US4091014A
Expired / Lapsed
US
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Process for making ether sulfonates
Assignee: Huntsman Corp
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Filing: 1976-12-01
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Granted: 1978-05-23
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Expires: 1996-12-01
Abstract
Abstract Covers a method of sulfonating organic alcohols to prepare ether sulfonates thereof by reacting said organic alcohol compound with a hydroxy-containing alkyl sulfonic salt thereof under carefully controlled conditions comprising use of a vacuum less than about 300 mm of mercury, while for at least the majority of the reaction period dispersing through the liquid reaction mass an inert gas.
Inventors
- 👤 Fred L. Johnson, Jr.
- 👤 John A. Patterson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 09:26
CPC Classifications
C; C07; C07C; C07C309/00
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
160 words
A method of preparing ether sulfonates of the formula: R--O--R.sub.3 --SO.sub.3 A where R is a radical selected from the group consisting of C 2 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 hydroxyalkyl, C 2 -C 22 hydroxyalkenyl, alkaryl containing 1 or more C 1 -C 18 alkyl groups substituted on said aryl group, aralkyl containing 7-28 carbon atoms, and polyalkyleneether derivatives of any of the foregoing, R 3 is alkylene, and A is an alkali metal cation which comprises the step of reacting in the presence of a base and in the liquid phase an alcohol having a molecular weight greater than 200 and having the formula, ROH where R has the just stated significance, with an alkali metal hydroxy-containing alkyl sulfonic acid salt under a vacuum less than about 300 mm of mercury while for at least the majority of said reaction period continuously dispersing an inert gas through said liquid reaction mass.
Claim 2
Independent Claim
160 words
A method of preparing ether sulfonates of the formula: R--O--R.sub.3 --SO.sub.3 A where R is a radical selected from the group consisting of C 2 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 hydroxyalkyl, C 2 -C 22 hydroxyalkenyl, alkaryl containing 1 or more C 1 -C 18 alkyl groups substituted on said aryl group, aralkyl containing 7-28 carbon atoms, and polyalkyleneether derivatives of any of the foregoing, R 3 is alkylene, and A is an alkali metal cation which comprises the step of reacting in the presence of a base and in the liquid phase an alcohol having a molecular weight greater than 200 and having the formula, ROH where R has the just stated significance, with an alkali metal hydroxy-containing alkyl sulfonic acid salt under a vacuum less than about 300 mm of mercury while for at least the majority of said reaction period continuously dispersing an inert gas through said liquid reaction mass.
Claim 3
Dependent Claim
19 words
The method of claim 1 wherein said sulfonic acid salt reactant is the sodium salt of 2-hydroxyethane sulfonic acid.
Claim 4
Dependent Claim
20 words
The method of claim 1 wherein said reaction is run under a vacuum less than about 100 mm of mercury.
Claim 5
Dependent Claim
11 words
The method of claim 3 wherein said vacuum is 2-100 mm.
Claim 6
Dependent Claim
11 words
The method of claim 1 wherein said inert gas is nitrogen.
Claim 7
Dependent Claim
46 words
The method of claim 1 wherein said alcohol ROH is reacted with a sulfonic acid salt by slowly adding an aqueous solution of said salt to said alcohol at a rate less than that sufficient to agglomerate finely divided particles of said salt during said reaction.
Claim 8
Dependent Claim
24 words
The method of claim 1 wherein said reaction is carried out at a temperature less than the melting point of said sulfonic acid salt.
Claim 9
Dependent Claim
21 words
The method of claim 1 wherein said reaction is terminated near the point of maximum conversion by cooling the reaction mass.
Claim 10
Dependent Claim
15 words
The method of claim 7 wherein said temperature of reaction is greater than 180° C.
Claim 11
Dependent Claim
12 words
The method of claim 1 where R 3 is ethylene or propylene.
Claim 12
Independent Claim
147 words
The method of preparing ether sulfonates of the formula: ##STR11## where R is a C 1 -C 22 alkyl group, n is an integer of 1-3, R 1 is H or CH 3 , z is an integer of 1-40, R 3 is ethylene or propylene and A is an alkali metal cation, which comprises the step of reacting in the presence of a base and in the liquid phase an alcohol compound having the formula ##STR12## where R, R 1 , n and z have a significance as above stated with a hydroxy-containing alkali metal alkyl sulfonic acid salt having the formula OHR.sub.3 SO.sub.3 A where R 3 and A have the significance as above stated under a vacuum less than about 300 mm of mercury, while for at least the majority of said reaction period continuously dispersing an inert gas through said liquid reaction mass.
Claim 13
Independent Claim
147 words
The method of preparing ether sulfonates of the formula: ##STR11## where R is a C 1 -C 22 alkyl group, n is an integer of 1-3, R 1 is H or CH 3 , z is an integer of 1-40, R 3 is ethylene or propylene and A is an alkali metal cation, which comprises the step of reacting in the presence of a base and in the liquid phase an alcohol compound having the formula ##STR12## where R, R 1 , n and z have a significance as above stated with a hydroxy-containing alkali metal alkyl sulfonic acid salt having the formula OHR.sub.3 SO.sub.3 A where R 3 and A have the significance as above stated under a vacuum less than about 300 mm of mercury, while for at least the majority of said reaction period continuously dispersing an inert gas through said liquid reaction mass.
Claim 14
Dependent Claim
18 words
The method of claim 11 wherein said sulfonic acid salt is the sodium salt of 2-hydroxyethane sulfonic acid.
Claim 15
Dependent Claim
14 words
The method of claim 11 wherein said vacuum is less than about 100 mm.
Claim 16
Dependent Claim
11 words
The method of claim 13 wherein said vacuum is 2-100 mm.
Claim 17
Dependent Claim
11 words
The method of claim 11 wherein said inert gas is nitrogen.
Claim 18
Dependent Claim
45 words
The method of claim 11 wherein said alcohol is reacted with a sulfonic acid salt by slowly adding an aqueous solution of said salt to said alcohol at a rate less than that sufficient to agglomerate finely divided particles of said salt during said reaction.
Claim 19
Dependent Claim
24 words
The method of claim 11 wherein said reaction is carried out at a temperature less than the melting point of said sulfonic acid salt.
Claim 20
Dependent Claim
21 words
The method of claim 11 wherein said reaction is terminated near the point of maximum conversion by cooling said reaction mass.
Claim 21
Dependent Claim
16 words
The method of claim 11 wherein said temperature of reaction is greater than about 180° C.
Claim 22
Dependent Claim
10 words
The method of claim 11 wherein R 3 is ethylene.
Claim 23
Dependent Claim
19 words
The method of claim 20 wherein said reaction is carried out at a temperature range of about 180°-190° C.
Claim 24
Dependent Claim
19 words
The method of claim 11 wherein R is a C 6 -C 20 alkyl group, and n is 1.
Claim 25
Dependent Claim
13 words
The method of claim 22 wherein R is C 8 -C 12 .
Claim 26
Dependent Claim
9 words
The method of claim 11 wherein z is 1-10.
Claim 27
Dependent Claim
9 words
The method of claim 24 where z is 2-6.
Claim 28
Dependent Claim
11 words
The method of claim 11 wherein said base is potassium hydroxide.
Claim 29
Dependent Claim
22 words
The method of claim 11 wherein said base catalyzed reaction is carried out by first forming the alkoxide of said alcohol reactant.
Claim 30
Dependent Claim
17 words
The method of claim 11 wherein a molar excess of said alcohol is present during said reaction.
Claim 31
Dependent Claim
18 words
The method of claim 28 wherein 1.2-2.5 mols of said alcohol are reacted per mole sulfonic acid salt.
Claim 32
Dependent Claim
19 words
The method of claim 29 wherein 1.5-2:1 mols of said alcohol are reacted per mole of sulfonic acid salt
Claim 33
Dependent Claim
26 words
The method of claim 11 wherein unreacted alcohol is separated from said ether sulfonates by solvent extraction with a mixture of water and an organic ester.
Claim 34
Dependent Claim
12 words
The method of claim 31 wherein said organic ester is ethyl acetate.
Claim 35
Dependent Claim
29 words
The method of claim 11 wherein said ether sulfonate is separated from unreacted alcohol by solvent extraction with a mixture of water, an organic ketone and an organic hydrocarbon.
Claim 36
Dependent Claim
13 words
The method of claim 33 wherein said mixture comprises benzene, acetone and water.
References Cited (Backward Citations)
US2535678A
Cited
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