CA1108653A - Procede d'alkylation a l'aide de hf - Google Patents
Procede d'alkylation a l'aide de hfInfo
- Publication number
- CA1108653A CA1108653A CA326,099A CA326099A CA1108653A CA 1108653 A CA1108653 A CA 1108653A CA 326099 A CA326099 A CA 326099A CA 1108653 A CA1108653 A CA 1108653A
- Authority
- CA
- Canada
- Prior art keywords
- isoparaffin
- concentrate
- acid
- reaction
- feed stream
- 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
- 238000005804 alkylation reaction Methods 0.000 title claims abstract description 38
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims abstract description 84
- 238000006243 chemical reaction Methods 0.000 claims abstract description 50
- 239000001282 iso-butane Substances 0.000 claims abstract description 41
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000011541 reaction mixture Substances 0.000 claims abstract description 22
- 239000012141 concentrate Substances 0.000 claims abstract description 15
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 235000013844 butane Nutrition 0.000 claims abstract description 5
- 230000029936 alkylation Effects 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 26
- 229930195733 hydrocarbon Natural products 0.000 claims description 25
- 150000002430 hydrocarbons Chemical class 0.000 claims description 25
- 239000004215 Carbon black (E152) Substances 0.000 claims description 21
- 239000012188 paraffin wax Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
- 239000012080 ambient air Substances 0.000 claims description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 6
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 5
- 230000008016 vaporization Effects 0.000 claims description 2
- 235000013847 iso-butane Nutrition 0.000 abstract description 40
- 239000002253 acid Substances 0.000 abstract description 37
- 239000000498 cooling water Substances 0.000 abstract description 12
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 238000011109 contamination Methods 0.000 abstract 1
- 238000005194 fractionation Methods 0.000 abstract 1
- 229940035415 isobutane Drugs 0.000 description 38
- 239000000047 product Substances 0.000 description 23
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 239000003570 air Substances 0.000 description 6
- 239000000306 component Substances 0.000 description 6
- 239000002826 coolant Substances 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 235000013849 propane Nutrition 0.000 description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- -1 l-butene Natural products 0.000 description 4
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- 208000036366 Sensation of pressure Diseases 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000005057 refrigeration Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- YUHZIUAREWNXJT-UHFFFAOYSA-N (2-fluoropyridin-3-yl)boronic acid Chemical class OB(O)C1=CC=CN=C1F YUHZIUAREWNXJT-UHFFFAOYSA-N 0.000 description 1
- GRYSXUXXBDSYRT-WOUKDFQISA-N (2r,3r,4r,5r)-2-(hydroxymethyl)-4-methoxy-5-[6-(methylamino)purin-9-yl]oxolan-3-ol Chemical compound C1=NC=2C(NC)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OC GRYSXUXXBDSYRT-WOUKDFQISA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical class CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 206010041662 Splinter Diseases 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004231 fluid catalytic cracking Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US899,753 | 1978-04-24 | ||
| US899,601 | 1978-04-24 | ||
| US05/899,601 US4167535A (en) | 1978-04-24 | 1978-04-24 | Isoparaffin-olefin alkylation utilizing liquefied normal paraffin concentrate in the reaction vessel |
| US05/899,753 US4139573A (en) | 1978-04-24 | 1978-04-24 | Isoparaffin-olefin alkylation utilizing vaporization of normal paraffin to control the reaction temperature |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1108653A true CA1108653A (fr) | 1981-09-08 |
Family
ID=27129243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA326,099A Expired CA1108653A (fr) | 1978-04-24 | 1979-04-23 | Procede d'alkylation a l'aide de hf |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU530515B2 (fr) |
| CA (1) | CA1108653A (fr) |
| DE (1) | DE2916488C2 (fr) |
| EG (1) | EG13914A (fr) |
| ES (1) | ES479840A1 (fr) |
| FR (1) | FR2424241A1 (fr) |
| GB (1) | GB2023166B (fr) |
| IT (1) | IT1112590B (fr) |
| MX (1) | MX151853A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5382744A (en) * | 1993-07-12 | 1995-01-17 | Phillips Petroleum Company | Control of synthetic isopentane production during alkylation of amylenes |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2409389A (en) * | 1944-09-28 | 1946-10-15 | Phillips Petroleum Co | Alkylation process |
| US2949494A (en) * | 1954-08-16 | 1960-08-16 | Stratford Eng Corp | Alkylation of hydrocarbons utilizing evaporative cooling |
| US2906796A (en) * | 1956-05-23 | 1959-09-29 | Stratford Eng Corp | Combination process of effluent refrigeration and closed cycle refrigeration |
| US3080438A (en) * | 1960-01-28 | 1963-03-05 | Phillips Petroleum Co | Catalytic alkylation process |
| US3846505A (en) * | 1972-03-20 | 1974-11-05 | Universal Oil Prod Co | Hf alkylation including recycle and further alkylation of the alkylate-containing hydrocarbon |
| US3855344A (en) * | 1973-02-02 | 1974-12-17 | E Jones | Isobutane flashing in the alkylation of c{11 {14 c{11 {0 olefin hydrocarbons with isobutane |
| US4139573A (en) * | 1978-04-24 | 1979-02-13 | Uop Inc. | Isoparaffin-olefin alkylation utilizing vaporization of normal paraffin to control the reaction temperature |
-
1979
- 1979-04-23 AU AU46353/79A patent/AU530515B2/en not_active Ceased
- 1979-04-23 CA CA326,099A patent/CA1108653A/fr not_active Expired
- 1979-04-23 ES ES479840A patent/ES479840A1/es not_active Expired
- 1979-04-23 GB GB7914123A patent/GB2023166B/en not_active Expired
- 1979-04-24 EG EG244/79A patent/EG13914A/xx active
- 1979-04-24 MX MX177414A patent/MX151853A/es unknown
- 1979-04-24 FR FR7910352A patent/FR2424241A1/fr active Granted
- 1979-04-24 DE DE2916488A patent/DE2916488C2/de not_active Expired
- 1979-04-24 IT IT22134/79A patent/IT1112590B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| AU530515B2 (en) | 1983-07-21 |
| IT7922134A0 (it) | 1979-04-24 |
| IT1112590B (it) | 1986-01-20 |
| GB2023166A (en) | 1979-12-28 |
| AU4635379A (en) | 1979-11-01 |
| GB2023166B (en) | 1982-06-23 |
| ES479840A1 (es) | 1979-11-16 |
| DE2916488A1 (de) | 1979-10-25 |
| DE2916488C2 (de) | 1982-12-23 |
| FR2424241A1 (fr) | 1979-11-23 |
| FR2424241B1 (fr) | 1982-03-05 |
| EG13914A (en) | 1982-09-30 |
| MX151853A (es) | 1985-04-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4139573A (en) | Isoparaffin-olefin alkylation utilizing vaporization of normal paraffin to control the reaction temperature | |
| US4555311A (en) | Integrated fractionation in the recovery of alkylaromatic hydrocarbons | |
| US3780131A (en) | Isoparaffin alkylation with a lighter olefin and subsequently with a heavier olefin | |
| US4225740A (en) | Alkylation separation process | |
| US3911043A (en) | Plural stages of HF alkylation of isoparaffin with a mono-olefin | |
| US4243830A (en) | Alkylation process | |
| US4209656A (en) | Sulfuric acid catalyzed alkylation process | |
| US2366736A (en) | Alkylation of isoparaffins | |
| CA1108653A (fr) | Procede d'alkylation a l'aide de hf | |
| US4167535A (en) | Isoparaffin-olefin alkylation utilizing liquefied normal paraffin concentrate in the reaction vessel | |
| US4239931A (en) | HF Alkylatior process | |
| US3544651A (en) | Recycling acid streams to different alkylation reactions | |
| CA1240341A (fr) | Alkylation d'acide fluorhydrique avec recyclage du produit par recours a deux reacteurs | |
| US3370003A (en) | Method for separating light hydrocarbon components | |
| US3364139A (en) | Method for separating isobutane from an alkylate effluent | |
| US3007983A (en) | Alkylation process | |
| US4280880A (en) | Method of operating an isostripper column | |
| US3775510A (en) | Refrigerating cooled recycled isobutane in alkylation | |
| US3830865A (en) | Alkylation process using hydrogen fluoride catalyst | |
| US4249030A (en) | Alkylation process | |
| US4059649A (en) | Cooling of recycle hydrocarbon and/or alkylate product in isoparaffin-olefin alkylation | |
| US3594444A (en) | Process for separating hydrocarbons and hydrogen fluoride catalyst from the effluent of an isoparaffin-olefin alkylation reaction zone | |
| US3038948A (en) | Alkylation process | |
| US2322664A (en) | Production of motor fuels | |
| US3846505A (en) | Hf alkylation including recycle and further alkylation of the alkylate-containing hydrocarbon |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |