IP Library › Granted Patent US 11,453,623
Granted Patent B2
US 11,453,623 · App. 16/649,506 · Granted Sep 27, 2022

Process for the production of alkylaromatics

Inventor: Daniel R. Weaver (The Woodlands, TX)
Assignee: Indorama Ventures Oxides LLC
C07C2/70B01J19/2435B01J2219/00051C07C15/107
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Quick Facts
Patent No.
US 11,453,623
App. No.
16/649,506
Granted
Sep 27, 2022
Kind
B2
Abstract

The present disclosure describes a process for the production of alkylaromatics that may be performed using a loop reactor comprising the steps of: introducing an alkylatable aromatic compound; introducing an olefin; introducing a catalyst; adjusting the alkylatable aromatic compound to a pre-reaction temperature that is below a desired reaction temperature; optionally, adjusting the olefin to a second pre-reaction temperature that is below the desired reaction temperature; optionally, adjusting the catalyst to a third pre-reaction temperature that is below the desired reaction temperature; initially contacting the catalyst and olefin under conditions to control the temperature of the reaction of the catalyst and olefin; mixing and/or circulating the alkylatable aromatic compound, the olefin and the catalyst; and maintaining the alkylatable aromatic compound and olefin at the desired reaction temperature.

Claims (43)

1. An alkylation process comprising the steps of:

providing a loop reactor comprising a reaction chamber and a heat exchanger, wherein the reaction chamber and the heat exchanger are in fluid communication with each other via at least one conduit such that a fluid in the reaction chamber can be circulated through the heat exchanger and returned to the reaction chamber;

introducing an alkylatable aromatic compound into the loop reactor;

introducing an olefin into the loop reactor;

introducing a catalyst into the loop reactor;

adjusting the alkylatable aromatic compound to a pre-reaction temperature that is below a desired reaction temperature prior to introducing the catalyst;

adjusting the olefin to a second pre-reaction temperature that is below the desired reaction temperature prior to introducing the catalyst;

optionally, adjusting the catalyst to a third pre-reaction temperature that is below the desired reaction temperature;

initially contacting the catalyst and olefin in the conduit circulating fluid from the reaction chamber to the heat exchanger;

circulating the alkylatable aromatic compound, the olefin and the catalyst in the loop reactor; and

maintaining the alkylatable aromatic compound and olefin at the desired reaction temperature after contacting the catalyst and olefin,

wherein adjusting the olefin to a second pre-reaction temperature that is below the desired reaction temperature occurs before the step of initially contacting the catalyst and olefin in the conduit circulating fluid from the reaction chamber to the heat exchanger, and

wherein adjusting the alkylatable aromatic compound to a pre-reaction temperature that is below the desired reaction temperature comprises circulating the alkylatable aromatic compound through the heat exchanger.

2. The process of claim 1 , further comprising mixing the alkylatable aromatic compound, the olefin and the catalyst in the loop reactor.

3. The process of claim 1 , wherein the loop reactor further comprises a pump.

4. The process of claim 1 , wherein adjusting the olefin to a second pre-reaction temperature that is below the desired reaction temperature comprises circulating the olefin through the heat exchanger prior to introducing the catalyst in the loop reactor.

5. The process of claim 1 , wherein the pre-reaction temperature, second pre-reaction temperature and third pre-reaction temperature each comprise temperatures that are about 2 to about 60 degrees Celsius below the desired reaction temperature.

6. The process of claim 1 , wherein introducing the catalyst into the loop reactor comprises adding the catalyst in the conduit circulating fluid from the reaction chamber to the heat exchanger.

7. The process of claim 1 , wherein introducing the olefin into the loop reactor comprises adding the olefin in the conduit circulating fluid from the reaction chamber to the heat exchanger.

8. The process of claim 1 , wherein the process further comprises the steps of:

introducing a diluent into the loop reactor; and

optionally, adjusting the diluent to a fourth pre-reaction temperature that is below a desired reaction temperature.

9. The process of claim 1 , wherein the catalyst is an acid catalyst.

10. The process of claim 9 , wherein the acid catalyst is selected from the group consisting of: hydrofluoric acid, triflic acid, aluminum chloride, boron trifluoride and combinations thereof.

11. The process of claim 1 , wherein the alkylatable aromatic compound is selected from the group consisting of: benzene, xylene, toluene, cumene, ethylbenzene, butylbenzene, naphthalene and combinations thereof.

12. The process of claim 1 , wherein the alkylatable aromatic compound comprises a substituted aromatic compound comprising the formula:

wherein R1 is hydrogen or an alkyl group containing from about 1 to 4 carbon atoms; R2 is hydrogen or an alkyl group having from about 1 to 4 carbon atoms; and R3 is an alkyl group having from about 14 to about 60 carbon atoms.

13. The process of claim 1 , wherein the olefin is at least one C 8 or higher olefin.

14. The process of claim 1 , wherein the olefin is at least one C 14 to C 60 olefin.

15. The process of claim 1 , wherein initially contacting the catalyst and olefin under conditions to control the temperature of the reaction of the catalyst and olefin comprises contacting the catalyst and olefin at a point before the catalyst and olefin pass through the heat exchanger.

16. The process of claim 1 , wherein initially contacting the catalyst and olefin under conditions to control the temperature of the reaction of the catalyst and olefin comprises contacting the catalyst and olefin incrementally over a period of 1 minute to 120 minutes.

17. An alkylation process comprising the steps of:

providing a loop reactor comprising a reaction chamber and a heat exchanger, wherein the reaction chamber and the heat exchanger are in fluid communication with each other via at least one conduit such that a fluid in the reaction chamber can be circulated through the heat exchanger and returned to the reaction chamber;

introducing an alkylatable aromatic compound into the loop reactor;

introducing an olefin into the loop reactor;

introducing a catalyst into the loop reactor;

adjusting the alkylatable aromatic compound to a pre-reaction temperature that is below a desired reaction temperature prior to introducing the catalyst;

adjusting the olefin to a second pre-reaction temperature that is below the desired reaction temperature prior to introducing the catalyst;

optionally, adjusting the catalyst to a third pre-reaction temperature that is below the desired reaction temperature;

initially contacting the catalyst and olefin in the conduit circulating fluid from the reaction chamber to the heat exchanger;

circulating the alkylatable aromatic compound, the olefin and the catalyst in the loop reactor; and

maintaining the alkylatable aromatic compound and olefin at the desired reaction temperature after contacting the catalyst and olefin,

wherein adjusting the olefin to a second pre-reaction temperature that is below the desired reaction temperature comprises circulating the olefin through the heat exchanger prior to introducing the catalyst in the loop reactor and occurs before the step of initially contacting the catalyst and olefin in the conduit circulating fluid from the reaction chamber to the heat exchanger.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2020
From: WEAVER, DANIEL R.
To: HUNTSMAN PETROCHEMICAL LLC
Reel/Frame 052181/0331 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2020
From: HUNTSMAN PETROCHEMICAL LLC
To: INDORAMA VENTURES OXIDES LLC
Reel/Frame 052202/0119 →
Continuity (2)
Provisional Application 62561924 · Sep 22, 2017
Related Publication 20200247729A1 · Aug 6, 2020
Cited By (1)
US 12,240,792