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Cyclic (poly)glycerol sulphates and preparation and use thereof

A kind of glycerol sulfate, cyclic technology, applied in the intermediate field of surfactant

Inactive Publication Date: 2014-07-09
RHODIA OPERATIONS SAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For cyclic sulfites containing primary hydroxyl groups, there is no one-step method to convert them into the corresponding cyclic sulfates in high yields without affecting these hydroxyl groups

Method used

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  • Cyclic (poly)glycerol sulphates and preparation and use thereof
  • Cyclic (poly)glycerol sulphates and preparation and use thereof
  • Cyclic (poly)glycerol sulphates and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0080] Example 1: Method for preparing the compound of formula (I')

[0081] Add 6.9g of cyclic sulfite (4-(hydroxymethyl)-1,3,2-dioxapentane-2-oxide (50mmol)) and 50mL of acetonitrile to a 250mL three-necked round bottom flask , 100mgRuCl 3 .3H 2 O (0.75mmol) and 16g NaIO 4 (75 mmol), the mixture was cooled to 0-5°C by an ice-salt bath. Then 75 mL of cold water was added to the mixture and the temperature was increased to 30°C. The mixture was stirred for 5 minutes, and the mixture became a green suspension. Combine 400mL ethyl acetate and 40mL saturated NaHCO 3 The aqueous solution is added to the mixture. The mixture was separated into two phases. The aqueous phase was extracted with ethyl acetate (100ml×2). The combined organic phase was washed with 40 mL of water and subjected to anhydrous Na 2 SO 4 dry. The solvent was removed by a rotary evaporator to produce 5.6 g of the desired yellow liquid product, crude yield: 72.7%.

[0082] 1 H NMR(CDCl 3 , 500MHz), δ: 5.05-5....

example 2

[0084] Example 2: Method for preparing cyclic diglycerol sulfate

[0085]

[0086] Add sulfite II (50mmol), 50mL acetonitrile, 100mg RuCl as shown above into a 250mL three-neck round bottom flask 3 .3H 2 O (0.75mmol) and 16g NaIO 4 (75 mmol), the mixture was cooled to 0-5°C by an ice-salt bath. Then 75 mL of cold water was added to the mixture and the temperature was increased to 30°C. The mixture was stirred for 5 mins, and the mixture became a green suspension. Combine 400mL ethyl acetate and 40mL saturated NaHCO 3 The aqueous solution is added to the mixture. The mixture was separated into two phases. The aqueous phase was extracted with ethyl acetate (100ml×2). The combined organic phase was washed with 40 mL of water and subjected to anhydrous Na 2 SO 4 dry. The solvent was removed by a rotary evaporator to produce 6.0 g of the desired yellow liquid product, crude yield: 52.7%.

example 3

[0087] Example 3: Application example

[0088] 7.64g of N,N-dimethyldodecane-1-amine and 25ml of THF were added to a 50ml three-necked round bottom flask, 5.36g of CGS (a compound of formula (I')) (in 10ml of THF) was added dropwise in about 10 minutes, and then heated to reflux using an oil bath and stirred for a period of time. Many bubbles were observed at the bottom of the flask. Then, the reaction mixture was cooled to room temperature and filtered, washed with THF and dried. 7.9 g of the following sulfate betaine was obtained as a white solid.

[0089] HOCH 2 CH(OSO 3 - )CHN + (CH 3 ) 2 (CH 2 ) 11 CH 3

[0090] The final product of the reaction 1 H NMR(DMSO-d 6 )(CDCl 3 , 500MHz), δ: 5.1 (m, 1H); 4.5 (m, 1H); 3.75 (m, 1H); 3.3-3.51 (m, 4H); 3.1 (d, 6H); 1.61-1.69 (m, 2H) ); 1.29 (m, 18H); 0.84 (t, 3H).

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Abstract

The present invention relates to novel cyclic sulphates of (poly)glycerol, particularly to the novel compound of 4-(hydroxymethyl)-1,3,2-dioxathiolane-2,2-dioxide. The present invention also relates to the preparation process of the cyclic sulphate compounds, and to the use thereof as an intermediate to prepare green surfactants containing sulphate groups.

Description

Invention field [0001] The present invention relates to a novel cyclic sulfate of glycerol or polyglycerol with free hydroxyl groups, and more particularly to a novel 4-(hydroxymethyl)-1,3,2-dioxapentane-2, 2-Dioxide compound. The present invention also relates to the preparation method of the novel cyclic sulfate compound, and to its use as an intermediate for the preparation of a sulfate group-containing surfactant. Background of the invention [0002] Most surfactants produced by the chemical industry are based on petrochemical products. Surfactants prepared from petrochemical products by traditional methods contain 1,4-dioxane which may be carcinogenic to humans. Many efforts have been reported to use carbohydrates as bulk raw materials for the synthesis of nonionic surfactants. See Kosaka, T; Yamada T.’s Sucrochemistry ACS Symposium Series, No. 41 Sucrochemistry ACS [Symposium Series ACS Symposium, Issue 41]; John L. Hickson, Ed.; Am. Chem. Soc. [American Chemical Society...

Claims

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Application Information

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IPC IPC(8): C07D327/10C07C305/04C07C303/24
CPCC07D327/10C08G65/48C08G2650/04
Inventor P.梅蒂维耶Y.赵Z.范C.朱
Owner RHODIA OPERATIONS SAS
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