# US 2010/0168450 A1 · Novel branched alkoxylates

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- Number: US 2010/0168450 A1
- Document ID: US20100168450A1
- Status: Published application
- Kind: A1
- Application number: 12/596,919
- Filed: 2008-04-24
- Published: 2010-07-01
- Earliest claimed: 2007-04-27
- Inventors: Johan A. Thoen; Camiel F. Bartelink; Pierre Varineau
- Web page: https://patentgrep.com/patent/US20100168450A1

## CPC

- C07C 41/03: by reaction of oxirane rings with hydroxy groups
- C07C 41/16: by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
- C07C 41/42: by distillation
- C07C 41/44: by treatments giving rise to a chemical modification (by chemisorption C07C41/36)
- C07C 43/11: Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
- C08G 65/24: Epihalohydrins
- C08G 65/2609: {containing aliphatic hydroxyl groups}
- C08G 65/2648: {Alkali metals or compounds thereof}
- C08G 65/2654: {Aluminium or boron; Compounds thereof}
- C08G 65/2678: {Sulfur or compounds thereof}
- C11D 1/72: Ethers of polyoxyalkylene glycols
- C11D 1/721: {End blocked ethers}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

Novel alkylene oxide-extended alkoxylates of a branched 1,3-dialkyl-oxy-2-propanol may be prepared by a convenient process comprising adding epichlorohydrin to a stoichiometric excess of a branched alcohol, wherein the molar ratio of branched alcohol:epichlorohydrin is at least about 3:1, preferably in the presence of a Group 1 A metal hydroxide and a phase transfer catalyst, followed by alkoxylation in the presence of an ionic catalyst. The branched alkyl chain may be saturated or unsaturated and may contain one or more heteroatoms. The repeating alkoxy units from the alkylene oxide are in the 2-position. The compositions are useful as surfactants, diluents, and the like, and may be less expensive than other branched surfactants.

## Claims

### Claim 1

A process for preparing a branched surfactant comprising
reacting 1-chloro-2,3-expoxypropane and a stoichiometric excess of a branched alcohol, such that the molar ratio of the branched alcohol to 1-chloro-2,3-epoxypropane is at least about 3:1 during the reaction, to form a reaction product, and reacting the reaction product with from 2 to 12 moles of an alkylene oxide per mole of reaction product in the presence of an ionic catalyst, to form a branched, alkylene oxide-extended 1,3-dialkyloxy-2 propanol alkoxylate.

### Claim 2 (depends on 1)

The process of claim 1 wherein the branched alcohol has from 3 to 28 carbon atoms, and is saturated or unsaturated.

### Claim 3 (depends on 1)

The process of claim 1 wherein the branched alcohol contains at least one heteroatom selected from the group consisting of elements of Group IVA, VA, VIA and VIIA, and combinations thereof.

### Claim 4 (depends on 1)

The process of claim 1 wherein the 1-chloro-2,3-epoxypropane is added to the branched alcohol continuously or stepwise.

### Claim 5

(canceled)

### Claim 6 (depends on 1)

The process of claim 1 wherein the molar ratio of branched alcohol/metal hydroxide/1-chloro-2,3-epoxypropane during the reaction is from about 1/0.7/0.01 to about 1/0.7/0.10.

### Claim 7 (depends on 6)

The process of claim 6 wherein the molar ratio of branched alcohol/metal hydroxide/1-chloro-2,3-epoxypropane during the reaction is from about 1/0.7/0.06 to about 1/0.7/0.3.

### Claim 8 (depends on 1)

The process of claim 1 wherein the molar ratio of branched alcohol/metal hydroxide/1-chloro-2,3-epoxypropane is varied during the reaction, from about 1/0.7/0.01 to about 1/0.7/0.33.

### Claim 9 (depends on 1)

The process of claim 1 further comprising a phase transfer catalyst.

### Claim 10 (depends on 9)

The process of claim 9 wherein the phase transfer catalyst is selected from the group consisting of trialkylamine, alkyldimethylbenzylammonium salt, tetraalkylammonium salt, N,N-dialkylamino-3-alkyloxy-2-propanol, N,N,N-trialkyl-3-alkyloxy-2-hydroxypropyl-ammonium salt and alkyltrimethylammonium salt, wherein the salt includes an anion selected from the group consisting of halide, methylsulfate, and hydrogensulfate; tetrabutylammonium bromide, tetrabutylammonium hydrogensulfate, cetyltrimethylammonium chloride, lauryldimethylbenzylammonium chloride, N,N-dimethylamino-3-hexyloxy-2-propanol, N,N-dimethylamino-3-octyloxy-2-propanol, N,N-dimethylamino-3-dodecyloxy-2-propanol, N,N-dimethylamino-3-octadecyloxy-2-propanol, N,N-dimethylamino-3-(1′H,1′H,2′H,2′H-perfluoro)hexyloxy-2-propanol, N,N-dimethyl-amino-3-(1′H,1′H,2′H,2′H-perfluoro)octyloxy-2-propanol, N,N-bis(2-hydroxyethyl)-amino-3-hexyloxy-2-propanol, N,N-bis(2-hydroxyethyl)amino-3-octyloxy-2-propanol, N,N-bis(2-hydroxyethyl)amino-3-dodecyloxy-2-propanol, N,N-bis(2-hydroxyethyl)amino-3-octadecyloxy-2-propanol, N,N-bis(2-hydroxyethyl)-amino-3-1′H,1′H,2 ′H,2′H-perfluoro)hexyloxy-2-propanol, N,N-bis(2-hydroxypropyl-ammonium methylsulfate, N,N,N-trimethyl-3-octyloxy-2-hydroxypropylammonium methyl-sulfate, N,N,N-trimethyl-3-dodecyloxy-2-hydroxypropylammonium methyl-sulfate, N,N,N-trimethyl-3-octyloxy-2-hydroxypropylammonium chloride, N,N,N-trimethyl-3-octyloxy-2-hydroxypropylammonium bromide, N,N-bis(2-hydroxyethyl)-N-methyl-3-hexyloxy-2-hydroxypropylammonium methylsulfate, N,N-bis(2-hydroxy-ethyl)-N-methyl-3-octyloxy-2-hydroxypropylammonium methylsulfate, N,N-bis(2-hydroxy-ethyl)-N-methyl-3-dodecyloxy-2-hydroxypropylammonnium methylsulfate, N,N-bis(2-hydroxyethyl)-N-methyl-3-octadecyloxy-2-hydroxpropylammonium methyl-sulfate, N,N-bis(2-hydroxyethyl)-N-methyl-3-(1′H,1′H,2′H,2′H-perfluoro)-hexyloxy-2-hydroxy-propylammonium methylsulfate, N,N-bis(2-hydroxyethyl)-N-methyl-3-(1′H,1′H,2′H,2′H-perfluoro)octyloxy-2-hydroxypropylammonium methyl-sulfate, an esterified compound of octanoic acid and N,N-dimethyl-3-oxtyloxy-2-propanol, an esterified compound of hexadecanoic aid and N,N-dimetyl-3-octyloxy-2-propanol, and combinations thereof.

### Claim 11 (depends on 1)

The process of claim 1 wherein the reacting is carried out at a temperature from about 10° C. to about 100° C.

### Claim 12 (depends on 1)

The process of claim 1 wherein the molar ratio of the branched 1,3-dialkyloxy-2-propanol to alkylene oxide is from 1:2 to 1:20.

### Claim 13 (depends on 12)

The process of claim 12 wherein the molar ratio of the branched 1,3-dialkyloxy-2-propanol to alkylene oxide is from about 1:3 to about 1:15.

### Claim 14 (depends on 1)

The process of claim 1 wherein the branched 1,3-dialkyloxy-2-propanol alkoxylate contains an alkyl moiety selected from the group consisting of methyl-, ethyl-, propyl- and butyl-branched pentyl-, hexyl-, heptyl-, octyl-, nonyl-, decyl-, undecyl-, dodecyl- and tridecyl-aliphatic moieties.

### Claim 15 (depends on 12)

The process of claim 12 wherein the branched 1,3-dialkyloxy-2-propanol alkoxylate exhibits surfactant properties.

### Claim 16

A surfactant composition comprising a branched 1,3-dialkyloxy-2-propanol alkoxylate prepared by a process comprising reacting a 1-chloro-2,3-epoxypropane and a stoichiometric excess of a branched alcohol having from 3 to 28 carbon atoms, such that the molar ratio of branched alcohol to 1-chloro-2,3-epoxypropane is at least about 3:1 during the reaction, in the presence of a metal hydroxide and a phase transfer catalyst, such that a reaction product comprising a branched 1,3-dialkyloxy-2-propanol alkoxylate is formed; and reacting the reaction product and from about 2 to about 12 moles of an alkylene oxide per mole of reaction product, in the presence of an ionic catalyst, to form a branched, alkylene oxide-extended 1,3-dialkyloxy-2-propanol alkoxylate.

### Claim 17 (depends on 16)

The surfactant composition of claim 16 wherein the reaction product comprises the branched 1,3-dialkyloxy-2-propanol in an amount of at least about 65 percent by weight.

### Claim 18 (depends on 16)

The surfactant composition of claim 16 wherein the yield of branched 1,3-dialkyloxy-3-propanol is at least about 50 percent of theoretical based on the 1-chloro-2,3-epoxypropane.

### Claim 19 (depends on 16)

The surfactant composition of claim 16 wherein the branched 1,3-dialkyloxy-2-propanol is in a molar ratio relative to the alkylene oxide from 1:2 to 1:20.

### Claim 20 (depends on 19)

The surfactant composition of claim 19 wherein the branched 1,3-dialkyloxy-2-propanol is in a molar ratio relative to the alkylene oxide from 1:3 to 1:15.

### Claim 21 (depends on 16)

The surfactant composition of claim 16 wherein the ionic catalyst is selected from the group consisting of cationic catalysts, anionic catalysts, and combinations thereof.