CA1224810A - Process for the preparation of methyl tert-butyl ether and ethyl tert-butyl ether - Google Patents
Process for the preparation of methyl tert-butyl ether and ethyl tert-butyl etherInfo
- Publication number
- CA1224810A CA1224810A CA000407704A CA407704A CA1224810A CA 1224810 A CA1224810 A CA 1224810A CA 000407704 A CA000407704 A CA 000407704A CA 407704 A CA407704 A CA 407704A CA 1224810 A CA1224810 A CA 1224810A
- Authority
- CA
- Canada
- Prior art keywords
- hour
- isobutylene
- line
- reaction
- fraction
- 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
- 238000000034 method Methods 0.000 title claims abstract description 24
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 title claims abstract description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 207
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 138
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 72
- 238000006243 chemical reaction Methods 0.000 claims abstract description 63
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 18
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 13
- 239000007791 liquid phase Substances 0.000 claims abstract description 10
- 239000012429 reaction media Substances 0.000 claims abstract description 5
- 239000003377 acid catalyst Substances 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 55
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 38
- 239000011541 reaction mixture Substances 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000000926 separation method Methods 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 238000010790 dilution Methods 0.000 abstract description 7
- 239000012895 dilution Substances 0.000 abstract description 7
- 239000007795 chemical reaction product Substances 0.000 abstract description 5
- 239000003208 petroleum Substances 0.000 abstract description 4
- 238000007233 catalytic pyrolysis Methods 0.000 abstract description 3
- 235000019441 ethanol Nutrition 0.000 description 84
- 229960004756 ethanol Drugs 0.000 description 61
- 150000001875 compounds Chemical class 0.000 description 42
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 239000000727 fraction Substances 0.000 description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 12
- 238000006266 etherification reaction Methods 0.000 description 10
- 230000036647 reaction Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- -1 ethyl tert-butyl Chemical group 0.000 description 7
- 230000015572 biosynthetic process Effects 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
- 235000013844 butane Nutrition 0.000 description 5
- 230000002349 favourable effect Effects 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 208000016253 exhaustion Diseases 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 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 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229940044600 maleic anhydride Drugs 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23195-A/81 | 1981-07-28 | ||
| IT23195/81A IT1167481B (it) | 1981-07-28 | 1981-07-28 | Procedimento per la preparazione di metil ter-butil etere e di etil ter-butil etere |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1224810A true CA1224810A (en) | 1987-07-28 |
Family
ID=11204765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000407704A Expired CA1224810A (en) | 1981-07-28 | 1982-07-21 | Process for the preparation of methyl tert-butyl ether and ethyl tert-butyl ether |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0071032B1 (OSRAM) |
| AR (1) | AR228191A1 (OSRAM) |
| AT (1) | ATE13049T1 (OSRAM) |
| BR (1) | BR8204380A (OSRAM) |
| CA (1) | CA1224810A (OSRAM) |
| DE (1) | DE3263381D1 (OSRAM) |
| ES (1) | ES514394A0 (OSRAM) |
| IN (1) | IN156276B (OSRAM) |
| IT (1) | IT1167481B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4490563A (en) * | 1981-08-28 | 1984-12-25 | Phillips Petroleum Company | Ether recovery |
| FR2683523B1 (fr) * | 1991-11-12 | 1994-02-11 | Institut Francais Petrole | Procede de separation d'ethyl tertiobutyl ether et d'ethanol. |
| DE102005062722A1 (de) | 2005-12-28 | 2007-07-12 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Ethyl-tert.-Butylether aus technischen Mischungen von C4-Kohlenwasserstoffen |
| DE102006003492A1 (de) | 2006-01-25 | 2007-07-26 | Oxeno Olefinchemie Gmbh | Verfahren zur Entwässerung von Ethanol |
| DE102006057856A1 (de) * | 2006-12-08 | 2008-06-19 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von Alkyl-tert-butylether und hochreinem Raffinat II |
| US7825282B2 (en) * | 2007-09-18 | 2010-11-02 | Catalytic Distillation Technologies | Process for the conversion of tertiary butyl alcohol to ethyl tertiary butyl ether |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4071567A (en) * | 1974-05-21 | 1978-01-31 | Snamprogetti S.P.A. | Process for the production of methyl tert-butyl ether |
| FR2449074A1 (fr) * | 1979-02-14 | 1980-09-12 | Inst Francais Du Petrole | Procede de production et d'isolement de methyl tertiobutyl ether |
| FR2456084A1 (fr) * | 1979-05-09 | 1980-12-05 | Inst Francais Du Petrole | Procede de preparation et d'isolement du methyl tertiobutyl ether |
-
1981
- 1981-07-28 IT IT23195/81A patent/IT1167481B/it active
-
1982
- 1982-06-29 AT AT82105793T patent/ATE13049T1/de not_active IP Right Cessation
- 1982-06-29 EP EP82105793A patent/EP0071032B1/en not_active Expired
- 1982-06-29 DE DE8282105793T patent/DE3263381D1/de not_active Expired
- 1982-07-21 CA CA000407704A patent/CA1224810A/en not_active Expired
- 1982-07-26 AR AR290084A patent/AR228191A1/es active
- 1982-07-26 IN IN861/CAL/82A patent/IN156276B/en unknown
- 1982-07-27 ES ES514394A patent/ES514394A0/es active Granted
- 1982-07-27 BR BR8204380A patent/BR8204380A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE13049T1 (de) | 1985-05-15 |
| IT8123195A0 (it) | 1981-07-28 |
| AR228191A1 (es) | 1983-01-31 |
| ES8305672A1 (es) | 1983-05-01 |
| ES514394A0 (es) | 1983-05-01 |
| IT1167481B (it) | 1987-05-13 |
| EP0071032A1 (en) | 1983-02-09 |
| EP0071032B1 (en) | 1985-05-02 |
| IN156276B (OSRAM) | 1985-06-08 |
| BR8204380A (pt) | 1983-01-18 |
| DE3263381D1 (en) | 1985-06-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5243091A (en) | Method for the manufacture and recovery of methyl tertiary butyl ether | |
| CA1151217A (en) | Process for conjointly preparing methyl tert-butyl ether and obtaining isobutene | |
| US4287379A (en) | Process for obtaining isobutene from C4 -hydrocarbon mixtures containing isobutene | |
| CA1133951A (en) | Isolation of isobutene from c4-hydrocarbon mixtures containing isobutene | |
| US5354912A (en) | Method for the removal of dimethyl ether from methyl tertiary butyl ether | |
| US5041690A (en) | Conversion of alcohols to ether-rich gasoline | |
| US5130101A (en) | Reactor system for conversion of alcohols to ether-rich gasoline | |
| US5811597A (en) | Method for the manufacture of methyl tertiary butyl ether from tertiary butyl alcohol and methanol | |
| AU4963390A (en) | Conversion of olefins to ethers | |
| CA2099751C (en) | Etherification process | |
| US4299997A (en) | Process for producing ethylene glycol mono-tert-butyl ether | |
| CA1224810A (en) | Process for the preparation of methyl tert-butyl ether and ethyl tert-butyl ether | |
| US5237109A (en) | Etherification process | |
| US5324866A (en) | Integrated process for producing diisopropyl ether from isopropyl alcohol | |
| US4322565A (en) | Process for purifying ethers | |
| EP0075838A1 (en) | Process for the preparation of methyl tert-butyl ether | |
| US4270011A (en) | Process for the production of tertiary butyl alcohol | |
| US5563301A (en) | Sequential reaction of TBA and isobutylene with methanol | |
| US20090253942A1 (en) | Process for the production of alkyl ethers by the etherification of isobutene | |
| GB2043065A (en) | Process for manufacturing and recovering methyl t-butyl ether | |
| US5144085A (en) | Feedstock dewatering and etherification of crude ethanol | |
| US5663454A (en) | Method for the manufacture and purification of methyl tertiary butyl ether and dimethyl ether | |
| JP2612194B2 (ja) | 線状オレフインの直接水加法 | |
| AU642297B2 (en) | Improved catalytic olefin hydration for ether production | |
| CA2080115C (en) | Etherification process |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |