# US 2019/0169531 A1 · Anionic surfactants and detergents and cleaning agent containing same

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- Number: US 2019/0169531 A1
- Document ID: US20190169531A1
- Status: Published application
- Kind: A1
- Application number: 16/273,382
- Filed: 2019-02-12
- Published: 2019-06-06
- Earliest claimed: 2016-08-12
- Assignees: Henkel AG & Co. KGaA
- Applicants: Henkel AG & Co. KGaA
- Inventors: Christian Kropf; Alexander Schulz; Anna Klemmer; Regina Palkovits; Peter Hausoul; Lukas Kipshagen
- Web page: https://patentgrep.com/patent/US20190169531A1

## CPC

- C11D 1/26: derived from heterocyclic compounds
- C07D 307/12: Radicals substituted by oxygen atoms
- C11D 17/043: {Liquid or thixotropic (gel) compositions}
- C11D 17/044: {Solid compositions}
- B01J 29/03: not having base-exchange properties {(B01J29/005 takes precedence)}
- B01J 29/084: {Y-type faujasite}
- B01J 29/7007: {Zeolite Beta}
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

An anionic surfactant of general formula (I) in which n and m are, independently of one another, numbers from 0 to 17 and 2<n+m<20, and X+ is a charge-balancing cation. The invention also relates to a production method by way of: the acid-catalysed reaction of 2,5-bis(hydroxymethyl) tetrahydrofuran with an alkene having 5 to 22 C atoms in equimolar amounts, at an increased temperature; subsequent sulphation with a sulphating agent; and optional neutralisation by a subsequent reaction with X+OH− or X+2CO2−3, where X+ is an alkali metal cation or a group N+R1R2R3, in which R1, R2 and R3 are, independently of one another, hydrogen, an alkyl group with 1 to 6 C atoms, or a hydroxyalkyl group with 2 to 6 C atoms. Detergents or cleaning agents containing—the surfactant, and the use of same to improve the performance of the detergents or cleaning agents, are also disclosed.

## Claims

### Claim 1

An anionic surfactant of general formula (I),
in which n and m independently of one another represent numbers from 0 to 17 and 2<n+m<20, and X+ represents a charge-balancing cation.

### Claim 2 (depends on 1)

A method for preparing an anionic surfactant according to claim 1,
in which n and m independently of one another represent numbers from 0 to 17 and 2<n+m<20, and X+ represents a charge-balancing cation,
by acid-catalyzed reaction of 2,5-bis (hydroxymethyl) tetrahydrofuran with an alkene having C atoms in equimolar amounts at elevated temperature to form a compound of general formula (II),
subsequent sulfation using a sulfating agent and optionally neutralizing by means of subsequent reaction with X+OH− or X+2CO2−3, where X+ represents an alkali metal cation or a group N+R1R2R3, in which R1, R2 and R3 independently of one another represent hydrogen, an alkyl group having 1 to 6 C atoms or a hydroxy alkyl group having 2 to 6 C atoms.

### Claim 3 (depends on 2)

The method according to claim 2, characterized in that 2,5-bis (hydroxymethyl) tetrahydrofuran is stirred together with the alkene and an acidic catalyst at a temperature in the range from 140° C. to 200° C. for a period of 8 hours to 24 hours, and the resulting compound of general formula (II) is reacted with a sulfating agent at a temperature in the range from −20° C. to 75° C., and a duration of 1 hour to 24 hours.

### Claim 4

A washing or cleaning agent containing an anionic surfactant of general formula (I),
in which n and m independently of one another represent numbers from 0 to 17 and 2<n+m<20, and X+ represents a charge-balancing cation.

### Claim 5 (depends on 4)

The washing or cleaning agent according to claim 4, characterized in that it contains from 1 wt. % to 99 wt. % of the surfactant of general formula (I).

### Claim 6 (depends on 4)

The washing or cleaning agent according to claim 4, characterized in that it additionally contains up to 99 wt. % of a further surfactant.

### Claim 7 (depends on 4)

The washing or cleaning agent according to claim 4, characterized in that it is particulate and contains builders, or in that it is liquid and 1 wt. % to 90 wt. % water, water-miscible solvent or a mixture of water and water-miscible solvent.

### Claim 8 (depends on 4)

The washing or cleaning agent according to claim 4, characterized in that it is portioned ready to be individually dosed in a chamber formed of water-soluble material and contains less than 15 wt. % water.

### Claim 9 (depends on 1)

The surfactant according to claim 1, characterized in that, in the compounds of general formula (I), n represents a number from 0 to 3, and m represents a number from 5 to 14, and/or X+ is selected from the group consisting of the proton, alkali metal cations and the group N+R1R2R3, in which R1, R2 and R3 independently of one another represent hydrogen, an alkyl group having 1 to 6 C atoms or a hydroxy alkyl group having 2 to 6 C atoms.

### Claim 10 (depends on 2)

The method according to claim 2, for preparing an anionic surfactant of general formula (I),
in which n and m independently of one another represent numbers from 0 to 17 and 2<n+m<20, and X+ represents a charge-balancing cation,
by acid-catalyzed reaction of 2,5-bis (hydroxymethyl) tetrahydrofuran with a 1-alkene, having 5 to 22 C atoms in equimolar amounts at elevated temperature to form a compound of general formula (II),
subsequent sulfation using a sulfating agent and optionally neutralizing by means of subsequent reaction with X+OH− or X+2CO2−3, where X+ represents an alkali metal cation or a group N+R1R2R3, in which R1, R2 and R3 independently of one another represent hydrogen, an alkyl group having 1 to 6 C atoms or a hydroxy alkyl group having 2 to 6 C atoms.

### Claim 11 (depends on 2)

The method according to claim 2, for preparing an anionic surfactant of general formula (I),
in which n and m independently of one another represent numbers from 0 to 17 and 2<n+m<20, and X+ represents a charge-balancing cation,
by acid-catalyzed reaction of 2,5-bis (hydroxymethyl) tetrahydrofuran with a 1-alkene, having 9 to 19 C atoms in equimolar amounts at elevated temperature to form a compound of general formula (II),
subsequent sulfation using a sulfating agent and optionally neutralizing by means of subsequent reaction with X+OH− or X+2CO2−3, where X+ represents an alkali metal cation or a group N+R1R2R3, in which R1, R2 and R3 independently of one another represent hydrogen, an alkyl group having 1 to 6 C atoms or a hydroxy alkyl group having 2 to 6 C atoms.

### Claim 12 (depends on 3)

The method according to claim 3, characterized in that 2,5-bis (hydroxymethyl) tetrahydrofuran is stirred together with the alkene and an acidic solid catalyst at a temperature in the range from 180° C. to 200° C. for a period of 12 hours to 18 hours, and the resulting compound of general formula (II) is reacted with chlorosulfonic acid or sulfur trioxide pyridine at a temperature in the range from 25° C. to 75° C., and a duration of 6 to 18 hours.

### Claim 13 (depends on 12)

The method according to claim 12, characterized in that the acidic solid catalyst is acidic zeolite or a zeolite in the so-called H-form.

### Claim 14 (depends on 13)

The method according to claim 13, characterized in that the zeolite in the so-called H-form is zeolite beta and/or zeolite Y.

### Claim 15 (depends on 5)

The washing or cleaning agent according to claim 5, characterized in that it contains from 3 wt. % to 85 wt. % of the surfactant of general formula (I).

### Claim 16 (depends on 6)

The washing or cleaning agent according to claim 6, characterized in that it additionally contains from 3 wt. % to 85 wt. % of a further surfactant.

### Claim 17 (depends on 7)

The washing or cleaning agent according to claim 7, characterized in that it is particulate and contains builders in an amount in the range from 1 wt. % to 60 wt. % or in that it is liquid and 10 wt. % to 85 wt. % water, water-miscible solvent or a mixture of water and water-miscible solvent.

### Claim 18 (depends on 8)

The washing or cleaning agent according to claim 8, characterized in that it is portioned ready to be individually dosed in a chamber formed of water-soluble material and contains in the range from 1 wt. % to 12 wt. % water.