GB709478A - Polyethylene glycol derivatives and a process of making the same - Google Patents
Polyethylene glycol derivatives and a process of making the sameInfo
- Publication number
- GB709478A GB709478A GB3470/51A GB347051A GB709478A GB 709478 A GB709478 A GB 709478A GB 3470/51 A GB3470/51 A GB 3470/51A GB 347051 A GB347051 A GB 347051A GB 709478 A GB709478 A GB 709478A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polyethylene glycol
- benzene
- phenyl
- ether
- sulphonyl chloride
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the formula RO(CH2CH2O)nCH2CH2O . SO2R1 wherein R and R1 are hydrocarbon radicals and n is an integer from 4 to 20. Such compounds are obtained by reacting a compound of the formula RO(CH2CH2O)nCH2CH2OH with an agent capable of replacing the -OH group by the group -O.SO2R1, e.g with a sulphonyl chloride or bromide R1SO,Cl or R1SO2Br.R1 may represent a methyl, ethyl, phenyl or tolyl radical and R may represent a methyl, ethyl, propyl, 2-ethylbutyl, 2-heptyl, diisobutylmethyl, phenyl, tolyl, a - or b - naphthyl, cyclohexyl, cyclopentyl, benzyl, benzhydryl, o - phenylnamyl, fluorenyl, lauryl or cetyl radical. Reaction may be effected in the presence of pyridine or inorganic acid-binding agents. In examples (1) polyethylene glycol methyl ether (M.Wt. 350, and the average value of n being about 6) is reacted with benzene sulphonyl chloride whilst keeping the mixture alkaline, to give the corresponding benzene sulphonic acid ester. The product is purified by partition between chloroform and water and then between a mixture of benzene and ether and water. In the process of this example polyethylene glycol methyl ethers of molecular weight 550 and 750 respectively or polyethylene glycol monoethyl, butyl, propyl, phenyl, or cresyl derivatives may also be used; the benzene sulphonic acid ester of polyethylene glycol b -naphthyl ether is prepared similarly to (1). Unused benzene sulphonyl chloride is removed by adding ammonia to a two-phase mixture of the product in chloroform, and water and separating the benzene sulphonamide produced. In the same manner polyethylene glycol moncyclohexyl, cyclopentyl or benzyl ethyl ether may be reacted. Similarly the polyethylene glycol derivative of formula C6H5(CH2)4 CH2O(CH2CH2O)4CH2CH2OH(from o - phenyl-namyl alcohol reacted with 5 moles of ethylene oxide) may be converted to the benzene sulphonic acid ester. In an analagous manner polyethylene glycol monolauryl or cetyl ether may be reacted with benzene sulphonyl chloride or other sulphonic acid halides, e.g. methane sulphonic acid bromide, ethane sulphonic acid chloride or p-toluene sulphonyl chloride.ALSO:The invention comprises compounds of the formula <FORM:0709478/IV (b)/1> , wherein R and R1 are hydrocarbon radicals and n is an integer from 4 to 20. Such compounds are obtained by reacting a compound of the formula RO(CH2CH2O)nCH2CH2OH with an agent capable of replacing the OH group by the group O.SO2R1, e.g. with a sulphonyl chloride or bromide R1SO2Cl or R1SO2Br.R1 may represent a methyl, ethyl, phenyl or tolyl radical and R may represent a methyl, ethyl, propyl, 2-ethyl-butyl, 2-heptyl, diisobutyl-methyl, phenyl, tolyl, a - or b -naphthyl, cyclohexyl, cyclopentyl, benzyl, benzhydryl, o -phenyl-n-amyl, fluorenyl, lauryl or cetyl radical. Reaction may be effected in the presence of pyridine or inorganic acid-binding agents. In examples: (1) polyethylene glycol methyl ether (M.wt. 350, and the average value of n being about 6) is reacted with benzene sulphonyl chloride while keeping the mixture alkaline, to give the corresponding benzene sulphonic acid ester. The product is purified by partition between chloroform and water and then between a mixture of benzene and ether and water. In the process of this example, polyethylene glycol monomethyl ethers of molecular weight 550 and 750, respectively, may also be used, or polyethylene glycol mono-ethyl, butyl, propyl, phenyl or cresyl derivatives; (2) the benzene sulphonic acid ester of polyethylene glycol b -naphthyl ether is prepared similarly to (1). Unused benzene sulphonyl chloride is removed by adding ammonia to a two-phase mixture of the product in water and separating the benzene sulphonamide produced. In the same manner polyethylene glycol monocyclohexyl, cyclopentyl or benzyl ether may be reacted. Similarly the polyethylene glycol derivative of formula C6H5(CH2)4CH2O . (CH2CH2O)4 . CH2CH2OH (from o -phenyl-n-amyl alcohol reacted with 5 mols. of ethylene oxide) may be converted to the benzene sulphonic ester. In an analogous manner polyethylene glycol mono-lauryl or cetyl ether may be reacted with benzene sulphochloride, or other sulphonic acid halides, e.g. methane sulphonyl bromide, ethane sulphonyl chloride or p-toluene sulphonyl chloride.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH709478X | 1950-02-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB709478A true GB709478A (en) | 1954-05-26 |
Family
ID=4530651
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3470/51A Expired GB709478A (en) | 1950-02-15 | 1951-02-13 | Polyethylene glycol derivatives and a process of making the same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB709478A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3240700A (en) * | 1962-04-25 | 1966-03-15 | Phillips Petroleum Co | Process of drilling a well |
CN106631924A (en) * | 2016-12-19 | 2017-05-10 | 聊城大学 | Laurinol polyoxyethylene ether benzene sulfonate, preparation method and application |
WO2023201805A1 (en) * | 2022-04-22 | 2023-10-26 | 天津凯莱英制药有限公司 | Method for preparing polyethylene glycol-glycerol derivative and intermediate thereof |
-
1951
- 1951-02-13 GB GB3470/51A patent/GB709478A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3240700A (en) * | 1962-04-25 | 1966-03-15 | Phillips Petroleum Co | Process of drilling a well |
CN106631924A (en) * | 2016-12-19 | 2017-05-10 | 聊城大学 | Laurinol polyoxyethylene ether benzene sulfonate, preparation method and application |
WO2023201805A1 (en) * | 2022-04-22 | 2023-10-26 | 天津凯莱英制药有限公司 | Method for preparing polyethylene glycol-glycerol derivative and intermediate thereof |
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