DE2227770A1 - Verfahren zur alkylierung von gasfoermigen azyklischen monoolefinen - Google Patents
Verfahren zur alkylierung von gasfoermigen azyklischen monoolefinenInfo
- Publication number
- DE2227770A1 DE2227770A1 DE2227770A DE2227770A DE2227770A1 DE 2227770 A1 DE2227770 A1 DE 2227770A1 DE 2227770 A DE2227770 A DE 2227770A DE 2227770 A DE2227770 A DE 2227770A DE 2227770 A1 DE2227770 A1 DE 2227770A1
- Authority
- DE
- Germany
- Prior art keywords
- alkylation
- mist
- acid
- sulfuric acid
- isobutane
- 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
- 238000000034 method Methods 0.000 title claims description 62
- 238000005804 alkylation reaction Methods 0.000 title claims description 42
- 230000029936 alkylation Effects 0.000 title claims description 35
- 230000008569 process Effects 0.000 title claims description 35
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 96
- 239000001282 iso-butane Substances 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 41
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 41
- 239000000047 product Substances 0.000 claims description 33
- 239000003595 mist Substances 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 23
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 15
- 150000001336 alkenes Chemical class 0.000 claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000000443 aerosol Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 239000012188 paraffin wax Substances 0.000 claims description 9
- 150000005673 monoalkenes Chemical class 0.000 claims description 6
- 150000005674 acyclic monoalkenes Chemical class 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 description 26
- 239000012071 phase Substances 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 13
- 239000000376 reactant Substances 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 11
- 239000007791 liquid phase Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000000889 atomisation Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229940057995 liquid paraffin Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 229910000619 316 stainless steel Inorganic materials 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 238000007726 management method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- JEAKTLDJVSMBKC-UHFFFAOYSA-N 2-methylpropane;2-methylprop-1-ene Chemical group CC(C)C.CC(C)=C JEAKTLDJVSMBKC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000016726 Coat Protein Complex I Human genes 0.000 description 1
- 108010092897 Coat Protein Complex I Proteins 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 206010042618 Surgical procedure repeated Diseases 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- JNDDXAUSKFKLLR-DFHCBJLBSA-N [(z)-4-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-3-benzoylsulfanylpent-3-enyl] benzoate;2-ethoxybenzamide;n-(4-ethoxyphenyl)-3-hydroxybutanamide;1,3,7-trimethylpurine-2,6-dione Chemical compound CCOC1=CC=CC=C1C(N)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.CCOC1=CC=C(NC(=O)CC(C)O)C=C1.C=1C=CC=CC=1C(=O)OCC\C(SC(=O)C=1C=CC=CC=1)=C(/C)N(C=O)CC1=CN=C(C)N=C1N JNDDXAUSKFKLLR-DFHCBJLBSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- -1 feedstocks Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000011555 saturated liquid Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J12/00—Chemical processes in general for reacting gaseous media with gaseous media; Apparatus specially adapted therefor
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15060771A | 1971-06-07 | 1971-06-07 | |
| US25071872A | 1972-05-05 | 1972-05-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2227770A1 true DE2227770A1 (de) | 1973-02-08 |
Family
ID=26847837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2227770A Pending DE2227770A1 (de) | 1971-06-07 | 1972-06-07 | Verfahren zur alkylierung von gasfoermigen azyklischen monoolefinen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3780130A (enExample) |
| BE (1) | BE784381A (enExample) |
| CA (1) | CA980803A (enExample) |
| DE (1) | DE2227770A1 (enExample) |
| FR (1) | FR2140459B1 (enExample) |
| GB (1) | GB1371873A (enExample) |
| IT (1) | IT965697B (enExample) |
| NL (1) | NL7207744A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5221777A (en) * | 1991-06-07 | 1993-06-22 | Mobil Oil Corporation | Isoparaffin:olefin alkylation process employing Lewis-acid promoted pillared layered silicate |
| US5196626A (en) * | 1991-11-04 | 1993-03-23 | Mobil Oil Corporation | Film type alkylation process |
| US7982086B2 (en) * | 2009-02-03 | 2011-07-19 | Catalytic Distillation Technologies | Deisobutenizer |
| CN106278785B (zh) * | 2015-06-29 | 2019-01-08 | 中国石油化工股份有限公司 | 一种异构烷烃与烯烃的固体酸烷基化反应方法 |
-
1972
- 1972-05-05 US US00250718A patent/US3780130A/en not_active Expired - Lifetime
- 1972-05-17 CA CA142,397A patent/CA980803A/en not_active Expired
- 1972-06-05 BE BE784381A patent/BE784381A/xx unknown
- 1972-06-06 FR FR7220211A patent/FR2140459B1/fr not_active Expired
- 1972-06-06 GB GB2625072A patent/GB1371873A/en not_active Expired
- 1972-06-06 IT IT25298/72A patent/IT965697B/it active
- 1972-06-07 DE DE2227770A patent/DE2227770A1/de active Pending
- 1972-06-07 NL NL7207744A patent/NL7207744A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2140459B1 (enExample) | 1977-12-23 |
| BE784381A (fr) | 1972-12-05 |
| IT965697B (it) | 1974-02-11 |
| FR2140459A1 (enExample) | 1973-01-19 |
| GB1371873A (en) | 1974-10-30 |
| US3780130A (en) | 1973-12-18 |
| CA980803A (en) | 1975-12-30 |
| NL7207744A (enExample) | 1972-12-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |