JPH0519595B2 - - Google Patents
Info
- Publication number
- JPH0519595B2 JPH0519595B2 JP60133912A JP13391285A JPH0519595B2 JP H0519595 B2 JPH0519595 B2 JP H0519595B2 JP 60133912 A JP60133912 A JP 60133912A JP 13391285 A JP13391285 A JP 13391285A JP H0519595 B2 JPH0519595 B2 JP H0519595B2
- Authority
- JP
- Japan
- Prior art keywords
- methanol
- water
- fraction
- gasoline
- etherification
- 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 - Lifetime
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 165
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 238000006266 etherification reaction Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 229930195733 hydrocarbon Natural products 0.000 claims description 17
- 150000001336 alkenes Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 5
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 claims description 4
- 239000006286 aqueous extract Substances 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 16
- 238000004821 distillation Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 10
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- -1 methanol Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- IRUDSQHLKGNCGF-UHFFFAOYSA-N 2-methylhex-1-ene Chemical class CCCCC(C)=C IRUDSQHLKGNCGF-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 3
- JIUFYGIESXPUPL-UHFFFAOYSA-N 5-methylhex-1-ene Chemical class CC(C)CCC=C JIUFYGIESXPUPL-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004523 catalytic cracking Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000003808 methanol extraction Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical group CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- OWWIWYDDISJUMY-UHFFFAOYSA-N 2,3-dimethylbut-1-ene Chemical compound CC(C)C(C)=C OWWIWYDDISJUMY-UHFFFAOYSA-N 0.000 description 1
- FBCWFOLOHWOWFX-UHFFFAOYSA-N 2-methoxy-2-methylpropane;hydrate Chemical compound O.COC(C)(C)C FBCWFOLOHWOWFX-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- RYKZRKKEYSRDNF-UHFFFAOYSA-N 3-methylidenepentane Chemical compound CCC(=C)CC RYKZRKKEYSRDNF-UHFFFAOYSA-N 0.000 description 1
- BEQGRRJLJLVQAQ-UHFFFAOYSA-N 3-methylpent-2-ene Chemical compound CCC(C)=CC BEQGRRJLJLVQAQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10L1/023—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark ignition
-
- 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)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8409623A FR2565991B1 (fr) | 1984-06-18 | 1984-06-18 | Procede de valorisation d'essences olefiniques par etherification |
| FR8409623 | 1984-06-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6114288A JPS6114288A (ja) | 1986-01-22 |
| JPH0519595B2 true JPH0519595B2 ( ) | 1993-03-17 |
Family
ID=9305214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60133912A Granted JPS6114288A (ja) | 1984-06-18 | 1985-06-18 | オレフィン系ガソリンのエーテル化による高価値化方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4664675A ( ) |
| EP (1) | EP0166648B1 ( ) |
| JP (1) | JPS6114288A ( ) |
| DE (1) | DE3564588D1 ( ) |
| ES (1) | ES8604636A1 ( ) |
| FR (1) | FR2565991B1 ( ) |
| GR (1) | GR851289B ( ) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU86280A1 (fr) * | 1986-01-29 | 1987-09-03 | Labofina Sa | Procede de production d'essence |
| JP2629011B2 (ja) * | 1987-12-01 | 1997-07-09 | エヌティエヌ株式会社 | 免震すべり装置 |
| US4940833A (en) * | 1988-11-29 | 1990-07-10 | Phillips Petroleum Company | Olefin monomer separation process |
| US5102428A (en) * | 1989-10-20 | 1992-04-07 | Mobil Oil Corporation | Integrated process for the production of diisopropyl ether and gasoline |
| US5078751A (en) * | 1990-04-04 | 1992-01-07 | Mobil Oil Corporation | Process for upgrading olefinic gasoline by etherification wherein asymmetrical dialkyl ethers are produced |
| US5329051A (en) * | 1992-12-30 | 1994-07-12 | Phillips Petroleum Company | Ether recovery |
| US5413717A (en) * | 1993-08-30 | 1995-05-09 | Texaco Inc. | Method of recovering MTBE from wastewater |
| US5430197A (en) * | 1994-02-22 | 1995-07-04 | Chemica Research & Licensing Company | Recovery of alcohol from hydrocarbon streams |
| FR2730501B1 (fr) * | 1995-02-15 | 1997-04-18 | Inst Francais Du Petrole | Carburant obtenu par un procede comportant l'etherification optimisee en presence d'alcool d'une coupe d'hydrocarbures contenant des olefines ayant de 5 a 8 atomes de carbone |
| FR2730502B1 (fr) * | 1995-02-15 | 1997-04-18 | Inst Francais Du Petrole | Carburant obtenu par un procede comportant l'etherification optimisee d'une coupe d'hydrocarbures contenant des olefines ayant de 5 a 8 atomes de carbone |
| FR2730487B1 (fr) * | 1995-02-15 | 1997-09-19 | Inst Francais Du Petrole | Procede integre comportant l'etherification optimisee d'une coupe d'hydrocarbures contenant des olefines ayant 6 atomes de carbone par molecule |
| JP4938470B2 (ja) * | 2006-02-20 | 2012-05-23 | 未来工業株式会社 | 通水管の接続端部、通水管接続用の係合体、通水管接続用のコア部材、通水管体、通水管の接続構造、通水管装置、通水管の保護キャップ、および通水管の接続端部形成工具 |
| CN102492466A (zh) * | 2011-12-09 | 2012-06-13 | 宁夏宝塔石化集团应用技术研究院（有限公司） | 一种催化汽油醚化生产工艺及装置 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5132510A (ja) * | 1974-08-30 | 1976-03-19 | Texaco Development Corp | Futaishoeeterunoseizohoho |
| JPS5168512A ( ) * | 1974-12-02 | 1976-06-14 | Texaco Development Corp |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE590370A ( ) * | 1959-04-29 | 1900-01-01 | ||
| US3902870A (en) * | 1974-05-30 | 1975-09-02 | Mobil Oil Corp | Process for the production of gasoline |
| PH12545A (en) * | 1975-06-06 | 1979-06-07 | Texaco Development Corp | Method for preparation of ethers |
| US4193770A (en) * | 1977-12-22 | 1980-03-18 | Gulf Canada Limited | Preparation of gasoline containing tertiaryamyl methyl ether |
| US4218569A (en) * | 1978-03-14 | 1980-08-19 | Gulf Canada Limited | Method for processing etherified light hydrocarbon mixtures to remove methanol |
| US4204077A (en) * | 1978-10-02 | 1980-05-20 | Gulf Canada Limited | Etherification processing of light hydrocarbons |
| EP0026041B1 (en) * | 1979-08-30 | 1983-01-26 | Mobil Oil Corporation | A method for producing olefins and/or ethers of high octane number |
| DE3150755A1 (de) * | 1981-12-22 | 1983-06-30 | Deutsche Texaco Ag, 2000 Hamburg | "verfahren zur abtrennung von methanol aus den bei der veraetherung von c(pfeil abwaerts)4(pfeil abwaerts) bis c(pfeil abwaerts)7(pfeil abwaerts)-isoolefinen mit methanol anfallenden reaktionsprodukten" |
-
1984
- 1984-06-18 FR FR8409623A patent/FR2565991B1/fr not_active Expired
-
1985
- 1985-05-27 GR GR851289A patent/GR851289B/el unknown
- 1985-06-10 EP EP85401132A patent/EP0166648B1/fr not_active Expired
- 1985-06-10 DE DE8585401132T patent/DE3564588D1/de not_active Expired
- 1985-06-17 ES ES544288A patent/ES8604636A1/es not_active Expired
- 1985-06-18 US US06/745,985 patent/US4664675A/en not_active Expired - Lifetime
- 1985-06-18 JP JP60133912A patent/JPS6114288A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5132510A (ja) * | 1974-08-30 | 1976-03-19 | Texaco Development Corp | Futaishoeeterunoseizohoho |
| JPS5168512A ( ) * | 1974-12-02 | 1976-06-14 | Texaco Development Corp |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2565991A1 (fr) | 1985-12-20 |
| EP0166648B1 (fr) | 1988-08-24 |
| US4664675A (en) | 1987-05-12 |
| ES544288A0 (es) | 1986-02-01 |
| ES8604636A1 (es) | 1986-02-01 |
| EP0166648A1 (fr) | 1986-01-02 |
| DE3564588D1 (en) | 1988-09-29 |
| JPS6114288A (ja) | 1986-01-22 |
| FR2565991B1 (fr) | 1986-10-03 |
| GR851289B ( ) | 1985-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |