Linear alkylbenzenes from natural oils and methods of producing

Patent metadata

Field	Value
Publication number	US-9079811-B2
Application number	US-201414297827-A
Country	US
Kind code	B2
Filing date	Jun 6, 2014
Priority date	Jun 10, 2013
Publication date	Jul 14, 2015
Grant date	Jul 14, 2015

Abstract

A linear alkyl benzene product and production of linear alkylbenzene from a natural oil are provided. A method comprises the step of deoxygenating the natural oils to form a stream comprising paraffins. The paraffins are dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product.

First claim

What is claimed is:

1. A method for generating an alkylbenzene product from a natural oil comprising:
deoxygenating the natural oil selected from the group consisting of palm kernel oil, coconut oil, babassu oil, and mixtures thereof to form a stream comprising paraffins, wherein the deoxygenating utilizes a catalyst comprising a first component selected from the group consisting of Ni—Mo, Ni—Mo—P, Ni—Co—Mo, and Co—Mo and a second component selected from the group consisting of aluminas, silica, titania, zirconia, and mixtures thereof;
dehydrogenating at least a portion of the paraffins to provide mono-olefins;
alkylating benzene with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene;
separating the alkylbenzenes to provide the alkylbenzene product comprising alkylbenzenes having an alkyl group of about n carbon atoms where n is from about 12 to about 13 and wherein the alkyl group is a linear alkyl group for at least 80 mass % of the alkylbenzenes having an alkyl group of about n atoms.

2. The method of claim 1 further comprising, sulfonating the alkylbenzene product to form a linear alkylbenzene sulfonate product.

3. The method of claim 1 wherein a hydrogen stream results from dehydrogenating the paraffins, and wherein the method further comprises recycling the hydrogen stream to the deoxygenating step.

4. The method of claim 1 further comprising separating a second portion of paraffins from the stream comprising paraffins, and isomerizing the second portion of paraffins to form isoparaffins.

5. The method of claim 1 wherein di-olefins are also generated by dehydrogenating the paraffins, and wherein the method further comprises selectively hydrogenating the di-olefins to form additional mono-olefins.

6. The method of claim 1 wherein aromatics are also generated by dehydrogenating the paraffins, the method further comprising removing aromatics from the mono-olefins before alkylating.

7. A method for generating an alkylbenzene product from a natural oil comprising:
deoxygenating the natural oil selected from the group consisting of palm kernel oil, coconut oil, babassu oil, and mixtures thereof to form a stream comprising paraffins, wherein the deoxygenating utilizes a catalyst comprising a first component selected from the group consisting of Ni—Mo, Ni—Mo—P, Ni—Co—Mo, and Co—Mo and a second component selected from the group consisting of aluminas, silica, titania, zirconia, and mixtures thereof;
dehydrogenating at least a portion of the paraffins to provide mono-olefins;
alkylating benzene with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene;
separating the alkylbenzenes to provide the alkylbenzene product comprising alkylbenzenes having an alkyl group of about n carbon atoms where n is from about 8 to about 15 and wherein the alkyl group is a linear alkyl group for at least 80 mass % of the alkylbenzenes having an alkyl group of about n atoms.

8. A method for generating an alkylbenzene product from a natural oil comprising:
deoxygenating the natural oil selected from the group consisting of palm kernel oil, coconut oil, babassu oil, and mixtures thereof to form a stream comprising paraffins, wherein the deoxygenating utilizes a catalyst comprising a first component selected from the group consisting of Ni—Mo, Ni—Mo—P, Ni—Co—Mo, and Co—Mo and a second component selected from the group consisting of aluminas, silica, titania, zirconia, and mixtures thereof;
dehydrogenating at least a portion of the paraffins to provide mono-olefins;
alkylating benzene with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene;
separating the alkylbenzenes to provide the alkylbenzene product comprising alkylbenzenes having an alkyl group of about n carbon atoms where n is from about 10 to about 13 and wherein the alkyl group is a linear alkyl group for at least 80 mass % of the alkylbenzenes having an alkyl group of about n atoms.

9. A method for generating an alkylbenzene product from a natural oil comprising:
deoxygenating the natural oil selected from the group consisting of palm kernel oil, coconut oil, babassu oil, and mixtures thereof to form a stream comprising paraffins, wherein the deoxygenating utilizes a catalyst comprising a first component selected from the group consisting of Ni—Mo, Ni—Mo—P, Ni—Co—Mo, and Co—Mo and a second component selected from the group consisting of aluminas, silica, titania, zirconia, and mixtures thereof;
dehydrogenating at least a portion of the paraffins to provide mono-olefins;
alkylating benzene with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene;
separating the alkylbenzenes to provide the alkylbenzene product comprising alkylbenzenes having an alkyl group of about n carbon atoms where n is from about 9 to about 14 and wherein the alkyl group is a linear alkyl group for at least 80 mass % of the alkylbenzenes having an alkyl group of about n atoms.

Assignees

• Uop Llc

Inventors

• Frey Stanley J
• Ellig Daniel L
• Bozzano Andrea G
• Fichtl Geoffrey W
• Majumder Debarshi

Classifications

• C11D1/22 Primary

  derived from aromatic compounds · CPC title

• C07C303/02

  of sulfonic acids or halides thereof · CPC title

• C07C1/22 Primary

  by reduction · CPC title

• C07C2101/16

  Chemistry & Metallurgy · mapped topic

• C11D3/3418

  Toluene -, xylene -, cumene -, benzene - or naphthalene sulfonates or sulfates · CPC title