DE1593599B2 - Verfahren zur alkylierung eines isoparaffins - Google Patents
Verfahren zur alkylierung eines isoparaffinsInfo
- Publication number
- DE1593599B2 DE1593599B2 DE1966T0032788 DET0032788A DE1593599B2 DE 1593599 B2 DE1593599 B2 DE 1593599B2 DE 1966T0032788 DE1966T0032788 DE 1966T0032788 DE T0032788 A DET0032788 A DE T0032788A DE 1593599 B2 DE1593599 B2 DE 1593599B2
- Authority
- DE
- Germany
- Prior art keywords
- isobutylene
- alkylation
- acid
- sulfuric acid
- phase
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 20
- 230000002152 alkylating effect Effects 0.000 title description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 111
- 239000002253 acid Substances 0.000 claims description 74
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 72
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 60
- 238000005804 alkylation reaction Methods 0.000 claims description 59
- 230000029936 alkylation Effects 0.000 claims description 58
- 150000001336 alkenes Chemical class 0.000 claims description 37
- 239000001282 iso-butane Substances 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 29
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 26
- 238000010521 absorption reaction Methods 0.000 claims description 23
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 23
- 229930195733 hydrocarbon Natural products 0.000 claims description 20
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- 150000002430 hydrocarbons Chemical class 0.000 claims description 17
- 230000002378 acidificating effect Effects 0.000 claims description 12
- 239000012535 impurity Substances 0.000 claims description 9
- -1 olefin hydrocarbon Chemical class 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- 238000001179 sorption measurement Methods 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 description 29
- 239000006096 absorbing agent Substances 0.000 description 26
- 150000008050 dialkyl sulfates Chemical class 0.000 description 24
- 239000012071 phase Substances 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000284 extract Substances 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 10
- 239000007791 liquid phase Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000012808 vapor phase Substances 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 4
- QNPCBWPVEZKWQU-UHFFFAOYSA-N 2-methylprop-1-ene;sulfuric acid Chemical compound CC(C)=C.OS(O)(=O)=O QNPCBWPVEZKWQU-UHFFFAOYSA-N 0.000 description 3
- JVNPHYVDWYJFES-UHFFFAOYSA-N 2-methylpropyl hydrogen sulfate Chemical compound CC(C)COS(O)(=O)=O JVNPHYVDWYJFES-UHFFFAOYSA-N 0.000 description 3
- 238000010306 acid treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004523 catalytic cracking Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 238000004519 manufacturing process Methods 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
- 238000004064 recycling Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YHGBWUVWEKLPFZ-UHFFFAOYSA-N 2,9-dimethyldeca-2,8-diene Chemical group CC(C)=CCCCCC=C(C)C YHGBWUVWEKLPFZ-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000013022 venting 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51644865A | 1965-12-27 | 1965-12-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1593599A1 DE1593599A1 (de) | 1970-09-03 |
| DE1593599B2 true DE1593599B2 (de) | 1976-12-09 |
Family
ID=24055640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1966T0032788 Granted DE1593599B2 (de) | 1965-12-27 | 1966-12-19 | Verfahren zur alkylierung eines isoparaffins |
Country Status (3)
-
1966
- 1966-12-13 GB GB5586166A patent/GB1160088A/en not_active Expired
- 1966-12-19 DE DE1966T0032788 patent/DE1593599B2/de active Granted
- 1966-12-22 BE BE691619D patent/BE691619A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE691619A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-22 |
| DE1593599A1 (de) | 1970-09-03 |
| GB1160088A (en) | 1969-07-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |