CA2466317A1 - Hydrogenation of 3,4-tetrahydrofurandiol to tetrahydrofuran - Google Patents
Hydrogenation of 3,4-tetrahydrofurandiol to tetrahydrofuran Download PDFInfo
- Publication number
- CA2466317A1 CA2466317A1 CA002466317A CA2466317A CA2466317A1 CA 2466317 A1 CA2466317 A1 CA 2466317A1 CA 002466317 A CA002466317 A CA 002466317A CA 2466317 A CA2466317 A CA 2466317A CA 2466317 A1 CA2466317 A1 CA 2466317A1
- Authority
- CA
- Canada
- Prior art keywords
- process according
- tetrahydrofuran
- metal catalyst
- tetrahydrofurandiol
- metal
- 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.)
- Abandoned
Links
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims abstract description 62
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000005984 hydrogenation reaction Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 66
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- 239000002243 precursor Substances 0.000 claims abstract description 23
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 7
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 7
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 6
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 6
- 229910052751 metal Inorganic materials 0.000 claims description 59
- 239000002184 metal Substances 0.000 claims description 59
- UNXHWFMMPAWVPI-UHFFFAOYSA-N butane-1,2,3,4-tetrol Chemical compound OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 150000002739 metals Chemical class 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052737 gold Inorganic materials 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical group OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 9
- 230000000737 periodic effect Effects 0.000 claims description 9
- 229910052697 platinum Inorganic materials 0.000 claims description 9
- 239000004386 Erythritol Substances 0.000 claims description 8
- 230000003197 catalytic effect Effects 0.000 claims description 8
- 229940009714 erythritol Drugs 0.000 claims description 8
- 235000019414 erythritol Nutrition 0.000 claims description 8
- 229910052745 lead Inorganic materials 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 229910052718 tin Inorganic materials 0.000 claims description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 229910052793 cadmium Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 240000008042 Zea mays Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002028 Biomass Substances 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- 241000609240 Ambelania acida Species 0.000 description 3
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical compound OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000010905 bagasse Substances 0.000 description 3
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 3
- -1 hexose sugars Chemical class 0.000 description 3
- 239000010903 husk Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010902 straw Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 241000209761 Avena Species 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000001624 Espostoa lanata Species 0.000 description 1
- 235000009161 Espostoa lanata Nutrition 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229910002621 H2PtCl6 Inorganic materials 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- JQGGAELIYHNDQS-UHFFFAOYSA-N Nic 12 Natural products CC(C=CC(=O)C)c1ccc2C3C4OC4C5(O)CC=CC(=O)C5(C)C3CCc2c1 JQGGAELIYHNDQS-UHFFFAOYSA-N 0.000 description 1
- 229910019891 RuCl3 Inorganic materials 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- SRBFZHDQGSBBOR-LECHCGJUSA-N alpha-D-xylose Chemical compound O[C@@H]1CO[C@H](O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-LECHCGJUSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000010961 commercial manufacture process Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000011094 fiberboard Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- YCGXHXXRKDAINX-UHFFFAOYSA-N oxolane;oxolan-3-ol Chemical compound C1CCOC1.C1CCOC1.OC1CCOC1 YCGXHXXRKDAINX-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000010893 paper waste Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000021092 sugar substitutes Nutrition 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229960003487 xylose Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34886301P | 2001-11-13 | 2001-11-13 | |
| US60/348,863 | 2001-11-13 | ||
| PCT/US2002/037318 WO2003042201A1 (en) | 2001-11-13 | 2002-11-13 | Hydrogenation of 3,4-tetrahydrofurandiol to tetrahydrofuran |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2466317A1 true CA2466317A1 (en) | 2003-05-22 |
Family
ID=23369872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002466317A Abandoned CA2466317A1 (en) | 2001-11-13 | 2002-11-13 | Hydrogenation of 3,4-tetrahydrofurandiol to tetrahydrofuran |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6593481B1 (enExample) |
| EP (1) | EP1444218B1 (enExample) |
| JP (1) | JP4473575B2 (enExample) |
| KR (1) | KR100933612B1 (enExample) |
| CN (1) | CN1280281C (enExample) |
| AT (1) | ATE296817T1 (enExample) |
| BR (1) | BR0214182A (enExample) |
| CA (1) | CA2466317A1 (enExample) |
| DE (1) | DE60204479T2 (enExample) |
| ES (1) | ES2242904T3 (enExample) |
| WO (1) | WO2003042201A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7019155B2 (en) * | 2001-11-13 | 2006-03-28 | Invista North America S.A.R.L. | Hydrogenation of tetrahydroxybutane to tetrahydrofuran |
| US8889912B2 (en) | 2011-12-30 | 2014-11-18 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| US8865940B2 (en) | 2011-12-30 | 2014-10-21 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| CN104024197A (zh) | 2011-12-30 | 2014-09-03 | 纳幕尔杜邦公司 | 己二醇的制备方法 |
| US8884036B2 (en) | 2011-12-30 | 2014-11-11 | E I Du Pont De Nemours And Company | Production of hydroxymethylfurfural from levoglucosenone |
| US8962894B2 (en) | 2011-12-30 | 2015-02-24 | E I Du Pont De Nemours And Company | Process for preparing 1, 6-hexanediol |
| BR112014015994A2 (pt) | 2011-12-30 | 2018-05-22 | Du Pont | processo. |
| JP5797587B2 (ja) * | 2012-03-05 | 2015-10-21 | 株式会社ダイセル | １，４−アンヒドロエリスリトールの水素化分解物の製造方法 |
| US8859826B2 (en) | 2012-04-27 | 2014-10-14 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US8846985B2 (en) | 2012-04-27 | 2014-09-30 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US9018423B2 (en) | 2012-04-27 | 2015-04-28 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| JP6280870B2 (ja) * | 2012-11-13 | 2018-02-14 | 株式会社ダイセル | ３−ヒドロキシテトラヒドロフランの製造方法、１，３−ブタンジオールの製造方法 |
| JP6345654B2 (ja) * | 2013-05-21 | 2018-06-20 | 株式会社ダイセル | テトラヒドロフランの製造方法 |
| CN103861616B (zh) * | 2014-02-24 | 2016-03-09 | 万华化学集团股份有限公司 | 一种催化剂、其制备方法及采用该催化剂联产制备1,4-丁二醇、γ-丁内酯和四氢呋喃的方法 |
| JP6684113B2 (ja) * | 2015-09-08 | 2020-04-22 | 株式会社ダイセル | オレフィン化反応用触媒及びオレフィンの製造方法 |
| MY193459A (en) * | 2017-02-13 | 2022-10-14 | Daicel Corp | Catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran, and method for producing 3,4-dihydroxytetrahydrofuran reduced product |
| US11104655B2 (en) | 2017-12-07 | 2021-08-31 | Kuraray Co., Ltd. | Method for producing cyclic ether |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2572566A (en) * | 1949-01-07 | 1951-10-23 | Phillips Petroleum Co | Process for production of 3, 4-dihydroxytetrahydrofuran |
| US4313884A (en) | 1980-01-21 | 1982-02-02 | Uop Inc. | Use of metal ions in preparation of anhydropolyols |
| US4401823A (en) | 1981-05-18 | 1983-08-30 | Uop Inc. | Hydrogenolysis of polyhydroxylated compounds |
| US4550185A (en) * | 1983-12-22 | 1985-10-29 | E. I. Du Pont De Nemours And Company | Process for making tetrahydrofuran and 1,4-butanediol using Pd/Re hydrogenation catalyst |
| JP2589500B2 (ja) | 1987-08-11 | 1997-03-12 | 三菱化学株式会社 | 電解液用溶媒 |
| US5478952A (en) * | 1995-03-03 | 1995-12-26 | E. I. Du Pont De Nemours And Company | Ru,Re/carbon catalyst for hydrogenation in aqueous solution |
| DE19749202C1 (de) | 1997-11-07 | 1999-05-27 | Degussa | Verfahren zur Herstellung von fünf- oder sechsgliedrigen cyclischen Ethern und Anhydrohexitgemische |
-
2002
- 2002-11-12 US US10/292,557 patent/US6593481B1/en not_active Expired - Lifetime
- 2002-11-13 BR BR0214182-5A patent/BR0214182A/pt not_active Application Discontinuation
- 2002-11-13 ES ES02803249T patent/ES2242904T3/es not_active Expired - Lifetime
- 2002-11-13 EP EP02803249A patent/EP1444218B1/en not_active Expired - Lifetime
- 2002-11-13 CN CNB028224965A patent/CN1280281C/zh not_active Expired - Fee Related
- 2002-11-13 JP JP2003544037A patent/JP4473575B2/ja not_active Expired - Fee Related
- 2002-11-13 KR KR1020047007203A patent/KR100933612B1/ko not_active Expired - Fee Related
- 2002-11-13 WO PCT/US2002/037318 patent/WO2003042201A1/en not_active Ceased
- 2002-11-13 CA CA002466317A patent/CA2466317A1/en not_active Abandoned
- 2002-11-13 AT AT02803249T patent/ATE296817T1/de not_active IP Right Cessation
- 2002-11-13 DE DE60204479T patent/DE60204479T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2242904T3 (es) | 2005-11-16 |
| KR20050044422A (ko) | 2005-05-12 |
| HK1074834A1 (en) | 2005-11-25 |
| JP4473575B2 (ja) | 2010-06-02 |
| US6593481B1 (en) | 2003-07-15 |
| KR100933612B1 (ko) | 2009-12-23 |
| BR0214182A (pt) | 2004-08-31 |
| WO2003042201A1 (en) | 2003-05-22 |
| JP2005511624A (ja) | 2005-04-28 |
| DE60204479T2 (de) | 2006-05-11 |
| CN1280281C (zh) | 2006-10-18 |
| EP1444218A1 (en) | 2004-08-11 |
| DE60204479D1 (de) | 2005-07-07 |
| CN1585761A (zh) | 2005-02-23 |
| EP1444218B1 (en) | 2005-06-01 |
| ATE296817T1 (de) | 2005-06-15 |
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