CA2169965C - Isoparaffin-olefin alkylation - Google Patents
Isoparaffin-olefin alkylation Download PDFInfo
- Publication number
- CA2169965C CA2169965C CA002169965A CA2169965A CA2169965C CA 2169965 C CA2169965 C CA 2169965C CA 002169965 A CA002169965 A CA 002169965A CA 2169965 A CA2169965 A CA 2169965A CA 2169965 C CA2169965 C CA 2169965C
- Authority
- CA
- Canada
- Prior art keywords
- stream
- aso
- isoparaffin
- dense
- sulfolane
- 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.)
- Expired - Fee Related
Links
- 238000005804 alkylation reaction Methods 0.000 title claims abstract description 32
- 230000029936 alkylation Effects 0.000 title claims abstract description 15
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- 238000009835 boiling Methods 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 14
- 239000012530 fluid Substances 0.000 claims abstract description 11
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000002152 alkylating effect Effects 0.000 claims abstract description 3
- 238000004064 recycling Methods 0.000 claims abstract description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 89
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 44
- 239000000047 product Substances 0.000 claims description 30
- 239000001282 iso-butane Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 239000006227 byproduct Substances 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- 238000010992 reflux Methods 0.000 abstract description 2
- 239000003377 acid catalyst Substances 0.000 abstract 1
- QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 description 50
- 239000012071 phase Substances 0.000 description 31
- 239000000203 mixture Substances 0.000 description 30
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 238000000926 separation method Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- MPCAJMNYNOGXPB-SLPGGIOYSA-N 1,5-anhydro-D-glucitol Chemical compound OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O MPCAJMNYNOGXPB-SLPGGIOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000003442 catalytic alkylation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
- C07C2/62—Catalytic processes with acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1206—Hydrogen fluoride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US111,221 | 1993-08-23 | ||
| US08/111,221 US5386076A (en) | 1992-02-11 | 1993-08-23 | Regeneration of HF-based alkylation catalyst |
| US117,274 | 1993-09-07 | ||
| US08/117,274 US5382746A (en) | 1992-02-11 | 1993-09-07 | Removal of light ASO in HF alkylation process |
| PCT/US1994/008688 WO1995006017A1 (en) | 1993-08-23 | 1994-08-01 | Isoparaffin-olefin alkylation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2169965A1 CA2169965A1 (en) | 1995-03-02 |
| CA2169965C true CA2169965C (en) | 2002-04-09 |
Family
ID=26808738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002169965A Expired - Fee Related CA2169965C (en) | 1993-08-23 | 1994-08-01 | Isoparaffin-olefin alkylation |
Country Status (5)
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5264651A (en) * | 1992-02-11 | 1993-11-23 | Mobil Oil Corporation | Method for regenerating HF/sulfolane alkylation catalyst |
| US5264652A (en) * | 1992-02-11 | 1993-11-23 | Mobil Oil Corporation | Method for separating conjunct polymeric byproducts from mixture containing hydrofluoric acid and a sulfone |
| US5262579A (en) * | 1992-02-11 | 1993-11-16 | Mobil Oil Corporation | Separation of sulfolane from conjunct polymeric byproducts |
| US5191150A (en) * | 1992-02-11 | 1993-03-02 | Mobil Oil Corporation | Method for separating conjunct polymeric byproducts from mixture containing hydrofluoric acid and a sulfone |
| US5276243A (en) * | 1992-02-11 | 1994-01-04 | Mobil Oil Corporation | Sulfolane purification method |
| US5264650A (en) * | 1992-02-11 | 1993-11-23 | Mobil Oil Corporation | Sulfolane purification by hydrocarbon extraction |
| US5237122A (en) * | 1992-08-24 | 1993-08-17 | Phillips Petroleum Company | Alkylation catalyst regeneration |
| US5264647A (en) * | 1992-09-30 | 1993-11-23 | Phillips Petroleum Company | Alkylation catalyst regeneration |
| US5264649A (en) * | 1992-12-15 | 1993-11-23 | Phillips Petroleum Company | Alkylation catalyst regeneration |
-
1994
- 1994-08-01 JP JP7507588A patent/JPH09504270A/ja active Pending
- 1994-08-01 CA CA002169965A patent/CA2169965C/en not_active Expired - Fee Related
- 1994-08-01 DE DE69421284T patent/DE69421284T2/de not_active Expired - Fee Related
- 1994-08-01 WO PCT/US1994/008688 patent/WO1995006017A1/en active IP Right Grant
- 1994-08-01 EP EP94924543A patent/EP0715610B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0715610B1 (en) | 1999-10-20 |
| CA2169965A1 (en) | 1995-03-02 |
| AU677695B2 (en) | 1997-05-01 |
| WO1995006017A1 (en) | 1995-03-02 |
| JPH09504270A (ja) | 1997-04-28 |
| EP0715610A1 (en) | 1996-06-12 |
| EP0715610A4 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1996-07-03 |
| DE69421284T2 (de) | 2000-02-17 |
| DE69421284D1 (de) | 1999-11-25 |
| AU7478794A (en) | 1995-03-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5191150A (en) | Method for separating conjunct polymeric byproducts from mixture containing hydrofluoric acid and a sulfone | |
| US3763265A (en) | Recovery of ethylfluoride from isoparaffin ethylene and higher olefinalkylation by extractive distillation of propane containing stream obtained from alkylation effluent | |
| US5382746A (en) | Removal of light ASO in HF alkylation process | |
| US5264650A (en) | Sulfolane purification by hydrocarbon extraction | |
| US5262579A (en) | Separation of sulfolane from conjunct polymeric byproducts | |
| US5264652A (en) | Method for separating conjunct polymeric byproducts from mixture containing hydrofluoric acid and a sulfone | |
| US3919342A (en) | Propane recovery in HF alkylation utilizing extraction or two-phase condensation for removal of organic fluoride | |
| EP0715609B1 (en) | Isoparaffin-olefin alkylation | |
| US4371731A (en) | Alkylation process | |
| US5276243A (en) | Sulfolane purification method | |
| US5461183A (en) | Removal of ASO from HF/sulfolane alkylation catalyst | |
| US4513165A (en) | Alkylation process | |
| CA2169965C (en) | Isoparaffin-olefin alkylation | |
| US3204010A (en) | Defluorination process | |
| AU677695C (en) | Isoparaffin-olefin alkylation | |
| US3370003A (en) | Method for separating light hydrocarbon components | |
| WO1994013601A1 (en) | Method for regenerating hf/sulfolane alkylation catalyst | |
| US3972956A (en) | Avoiding pollution by HF catalyst residues in alkylation | |
| US3371032A (en) | Fractionation of alkylation effluent | |
| US3767727A (en) | Treatment of propane in hf alkylation with purified hf | |
| US2376051A (en) | Removal of light hydrocarbons from admixture with hydrogen fluoride | |
| US4009221A (en) | Hf recovery with alkyl fluoride formation and utility in alkylation | |
| US5767335A (en) | Method for preventing the accumulation of light ASO in the alkylation catalyst of alkylation process system | |
| US2487142A (en) | Treatment of hydrocarbons | |
| US2498789A (en) | Recovery of hydrogen fluoride |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20030801 |