# US 5,349,101 A · Process for the preparation of secondary alkyl sulfate-containing surfactant compositions

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- Number: US 5,349,101 A
- Document ID: US5349101A
- Status: Granted
- Kind: A
- Application number: 07/994,022
- Filed: 1992-12-21
- Granted: 1994-09-20
- Earliest claimed: 1992-05-28
- Assignees: Shell Oil Company
- Inventors: Eugene F. Lutz; David K. Schisla; Robert S. Tomaskovic; Timothy D. Hoewing
- Web page: https://patentgrep.com/patent/US5349101A

## CPC

- C07C 303/44: Separation; Purification
- C07C 303/24: of esters of sulfuric acids
- C11D 1/146: {Sulfuric acid esters}
- Y10S 516/03: Organic sulfoxy compound containing
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

This invention relates to solid secondary alkyl sulfate-containing surface active compositions which are formed by crystallization and which contain at least about 80 percent by weight of secondary alkyl sulfate. These compositions are substantially free of unreacted organic matter and water. The invention further relates to a process for preparing these solid secondary alkyl sulfate-containing compositions.

## Claims

### Claim 1

A process for preparing a solid secondary alkyl sulfate-containing surface active composition which comprises:
a) preparing a detergent range alkyl sulfuric acid-containing solution,
b) contacting said detergent range alkyl sulfuric acid-containing solution with a base in aqueous solution,
c) heating the product of step b) to saponify dialkyl sulfate and to remove substantially all of the water from the mixture,
d) cooling the product of step c) in the presence of a nonionic organic liquid diluent to crystallize a solid secondary alkyl sulfate-containing surface active composition from the mixture, and
e) recovering and drying the crystallized solid secondary alkyl sulfate-containing surface active composition.

### Claim 2 (depends on 1)

The process of claim 1 wherein said detergent range alkyl sulfuric acid-containing solution is prepared by sulfating a reactant selected from the group consisting of detergent range olefins, detergent range alcohols and mixtures thereof, with a sulfating agent.

### Claim 3 (depends on 1)

The process of claim 1 wherein the nonionic organic liquid diluent is selected from the group consisting of aliphatic hydrocarbons, aromatic hydrocarbons and mixtures thereof.

### Claim 4 (depends on 3)

The process of claim 3 wherein the nonionic organic liquid diluent in step c) is selected from the group consisting of heptane, toluene, isooctane, nonane, and mixtures thereof.

### Claim 5 (depends on 1)

The process of claim 1 wherein the base in step b) is selected from ammonium, alkali metal or alkaline earth metal hydroxides, carbonates or bicarbonates.

### Claim 6 (depends on 5)

The process of claim 5 wherein said base is selected from the group consisting of sodium hydroxide, potassium hydroxide and mixtures thereof.

### Claim 7 (depends on 1)

The process of claim 1 wherein said base in aqueous solution comprises from about 10 percent by weight to about 85 percent by weight of base in water.

### Claim 8 (depends on 7)

The process of claim 7 wherein said base in aqueous solution comprises from about 20 percent by weight to about 50 percent by weight of base in water.

### Claim 9 (depends on 1)

The process of claim 1 wherein said solid secondary alkyl sulfate-containing surface active composition recovered in step e) contains from about 80 percent by weight to about 99 percent by weight secondary alkyl sulfate.

### Claim 10 (depends on 9)

The process of claim 9 wherein said solid secondary alkyl sulfate-containing surface active composition recovered in step e) contains from about 88 percent by weight to about 99 percent by weight secondary alkyl sulfate.

### Claim 11 (depends on 1)

The process of claim 1 wherein prior to drying, the crystallized solid secondary alkyl sulfate-containing surface active composition is washed with chilled water.

### Claim 12 (depends on 1)

The process of claim 1 wherein following drying, the crystallized solid secondary alkyl sulfate-containing surface active composition is washed with chilled water.

### Claim 13

A process for preparing secondary alkyl sulfate-containing surface active compositions substantially free of unreacted organic matter and water, which process comprises:
a) sulfating a reactant selected from the group consisting of detergent range olefins, detergent range alcohols and mixtures thereof,
b) neutralizing the sulfation product of step a) with a base in aqueous solution,
c) saponifying the product of step b),
d) crystallizing the product of step c), and
e) recovering and drying the secondary alkyl sulfate-containing product from the product of step d), wherein a nonionic organic liquid diluent is added prior to step d).

### Claim 14 (depends on 13)

The process of claim 13 wherein said reactant is a detergent range olefin having from about 12 to about 18 carbon atoms.

### Claim 15 (depends on 13)

The process of claim 13 wherein said sulfating step is carried out using concentrated sulfuric acid having a concentration of from about 75 percent by weight to about 100 percent by weight in water.

### Claim 16 (depends on 13)

The process of claim 13 wherein said sulfating step is carried out at a temperature in the range of from about 5.degree. C. to about 40.degree. C. and a pressure in the range of from about 1 atmosphere to about 2 atmospheres.

### Claim 17 (depends on 13)

The process of claim 13 wherein following step a), the product of step a) is subjected to deacidification by water washing.

### Claim 18 (depends on 13)

The process of claim 13 wherein said base in step b) is selected from ammonium, alkali metal or alkaline earth metal hydroxides, carbonates or bicarbonates.

### Claim 19 (depends on 18)

The process of claim 18 wherein said base is selected from the group consisting of sodium hydroxide, potassium hydroxide and mixtures thereof.

### Claim 20 (depends on 13)

The process of claim 13 wherein said base in aqueous solution comprises from about 10 percent by weight to about 85 percent by weight base in water.

### Claim 21 (depends on 20)

The process of claim 20 wherein said base in aqueous solution comprises from about 20 percent by weight to about 50 percent by weight base in water.

### Claim 22 (depends on 13)

The process of claim 13 wherein said neutralization in step b) is carried out at temperatures in the range of from about 20.degree. C. to about 65.degree. C. and pressures in the range of from about 1 atmosphere to about 2 atmospheres.

### Claim 23 (depends on 13)

The process of claim 13 wherein said saponification in step c) is carried out at a temperature in the range of from about 80.degree. C. to about 105.degree. C. and a pressure of from about 1 atmosphere to about 2 atmospheres.

### Claim 24 (depends on 13)

The process of claim 13 wherein the nonionic organic liquid diluent is selected from the group consisting of aliphatic hydrocarbons, aromatic hydrocarbons and mixtures thereof.

### Claim 25 (depends on 24)

The process of claim 24 wherein the nonionic organic liquid diluent is selected from the group consisting of heptane, toluene, isooctane, nonane, and mixtures thereof.

### Claim 26 (depends on 13)

The process of claim 13 wherein the nonionic organic liquid diluent is added in step a).

### Claim 27 (depends on 13)

The process of claim 13 wherein the nonionic organic liquid diluent is added in step b).

### Claim 28 (depends on 13)

The process of claim 13 wherein the nonionic organic liquid diluent is added in step c).

### Claim 29 (depends on 13)

The process of claim 13 wherein prior to drying, the crystallized solid secondary alkyl sulfate-containing surface active composition is washed with chilled water.

### Claim 30 (depends on 13)

The process of claim 13 wherein following drying, the crystallized solid secondary alkyl sulfate-containing surface active composition is washed with chilled water.

### Claim 31 (depends on 13)

The process of claim 13 wherein said product recovered in step e) contains from about 80 percent by weight to about 99 percent by weight secondary alkyl sulfate.

### Claim 32 (depends on 31)

The process of claim 31 wherein said product recovered in step e) contains from about 88 percent by weight to about 99 percent by weight secondary alkyl sulfate.