JP4960886B2 - 2−ブテン−1,4−ジオールの調製方法 - Google Patents
2−ブテン−1,4−ジオールの調製方法 Download PDFInfo
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- JP4960886B2 JP4960886B2 JP2007549826A JP2007549826A JP4960886B2 JP 4960886 B2 JP4960886 B2 JP 4960886B2 JP 2007549826 A JP2007549826 A JP 2007549826A JP 2007549826 A JP2007549826 A JP 2007549826A JP 4960886 B2 JP4960886 B2 JP 4960886B2
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- catalyst
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- 238000000034 method Methods 0.000 title claims description 15
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 title claims description 7
- 239000003054 catalyst Substances 0.000 claims description 25
- 239000000835 fiber Substances 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
- 239000002759 woven fabric Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000919 ceramic Substances 0.000 claims description 3
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000010970 precious metal Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000004744 fabric Substances 0.000 description 7
- 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
- 238000002360 preparation method Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 4
- DXXXHNQOKVRSES-UHFFFAOYSA-N but-2-ene-1,3-diol Chemical compound CC(O)=CCO DXXXHNQOKVRSES-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000002131 composite material Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- RBCOYOYDYNXAFA-UHFFFAOYSA-L (5-hydroxy-4,6-dimethylpyridin-3-yl)methyl phosphate Chemical compound CC1=NC=C(COP([O-])([O-])=O)C(C)=C1O RBCOYOYDYNXAFA-UHFFFAOYSA-L 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- 239000004358 Butane-1, 3-diol Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011065 in-situ storage Methods 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
- 239000002917 insecticide Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- 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)
Description
触媒の調製
平織布の形態のポリアクリロニトリル由来の活性炭素繊維(タイワン・カーボン・テクノロジー・コーポレーション(Taiwan Carbon Technology Co))を触媒調製用の担体として使用した。この織物は直径約0.5mmの長い糸から織られたものである。この糸は、3〜5μmの単繊維(elementary filament)の束から構成されている。織物上へのパラジウムの付着は、Chem.Eng.Sci.、2002年、第57巻、3453〜3460頁に記載されているように、Na2PdCl4水溶液からイオン交換することによって実施した。原子吸光分析によって測定されたパラジウム担持量は4質量%であり、また、この触媒について、BET法による比表面積および孔径分布に関する特性を決定した。Pd分散度の測定には、パルス法による一酸化炭素の化学吸着を用いた。上記Chem.Eng.Sci.を参照されたい。
実験の構成は上述したChem.Eng.Sci.に詳述されている。
Claims (11)
- 2−ブチン−1,4−ジオールを構造化触媒の存在下かつ溶媒の非存在下に水素化することを含む、2−ブテン−1,4−ジオールの調製方法であって、
前記構造化触媒は担体と該担体に担持された触媒金属とを含み、前記担体はセラミック担体または繊維担体であり、前記触媒金属は、パラジウム、白金、イリジウム、ロジウム、ルテニウムおよびそれらの組合せから選ばれる貴金属である、方法。 - 前記構造化触媒の担体が繊維織布である、請求項1に記載の方法。
- 繊維織布が活性炭素繊維から作製されている、請求項2に記載の方法。
- 前記活性炭素繊維がポリアクリロニトリル繊維から作製されている、請求項3に記載の方法。
- 前記繊維の直径が2μm〜100μmである、請求項2〜4のいずれか一項に記載の方法。
- 前記繊維の直径が2μm〜20μmである、請求項2〜5のいずれか一項に記載の方法。
- 前記織布の間隙の寸法が1mm未満である、請求項2〜6のいずれか一項に記載の方法。
- 触媒金属がパラジウムである、請求項2〜7のいずれか一項に記載の方法。
- 前記担体の触媒金属担持量が1〜10質量%である、請求項1〜8のいずれか一項に記載の方法。
- 前記水素化が0.1〜6MPaの圧力で実施される、請求項1〜9のいずれか一項に記載の方法。
- 前記水素化が350K〜500Kの温度で実施される、請求項1〜10のいずれか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05000227 | 2005-01-07 | ||
EP05000227.8 | 2005-01-07 | ||
PCT/EP2005/014103 WO2006072441A2 (en) | 2005-01-07 | 2005-12-29 | Process for the preparation of 22-butene-1.4-diol |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008526797A JP2008526797A (ja) | 2008-07-24 |
JP4960886B2 true JP4960886B2 (ja) | 2012-06-27 |
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007549826A Active JP4960886B2 (ja) | 2005-01-07 | 2005-12-29 | 2−ブテン−1,4−ジオールの調製方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US7541501B2 (ja) |
EP (1) | EP1833779B1 (ja) |
JP (1) | JP4960886B2 (ja) |
KR (1) | KR101226317B1 (ja) |
CN (1) | CN101098842A (ja) |
WO (1) | WO2006072441A2 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP3173398B1 (en) * | 2014-07-23 | 2020-12-09 | Fundación Tecnalia Research & Innovation | Method for manufacturing 2,3-butanediol |
CN109622049B (zh) * | 2018-12-21 | 2021-10-19 | 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 |
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 EP EP05824627.3A patent/EP1833779B1/en active Active
- 2005-12-29 US US11/794,240 patent/US7541501B2/en active Active
- 2005-12-29 JP JP2007549826A patent/JP4960886B2/ja active Active
- 2005-12-29 WO PCT/EP2005/014103 patent/WO2006072441A2/en active Application Filing
- 2005-12-29 CN CNA200580046190XA patent/CN101098842A/zh active Pending
- 2005-12-29 KR KR1020077015411A patent/KR101226317B1/ko active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
EP1833779B1 (en) | 2014-05-07 |
WO2006072441A2 (en) | 2006-07-13 |
WO2006072441A3 (en) | 2006-10-19 |
KR20070091640A (ko) | 2007-09-11 |
EP1833779A2 (en) | 2007-09-19 |
CN101098842A (zh) | 2008-01-02 |
US7541501B2 (en) | 2009-06-02 |
KR101226317B1 (ko) | 2013-01-24 |
JP2008526797A (ja) | 2008-07-24 |
US20080312475A1 (en) | 2008-12-18 |
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