Aromatic hydrogenation catalysts and uses thereof

Patent metadata

Field	Value
Publication number	US-10047304-B2
Application number	US-201514966071-A
Country	US
Kind code	B2
Filing date	Dec 11, 2015
Priority date	Dec 12, 2014
Publication date	Aug 14, 2018
Grant date	Aug 14, 2018

Abstract

Hydrogenation catalysts for aromatic hydrogenation including an organosilica material support, which is a polymer comprising independent units of a monomer of Formula [Z1OZ2OSiCH2]3 (I), wherein each Z1 and Z2 independently represent a hydrogen atom, a C1-C4 alkyl group or a bond to a silicon atom of another monomer; and at least one catalyst metal are provided herein. Methods of making the hydrogenation catalysts and processes of using, e.g., aromatic hydrogenation, the hydrogenation catalyst are also provided herein.

First claim

What is claimed is:

1. An aromatics hydrogenation process for a hydrocarbon feedstream comprising:
a) contacting a hydrocarbon feedstream comprising aromatics with a hydrogenation catalyst in the presence of a hydrogen-containing treat gas in a reaction stage operated under effective aromatics hydrogenation conditions to produce a reaction product with reduced aromatics content,
wherein the hydrogenation catalyst comprises:
(i) an organosilica material support, which is a polymer comprising independent units of a monomer of Formula [Z 1 OZ 2 OSiCH 2 ] 3 (I), wherein each Z 1 and Z 2 independently represent a hydrogen atom, a C 1 -C 4 alkyl group or a bond to a silicon atom of another monomer, wherein the organosilica material support has an X-ray diffraction pattern with one peak between 1 and 3 degrees 2θ and no peaks in the range of from 3 to 20 degrees 2θ; and
(ii) at least one catalyst metal selected from the group consisting of a Group 8 metal, a Group 9 metal, a Group 10 metal and a combination thereof.

2. The process of claim 1 , wherein each Z 1 and Z 2 independently represent a hydrogen atom, a C 1 -C 2 alkyl group or a bond to a silicon atom of another monomer.

3. The process of claim 2 , wherein each Z 1 and Z 2 independently represent a hydrogen atom, ethyl or a bond to a silicon atom of another monomer.

4. The process of claim 1 , wherein the organosilica material support further comprises at least one other monomer selected from the group consisting of:
(i) at least one independent unit of Formula [Z 3 OZ 4 SiCH 2 ] 3 (II), wherein each Z 3 represents a hydrogen atom, a C 1 -C 4 alkyl group or a bond to a silicon atom of another monomer and each Z 4 represents a C 1 -C 6 alkyl group;
(ii) at least one independent unit of Formula Z 5 OZ 6 Z 7 Z 8 Si (III), wherein each Z 5 represents a hydrogen atom or a C 1 -C 4 alkyl group or a bond to a silicon atom of another monomer; and Z 6 , Z 7 and Z 8 are each independently selected from the group consisting of a hydroxyl group, a C 1 -C 4 alkyl group, a C 1 -C 4 alkoxy group, a nitrogen-containing C 1 -C 10 alkyl group, a nitrogen-containing heteroalkyl group, a nitrogen-containing optionally substituted heterocycloalkyl group and an oxygen atom bonded to a silicon atom of another monomer;
(iii) at least one independent unit of Formula Z 9 Z 10 Z 11 Si—R—SiZ 9 Z 10 Z 11 (IV), wherein each Z 9 independently represents a hydroxyl group, a C 1 -C 4 alkoxy group or an oxygen bonded to a silicon atom of another comonomer; each Z 10 and Z 11 independently represent a hydroxyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 alkyl group or an oxygen bonded to a silicon atom of another monomer; and R is selected from the group consisting a C 1 -C 8 alkylene group, a C 2 -C 8 alkenylene group, a C 2 -C 8 alkynylene group, a nitrogen-containing C 1 -C 10 alkylene group, an optionally substituted C 6 -C 20 aralkyl and an optionally substituted C 4 -C 20 heterocycloalkyl group;
(iv) at least one independent unit of Formula M 1 (OZ 12 ) 3 (V), wherein M 1 represents a Group 13 metal and each Z 12 independently represents a hydrogen atom, a C 1 -C 6 alkyl or a bond to a silicon atom of another monomer;
(v) at least one independent unit of Formula (Z 13 O) 2 M 2 -O—Si(OZ 14 ) 3 (VI), wherein M 2 represents a Group 13 metal and each Z 13 and each Z 14 independently represent a hydrogen atom, a C 1 -C 6 alkyl group or a bond to a silicon atom of another monomer; and
(vi) a combination thereof.

5. The process of claim 4 , wherein at least one independent unit of Formula (II) is present, wherein each Z 3 represents a hydrogen atom, a C 1 -C 2 alkyl group or a bond to a silicon atom of another siloxane monomer and each Z 4 represents a C 1 -C 2 alkyl group.

6. The process of claim 5 , wherein each Z 3 represents a hydrogen atom, ethyl or a bond to a silicon atom of another siloxane monomer and each Z 4 represents a methyl.

7. The process of claim 4 , wherein at least one independent unit of Formula (III) is present, wherein each Z 5 represents a hydrogen atom, a C 1 -C 2 alkyl group or a bond to a silicon atom of another comonomer; and Z 6 , Z 7 and Z 8 are each independently selected from the group consisting of a hydroxyl group, a C 1 -C 2 alkyl group, C 1 -C 2 alkoxy group, a nitrogen-containing C 3 -C 10 alkyl group, a nitrogen-containing C 4 -C 10 heteroalkyl group, a nitrogen-containing optionally substituted C 4 -C 10 heterocycloalkyl group and an oxygen bonded to a silicon atom of another monomer.

8. The process of claim 7 , wherein Z 6 , Z 7 and Z 8 are each independently selected from the group consisting of a hydroxyl group, a C 1 -C 2 alkyl group, C 1 -C 2 alkoxy group, and an oxygen bonded to a silicon atom of another monomer.

9. The process of claim 7 , wherein each Z 5 represents a hydrogen atom, methyl, ethyl, or a bond to a silicon atom of another comonomer; and Z 6 , Z 7 and Z 8 are each independently selected from the group consisting of a hydroxyl group, methyl, methoxy, ethoxy,

and an oxygen bonded to a silicon atom of another monomer.

10. The process of claim 4 , wherein at least one independent unit of Formula (IV) is present, wherein each Z 9 represents a hydroxyl group, a C 1 -C 2 alkoxy group or an oxygen bonded to a silicon atom of another comonomer; each Z 10 and Z 11 independently represent a hydroxyl group, a C 1 -C 2 alkoxy group, a C 1 -C 2 alkyl group or an oxygen bonded to a silicon atom of another monomer; and R is selected from the group consisting of a C 1 -C 4 alkylene group, a C 2 -C 4 alkenylene group, a C 2 -C 4 alkynylene group, a nitrogen-containing C 4 -C 10 alkylene group, an optionally substituted C 6 -C 10 aralkyl and an optionally substituted C 4 -C 12 heterocycloalkyl group.

11. The process of claim 10 , wherein each Z 9 represents a hydroxyl group, methoxy, ethoxy or an oxygen bonded to a silicon atom of another comonomer; each Z 10 and Z 11 independently represent a hydroxyl group, methoxy, ethoxy, methyl or an oxygen bonded to a silicon atom of another monomer; and R is selected from the group consisting of

12. The process of claim 4 , wherein at least one independent unit of Formula (V) is present, wherein M 1 is Al or B and each Z 12 represents a hydrogen atom, a C 1 -C 4 alkyl group or a bond to a silicon atom or another monomer.

13. The process of claim 4 , wherein at least one unit of Formula (VI) is present, wherein M 2 is Al or B and each Z 13 and each Z 14 independently represent a hydrogen atom, a C 1 -C 4 alkyl group or a bond to a silicon atom of another monomer.

14. The process of claim 1 , wherein the organosilica material support has a total surface area of about 500 m 2 /g to about 2000 m 2 /g.

15. The process of claim 1 , wherein the organosilica material support has a pore volume of about 0.5 cm 3 /g to about 3.0 cm 3 /g.

16. The process of claim 1 , wherein the organosilica material support has an average pore diameter of 2.5 nm to 5 nm.

17. The process of claim 1 , wherein the at least one catalyst metal is selected from the group consisting of Pt, Pd, Ir, Rh, Re, Ru, Os and a combination thereof.

18. The process of claim 17 , wherein the at least one catalyst metal is selected from the group consisting of Pt, Pd, and a mixture thereof.

19. The

Assignees

• Podsiadlo Paul
• Li Quanchang
• Calabro David Charles
• Beeckman Jean Willem Lodewijk
• Zhang Lei
• Benitez Kiara M
• Ide Matthew Scott
• Mccarthy Stephen John
• Afeworki Mobae
• Weston Simon Christopher
• Kamakoti Preeti
• Shah Matu J
• Lai Wenyih Frank
• Nines Meghan
• Griffin David A
• Johnson Ivy D
• Exxonmobil Res & Eng Co

Inventors

• Podsiadlo Paul
• Li Quanchang
• Calabro David Charles
• Beeckman Jean Willem Lodewijk
• Zhang Lei
• Benitez Kiara M
• Ide Matthew Scott
• Mccarthy Stephen John
• Afeworki Mobae
• Weston Simon Christopher
• Kamakoti Preeti
• Shah Matu J
• Lai Wenyih Frank
• Nines Meghan
• Griffin David A
• Johnson Ivy D

Classifications

• C01B39/00

  Compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites; Their preparation; After-treatment, e.g. ion-exchange or dealumination (treatment to modify the sorption properties, e.g. shaping using a binder, B01J20/10; treatment to modify the catalytic properties, e.g. combination of treatments to make the zeolites appropriate to their use as a catalyst, B01J29/04; treatment to improve the ion-exchange properties B01J39/14) · CPC title

• B01J2231/646

  of aromatic or heteroaromatic rings · CPC title

• B01J2231/645

  of C=C or C-C triple bonds · CPC title

• B01J37/0207 Primary

  Pretreatment of the support · CPC title

• B01J37/0201

  Impregnation · CPC title