DK172596B1 - Fremgangsmåde til fremstilling af et alkyleret carbonhydridprodukt ved trinvis væskefasealkylering af et carbonhydridsubstr - Google Patents
Fremgangsmåde til fremstilling af et alkyleret carbonhydridprodukt ved trinvis væskefasealkylering af et carbonhydridsubstr Download PDFInfo
- Publication number
- DK172596B1 DK172596B1 DK199600164A DK16496A DK172596B1 DK 172596 B1 DK172596 B1 DK 172596B1 DK 199600164 A DK199600164 A DK 199600164A DK 16496 A DK16496 A DK 16496A DK 172596 B1 DK172596 B1 DK 172596B1
- Authority
- DK
- Denmark
- Prior art keywords
- alkylation
- reactor
- stream
- product
- alkylating agent
- Prior art date
Links
- 238000005804 alkylation reaction Methods 0.000 title claims description 84
- 230000029936 alkylation Effects 0.000 title claims description 76
- 229930195733 hydrocarbon Natural products 0.000 title claims description 42
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 42
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 40
- 239000000758 substrate Substances 0.000 title claims description 35
- 239000007791 liquid phase Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 claims description 55
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 229940100198 alkylating agent Drugs 0.000 claims description 29
- 239000002168 alkylating agent Substances 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 23
- 150000003460 sulfonic acids Chemical class 0.000 claims description 12
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 238000007599 discharging Methods 0.000 claims 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 6
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000001282 iso-butane Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000005194 fractionation 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
- 239000002245 particle Substances 0.000 description 2
- 230000003134 recirculating effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- -1 perfluorinated alkyl sulfonic acids Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/025—Sulfonic acids
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK199600164A DK172596B1 (da) | 1996-02-15 | 1996-02-15 | Fremgangsmåde til fremstilling af et alkyleret carbonhydridprodukt ved trinvis væskefasealkylering af et carbonhydridsubstr |
| ES97100992T ES2132978T3 (es) | 1996-02-15 | 1997-01-23 | Procedimiento de alquilacion de varias etapas. |
| EP97100992A EP0790224B1 (en) | 1996-02-15 | 1997-01-23 | Staged alkylation process |
| DE69700195T DE69700195T2 (de) | 1996-02-15 | 1997-01-23 | Mehrstufenalkylierungsverfahren |
| RU97102195/04A RU2178778C2 (ru) | 1996-02-15 | 1997-02-14 | Способ получения углеводородной фракции, предназначенной для использования в двигателях внутреннего сгорания |
| JP9030834A JPH101447A (ja) | 1996-02-15 | 1997-02-14 | 段階的なアルキル化方法 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK16496 | 1996-02-15 | ||
| DK199600164A DK172596B1 (da) | 1996-02-15 | 1996-02-15 | Fremgangsmåde til fremstilling af et alkyleret carbonhydridprodukt ved trinvis væskefasealkylering af et carbonhydridsubstr |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK16496A DK16496A (da) | 1997-08-16 |
| DK172596B1 true DK172596B1 (da) | 1999-02-15 |
Family
ID=8090493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK199600164A DK172596B1 (da) | 1996-02-15 | 1996-02-15 | Fremgangsmåde til fremstilling af et alkyleret carbonhydridprodukt ved trinvis væskefasealkylering af et carbonhydridsubstr |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0790224B1 (enExample) |
| JP (1) | JPH101447A (enExample) |
| DE (1) | DE69700195T2 (enExample) |
| DK (1) | DK172596B1 (enExample) |
| ES (1) | ES2132978T3 (enExample) |
| RU (1) | RU2178778C2 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5817908A (en) * | 1996-05-20 | 1998-10-06 | Amoco Corporation | Staged alkylation process |
| AU1399299A (en) * | 1997-11-14 | 1999-06-07 | Abb Lummus Global Inc. | Hydrocarbon alkylation |
| US6395673B1 (en) | 2000-06-29 | 2002-05-28 | E. I. Du Pont De Nemours And Company | Catalyst of mixed fluorosulfonic acids |
| CN111589406B (zh) | 2019-02-21 | 2022-04-12 | 中国石油化工股份有限公司 | 烷基化反应装置、反应系统和液体酸催化的烷基化反应方法 |
| CN115838315B (zh) * | 2022-12-23 | 2023-11-17 | 常州瑞华化工工程技术股份有限公司 | 一种低芳烯比生产叔丁基乙苯的工艺及叔丁基乙苯 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR865161A (fr) * | 1939-04-26 | 1941-05-15 | Anglo Iranian Oil Co Ltd | Procédé et appareil pour la production de combustibles pour moteurs |
| US4783567A (en) * | 1987-11-23 | 1988-11-08 | Uop Inc. | HF alkylation process |
| DK168520B1 (da) * | 1989-12-18 | 1994-04-11 | Topsoe Haldor As | Fremgangsmåde til væskefase-alkylering af et carbonhydrid med et olefinalkyleringsmiddel |
| US5245100A (en) | 1989-12-18 | 1993-09-14 | Haldor Topsoe, S.A. | Alkylation process |
| AU6700794A (en) * | 1993-04-22 | 1994-11-08 | Mobil Oil Corporation | Isoparaffin/olefin alkylation |
| DK171932B1 (da) * | 1994-12-02 | 1997-08-18 | Topsoe Haldor As | Fremgangsmåde til alkylering af alifatiske carbonhydrider |
-
1996
- 1996-02-15 DK DK199600164A patent/DK172596B1/da not_active IP Right Cessation
-
1997
- 1997-01-23 ES ES97100992T patent/ES2132978T3/es not_active Expired - Lifetime
- 1997-01-23 EP EP97100992A patent/EP0790224B1/en not_active Expired - Lifetime
- 1997-01-23 DE DE69700195T patent/DE69700195T2/de not_active Expired - Fee Related
- 1997-02-14 JP JP9030834A patent/JPH101447A/ja active Pending
- 1997-02-14 RU RU97102195/04A patent/RU2178778C2/ru not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0790224A1 (en) | 1997-08-20 |
| JPH101447A (ja) | 1998-01-06 |
| DE69700195D1 (de) | 1999-06-02 |
| RU2178778C2 (ru) | 2002-01-27 |
| ES2132978T3 (es) | 1999-08-16 |
| DK16496A (da) | 1997-08-16 |
| EP0790224B1 (en) | 1999-04-28 |
| DE69700195T2 (de) | 1999-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |