DE2236049A1 - Mehrstufiges, mit schwefelsaeure katalysiertes alkylierungsverfahren - Google Patents
Mehrstufiges, mit schwefelsaeure katalysiertes alkylierungsverfahrenInfo
- Publication number
- DE2236049A1 DE2236049A1 DE2236049A DE2236049A DE2236049A1 DE 2236049 A1 DE2236049 A1 DE 2236049A1 DE 2236049 A DE2236049 A DE 2236049A DE 2236049 A DE2236049 A DE 2236049A DE 2236049 A1 DE2236049 A1 DE 2236049A1
- Authority
- DE
- Germany
- Prior art keywords
- stage
- sulfuric acid
- alkylation
- acid
- hydrocarbon
- 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.)
- Pending
Links
- 238000005804 alkylation reaction Methods 0.000 title claims description 182
- 239000002253 acid Substances 0.000 title claims description 107
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 2
- 229910052717 sulfur Inorganic materials 0.000 title description 2
- 239000011593 sulfur Substances 0.000 title description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 226
- 229930195733 hydrocarbon Natural products 0.000 claims description 91
- 150000002430 hydrocarbons Chemical class 0.000 claims description 86
- 239000004215 Carbon black (E152) Substances 0.000 claims description 74
- 239000012071 phase Substances 0.000 claims description 73
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 42
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 35
- 150000001336 alkenes Chemical class 0.000 claims description 29
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 27
- 230000029936 alkylation Effects 0.000 claims description 20
- 239000001282 iso-butane Substances 0.000 claims description 19
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 19
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 10
- 239000007791 liquid phase Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 5
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 description 31
- 230000005484 gravity Effects 0.000 description 9
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 7
- -1 dialkyl sulfates Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000004805 propylene group Chemical class [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 150000002611 lead compounds Chemical class 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- CBKSKPBBKQQLOM-UHFFFAOYSA-N [S].C(CCCCCCCC=C/CCCCCCCC)(=O)O Chemical compound [S].C(CCCCCCCC=C/CCCCCCCC)(=O)O CBKSKPBBKQQLOM-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005367 electrostatic precipitation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000007086 side reaction Methods 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
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16928271A | 1971-08-05 | 1971-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2236049A1 true DE2236049A1 (de) | 1973-02-15 |
Family
ID=22615001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2236049A Pending DE2236049A1 (de) | 1971-08-05 | 1972-07-22 | Mehrstufiges, mit schwefelsaeure katalysiertes alkylierungsverfahren |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3760028A (enExample) |
| JP (1) | JPS5228761B2 (enExample) |
| AU (1) | AU458735B2 (enExample) |
| BE (1) | BE787104A (enExample) |
| CA (1) | CA1005084A (enExample) |
| DE (1) | DE2236049A1 (enExample) |
| ES (1) | ES405565A1 (enExample) |
| FR (1) | FR2148147B1 (enExample) |
| GB (1) | GB1360555A (enExample) |
| IT (1) | IT963670B (enExample) |
| NL (1) | NL7210575A (enExample) |
| ZA (1) | ZA725046B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4503325B2 (ja) * | 2004-03-25 | 2010-07-14 | コスモ石油株式会社 | 硫酸式アルキレーション装置の運転方法 |
| WO2019060219A1 (en) * | 2017-09-20 | 2019-03-28 | E. I. Du Pont De Nemours And Company | ALKYLATION WITH MIXTURES OF OLEFINS |
| EP3788025A4 (en) * | 2018-05-04 | 2022-04-13 | Lummus Technology LLC | CASCADE OF HYDROCARBON AND REVERSE ACID IN ALKYLATION |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB540449A (en) * | 1940-03-08 | 1941-10-17 | Anglo Iranian Oil Co Ltd | Improvements relating to the production of saturated hydrocarbons |
| US3325391A (en) * | 1963-12-06 | 1967-06-13 | Petrolite Corp | Hydrocarbon purification |
| US3467729A (en) * | 1966-09-07 | 1969-09-16 | Tidewater Oil Co | Alkylation process |
-
0
- BE BE787104D patent/BE787104A/xx unknown
-
1971
- 1971-08-05 US US00169282A patent/US3760028A/en not_active Expired - Lifetime
-
1972
- 1972-07-21 GB GB3412672A patent/GB1360555A/en not_active Expired
- 1972-07-21 ZA ZA725046A patent/ZA725046B/xx unknown
- 1972-07-22 DE DE2236049A patent/DE2236049A1/de active Pending
- 1972-07-27 AU AU45061/72A patent/AU458735B2/en not_active Expired
- 1972-08-01 FR FR7227681A patent/FR2148147B1/fr not_active Expired
- 1972-08-01 CA CA148,474A patent/CA1005084A/en not_active Expired
- 1972-08-02 IT IT27801/72A patent/IT963670B/it active
- 1972-08-02 NL NL7210575A patent/NL7210575A/xx not_active Application Discontinuation
- 1972-08-03 JP JP47077333A patent/JPS5228761B2/ja not_active Expired
- 1972-08-04 ES ES405565A patent/ES405565A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3760028A (en) | 1973-09-18 |
| IT963670B (it) | 1974-01-21 |
| GB1360555A (en) | 1974-07-17 |
| CA1005084A (en) | 1977-02-08 |
| ES405565A1 (es) | 1975-08-01 |
| FR2148147A1 (enExample) | 1973-03-11 |
| JPS5228761B2 (enExample) | 1977-07-28 |
| ZA725046B (en) | 1974-02-27 |
| AU4506172A (en) | 1974-01-31 |
| BE787104A (fr) | 1973-02-02 |
| NL7210575A (enExample) | 1973-02-07 |
| FR2148147B1 (enExample) | 1976-05-14 |
| AU458735B2 (en) | 1975-03-06 |
| JPS4826702A (enExample) | 1973-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |