# US 6,723,862 B2 · Fatty acid isomerization with mesoporous zeolites

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 6,723,862 B2
- Document ID: US6723862B2
- Status: Granted
- Kind: B2
- Application number: 10/390,851
- Filed: 2003-03-18
- Published: 2003-10-09
- Granted: 2004-04-20
- Earliest claimed: 2002-04-02
- Assignees: Akzo Nobel N.V.
- Inventors: Zhang Shuguang; Zhang Zongchao
- Web page: https://patentgrep.com/patent/US6723862B2

## CPC

- C07C 51/353: by isomerisation; by change of size of the carbon skeleton
- B01J 29/041: {Mesoporous materials having base exchange properties, e.g. Si/Al-MCM-41}
- C07C 67/333: by isomerisation; by change of size of the carbon skeleton (introduction or elimination of carboxyl groups C07C67/313, C07C67/32)
- B01J 29/7007: {Zeolite Beta}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

The present invention generally relates to a process for the preparation of branched fatty acids from straight chain unsaturated fatty acid feedstocks with a strongly acidic and hydrothermally stable mesoporous aluminosilicate and/or aluminophosphate catalyst materials having mesopores of 15-500 Å and contain primary and secondary nanosized zeolite structural units in the walls that separate mesopores.

## Claims

### Claim 1

A process for the isomerization of a feedstock which comprises unsaturated linear fatty acids, alkyl esters of unsaturated fatty acids or mixtures thereof, wherein said process comprises subjecting said feedstock to an isomerization reaction in the presence of an acidic catalyst, wherein said acidic catalyst comprises a mesoporous crystalline phase having pore walls containing primary and secondary crystalline building unit structures.

### Claim 2 (depends on 1)

The process of claim 1 wherein said catalyst comprises both mesopores and micropores.

### Claim 3 (depends on 2)

The process of claim 2 wherein said catalyst is a mesoporous aluminosilicate or a mesoporous metal containing aluminosilicate.

### Claim 4 (depends on 3)

The process of claim 3 wherein said mesoporous aluminosilicate is a mesoporous zeolite.

### Claim 5 (depends on 4)

The process of claim 4 wherein said mesoporous zeolite catalyst material comprises mesopores of 15-500 Å and primary and secondary nanosized zeolite structural units in the walls that separate mesopores.

### Claim 6 (depends on 1)

The process of claim 1, wherein the isomerization of said feedstock comprises branching of the fatty acids or alkyl esters thereof.

### Claim 7 (depends on 6)

The process of claim 6 wherein said mesoporous zeolite comprises hexagonal mesopores, the pore wall structures of said mesopores containing primary and secondary zeolite building units.

### Claim 8 (depends on 5)

The process of claim 5 wherein said mesoporous zeolite is characterized by an IR absorption at 400-600 cm−1.

### Claim 9 (depends on 1)

The process of claim 1 wherein said primary and or secondary crystalline building units are based on at least one zeolite selected from the group consisting of zeolite A, Beta zeolite, zeolite X, zeolite Y, zeolite L, zeolite ZK-5, zeolite ZK-4, zeolite ZSM-5, zeolite ZSM-11, zeolite ZSM-12, zeolite ZSM-20, ZSM-35, zeolite ZSM-23, VPI-5 and mixtures thereof.

### Claim 10 (depends on 1)

The process according to claim 1 wherein the feedstock comprises of at least 50% by weight of unsaturated fatty acids, alkyl esters of unsaturated fatty acids or mixtures thereof.

### Claim 11 (depends on 10)

The process of claim 10 wherein the feedstock comprises of at least 70% by weight oleic acid.

### Claim 12 (depends on 1)

The process claim 1 wherein at least part of the isomerization is performed at a temperature of between 100° C. and 350° C.

### Claim 13 (depends on 12)

The process of claim 12 wherein at least part of the isomerization is carried out at a temperature of between 230° C. and 285° C.

### Claim 14 (depends on 1)

The process of claim 1 wherein said isomerization is conducted in a batch reactor.

### Claim 15 (depends on 1)

The process of claim 1 wherein said isomerization is conducted in a fixed bed continuous flow reactor.

### Claim 16 (depends on 1)

The process of claim 1 wherein the feedstock is contacted with the catalyst for a period of at least 30 minutes.

### Claim 17 (depends on 14)

The process of claim 14 wherein the amount of catalyst used is between 0.5 and 30% by weight of the feedstock in the batch reactor.

### Claim 18 (depends on 15)

The process of claim 15 wherein the weight hour space velocity is between 0.01 and 100 in a continuous flow reactor.

### Claim 19

A process for the isomerization of a feedstock which comprises unsaturated linear fatty acids, alkyl esters of unsaturated fatty acids or mixtures thereof, wherein said process comprises subjecting said feedstock to an isomerization reaction in the presence of an acidic catalyst, wherein said acidic catalyst comprises a aluminophosphate or a metal containing aluminophosphate.

### Claim 20 (depends on 19)

The process of claim 19 wherein said catalyst comprises a mesoporous crystalline phase having pore walls containing primary and secondary crystalline building unit structures comprising aluminophosphate or a metal containing aluminophosphate.

### Claim 21

A branched fatty acid or alkyl ester thereof prepared by isomerizing a feedstock which comprises unsaturated linear fatty acids, alkyl esters of unsaturated fatty acids or mixtures thereof, wherein said process comprises subjecting said feedstock to an isomerization reaction in the presence of an acidic catalyst, wherein said acidic catalyst comprises a mesoporous crystalline phase having pore walls containing primary and secondary crystalline building unit structures.

### Claim 22 (depends on 21)

The branched fatty acid or alkyl ester thereof of claim 21 wherein said catalyst comprises both mesopores and micropores.

### Claim 23 (depends on 22)

The branched fatty acid or alkyl ester thereof of claim 22 wherein said catalyst is a mesoporous aluminosilicate or a mesoporous metal containing aluminosilicate.

### Claim 24 (depends on 23)

The branched fatty acid or alkyl ester thereof of claim 23 wherein said mesoporous aluminosilicate is a mesoporous zeolite.

### Claim 25 (depends on 24)

The branched fatty acid or alkyl ester thereof of claim 24 wherein said mesoporous zeolite catalyst material comprises mesopores of 15-500 Å and primary and secondary nanosized zeolite structural units in the walls that separate mesopores.

### Claim 26 (depends on 25)

The branched fatty acid or alkyl ester thereof of claim 25 wherein said mesoporous zeolite comprises hexagonal mesopores, the pore wall structures of said mesopores containing primary and secondary zeolite building units.

### Claim 27 (depends on 21)

The branched fatty acid or alkyl ester thereof of claim 21 wherein said mesoporous zeolite is characterized by an IR absorption at 400-600 cm−1.

### Claim 28 (depends on 21)

The branched fatty acid or alkyl ester thereof of claim 21 wherein said primary and or secondary crystalline building units are based on at least one zeolite selected from the group consisting of zeolite A, Beta zeolite, zeolite X, zeolite Y, zeolite L, zeolite ZK-5, zeolite ZK-4, zeolite ZSM-5, zeolite ZSM-11, zeolite ZSM-12, zeolite ZSM-20, ZSM-35, zeolite ZSM-23, VPI-5 and mixtures thereof.

### Claim 29 (depends on 21)

The branched fatty acid or alkyl ester thereof according to claim 21 wherein the feedstock comprises of at least 50% by weight of unsaturated fatty acids, alkyl esters of unsaturated fatty acids or mixtures thereof.

### Claim 30 (depends on 21)

The branched fatty acid or alkyl ester thereof of claim 21 wherein at least part of the isomerization is performed at a temperature of between 100° C. and 350° C.

### Claim 31 (depends on 30)

The process of claim 30 wherein the amount of catalyst used is between 0.5 and 30% by weight of the feedstock.

### Claim 32 (depends on 21)

A derivative prepared from the branched fatty acid or alkyl ester thereof of claim 21 wherein said derivative is selected from the group consisting essentially of amphoteric, non-ionic, anionic and cationic surfactants.

### Claim 33 (depends on 32)

The derivative of claim 32 wherein said derivative is selected from the group consisting essentially of fatty acid glucamides, glycerol esters, polyhydric esters, sulfoesters, sucrose esters, alpha sulfonates, N-acyl sarcosinates, acylated protein hydrolysates, acyl isethionates, amido propyl amine and derivatives thereof, alkanolamide, ethoxylated alkanolamides, nitrites, N-aryl taurates, soaps, esteramines, esterquats, alkyl polyglycosides (APGs), alcohol sulfates, phosphate esters, polyalkoxycarbonates and mixtures thereof.