 및 이 촉매를 이용한 유리지방산이 포함되어 있는 폐식용유로부터 유리지방산을 제거하는 방법
EP3187261A1 (de) *	2015-12-30	2017-07-05	Evonik Degussa GmbH	Verfahren zur herstellung eines ein alkalimetall und eines übergangsmetall in oxidierter form enthaltenden katalysators
CA3020740A1 (en)	2016-05-31	2017-12-07	Novus International Inc.	Process for producing methyl mercaptan from dimethyl sulfide
EP3689451A1 (en)	2019-01-29	2020-08-05	Evonik Operations GmbH	Catalyst for the synthesis of alkyl mercaptan and process for its preparation
CN114478334B (zh) *	2022-02-25	2023-11-10	新疆广汇陆友硫化工有限公司	一种甲硫醇硫化法生产二甲基二硫的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3935276A (en) *	1973-11-30	1976-01-27	Rhone-Poulenc Industries	Process for the manufacture of methyl mercaptan
JPS58159456A (ja) *	1982-03-17	1983-09-21	Seitetsu Kagaku Co Ltd	メチルメルカプタンの製造方法
JPS6084239A (ja) *	1983-10-14	1985-05-13	Agency Of Ind Science & Technol	アセトアルデヒドの製造法

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US2820062A (en) *	1954-08-11	1958-01-14	Pure Oil Co	Preparation of organic thiols
US5057481A (en) *	1987-02-20	1991-10-15	Union Carbide Chemicals And Plastics Technology Corporation	Catalyst composition for oxidation of ethylene to ethylene oxide
US4908343A (en) *	1987-02-20	1990-03-13	Union Carbide Chemicals And Plastics Company Inc.	Catalyst composition for oxidation of ethylene to ethylene oxide
US5283369A (en) *	1992-03-24	1994-02-01	Elf Atochem North America, Inc.	Selective synthesis of mercaptans and catalyst therefor
RU2056940C1 (ru) *	1992-03-26	1996-03-27	Специальное конструкторско-технологическое бюро катализаторов с опытным заводом	Способ получения катализатора для синтеза метилмеркаптана и диметилсульфида

1996
- 1996-09-26 DE DE19639584A patent/DE19639584A1/de not_active Withdrawn
1997
- 1997-06-30 US US08/885,045 patent/US5852219A/en not_active Expired - Lifetime
- 1997-07-10 EP EP97111737A patent/EP0832687B1/de not_active Expired - Lifetime
- 1997-07-10 ES ES97111737T patent/ES2166029T3/es not_active Expired - Lifetime
- 1997-07-10 DE DE59705162T patent/DE59705162D1/de not_active Expired - Lifetime
- 1997-09-24 JP JP25840497A patent/JP3976852B2/ja not_active Expired - Lifetime
- 1997-09-25 CN CN97119568A patent/CN1090532C/zh not_active Expired - Lifetime
- 1997-09-26 BR BR9704898A patent/BR9704898A/pt not_active IP Right Cessation
- 1997-09-26 RU RU97116038/04A patent/RU2191069C2/ru not_active IP Right Cessation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3935276A (en) *	1973-11-30	1976-01-27	Rhone-Poulenc Industries	Process for the manufacture of methyl mercaptan
JPS58159456A (ja) *	1982-03-17	1983-09-21	Seitetsu Kagaku Co Ltd	メチルメルカプタンの製造方法
JPS6084239A (ja) *	1983-10-14	1985-05-13	Agency Of Ind Science & Technol	アセトアルデヒドの製造法

Also Published As

Publication number	Publication date
EP0832687A3 (de)	1998-07-01
US5852219A (en)	1998-12-22
DE59705162D1 (de)	2001-12-06
RU2191069C2 (ru)	2002-10-20
CN1178137A (zh)	1998-04-08
JP3976852B2 (ja)	2007-09-19
BR9704898A (pt)	1998-10-27
EP0832687A2 (de)	1998-04-01
ES2166029T3 (es)	2002-04-01
JPH10109031A (ja)	1998-04-28
EP0832687B1 (de)	2001-10-31
DE19639584A1 (de)	1998-04-23
MX9707253A (es)	1998-03-31

Legal Events

Date	Code	Title	Description
1998-04-08	C06	Publication
1998-04-08	PB01	Publication
1999-09-29	C10	Entry into substantive examination
1999-09-29	SE01	Entry into force of request for substantive examination
2002-09-11	C14	Grant of patent or utility model
2002-09-11	GR01	Patent grant
2010-07-07	C56	Change in the name or address of the patentee	Owner name: EVONIK DEGUSSA CO., LTD. Free format text: FORMER NAME: DEGUSSA CO., LTD. Owner name: DEGUSSA CO., LTD. Free format text: FORMER NAME: DIGUSSA CO., LTD.
2010-07-07	CP03	Change of name, title or address	Address after: essen Patentee after: EVONIK DEGUSSA GmbH Address before: Dusseldorf, Federal Republic of Germany Patentee before: DEGUSSA GmbH Address after: Dusseldorf, Federal Republic of Germany Patentee after: DEGUSSA GmbH Address before: Frankfurt, Federal Republic of Germany Patentee before: Degussa AG
2017-10-31	CX01	Expiry of patent term
2017-10-31	CX01	Expiry of patent term	Granted publication date: 20020911

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