# US 2026/0274769 A1 · Process for producing renewable mono-methyl alkylbenzene products

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- Number: US 2026/0274769 A1
- Document ID: US20260274769A1
- Status: Published application
- Kind: A1
- Application number: 19/667,013
- Filed: 2026-05-04
- Published: 2026-09-17
- Earliest claimed: 2023-05-30
- Assignees: Uop LLC
- Applicants: Uop LLC
- Inventors: Geoffrey W. Fichtl; Phuong T.M. Do; James T. Wexler; Hai Du; Eseoghene Jeroro; Patrick C. Whitchurch
- Web page: https://patentgrep.com/patent/US20260274769A1

## CPC

- C07C 1/213: by splitting of esters
- C07C 2/64: Addition to a carbon atom of a six-membered aromatic ring
- C07C 4/06: Catalytic processes {(C07C4/025 takes precedence)}
- C07C 5/05: Partial hydrogenation
- C07C 5/222: {with crystalline alumino-silicates, e.g. molecular sieves}
- C07C 5/327: Formation of non-aromatic carbon-to-carbon double bonds only
- C07C 7/00: Purification; Separation; Use of additives (working-up undefined gaseous mixtures obtained by cracking hydrocarbon oils C10G70/00)
- C07C 7/13: by molecular-sieve technique
- C07C 2523/652: Chromium, molybdenum or tungsten
- C07C 2523/84: with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C 2529/85: Silicoaluminophosphates (SAPO compounds)
- C07C 2601/16: the ring being unsaturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Processes for producing mono-methyl alkylbenzenes from natural oils are described. The processes includes a linear selective cracking process to crack C14+ chains into C9 to C14 chains which are useful for making linear alkylbenzene for use in detergents and a hydroisomerization step to produce paraffins with mono-methyl branching which can be reacted with benzene to form the mono-methyl alkyl benzenes.

## Claims

### Claim 1

A method for production of a mono methyl alkyl benzene product from a natural oil comprising:
deoxygenating the natural oil to form a paraffin stream comprising C9 to C28 carbon chains;
linear selective cracking the paraffin stream in a separate linear selective cracking unit under linear selective cracking conditions in the presence of a linear selective cracking catalyst to form a first stream comprising normal or lightly branched C9 to C14 paraffins, a second stream comprising C14+ paraffins, and a third stream comprising iso paraffins;
isomerizing the first stream under isomerization conditions in the presence of an isomerization catalyst to form an isomerized stream comprising C9 to C14 mono-methyl paraffins;
removing contaminants from the isomerized stream to form a decontaminated stream wherein the contaminants comprise sulfur compounds, or nitrogen compounds, or phosphorous compounds, or oxygenates, or aromatics, or combinations thereof;
dehydrogenating the decontaminated stream to provide a dehydrogenated stream comprising mono-olefins, di-olefins, and aromatics;
selectively hydrogenating the di-olefins in the dehydrogenated stream to form additional mono-olefins, and separating and removing the aromatics from the mono-olefins to form an aromatics stream comprising the aromatics and a mono-olefins stream comprising the mono-olefins;
alkylating benzene with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene; and isolating the alkylbenzenes to provide the alkylbenzene product derived from the natural oil.

### Claim 2 (depends on 1)

The method of claim 1 further comprising:
separating the isomerized stream through a first absorption separation system, wherein the mono methyl paraffins in the mixture are preferentially adsorbed by a first adsorbent and where the non-mono methyl paraffins remain in the fluid phase, before removing the contaminants from the isomerized stream; or
separating the decontaminated stream through a second absorption separation system, wherein the mono methyl paraffins in the mixture are preferentially adsorbed by a second adsorbent and where the non-mono methyl paraffins remain in the fluid phase, before dehydrogenating the decontaminated stream.

### Claim 3 (depends on 2)

The method of claim 2:
wherein the adsorbent in the first absorption separation system is divided into a plurality of adsorbent bed zones; or
wherein the adsorbent in the second absorption separation system is divided into a plurality of adsorbent bed zones;
or both.

### Claim 4 (depends on 1)

The method of claim 1 wherein the isomerized stream comprises a weight ratio of mono-methyl paraffins to normal paraffins of 3 to 60.

### Claim 5 (depends on 1)

The method of claim 1 further comprising:
recycling the second stream comprising C14+ paraffins to the linear selective cracking unit.

### Claim 6 (depends on 1)

The method of claim 1 wherein the linear selective cracking catalyst comprises a ruthenium, or a platinum, or a nickel supported catalyst, or mixtures thereof.

### Claim 7 (depends on 1)

The method of claim 1 wherein the linear selective cracking conditions comprise a temperature in a range of 290° C. to 455° C., or a pressure in a range of 2.8 MPa to 17.5 MPa, or combinations thereof.

### Claim 8 (depends on 1)

The method of claim 1 wherein the isomerization conditions comprise a temperature in a range of 280° C. to 400° C., or a pressure in a range of 2.8 MPa to 17.5 MPa, or 1500-10000 standard cubic foot of hydrogen per barrel of feed, or 025-2.5 LHSV, or combinations thereof.

### Claim 9 (depends on 1)

The method of claim 1 wherein the isomerization catalyst comprises a zeolite comprising a 10-membered ring AEL framework, AEI framework, AEL framework, AFO framework, AFX framework, ATO framework, BEA framework, CHA framework, FAU framework, FER framework, MEL framework, MFI framework, MOR framework, MRE framework, MTT framework, MWW framework or TON framework or combinations thereof.

### Claim 10 (depends on 1)

The method of claim 1 wherein the isomerization catalyst comprises platinum or nickel tungsten sulfide.

### Claim 11 (depends on 2)

The method of claim 2 wherein the first adsorbent comprises a ZSM or a type X zeolite.

### Claim 12

A method for production of a mono-methyl alkylbenzene product from a natural oil comprising:
deoxygenating the natural oil to form a paraffin stream comprising C9 to C28 carbon chains;
linear selective cracking the paraffin stream in a separate linear selective cracking unit under linear selective cracking conditions in the presence of a linear selective cracking catalyst to form a first stream comprising normal or lightly branched C9 to C14 paraffins, a second stream comprising C14+ paraffins, and a third stream comprising iso paraffins;
isomerizing the first stream under isomerization conditions in the presence of an isomerization catalyst to form an isomerized stream comprising C9 to C14 mono-methyl paraffins;
removing contaminants from the isomerized stream to form a decontaminated stream wherein the contaminants comprise sulfur compounds, or nitrogen compounds, or phosphorous compounds, or oxygenates, or aromatics, or combinations thereof;
dehydrogenating the decontaminated stream to provide a dehydrogenated stream comprising mono-olefins, di-olefins, and aromatics;
selectively hydrogenating the di-olefins in the dehydrogenated stream to form additional mono-olefins, and separating and removing the aromatics from the mono-olefins to form an aromatics stream comprising the aromatics and a mono-olefins stream comprising the mono-olefins;
alkylating benzene with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene;
isolating the alkylbenzenes to provide the alkylbenzene product derived from the natural oil; and
separating the isomerized stream through a first absorption separation system, wherein the mono methyl paraffins in the mixture are preferentially adsorbed by the adsorbent and where the non-mono methyl paraffins remain in the fluid phase before removing the contaminants from the isomerized stream, wherein the adsorbent in the first absorption separation system is divided into a plurality of adsorbent bed zones; or
separating the decontaminated stream through a second absorption separation system, wherein the mono methyl paraffins in the mixture are preferentially adsorbed by the adsorbent and where the non-mono methyl paraffins remain in the fluid phase before dehydrogenating the decontaminated stream, wherein the adsorbent in the second absorption separation system is divided into a plurality of adsorbent bed zones.

### Claim 13 (depends on 12)

The method of claim 12 wherein the isomerized stream comprises a weight ratio of mono-methyl paraffins to normal paraffins of 3 to 60.

### Claim 14 (depends on 12)

The method of claim 12 further comprising:
recycling the second stream comprising C14+ paraffins to the linear selective cracking unit.

### Claim 15 (depends on 12)

The method of claim 12 wherein the linear selective cracking catalyst comprises a ruthenium, or a platinum, or a nickel supported catalyst, or mixtures thereof.

### Claim 16 (depends on 12)

The method of claim 12 wherein the linear selective cracking conditions comprise a temperature in a range of 290° C. to 455° C., or a pressure in a range of 2.8 MPa to 17.5 MPa, or combinations thereof.

### Claim 17 (depends on 12)

The method of claim 12 wherein the isomerization conditions comprise a temperature in a range of 280° C. to 400° C., or a pressure in a range of 2.8 MPa to 17.5 MPa, or 1500-10000 standard cubic foot of hydrogen per barrel of feed, 0.25-2.5 LHSV, or combinations thereof.

### Claim 18 (depends on 12)

The method of claim 12 wherein the isomerization catalyst comprises a zeolite comprising a 10-membered ring AEL framework, AEI framework, AEL framework, AFO framework, AFX framework, ATO framework, BEA framework, CHA framework, FAU framework, FER framework, MEL framework, MFI framework, MOR framework, MRE framework, MTT framework, MWW framework or TON framework or combinations thereof.

### Claim 19 (depends on 12)

The method of claim 12 wherein the isomerization catalyst comprises of EU-2, ZSM-11, ZSM-22, ZSM-23, ZSM-48, SAPO-5, SAPO-11, SAPO-31, SAPO-34, SAPO-41, SSZ-13, SSZ-16, SSZ-39, MCM-22, zeolite Y, ferrierite, mordenite, ZSM-5 or zeolite beta, and combinations thereof.

### Claim 20 (depends on 12)

The method of claim 12 wherein the first adsorbent comprises a ZSM or a type X zeolite.