JPS5883028A - ポリテトラメチレングリコ−ルの製造方法 - Google Patents
ポリテトラメチレングリコ−ルの製造方法Info
- Publication number
- JPS5883028A JPS5883028A JP18073881A JP18073881A JPS5883028A JP S5883028 A JPS5883028 A JP S5883028A JP 18073881 A JP18073881 A JP 18073881A JP 18073881 A JP18073881 A JP 18073881A JP S5883028 A JPS5883028 A JP S5883028A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- carboxylic acid
- chloride
- tetrahydrofuran
- anhydride
- 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.)
- Granted
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 8
- -1 polytetramethylene Polymers 0.000 title claims abstract description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 239000011964 heteropoly acid Substances 0.000 claims abstract description 12
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims abstract description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 4
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 abstract description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 230000007797 corrosion Effects 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- BJZYYSAMLOBSDY-QMMMGPOBSA-N (2s)-2-butoxybutan-1-ol Chemical compound CCCCO[C@@H](CC)CO BJZYYSAMLOBSDY-QMMMGPOBSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- OHAVYOCBYILSBZ-UHFFFAOYSA-M dihydroxyboron;hydroxy(dioxo)tungsten Chemical compound O[B]O.O[W](=O)=O OHAVYOCBYILSBZ-UHFFFAOYSA-M 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Polyethers (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18073881A JPS5883028A (ja) | 1981-11-10 | 1981-11-10 | ポリテトラメチレングリコ−ルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18073881A JPS5883028A (ja) | 1981-11-10 | 1981-11-10 | ポリテトラメチレングリコ−ルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5883028A true JPS5883028A (ja) | 1983-05-18 |
| JPS637571B2 JPS637571B2 (en]) | 1988-02-17 |
Family
ID=16088442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18073881A Granted JPS5883028A (ja) | 1981-11-10 | 1981-11-10 | ポリテトラメチレングリコ−ルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5883028A (en]) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59159824A (ja) * | 1983-03-02 | 1984-09-10 | Asahi Glass Co Ltd | ポリエ−テル化合物の製造方法 |
| JPS61123629A (ja) * | 1984-11-20 | 1986-06-11 | Asahi Chem Ind Co Ltd | ポリアルキレンエ−テル中に含まれるヘテロポリ酸の除去方法 |
| US4658065A (en) * | 1984-03-28 | 1987-04-14 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing polyether polyol and a product |
| US5282929A (en) * | 1992-03-06 | 1994-02-01 | E. I. Du Pont De Nemours And Company | Reducing molecular weight distribution of polyether glycols by short-path distillation |
| US5416240A (en) * | 1991-03-13 | 1995-05-16 | Basf Aktiengesellschaft | Preparation of poloxy-alkylene glycols |
| WO1996013477A1 (en) * | 1994-10-27 | 1996-05-09 | Mobil Oil Corporation | Polyether lubricants |
| US5741888A (en) * | 1994-10-07 | 1998-04-21 | Basf Aktiengesellschaft | Removal of heteropoly compounds from polyethers, polyesters and polyether esters |
| US5756604A (en) * | 1995-08-31 | 1998-05-26 | Hodogaya Chemical Co., Ltd. | Process for producing polyether, and process for recycling and reusing herteropolyacid |
| US6043338A (en) * | 1995-07-27 | 2000-03-28 | Basf Aktiengesellschaft | Method of producing polyoxytetramethylene glycol |
| US6087307A (en) * | 1998-11-17 | 2000-07-11 | Mobil Oil Corporation | Polyether fluids miscible with non-polar hydrocarbon lubricants |
-
1981
- 1981-11-10 JP JP18073881A patent/JPS5883028A/ja active Granted
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59159824A (ja) * | 1983-03-02 | 1984-09-10 | Asahi Glass Co Ltd | ポリエ−テル化合物の製造方法 |
| US4658065A (en) * | 1984-03-28 | 1987-04-14 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing polyether polyol and a product |
| US4792627A (en) * | 1984-03-28 | 1988-12-20 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing polyether polyol and a product |
| JPS61123629A (ja) * | 1984-11-20 | 1986-06-11 | Asahi Chem Ind Co Ltd | ポリアルキレンエ−テル中に含まれるヘテロポリ酸の除去方法 |
| US5416240A (en) * | 1991-03-13 | 1995-05-16 | Basf Aktiengesellschaft | Preparation of poloxy-alkylene glycols |
| US5302255A (en) * | 1992-03-06 | 1994-04-12 | E. I. Du Pont De Nemours And Company | Reducing molecular weight distribution of polyether glycols by short-path distillation |
| US5282929A (en) * | 1992-03-06 | 1994-02-01 | E. I. Du Pont De Nemours And Company | Reducing molecular weight distribution of polyether glycols by short-path distillation |
| US5741888A (en) * | 1994-10-07 | 1998-04-21 | Basf Aktiengesellschaft | Removal of heteropoly compounds from polyethers, polyesters and polyether esters |
| WO1996013477A1 (en) * | 1994-10-27 | 1996-05-09 | Mobil Oil Corporation | Polyether lubricants |
| US5648557A (en) * | 1994-10-27 | 1997-07-15 | Mobil Oil Corporation | Polyether lubricants and method for their production |
| AU697555B2 (en) * | 1994-10-27 | 1998-10-08 | Mobil Oil Corporation | Polyether lubricants |
| CN1101412C (zh) * | 1994-10-27 | 2003-02-12 | 美孚石油公司 | 使环醚单体聚合以生产聚氧化烯聚合物的方法 |
| US6043338A (en) * | 1995-07-27 | 2000-03-28 | Basf Aktiengesellschaft | Method of producing polyoxytetramethylene glycol |
| US5756604A (en) * | 1995-08-31 | 1998-05-26 | Hodogaya Chemical Co., Ltd. | Process for producing polyether, and process for recycling and reusing herteropolyacid |
| US6087307A (en) * | 1998-11-17 | 2000-07-11 | Mobil Oil Corporation | Polyether fluids miscible with non-polar hydrocarbon lubricants |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS637571B2 (en]) | 1988-02-17 |
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