DE2760272C2 - Verfahren zur Herstellung von Poly-(tetramethylenether)-glykol durch Alkoholyse eines Ester-Endgruppen aufweisenden Poly-(tetramethylenether)-glykols - Google Patents
Verfahren zur Herstellung von Poly-(tetramethylenether)-glykol durch Alkoholyse eines Ester-Endgruppen aufweisenden Poly-(tetramethylenether)-glykolsInfo
- Publication number
- DE2760272C2 DE2760272C2 DE19772760272 DE2760272A DE2760272C2 DE 2760272 C2 DE2760272 C2 DE 2760272C2 DE 19772760272 DE19772760272 DE 19772760272 DE 2760272 A DE2760272 A DE 2760272A DE 2760272 C2 DE2760272 C2 DE 2760272C2
- Authority
- DE
- Germany
- Prior art keywords
- poly
- glycol
- tetramethylene ether
- alcoholysis
- catalyst
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 20
- -1 poly(tetramethylene ether) Polymers 0.000 title claims description 15
- 238000006136 alcoholysis reaction Methods 0.000 title claims description 13
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000004185 ester group Chemical group 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 229910052788 barium Inorganic materials 0.000 claims description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052712 strontium Inorganic materials 0.000 claims description 4
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 14
- 239000000292 calcium oxide Substances 0.000 description 7
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005048 flame photometry Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/20—Tetrahydrofuran
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US67255576A | 1976-03-31 | 1976-03-31 | |
US67255676A | 1976-03-31 | 1976-03-31 | |
US67255776A | 1976-03-31 | 1976-03-31 | |
US75121176A | 1976-12-16 | 1976-12-16 | |
US76751077A | 1977-02-14 | 1977-02-14 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2760272A1 DE2760272A1 (US08080257-20111220-C00005.png) | 1985-05-09 |
DE2760272C2 true DE2760272C2 (de) | 1987-04-16 |
Family
ID=27542063
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19772709280 Expired DE2709280C2 (de) | 1976-03-31 | 1977-03-03 | Verfahren zur Herstellung von Poly-(tetramethylenether)-glykol |
DE19772760272 Expired DE2760272C2 (de) | 1976-03-31 | 1977-03-03 | Verfahren zur Herstellung von Poly-(tetramethylenether)-glykol durch Alkoholyse eines Ester-Endgruppen aufweisenden Poly-(tetramethylenether)-glykols |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19772709280 Expired DE2709280C2 (de) | 1976-03-31 | 1977-03-03 | Verfahren zur Herstellung von Poly-(tetramethylenether)-glykol |
Country Status (7)
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2964245D1 (en) * | 1978-03-16 | 1983-01-20 | Du Pont | Polyurethanes prepared with tetrahydrofuran-alkylene oxide polymerizates having low oligomeric cyclic ether content, processes for preparing the same, and articles and fibers of the polyurethanes |
FR2429802A1 (fr) * | 1978-06-30 | 1980-01-25 | Du Pont | Procede perfectionne pour preparer des copolyether glycols a groupes terminaux ester |
DE3004328A1 (de) * | 1980-02-06 | 1981-08-13 | Bayer Ag, 5090 Leverkusen | Polytetrahydrofurane mit acrylat- oder methacrylatendgruppen |
DE3013927A1 (de) * | 1980-04-11 | 1981-10-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von hydroxylgruppenhaltigen polmeren |
US4393199A (en) | 1981-05-12 | 1983-07-12 | S R I International | Cationic polymerization |
DE3410069A1 (de) * | 1984-03-20 | 1985-10-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von hydroxylgruppen enthaltenden polymeren |
DE4325023A1 (de) * | 1993-07-26 | 1995-02-02 | Basf Ag | Verfahren zur Herstellung von Polytetrahydrofuran oder Tetrahydrofuran-Alkylenoxid-Copolymeren |
DE19527532A1 (de) * | 1995-07-27 | 1997-01-30 | Basf Ag | Verfahren zur Herstellung von Polyoxytetramethylenglycol |
DE19719875A1 (de) * | 1997-05-12 | 1998-11-19 | Basf Ag | Verfahren zur Polymerisation cyclischer Ether |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1073230A (en) * | 1962-11-23 | 1967-06-21 | Eastman Kodak Co | Preparation of poly(tetramethylene glycol) and also of elastomeric polyesters formed thereform |
JPS5232677B2 (US08080257-20111220-C00005.png) * | 1972-12-29 | 1977-08-23 | ||
DE2445961C2 (de) * | 1974-09-26 | 1983-12-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Polymerisation von Tetrahydrofuran |
-
1977
- 1977-03-03 DE DE19772709280 patent/DE2709280C2/de not_active Expired
- 1977-03-03 DE DE19772760272 patent/DE2760272C2/de not_active Expired
- 1977-03-24 FR FR7708800A patent/FR2357591A1/fr active Granted
- 1977-03-29 IT IT2183977A patent/IT1104560B/it active
- 1977-03-30 BE BE176242A patent/BE853028A/xx not_active IP Right Cessation
- 1977-03-30 PL PL19704177A patent/PL114086B1/pl unknown
- 1977-03-30 NL NL7703462A patent/NL184066C/xx not_active IP Right Cessation
- 1977-03-31 GB GB1374677A patent/GB1575529A/en not_active Expired
Non-Patent Citations (1)
Title |
---|
NICHTS-ERMITTELT |
Also Published As
Publication number | Publication date |
---|---|
NL184066B (nl) | 1988-11-01 |
DE2709280A1 (de) | 1977-10-06 |
FR2357591A1 (fr) | 1978-02-03 |
NL184066C (nl) | 1989-04-03 |
BE853028A (fr) | 1977-09-30 |
FR2357591B1 (US08080257-20111220-C00005.png) | 1981-06-26 |
PL197041A1 (pl) | 1978-01-02 |
DE2709280C2 (de) | 1986-08-21 |
GB1575529A (en) | 1980-09-24 |
NL7703462A (nl) | 1977-10-04 |
DE2760272A1 (US08080257-20111220-C00005.png) | 1985-05-09 |
PL114086B1 (en) | 1981-01-31 |
IT1104560B (it) | 1985-10-21 |
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Legal Events
Date | Code | Title | Description |
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Q172 | Divided out of (supplement): |
Ref country code: DE Ref document number: 2709280 |
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8110 | Request for examination paragraph 44 | ||
8181 | Inventor (new situation) |
Free format text: HEINSOHN, GEORGE EDWARD, NEWARK, DEL., US PRUCKMAYR, GERFRIED, MEDIA, PA., US ROBINSON, IVAN MAXWELL, WILMINGTON, DEL., US GIBERT, WALTER WILSON, HOCKESSIN, DEL., US |
|
8181 | Inventor (new situation) |
Free format text: HEINSOHN, GEORGE EDWARD, NEWARK, DEL., US PRUCKMAYR, GERFRIED, MEDIA, PA., US ROBINSON, IVAN MAXWELL, WILMINGTON, DEL., US GILBERT, WALTER WILSON, HOCKESSIN, DEL., US |
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D2 | Grant after examination | ||
8364 | No opposition during term of opposition |