CA1094581A - Catalytic alkylation process - Google Patents
Catalytic alkylation processInfo
- Publication number
- CA1094581A CA1094581A CA269,953A CA269953A CA1094581A CA 1094581 A CA1094581 A CA 1094581A CA 269953 A CA269953 A CA 269953A CA 1094581 A CA1094581 A CA 1094581A
- Authority
- CA
- Canada
- Prior art keywords
- effluent
- liquid
- isobutane
- stream
- cooling
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 52
- 230000008569 process Effects 0.000 title claims abstract description 52
- 238000003442 catalytic alkylation reaction Methods 0.000 title claims abstract description 5
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims abstract description 93
- 239000007788 liquid Substances 0.000 claims abstract description 75
- 239000001282 iso-butane Substances 0.000 claims abstract description 46
- 238000001816 cooling Methods 0.000 claims abstract description 36
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 32
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 28
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 28
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 27
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 23
- 150000001336 alkenes Chemical class 0.000 claims abstract description 21
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 12
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000003377 acid catalyst Substances 0.000 claims description 18
- 230000029936 alkylation Effects 0.000 claims description 18
- 238000000926 separation method Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 13
- 239000001294 propane Substances 0.000 claims description 13
- 230000008016 vaporization Effects 0.000 claims description 9
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 230000006872 improvement Effects 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- 238000009834 vaporization Methods 0.000 claims description 3
- 238000010924 continuous production Methods 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 229960002050 hydrofluoric acid Drugs 0.000 claims 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 235000013849 propane Nutrition 0.000 description 5
- 239000001273 butane Substances 0.000 description 4
- 239000002826 coolant Substances 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- -1 - propanes Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 101150073597 DLST gene Proteins 0.000 description 1
- 101100295675 Dictyostelium discoideum odhB gene Proteins 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 240000004543 Vicia ervilia Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
- C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
- C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
- C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
-
- 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)
- Liquid Carbonaceous Fuels (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65034176A | 1976-01-19 | 1976-01-19 | |
| US650,341 | 1976-01-19 | ||
| US05/742,949 US4130593A (en) | 1976-01-19 | 1976-11-18 | Alkylation process utilizing the hydrocarbon phase from a reactor for condensing a vaporous distillation effluent |
| US742,949 | 1976-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1094581A true CA1094581A (en) | 1981-01-27 |
Family
ID=27095834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA269,953A Expired CA1094581A (en) | 1976-01-19 | 1977-01-18 | Catalytic alkylation process |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS52102207A (cs) |
| AR (1) | AR224094A1 (cs) |
| AT (1) | AT362040B (cs) |
| AU (1) | AU505525B2 (cs) |
| BR (1) | BR7700336A (cs) |
| CA (1) | CA1094581A (cs) |
| CS (1) | CS199659B2 (cs) |
| DD (1) | DD128763A5 (cs) |
| DE (1) | DE2701170A1 (cs) |
| DK (1) | DK18277A (cs) |
| FR (1) | FR2338236A1 (cs) |
| IN (1) | IN145697B (cs) |
| IT (1) | IT1091806B (cs) |
| MX (1) | MX143073A (cs) |
| NL (1) | NL7700528A (cs) |
| NO (1) | NO770144L (cs) |
| PT (1) | PT66084B (cs) |
| RO (1) | RO79194A (cs) |
| SE (1) | SE424441B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1103704A (en) * | 1977-10-26 | 1981-06-23 | Richard H. Jones | Catalytic alkylation process |
| US4189616A (en) * | 1978-02-02 | 1980-02-19 | Phillips Petroleum Company | Maximum utilization of energy in isoparaffin recycle in alkylation |
| JPS5538284U (cs) * | 1978-09-05 | 1980-03-12 | ||
| US4214114A (en) * | 1979-01-26 | 1980-07-22 | Uop Inc. | Isoparaffin-olefin alkylation utilizing evaporative cooling in a reactor-depropanizer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3544652A (en) * | 1966-07-15 | 1970-12-01 | Pullman Inc | Alkylation with sulfuric acid |
-
1977
- 1977-01-13 DE DE19772701170 patent/DE2701170A1/de not_active Withdrawn
- 1977-01-15 IN IN55/CAL/77A patent/IN145697B/en unknown
- 1977-01-17 DD DD7700196967A patent/DD128763A5/xx unknown
- 1977-01-17 MX MX167718A patent/MX143073A/es unknown
- 1977-01-18 NO NO770144A patent/NO770144L/no unknown
- 1977-01-18 CA CA269,953A patent/CA1094581A/en not_active Expired
- 1977-01-18 AR AR266229A patent/AR224094A1/es active
- 1977-01-18 AT AT25677A patent/AT362040B/de not_active IP Right Cessation
- 1977-01-18 BR BR7700336A patent/BR7700336A/pt unknown
- 1977-01-18 IT IT19408/77A patent/IT1091806B/it active
- 1977-01-18 FR FR7701295A patent/FR2338236A1/fr active Granted
- 1977-01-18 PT PT66084A patent/PT66084B/pt unknown
- 1977-01-18 DK DK18277A patent/DK18277A/da not_active Application Discontinuation
- 1977-01-19 NL NL7700528A patent/NL7700528A/xx not_active Application Discontinuation
- 1977-01-19 AU AU21456/77A patent/AU505525B2/en not_active Expired
- 1977-01-19 SE SE7700557A patent/SE424441B/xx unknown
- 1977-01-19 CS CS77366A patent/CS199659B2/cs unknown
- 1977-01-19 RO RO7789089A patent/RO79194A/ro unknown
- 1977-01-19 JP JP482377A patent/JPS52102207A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| PT66084B (en) | 1978-06-26 |
| SE7700557L (sv) | 1977-07-20 |
| FR2338236A1 (fr) | 1977-08-12 |
| PT66084A (en) | 1977-02-01 |
| DK18277A (da) | 1977-07-20 |
| CS199659B2 (en) | 1980-07-31 |
| DE2701170A1 (de) | 1977-07-28 |
| AU505525B2 (en) | 1979-11-22 |
| NO770144L (no) | 1977-07-20 |
| AU2145677A (en) | 1978-07-27 |
| IN145697B (cs) | 1985-01-05 |
| JPS6121927B2 (cs) | 1986-05-29 |
| ATA25677A (de) | 1980-09-15 |
| JPS52102207A (en) | 1977-08-27 |
| NL7700528A (nl) | 1977-07-21 |
| FR2338236B1 (cs) | 1981-11-20 |
| MX143073A (es) | 1981-03-10 |
| SE424441B (sv) | 1982-07-19 |
| DD128763A5 (de) | 1977-12-07 |
| RO79194A (ro) | 1982-10-26 |
| BR7700336A (pt) | 1977-09-20 |
| AT362040B (de) | 1981-04-27 |
| AR224094A1 (es) | 1981-10-30 |
| IT1091806B (it) | 1985-07-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |