CN101098842A - 2-丁烯-1,4-二醇的制备方法 - Google Patents
2-丁烯-1,4-二醇的制备方法 Download PDFInfo
- Publication number
- CN101098842A CN101098842A CNA200580046190XA CN200580046190A CN101098842A CN 101098842 A CN101098842 A CN 101098842A CN A200580046190X A CNA200580046190X A CN A200580046190XA CN 200580046190 A CN200580046190 A CN 200580046190A CN 101098842 A CN101098842 A CN 101098842A
- Authority
- CN
- China
- Prior art keywords
- glycol
- hydrogenation
- catalyst
- butylene
- fiber
- Prior art date
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 239000000835 fiber Substances 0.000 claims description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 3
- ORTVZLZNOYNASJ-UHFFFAOYSA-N but-2-ene-1,4-diol Chemical compound OCC=CCO ORTVZLZNOYNASJ-UHFFFAOYSA-N 0.000 abstract 1
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 abstract 1
- 239000004744 fabric Substances 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- -1 acryl Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000013462 industrial intermediate Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000011726 vitamin B6 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
- C07C33/035—Alkenediols
-
- 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
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- 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
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- 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
- B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
-
- 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
- B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
- B01J35/58—Fabrics or filaments
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
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)
Abstract
在不存在溶剂的条件下,在结构化催化剂的存在下氢化2-丁炔-1,4-二醇,由此可以制备2-丁烯-1,4-二醇。
Description
本发明涉及2-丁烯-2,4-二醇的制备,而2-丁烯-2,4-二醇是维生素B6、药物和杀虫剂的制备中的重要的工业中间体。
2-丁烯-1,4-二醇通常通过在溶剂(例如水溶液)中将2-丁炔-1,4-二醇催化氢化来制备2-丁烯-1,4-二醇。为了便于回收催化剂,已有建议在2-丁炔-1,4-二醇水溶液的氢化中使用丝状纺织布作为催化剂载体,参见Chem.Engineering Science 57(2002),3453-3460。
根据本发明,现已发现,在不存在溶剂的条件下,通过在结构化催化剂上对2-丁炔-1,4-二醇进行催化氢化,可以以高收率和高选择性制备2-丁烯-1,4-二醇。由于氢微溶于例如水的溶剂中,因此不存在这样的溶剂,则可使单位时间的转化率更高,从而提高氢化方法的经济性。此外,由于本发明的方法避免了溶剂的分离和回收过程,所以出于环保的考虑本发明的方法也是优选的。
因此,本发明涉及制备2-丁烯-1,4-二醇的方法,所述方法包括在存在结构化催化剂且不存在溶剂的条件下氢化2-丁炔-1,4-二醇。
本文所用术语“结构化催化剂”是指空间位置受控制的催化剂。结构化催化剂在本领域中是已知的,例如参见Chimia 56(4),2002,159-163。结构化催化剂的例子是陶瓷载体构造和纤维结构,特别是丝状纺织布。所有类型的丝状纺织布均可用于本发明。纤维可由有机或无机物质制成。其例子是由活性炭纤维制成的织物,例如丙烯腈纤维、玻璃纤维、陶瓷纤维、金属纤维或羊毛复合氧化物的活性炭纤维。优选的是聚丙烯腈织物。丝状纺织布的单根纤维的直径优选为约2-100μm,特别地,所述直径不大于约20μm。适宜地,织物由纤维束构成的丝线所织成,织布的孔径小于约1mm。可以例如用硝酸对织物进行化学处理以调整比表面积,并且织物可以具有例如金属(如Al、Ti或Pb)涂层以改善选择性。
作为催化剂,可以使用可催化2-丁炔-2,4-二醇至2-丁烯-2,4-二醇的选择性氢化的任何氢化催化剂。这样的催化剂的例子是贵金属,例如钯、铂、铱、铑、钌或其组合。载体织物上存在的催化剂的量可达约10质量%,适宜地为1-10质量%。通过用催化剂前驱体(催化剂金属的盐)的溶液进行处理,随后在氢气氛中干燥和加热,实现载体织物的加载,并且可以通过加载溶液(loading solution)中催化剂前驱体的浓度来控制载体织物的加载。
本发明的氢化可以在用于氢化2-丁炔-2,4-二醇以制备至2-丁烯-2,4-二醇的常规条件下进行。适宜地,氢化在约0.1-6MPa的压力和约350-500K的温度下进行。氢化可以以间歇或连续方式进行。
以下实施例进一步阐明了本发明,但这些实施例并不限制本发明。
实施例
催化剂制备
将平纹织物形式的源自聚丙烯腈的活性炭纤维(Taiwan CarbonTechnology Co)用作制备催化剂的载体。织物由直径约为0.5mm的长丝线织成。这些丝线由3-5μm的单丝组成的束构成。如Chem.EngineeringScience 57(2002),3453-3460中所述,通过与Na2PdCl4水溶液的离子交换将钯沉积在织物上。用原子吸收光谱测定钯的加载量为4质量%,并通过BET法来分析催化剂的比表面积和孔径分布。采用一氧化碳的脉冲化学吸附来确定Pd的分散,参见上面提到的Chem.Eng.Sci.。
实验装置
上面提到的Chem.Eng.Sci.中详细描述了实验装置。
反应在由加热夹套保持的等温条件下在间歇反应器(150ml高压釜,Buechiglas,Uster,CH)中进行。该高压釜具有定量气体供给系统。
纤维催化剂被置于两个固定在搅拌器上的金属丝网(20×40mm)之间。
置于反应器中的催化剂的量在150与35mg之间变化。搅拌速度被保持在1500rpm以避免质量传递限制。为了达到有效的气-液接触,使用自出气中空轴搅拌器。在等压反应条件下向高压釜中充入氢气(>99.99%)。
装入纯的2-丁炔-1,4-二醇固体(熔点331K),并在氩气氛下熔化以防止反应物降解。在达到所需温度之后,用氢气冲洗反应器,并将其加压至期望水平。在反应过程中,通过以氢气消耗的速率从储罐中供给氢气,将反应器中H2的压力维持恒定。连续监测H2储罐中的压力,从而对瞬时的氢消耗进行在线测量。
用以He作为载气的配备FID检测器的气相色谱仪(Auto SystemXL,PERKIN ELMER)对从环路中取出的液体样品进行分析。在20K/min的温升速度(373-493K)下,在30m的Perkin Elmer Elite系列的0.25mm的具有0.25μm涂层的毛细柱上,对产物进行分离。使用1,3-丁二醇作为GC定量分析的内标。
不同反应条件下的实验结果示于图1-3。
图1示出了反应温度为325K时的典型的浓度-时间曲线。如图2所示,在丁炔二醇(B3)的转化率达到90%时,测量和预测的丁烯二醇(B2)的选择性约为98%;而当丁炔二醇(B3)的转化率为99%时,测量和预测的丁烯二醇(B2)的选择性降至95%。从图3可以看出温度对反应速率的影响,图中示出了作为时间函数的反应物浓度。基于初始反应速率,可以计算转化频率对温度的依赖性。
Claims (11)
1.制备2-丁烯-1,4-二醇的方法,所述方法包括在存在结构化催化剂且不存在溶剂的条件下氢化2-丁炔-1,4-二醇。
2.如权利要求1的方法,其中所述结构化催化剂的载体是丝状纺织布。
3.如权利要求2的方法,其中所述丝状纺织布由活性炭纤维制成。
4.如权利要求2的方法,其中所述活性炭纤维由聚丙烯腈纤维制成。
5.如权利要求2-4中任何一项的方法,其中所述纤维的直径为约2-100μm。
6.如权利要求2-5中任何一项的方法,其中所述纤维的直径不大于20μm 。
7.如权利要求2-6中任何一项的方法,其中所述纺织布的孔径小于1mm 。
8.如权利要求2-7中任何一项的方法,其中所述催化剂为钯催化剂。
9.如权利要求1-8中任何一项的方法,其中所述载体上的催化剂加载量为约1-10质量%。
10.如权利要求1-9中任何一项的方法,其中所述氢化在约0.1-6MPa的压力下进行。
11.如权利要求1-10中任何一项的方法,其中所述氢化在约350-500K的温度下进行。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05000227.8 | 2005-01-07 | ||
EP05000227 | 2005-01-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN101098842A true CN101098842A (zh) | 2008-01-02 |
Family
ID=36589014
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNA200580046190XA Pending CN101098842A (zh) | 2005-01-07 | 2005-12-29 | 2-丁烯-1,4-二醇的制备方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US7541501B2 (zh) |
EP (1) | EP1833779B1 (zh) |
JP (1) | JP4960886B2 (zh) |
KR (1) | KR101226317B1 (zh) |
CN (1) | CN101098842A (zh) |
WO (1) | WO2006072441A2 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102295530A (zh) * | 2011-08-11 | 2011-12-28 | 浙江启明药业有限公司 | 一种3-丁烯-1-醇的合成方法 |
CN109622049A (zh) * | 2018-12-21 | 2019-04-16 | 万华化学集团股份有限公司 | 用于炔丙基醇部分加氢制备烯丙基醇的催化剂及其制法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9975827B2 (en) * | 2014-07-23 | 2018-05-22 | Fundacion Tecnalia Research & Innovation | Method for manufacturing 2,3-butanediol |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4333293A1 (de) * | 1993-09-30 | 1995-04-06 | Basf Ag | Verfahren zur selektiven Hydrierung von Butindiol-1,4 zu Buten-2-diol-1,4 und dafür geeigneter Katalysator |
DE19962907A1 (de) * | 1999-12-23 | 2001-07-05 | Basf Ag | Verfahren zur Herstellung von C¶10¶-C¶30¶-Alkenen durch partielle Hydrierung von Alkinen an Festbett-Palladium-Trägerkatalysatoren |
-
2005
- 2005-12-29 US US11/794,240 patent/US7541501B2/en active Active
- 2005-12-29 WO PCT/EP2005/014103 patent/WO2006072441A2/en active Application Filing
- 2005-12-29 EP EP05824627.3A patent/EP1833779B1/en active Active
- 2005-12-29 JP JP2007549826A patent/JP4960886B2/ja active Active
- 2005-12-29 KR KR1020077015411A patent/KR101226317B1/ko active IP Right Grant
- 2005-12-29 CN CNA200580046190XA patent/CN101098842A/zh active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102295530A (zh) * | 2011-08-11 | 2011-12-28 | 浙江启明药业有限公司 | 一种3-丁烯-1-醇的合成方法 |
CN102295530B (zh) * | 2011-08-11 | 2013-11-06 | 浙江启明药业有限公司 | 一种3-丁烯-1-醇的合成方法 |
CN109622049A (zh) * | 2018-12-21 | 2019-04-16 | 万华化学集团股份有限公司 | 用于炔丙基醇部分加氢制备烯丙基醇的催化剂及其制法 |
Also Published As
Publication number | Publication date |
---|---|
WO2006072441A2 (en) | 2006-07-13 |
WO2006072441A3 (en) | 2006-10-19 |
KR20070091640A (ko) | 2007-09-11 |
JP2008526797A (ja) | 2008-07-24 |
EP1833779A2 (en) | 2007-09-19 |
US20080312475A1 (en) | 2008-12-18 |
US7541501B2 (en) | 2009-06-02 |
EP1833779B1 (en) | 2014-05-07 |
KR101226317B1 (ko) | 2013-01-24 |
JP4960886B2 (ja) | 2012-06-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Besson et al. | Catalytic oxidation of glucose on bismuth-promoted palladium catalysts | |
Kiwi-Minsker et al. | Supported glass fibers catalysts for novel multi-phase reactor design | |
Höller et al. | Three‐phase nitrobenzene hydrogenation over supported glass fiber catalysts: Reaction kinetics study | |
TWI439316B (zh) | 用於從合成氣體中移除氫化氰和甲酸的方法 | |
US5853693A (en) | Hydrogenation catalyst for production of hydrogen peroxide, and method for preparation of same | |
Joannet et al. | Palladium supported on filamentous active carbon as effective catalyst for liquid-phase hydrogenation of 2-butyne-1, 4-diol to 2-butene-1, 4-diol | |
WO2008101603A2 (en) | Catalysts based on sintered metal fibers coated by zinc oxide layer impregnated with palladium nanoparticles for the hydrogenation of alkynols | |
JP2014532555A (ja) | 酸化ジルコニウムを含む過酸化水素の直接合成のための触媒 | |
Nikov et al. | Palladium on alumina catalyst for glucose oxidation: reaction kinetics and catalyst deactivation | |
CN102099323A (zh) | 乙醇酸的生产方法 | |
Yuranova et al. | Nanostructured catalysts for the continuous reduction of nitrates and bromates in water | |
KR100584771B1 (ko) | 테레프탈산 정제용 촉매, 그의 제조방법 및 테레프탈산의정제방법 | |
EP2588233B1 (en) | Novel structured catalyst | |
CN102078810A (zh) | 氧化物负载钯加氢催化剂及其制备方法 | |
BR112014030857B1 (pt) | Processo de produção de ácido adípico a partir de 1,6-hexanodiol | |
Duff et al. | Catalysts derived from polymer-stabilised colloidal platinum: Effects of support and calcination on the catalytic behaviour in hydrogenation | |
Bhanushali et al. | Simultaneous dehydrogenation of 1, 4-butanediol to γ-butyrolactone and hydrogenation of benzaldehyde to benzyl alcohol mediated over competent CeO2–Al2O3 supported Cu as catalyst | |
WO2001051203A1 (fr) | Support a forte teneur en silicium, catalyseur utilise pour des reactions heterogenes et procede de production associe | |
CN101098842A (zh) | 2-丁烯-1,4-二醇的制备方法 | |
Bai et al. | Synthesis of tailored egg-shell Pd@ Al2O3 catalyst for catalytic hydrogenation of 2-alkylanthraquinone | |
Xu et al. | Catalytic hydrogenation of aqueous nitrate over Pd− Cu/ZrO2 catalysts | |
Zhu et al. | Characterization of bimetallic Ru-Sn supported catalysts and hydrogenation of 1, 4-cyclohexanedicarboxylic acid | |
Chen et al. | Characterizations of Ir/TiO 2 catalysts with different Ir contents for selective hydrogenation of crotonaldehyde | |
Rosso et al. | Preferential CO oxidation over Pt/3A zeolite catalysts in H 2-rich gas for fuel cell application | |
Mikkola et al. | Structured but not over-structured: Woven active carbon fibre matt catalyst |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
WD01 | Invention patent application deemed withdrawn after publication |
Open date: 20080102 |