JP4558276B2 - 水素化法 - Google Patents

水素化法 Download PDF

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Publication number
JP4558276B2
JP4558276B2 JP2002591415A JP2002591415A JP4558276B2 JP 4558276 B2 JP4558276 B2 JP 4558276B2 JP 2002591415 A JP2002591415 A JP 2002591415A JP 2002591415 A JP2002591415 A JP 2002591415A JP 4558276 B2 JP4558276 B2 JP 4558276B2
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alkyl
catalyst
selectivity
branched
hydrogen
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Japanese (ja)
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JP2004533455A5 (https=
JP2004533455A (ja
Inventor
アンダーソン，クリス
グッドリッチ，ピーター
ハーダクレ，クリストファー
エリザベス ジェーン マクマス，サラ
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Queens University of Belfast
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Queens University of Belfast
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B35/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving a change in the type of bonding between two carbon atoms already directly linked
    • C07B35/02—Reduction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B41/00—Formation or introduction of functional groups containing oxygen
    • C07B41/02—Formation or introduction of functional groups containing oxygen of hydroxy or O-metal groups
    • 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
    • C07C29/14—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 a —CHO group
    • C07C29/141—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 a —CHO group 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
    • 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
    • C07C29/175—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 an oxo group
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • C07C2521/04—Alumina
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • C07C2521/08—Silica
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/12—Silica and alumina
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/18—Carbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/42—Platinum
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/44—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/46—Ruthenium, rhodium, osmium or iridium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/74—Iron group metals
    • C07C2523/755—Nickel
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/20—Carbon compounds
    • C07C2527/232—Carbonates
    • 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
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Physical Or Chemical Processes And Apparatus (AREA)
  • Saccharide Compounds (AREA)
JP2002591415A 2001-05-18 2002-05-17 水素化法 Expired - Fee Related JP4558276B2 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0112093.0A GB0112093D0 (en) 2001-05-18 2001-05-18 Hydrogenation processes
PCT/GB2002/002333 WO2002094740A2 (en) 2001-05-18 2002-05-17 Hydrogenation processes performed in ionic liquids

Related Child Applications (2)

Application Number Title Priority Date Filing Date
JP2009006295A Division JP2009102385A (ja) 2001-05-18 2009-01-15 水素化法
JP2009236832A Division JP2010006842A (ja) 2001-05-18 2009-10-14 水素化法

Publications (3)

Publication Number Publication Date
JP2004533455A JP2004533455A (ja) 2004-11-04
JP2004533455A5 JP2004533455A5 (https=) 2006-01-05
JP4558276B2 true JP4558276B2 (ja) 2010-10-06

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JP2002591415A Expired - Fee Related JP4558276B2 (ja) 2001-05-18 2002-05-17 水素化法
JP2009006295A Pending JP2009102385A (ja) 2001-05-18 2009-01-15 水素化法
JP2009236832A Pending JP2010006842A (ja) 2001-05-18 2009-10-14 水素化法

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JP2009006295A Pending JP2009102385A (ja) 2001-05-18 2009-01-15 水素化法
JP2009236832A Pending JP2010006842A (ja) 2001-05-18 2009-10-14 水素化法

Country Status (12)

Country Link
US (2) US7667058B2 (https=)
EP (2) EP1921056B1 (https=)
JP (3) JP4558276B2 (https=)
AT (1) ATE417030T1 (https=)
AU (1) AU2002310587A1 (https=)
CA (1) CA2446835A1 (https=)
DE (1) DE60230259D1 (https=)
DK (1) DK1387819T3 (https=)
ES (1) ES2318011T3 (https=)
GB (1) GB0112093D0 (https=)
PT (1) PT1387819E (https=)
WO (1) WO2002094740A2 (https=)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0112093D0 (en) * 2001-05-18 2001-07-11 Univ Belfast Hydrogenation processes
EP1697289B1 (en) 2003-12-18 2014-06-11 ExxonMobil Chemical Patents Inc. Improvements in or relating to hydroformylation
WO2005058782A1 (en) * 2003-12-18 2005-06-30 Exxonmobil Chemical Patents Inc. Improvements in or relating to hydrogenation
GB0500029D0 (en) * 2005-01-04 2005-02-09 Univ Belfast Basic ionic liquids
DE102005049568A1 (de) 2005-10-17 2007-04-19 Basf Ag Verfahren zur kontinuierlichen Hydrierung oder hydrierenden Aminierung
DE102006019460A1 (de) * 2006-04-26 2007-10-31 Süd-Chemie AG Mit einer ionischen Flüssigkeit beschichteter poröser heterogener Katalysator
FR2910471A1 (fr) * 2006-12-26 2008-06-27 Holis Technologies Procede d'hydrogenation asymetrique d'une enamine,dispositif pour la mise en oeuvre du procede et amine chirale obtenue
US7622532B2 (en) * 2007-02-16 2009-11-24 William Marsh Rice University Synthesis of radioactive materials and compositions of same
TWI333946B (en) * 2007-04-26 2010-12-01 Cpc Corp Taiwan Method of selectively hydrogenating 2-methyl-buta-1,3-diene by using supported ionic liquid nano-pd catalyst
KR100963402B1 (ko) * 2007-12-04 2010-06-14 성균관대학교산학협력단 방향족 화합물의 수소화 방법
CN102056877B (zh) * 2008-06-09 2014-11-05 索维索莱克西斯公开有限公司 生产全氟乙烯基醚的方法
WO2010061909A1 (ja) * 2008-11-27 2010-06-03 高砂香料工業株式会社 不斉水素化触媒
DE102009051462B4 (de) 2009-10-30 2015-02-05 Clariant International Ag Verfahren zur Herstellung eines Kompositmaterials, Kompositmaterial und dessen Verwendung
JP5913352B2 (ja) * 2010-11-29 2016-04-27 高砂香料工業株式会社 不斉水素化触媒、およびそれを用いた光学活性カルボニル化合物の製造方法
US20130102819A1 (en) 2011-10-19 2013-04-25 Normen Szesni Catalyst composition for selective hydrogenation with improved characteristics
RU2529033C1 (ru) * 2013-06-13 2014-09-27 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный технический университет" (ВолгГТУ) СПОСОБ ГИДРИРОВАНИЯ α, β-НЕНАСЫЩЕННЫХ КЕТОНОВ
KR101492871B1 (ko) 2013-08-07 2015-02-13 한국과학기술연구원 이온성 액체를 이용하여 제조된 탄소에 담지된 팔라듐 촉매 및 이것의 제조방법과, 이를 이용한 수소불화탄소의 수소화 반응
CN104549494B (zh) * 2013-10-28 2017-06-20 中国石油化工股份有限公司 合成1,4‑环己烷二甲醇的催化剂
CN111504933B (zh) * 2020-05-12 2022-12-06 扬州工业职业技术学院 一种分析检测抗艾滋病新药的方法
CN114100689B (zh) * 2021-11-29 2023-04-07 万华化学集团股份有限公司 一种加氢催化剂及其制备方法与应用
CN114653403B (zh) * 2022-03-18 2023-02-03 大连理工大学 一种用于苯酚加氢制环己酮的双功能催化剂的制备方法及应用
EP4696672A1 (en) 2024-08-16 2026-02-18 ARLANXEO Deutschland GmbH Process for the synthesis of 2-chloro-1,3-butadiene and 2,3-dichloro-1,3-butadiene
WO2026037737A1 (en) 2024-08-16 2026-02-19 Arlanxeo Deutschland Gmbh Process for the synthesis of 2-chloro-1,3-butadiene and 2,3-dichloro-1,3-butadiene

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5459233A (en) * 1977-10-17 1979-05-12 Teijin Ltd Preparation of aromatic hydrocarbons
JPS56133221A (en) * 1980-03-24 1981-10-19 Hodogaya Chem Co Ltd Dechlorinating method of chlorinated toluene
JPS60218330A (ja) * 1984-04-16 1985-11-01 Mitsui Toatsu Chem Inc 脱ハロゲン化方法
JPS63132848A (ja) * 1986-11-22 1988-06-04 Idemitsu Kosan Co Ltd 三重結合を有する炭化水素化合物の選択的水素添加方法
JPS63291643A (ja) * 1987-05-25 1988-11-29 Nippon Kayaku Co Ltd フエニルアセチレン類の選択水素添加反応用触媒
JPH0377836A (ja) * 1989-08-17 1991-04-03 Ishihara Sangyo Kaisha Ltd ｍ―ジフルオロベンゼンの製造方法
JPH03279338A (ja) * 1990-03-28 1991-12-10 Tokuyama Sekiyu Kagaku Kk 不飽和アルコールの製造方法
US5490919A (en) * 1990-08-14 1996-02-13 State Of Isreal, Atomic Energy Commission Process for the dehalogenation of organic compounds
EP0598338B1 (de) * 1992-11-18 1997-03-12 Hoechst Aktiengesellschaft Verfahren zur Herstellung von 1,3-Difluorbenzol
NL9401708A (nl) * 1994-10-17 1996-06-03 Dsm Nv Werkwijze voor de bereiding van 3-fenylpropanal.
DE4438547A1 (de) * 1994-10-28 1996-05-02 Bayer Ag Verfahren zur Hydrierung ungesättigter Fettsäureester
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
JPH09249613A (ja) * 1996-03-15 1997-09-22 Nissan Chem Ind Ltd 新規脂環式化合物及びその製造方法
JP4216931B2 (ja) * 1998-10-22 2009-01-28 株式会社日本触媒 光学活性３−ヒドロキシイソブタン酸エステル類の製造方法
WO2000032572A2 (en) * 1998-12-04 2000-06-08 Symyx Technologies Combinatorial discovery and testing of ionic liquids
GB9928290D0 (en) 1999-12-01 2000-01-26 Univ Belfast Process for preparing ambient temperature ionic liquids
GB0024745D0 (en) * 2000-10-10 2000-11-22 Univ Belfast Oxidation of alkyl-aromatic compounds
GB0112093D0 (en) * 2001-05-18 2001-07-11 Univ Belfast Hydrogenation processes
JP2008271990A (ja) * 2006-06-20 2008-11-13 Kyushu Univ イオン液体中における電解還元による有機ハロゲン化物の脱ハロゲン化方法

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Publication number Publication date
GB0112093D0 (en) 2001-07-11
EP1921056B1 (en) 2015-04-22
EP1921056A1 (en) 2008-05-14
EP1387819A2 (en) 2004-02-11
ES2318011T3 (es) 2009-05-01
JP2010006842A (ja) 2010-01-14
JP2009102385A (ja) 2009-05-14
WO2002094740A8 (en) 2003-05-08
PT1387819E (pt) 2009-03-23
US7667058B2 (en) 2010-02-23
US20040267034A1 (en) 2004-12-30
DE60230259D1 (de) 2009-01-22
CA2446835A1 (en) 2002-11-28
WO2002094740A3 (en) 2003-03-13
DK1387819T3 (da) 2009-04-06
ATE417030T1 (de) 2008-12-15
US7803974B2 (en) 2010-09-28
EP1387819B1 (en) 2008-12-10
AU2002310587A1 (en) 2002-12-03
WO2002094740A2 (en) 2002-11-28
JP2004533455A (ja) 2004-11-04
US20100056782A1 (en) 2010-03-04

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