# US 9,751,905 B2 · Process for extracting mineral oil using surfactants based on butylene oxide-containing alkyl alkoxylates

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- Number: US 9,751,905 B2
- Document ID: US9751905B2
- Status: Granted
- Kind: B2
- Application number: 14/081,027
- Filed: 2013-11-15
- Published: 2014-06-05
- Granted: 2017-09-05
- Earliest claimed: 2010-03-10
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Christian Bittner; Günter Oetter; Jack Tinsley; Christian Spindler; Gabriela Alvarez-Juergenson; Sophie Vogel
- Web page: https://patentgrep.com/patent/US9751905B2

## CPC

- C07F 9/46: Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids {including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof}
- C07C 305/06: Hydrogenosulfates
- C09K 8/584: characterised by the use of specific surfactants
- C09K 23/42: Ethers, e.g. polyglycol ethers of alcohols or phenols
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A surfactant and a surfactant formulation comprising at least one ionic surfactant of the general formula R1—O-(D)n-(B)m-(A)l-XY−M+ where R1 is a linear or branched, saturated or unsaturated, aliphatic and/or aromatic hydrocarbon radical having 8 to 30 carbon atoms, A is ethyleneoxy, B is propyleneoxy, and D is butyleneoxy, l is from 0 to 99, m is from 0 to 99 and n is from 1 to 99, X is an alkyl or alkylene group having 0 to 10 carbon atoms, M+ is a cation, and Y− is selected from the group of sulfate groups, sulfonate groups, carboxylate groups and phosphate groups.

## Claims

### Claim 1

An aqueous surfactant formulation comprising at least one ionic surfactant of the general formula
R1—O-(D)n-(B)m-(A)l-XY−M+, where
R1 is selected from: iso-C17H35; a fatty alcohol mixture with linear C16H33 and C18H37 alkyl chains; derived from a C16 Guerbet alcohol, 2-hexyldecan-1-ol; derived from a C24 Guerbet alcohol, 2-decyltetradecanol; or derived from a C28 Guerbet alcohol, 2-dodecylhexadecanol,
A is ethyleneoxy,
B is propyleneoxy, and
D is butyleneoxy,
l is from 0 to 99,
m is from 5 to 9, and
n is from 2 to 10,
X is an alkyl or alkylene group having 0 to 10 carbon atoms,
M+ is a cation, and
Y− is selected from the group consisting of sulfate groups, sulfonate groups, carboxylate groups and phosphate groups, where
the A, B and D groups are in the form of two, three, four or more blocks beginning at the alcohol with the sequence D-B-A, the sum of l+m+n is in the range from 7 to 99 and the proportion of 1,2-butylene oxide, based on the total amount of butylene oxide, is at least 80%.

### Claim 2 (depends on 1)

The surfactant formulation according to claim 1, wherein
Y− is selected from the group of sulfate groups, sulfonate groups, and carboxylate groups, where
the A, B and D groups are present to an extent of more than 80% in block form, the sum of l+m+n is in the range from 7 to 49, and the proportion of 1,2-butylene oxide, based on the total amount of butylene oxide in the molecule, is at least 90%.

### Claim 3 (depends on 2)

The surfactant formulation according to claim 2, wherein R1 is a linear fatty alcohol having 16 or 18 carbon atoms and n is from 3 to 10.

### Claim 4 (depends on 1)

The surfactant formulation according to claim 1, wherein the concentration of all surfactants together is 0.05 to 5% by weight, based on the total amount of the aqueous surfactant formulation.

### Claim 5

A surfactant of the general formula
R1—O-(D)n-(B)m-(A)l-XY−M+, where
R1 is selected from: iso-C17H35; a fatty alcohol mixture with linear C16H33 and C18H37 alkyl chains; derived from a C16 Guerbet alcohol, 2-hexyldecan-1-ol; derived from a C24 Guerbet alcohol, 2-decyltetradecanol; or derived from a C28 Guerbet alcohol, 2-dodecylhexadecanol,
A is ethyleneoxy,
B is propyleneoxy, and
D is butyleneoxy,
l is from 0 to 99,
m is from 5 to 9 and
n is from 2 to 10,
X is an alkyl or alkylene group having 0 to 10 carbon atoms,
M+ is a cation, and
Y− is selected from the group consisting of sulfate groups, sulfonate groups, carboxylate groups and phosphate groups, where
the A, B and D groups are in the form of two, three, four or more blocks beginning at the alcohol with the sequence D-B-A, the sum of l+m+n is in the range from 7 to 99 and the proportion of 1,2-butylene oxide, based on the total amount of butylene oxide, is at least 80%.

### Claim 6 (depends on 5)

The surfactant according to claim 5, wherein the sum of l+m+n is in the range from 7 to 49.

### Claim 7 (depends on 5)

The surfactant according to claim 5, Wherein the proportion of 1,2-butylene oxide, based on the total amount of butylene oxide, is at least 90%.

### Claim 8 (depends on 5)

The surfactant according to claim 5, wherein
R1 is a fatty alcohol mixture with linear C16H33 and C18H37 alkyl chains,
n is from 3 to 10, and
Y− is selected from the group consisting of sulfate groups, sulfonate groups, and carboxylate groups, where the A, B and D groups are present to an extent of more than 80% in block form, the sum of l+m+n is in the range from 7 to 49, and the proportion of 1,2-butylene oxide, based on the total amount of butylene oxide in the molecule, is at least 90%.

### Claim 9 (depends on 5)

The surfactant according to claim 5, wherein R1 is a linear fatty alcohol having 16 or 18 carbon atoms and n is from 3 to 10.

### Claim 10 (depends on 5)

The surfactant according to claim 5, wherein R1 is a linear fatty alcohol having 16 or 18 carbon atoms and the surfactant is selected from the group consisting of
R1O-D2-B7—XY−M+,
R1O-D3-B7—XY−M+,
R1O-D5-B7—XY−M+, and
R1O-D7-B7A10-XY−M+.

### Claim 11 (depends on 5)

The surfactant according to claim 5, wherein R1 is a C16 Guerbet alcohol, 2-hexyldecan-1-ol.