CA2099359C - Alkylation catalyst regeneration - Google Patents

Alkylation catalyst regeneration

Info

Publication number: CA2099359C
Authority: CA; Canada
Prior art keywords: sulfone; recited; mixture; aso; component
Prior art date: 1992-08-27
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.): Expired - Fee Related

Application number

CA002099359A

Other languages

English (en)

French (fr)

Other versions

CA2099359A1 (en

Inventor

Alan D. Eastman

Ronald G. Abbott

Robert B. Eldridge

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Phillips Petroleum Co

Original Assignee

Phillips Petroleum Co

Priority date (The priority date 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 date listed.)

1992-08-27

Filing date

1993-06-28

Publication date

1999-06-15

1993-06-28 Application filed by Phillips Petroleum Co filed Critical Phillips Petroleum Co

1994-02-28 Publication of CA2099359A1 publication Critical patent/CA2099359A1/en

1999-06-15 Application granted granted Critical

1999-06-15 Publication of CA2099359C publication Critical patent/CA2099359C/en

2013-06-28 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims description 140
238000005804 alkylation reaction Methods 0.000 title claims description 78
230000029936 alkylation Effects 0.000 title description 48
230000008929 regeneration Effects 0.000 title description 16
238000011069 regeneration method Methods 0.000 title description 16
239000000203 mixture Substances 0.000 claims abstract description 260
150000003457 sulfones Chemical class 0.000 claims abstract description 159
238000000034 method Methods 0.000 claims abstract description 77
229910000039 hydrogen halide Inorganic materials 0.000 claims abstract description 73
239000012433 hydrogen halide Substances 0.000 claims abstract description 73
230000002441 reversible effect Effects 0.000 claims abstract description 72
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical group O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 55
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 49
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 47
238000006243 chemical reaction Methods 0.000 claims description 44
229930195733 hydrocarbon Natural products 0.000 claims description 44
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 40
150000002430 hydrocarbons Chemical class 0.000 claims description 40
239000004215 Carbon black (E152) Substances 0.000 claims description 29
239000002904 solvent Substances 0.000 claims description 26
239000012530 fluid Substances 0.000 claims description 23
-1 glycol ethers Chemical class 0.000 claims description 23
239000006227 byproduct Substances 0.000 claims description 19
150000001336 alkenes Chemical class 0.000 claims description 17
238000000926 separation method Methods 0.000 claims description 16
239000007795 chemical reaction product Substances 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 13
229920002717 polyvinylpyridine Polymers 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
150000001412 amines Chemical group 0.000 claims description 11
239000000047 product Substances 0.000 claims description 10
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 7
150000001298 alcohols Chemical class 0.000 claims description 6
150000001350 alkyl halides Chemical class 0.000 claims description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
229920001577 copolymer Polymers 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
150000002334 glycols Chemical class 0.000 claims description 6
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
229920000885 poly(2-vinylpyridine) Polymers 0.000 claims description 6
229920000075 poly(4-vinylpyridine) Polymers 0.000 claims description 6
239000011261 inert gas Substances 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 2
239000000463 material Substances 0.000 abstract description 54
239000003463 adsorbent Substances 0.000 abstract description 20
239000002585 base Substances 0.000 description 39
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 24
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 20
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 14
230000003472 neutralizing effect Effects 0.000 description 13
238000001179 sorption measurement Methods 0.000 description 13
239000001282 iso-butane Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 11
125000003118 aryl group Chemical group 0.000 description 10
229920000642 polymer Polymers 0.000 description 10
239000000376 reactant Substances 0.000 description 10
150000001875 compounds Chemical class 0.000 description 9
238000006386 neutralization reaction Methods 0.000 description 9
125000000217 alkyl group Chemical group 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
230000000694 effects Effects 0.000 description 7
238000002474 experimental method Methods 0.000 description 6
239000003921 oil Substances 0.000 description 6
239000011149 active material Substances 0.000 description 5
125000002877 alkyl aryl group Chemical group 0.000 description 5
125000005248 alkyl aryloxy group Chemical group 0.000 description 5
125000003710 aryl alkyl group Chemical group 0.000 description 5
125000004104 aryloxy group Chemical group 0.000 description 5
239000011521 glass Substances 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
239000007788 liquid Substances 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 4
VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
150000001491 aromatic compounds Chemical class 0.000 description 4
238000009835 boiling Methods 0.000 description 4
230000005484 gravity Effects 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000011143 downstream manufacturing Methods 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000011148 porous material Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 description 2
PJUOHDQXFNPPRF-UHFFFAOYSA-N 2,6-diphenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=N1 PJUOHDQXFNPPRF-UHFFFAOYSA-N 0.000 description 2
HVHZEKKZMFRULH-UHFFFAOYSA-N 2,6-ditert-butyl-4-methylpyridine Chemical compound CC1=CC(C(C)(C)C)=NC(C(C)(C)C)=C1 HVHZEKKZMFRULH-UHFFFAOYSA-N 0.000 description 2
PCFUWBOSXMKGIP-UHFFFAOYSA-N 2-benzylpyridine Chemical compound C=1C=CC=NC=1CC1=CC=CC=C1 PCFUWBOSXMKGIP-UHFFFAOYSA-N 0.000 description 2
UUIMDJFBHNDZOW-UHFFFAOYSA-N 2-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC=N1 UUIMDJFBHNDZOW-UHFFFAOYSA-N 0.000 description 2
LUYISICIYVKBTA-UHFFFAOYSA-N 6-methylquinoline Chemical compound N1=CC=CC2=CC(C)=CC=C21 LUYISICIYVKBTA-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 2
101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
238000013459 approach Methods 0.000 description 2
239000011324 bead Substances 0.000 description 2
WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical class CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
230000007423 decrease Effects 0.000 description 2
KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000010494 dissociation reaction Methods 0.000 description 2
230000005593 dissociations Effects 0.000 description 2
239000011491 glass wool Substances 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
150000005673 monoalkenes Chemical class 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000002459 porosimetry Methods 0.000 description 2
238000012545 processing Methods 0.000 description 2
SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
230000001172 regenerating effect Effects 0.000 description 2
238000009877 rendering Methods 0.000 description 2
GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 2
238000007655 standard test method Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 description 1
QYCHOJSGDMANGO-UHFFFAOYSA-N 1-(chloromethylsulfonyl)ethane Chemical compound CCS(=O)(=O)CCl QYCHOJSGDMANGO-UHFFFAOYSA-N 0.000 description 1
YBJCDTIWNDBNTM-UHFFFAOYSA-N 1-methylsulfonylethane Chemical compound CCS(C)(=O)=O YBJCDTIWNDBNTM-UHFFFAOYSA-N 0.000 description 1
JEXYCADTAFPULN-UHFFFAOYSA-N 1-propylsulfonylpropane Chemical compound CCCS(=O)(=O)CCC JEXYCADTAFPULN-UHFFFAOYSA-N 0.000 description 1
IDOFMGSESVXXQI-UHFFFAOYSA-N 2,4,6-tritert-butylpyridine Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=NC(C(C)(C)C)=C1 IDOFMGSESVXXQI-UHFFFAOYSA-N 0.000 description 1
WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 1
IBTGEEMBZJBBSH-UHFFFAOYSA-N 2,6-dimethoxypyridine Chemical compound COC1=CC=CC(OC)=N1 IBTGEEMBZJBBSH-UHFFFAOYSA-N 0.000 description 1
HNMMGGMSQSKUMF-UHFFFAOYSA-N 2,6-diphenoxypyridine Chemical compound C=1C=CC(OC=2C=CC=CC=2)=NC=1OC1=CC=CC=C1 HNMMGGMSQSKUMF-UHFFFAOYSA-N 0.000 description 1
IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 description 1
MEAAWTRWNWSLPF-UHFFFAOYSA-N 2-phenoxypyridine Chemical compound C=1C=CC=NC=1OC1=CC=CC=C1 MEAAWTRWNWSLPF-UHFFFAOYSA-N 0.000 description 1
CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
241000286904 Leptothecata Species 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229920005601 base polymer Polymers 0.000 description 1
229910001570 bauxite Inorganic materials 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000001273 butane Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
235000011116 calcium hydroxide Nutrition 0.000 description 1
239000003575 carbonaceous material Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
239000013529 heat transfer fluid Substances 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229920003228 poly(4-vinyl pyridine) Polymers 0.000 description 1
239000001294 propane Substances 0.000 description 1
238000005086 pumping Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
238000012546 transfer Methods 0.000 description 1
239000011787 zinc oxide Substances 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
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- 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
- B01J38/00—Regeneration or reactivation of catalysts, in general
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C9/00—Aliphatic saturated hydrocarbons
- C07C9/14—Aliphatic saturated hydrocarbons with five to fifteen carbon atoms
- C07C9/16—Branched-chain hydrocarbons
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Treatment Of Liquids With Adsorbents In General (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)

CA002099359A 1992-08-27 1993-06-28 Alkylation catalyst regeneration Expired - Fee Related CA2099359C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US93580792A	1992-08-27	1992-08-27
US07/935,807		1992-08-27

Publications (2)

Publication Number	Publication Date
CA2099359A1 CA2099359A1 (en)	1994-02-28
CA2099359C true CA2099359C (en)	1999-06-15

Family

ID=25467688

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002099359A Expired - Fee Related CA2099359C (en)	1992-08-27	1993-06-28	Alkylation catalyst regeneration

Country Status (9)

Country	Link
JP (1)	JP3172338B2 (de)
KR (1)	KR100237143B1 (de)
CN (1)	CN1039311C (de)
AU (1)	AU652516B2 (de)
BR (1)	BR9303500A (de)
CA (1)	CA2099359C (de)
MX (1)	MX9305045A (de)
TW (1)	TW297782B (de)
ZA (1)	ZA935776B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1265051B1 (it) *	1993-08-06	1996-10-28	Eniricerche Spa	Processo per l'alchilazione di idrocarburi alifatici con olefine
US7449521B2 (en)	2003-03-28	2008-11-11	Kaneka Corporation	Acrylic elastomer composition
CN112569873B (zh) *	2019-09-27	2022-07-15	中国石油化工股份有限公司	固体酸烷基化反应与再生装置及固体酸烷基化反应与再生方法
KR20250073619A (ko)	2022-09-30	2025-05-27	티제이엠 디자인 코포레이션	작업용품용 홀더

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3975164A (en) *	1975-02-05	1976-08-17	Phillips Petroleum Company	Apparatus for purifying HF catalyst in an alkylation process
US4663026A (en) *	1984-11-28	1987-05-05	Mobil Oil Corporation	Solvent extraction and purification of acid soluble oil from an HF alkylation unit

1993
- 1993-06-28 CA CA002099359A patent/CA2099359C/en not_active Expired - Fee Related
- 1993-08-05 AU AU44440/93A patent/AU652516B2/en not_active Ceased
- 1993-08-05 TW TW082106276A patent/TW297782B/zh active
- 1993-08-09 ZA ZA935776A patent/ZA935776B/xx unknown
- 1993-08-19 MX MX9305045A patent/MX9305045A/es not_active IP Right Cessation
- 1993-08-20 JP JP20652093A patent/JP3172338B2/ja not_active Expired - Fee Related
- 1993-08-21 KR KR1019930016355A patent/KR100237143B1/ko not_active Expired - Fee Related
- 1993-08-26 BR BR9303500A patent/BR9303500A/pt not_active IP Right Cessation
- 1993-08-26 CN CN93116784A patent/CN1039311C/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
BR9303500A (pt)	1994-03-15
AU652516B2 (en)	1994-08-25
AU4444093A (en)	1994-03-03
TW297782B (de)	1997-02-11
CN1083417A (zh)	1994-03-09
JP3172338B2 (ja)	2001-06-04
CN1039311C (zh)	1998-07-29
CA2099359A1 (en)	1994-02-28
MX9305045A (es)	1994-06-30
ZA935776B (en)	1994-03-08
KR940003607A (ko)	1994-03-12
JPH06190288A (ja)	1994-07-12
KR100237143B1 (ko)	2000-01-15

Legal Events

Date	Code	Title	Description
1993-06-23	EEER	Examination request
2003-06-30	MKLA	Lapsed
2023-05-26	MKLA	Lapsed	Effective date: 20030630

Publication	Publication Date	Title
EP0568089A1 (de)	1993-11-03	Isoparaffin/Olefin Alkylierungsprozess
US5306859A (en)	1994-04-26	Alkylation catalyst regeneration utilizing polyvinylpyridine and amine substituted styrene divinylbenzene copolymer contact materials
EP0590631B1 (de)	1996-12-27	Regenerierung eines Alkylierungskatalysators
AU652515B2 (en)	1994-08-25	A process for removing an acid soluble-oil from a sulfone-containing mixture such as recovered from alkylation catalyst
CA2092928C (en)	2000-02-22	Alkylation catalyst regeneration
CA2099359C (en)	1999-06-15	Alkylation catalyst regeneration
US5264649A (en)	1993-11-23	Alkylation catalyst regeneration
EP0622348B1 (de)	1996-09-11	Verfahren zur Regenerierung eines Alkylierungsakatalysators
EP0595755B1 (de)	1996-04-24	Verfahren zur Wiedergewinnung von sauren Katalysatoren in säurekatalysierten Prozessen
US5463162A (en)	1995-10-31	Alkylation catalyst regeneration
US5753575A (en)	1998-05-19	Method for regenerating a hydrogen fluoride and sulfone alkylation catalyst