DE2332906A1 - Verfahren zur herstellung von tetrahydrofuran - Google Patents
Verfahren zur herstellung von tetrahydrofuranInfo
- Publication number
- DE2332906A1 DE2332906A1 DE2332906A DE2332906A DE2332906A1 DE 2332906 A1 DE2332906 A1 DE 2332906A1 DE 2332906 A DE2332906 A DE 2332906A DE 2332906 A DE2332906 A DE 2332906A DE 2332906 A1 DE2332906 A1 DE 2332906A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- copper
- chromium
- zinc
- tetrahydrofuran
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims description 32
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 52
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- XUZDJUDKWXESQE-UHFFFAOYSA-N chromium copper zinc Chemical compound [Cr].[Zn].[Cu] XUZDJUDKWXESQE-UHFFFAOYSA-N 0.000 claims description 14
- 230000018044 dehydration Effects 0.000 claims description 11
- 238000006297 dehydration reaction Methods 0.000 claims description 11
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 238000001354 calcination Methods 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 239000011651 chromium Substances 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- 239000012535 impurity Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/868—Chromium copper and chromium
-
- 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
- B01J35/19—Catalysts containing parts with different compositions
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47093457A JPS4949953A (enExample) | 1972-09-18 | 1972-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2332906A1 true DE2332906A1 (de) | 1974-04-04 |
Family
ID=14082846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2332906A Pending DE2332906A1 (de) | 1972-09-18 | 1973-06-28 | Verfahren zur herstellung von tetrahydrofuran |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3894054A (enExample) |
| JP (1) | JPS4949953A (enExample) |
| DE (1) | DE2332906A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0322140A1 (en) * | 1987-12-23 | 1989-06-28 | The Standard Oil Company | Vapor-phase hydrogenation of maleic anhydride to tetrahydrofuran and gamma-butyrolactone |
| WO2005058491A1 (de) * | 2003-12-09 | 2005-06-30 | Basf Aktiengesellschaft | Katalysatorextrudate auf basis kupferoxid und ihre verwendung zur hydrierung von carbonylverbindungen |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4810807A (en) * | 1987-10-13 | 1989-03-07 | The Standard Oil Company | Hydrogenation of maleic anhydride to tetrahydrofuran |
| US4965378A (en) * | 1987-12-23 | 1990-10-23 | The Standard Oil Company | Vapor-phase hydrogenation of maleic anhydride to tetrahydrofuran and gamma-butyrolactone |
| US5345005A (en) * | 1989-09-12 | 1994-09-06 | Engelhard Corporation | Hydrogenation catalyst, process for preparing and process of using said catalyst |
| US5155086A (en) * | 1989-09-12 | 1992-10-13 | Engelhard Corporation | Hydrogenation catalyst, process for preparing and process of using said catalyst |
| US5134108A (en) * | 1991-05-22 | 1992-07-28 | Engelhard Corporation | Process for preparing catalyst with copper or zinc and with chromium, molybdenum, tungsten, or vanadium, and product thereof |
| US5149836A (en) * | 1991-07-25 | 1992-09-22 | Isp Investments Inc. | Process for the production of gamma butyrolactone THF in predetermined amounts |
| US6357374B1 (en) * | 2000-07-21 | 2002-03-19 | Cortana Corporation | Method and apparatus for increasing the effectiveness and efficiency of multiple boundary layer control techniques |
| KR20240128823A (ko) | 2021-11-05 | 2024-08-27 | 다우 글로벌 테크놀로지스 엘엘씨 | 술폰산 작용화된 SiO2 담체 상 전이 금속을 포함하는 불균일 촉매 및 이러한 촉매의 에테르 제조 방법에서의 용도 |
| JP2024542947A (ja) | 2021-11-05 | 2024-11-19 | ダウ グローバル テクノロジーズ エルエルシー | ゼオライト担体上の遷移金属を含む不均一系触媒を用いたエーテルを製造するためのプロセス |
| CN120112505A (zh) | 2022-10-31 | 2025-06-06 | 陶氏环球技术有限责任公司 | 包含沸石载体上的铂和钌的非均相催化剂以及此类催化剂在用于生产醚的方法中的用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2130501A (en) * | 1934-06-27 | 1938-09-20 | Du Pont | Reduction of cyclic ethers |
| US3370067A (en) * | 1967-04-07 | 1968-02-20 | Shell Oil Co | Hydrogenolysis of butyrolactone and gamma-valerolactone to the corresponding cyclic ethers |
-
1972
- 1972-09-18 JP JP47093457A patent/JPS4949953A/ja active Pending
-
1973
- 1973-06-28 DE DE2332906A patent/DE2332906A1/de active Pending
- 1973-07-05 US US376724A patent/US3894054A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0322140A1 (en) * | 1987-12-23 | 1989-06-28 | The Standard Oil Company | Vapor-phase hydrogenation of maleic anhydride to tetrahydrofuran and gamma-butyrolactone |
| WO2005058491A1 (de) * | 2003-12-09 | 2005-06-30 | Basf Aktiengesellschaft | Katalysatorextrudate auf basis kupferoxid und ihre verwendung zur hydrierung von carbonylverbindungen |
| US7459571B2 (en) | 2003-12-09 | 2008-12-02 | Basf Aktiengesellschaft | Catalyst extrudates based on copper oxide and their use for hydrogenating carbonyl compounds |
| CN100496718C (zh) * | 2003-12-09 | 2009-06-10 | 巴斯福股份公司 | 基于氧化铜的催化剂挤出物及其用于氢化羰基化合物的用途 |
| US7807603B2 (en) | 2003-12-09 | 2010-10-05 | Basf Aktiengesellschaft | Catalyst extrudates based on copper oxide and their use for hydrogenating carbonyl compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4949953A (enExample) | 1974-05-15 |
| US3894054A (en) | 1975-07-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |