Benzene alkylation using acidic ionic liquids

Patent metadata

Field	Value
Publication number	US-9328037-B2
Application number	US-201414327185-A
Country	US
Kind code	B2
Filing date	Jul 9, 2014
Priority date	Jul 9, 2014
Publication date	May 3, 2016
Grant date	May 3, 2016

Abstract

A process for making linear alkyl aromatics is described. The process involves preparing the paraffin feed by dehydrogenating normal paraffins, selectively hydrogenating any diolefins, and adsorbing any aromatics to form an olefin feed. The olefin feed is contacted with an aromatic feed in the presence of an ionic liquid catalyst to form a mixture of alkylated aromatics. The ionic liquid catalyst is separated from the mixture of alkylated aromatics by gravity, and any ionic liquid retained in the alkylated aromatics is removed by adsorption or extraction. The mixture of alkylated aromatics is then separated into monoalkylated aromatics and dialkylated aromatics.

First claim

What is claimed is:

1. A process for making linear alkyl aromatics comprising:
dehydrogenating normal paraffins in a dehydrogenation zone to form a stream comprising C 6 to C 30 olefins;
selectively hydrogenating diolefins in the stream comprising olefins in a selective hydrogenation zone to form a stream comprising normal olefins;
adsorbing aromatics from the stream comprising normal olefins in an aromatics adsorption unit to form a stream comprising olefins having a lower aromatic content;
contacting an aromatic feed and the stream comprising olefins having the lower aromatic content in the presence of an ionic liquid catalyst in an alkylation reaction zone under alkylating conditions to form a product mixture comprising a mixture of alkylated aromatics comprising monoalkylated aromatics and dialkylated aromatics, the mixture of alkylated aromatics comprising greater than 90% linear alkylated aromatics, wherein a volume ratio of ionic liquid catalyst to hydrocarbon is in a range of 0.05:1 to 2.0:1, the hydrocarbon comprising the aromatic feed and the alkylating agent, and wherein a molar ratio of the aromatic feed to the olefin is in a range of 4:1 to 8:1; wherein the ionic liquid catalyst comprises at least one of 1-Butyl-3-methylimidazolium AlCl 4 , 1-butyl-3-methylimidazolium Al 2 Cl 7 , 1-hexyl-3-methylimidazolium AlCl 4 , and 1-hexyl-3-methylimidazolium Al 2 Cl 7 ; and wherein a ratio of monoalkylated benzene to total alkylated product is greater than 0.95;
separating the ionic liquid catalyst from the product mixture by gravity into an ionic liquid catalyst stream and a product mixture stream;
removing any retained ionic liquid catalyst from the product mixture stream by adsorption or extraction; and
separating the product mixture stream into a stream comprising the monoalkylated aromatics and a stream comprising the dialkylated aromatics.

2. The process of claim 1 wherein the aromatic feed comprises benzene.

3. The process of claim 1 wherein the volume ratio of the ionic liquid catalyst to the hydrocarbon is in the range of 1:1 to 1.5:1.

4. The process of claim 1 wherein the aromatic feed comprises benzene, the olefin comprises C 9 to C 14 olefins, the mixture of alkylated aromatics comprises alkylated benzene, and wherein a selectivity for linear alkylated benzene is greater than 96%.

5. The process of claim 1 wherein the alkylating conditions include a temperature of from about 0° C. to about 80° C., and a pressure of from about 0.1 MPa to about 5 MPa.

6. The process of claim 1 further comprising regenerating the ionic liquid catalyst.

7. The process of claim 1 wherein removing any retained ionic liquid catalyst from the product mixture stream by adsorption or extraction comprises removing any retained ionic liquid catalyst from the product mixture stream comprising by extraction using a polar solvent.

8. The process of claim 1 wherein the product mixture further comprises unreacted aromatic feed, and unreacted normal paraffins, and wherein separating the product mixture stream into the stream comprising the monoalkylated aromatics and the stream comprising the dialkylated aromatics comprises separating the product mixture stream into a stream comprising the unreacted aromatic feed, a stream comprising the unreacted paraffins, the stream comprising the monoalkylated aromatics, and the stream comprising the dialkylated aromatics.

9. The process of claim 8 further comprising at least one of:
recycling the unreacted aromatic feed stream to the alkylation reaction zone; and
recycling the unreacted paraffins stream to the dehydrogenation zone.

10. The process of claim 1 wherein contacting the aromatic feed and the stream comprising olefins having the lower aromatic content in the presence of the ionic liquid catalyst in the alkylation reaction zone comprises contacting the aromatic feed and the stream comprising olefins having the lower aromatic content in the presence of the ionic liquid catalyst and an acid or acid precursor in the alkylation reaction zone.

11. An alkylation process comprising:
contacting benzene and an alkylating agent comprising an olefin C 6 to C 30 olefins in the presence of a halometallate ionic liquid catalyst in an alkylation reaction zone under alkylating conditions to form a product mixture comprising a mixture of alkylated benzene, unreacted benzene, and unreacted alkylating agent, the mixture of alkylated benzene comprising greater than 90% linear alkylated benzene, wherein the ionic liquid catalyst comprises at least one of 1-Butyl-3-methylimidazolium AlCl 4 , 1-butyl-3-methylimidazolium Al 2 Cl 7 , 1-hexyl-3-methylimidazolium AlCl 4 , and 1-hexyl-3-methylimidazolium Al 2 Cl 7 ;
wherein a volume ratio of ionic liquid catalyst to hydrocarbon is in a range of 0.05:1 to 2.0:1, the hydrocarbon comprising the benzene and the alkylating agent;
wherein a molar ratio of the benzene to the olefin is in a range of 4:1 to 8:1;
wherein a ratio of monoalkylated benzene to total alkylated product is greater than 0.95;
separating the halometallate ionic liquid catalyst from the product mixture by gravity into an ionic liquid catalyst stream and a stream of the product mixture;
removing any retained ionic liquid catalyst from the product mixture stream by adsorption or extraction;
separating the product mixture stream into a stream comprising the monoalkylated benzene, a stream comprising the dialkylated benzene, a stream comprising the unreacted benzene, and a stream comprising the unreacted alkylating agent;
recycling the unreacted benzene stream to the alkylation reaction zone; and
recycling the unreacted alkylating agent stream to a dehydrogenation zone.

12. The process of claim 11 wherein the volume ratio of the ionic liquid catalyst to the hydrocarbon is in the range of 1:1 to 1.5:1.

13. The process of claim 12 wherein removing any retained ionic liquid catalyst from the product mixture stream comprises removing any retained ionic liquid catalyst from the product mixture stream by extraction using a polar solvent.

Assignees

• Uop Llc
• Boreskova Inst Kataliza Sibir

Inventors

• Riley Mark G
• Bhattacharyya Alakananda
• Adonin Nikolay Yu
• Timofeeva Mariya N
• Prikhodko Sergey A
• Bal Zhinimaev Bair S

Classifications

• C07C2/66 Primary

  Catalytic processes · CPC title

• C07C2527/24

  Nitrogen compounds · CPC title

• C07C2527/14

  Phosphorus; Compounds thereof · CPC title

• C07C2/68 Primary

  with halides · CPC title

• C07C5/327

  Formation of non-aromatic carbon-to-carbon double bonds only · CPC title