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US4217296A Expired / Lapsed US ⏱️ 0.0 years remaining

Alkyl glyceryl ether sulfate salts and process for their preparation

Assignee: FMC Corp
•
Filing: 1978-11-13
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Granted: 1980-08-12
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Expires: 1998-11-13
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Abstract

Abstract Novel sulfate salts of C10-C20 linear alkyl glyceryl ether alcohols, useful as biodegradable surfactants in detergent compositions, are prepared by reacting a stoichiometric excess of C10-C20 linear alkyl alcohol with glycidol predissolved in hexyl acetate, to selectively produce C10-C20 linear alkyl glyceryl ether alcohols containing 1-3 glyceryl units, sulfating said ether alcohols, and neutralizing the sulfates with base.

Inventors

  • 👤 Sidney Berkowitz

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 22:33
CPC Classifications
C; C07; C07C; C07C305/00; C07C41/00; C07C41/01; C07C41/02; C07C41/03; C11; C11D; C11D1/00; C11D1/02; C11D1/12; C11D1/16; Y; Y10; Y10S; Y10S516/00; Y10S516/01; Y10S516/03; Y10S516/905; Y10S516/909

Claims Analysis

Total Claims: 25
Claim 1
Independent Claim 122 words
A process for preparing a mixture of linear alkyl glyceryl ether alcohols containing 1 to 3 glyceryl units which comprises the steps of bringing together and reacting, a C 10 -C 20 linear alkyl alcohol and glycidol which is predissolved in hexyl acetate, in the presence of an acid catalyst in a reaction zone, said alcohol and glycidol being brought together and reacted in a molecular ratio within the range of from about 1.5:1 to about 8:1; maintaining the resulting reaction mass in an agitated condition; maintaining the temperature of the reaction mass within the range of from about 25° to about 125° C. during the reaction period; and recovering said mixture of linear alkyl glyceryl ether alcohols from the reaction mass.
Claim 2
Dependent Claim 122 words
A process for preparing a mixture of linear alkyl glyceryl ether alcohols containing 1 to 3 glyceryl units which comprises the steps of bringing together and reacting, a C 10 -C 20 linear alkyl alcohol and glycidol which is predissolved in hexyl acetate, in the presence of an acid catalyst in a reaction zone, said alcohol and glycidol being brought together and reacted in a molecular ratio within the range of from about 1.5:1 to about 8:1; maintaining the resulting reaction mass in an agitated condition; maintaining the temperature of the reaction mass within the range of from about 25° to about 125° C. during the reaction period; and recovering said mixture of linear alkyl glyceryl ether alcohols from the reaction mass.
Claim 3
Dependent Claim 20 words
The process of claim 1 wherein the linear alkyl alcohol reactant is a C 12 -C 16 linear alkyl alcohol.
Claim 4
Dependent Claim 14 words
The process of claim 1 wherein the linear alkyl alcohol reactant is lauryl alcohol.
Claim 5
Dependent Claim 31 words
The process of claim 1 wherein the linear alkyl alcohol and glycidol are brought together and reacted in a molecular ratio within the range of from about 2:1 to about 4:1.
Claim 6
Dependent Claim 25 words
The process of claim 1 wherein the temperature of the reaction mass is maintained within the range of from about 60° to about 95° C.
Claim 7
Dependent Claim 22 words
The process of claim 1 wherein the reaction of the linear alkyl alcohol and glycidol is carried out in an inert atmosphere.
Claim 8
Dependent Claim 18 words
The process of claim 1 wherein the hexyl acetate solution of glycidol is a 2-30 weight % solution.
Claim 9
Dependent Claim 230 words
A process for preparing a mixture of linear alkyl glyceryl ether sulfate salts containing 1 to 3 glyceryl units which comprises the steps of bringing together and reacting, a C 10 -C 20 linear alkyl alcohol and glycidol wich is predissolved in hexyl acetate, in the presence of an acid catalyst in a reaction zone, said alcohol and glycidol being brought together and reacted in a molecular ratio within the range of from about 1.5:1 to about 8:1; maintaining the resulting reaction mass in an agitated condition; maintaining the temperature of the reaction mass within the range of from about 25° to about 125° C. during the reaction period, recovering a mixture of linear alkyl glyceryl ether alcohols containing 1 to 3 glyceryl units from the reaction mass, contacting and reacting said mixture of ether alcohols with a sulfating agent, said ether alcohols and sulfating agent being contacted and reacted in a molecular ratio within the range of from about 1:1 to about 1:1.15; maintaining the resulting sulfation reaction mass in an agitated condition; maintaining the temperature of the sulfation reaction mass within the range of from about -15° to about 75° C. during the reaction period; recovering a mixture of linear alkyl glyceryl ether sulfates, neutralizing said mixture of sulfates with base and recovering a mixture of linear alkyl glyceryl ether sulfate salts containing 1 to 3 glyceryl units.
Claim 10
Dependent Claim 230 words
A process for preparing a mixture of linear alkyl glyceryl ether sulfate salts containing 1 to 3 glyceryl units which comprises the steps of bringing together and reacting, a C 10 -C 20 linear alkyl alcohol and glycidol wich is predissolved in hexyl acetate, in the presence of an acid catalyst in a reaction zone, said alcohol and glycidol being brought together and reacted in a molecular ratio within the range of from about 1.5:1 to about 8:1; maintaining the resulting reaction mass in an agitated condition; maintaining the temperature of the reaction mass within the range of from about 25° to about 125° C. during the reaction period, recovering a mixture of linear alkyl glyceryl ether alcohols containing 1 to 3 glyceryl units from the reaction mass, contacting and reacting said mixture of ether alcohols with a sulfating agent, said ether alcohols and sulfating agent being contacted and reacted in a molecular ratio within the range of from about 1:1 to about 1:1.15; maintaining the resulting sulfation reaction mass in an agitated condition; maintaining the temperature of the sulfation reaction mass within the range of from about -15° to about 75° C. during the reaction period; recovering a mixture of linear alkyl glyceryl ether sulfates, neutralizing said mixture of sulfates with base and recovering a mixture of linear alkyl glyceryl ether sulfate salts containing 1 to 3 glyceryl units.
Claim 11
Dependent Claim 20 words
The process of claim 8 wherein the linear alkyl alcohol reactant is a C 12 -C 16 linear alkyl alcohol.
Claim 12
Dependent Claim 14 words
The process of claim 8 wherein the linear alkyl alcohol reactant is lauryl alcohol.
Claim 13
Dependent Claim 31 words
The process of claim 8 wherein the linear alkyl alcohol and glycidol are brought together and reacted in a molecular ratio within the range of from about 2:1 to about 4:1.
Claim 14
Dependent Claim 31 words
The process of claim 8 wherein the linear alkyl alcohol and glycidol reaction mass is maintained at a temperature of from about 60° to about 95° C. during the reaction period.
Claim 15
Dependent Claim 22 words
The process of claim 8 wherein the reaction between the linear alkyl alcohol and glycidol is carried out under an inert atmosphere.
Claim 16
Dependent Claim 18 words
The process of claim 8 wherein the hexyl acetate solution of glycidol is a 2-30 weight % solution.
Claim 17
Dependent Claim 12 words
The process of claim 8 wherein the sulfating agent is chlorosulfonic acid.
Claim 18
Dependent Claim 30 words
The process of claim 15 wherein the ether alcohols and sulfating agent are contacted and reacted in a molecular ratio within the range of from about 1:1.01 to about 1:1.05.
Claim 19
Dependent Claim 26 words
The process of claim 15 wherein the sulfation reaction mass is maintained at a temperature within the range of from about 30° to about 40° C.
Claim 20
Dependent Claim 12 words
The process of claim 8 wherein the sulfating agent is sulfur trioxide.
Claim 21
Dependent Claim 34 words
The process of claim 18 wherein the sulfur trioxide is admixed with a diluent selected from the group consisting of nitrogen, air and sulfur dioxide, prior to being contacted with the ether alcohol reactant.
Claim 22
Dependent Claim 30 words
The process of claim 18 wherein the ether alcohols and sulfating agent are contacted and reacted in a molecular ratio within the range of from about 1:1.01 to about 1:1.05.
Claim 23
Dependent Claim 26 words
The process of claim 18 wherein the sulfation reaction mass is maintained at a temperature within the range of from about -10° to about 20° C.
Claim 24
Dependent Claim 24 words
The process of claim 8 wherein the ether alcohol is predissolved in a diluent prior to being contacted and reacted with the sulfating agent.
Claim 25
Dependent Claim 11 words
The process of claim 22 wherein the diluent is methylene chloride.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-08-12 1984-02-11 1984-08-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-08-12 1988-02-11 1988-08-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-08-12 1992-02-11 1992-08-12 $7700.00 Window Closed / Lapsed

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