DE1593597C3 - Verfahren zum Alkylieren eines Isoparaffins - Google Patents
Verfahren zum Alkylieren eines IsoparaffinsInfo
- Publication number
- DE1593597C3 DE1593597C3 DE19661593597 DE1593597A DE1593597C3 DE 1593597 C3 DE1593597 C3 DE 1593597C3 DE 19661593597 DE19661593597 DE 19661593597 DE 1593597 A DE1593597 A DE 1593597A DE 1593597 C3 DE1593597 C3 DE 1593597C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- alkylation
- sulfuric acid
- olefin
- zone
- 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
- 230000002152 alkylating effect Effects 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 8
- 239000002253 acid Substances 0.000 claims description 108
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 85
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 74
- 238000005804 alkylation reaction Methods 0.000 claims description 63
- 230000029936 alkylation Effects 0.000 claims description 59
- 150000001336 alkenes Chemical class 0.000 claims description 57
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 54
- 229930195733 hydrocarbon Natural products 0.000 claims description 43
- 239000001282 iso-butane Substances 0.000 claims description 42
- 150000002430 hydrocarbons Chemical class 0.000 claims description 40
- 239000004215 Carbon black (E152) Substances 0.000 claims description 38
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 38
- 238000010521 absorption reaction Methods 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 25
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000000605 extraction Methods 0.000 claims description 18
- 238000011084 recovery Methods 0.000 claims description 17
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 16
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 16
- -1 hydrocarbon alkyl sulfate Chemical class 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 9
- 239000003377 acid catalyst Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000012535 impurity Substances 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000446 fuel Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 238000005457 optimization Methods 0.000 claims 1
- 239000012188 paraffin wax Substances 0.000 claims 1
- IZGYIFFQBZWOLJ-CKAACLRMSA-N phaseic acid Chemical compound C1C(=O)C[C@@]2(C)OC[C@]1(C)[C@@]2(O)C=CC(/C)=C\C(O)=O IZGYIFFQBZWOLJ-CKAACLRMSA-N 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 239000006096 absorbing agent Substances 0.000 description 54
- 239000012071 phase Substances 0.000 description 40
- 239000007789 gas Substances 0.000 description 19
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000000284 extract Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- TYRGSDXYMNTMML-UHFFFAOYSA-N propyl hydrogen sulfate Chemical compound CCCOS(O)(=O)=O TYRGSDXYMNTMML-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 8
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 8
- 239000001294 propane Substances 0.000 description 8
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 238000010306 acid treatment Methods 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- JTXAHXNXKFGXIT-UHFFFAOYSA-N propane;prop-1-ene Chemical group CCC.CC=C JTXAHXNXKFGXIT-UHFFFAOYSA-N 0.000 description 6
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229910021653 sulphate ion Inorganic materials 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- 235000013844 butane Nutrition 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- JYCKNDWZDXGNBW-UHFFFAOYSA-N dipropyl sulfate Chemical compound CCCOS(=O)(=O)OCCC JYCKNDWZDXGNBW-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000001273 butane Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000011027 product recovery Methods 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- DOYJTLUPPPUSMD-UHFFFAOYSA-N 4,5-dimethyloctane Chemical compound CCCC(C)C(C)CCC DOYJTLUPPPUSMD-UHFFFAOYSA-N 0.000 description 1
- 241001508691 Martes zibellina Species 0.000 description 1
- 101100314144 Mus musculus Tnip1 gene Proteins 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 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 |
|---|---|---|---|
| US51090465A | 1965-12-01 | 1965-12-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1593597A1 DE1593597A1 (de) | 1970-10-08 |
| DE1593597B2 DE1593597B2 (de) | 1975-03-06 |
| DE1593597C3 true DE1593597C3 (de) | 1975-10-16 |
Family
ID=24032662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593597 Expired DE1593597C3 (de) | 1965-12-01 | 1966-12-01 | Verfahren zum Alkylieren eines Isoparaffins |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE690539A (enrdf_load_stackoverflow) |
| DE (1) | DE1593597C3 (enrdf_load_stackoverflow) |
| FR (1) | FR1502507A (enrdf_load_stackoverflow) |
| GB (1) | GB1165759A (enrdf_load_stackoverflow) |
| NL (1) | NL150763B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4130593A (en) | 1976-01-19 | 1978-12-19 | The Standard Oil Company | Alkylation process utilizing the hydrocarbon phase from a reactor for condensing a vaporous distillation effluent |
| CN115138302B (zh) * | 2021-03-31 | 2023-05-26 | 中国石油天然气股份有限公司 | 液体酸烷基化反应工艺及反应系统 |
-
1966
- 1966-11-23 GB GB5252666A patent/GB1165759A/en not_active Expired
- 1966-11-29 NL NL6616790A patent/NL150763B/xx unknown
- 1966-11-30 FR FR85637A patent/FR1502507A/fr not_active Expired
- 1966-12-01 DE DE19661593597 patent/DE1593597C3/de not_active Expired
- 1966-12-01 BE BE690539D patent/BE690539A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1593597A1 (de) | 1970-10-08 |
| NL6616790A (enrdf_load_stackoverflow) | 1967-06-02 |
| GB1165759A (en) | 1969-10-01 |
| BE690539A (enrdf_load_stackoverflow) | 1967-06-01 |
| FR1502507A (fr) | 1967-11-18 |
| DE1593597B2 (de) | 1975-03-06 |
| NL150763B (nl) | 1976-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |