GB813495A - Ethers of polyoxyalkylene glycols - Google Patents
Ethers of polyoxyalkylene glycolsInfo
- Publication number
- GB813495A GB813495A GB3844656A GB3844656A GB813495A GB 813495 A GB813495 A GB 813495A GB 3844656 A GB3844656 A GB 3844656A GB 3844656 A GB3844656 A GB 3844656A GB 813495 A GB813495 A GB 813495A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sodium
- ether
- reaction
- compound
- until
- 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
- 150000002170 ethers Chemical class 0.000 title abstract 3
- 150000002334 glycols Chemical class 0.000 title abstract 3
- -1 ethylene, propylene Chemical group 0.000 abstract 11
- 150000001875 compounds Chemical class 0.000 abstract 9
- 159000000001 potassium salts Chemical class 0.000 abstract 9
- 159000000000 sodium salts Chemical class 0.000 abstract 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 8
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 7
- 229920000647 polyepoxide Polymers 0.000 abstract 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 7
- 229910052708 sodium Inorganic materials 0.000 abstract 7
- 239000011734 sodium Substances 0.000 abstract 7
- 229920001451 Polypropylene glycol Polymers 0.000 abstract 6
- 150000002118 epoxides Chemical class 0.000 abstract 6
- 239000003085 diluting agent Substances 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 abstract 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N Anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N Chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 229940050176 Methyl Chloride Drugs 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000011780 sodium chloride Substances 0.000 abstract 4
- 239000003701 inert diluent Substances 0.000 abstract 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 3
- 229910052700 potassium Inorganic materials 0.000 abstract 3
- 239000011591 potassium Substances 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 2
- 229910000831 Steel Inorganic materials 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001350 alkyl halides Chemical class 0.000 abstract 2
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 abstract 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 2
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 2
- 230000000704 physical effect Effects 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 2
- 239000010959 steel Substances 0.000 abstract 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
Classifications
-
- 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
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
Abstract
Sodium and potassium salts of monoethers of polyoxyalkylene glycols are prepared by adding at least one of the 1 : 2-epoxides of ethylene, propylene, or butylene to a well agitated solution of the sodium or potassium salt of a monohydric phenol or aliphatic alcohol having from 1 to 20 carbon atoms in a relatively inert diluent, the reaction being carried out in substantially moisture-free conditions at 60 DEG to 200 DEG C. until at least 5 mols. of the 1 : 2-epoxy compound have been added for each mol. of the sodium or potassium salt. The monohydroxy compounds may bear alkoxy substituents, and may be a primary, secondary or tertiary alkanol, alkoxy alkanol, phenol, alkoxy phenol or alkyl phenol. The sodium or potassium salt may be prepared in the same reaction vessel prior to the reaction with the epoxy compound by treating the hydroxy compound with at least 0.8 mols. of sodium or potassium under moisture free conditions in the presence of an inert diluent at a temperature between - 10 DEG and 150 DEG C. The diluent may be diisopropyl ether, dioxane, n-hexane, cyclohexane, benzene or toluene. The reaction may be carried out at slightly elevated pressure, e.g. up to 10 atmospheres. The product may be neutralized, e.g. with anhydrous or aqueous hydrogen chloride, to give the mono-ether of the polyoxyalkylene glycol which may be worked up by extraction and distillation or the product may be treated with an alkyl halide such as methyl chloride, preferably at 60 DEG to 160 DEG C. to give a di-ether of the polyoxyalkylene glycol. In the examples sodium is reacted with the monohydroxy compound in a steel vessel in the presence of toluene at about 120 DEG C. and 3-4 atmos. pressure, the hydrogen evolved is vented off, and the epoxide is added at about 140 DEG C. and 3-7 atmos. pressure until the desired chain length is obtained. When a diether is desired the salt of the monoether is heated with sodium until no more hydrogen is evolved and then treated with an excess of gaseous methyl chloride at 100 DEG to 110 DEG C. and 4-7 atmos. The examples describe the preparation of (3) polyoxypropylene glycol n-butyl methyl ether; (7) polyoxypropylene glycol phenyl methyl ether; (8) polyoxybutylene glycol sec.-butyl methyl ether and (1), (2), (4), (5), (6), (9) polyoxypropylene glycol sec.-butyl methyl ether where (1), (2) various ratios of epoxide to sec.-butanol are used, (4), (5) a comparison is given with ethers not prepared in accordance with the invention, and (6) various diluents are used. Some physical properties of these polymeric diethers are given.ALSO:Sodium and potassium salts of monoethers of polyoxyalkylene glycols are prepared by reacting at least one of the 1 : 2 epoxides of ethylene, propylene or butylene with the sodium or potassium salt of a monohydric phenol or aliphatic alcohol having from 1 to 20 carbon atoms and containing only carbon, hydrogen and oxygen in the molecule with no other functional group other than the one hydroxy group, the reaction being carried out in substantially moisture-free conditions in the temperature range of 60 DEG to 200 DEG C. by adding the 1 : 2 epoxy compound to a well-agitated solution of the sodium or potassium salt of the monohydroxy compound in a diluent which is relatively inert both to the sodium or potassium and the 1 : 2 epoxy compound, until at least 5 mols. of the 1 : 2 epoxy compound have been added for each mol. of the sodium or potassium salt of the monohydroxy compound. The monohydroxy compounds used may bear alkoxy substituents and compounds such as primary, secondary and tertiary alkanols and alkoxy alkanols and phenol, alkoxy phenols and alkyl phenols may be used. The sodium or potassium salt may be prepared in the same reaction vessel prior to the reaction with the epoxy compound by treating the hydroxy compound with at least 0.8 mol., preferably about 1 mol., of sodium or potassium under moisture-free conditions in the presence of an inert diluent at a temperature between - 10 DEG and 150 DEG C. The diluent may be a compound such as di-isopropyl ether, dioxane, n-hexane, cyclohexane, benzene or toluene. The 1 : 2 epoxy compound is added to a solution of the salt of the monohydroxy compound which is preferably heated to a temperature between 110 DEG and 140 DEG C. until at least 5 mols. of epoxide have been added. The reaction may be carried out at slightly elevated pressure, e.g. up to 10 atmospheres, to contain the reactants. The reaction product, which contains the salt of the polyoxyalkylene glycol mono-ether may be neutralized, e.g. with anhydrous or aqueous hydrogen chloride, to give the mono-ether of the polyoxyalkylene glycol which may be worked up by extraction and distillation or the reaction product may be treated with an alkyl halide such as methyl chloride, preferably at a temperature between 60 DEG and 160 DEG C. to give a di-ether of the polyoxyalkylene glycol. In the examples sodium is reacted with the monohydroxy compound in a steel vessel in the presence of toluene at about 120 DEG C. and 3-4 atmos. pressure, the hydrogen evolved is vented off, and the epoxide is added at about 140 DEG C. and 5-7 atmos. pressure until the desired chain length is obtained, when a diether product is desired the salt of the monoether is heated with sodium until no more hydrogen is evolved and then treated with an excess of gaseous methyl chloride at 100 DEG to 110 DEG C. and 4-7 atmos. until reaction is complete. The examples describe the preparation of (3) polyoxypropylene glycol n-butyl methyl ether; (7) polyoxypropylene glycol phenyl methyl ether; (8) polyoxybutylene glycol sec.-butyl methyl ether and (1), (2), (4), (5), (6), (9), polyoxypropylene glycol sec.-butyl methyl ether where (1), (2) various ratios of epoxide to sec.-butanol are used, (4), (5) a comparison is given with ethers not prepared in accordance with the invention and (6) various diluents are used. Some physical properties of these polymeric diethers are given.
Publications (1)
Publication Number | Publication Date |
---|---|
GB813495A true GB813495A (en) | 1959-05-21 |
Family
ID=1745266
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3844656A Expired GB813495A (en) | 1956-12-17 | Ethers of polyoxyalkylene glycols |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB813495A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1192213B (en) * | 1959-12-15 | 1965-05-06 | Rohm & Haas | Process for the production of polyglycol ethers from dialkylphenols and ethylene oxide |
DE1231835B (en) * | 1960-06-23 | 1967-01-05 | Union Carbide Corp | Brake fluid |
-
1956
- 1956-12-17 GB GB3844656A patent/GB813495A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1192213B (en) * | 1959-12-15 | 1965-05-06 | Rohm & Haas | Process for the production of polyglycol ethers from dialkylphenols and ethylene oxide |
DE1231835B (en) * | 1960-06-23 | 1967-01-05 | Union Carbide Corp | Brake fluid |
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