CS273639B2 - Method of methyl-tertiary alkylethers synthesis - Google Patents
Method of methyl-tertiary alkylethers synthesis Download PDFInfo
- Publication number
- CS273639B2 CS273639B2 CS354287A CS354287A CS273639B2 CS 273639 B2 CS273639 B2 CS 273639B2 CS 354287 A CS354287 A CS 354287A CS 354287 A CS354287 A CS 354287A CS 273639 B2 CS273639 B2 CS 273639B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methanol
- oxygen
- column
- excess
- item
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 230000015572 biosynthetic process Effects 0.000 title claims description 8
- 238000003786 synthesis reaction Methods 0.000 title claims description 7
- 125000005011 alkyl ether group Chemical group 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 93
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229930195733 hydrocarbon Natural products 0.000 claims description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 12
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical class C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 239000002737 fuel gas Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 238000007872 degassing Methods 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- 238000009423 ventilation Methods 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- 229910000975 Carbon steel Inorganic materials 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000010962 carbon steel Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- -1 for example Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052598 goethite Inorganic materials 0.000 description 1
- AEIXRCIKZIZYPM-UHFFFAOYSA-M hydroxy(oxo)iron Chemical compound [O][Fe]O AEIXRCIKZIZYPM-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QGZKDVFQNNGYKY-NJFSPNSNSA-N nitrogen-16 Chemical compound [16NH3] QGZKDVFQNNGYKY-NJFSPNSNSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20573/86A IT1190017B (it) | 1986-05-27 | 1986-05-27 | Processo per la sintesi di eterimetilteralchilici con soppressione della corrosione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS354287A2 CS354287A2 (en) | 1990-08-14 |
| CS273639B2 true CS273639B2 (en) | 1991-03-12 |
Family
ID=11169005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS354287A CS273639B2 (en) | 1986-05-27 | 1987-05-15 | Method of methyl-tertiary alkylethers synthesis |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0311614A1 (it) |
| JP (1) | JPH01502748A (it) |
| BR (1) | BR8707693A (it) |
| CS (1) | CS273639B2 (it) |
| DD (1) | DD260924A5 (it) |
| ES (1) | ES2006491A6 (it) |
| GR (1) | GR870748B (it) |
| HU (1) | HUT47892A (it) |
| IT (1) | IT1190017B (it) |
| PL (1) | PL150602B1 (it) |
| WO (1) | WO1987007260A1 (it) |
| YU (1) | YU95287A (it) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5237109A (en) * | 1991-10-10 | 1993-08-17 | Phillips Petroleum Company | Etherification process |
| RU2544553C1 (ru) * | 2013-12-25 | 2015-03-20 | Открытое акционерное общество "Газпромнефть-Московский НПЗ" (ОАО "Газпромнефть-МНПЗ") | Способ получения высокооктановой добавки к автомобильному бензину |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1259337A (en) * | 1982-09-20 | 1989-09-12 | Joe Van Pool | Combined ether and alkylate production |
-
1986
- 1986-05-27 IT IT20573/86A patent/IT1190017B/it active
-
1987
- 1987-05-07 BR BR8707693A patent/BR8707693A/pt unknown
- 1987-05-07 HU HU873325A patent/HUT47892A/hu unknown
- 1987-05-07 EP EP87903869A patent/EP0311614A1/en not_active Ceased
- 1987-05-07 WO PCT/EP1987/000257 patent/WO1987007260A1/en not_active Application Discontinuation
- 1987-05-07 JP JP62503688A patent/JPH01502748A/ja active Pending
- 1987-05-13 GR GR870748A patent/GR870748B/el unknown
- 1987-05-15 CS CS354287A patent/CS273639B2/cs unknown
- 1987-05-22 ES ES8701707A patent/ES2006491A6/es not_active Expired
- 1987-05-25 DD DD87303104A patent/DD260924A5/de not_active IP Right Cessation
- 1987-05-25 PL PL1987265892A patent/PL150602B1/pl unknown
- 1987-05-26 YU YU00952/87A patent/YU95287A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1987007260A1 (en) | 1987-12-03 |
| YU95287A (en) | 1988-06-30 |
| PL265892A1 (en) | 1988-07-21 |
| DD260924A5 (de) | 1988-10-12 |
| GR870748B (en) | 1987-09-23 |
| JPH01502748A (ja) | 1989-09-21 |
| HUT47892A (en) | 1989-04-28 |
| BR8707693A (pt) | 1989-08-15 |
| IT1190017B (it) | 1988-02-10 |
| EP0311614A1 (en) | 1989-04-19 |
| IT8620573A0 (it) | 1986-05-27 |
| PL150602B1 (en) | 1990-06-30 |
| CS354287A2 (en) | 1990-08-14 |
| ES2006491A6 (es) | 1989-05-01 |
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