Methods of separating aromatic compounds from lube base stocks

• US 9,956,541 B2
• Filed: 12/11/2015
• Issued: 05/01/2018
• 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: Weigel, Scott J., Zhang, Lei, Li, Quanchang, Lacy, Darryl Donald, Podsiadlo, Paul, Calabro, David Charles, Kaul, Bal, Gleeson, James William
• Primary Examiner(s): Louie, Philip Y
• Assistant Examiner(s): Pierpont, Aaron W
• Application Number:
  US14/966,790
• Publication Number:
  US 20160168484A1
• Time in Patent Office: 872 Days
• Field of Search: 585830, 585804, 585800, 585823, 585824
• 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: B01D 2253/20 Organic adsorbents
• CPC Class Codes: B01D 2253/25 Coated, impregnated or composite adsorbents
• CPC Class Codes: B01D 2256/245 Methane
• CPC Class Codes: B01D 2257/302 Sulfur oxides
• CPC Class Codes: B01D 2257/304 Hydrogen sulfide
• CPC Class Codes: B01D 2257/40 Nitrogen compounds
• CPC Class Codes: B01D 2257/504 Carbon dioxide
• CPC Class Codes: B01D 2257/80 Water
• CPC Class Codes: B01D 53/02 by adsorption, e.g. preparative gas chromatography solid sorbent compositions B01J20/00, preparation of inorganic compounds or elements C01
• CPC Class Codes: B01D 53/04 with stationary adsorbents B01D53/025 takes precedence
• CPC Class Codes: B01D 53/0462 Temperature swing adsorption
• CPC Class Codes: B01D 53/047 Pressure swing adsorption
• CPC Class Codes: B01D 67/0088 Physical treatment with compounds, e.g. swelling, coating or impregnation
• CPC Class Codes: B01D 71/701 Polydimethylsiloxane
• CPC Class Codes: B01J 20/0229 Compounds of Fe
• CPC Class Codes: B01J 20/0237 Compounds of Cu
• 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 20/103 : comprising silica
• CPC Class Codes: B01J 20/16 : Alumino-silicates B01J20/12 takes precedence
• CPC Class Codes: B01J 20/18 : Synthetic zeolitic molecular sieves
• CPC Class Codes: B01J 20/22 : comprising organic material
• CPC Class Codes: B01J 20/262 : obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds per se C08G
• 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 20/28061 : being in the range 100-500 m2/g
• CPC Class Codes: B01J 20/28064 : being in the range 500-1000 m2/g
• CPC Class Codes: B01J 20/28066 : being more than 1000 m2/g
• CPC Class Codes: B01J 20/28069 : Pore volume, e.g. total pore volume, mesopore volume, micropore volume
• CPC Class Codes: B01J 20/28071 : being less than 0.5 ml/g
• CPC Class Codes: B01J 20/28073 : being in the range 0.5-1.0 ml/g
• CPC Class Codes: B01J 20/28076 : being more than 1.0 ml/g
• CPC Class Codes: B01J 20/28078 : Pore diameter
• CPC Class Codes: B01J 20/28083 : being in the range 2-50 nm, i.e. mesopores
• 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 20/3204 : Inorganic carriers, supports or substrates
• CPC Class Codes: B01J 20/3212 : consisting of a polymer obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds
• 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 20/3272 : Polymers obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds
• 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 2231/646 : of aromatic or heteroaromatic rings
• CPC Class Codes: B01J 23/42 : Platinum
• CPC Class Codes: B01J 23/44 : Palladium
• CPC Class Codes: B01J 29/0308 : Mesoporous materials not having base exchange properties, e.g. Si-MCM-41
• 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 37/0213 : 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: C01B 37/00 : Compounds having molecular sieve properties but not having base-exchange properties
• 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 2/00 : Processes of polymerisation
• CPC Class Codes: C08F 2/10 : Aqueous solvent
• CPC Class Codes: C08F 2/42 : using short-stopping agents
• CPC Class Codes: C08F 210/02 : Ethene
• CPC Class Codes: C08F 210/14 : Monomers containing five or more carbon atoms
• CPC Class Codes: C08F 36/04 : conjugated
• CPC Class Codes: C08F 36/20 : unconjugated
• 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 4/659 : Component covered by group C08F4/64 containing a transition metal-carbon bond C08F4/64003 - C08F4/64196 take precedence
• CPC Class Codes: C08F 4/65912 : in combination with an organoaluminium compound
• CPC Class Codes: C08F 4/65916 : supported on a carrier, e.g. silica, MgCl2, polymer
• CPC Class Codes: C08F 4/65925 : two cyclopentadienyl rings being mutually non-bridged
• CPC Class Codes: C08F 4/65927 : two cyclopentadienyl rings being mutually bridged
• CPC Class Codes: C08G 77/26 : nitrogen-containing groups
• 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 31/09 : by filtration
• CPC Class Codes: C10G 35/06 : characterised by the catalyst used
• CPC Class Codes: C10G 45/00 : Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
• CPC Class Codes: C10G 45/04 : characterised by the catalyst used
• CPC Class Codes: C10G 45/34 : characterised by the catalyst used
• 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: C10G 45/60 : characterised by the catalyst used
• CPC Class Codes: C10G 45/64 : containing crystalline alumino-silicates, e.g. molecular sieves
• CPC Class Codes: C10G 47/02 : characterised by the catalyst used
• CPC Class Codes: C10G 50/00 : Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
• CPC Class Codes: C10K 1/32 : with selectively adsorptive solids, e.g. active carbon
• CPC Class Codes: C10M 101/02 : Petroleum fractions
• CPC Class Codes: C10M 177/00 : Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
• CPC Class Codes: C10M 2203/1006 : used as base material
• CPC Class Codes: C10N 2070/00 : Specific manufacturing methods for lubricant compositions
• CPC Class Codes: C23C 16/56 : After-treatment
• CPC Class Codes: Y02C 20/40 : of CO2

Abstract

Methods are provided herein for separating an aromatic compound from a lube base stock by contacting a lube base stock containing an aromatic compound with an organosilica material.

Claims

1. A method for separating an aromatic compound from a lube base stock, the method comprising contacting a lube base stock containing an aromatic compound with an organosilica material, which is a co-polymer of:

(a) a monomer of Formula [Z¹OZ²OSiCH₂]₃ (I), wherein Z¹ and Z² each independently represent a hydrogen atom, a C₁-C₄ alkyl group, or a bond to a silicon atom of another monomer; and

(b) a cyclic polyurea monomer of Formula

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

3. The method of claim 2, wherein Z¹ and Z² each independently represent a hydrogen atom, an ethyl group, or a bond to a silicon atom of another monomer.

4. The method of claim 1, wherein each X¹ represents a hydrogen atom, a C₁-C₂ alkyl group, or a bond to a silicon atom of another monomer;

X² and X³ each independently represent a hydroxyl group, a C₁-C₂ alkyl group, a C₁-C₂ alkoxy group, or an oxygen atom bonded to a silicon atom of another monomer; and

each X⁴ represents a C₁-C₄ alkylene group bonded to a nitrogen atom of the cyclic polyurea monomer.

5. The method of claim 4, wherein each X¹ represents a hydrogen atom, a methyl group, or a bond to a silicon atom of another monomer;

X² and X³ each independently represent a hydroxyl group, a methoxy group, or an oxygen atom bonded to a silicon atom of another monomer; and

each X⁴ represents —

CH₂CH₂CH₂—

bonded to a nitrogen atom of the cyclic polyurea monomer.

6. The method of claim 1, wherein the organosilica material is a co-polymer which further comprises at least one other monomer selected from the group consisting of:

(i) an independent unit of Formula [Z³OZ⁴SiCH₂]₃ (III), 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) an independent unit of Formula Z⁵OZ⁶Z⁷Z⁸Si (IV), wherein each Z⁵ represents a hydrogen atom, 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) an independent unit of Formula Z⁹Z¹⁰Z¹¹Si—

R—

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

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

R is selected from the group consisting of 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 group, and an optionally substituted C₄-C₂₀ heterocycloalkyl group;

(iv) an independent unit of Formula M¹(OZ¹²)₃ (VI), wherein M¹ represents a Group 13 metal and each Z¹² independently represents a hydrogen atom, a C₁-C₆ alkyl group, or a bond to a silicon atom of another monomer; and

(v) an independent unit of Formula (Z¹³O)₂M²-O—

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

7. The method of claim 6, wherein at least one independent unit of Formula (III) is present, wherein each Z³ represents a hydrogen atom, a C₁-C₂ alkyl group, or a bond to a silicon atom of another monomer;

and each Z⁴ represents a C₁-C₂ alkyl group.

8. The method of claim 7, wherein each Z³ represents a hydrogen atom, an ethyl group, or a bond to a silicon atom of another monomer;

and each Z⁴ represents methyl group.

9. The method of claim 6, wherein at least one independent unit of Formula (IV) is present, wherein each Z⁵ represents a hydrogen atom, a C₁-C₂ 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-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 atom bonded to a silicon atom of another monomer.

10. The method of claim 9, wherein each Z⁵ represents a hydrogen atom, a methyl group, an ethyl 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 methyl group, a methoxy group, an ethoxy group,

11. The method of claim 6, wherein at least one independent unit of Formula (V) is present, wherein each Z⁹ represents a hydroxyl group, a C₁-C₂ alkoxy group, or an oxygen atom bonded to a silicon atom of another comonomer;

Z¹⁰ and Z¹¹ each independently represent a hydroxyl group, a C₁-C₂ alkoxy group, a C₁-C₂ alkyl group, or an oxygen atom 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 group, and an optionally substituted C₄-C₁₂ heterocycloalkyl group.

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

Z¹⁰ and Z¹¹ each independently represent a hydroxyl group, a methoxy group, an ethoxy group, a methyl group, or an oxygen atom bonded to a silicon atom of another monomer; and

R is selected from the group consisting of —

CH₂—

, —

CH₂CH₂—

, —

HC═

CH—

,

13. The method of claim 6, wherein at least one independent unit of Formula (VI) 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 of another monomer.

14. The method of claim 6, wherein at least one independent unit of Formula (VII) is present, wherein M² is Al or B and Z¹³ and Z¹⁴ each independently represent a hydrogen atom, a C₁-C₄ alkyl group, or a bond to a silicon atom of another monomer.

15. The method of claim 1, wherein the organosilica material has a total surface area of 200 m²/g to 2500 m²/g.

16. The method of claim 1, wherein the organosilica material has a pore volume of 0.1 cm³/g to 3.0 cm³/g.

17. The method of claim 1, wherein the organosilica material has an average pore diameter of 2.0 nm to 25 nm.

18. The method of claim 1, wherein the aromatic compound is a single ring aromatic compound, a double ring aromatic compound, or a multi-ring aromatic compound.

19. The method of claim 1, wherein at least 0.1 wt % of the aromatic compound is removed from the lube base stock after contacting the lube base stock with the organosilica material.

20. The method of claim 1, wherein the lube base stock is contacted with the organosilica material at a temperature of 20°

C. to 200°

C. and/or a pressure of 5 psig to 100 psig.

21. The method of claim 1, wherein the organosilica material has a total aromatic adsorption capacity of at least 3 g/100 g organosilica material.

22. The method of claim 1, wherein the organosilica material has a single ring aromatic separation factor (S12) of at least 6.

23. The method of claim 1 further comprising contacting the lube base stock containing an aromatic compound with another porous material in combination with the organosilica material.

24. The method of claim 23, wherein the another porous material is a microporous material, a mesoporous material, an analogous periodic mesoporous material, a metal oxide, carbon, or a combination thereof.

25. The method of claim 24, wherein the another porous material is a zeolite material.

26. The method of claim 1, wherein the organosilica material is packed into a column and the lube base stock is contacted therein.

27. The method of claim 1, wherein separation of the aromatic compound from the lube base stock produces an at least partially purified lube base stock.