DE2704500C2 - Verfahren zur Herstellung von Tetrahydrofuran - Google Patents
Verfahren zur Herstellung von TetrahydrofuranInfo
- Publication number
- DE2704500C2 DE2704500C2 DE2704500A DE2704500A DE2704500C2 DE 2704500 C2 DE2704500 C2 DE 2704500C2 DE 2704500 A DE2704500 A DE 2704500A DE 2704500 A DE2704500 A DE 2704500A DE 2704500 C2 DE2704500 C2 DE 2704500C2
- Authority
- DE
- Germany
- Prior art keywords
- distillation column
- tetrahydrofuran
- butanediol
- reaction zone
- distillate
- 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.)
- Expired
Links
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims description 70
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000004821 distillation Methods 0.000 claims description 45
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XUKSWKGOQKREON-UHFFFAOYSA-N 1,4-diacetoxybutane Chemical compound CC(=O)OCCCCOC(C)=O XUKSWKGOQKREON-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- MWWXARALRVYLAE-UHFFFAOYSA-N 2-acetyloxybut-3-enyl acetate Chemical compound CC(=O)OCC(C=C)OC(C)=O MWWXARALRVYLAE-UHFFFAOYSA-N 0.000 description 1
- VIRPYONDKXQHHU-UHFFFAOYSA-N 4-acetyloxybut-3-enyl acetate Chemical compound CC(=O)OCCC=COC(C)=O VIRPYONDKXQHHU-UHFFFAOYSA-N 0.000 description 1
- FLVQOAUAIBIIGO-UHFFFAOYSA-N 4-hydroxybutyl acetate Chemical compound CC(=O)OCCCCO FLVQOAUAIBIIGO-UHFFFAOYSA-N 0.000 description 1
- -1 B. inorganic acids Chemical class 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000006137 acetoxylation reaction Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- REJPDMLLCDXIOV-UHFFFAOYSA-N but-2-ynal Chemical compound CC#CC=O REJPDMLLCDXIOV-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase 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)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1107876A JPS5293763A (en) | 1976-02-04 | 1976-02-04 | Preparation of tetrahydrofuran |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2704500A1 DE2704500A1 (de) | 1977-08-11 |
| DE2704500C2 true DE2704500C2 (de) | 1986-01-02 |
Family
ID=11767935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2704500A Expired DE2704500C2 (de) | 1976-02-04 | 1977-02-03 | Verfahren zur Herstellung von Tetrahydrofuran |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4093633A (enExample) |
| JP (1) | JPS5293763A (enExample) |
| CA (1) | CA1099731A (enExample) |
| DE (1) | DE2704500C2 (enExample) |
| FR (1) | FR2340314A1 (enExample) |
| GB (1) | GB1502591A (enExample) |
| IT (1) | IT1082522B (enExample) |
| NL (1) | NL187911C (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2927931C3 (de) * | 1979-07-11 | 1982-03-11 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur kontinuierlichen Abtrennung von Methanol aus Mischungen von Tetrahydrofuran mit Methanol und Wasser |
| US4348262A (en) * | 1980-05-19 | 1982-09-07 | E. I. Du Pont De Nemours And Company | Refining tetrahydrofuran |
| US4257961A (en) * | 1980-06-11 | 1981-03-24 | E. I. Du Pont De Nemours And Company | Purification of tetrahydrofuran |
| US4413136A (en) * | 1982-08-02 | 1983-11-01 | E. I. Du Pont De Nemours And Company | Purification of tetrahydrofuran |
| JPS6140278A (ja) * | 1984-08-01 | 1986-02-26 | Idemitsu Petrochem Co Ltd | テトラヒドロフランの製造方法 |
| GB8717993D0 (en) * | 1987-07-29 | 1987-09-03 | Davy Mckee Ltd | Process |
| DE3726805A1 (de) | 1987-08-12 | 1989-02-23 | Basf Ag | Verfahren zur destillativen reinigung von tetrahydrofuran |
| US4918204A (en) * | 1989-01-30 | 1990-04-17 | Arco Chemical Technology, Inc. | Tetrahydrofuran purification |
| DE3909485A1 (de) * | 1989-03-22 | 1990-09-27 | Basf Ag | Verfahren zur herstellung von butandiol-1,4 und tetrahydrofuran |
| DE4005293A1 (de) * | 1990-02-20 | 1991-08-22 | Basf Ag | Verfahren zur herstellung von tetrahydrofuran und -butyrolacton |
| US5099039A (en) * | 1990-11-06 | 1992-03-24 | Hoechst Celanese Corp. | Production of the from 1,4-butanediol using a polybenzimidazole catalyst |
| US5166370A (en) * | 1991-04-12 | 1992-11-24 | Arco Chemical Technology, L.P. | Preparation of tetrahydrofuran using a supported transition metal |
| JP3324759B2 (ja) * | 1994-11-08 | 2002-09-17 | イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー | １，４−ブタンジオールからの着色物質の除去方法およびｐｔｍｅｇ製造へのその応用 |
| US6159345A (en) * | 1998-11-06 | 2000-12-12 | Mitsubishi Chemical America, Inc. | Method and apparatus for recovering and/or recycling solvents |
| JP2006137749A (ja) * | 2004-10-14 | 2006-06-01 | Mitsubishi Chemicals Corp | エステルオリゴマーの分解方法及び炭素数４の化合物の製造方法 |
| CN101868449B (zh) * | 2008-11-17 | 2014-10-01 | 巴斯夫欧洲公司 | 制备四氢呋喃的方法 |
| CN102596926A (zh) * | 2009-10-30 | 2012-07-18 | 株式会社日立工业设备技术 | 四氢呋喃的精制方法以及精制系统 |
| JP5817189B2 (ja) * | 2011-04-11 | 2015-11-18 | 三菱化学株式会社 | テトラヒドロフランの製造方法 |
| JP2012236819A (ja) * | 2011-04-27 | 2012-12-06 | Mitsubishi Chemicals Corp | テトラヒドロフランの製造方法 |
| JP2012250967A (ja) * | 2011-06-07 | 2012-12-20 | Mitsubishi Chemicals Corp | テトラヒドロフランの製造方法 |
| JP2012250966A (ja) * | 2011-06-07 | 2012-12-20 | Mitsubishi Chemicals Corp | テトラヒドロフランの製造方法 |
| JP2013060429A (ja) * | 2011-08-23 | 2013-04-04 | Mitsubishi Chemicals Corp | １，４−ブタンジオールの精製方法及びテトラヒドロフランの製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA546591A (en) * | 1957-09-24 | O. Wolf Herbert | Purification and dehydration of tetrahydrofuran | |
| US2544899A (en) * | 1949-06-01 | 1951-03-13 | Eastman Kodak Co | Method for making cyclic ethers |
| DE1043342B (de) * | 1957-11-19 | 1958-11-13 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Tetrahydrofuran |
| GB1170222A (en) * | 1968-06-10 | 1969-11-12 | Shell Int Research | Process for the preparation of Tetrahydrofuran and/or Homologues thereof |
| JPS4920581B1 (enExample) * | 1969-08-14 | 1974-05-25 | ||
| US3726905A (en) * | 1971-07-01 | 1973-04-10 | Du Pont | Conversion of butanediol to tetrahydrofuran in the presence of tall oil |
| DE2442886B2 (de) * | 1974-09-07 | 1976-09-30 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von tetrahydrofuran |
-
1976
- 1976-02-04 JP JP1107876A patent/JPS5293763A/ja active Granted
-
1977
- 1977-01-26 GB GB3212/77A patent/GB1502591A/en not_active Expired
- 1977-01-28 US US05/763,506 patent/US4093633A/en not_active Expired - Lifetime
- 1977-02-02 IT IT67215/77A patent/IT1082522B/it active
- 1977-02-02 NL NLAANVRAGE7701056,A patent/NL187911C/xx not_active IP Right Cessation
- 1977-02-03 DE DE2704500A patent/DE2704500C2/de not_active Expired
- 1977-02-04 CA CA271,077A patent/CA1099731A/en not_active Expired
- 1977-02-04 FR FR7703191A patent/FR2340314A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL187911B (nl) | 1991-09-16 |
| JPS5293763A (en) | 1977-08-06 |
| FR2340314A1 (fr) | 1977-09-02 |
| GB1502591A (en) | 1978-03-01 |
| FR2340314B1 (enExample) | 1980-12-12 |
| NL7701056A (nl) | 1977-08-08 |
| US4093633A (en) | 1978-06-06 |
| CA1099731A (en) | 1981-04-21 |
| DE2704500A1 (de) | 1977-08-11 |
| IT1082522B (it) | 1985-05-21 |
| NL187911C (nl) | 1992-02-17 |
| JPS5343504B2 (enExample) | 1978-11-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8339 | Ceased/non-payment of the annual fee |