Aromatic hydrogenation catalysts and uses thereof

• US 10,047,304 B2
• Filed: 12/11/2015
• Issued: 08/14/2018
• Est. Priority Date: 12/12/2014
• Status: Expired due to Fees

• 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, Nines, Meghan, Griffin, David A., Johnson, Ivy D.
• Primary Examiner(s): Robinson, Renee
• Application Number:
  US14/966,071
• Publication Number:
  US 20160167032A1
• Time in Patent Office: 977 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. 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 [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

(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 Z¹ and Z² independently represent a hydrogen atom, a C₁-C₂ alkyl group or a bond to a silicon atom of another monomer.

3. The process of claim 2, wherein each Z¹ and Z² 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 [Z³OZ⁴SiCH₂]₃ (II), wherein each Z³ represents a hydrogen atom, a C₁-C₄ alkyl group or a bond to a silicon atom of another monomer and each Z⁴ represents a C₁-C₆ alkyl group;

(ii) at least one independent unit of Formula Z⁵OZ⁶Z⁷Z⁸Si (III), wherein each Z⁵ represents a hydrogen atom or a C₁-C₄ alkyl group or a bond to a silicon atom of another monomer; and

Z⁶, Z⁷ and Z⁸ are each independently selected from the group consisting of a hydroxyl group, a C₁-C₄ alkyl group, a C₁-C₄ alkoxy group, a nitrogen-containing C₁-C₁₀ 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 Z⁹Z¹⁰Z¹¹Si—

R—

SiZ⁹Z¹⁰Z¹¹ (IV), wherein each Z⁹ independently represents a hydroxyl group, a C₁-C₄ alkoxy group or an oxygen bonded to a silicon atom of another comonomer;

each Z¹⁰ and Z¹¹ independently represent a hydroxyl group, a C₁-C₄ alkoxy group, a C₁-C₄ alkyl group or an oxygen bonded to a silicon atom of another monomer; and

R 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) at least one independent unit of Formula M¹(OZ¹²)₃ (V), wherein M¹ represents a Group 13 metal and each Z¹² independently represents a hydrogen atom, a C₁-C₆ alkyl or a bond to a silicon atom of another monomer;

(v) at least one independent unit of Formula (Z¹³O)₂M²-O—

Si(OZ¹⁴)₃ (VI), wherein M² represents a Group 13 metal and each Z¹³ and each Z¹⁴ independently represent a hydrogen atom, a C₁-C₆ 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 Z³ represents a hydrogen atom, a C₁-C₂ alkyl group or a bond to a silicon atom of another siloxane monomer and each Z⁴ represents a C₁-C₂ alkyl group.

6. The process of claim 5, wherein each Z³ represents a hydrogen atom, ethyl or a bond to a silicon atom of another siloxane monomer and each Z⁴ represents a methyl.

7. The process of claim 4, wherein at least one independent unit of Formula (III) is present, wherein each Z⁵ represents a hydrogen atom, a C₁-C₂ alkyl group or a bond to a silicon atom of another comonomer;

and Z⁶, Z⁷ and Z⁸ are each independently selected from the group consisting of a hydroxyl group, a C₁-C₂ alkyl group, C₁-C₂ alkoxy group, a nitrogen-containing C₃-C₁₀ alkyl group, a nitrogen-containing C₄-C₁₀ heteroalkyl group, a nitrogen-containing optionally substituted C₄-C₁₀ heterocycloalkyl group and an oxygen bonded to a silicon atom of another monomer.

8. The process of claim 7, wherein Z⁶, Z⁷ and Z⁸ are each independently selected from the group consisting of a hydroxyl group, a C₁-C₂ alkyl group, C₁-C₂ alkoxy group, and an oxygen bonded to a silicon atom of another monomer.

9. The process of claim 7, wherein each Z⁵ represents a hydrogen atom, methyl, ethyl, or a bond to a silicon atom of another comonomer;

and Z⁶, Z⁷ and Z⁸ are each independently selected from the group consisting of a hydroxyl group, methyl, methoxy, ethoxy,

10. The process of claim 4, wherein at least one independent unit of Formula (IV) is present, wherein each Z⁹ represents a hydroxyl group, a C₁-C₂ alkoxy group or an oxygen bonded to a silicon atom of another comonomer;

each Z¹⁰ and Z¹¹ independently represent a hydroxyl group, a C₁-C₂ alkoxy group, a C₁-C₂ alkyl group or an oxygen bonded to a silicon atom of another monomer; and

R is selected from the group consisting of a C₁-C₄ alkylene group, a C₂-C₄ alkenylene group, a C₂-C₄ alkynylene group, a nitrogen-containing C₄-C₁₀ alkylene group, an optionally substituted C₆-C₁₀ aralkyl and an optionally substituted C₄-C₁₂ heterocycloalkyl group.

11. The process of claim 10, wherein each Z⁹ represents a hydroxyl group, methoxy, ethoxy or an oxygen bonded to a silicon atom of another comonomer;

each Z¹⁰ and Z¹¹ 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 M¹ is Al or B and each Z¹² represents a hydrogen atom, a C₁-C₄ 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 M² is Al or B and each Z¹³ and each Z¹⁴ independently represent a hydrogen atom, a C₁-C₄ 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 m²/g to about 2000 m²/g.

15. The process of claim 1, wherein the organosilica material support has a pore volume of about 0.5 cm³/g to about 3.0 cm³/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 process of claim 1, wherein the catalyst metal is present in an amount ranging from about 0.1 to about 2.0 wt. %.

20. The process of claim 1, wherein the hydrogenation catalyst further comprises 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.

21. The process of claim 20, wherein the binder material is selected from the group consisting of silica-alumina, alumina, titania, zirconia and activated carbon.

22. The process of claim 1, wherein the hydrocarbon feedstream is a hydrocarbon fluid, a diesel boiling range feedstream, a lube oil boiling range feedstream, a whole or reduced petroleum crude, atmospheric residua, vacuum residua, propane deasphalted residua, dewaxed oil, slack wax, raffinate, or a mixture thereof.

23. The process of claim 1, wherein the hydrocarbon feedstream contains up to 0.2 wt. % of nitrogen, up to 3.0 wt. % of sulfur, and up to about 50 wt. % aromatics, all based on the hydrocarbon feedstream.

24. The process of claim 1, wherein the hydrocarbon feedstream has a sulfur content below about 100 wppm.

25. The process of claim 1, wherein the effective aromatics hydrogenation conditions comprise a temperature of about 350°

C. or less.