GB757294A - A process for the manufacture of ethylene-glycol ethers of tetrahydrofurfuryl alcohol and compositions containing same - Google Patents
A process for the manufacture of ethylene-glycol ethers of tetrahydrofurfuryl alcohol and compositions containing sameInfo
- Publication number
- GB757294A GB757294A GB37144/54A GB3714454A GB757294A GB 757294 A GB757294 A GB 757294A GB 37144/54 A GB37144/54 A GB 37144/54A GB 3714454 A GB3714454 A GB 3714454A GB 757294 A GB757294 A GB 757294A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- ethylene oxide
- ethers
- tetrahydrofurfuryl alcohol
- molar proportion
- 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
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Ethers of the general formula <FORM:0757294/IV(a)/1> wherein n is 1, 2, 3 or 4 are prepared by heating tetrahydrofurfuryl alcohol with ethylene oxide in a molar proportion of from 1:1 to 1:4 in the presence of an alkali-metal hydroxide. A preferred hydroxide is sodium hydroxide and this is preferably used in an amount equal to 0.1 to 0.5 per cent by weight of that of the alcohol. The reaction is advantageously conducted at a temperature between 80 DEG and 140 DEG C. in an inert atmosphere, and in a preferred mode of procedure ethylene oxide and nitrogen are introduced into the tetrahydrofurfuryl alcohol and any unreacted ethylene oxide is condensed and reintroduced into the reaction cycle. The reaction product is advantageously isolated by first neutralizing the alkali-metal hydroxide with a non-volatile mineral acid such as phosphoric acid, separating the difficultly-soluble salt so formed and fractionating the crude product remaining. If a small excess of phosphoric acid is used the excess acid may be precipitated by means of barium or calcium carbonate. In examples: (1) tetrahydrofurfuryl alcohol and ethylene oxide in a molar proportion of 1:3 give a mixture of mono-, di- and tri-ethylene glycol ethers of the above general formula; (2) the mono-ether is prepared using a 1:1 molar proportion; (3) the di-ether is prepared using a 1:2 molar proportion. The products are stated to be useful as solvents for pharmaceuticals.ALSO:A pharmaceutical composition contains as a solvent one or more tetrahydrofurfuryl ethers of the general formula; <FORM:0757294/VI/1> wherein n is 1, 2, 3 or 4. A specified active ingredient for such a composition is a mixture of acetyl-choline and pyridyl-3-carbinol, and another drug mixture referred to which may be brought into solution in a similar way is a mixture of the dimethyl-carbanic acid ester of 1-methyl-3-hydroxy-pyridinium bromide with acetyl choline and/or pyridyl-3-carbinol. The ethers are stated to be miscible with water in any proportions and to be good solvents for drugs such as acetylsalicylic acid, ethyl phenyl barbituric acid, alkyl isopropyl barbituric acid, p-amino-salicylic acid and neohesperidin.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH757294X | 1953-12-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB757294A true GB757294A (en) | 1956-09-19 |
Family
ID=4534381
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB37144/54A Expired GB757294A (en) | 1953-12-29 | 1954-12-23 | A process for the manufacture of ethylene-glycol ethers of tetrahydrofurfuryl alcohol and compositions containing same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB757294A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3025307A (en) * | 1958-09-10 | 1962-03-13 | Merck & Co Inc | 2, 5-bis (2, 3-epoxypropoxymethyl)-tetrahydrofuran |
US3073848A (en) * | 1958-10-14 | 1963-01-15 | Wasson Burton Kendall | Tetrahydrofurfuryl carbamates |
US4385173A (en) | 1980-04-21 | 1983-05-24 | Shell Oil Company | Polyol polyether preparation process |
WO2011103142A1 (en) * | 2010-02-16 | 2011-08-25 | Fluidic, Inc. | Electrochemical cell, and particularly a cell with electro deposited |
CN113896698A (en) * | 2020-06-22 | 2022-01-07 | 中国石油化工股份有限公司 | Synthesis method of tetrahydrofurfuryl alcohol ethyl ether |
-
1954
- 1954-12-23 GB GB37144/54A patent/GB757294A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3025307A (en) * | 1958-09-10 | 1962-03-13 | Merck & Co Inc | 2, 5-bis (2, 3-epoxypropoxymethyl)-tetrahydrofuran |
US3073848A (en) * | 1958-10-14 | 1963-01-15 | Wasson Burton Kendall | Tetrahydrofurfuryl carbamates |
US4385173A (en) | 1980-04-21 | 1983-05-24 | Shell Oil Company | Polyol polyether preparation process |
WO2011103142A1 (en) * | 2010-02-16 | 2011-08-25 | Fluidic, Inc. | Electrochemical cell, and particularly a cell with electro deposited |
US8877391B2 (en) | 2010-02-16 | 2014-11-04 | Fluidic, Inc. | Electrochemical cell, and particularly a cell with electrodeposited fuel |
CN113896698A (en) * | 2020-06-22 | 2022-01-07 | 中国石油化工股份有限公司 | Synthesis method of tetrahydrofurfuryl alcohol ethyl ether |
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