Processes for producing hydrocarbons from a renewable feedstock

Patent metadata

Field	Value
Publication number	US-10065903-B2
Application number	US-201615220332-A
Country	US
Kind code	B2
Filing date	Jul 26, 2016
Priority date	Jul 31, 2015
Publication date	Sep 4, 2018
Grant date	Sep 4, 2018

Abstract

Processes for the production of linear alkylbenzenes from a renewable feedstock. Prior to converting the side chains of the glycerides and free fatty acids of the feedstock into hydrocarbons, the feedstock is separated into a stream rich in C10 and C14 free fatty acids glycerides having C10 and C14 fatty acid side chains and at least one, preferably two, other glyceride streams. The stream rich in glycerides having C10 and C14 fatty acid side chains can be converted via deoxygenation into a stream rich in C9 to C14 hydrocarbons while the other glyceride streams can be used as vegetable oil. A C10 to C13 hydrocarbon fraction from the stream rich in C9 to C14 hydrocarbons may be dehydrogenated to form olefins which may be reacted with benzene to form linear alkylbenzenes. The linear alkylbenzenes may be used to produce surfactants.

First claim

The invention claimed is:

1. A process for producing a linear mono-olefin hydrocarbon stream for use in producing a linear alkyl benzene product stream, the process comprising:
distilling a renewable feedstock comprising one or more natural oils derived from plant or algae matter in a separation zone to provide a light glyceride stream that includes C 8 and lighter fatty acid side chains, a glyceride stream rich in glycerides with C 10 to C 14 fatty acid side chains, and at least one other glyceride stream;
deoxygenating the glyceride stream rich in glycerides with C 10 to C 14 fatty acid side chains in a deoxygenation zone having a catalyst to provide a paraffin hydrocarbon stream;
dehydrogenating the paraffin hydrocarbon stream in a dehydrogenation zone to provide a linear mono-olefin hydrocarbon stream; and
alkylating the linear mono-olefin hydrocarbon stream with benzene in an alkylation zone having an alkylation catalyst to provide a linear alkyl benzene product stream.

2. The process of claim 1 wherein the separation zone comprises at least one fractionation column.

3. The process of claim 1 wherein the at least one other glyceride stream comprises a heavy glyceride stream that includes one or more C 14 and heavier fatty acid side chains.

4. The process of claim 3 further comprising:
recovering at least one of the heavy glyceride stream and the light glyceride stream to be used as vegetable oil.

5. The process of claim 3 further comprising:
recovering both the heavy glyceride stream and the light glyceride stream to be used as vegetable oil.

6. The process of claim 1 , wherein the renewable feedstock comprises a natural oil rich in glycerides with C 10 to C 14 fatty acid side chains.

7. The process of claim 6 , wherein the natural oil rich in glycerides with C 10 to C 14 fatty acid side chains is selected from the group consisting of: coconut oil; palm kernel oil; laurel oil; babassu oil; microbial oils; and mixtures thereof.

8. The process of claim 1 further comprising:
sulfonating the linear alkyl benzene product stream to provide a surfactant product.

9. A process for producing a linear mono-olefin hydrocarbon stream for use in producing a linear alkyl benzene product stream, the process comprising:
passing a renewable glyceride feedstock to a separation zone;
distilling the renewable glyceride feedstock to provide a light glyceride stream that includes C 8 and lighter fatty acid side chains, a glyceride stream rich in glycerides with C 10 to C 14 fatty acid side chains, and at least one other glyceride stream comprising glycerides that include one or more C 14 and heavier fatty acid side chains;
passing the glyceride stream rich in glycerides with C 10 to C 14 fatty acid side chains to a deoxygenation zone having a catalyst to provide a paraffin hydrocarbon stream;
passing at least a portion of the paraffin hydrocarbon stream to a dehydrogenation zone to provide a linear mono-olefin hydrocarbon stream;
passing the linear mono-olefin hydrocarbon stream and benzene to an alkylation zone having an alkylation catalyst to provide a linear alkyl benzene product stream; and
recovering the light glyceride stream and the at least one other glyceride stream to be used as a vegetable oil.

10. The process of claim 9 further comprising:
sulfonating the linear alkyl benzene product stream to provide a surfactant product.

11. The process of claim 10 , wherein the paraffin hydrocarbon stream comprises C 10 to C 13 hydrocarbons and wherein passing at least a portion of the paraffin hydrocarbon stream to the dehydrogenation zone comprises: separating the paraffin hydrocarbon stream into a C 10 to C 13 hydrocarbon stream and at least one other paraffin stream; and
passing the C 10 to C 13 hydrocarbon stream to the dehydrogenation zone.

12. The process of claim 10 , wherein the renewable glyceride feedstock is selected from the group consisting of: coconut oil; palm kernel oil; laurel oil; babassu oil; microbial oils; and mixtures thereof.

13. The process of claim 10 , wherein the renewable glyceride feedstock comprises an oil rich in glycerides having C 10 to C 14 fatty acid side chains.

14. The process of claim 9 wherein the separation zone comprises a fractionation column.

15. A process for producing a linear mono-olefin hydrocarbon stream for use in producing a linear alkyl benzene product stream, the process comprising:
passing a renewable glyceride feedstock to a separation zone;
distilling the renewable glyceride feedstock to provide a light glyceride stream that includes C 8 and lighter fatty acid side chains, a glyceride stream rich in glycerides with C 10 to C 14 fatty acid side chains, and a heavy glyceride stream;
recovering at least one of the heavy glyceride stream and the light glyceride stream to be used as vegetable oil;
passing the glyceride stream rich in glycerides with C 10 to C 14 fatty acid side chains to a deoxygenation zone having a catalyst to provide a paraffin hydrocarbon stream;
passing at least a portion of the paraffin hydrocarbon stream to a dehydrogenation zone to provide a linear mono-olefin hydrocarbon stream; and
passing the linear mono-olefin hydrocarbon stream and benzene to an alkylation zone having an alkylation catalyst to provide a linear alkyl benzene product stream.

16. The process of claim 15 , wherein the paraffin hydrocarbon stream comprises C 10 to C 13 hydrocarbons and wherein passing at least a portion of the paraffin hydrocarbon stream to the dehydrogenation zone comprises: separating the paraffin hydrocarbon stream into a C 10 to C 13 hydrocarbon stream and at least one other paraffin stream; and
passing the C 10 to C 13 hydrocarbon stream to the dehydrogenation zone.

Assignees

• Uop Llc

Inventors

• Ellig Daniel L
• Fichtl Geoffrey W
• Luebke Charles P

Classifications

• C07C1/2078

  by a transformation in which at least one -C(=O)-O- moiety is eliminated · CPC title

• C07C5/333

  Catalytic processes · CPC title

• C10G57/005

  with alkylation · CPC title

• Y02P30/20

  using bio-feedstock · CPC title

• C11C3/08

  with fatty acids · CPC title