EP1563039A1 - Process for making a lube basestock - Google Patents
Process for making a lube basestockInfo
- Publication number
- EP1563039A1 EP1563039A1 EP02808135A EP02808135A EP1563039A1 EP 1563039 A1 EP1563039 A1 EP 1563039A1 EP 02808135 A EP02808135 A EP 02808135A EP 02808135 A EP02808135 A EP 02808135A EP 1563039 A1 EP1563039 A1 EP 1563039A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- component
- zsm
- catalyst
- dimethylcyclopentane
- ratio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 104
- 229910052751 metal Inorganic materials 0.000 claims abstract description 43
- 239000002184 metal Substances 0.000 claims abstract description 43
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 239000002808 molecular sieve Substances 0.000 claims abstract description 18
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 17
- 239000008188 pellet Substances 0.000 claims abstract description 12
- 229910052809 inorganic oxide Inorganic materials 0.000 claims abstract description 7
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 46
- IFTRQJLVEBNKJK-UHFFFAOYSA-N Ethylcyclopentane Chemical compound CCC1CCCC1 IFTRQJLVEBNKJK-UHFFFAOYSA-N 0.000 claims description 44
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 23
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 23
- XAZKFISIRYLAEE-UHFFFAOYSA-N 1,3-dimethylcyclopentane Chemical compound CC1CCC(C)C1 XAZKFISIRYLAEE-UHFFFAOYSA-N 0.000 claims description 19
- 238000005984 hydrogenation reaction Methods 0.000 claims description 15
- 229910052697 platinum Inorganic materials 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- QWHNJUXXYKPLQM-UHFFFAOYSA-N 1,1-dimethylcyclopentane Chemical compound CC1(C)CCCC1 QWHNJUXXYKPLQM-UHFFFAOYSA-N 0.000 claims description 14
- 229910052763 palladium Inorganic materials 0.000 claims description 14
- RIRARCHMRDHZAR-UHFFFAOYSA-N 1,2-dimethylcyclopentane Chemical compound CC1CCCC1C RIRARCHMRDHZAR-UHFFFAOYSA-N 0.000 claims description 11
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 10
- XAZKFISIRYLAEE-RNFRBKRXSA-N (1r,3r)-1,3-dimethylcyclopentane Chemical compound C[C@@H]1CC[C@@H](C)C1 XAZKFISIRYLAEE-RNFRBKRXSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000395 magnesium oxide Substances 0.000 claims description 6
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 229910052680 mordenite Inorganic materials 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 229910001404 rare earth metal oxide Inorganic materials 0.000 claims 1
- 239000000843 powder Substances 0.000 abstract description 6
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 19
- 239000006185 dispersion Substances 0.000 description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000011593 sulfur Substances 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- 239000010457 zeolite Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229910021536 Zeolite Inorganic materials 0.000 description 10
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 6
- MUPYMRJBEZFVMT-UHFFFAOYSA-N 1-chloro-4-dimethoxyphosphorylsulfanylbenzene Chemical compound COP(=O)(OC)SC1=CC=C(Cl)C=C1 MUPYMRJBEZFVMT-UHFFFAOYSA-N 0.000 description 5
- 150000001940 cyclopentanes Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- RIRARCHMRDHZAR-RNFRBKRXSA-N (1r,2r)-1,2-dimethylcyclopentane Chemical compound C[C@@H]1CCC[C@H]1C RIRARCHMRDHZAR-RNFRBKRXSA-N 0.000 description 4
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229940032007 methylethyl ketone Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- RIRARCHMRDHZAR-KNVOCYPGSA-N (1r,2s)-1,2-dimethylcyclopentane Chemical compound C[C@H]1CCC[C@H]1C RIRARCHMRDHZAR-KNVOCYPGSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- -1 methyl t-butyl ethers Chemical class 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 2
- XAZKFISIRYLAEE-KNVOCYPGSA-N (1r,3s)-1,3-dimethylcyclopentane Chemical compound C[C@H]1CC[C@@H](C)C1 XAZKFISIRYLAEE-KNVOCYPGSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical class O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- UNYSKUBLZGJSLV-UHFFFAOYSA-L calcium;1,3,5,2,4,6$l^{2}-trioxadisilaluminane 2,4-dioxide;dihydroxide;hexahydrate Chemical compound O.O.O.O.O.O.[OH-].[OH-].[Ca+2].O=[Si]1O[Al]O[Si](=O)O1.O=[Si]1O[Al]O[Si](=O)O1 UNYSKUBLZGJSLV-UHFFFAOYSA-L 0.000 description 1
- 229910052676 chabazite Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 229910052675 erionite Inorganic materials 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000003870 refractory metal Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing iron group metals, noble metals or copper
- B01J29/74—Noble metals
- B01J29/7484—TON-type, e.g. Theta-1, ISI-1, KZ-2, NU-10 or ZSM-22
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/064—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof containing iron group metals, noble metals or copper
- B01J29/068—Noble metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
- B01J29/42—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively containing iron group metals, noble metals or copper
- B01J29/44—Noble metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/80—Mixtures of different zeolites
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/19—Catalysts containing parts with different compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/58—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins
- C10G45/60—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins characterised by the catalyst used
- C10G45/64—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins characterised by the catalyst used containing crystalline alumino-silicates, e.g. molecular sieves
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/391—Physical properties of the active metal ingredient
- B01J35/394—Metal dispersion value, e.g. percentage or fraction
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/10—Lubricating oil
Definitions
- This invention relates to the hydroisomerization of waxy feeds including slack wax, slack wax isomerate, Fischer-Tropsch wax, Fischer-Tropsch hydroisomerate waxy raffmates, and waxy distillates to produce a lube oil basestock or blending stock. More specifically, this invention relates to the conversion of a waxy feed using a mixed catalyst having a preselected acidity capable of promoting the formation of a basestock having a predetermined (VI) within a range of Vis.
- a mixed catalyst having a preselected acidity capable of promoting the formation of a basestock having a predetermined (VI) within a range of Vis.
- Waxy feeds can be converted to liquid products using well known catalytic dewaxing catalysts; however, in these instances the selective cracking of paraffins typically results in a loss of viscosity (VI) which is undesirable.
- VI viscosity
- United States Patent Number 4,428, 865, Oleck, et al. claims a method to enhace the pour point and visosity index of crude oils of high wax content by contacting the highly waxy feed with two different zeolites such as ZSM-5 and ZSM- 35.
- the presently disclosed invention is a method for hydroisomerizing a waxy feed to produce improved yield of a lube basestock which comprises:
- a first dewaxing component selected from 8, 10 and 12 ring molecular sieves and mixtures thereof having a metal hydrogenation component dispersed thereon;
- both the first and second component comprise at least one 8, 10 ior 12 ring molecular sieve or a mixture thereof. Both the first and second component have a metal hydrogenation component dispersed thereon.
- Figure 1 is a schematic drawing showing the conversion of methylcyclohexane to various cyclopentane compounds at 320°C.
- the feed suitable in the practice of the present invention includes waxy hydrocarbon oils such as slack wax, slack wax isomerate, Fischer-Tropsch wax, Fischer-Tropsch isomerate waxy raffmates and waxy distillates.
- waxy hydrocarbon oils such as slack wax, slack wax isomerate, Fischer-Tropsch wax, Fischer-Tropsch isomerate waxy raffmates and waxy distillates.
- waxy hydrocarbon oils such as slack wax, slack wax isomerate, Fischer-Tropsch wax, Fischer-Tropsch isomerate waxy raffmates and waxy distillates.
- waxy hydrocarbon oils such as slack wax, slack wax isomerate, Fischer-Tropsch wax, Fischer-Tropsch isomerate waxy raffmates and waxy distillates.
- Such feeds will have wax contents of 15% or more.
- the preferred feed will have a nitrogen and sulfur content each below about 20% or more.
- the preferred feed will have
- any of the conventional hydrotreating catalysts can be employed like Ni/Mo on alumina, Ni/W on alumina Co/Mo on alumina.
- any of the Group VIB to Group VIII. are those metals of the Periodic Table of Elements; Sargent- Welch Scientific Co.
- Non-limiting commercial examples of such are identified as HDN- 30, KF-840, and KF-848, etc.
- Hydrotreating is conducted so as to lower the sulfur and nitrogen contents to levels of 20 wppm or less nitrogen or 20 wppm or less sulfur especially 10 ppm less nitrogen and 10 ppm or less sulfur and most preferably to levels below 5 ppm for nitrogen and 5 ppm or less for sulfur.
- Waxy feeds secured from natural petroleum sources contain quantities of sulfur and nitrogen compounds which are known to deactivate wax hydroisomerization catalysts. To prevent this deactivation it is preferred that the feed contain no more than 10 ppm sulfur, preferably less than 2 ppm sulfur and no more than 2 ppm nitrogen, preferably less than 1 ppm nitrogen.
- the feed is preferably hydrotreated to reduce the sulfur and nitrogen content.
- Hydrotreating can be conducted using any typical hydrotreating catalyst such as Ni/Mo on alumina, Co/Mo on alumina, Co/Ni/Mo on alumina, e.g., KF-840, KF-843, HDN-30, HDN-60, Criteria C-411, etc.
- bulk catalysts comprising Ni/Mn/Mo or Cr/Ni/Mo sulfides as described in U.S. Patent 5,122,258 can be used.
- Hydrotreating is performed at temperatures in the range 280°C to 400°C, preferably 340°C to 380°C at pressures in the range 500 to 3000 psi, hydrogen treat gas rate in the range of 500 to 5000 SCF/bbl and a flow velocity in the range 0.1 to 5 LHSV, preferably 1 to 2 LHSV.
- the hydrotreated waxy oil is stripped to remove ammonia and H2S and then is subjected to the hydroisomerization process of the present invention.
- the catalyst employed in the hydroisomerization of waxy feeds in accordance with the present invention is a unitized mixed powdered pellet catalyst.
- unitized as used here and in the claims means that each pellet is one made by mixing together a powdered first component with a powdered second component and pelletizing the mixture to produce pellets each of which contain all of the powder components previously recited.
- the unitized catalyst can be prepared by starting with individual finished powdered components pulverizing and powdering such individual finished components, mixing the powdered materials together to form a homogeneous mass, then compressing/extruding and pelleting thus producing the unitized pellet catalysts. Pulverizing and powdering is to a consistency achievable using a ball mill or other such conventional powdering means to a particle size less than 100 microns.
- the first component is a catalytic dewaxing component including crystalline 8, 10 and 12 ring molecular sieves.
- Crystalline molecular sieves include alumino silicates and alumino phosphates.
- Examples of crystalline alumino silicates include zeolites such as erionite, chabazite, ZSM-5, ZSM-11, ZSM-12, Theta- 1 (ZSM-22), ZSM-23, ZSM-35, natural and synthetic ferrierites, ZSM-48, ZSM-57, SSZ-31, beta, mordenite, offretite, ECR-42, MCM-71, and ITQ-13.
- Examples of crystalline aluminum phosphates include SAPO-11, SAPO-41, SAPO-31, MAPO-11 and MAPO-31.
- Preferred molecular sieves include ZSM-5, ZSM-22, ZSM-23, ZSM- 48, ferrierites, SSZ-31, SAPO-11, ECR-42, MCM-71, and ITQ-13.
- the most preferred molecular sieves are ZSM-48, ECR-42, MCM-71, SSZ-31, and ITQ-13.
- the second isomerization component can be any of the typical isomerization catalyst such as those comprising amorphous refractory metal oxide support base (e.g., alumina, silica, zirconia, titania, silica-magnesia, silica-alumina, etc.) on which has been preferably deposited a catalytically active metal selected from Group VI B, Group VII B, Group VIII metals and mixtures thereof, preferably at lease one Group VIII metal, more preferably at least one noble Group VIII metal, most preferably Pt, Pd, and mixtures thereof, and optionally including a promoter or dopant such as halogen, phosphorus, boron, yttria, magnesia, etc., preferably halogen, yttria or magnesia, most preferably fluorine.
- amorphous refractory metal oxide support base e.g., alumina, silica, zirconia, titania, silica-magnesi
- the catalytically active metals are present in the range 0.1 to 5 wt%, preferably 0.1 to 3 wt%, more preferably 0.1 to 2 wt%, most preferably 0.1 to 1 wt%.
- the promoters and dopants are used to control the acidity of the isomerization catalyst.
- acidity of the resultant catalyst is reduced by addition of a basic material such as yttria or magnesia or by controlling the ratio of silica: aluminum in the silica-alumina.
- the metal hydrogenation component can be deposited on either the first dewaxing component, the second isomerization component or preferably on both the first and second components.
- the metal is selected from at least one of Group VIB and Group VIII, preferably Group VIII, more preferably Pt, Pd and mixtures thereof.
- the amount of metal can range from 0.1 to 30 wt%, based on catalyst. If the metal is Pt or Pd, the preferred amount is from 0.1 to 5 wt%, based on catalyst. In order to maximize catalyst utilization, it is preferred that the metal dispersion be at least 0.3 (on a scale where 100% metal dispersion is 1.0) if the metal is only on one component. If the metal is on both components, then it is preferred that the metal dispersion (D) times the metal concentration (C) (i.e., D x C) on one of the components be at least 0.08.
- the first and second components are combined in a ratio sufficient to promote wax isomerization and naphthene destruction without substantial decrease in VI.
- the zeolite to amorphous inorganic oxide ratios for catalysts according to the invention range from about 1:1 to 1:20 by weight, subject to the MCH test described below.
- One technique for determining the proper ratio of first and second components in the catalyst is based on an evaluation of the combined components containing about 0.5 wt% Pt in converting methylcyclohexane (MCH) to various cyclopentane compounds.
- the second factor is when the catalyst, impregnated with about 0.5 wt% Pt and evaluated in converting methylcyclohexane to various cyclopentane compounds at 10% conversion, exhibits a selectivity for ethylcyclopentane (ECP) formation above at least 50%.
- ECP ethylcyclopentane
- the ratio of trans- 1,2-DCMP to trans-l,3-DCMP is adjusted to less than about 1 predominantly by controlling both the number and strength of the amorphous isomerization component. It is preferred to use lower acid strength amorphous components such as alumina.
- a catalyst that will maximize VI is produced by increasing the acid strength of the amorphous phase.
- it is preferred to use higher acid strength amophous components such as silica-aluminas or modified silica-aluminas.
- Another way of making such a catalyst is by changing the ratio of the microporous component to the amorphous component such that the unitized catalyst has a trans- l,2/trans-l,3 DMCP ratio of >1.
- the hydroisomerization process utilizing the catalyst of the present invention is conducted at temperatures between about 200°C to 400°C, preferably 250°C to 380°C, and most preferably 300°C to 350°C at hydrogen partial pressures between about 350 to 5,000 psig (2.41 to 34.6 mPa), preferably 1,000 to 2500 psig (7.0 to 17.2 mPa), a hydrogen gas treat ratio of 500 to 10,000 SCF H 2 /bbl (89 to 1780 m3/ m 3), preferably 2,000 to 5,000 SCF H 2 bbl (356 to 890 m3/m ) and a LHSV of 0.1 to 10 v/v/l ⁇ r, preferably 0.5 to 5 v/v/hr, and more preferably 1 to 2 v/v/hr.
- the waxy feed is first subject to solvent dewaxing to a pour point of the order of +10°C or lower.
- the dewaxing solvent used may include the C3-C6 ketones such as methyl ethyl ketone (MEK), methyl isobutyl ketone (MIBK), mixtures of MEK and MIBK, aromatic hydrocarbons like toluene, mixtures of ketones and aromatics like MEK/toluene, ethers such as methyl t-butyl ethers and mixtures of same with ketones or aromatics.
- MEK methyl ethyl ketone
- MIBK methyl isobutyl ketone
- aromatic hydrocarbons like toluene
- ethers such as methyl t-butyl ethers and mixtures of same with ketones or aromatics.
- liquefied, normally gaseous hydrocarbons like propane, propylene, butane, butylene, and combinations thereof may be used as the solvent.
- the solvent employed will be an equal volume mixture of methyl ethyl ketone and methyl isobutyl ketone.
- the isomerate to solvent ratio will range between 1 to 10 and preferably will be about 1:3.
- both the first and second components be at least one crystalline 8, 10 or 12 ring molecular sieves. It is also contemplated that both the first and second components be a mixture of 8, 10 or 10 ring molecular sieves. Thus, both the first and second components can be selected from any of the 8, 10 and 12 ring molecular sieves listed above, and mixtures thereof. It is preferred that the first component be ITQ-13 and the second component be selected from ZSM-48, ZSM-35, ZSM-22, ZSM-23, ZSM-57, SSZ-31, and mixtures thereof.
- the first component be selected from ITQ-13, ZSM-57, and mixtures thereof
- the second component be selected from ZSM-22, ZSM-23, ZSM-35, ZSM-48, SSZ-31, and mixtures therof.
- the metal hydrogenation component can be deposited on either the first dewaxing component, the second isomerization component or preferably on both the first and second components.
- the metal is selected from at least one of Group VIB and Group VIII, preferably Group VIII, more preferably Pt, Pd, and mixtures thereof.
- the amount of metal can range from 0.1 to 30 wt.%, based on catalyst. If the metal is Pt, Pd or a mixture thereof, the preferred amount is from 0.1 to 5 wt.%, based on catalyst. In order to maximize catalyst conversion, it is preferred that the metal dispersion be at least 0.3 if the metal is only on one component.
- the dispersion on one of the components be at least 0.3.
- the first and second components are combined in a ratio sufficient to promote wax isomerization and naphthene destruction without substantial decrease in VI.
- the zeolite to amorphous inorganic oxide ratios for catalysts according to the invention range from about 1:1 to 1:20 by weight, subject to the MCH test described below.
- One technique for determining the proper ratio of first and second components in the catalyst is based on an evaluation of the combined components containing about 0.5 wt.% Pt in converting methylcyclohexane (MCH) to various cyclopentane compounds.
- Catalyst that at 320°C provide a ratio of trans 1,2- dimethylcyclopentane to trans 1,3-dimethylcyclopentane (t-l,2/t-l,3 DMCP) in the range of less than about 1 have been found to promote maximum yields of basestocks.
- the second factor is when the catalyst, impregnated with about 0.5 wt.% Pt and evaluated in converting methyl cyclohexane to various cyclopentane compounds at 320° at 10% conversion, exhibits a selectivity for ethylcyclopentane (ECP) formation above at least 50%.
- ECP ethylcyclopentane
- the ratio of trans- 1 ,2-DCMP to trans- 1 ,3-DCMP is adjusted to less than about 1 predominantly by controlling the acidity of the amorphous isomerization component. It is preferred to use weakly acidic amorphous components such as alumina. Increasing the acidity of the amorphous phase generally increases the above-cited ratio.
- the hydroisomerization process utilizing the catalyst of the present invention is conducted at temperatures between about 200°C to 400°C, preferably 250°C to 380°C and most preferably 300°C to 350°C at pressures between about 500 to 5,000 psig (3.55 to 34.6 mPa), preferably 1,000 to 2000 psig (7.0 to 13.9 mPa), a hydrogen gas treat ratio of 500 to 10000 SCF H 2 /B (89 to 1780 m 3 /m 3 ), preferably 2,000 to 5,000 SCF H 2 /B (356 to 890 m3/m3) and a LHSV of 0.5 to 5 v/v/hr, preferably 1 to 2 v/v/hr.
- the wax feed is first subject to solvent dewaxing to a pour point on the order of +10°C or lower.
- the dewaxing solvent used may include the C 3 -C 6 ketones such as methyl- ethyl ketone (MEK), methyl isobutyl ketone (MIBK), mixtures of MEK and MIBK, aromatic hydrocarbons like toluene, mixtures of ketones and aromatics like MEK/toluene, ethers such as methyl t-butyl ethers and mixtures of same with ketones or aromatics.
- MEK methyl- ethyl ketone
- MIBK methyl isobutyl ketone
- aromatic hydrocarbons like toluene
- ethers such as methyl t-butyl ethers and mixtures of same with ketones or aromatics.
- liquified, normally gaseous hydrocarbons like propane, propylene, butane, butylene, and combinations thereof may be used as the solvent.
- the solvent employed will be an equal volume mixture of methyl ethyl ketone and methyl isobutyl ketone.
- the isomerate to solvent ratio will range between 1 to 10 and preferably will be about 1:3.
- This example illustrates the yield -VI trade-off on a hydrocracker distillate (Feed A) for catalysts with different degrees of acidity in the amorphous component.
- the physical properties of the hydrocracker distillate (Feed A) are shown in Table 1.
- the catalyst in Table 2 (column C) was made by combining the zeolite TON with silica-alumina (Si-Al) using the same technique as used in column A to produce a homogeneous powdered catalyst before forming into pellets.
- the palladium was loaded (as palladium tetraamine dinitrate) on to the finished unitized catalyst by incipient wetness.
- Table 2 shows a comparison of activity and selectivity of these two catalysts for hydrodewaxing versus solvent dewaxing (column A).
- the acidity differences of each catalyst component and the corresponding finished unitized catalysts is also shown using the reaction of methylcyclohexane at 320°C.
- the table clearly shows the higher acidity (greater number and acid strength) silica-alumina catalyst (column C) gives lower yield but much higher VI compared with the very low acidity associated with alumina (column B) which results in high yield but a debit in VI.
- This example further illustrates the yield- VI trade off and shows a comparison of activity and selectivity of two catalysts for hydrodewaxing a hydrocraker distillate (Feed B) versus solvent dewaxing.
- the physical properties of the hydrocracker distillate (Feed B) are shown in Table 3.
- Wax Content wt% 22.4
- This example further illustrates the yield- VI trade and shows a comparison of activity and selectivity of two catalysts for hydroisomerization a hydrocraker distillate (Feed B) versus solvent dewaxing.
- This example illustrates that by changing the relative amounts of microporous component to amorphous component the overall acidity of the unitized catalyst an be tailored to maximize yield or VI.
- Table 5 compares two unitized catalysts both of which have been made by combining the powdered ZSM-5 (Si/Al ratio 110) with the powdered amorphous component in different ratios and then loading platinum by incipient wetness using platinum tetraamine dichloride.
- Table 5 shows a comparison of activity and selectivity for these catalysts for dewaxing hydrocracker Distillate B, the physical properties of which are shown in Table 3, with solvent dewaxing.
- the catalyst in column B which has a 1,2/1,3 DMCP ratio of ⁇ 1 shows higher yield but lower VI than the catalyst in column C which has a 1,2/1,3 DMCP ratio >1.
- the catalysts in Table 6 were made by combining the zeolite theta- 1 (TON) in the powder form with alumina (BET Surface Area 190m 2 /m 3 ) in the powder form followed by intimate mixing so as to form a homogeneous powdered mixture and then forming into catalyst pellets by pressing in a die and sizing to the required mesh size.
- TON zeolite theta- 1
- BET Surface Area 190m 2 /m 3 alumina
- Table 6 columns A and B, compares the activity of two TON zeolite/alumina mixed powder catalysts in which the noble metal has been loaded only on the TON zeolite component.
- the Pd TON/alumina catalyst (column B), which has 12% metal dispersion, is shown to have much lower activity for pour point reduction than the Pt TON/alumina catalyst (column A) which has 65 % metal dispersion.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Catalysts (AREA)
- Lubricants (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US60186700A | 2000-10-02 | 2000-10-02 | |
PCT/US2002/036521 WO2004044097A1 (en) | 2000-10-02 | 2002-11-12 | Process for making a lube basestock |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1563039A1 true EP1563039A1 (en) | 2005-08-17 |
Family
ID=32313256
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP02808135A Withdrawn EP1563039A1 (en) | 2000-10-02 | 2002-11-12 | Process for making a lube basestock |
Country Status (6)
Country | Link |
---|---|
US (1) | US20060138023A1 (en) |
EP (1) | EP1563039A1 (en) |
JP (1) | JP2006506484A (en) |
AU (1) | AU2002368354A1 (en) |
CA (1) | CA2505609A1 (en) |
WO (1) | WO2004044097A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7638453B2 (en) * | 2004-09-08 | 2009-12-29 | Exxonmobile Research And Engineering Company | Molecular sieve containing hydrodewaxing catalysts |
CA2762660C (en) | 2009-06-12 | 2017-11-28 | Albemarle Europe Sprl | Sapo molecular sieve catalysts and their preparation and uses |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3755145A (en) * | 1971-03-17 | 1973-08-28 | Mobil Oil Corp | Lube oil hydrocracking with zsm-5 zeolite |
US4437975A (en) * | 1977-07-20 | 1984-03-20 | Mobil Oil Corporation | Manufacture of lube base stock oil |
US4181598A (en) * | 1977-07-20 | 1980-01-01 | Mobil Oil Corporation | Manufacture of lube base stock oil |
US4259170A (en) * | 1979-09-14 | 1981-03-31 | Mobil Oil Corporation | Process for manufacturing lube base stocks |
US4743355A (en) * | 1979-10-15 | 1988-05-10 | Union Oil Company Of California | Process for producing a high quality lube oil stock |
US4428865A (en) * | 1981-01-13 | 1984-01-31 | Mobil Oil Corporation | Catalyst composition for use in production of high lubricating oil stock |
US4414097A (en) * | 1982-04-19 | 1983-11-08 | Mobil Oil Corporation | Catalytic process for manufacture of low pour lubricating oils |
US4419220A (en) * | 1982-05-18 | 1983-12-06 | Mobil Oil Corporation | Catalytic dewaxing process |
US4428819A (en) * | 1982-07-22 | 1984-01-31 | Mobil Oil Corporation | Hydroisomerization of catalytically dewaxed lubricating oils |
US4601993A (en) * | 1984-05-25 | 1986-07-22 | Mobil Oil Corporation | Catalyst composition dewaxing of lubricating oils |
US4767522A (en) * | 1984-11-28 | 1988-08-30 | Mobil Oil Corporation | Distillate dewaxing process with mixed zeolites |
US4960504A (en) * | 1984-12-18 | 1990-10-02 | Uop | Dewaxing catalysts and processes employing silicoaluminophosphate molecular sieves |
US4867861A (en) * | 1985-06-18 | 1989-09-19 | Union Oil Company Of California | Process and catalyst for the dewaxing of shale oil |
US4859311A (en) * | 1985-06-28 | 1989-08-22 | Chevron Research Company | Catalytic dewaxing process using a silicoaluminophosphate molecular sieve |
US5082986A (en) * | 1989-02-17 | 1992-01-21 | Chevron Research Company | Process for producing lube oil from olefins by isomerization over a silicoaluminophosphate catalyst |
ES2076360T3 (en) * | 1989-02-17 | 1995-11-01 | Chevron Usa Inc | ISOMERIZATION OF LUBRICATING OILS, WAXES AND OIL WAXES USING A SILICOALUMINOPHOSPHATE MOLECULAR SCREEN CATALYST. |
US5246566A (en) * | 1989-02-17 | 1993-09-21 | Chevron Research And Technology Company | Wax isomerization using catalyst of specific pore geometry |
US5139647A (en) * | 1989-08-14 | 1992-08-18 | Chevron Research And Technology Company | Process for preparing low pour middle distillates and lube oil using a catalyst containing a silicoaluminophosphate molecular sieve |
US5264116A (en) * | 1991-07-24 | 1993-11-23 | Mobil Oil Corporation | Production of lubricants by hydrocracking and hydroisomerization |
WO1994010263A1 (en) * | 1992-10-28 | 1994-05-11 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of lubricating base oils |
US5413695A (en) * | 1993-01-06 | 1995-05-09 | Chevron Research And Technology Company, A Division Of Chevron U.S.A. Inc. | Process for producing lube oil from solvent refined oils by isomerization over a silicoaluminophosphate catalyst |
US5885438A (en) * | 1993-02-12 | 1999-03-23 | Mobil Oil Corporation | Wax hydroisomerization process |
US5977425A (en) * | 1994-11-22 | 1999-11-02 | Exxon Research And Engineering Co | Method for upgrading waxy feeds using a catalyst comprising mixed powdered dewaxing catalyst and powdered isomerization catalyst formed into a discrete particle |
CA2204278C (en) * | 1994-11-22 | 2003-12-23 | Exxon Research & Engineering Company | A method for upgrading waxy feeds using a catalyst comprising mixed powdered dewaxing catalyst and powdered isomerization catalyst formed into a discrete particle |
US5725755A (en) * | 1995-09-28 | 1998-03-10 | Mobil Oil Corporation | Catalytic dewaxing process for the production of high VI lubricants in enhanced yield |
US5965475A (en) * | 1997-05-02 | 1999-10-12 | Exxon Research And Engineering Co. | Processes an catalyst for upgrading waxy, paraffinic feeds |
AU742605B2 (en) * | 1998-02-13 | 2002-01-10 | Exxon Research And Engineering Company | Process for making a lube basestock |
EP1062306B1 (en) * | 1998-02-13 | 2017-08-09 | ExxonMobil Research and Engineering Company | A lube basestock with excellent low temperature properties and a method for making |
US6080301A (en) * | 1998-09-04 | 2000-06-27 | Exxonmobil Research And Engineering Company | Premium synthetic lubricant base stock having at least 95% non-cyclic isoparaffins |
US6962651B2 (en) * | 2003-03-10 | 2005-11-08 | Chevron U.S.A. Inc. | Method for producing a plurality of lubricant base oils from paraffinic feedstock |
-
2002
- 2002-11-12 WO PCT/US2002/036521 patent/WO2004044097A1/en active Application Filing
- 2002-11-12 US US10/532,142 patent/US20060138023A1/en not_active Abandoned
- 2002-11-12 AU AU2002368354A patent/AU2002368354A1/en not_active Abandoned
- 2002-11-12 JP JP2004551374A patent/JP2006506484A/en not_active Withdrawn
- 2002-11-12 CA CA002505609A patent/CA2505609A1/en not_active Abandoned
- 2002-11-12 EP EP02808135A patent/EP1563039A1/en not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO2004044097A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO2004044097A1 (en) | 2004-05-27 |
JP2006506484A (en) | 2006-02-23 |
CA2505609A1 (en) | 2004-05-27 |
US20060138023A1 (en) | 2006-06-29 |
AU2002368354A1 (en) | 2004-06-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU743235B2 (en) | Process for improving basestock low temperature performance using a combination catalyst system | |
US5723716A (en) | Method for upgrading waxy feeds using a catalyst comprising mixed powdered dewaxing catalyst and powdered isomerization catalyst formed into a discrete particle (LAW082) | |
US6620312B1 (en) | Process for making a lube basestock with excellent low temperature properties | |
EP1244762B1 (en) | A diesel fuel having a very high iso-paraffin to normal paraffin mole ratio | |
US5977425A (en) | Method for upgrading waxy feeds using a catalyst comprising mixed powdered dewaxing catalyst and powdered isomerization catalyst formed into a discrete particle | |
JP2002503756A (en) | Lubricating oil production with mixed catalyst systems. | |
JPH10503542A (en) | Production of lubricating oils with VI-selective catalysts | |
EP2262879A2 (en) | Production of high viscosity index lube base oils | |
AU742605B2 (en) | Process for making a lube basestock | |
EP1563039A1 (en) | Process for making a lube basestock | |
WO2004043594A1 (en) | Process for improving basestock low temeperature performance using a combination catalyst system | |
US20060142142A1 (en) | Process for improving basestock low temeperature performance using a combination catalyst system |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20050601 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LI LU MC NL PT SE SK TR |
|
AX | Request for extension of the european patent |
Extension state: AL LT LV MK RO SI |
|
DAX | Request for extension of the european patent (deleted) | ||
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: BAUMGARTNER, JOSEPH, E. Inventor name: LINEK, SANDRA, J. Inventor name: SOLED, STUART, L. Inventor name: CODY, IAN, A. Inventor name: HANTZER, SYLVAIN, S. Inventor name: MCVICKER, GARY B. Inventor name: MURPHY, WILLIAM, J. |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20090603 |