CN1280281C - 3,4-四氢呋喃二醇氢化成四氢呋喃 - Google Patents
3,4-四氢呋喃二醇氢化成四氢呋喃 Download PDFInfo
- Publication number
- CN1280281C CN1280281C CNB028224965A CN02822496A CN1280281C CN 1280281 C CN1280281 C CN 1280281C CN B028224965 A CNB028224965 A CN B028224965A CN 02822496 A CN02822496 A CN 02822496A CN 1280281 C CN1280281 C CN 1280281C
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- CN
- China
- Prior art keywords
- tetrahydrofuran
- thf
- metal
- metal catalyst
- alkane
- Prior art date
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- 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
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- 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)
Abstract
Description
实施例 | 温度(℃) | H2压力(psi) | 催化剂 | 溶剂 | 浓度(%) | FURSel(%) | DHFSel(%) | 四氢呋喃(%) | TOTSel(%) | 3-四氢呋喃(%) | GBLSel(%) | 1,4-BDOSel(%) |
1 | 200 | 500 | 10%Re/1%Ni/C | 二烷 | 94.9 | 0.0 | 0.2 | 53.5 | 56.4 | 0.0 | 2.7 | 0.0 |
2 | 200 | 500 | 10%Re/1%Pd/C | 二烷 | 95.4 | 0.0 | 0.2 | 49.7 | 54.7 | 1.6 | 3.2 | 0.0 |
3 | 200 | 500 | 10%Re/1%Ru/C | 二烷 | 93.1 | 0.0 | 0.1 | 45.4 | 49.5 | 0.0 | 3.9 | 0.0 |
4 | 200 | 500 | 10%Re/1%Rh/C | 二烷 | 94.2 | 0.0 | 0.2 | 41.3 | 45.2 | 2.0 | 1.8 | 0.0 |
5 | 200 | 500 | 20%Re/Calsicat C | 二烷 | 100.0 | 0.6 | 0.0 | 39.0 | 64.8 | 1.0 | 12.3 | 11.9 |
6 | 200 | 500 | 10%Re/Calsicat C | 二烷 | 86.1 | 0.8 | 0.0 | 38.9 | 67.2 | 0.9 | 10.7 | 16.0 |
7 | 200 | 500 | 10%Re/1%Pt/C | 二烷 | 94.2 | 0.0 | 0.3 | 34.8 | 36.2 | 0.0 | 1.1 | 0.0 |
8 | 200 | 500 | 10%Re/Calsicat C | 二烷 | 87.8 | 0.7 | 0.0 | 34.6 | 61.6 | 0.9 | 10.4 | 15.0 |
9 | 200 | 500 | 10%Re/1%Au/C | 二烷 | 97.9 | 0.3 | 0.0 | 29.6 | 39.6 | 0.9 | 8.7 | 0.0 |
10 | 200 | 500 | 20%Re/Calsicat C | 二烷 | 95.5 | 0.7 | 0.0 | 28.5 | 47.1 | 0.9 | 9.2 | 7.8 |
11 | 200 | 500 | 5%Re/Calsicat C | 二烷 | 70.0 | 0.5 | 0.1 | 28.0 | 73.9 | 1.0 | 12.4 | 31.7 |
12 | 200 | 500 | 5%Re/Calsicat C | 二烷 | 66.8 | 0.5 | 0.1 | 25.5 | 64.8 | 0.9 | 10.1 | 27.6 |
13 | 200 | 500 | 20%Re/Sibunit C | 二烷 | 34.0 | 1.0 | 0.0 | 20.8 | 77.8 | 2.5 | 8.7 | 44.9 |
14 | 200 | 500 | 5%Rh/Calsicat C | 二烷 | 22.3 | 0.0 | 0.0 | 19.8 | 33.7 | 13.7 | 0.0 | 0.2 |
实施例 | 温度(℃) | H2压力(psi) | 催化剂 | 溶剂 | 浓度(%) | FURSel(%) | DHFSel(%) | 四氢呋喃(%) | ToTSel(%) | 3-四氢呋喃(%) | GBLSel(%) | 1,4-BDOSel(%) |
15 | 200 | 600 | 20%Re/Sibunit C | 二烷 | 26.5 | 1.2 | 0.0 | 18.1 | 97.2 | 3.9 | 8.7 | 65.3 |
16 | 200 | 500 | 5%Re/SiO2 | 无 | 4.8 | 6.3 | 3.1 | 17.6 | 84.4 | 1.5 | 3.1 | 52.8 |
17 | 200 | 500 | 5%Re/Calsicat C | 二烷 | 32.9 | 2.1 | 15.9 | 16.5 | 67.7 | 1.2 | 7.7 | 24.3 |
18 | 200 | 500 | 5%Re/Sibunit C | 无 | 40.5 | 0.6 | 3.6 | 12.8 | 61.9 | 0.6 | 5.3 | 39.1 |
19 | 200 | 500 | 5%Re/Sibunit C | 二烷 | 16.1 | 1.0 | 1.2 | 125 | 91.7 | 1.1 | 9.0 | 66.9 |
20 | 200 | 500 | 5%Re/Calsicat C | 无 | 86.6 | 0.4 | 2.5 | 11.6 | 16.3 | 0.3 | 1.1 | 0.5 |
21 | 200 | 500 | 10%Re/Sibunit C | 二烷 | 40.9 | 0.5 | 0.3 | 10.4 | 82.1 | 1.2 | 8.7 | 60.9 |
22 | 200 | 500 | 10%Re/Slbunit C | 二烷 | 35.2 | 0.5 | 0.2 | 10.4 | 96.6 | 1.4 | 8.8 | 75.2 |
23 | 200 | 500 | 5%Re/Slbunit C | 二烷 | 25.2 | 0.4 | 0.8 | 9.3 | 88.6 | 1.0 | 7.6 | 69.6 |
24 | 200 | 500 | 5%Re/Calsicat C | EGDME | 99.8 | 1.4 | 15.9 | 8.4 | 29.8 | 0.3 | 3.0 | 0.8 |
25 | 200 | 500 | 5%Re/Al2O3 | EGDME | 46.0 | 1.1 | 1.8 | 8.3 | 34.3 | 1.0 | 1.9 | 20.3 |
26 | 200 | 500 | 5%Re/Calgon C | EGDME | 74.6 | 0.7 | 3.9 | 7.2 | 62.9 | 0.2 | 10.1 | 40.7 |
27 | 200 | 500 | 5%Re/Sibunit C | EGDME | 70.4 | 0.8 | 5.4 | 7.0 | 54.4 | 0.3 | 7.0 | 33.9 |
28 | 175 | 500 | 5%Re/Sibunit C | EGDME | 42.3 | 0.3 | 8.4 | 6.7 | 28.7 | 0.1 | 1.2 | 11.9 |
29 | 200 | 500 | 5%Re/Calgon C | 无 | 62.1 | 0.3 | 0.7 | 6.2 | 55.9 | 0.3 | 2.3 | 46.1 |
30 | 150 | 500 | 5%Re/Calgon C | EGDME | 45.6 | 0.2 | 15.5 | 6.1 | 37.0 | 0.0 | 1.6 | 13.6 |
实施例 | 温度(℃) | H2压力(psi) | 催化剂 | 溶剂 | 浓度(%) | FURSel(%) | DHFSel(%) | 四氢呋喃(%) | TOTSel(%) | 3-四氢呋喃(%) | GBLSel(%) | 1.4-BDOSel(%) |
31 | 175 | 500 | 5%Re/Calsicat C | EGDME | 100.0 | 0.6 | 26.8 | 6.1 | 35.8 | 0.1 | 1.3 | 0.9 |
32 | 150 | 500 | 5%Re/Sibunit C | EGDME | 27.9 | 0.5 | 3.2 | 6.0 | 17.2 | 0.0 | 0.5 | 7.1 |
33 | 200 | 500 | 5%Rh/Sibunit C | 二烷 | 8.7 | 0.7 | 5.1 | 5.9 | 44.9 | 33.2 | 0.0 | 0.0 |
34 | 150 | 500 | 5%Re/Al2O3 | EGDME | 29.8 | 0.3 | 1.1 | 5.6 | 15.4 | 0.1 | 0.3 | 7.9 |
35 | 200 | 500 | 5%Re/Al2O3 | 二烷 | 10.8 | 2.0 | 5.6 | 5.3 | 78.2 | 2.1 | 4.7 | 58.5 |
36 | 200 | 500 | 5%Re/Al2O3 | 无 | 29.5 | 0.3 | 0.7 | 4.9 | 40.0 | 0.8 | 1.6 | 31.7 |
37 | 200 | 500 | 5%Rh/Calgon C | 二烷 | 4.4 | 0.8 | 0.0 | 4.5 | 37.3 | 32.1 | 0.0 | 0.0 |
38 | 175 | 500 | 5%Re/Calgon C | EGDME | 61.3 | 0.3 | 11.8 | 4.5 | 42.9 | 0.1 | 3.9 | 22.4 |
39 | 200 | 500 | 5%Re/SiO2 | 二烷 | 2.2 | 0.0 | 16.0 | 4.5 | 40.1 | 0.0 | 2.3 | 17.4 |
40 | 200 | 60 | 5%Re/SiO2 | 无 | 12.5 | 0.8 | 10.3 | 4.3 | 22.8 | 0.0 | 1.1 | 6.1 |
41 | 175 | 500 | 5%Re/Al2O3 | EGDME | 43.4 | 0.3 | 1.5 | 4.0 | 16.2 | 0.3 | 0.4 | 9.7 |
42 | 200 | 500 | 5%Re/Calgon C | 二烷 | 22.7 | 0.3 | 6.7 | 4.0 | 66.7 | 0.5 | 7.7 | 47.5 |
43 | 150 | 500 | 5%Re/Calsicat C | EGDME | 67.1 | 0.3 | 39.8 | 4.0 | 45.4 | 0.1 | 0.3 | 0.9 |
44 | 200 | 500 | 5%Re/Sibunit C | 二烷 | 11.8 | 2.4 | 16.7 | 3.7 | 81.8 | 0.9 | 8.0 | 50.1 |
45 | 200 | 500 | 5%Re/SiO2 | EGDME | 23.6 | 0.9 | 1.9 | 3.6 | 12.8 | 0.3 | 0.6 | 5.6 |
实施例 | 温度(℃) | H2压力(psi) | 催化剂 | 溶剂 | 浓度(%) | FURSel(%) | DHFSel(%) | 四氢呋喃(%) | ToTSel(%) | 3-四氢呋喃(%) | GBLSel(%) | 1,4-BDOSel(%) |
46 | 200 | 500 | 5%Ni/Calsicat C | 二烷 | 2.4 | 1.2 | 1.6 | 2.8 | 5.6 | 0.0 | 0.0 | 0.0 |
47 | 200 | 500 | 5%Rh/Calsicat C | EGDME | 35.0 | 0.3 | 0.0 | 2.7 | 12.0 | 8.5 | 0.3 | 0.2 |
48 | 200 | 500 | 5%Pd/Sibunit C | 无 | 35.7 | 0.0 | 0.0 | 2.6 | 19.8 | 17.2 | 0.0 | 0.0 |
49 | 200 | 60 | 5%Re/Al2O3 | 无 | 35.3 | 0.8 | 6.2 | 2.5 | 23.3 | 0.3 | 3.6 | 9.8 |
50 | 200 | 500 | 5%Ni/SiO2 | 二烷 | 2.6 | 0.0 | 8.0 | 2.2 | 12.0 | 1.8 | 0.0 | 0.0 |
51 | 200 | 500 | 5%Pd/Calgon C | 无 | 39.8 | 0.1 | 0.0 | 2.1 | 14.3 | 12.2 | 0.0 | 0.0 |
52 | 200 | 500 | 5%Ni/Sibunit C | 二烷 | 6.9 | 0.8 | 1.6 | 1.9 | 4.2 | 0.0 | 0.0 | 0.0 |
53 | 175 | 500 | 5%Re/SiO2 | EGDME | 32.7 | 0.4 | 3.5 | 1.8 | 7.5 | 0.0 | 0.2 | 1.6 |
54 | 200 | 500 | 5%Rh/Al2O3 | 二烷 | 59.3 | 0.1 | 0.0 | 1.8 | 12.9 | 11.0 | 0.0 | 0.1 |
55 | 200 | 500 | 5%Pd/calsicat C | 无 | 64.4 | 0.4 | 0.3 | 1.6 | 7.2 | 4.9 | 0.0 | 0.0 |
56 | 200 | 500 | 5%Rh/Al2O3 | EGDME | 62.4 | 0.1 | 0.0 | 1.3 | 11.7 | 10.2 | 0.1 | 0.0 |
57 | 200 | 500 | 5%Rh/Sibunit C | EGDME | 19.1 | 0.5 | 0.0 | 1.1 | 11.3 | 9.3 | 0.4 | 0.0 |
58 | 150 | 500 | 5%Re/SiO2 | EGDME | 24.2 | 0.3 | 2.7 | 1.1 | 4.8 | 0.0 | 0.3 | 0.5 |
59 | 200 | 500 | 5%Ni/Calgon C | 二烷 | 6.7 | 0.0 | 0.9 | 1.0 | 1.9 | 0.0 | 0.0 | 0.0 |
60 | 200 | 500 | 5%Pd/Al2O3 | 无 | 49.6 | 0.1 | 0.1 | 0.9 | 6.4 | 5.4 | 0.0 | 0.0 |
实施例 | 温度(℃) | H2压力(psi) | 催化剂 | 溶剂 | 浓度(%) | FURSel(%) | DHFSel(%) | 四氢呋喃(%) | TOTSel(%) | 3-四氢呋喃(%) | GBLSel(%) | 1,4-BDOSel(%) |
61 | 200 | 500 | 5%Pd/SiO2 | 无 | 40.3 | 0.8 | 0.0 | 0.8 | 9.8 | 8.2 | 0.0 | 0.0 |
62 | 200 | 500 | 5%Rh/Calgon C | EGDME | 17.9 | 0.0 | 0.0 | 0.6 | 6.4 | 5.5 | 0.3 | 0.0 |
63 | 200 | 500 | 5%Rh/SiO2 | 二烷 | 23.2 | 0.0 | 0.0 | 0.5 | 6.3 | 5.8 | 0.0 | 0.0 |
64 | 200 | 500 | 5%Ru/Al2O3 | 二烷 | 20.5 | 0.2 | 0.0 | 0.4 | 21.5 | 19.1 | 1.7 | 0.0 |
65 | 200 | 500 | 5%Rh/SiO2 | EGDME | 33.0 | 0.2 | 0.0 | 0.3 | 3.9 | 3.1 | 0.4 | 0.0 |
66 | 200 | 500 | 5%Ru/Calsicat C | 二烷 | 51.6 | 0.1 | 0.0 | 0.2 | 8.0 | 3.1 | 4.6 | 0.0 |
67 | 200 | 60 | 5%Re/Calsicat C | 无 | 100.0 | 7.8 | 16.5 | 0.2 | 25.0 | 0.2 | 0.4 | 0.0 |
68 | 200 | 60 | 5%Re/Calgon C | 无 | 73.5 | 20.1 | 34.4 | 0.1 | 56.7 | 0.0 | 1.8 | 0.4 |
69 | 200 | 60 | 5%Re/Sibunit C | 无 | 90.6 | 7.8 | 18.1 | 0.0 | 26.0 | 0.0 | 0.1 | 0.0 |
Claims (32)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US34886301P | 2001-11-13 | 2001-11-13 | |
US60/348,863 | 2001-11-13 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1585761A CN1585761A (zh) | 2005-02-23 |
CN1280281C true CN1280281C (zh) | 2006-10-18 |
Family
ID=23369872
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB028224965A Expired - Fee Related CN1280281C (zh) | 2001-11-13 | 2002-11-13 | 3,4-四氢呋喃二醇氢化成四氢呋喃 |
Country Status (12)
Country | Link |
---|---|
US (1) | US6593481B1 (zh) |
EP (1) | EP1444218B1 (zh) |
JP (1) | JP4473575B2 (zh) |
KR (1) | KR100933612B1 (zh) |
CN (1) | CN1280281C (zh) |
AT (1) | ATE296817T1 (zh) |
BR (1) | BR0214182A (zh) |
CA (1) | CA2466317A1 (zh) |
DE (1) | DE60204479T2 (zh) |
ES (1) | ES2242904T3 (zh) |
HK (1) | HK1074834A1 (zh) |
WO (1) | WO2003042201A1 (zh) |
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 |
US8884035B2 (en) | 2011-12-30 | 2014-11-11 | E I Du Pont De Nemours And Company | Production of tetrahydrofuran-2, 5-dimethanol from isosorbide |
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 |
US8884036B2 (en) | 2011-12-30 | 2014-11-11 | E I Du Pont De Nemours And Company | Production of hydroxymethylfurfural from levoglucosenone |
EP2797868A4 (en) | 2011-12-30 | 2015-08-12 | Du Pont | PROCESS FOR PRODUCING HEXANEDIOLS |
JP2015509088A (ja) | 2011-12-30 | 2015-03-26 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | 1,6−ヘキサンジオールを調製する方法 |
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 |
US8846984B2 (en) | 2012-04-27 | 2014-09-30 | E I Du Pont De Nemours And Company | Production of α,ω-diols |
US8859826B2 (en) | 2012-04-27 | 2014-10-14 | 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 |
US20150298101A1 (en) * | 2012-11-13 | 2015-10-22 | Daicel Corporation | Method for producing 3-hydroxytetrahydrofuran and method for producing 1, 3-butane diol |
MY174111A (en) * | 2013-05-21 | 2020-03-10 | Daicel Corp | Method for producing tetrahydrofuran |
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 |
JP6942738B2 (ja) * | 2017-02-13 | 2021-09-29 | 株式会社ダイセル | 3,4−ジヒドロキシテトラヒドロフランの還元反応用触媒及び3,4−ジヒドロキシテトラヒドロフラン還元物の製造方法 |
KR102610955B1 (ko) * | 2017-12-07 | 2023-12-06 | 주식회사 쿠라레 | 고리형 에테르의 제조 방법 |
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 AT AT02803249T patent/ATE296817T1/de not_active IP Right Cessation
- 2002-11-13 JP JP2003544037A patent/JP4473575B2/ja not_active Expired - Fee Related
- 2002-11-13 EP EP02803249A patent/EP1444218B1/en not_active Expired - Lifetime
- 2002-11-13 WO PCT/US2002/037318 patent/WO2003042201A1/en active IP Right Grant
- 2002-11-13 CN CNB028224965A patent/CN1280281C/zh not_active Expired - Fee Related
- 2002-11-13 ES ES02803249T patent/ES2242904T3/es not_active Expired - Lifetime
- 2002-11-13 CA CA002466317A patent/CA2466317A1/en not_active Abandoned
- 2002-11-13 KR KR1020047007203A patent/KR100933612B1/ko not_active IP Right Cessation
- 2002-11-13 BR BR0214182-5A patent/BR0214182A/pt not_active Application Discontinuation
- 2002-11-13 DE DE60204479T patent/DE60204479T2/de not_active Expired - Lifetime
-
2005
- 2005-08-11 HK HK05106935A patent/HK1074834A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
JP2005511624A (ja) | 2005-04-28 |
CN1585761A (zh) | 2005-02-23 |
ES2242904T3 (es) | 2005-11-16 |
DE60204479T2 (de) | 2006-05-11 |
DE60204479D1 (de) | 2005-07-07 |
ATE296817T1 (de) | 2005-06-15 |
EP1444218A1 (en) | 2004-08-11 |
CA2466317A1 (en) | 2003-05-22 |
WO2003042201A1 (en) | 2003-05-22 |
KR100933612B1 (ko) | 2009-12-23 |
HK1074834A1 (en) | 2005-11-25 |
BR0214182A (pt) | 2004-08-31 |
EP1444218B1 (en) | 2005-06-01 |
US6593481B1 (en) | 2003-07-15 |
KR20050044422A (ko) | 2005-05-12 |
JP4473575B2 (ja) | 2010-06-02 |
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