Transalkylation process

Patent metadata

Field	Value
Publication number	US-10781149-B2
Application number	US-201514941720-A
Country	US
Kind code	B2
Filing date	Nov 16, 2015
Priority date	Dec 19, 2014
Publication date	Sep 22, 2020
Grant date	Sep 22, 2020

Abstract

Disclosed is a transalkylation process for making an aromatic material between a light aromatic material and a heavier aromatic material in the presence of hydrogen and a transalkylation catalyst comprising a hydrogenation component and a transalkylation component. The process comprises conducting the transalkylation reaction under conditions conducive to reducing the amount of cyclic compounds in the transalkylation reaction mixture in the beginning phase of the operation that is different from the conditions after the beginning phase. The invention is useful, e.g., in transalkylation between toluene and C9+ aromatic feed materials to produce xylenes and/or benzene.

First claim

The invention claimed is:

1. A transalkylation process comprising:
supplying a feedstream to the transalkylation reactor, wherein the feedstream comprises toluene, C9 aromatic material, and C10 aromatic material; and
conducting a transalkylation reaction with the feedstream in the presence of a transalkylation catalyst under transalkylation conditions to produce a transalkylation reaction product mixture comprising at least one alicyclic compound,
wherein:
the transalkylation catalyst comprises a hydrogenation metal component;
in the first set of transalkylation conditions, the feedstream has a first ratio of the weight of the toluene to the total weight of the toluene, the C9 aromatic material, and the C10 aromatic material;
in the second set of transalkylation conditions, the feedstream has a second ratio of the weight of the toluene to the total weight of the toluene, the C9 aromatic material, and the C10 aromatic material; and
the first ratio divided by the second ratio is between 1.5 and 3.0, such that ring-loss is reduced in the transalkylation process compared to a transalkylation process operated under the second set of transalkylation conditions only.

2. The process of claim 1 , wherein the at least one alicyclic compound is a saturated alicyclic compound.

3. The process of claim 1 , wherein the at least one alicyclic compound is selected from cyclopentane, methylcyclopentane, ethylcyclopentane, dimethylcyclopentanes, trimethylcyclopentanes, methylethylcyclopentanes, propylcyclopentanes, cyclohexane, methylcyclohexane, dimethylcyclohexanes, trimethylcyclohexanes, methylethylcyclohexanes, propylcyclohexanes, cycloheptane, methylcycloheptane, dimethylcycloheptanes, ethylcycloheptane, methylethylcycloheptanes, trimethylcycloheptanes, cyclopentene, alkyl substituted cyclopentenes, cyclohexene, alkyl substituted cyclohexenes, and combinations of two or more thereof.

4. The process of claim 1 , wherein the transalkylation conditions favor cracking reactions of C5 to C8 alicyclic compounds to form paraffins during the first set of transalkylation conditions.

5. The process of claim 1 , wherein at least a portion of the toluene is generated in situ.

6. The process of claim 1 , wherein the transalkylation catalyst further comprises a solid acid.

7. The process of claim 6 , wherein the solid acid is an aluminosilicate molecular sieve selected from the following framework types: CHA, EMT, ERI, EUO, FAU, FER, HEU, KFI, LEV, LTA, MAZ, MEI, MEL, MFI, MTT, MTW, MWW, TON, and mixtures and combinations thereof.

8. The process of claim 1 , wherein the hydrogenation component comprises at least one of nickel, rhodium, palladium, ruthenium, rhenium, osmium, iridium, and platinum.

9. The process of claim 1 , wherein the transalkylation reaction product mixture comprises benzene, para-xylene, meta-xylene, ortho-xylene, and toluene.

10. The process of claim 1 , wherein:
the transalkylation reaction is conducted under a first hydrogen partial pressure of PH2a in the first set of transalkylation conditions;
the transalkylation reaction is conducted under a second hydrogen partial pressure of PH2b in the second set of transalkylation conditions; and
PH 2 a<PH 2 b , and 0.10 PH 2 a/PH 2 b≤ 0.95.

11. The process of claim 1 , wherein:
the transalkylation reaction is conducted under a first total internal pressure of Pip1 in the first set of transalkylation conditions;
the transalkylation reaction is conducted under a second total internal pressure of Pip2 in the second set of transalkylation conditions; and
Pip 1< Pip 2, and 0.10≤ Pip 1/ Pip 2≤0.95.

12. The process of claim 1 , wherein the transalkylation catalyst comprises a first molecular sieve in a first catalyst bed and a second molecular sieve in a second catalyst bed; and
wherein conducting the transalkylation reaction comprises:
supplying the feedstream to the first molecular sieve to produce a first effluent; and
supplying the first effluent to the second molecular sieve.

13. The process of claim 12 , wherein the first molecular sieve comprises ZSM-5 and the second molecular sieve comprises ZSM-12.

14. The process of claim 13 , wherein the ZSM-5 has a silica to alumina ratio of 10-100 and the ZSM-12 has a silica to alumina ratio of 50-300.

15. A transalkylation process comprising:
supplying a first feed comprising toluene to a transalkylation reactor;
supplying a second feed comprising a C9 aromatic material and a C10 aromatic material to the transalkylation reactor; and
conducting a transalkylation reaction between the first feed and the second feed in the presence of a transalkylation catalyst comprising an aluminosilicate molecular sieve and a hydrogenation metal component under transalkylation conditions to produce a transalkylation reaction product mixture comprising at least one alicyclic compound,
wherein the transalkylation reaction is conducted under a first set of transalkylation conditions in a beginning phase of a transalkylation reactor operation cycle and a second set of transalkylation conditions after the beginning phase of the operation cycle;
wherein the first set of transalkylation conditions comprises a first ratio of the weight of the toluene to a total weight of the toluene, the C9 aromatic material, and the C10 aromatic material;
wherein the second set of transalkylation conditions comprises a second ratio of the weight of the toluene to the total weight of the toluene, the C9 aromatic material, and the C10 aromatic material; and
wherein the first ratio divided by the second ratio is between 1.5 and 3.0, such that ring-loss is reduced in the transalkylation process compared to a transalkylation process operated under the second set of transalkylation conditions only.

16. The process of claim 15 , wherein the aluminosilicate molecular sieve comprises a first molecular sieve in a first catalyst bed and a second molecular sieve in a second catalyst bed; and
wherein conducting the transalkylation reaction comprises:
supplying the first feed and the second feed to the first molecular sieve to produce a first effluent; and
supplying the first effluent to the second molecular sieve.

17. The process of claim 16 , wherein the first molecular sieve comprises ZSM-5 and the second molecular sieve comprises ZSM-12.

18. The process of claim 17 , wherein the ZSM-5 has a silica to alumina ratio of 10-100 and the ZSM-12 has a silica to alumina ratio of 50-300.

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Molinier Michel
• Andrews Jeffrey L
• Nair Hari

Classifications

• C07C2529/12

  Noble metals · CPC title

• C07C6/126 Primary

  of more than one hydrocarbon · CPC title

• C10G29/205

  by reaction with hydrocarbons added to the hydrocarbon oil · CPC title

• C07C2529/74

  Noble metals · CPC title

• C10G2300/1096

  Aromatics or polyaromatics · CPC title