RU2017122973A - Способ получения 1,4-бутандиола и тетрагидрофурана из фурана - Google Patents
Способ получения 1,4-бутандиола и тетрагидрофурана из фурана Download PDFInfo
- Publication number
- RU2017122973A RU2017122973A RU2017122973A RU2017122973A RU2017122973A RU 2017122973 A RU2017122973 A RU 2017122973A RU 2017122973 A RU2017122973 A RU 2017122973A RU 2017122973 A RU2017122973 A RU 2017122973A RU 2017122973 A RU2017122973 A RU 2017122973A
- Authority
- RU
- Russia
- Prior art keywords
- furan
- catalyst composition
- palladium
- rhenium
- supported catalyst
- Prior art date
Links
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 8
- 239000003054 catalyst Substances 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 229910052763 palladium Inorganic materials 0.000 claims 4
- 229910052702 rhenium Inorganic materials 0.000 claims 4
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 239000008400 supply water Substances 0.000 claims 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims 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
-
- 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
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/656—Manganese, technetium or rhenium
- B01J23/6567—Rhenium
-
- 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
- C07C29/172—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 the obtention of a fully saturated alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/20—Preparation of ethers by reactions not forming ether-oxygen bonds by hydrogenation of carbon-to-carbon double or triple bonds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Claims (7)
1. Способ получения 1,4-бутандиола и тетрагидрофурана, включающий приведение в контакт фурана с водородом и водой в присутствии нанесенной на подложку каталитической композиции, содержащей рений и палладий в массовом соотношении по меньшей мере 1:1, и при этом общее массовое содержание рения и палладия в каталитической композиции составляет от 0,01 до 20 мас. %.
2. Способ по п. 1, отличающийся тем, что подложка в нанесенной на подложку каталитической композиции выбрана из оксидов алюминия, оксидов титана, диоксидов циркония, их смесей и углерода.
3. Способ по п. 1 или 2, отличающийся тем, что рений и палладий предпочтительно присутствуют в нанесенной на подложку каталитической композиции в массовом отношении по меньшей мере 5:1.
4. Способ по п. 2, отличающийся тем, что рений и палладий предпочтительно присутствуют в нанесенной на подложку каталитической композиции в массовом отношении по меньшей мере 10:1.
5. Способ по любому из пп. 1-4, отличающийся тем, что общее количество металлов (рассматриваемых в элементной форме) на катализаторе составляет от 0,1 до 10 мас. %.
6. Способ по любому из пп. 1-5, отличающийся тем, что фуран приводят в контакт с водородом в жидкой фазе в диапазоне температур от 25 до 250°С, давлении от 0,1 до 15 МПа и при молярном отношении H2:фуран от 0,2:1 до 100:1.
7. Способ по любому из пп. 1-6, отличающийся тем, что фуран приводят в контакт с водородом,и совместно подают воду в молярном соотношении вода:фуран в диапазоне от 0,2:1 до 100:1, при температуре от 100 до 350°С, давлении от 0,1 до 15 МПа и при молярном отношении H2:фуран от 0,2:1 до 100:1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14196391 | 2014-12-04 | ||
| EP14196391.8 | 2014-12-04 | ||
| PCT/EP2015/078347 WO2016087508A1 (en) | 2014-12-04 | 2015-12-02 | Process for the production of 1,4-butanediol and tetrahydrofuran from furan |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2017122973A3 RU2017122973A3 (ru) | 2019-01-09 |
| RU2017122973A true RU2017122973A (ru) | 2019-01-09 |
| RU2679639C2 RU2679639C2 (ru) | 2019-02-12 |
Family
ID=52013899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2017122973A RU2679639C2 (ru) | 2014-12-04 | 2015-12-02 | Способ получения 1,4-бутандиола и тетрагидрофурана из фурана |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10023549B2 (ru) |
| EP (1) | EP3227267B1 (ru) |
| CN (1) | CN107001202B (ru) |
| BR (1) | BR112017011750A2 (ru) |
| CA (1) | CA2969160A1 (ru) |
| RU (1) | RU2679639C2 (ru) |
| WO (1) | WO2016087508A1 (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2720682C2 (ru) | 2015-04-09 | 2020-05-12 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ получения 1,4-бутандиола и тетрагидрофурана из фурана |
| CA2997041A1 (en) | 2015-09-10 | 2017-03-16 | Shell Internationale Research Maatschappij B.V. | Process for the production of 1,4-butanediol and tetrahydrofuran from furan |
| CN110997136A (zh) * | 2017-08-10 | 2020-04-10 | 国际壳牌研究有限公司 | 制备催化剂的方法和由呋喃生产1,4-丁二醇和/或四氢呋喃的方法 |
| US20200376477A1 (en) * | 2017-08-10 | 2020-12-03 | Shell Oil Company | Method for preparing a catalyst and method for producing 1,4-butanediol and/or tetrahydrofuran from furan |
| JP2021066707A (ja) * | 2019-10-25 | 2021-04-30 | 学校法人上智学院 | 環状化合物の製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU114928A1 (ru) * | 1958-01-03 | 1958-11-30 | С.Ф. Калинкин | Способ получени 1,4-бутандиола |
| 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 |
| CN1004791B (zh) * | 1983-12-22 | 1989-07-19 | 纳幕尔·杜邦公司 | 钯/铼氢化催化剂及其制造方法 |
| CN1021224C (zh) * | 1985-04-01 | 1993-06-16 | 纳幕尔杜邦公司 | 用钯/铼氢化催化剂制造四氢呋喃、1，4-丁二醇或其混合物的方法 |
| DE4422051A1 (de) * | 1994-06-27 | 1996-01-04 | Basf Ag | Verfahren zur Herstellung von 1,4-Butandiol |
| DE19510438A1 (de) * | 1995-03-22 | 1996-09-26 | Basf Ag | Verfahren zur Herstellung von 1,4-Butandiol und Tetrahydrofuran aus Furan |
| US7935834B2 (en) * | 2004-07-01 | 2011-05-03 | Isp Investments Inc. | Catalysts for maleic acid hydrogenation to 1,4-butanediol |
-
2015
- 2015-12-02 CN CN201580065453.5A patent/CN107001202B/zh active Active
- 2015-12-02 BR BR112017011750A patent/BR112017011750A2/pt active Search and Examination
- 2015-12-02 RU RU2017122973A patent/RU2679639C2/ru active
- 2015-12-02 US US15/533,014 patent/US10023549B2/en active Active
- 2015-12-02 CA CA2969160A patent/CA2969160A1/en not_active Abandoned
- 2015-12-02 EP EP15804441.2A patent/EP3227267B1/en active Active
- 2015-12-02 WO PCT/EP2015/078347 patent/WO2016087508A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| RU2679639C2 (ru) | 2019-02-12 |
| CN107001202B (zh) | 2020-10-30 |
| RU2017122973A3 (ru) | 2019-01-09 |
| CN107001202A (zh) | 2017-08-01 |
| CA2969160A1 (en) | 2016-06-09 |
| EP3227267A1 (en) | 2017-10-11 |
| US10023549B2 (en) | 2018-07-17 |
| BR112017011750A2 (pt) | 2017-12-26 |
| WO2016087508A1 (en) | 2016-06-09 |
| EP3227267B1 (en) | 2019-01-30 |
| US20170320842A1 (en) | 2017-11-09 |
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