Aromatic hydrogenation catalysts and uses thereof

• US 10,661,262 B2
• Filed: 07/10/2018
• Issued: 05/26/2020
• Est. Priority Date: 12/12/2014
• Status: Active Grant

• Current Assignee: ExxonMobil Research & Engineering Company (Exxon Mobil Corporation)
• Original Assignee: ExxonMobil Research & Engineering Company (Exxon Mobil Corporation)
• 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, Kochersperger, Meghan, Griffin, David A., Johnson, Ivy D.
• Primary Examiner(s): Robinson, Renee
• Application Number:
  US16/031,449
• Publication Number:
  US 20180318790A1
• Time in Patent Office: 686 Days
• CPC Class Codes: B01D 15/00 Separating processes involving the treatment of liquids with solid sorbents using liquid sorbents B01D11/00; ion exchange processes or materials, sorbent materials in general B01J, e.g. sorbents for chromatography B01J20/281; for investigating or analysing materials G01N30/00; Apparatus therefor
• CPC Class Codes: B01J 20/06 comprising oxides or hydroxides of metals not provided for in group B01J20/04
• CPC Class Codes: B01J 20/08 comprising aluminium oxide or hydroxide; comprising bauxite
• CPC Class Codes: B01J 20/10 comprising silica or silicate
• CPC Class Codes: B01J 20/223 containing metals, e.g. organo-metallic compounds, coordination complexes
• CPC Class Codes: B01J 20/226 Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF] preparation of metal complexes containing carboxylic acid moieties C07C51/418; MOF's per se C07F
• CPC Class Codes: B01J 20/264 derived from different types of monomers, e.g. linear or branched copolymers, block copolymers, graft copolymers
• CPC Class Codes: B01J 20/28011 Other properties, e.g. density, crush strength
• CPC Class Codes: B01J 20/28057 Surface area, e.g. B.E.T specific surface area
• CPC Class Codes: B01J 20/28069 Pore volume, e.g. total pore volume, mesopore volume, micropore volume
• CPC Class Codes: B01J 20/28078 Pore diameter
• CPC Class Codes: B01J 20/286 Phases chemically bonded to a substrate, e.g. to silica or to polymers
• CPC Class Codes: B01J 20/3042 Use of binding agents; addition of materials ameliorating the mechanical properties of the produced sorbent
• CPC Class Codes: B01J 20/3236 containing metal, other than zeolites, e.g. oxides, hydroxides, sulphides or salts
• CPC Class Codes: B01J 20/3238 containing any type of zeolite
• CPC Class Codes: B01J 2220/86 Sorbents applied to inner surfaces of columns or capillaries
• CPC Class Codes: B01J 2231/641 Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
• CPC Class Codes: B01J 2231/645 of C=C or C-C triple bonds
• CPC Class Codes: B01J 2231/646 of aromatic or heteroaromatic rings
• CPC Class Codes: B01J 23/42 Platinum
• CPC Class Codes: B01J 23/44 : Palladium
• CPC Class Codes: B01J 31/0274 : containing silicon ligands in coordination complexes B01J31/1608
• CPC Class Codes: B01J 31/125 : Cyclic siloxanes
• CPC Class Codes: B01J 31/127 : the siloxane units, e.g. silsesquioxane units, being grafted onto other polymers or inorganic supports, e.g. via an organic linker
• CPC Class Codes: B01J 35/615 : 100-500 m2/g
• CPC Class Codes: B01J 35/617 : 500-1000 m2/g
• CPC Class Codes: B01J 35/618 : more than 1000 m2/g
• CPC Class Codes: B01J 35/647 : 2-50 nm
• CPC Class Codes: B01J 37/0201 : Impregnation
• CPC Class Codes: B01J 37/0207 : Pretreatment of the support
• CPC Class Codes: B01J 37/0213 : Preparation of the impregnating solution
• CPC Class Codes: B01J 37/0236 : Drying, e.g. preparing a suspension, adding a soluble salt and drying
• CPC Class Codes: B01J 37/036 : to form a gel or a cogel
• CPC Class Codes: B01J 37/04 : Mixing B01J37/0009, B01J37/0018 take precedence
• CPC Class Codes: C01B 37/00 : Compounds having molecular sieve properties but not having base-exchange properties
• CPC Class Codes: C01B 39/00 : 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 Class Codes: C07F 7/08 : Compounds having one or more C—Si linkages
• CPC Class Codes: C07F 7/0807 : comprising Si as a ring atom
• CPC Class Codes: C07F 7/081 : comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• CPC Class Codes: C08F 2/10 : Aqueous solvent
• CPC Class Codes: C08F 210/02 : Ethene
• CPC Class Codes: C08F 210/14 : Monomers containing five or more carbon atoms
• CPC Class Codes: C08F 4/027 : Polymers
• CPC Class Codes: C08F 4/64013 : NN
• CPC Class Codes: C08F 4/64048 : NO
• CPC Class Codes: C08F 4/64089 : NNN
• CPC Class Codes: C08F 4/64148 : NN(R)N
• CPC Class Codes: C08F 4/64158 : ONO
• CPC Class Codes: C08F 4/64189 : ONNO
• CPC Class Codes: C08F 4/64193 : OOOO
• CPC Class Codes: C08F 4/65916 : supported on a carrier, e.g. silica, MgCl2, polymer
• CPC Class Codes: C08G 77/60 : in which all the silicon atoms are connected by linkages other than oxygen atoms
• CPC Class Codes: C10G 25/003 : Specific sorbent material, not covered by C10G25/02 or C10G25/03
• CPC Class Codes: C10G 45/44 : Hydrogenation of the aromatic hydrocarbons
• CPC Class Codes: C10G 45/46 : characterised by the catalyst used
• CPC Class Codes: C10G 45/52 : containing platinum group metals or compounds thereof
• CPC Class Codes: C10M 101/02 : Petroleum fractions
• CPC Class Codes: Y02C 20/20 : of methane

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.

Claims

1. A method of making a hydrogenation catalyst for aromatic hydrogenation, the method comprising:

a) providing an aqueous mixture that contains no structure directing agent and/or porogen,

(b) adding at least one compound of Formula [Z¹⁵Z¹⁶SiCH₂]₃ (VII) into the aqueous mixture to form a solution, wherein each Z¹⁵ represents a C₁-C₄ alkoxy group and each Z¹⁶ represents a C₁-C₄ alkoxy group or a C₁-C₄ alkyl group;

(c) aging the solution to produce a pre-product;

(d) drying the pre-product to obtain 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, 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

(e) impregnating the organosilica material support with 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 method of claim 1, wherein each Z¹⁵ represents a C₁-C₂ alkoxy group.

3. The method of claim 2, wherein each Z¹⁶ represents a C₁-C₄ alkoxy group.

4. The method of claim 3, wherein each Z¹⁶ represents a C₁-C₂ alkoxy group.

5. The method of claim 1, wherein the at least one compound of Formula (VII) is 1,1,3,3,5,5-hexaethoxy-1,3,5-trisilacyclohexane.

6. The method of claim 1, wherein each Z¹ and Z² independently represent a hydrogen atom, a C₁-C₂ alkyl group or a bond to a silicon atom of another monomer.

7. The method of claim 1, wherein each Z¹ and Z² independently represent a hydrogen atom, ethyl, or an oxygen bonded to a silicon atom of another monomer.

8. The method of claim 1, further comprising grafting aluminum on the organosilica material support surface prior to impregnating the organosilica material support.

9. The method of claim 1, further comprising adding to the aqueous mixture at least one compound selected from the group consisting of

(i) a further compound of Formula (VII);

(ii) a compound of Formula Z¹⁷OZ¹⁸Z¹⁹Z²⁰Si (VIII), wherein each Z¹⁷ represents a C₁-C₆ alkyl group, and Z¹⁸, Z¹⁹ and Z²⁰ are each independently selected from the group consisting of a C₁-C₆ alkyl group, a C₁-C₆ alkoxy group, a nitrogen-containing C₁-C₁₀ alkyl group, a nitrogen-containing heteroaralkyl group, and a nitrogen-containing optionally substituted heterocycloalkyl group;

(iii) compound of Formula Z²¹Z²²Z²³Si—

R¹—

SiZ²¹Z²²Z²³ (IX), wherein each Z²¹ independently represents a C₁-C₄ alkoxy group;

each Z²² and Z²³ independently represent a C₁-C₄ alkoxy group or a C₁-C₄ alkyl group; and

R¹ is selected from the group consisting a C₁-C₈ alkylene group, a C₂-C₈ alkenylene group, a C₂-C₈ alkynylene group, a nitrogen-containing C₁-C₁₀ alkylene group, an optionally substituted C₆-C₂₀ aralkyl and an optionally substituted C₄-C₂₀ heterocycloalkyl group;

(iv) a source of a trivalent metal oxide; and

(v) a combination thereof.

10. The method of claim 9, wherein the at least one compound is a further compound of Formula (VII), wherein each Z¹⁵ represents a C₁-C₂ alkoxy group and each Z¹⁶ represent C₁-C₂ alkoxy group or a C₁-C₂ alkyl group.

11. The method of claim 10, wherein the compound of Formula (VII) is 1,3,5-trimethyl-1,3,5-triethoxy-1,3,5-trisilacyclohexane.

12. The method of claim 9, wherein the at least one compound is a compound of Formula (VIII), wherein each Z¹⁷ represents a C₁-C₂ alkyl group and Z¹⁸, Z¹⁹ and Z²⁹ each independently selected from the group consisting of a C₁-C₂ alkyl group, C₁-C₂ alkoxy group, a nitrogen-containing C₃-C₁₀ alkyl group, a nitrogen-containing C₄-C₁₀ heteroaralkyl group, and a nitrogen-containing optionally substituted C₄-C₁₀ heterocycloalkyl group.

13. The method of claim 12, wherein the compound of Formula (VIII) is selected from the group consisting of tetraethyl orthosilicate, methyltriethoxysilane, (N,N-dimethylaminopropyl)trimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 4-methyl-1-(3-triethoxysilylpropyl)-piperazine, 4-(2-(triethoxysily)ethyl)pyridine, 1-(3-(triethoxysilyl)propyl)-4,5-dihydro-1H-imidazole, and (3-aminopropyl)triethoxysilane.

14. The method of claim 9, wherein the at least one compound is a compound of Formula (IX), wherein each Z²¹ represents a C₁-C₂ alkoxy group;

each Z²² and Z²³ independently represent a C₁-C₂ alkoxy group, or a C₁-C₂ alkyl group; and

R¹ is selected from the group consisting of a C₁-C₄ alkylene group, a C₂-C₄ alkenylene group, a C₂-C₄ alkynylene group, and a nitrogen-containing C₄-C₁₀ alkylene group.

15. The method of claim 14, wherein the compound of Formula (IX) is selected from the group consisting of 1,2-bis(methyldiethoxysilyl)ethane, bis(triethoxysilyl)methane, 1,2-bis(triethoxysilyl)ethylene, N,N′

-bis[(3-trimethoxysilyl)propyl]ethylenediamine, bis[(methyldiethoxysilyl)propyl]amine, and bis[(methyldimethoxysilyl)propyl]-N-methylamine.

16. The method of claim 9, wherein the at least one compound is a source of trivalent metal oxide, wherein the source of trivalent metal oxide is at least one of:

(i) a compound of Formula M³(OZ²⁴)₃ (X), wherein M³ represents a Group 13 metal and each Z²⁴ independently represents a C₁-C₆ alkyl group;

or

(ii) a compound of Formula (Z²⁵O)₂M⁴-O—

Si(OZ²⁶)₃ (XI), wherein M⁴ represents a Group 13 metal and each Z²⁵ and each Z²⁶ independently represent a C₁-C₆ alkyl group.

17. The method of claim 16, wherein the source of trivalent metal oxide is a compound of Formula (X), wherein M³ is Al or B and each Z²⁴ represents a C₁-C₄ alkyl group.

18. The method of claim 16, wherein the source of trivalent metal is a compound of Formula (XI), wherein M⁴ is Al or B;

and each Z²⁵ and each Z²⁶ independently represent a C₁-C₄ alkyl group.

19. The method of claim 9, wherein the source of a trivalent metal oxide is selected from the group consisting of aluminum trimethoxide, aluminum triethoxide, aluminum isopropoxide, and aluminum-tri-sec-butoxide.

20. The method of claim 1, wherein the aqueous mixture comprises a base and has a pH from about 8 to about 14.

21. The method of claim 20, wherein the base is ammonium hydroxide or a metal hydroxide.

22. The method of claim 1, wherein the aqueous mixture comprises an acid and has a pH from about 0.01 to about 6.0.

23. The method of claim 22, wherein the acid is an inorganic acid.

24. The method of claim 23, wherein the inorganic acid is hydrochloric acid.

25. The method of claim 1, wherein the solution is aged in step (c) for up to 144 hours at a temperature of about 50°

C. to about 200°

C.

26. The method of claim 1, wherein the pre-product is dried at a temperature of about 70°

C. to about 200°

C.

27. The method 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.

28. The method of claim 27, wherein the at least one catalyst metal is selected from the group consisting of Pt, Pd, and a mixture thereof.

29. The method of claim 1 further comprising adding a binder material selected from the group consisting of active and inactive materials, inorganic materials, clays, alumina, silica, silica-alumina, titania, zirconia, yttrium oxide, tantalum oxide, niobium oxide, activated carbon, ceramics, pumice, celite and a combination thereof.

30. The method of claim 29, wherein the binder material is selected from the group consisting of silica-alumina, alumina, silica, titania and zirconia activated carbon.

31. A hydrogenation catalyst made according to the method of claim 1.