CA1062229A - Procede de recuperation d'un catalyseur d'alkoylation - Google Patents

Procede de recuperation d'un catalyseur d'alkoylation

Info

Publication number: CA1062229A
Authority: CA; Canada
Prior art keywords: acid; catalyst; zone; spent; sulfuric acid
Prior art date: 1974-12-30
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

Application number

CA235,544A

Other languages

English (en)

Other versions

CA235544S (en

Inventor

James W. Brockington

Richard H. Bennett

Byron Von Klock

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.)

Texaco Development Corp

Original Assignee

Texaco Development Corp

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.)

1974-12-30

Filing date

1975-09-16

Publication date

1979-09-11

1975-09-16 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1979-09-11 Application granted granted Critical

1979-09-11 Publication of CA1062229A publication Critical patent/CA1062229A/fr

Status Expired legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 127
238000005804 alkylation reaction Methods 0.000 title claims abstract description 46
230000029936 alkylation Effects 0.000 title claims abstract description 39
238000011084 recovery Methods 0.000 title description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 80
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 49
238000000034 method Methods 0.000 claims abstract description 46
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims abstract description 39
230000008569 process Effects 0.000 claims abstract description 37
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 25
229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 25
150000002222 fluorine compounds Chemical class 0.000 claims abstract description 12
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 49
229940032330 sulfuric acid Drugs 0.000 claims description 36
125000001153 fluoro group Chemical group F* 0.000 claims description 28
239000007791 liquid phase Substances 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 24
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 22
238000005336 cracking Methods 0.000 claims description 21
230000007062 hydrolysis Effects 0.000 claims description 14
238000006460 hydrolysis reaction Methods 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 13
239000012808 vapor phase Substances 0.000 claims description 10
238000010521 absorption reaction Methods 0.000 claims description 9
230000008929 regeneration Effects 0.000 claims description 8
238000011069 regeneration method Methods 0.000 claims description 8
239000007788 liquid Substances 0.000 claims description 7
238000000926 separation method Methods 0.000 claims description 6
239000007790 solid phase Substances 0.000 claims description 4
QETIQOSRQCIHEC-UHFFFAOYSA-N sulfuric acid sulfurofluoridic acid Chemical compound FS(=O)(=O)O.S(=O)(=O)(O)O QETIQOSRQCIHEC-UHFFFAOYSA-N 0.000 claims description 4
239000000463 material Substances 0.000 abstract description 16
238000005292 vacuum distillation Methods 0.000 abstract 1
238000004821 distillation Methods 0.000 description 25
239000003463 adsorbent Substances 0.000 description 23
239000003377 acid catalyst Substances 0.000 description 14
229930195733 hydrocarbon Natural products 0.000 description 13
239000010802 sludge Substances 0.000 description 13
230000000694 effects Effects 0.000 description 12
238000001179 sorption measurement Methods 0.000 description 12
150000002430 hydrocarbons Chemical class 0.000 description 10
239000004215 Carbon black (E152) Substances 0.000 description 7
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
-1 olefin hydrocarbons Chemical class 0.000 description 6
239000000376 reactant Substances 0.000 description 6
238000007792 addition Methods 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
238000011282 treatment Methods 0.000 description 5
150000001336 alkenes Chemical class 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
229910001570 bauxite Inorganic materials 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
238000011221 initial treatment Methods 0.000 description 4
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000002245 particle Substances 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
230000029087 digestion Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 3
229910052720 vanadium Inorganic materials 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000007429 general method Methods 0.000 description 2
239000001282 iso-butane Substances 0.000 description 2
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011819 refractory material Substances 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 1
KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
229940037003 alum Drugs 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052593 corundum Inorganic materials 0.000 description 1
239000010431 corundum Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000008570 general process Effects 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
238000004904 shortening Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Landscapes

Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA235,544A 1974-12-30 1975-09-16 Procede de recuperation d'un catalyseur d'alkoylation Expired CA1062229A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US53763174A	1974-12-30	1974-12-30

Publications (1)

Publication Number	Publication Date
CA1062229A true CA1062229A (fr)	1979-09-11

Family

ID=24143462

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA235,544A Expired CA1062229A (fr)	1974-12-30	1975-09-16	Procede de recuperation d'un catalyseur d'alkoylation

Country Status (1)

Country	Link
CA (1)	CA1062229A (fr)

1975
- 1975-09-16 CA CA235,544A patent/CA1062229A/fr not_active Expired

Publication	Publication Date	Title
AU2001279318B2 (en)	2006-03-30	Process for removing low amounts of organic sulfur from hydrocarbon fuels
EP0271823B1 (fr)	1991-02-27	Procédé pour éliminer le retour de disulfures dans un procédé d'extraction de mercaptan
JP2548934B2 (ja)	1996-10-30	ヒドロキシ含有アルキル芳香族化合物の製造法
US4033899A (en)	1977-07-05	Alkylation fluosulfonic-sulfuric acid catalyst recovery process with silica-alumina removal of fluoride compounds
KR20010033643A (ko)	2001-04-25	불화금속에 의한 삼불화붕소의 제거 회수방법 및 이를이용한 폴리올레핀의 제조방법
CA1063589A (fr)	1979-10-02	Methode de regeneration du catalyseur d'alkylation
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AU654089B2 (en)	1994-10-20	Process for regenerating a catalyst mixture containing a sulfone and hydrogen halide component
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CA1062229A (fr)	1979-09-11	Procede de recuperation d'un catalyseur d'alkoylation
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CA2092928C (fr)	2000-02-22	Regeneration d'un catalyseur de l'alkylation
US2287732A (en)	1942-06-23	Process for reclaiming sulphuric acid
US4180696A (en)	1979-12-25	Converting reactive impurities in isobutane charge stream with catalyst phase in sulfuric acid alkylation
US2377396A (en)	1945-06-05	Process for recovery of boron halides
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US2839365A (en)	1958-06-17	Treatment of sulfuric acid sludge
US5501847A (en)	1996-03-26	Process for purifying impure sulphuric acid
US3607035A (en)	1971-09-21	Process for treating a sulfuric acid-olefinic hydrocarbon mixture
CA2446979A1 (fr)	2002-11-21	Alkylation respectueuse de l'environnement d'hydrocarbures aliphatiques et aromatiques avec des olefines utilisant des catalyseurs solides hf equivalents
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