CA1048062A - Process for the production of methyl tert-butyl ether - Google Patents
Process for the production of methyl tert-butyl etherInfo
- Publication number
- CA1048062A CA1048062A CA228,655A CA228655A CA1048062A CA 1048062 A CA1048062 A CA 1048062A CA 228655 A CA228655 A CA 228655A CA 1048062 A CA1048062 A CA 1048062A
- Authority
- CA
- Canada
- Prior art keywords
- isobutylene
- methanol
- mixture
- parts
- reactor
- 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
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 135
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000004821 distillation Methods 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 6
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 5
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 5
- 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 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 19
- 150000001336 alkenes Chemical class 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 3
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 11
- 239000000047 product Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- BRSDPVLOTZLFFV-UHFFFAOYSA-N methanol;2-methylprop-1-ene Chemical compound OC.CC(C)=C BRSDPVLOTZLFFV-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2MP Natural products CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- -1 methyl -tert-butyl Chemical group 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23013/74A IT1012690B (it) | 1974-05-21 | 1974-05-21 | Procedimento per la produzione di eteri ter alchilici |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1048062A true CA1048062A (en) | 1979-02-06 |
Family
ID=11202877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA228,655A Expired CA1048062A (en) | 1974-05-21 | 1975-05-21 | Process for the production of methyl tert-butyl ether |
Country Status (33)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2629769C3 (de) * | 1976-07-02 | 1989-03-16 | Hüls AG, 4370 Marl | Verfahren zur Herstellung von reinem Methyl-tertiär-butyläther |
| JPS5342698U (enrdf_load_stackoverflow) * | 1976-09-17 | 1978-04-12 | ||
| DE2706465C3 (de) * | 1977-02-16 | 1980-10-02 | Deutsche Texaco Ag, 2000 Hamburg | Verfahren zur Gewinnung von Butadien bzw. n-Butenen aus diese enthaltenden Kohlenwasserstoffgemischen unter Abtrennung von Isobuten |
| JPS54130679U (enrdf_load_stackoverflow) * | 1978-03-03 | 1979-09-11 | ||
| DE2853769C3 (de) * | 1978-12-13 | 1989-03-16 | Hüls AG, 4370 Marl | Verfahren zur gleichzeitigen Herstellung von reinem Methyl-tert.-butylether und einem C↓4↓-Kohlenwasserstoffgemisch, das wesentlich weniger als 1% Isobuten enthält |
| DE2928509A1 (de) * | 1979-07-14 | 1981-01-29 | Basf Ag | Verfahren zur gemeinsamen herstellung von methyl-tert.-butylaether und gewinnung von isobuten |
| EP0075838A1 (en) * | 1981-09-24 | 1983-04-06 | Phillips Petroleum Company | Process for the preparation of methyl tert-butyl ether |
| JPS5921206U (ja) * | 1982-07-31 | 1984-02-09 | 武田 精 | スナツプフアスナ−用の嵌合部材 |
| DE3322753A1 (de) * | 1983-06-24 | 1985-01-10 | Deutsche Texaco Ag, 2000 Hamburg | Verfahren zur herstellung von methyl-tert.-butylaether |
| JPS6013010U (ja) * | 1983-07-05 | 1985-01-29 | カラ−フアスナ−工業株式会社 | ホツク装置 |
| JPH0641833Y2 (ja) * | 1989-05-11 | 1994-11-02 | 三菱製紙株式会社 | シェアーカット方式の下刃軸 |
| IT1247108B (it) | 1991-02-28 | 1994-12-12 | Snam Progetti | Procedimento integrato per la produzione di iso-butene ed eteri alchil-ter-butilici. |
| RU2102375C1 (ru) * | 1995-08-07 | 1998-01-20 | Товарищество с ограниченной ответственностью "Научно-исследовательский центр по нефтехимическим технологиям" | Способ получения алкил-трет.алкиловых эфиров и их смесей с углеводородами |
| RU2102374C1 (ru) * | 1996-07-18 | 1998-01-20 | Товарищество с ограниченной ответственностью "Научно-исследовательский центр по нефтехимическим технологиям" | Способ получения алкил-трет-алкиловых эфиров и/или их смесей с углеводородами |
| EP3919468A1 (en) * | 2020-06-03 | 2021-12-08 | SABIC Global Technologies B.V. | Systems and processes for producing methyl tertiary butyl ether |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1968601A (en) * | 1934-02-14 | 1934-07-31 | Shell Dev | Preparation of olefine derivatives |
| US2480940A (en) * | 1946-09-20 | 1949-09-06 | Atlantic Refining Co | Production of aliphatic ethers |
| DE1224294B (de) * | 1961-01-09 | 1966-09-08 | Bayer Ag | Verfahren zur Herstellung von tertiaeren Butylalkylaethern |
| AT230345B (de) * | 1961-01-09 | 1963-12-10 | Bayer Ag | Verfahren zur Herstellung von tert.-Butyl-alkyläthern |
| GB1173128A (en) * | 1968-09-20 | 1969-12-03 | Shell Int Research | Process for the preparation of Olefins |
-
1974
- 1974-05-21 IT IT23013/74A patent/IT1012690B/it active
-
1975
- 1975-05-06 ZA ZA00752914A patent/ZA752914B/xx unknown
- 1975-05-12 MW MW30/75A patent/MW3075A1/xx unknown
- 1975-05-13 TR TR18546A patent/TR18546A/xx unknown
- 1975-05-13 GB GB20209/75A patent/GB1506312A/en not_active Expired
- 1975-05-15 IE IE1094/75A patent/IE43301B1/en unknown
- 1975-05-15 PL PL1975180405A patent/PL103015B1/pl unknown
- 1975-05-16 DE DE2521963A patent/DE2521963C3/de not_active Expired
- 1975-05-16 YU YU1263/75A patent/YU37301B/xx unknown
- 1975-05-18 EG EG297/75A patent/EG12653A/xx active
- 1975-05-19 IN IN999/CAL/1975A patent/IN143295B/en unknown
- 1975-05-20 FR FR7515722A patent/FR2272065B1/fr not_active Expired
- 1975-05-20 HU HU75SA2797A patent/HU176319B/hu not_active IP Right Cessation
- 1975-05-20 LU LU72542A patent/LU72542A1/xx unknown
- 1975-05-20 ES ES438189A patent/ES438189A1/es not_active Expired
- 1975-05-20 DK DK222275AA patent/DK135796B/da unknown
- 1975-05-20 CS CS753520A patent/CS219316B2/cs unknown
- 1975-05-20 AT AT381375A patent/AT338223B/de not_active IP Right Cessation
- 1975-05-20 BG BG030034A patent/BG26514A3/xx unknown
- 1975-05-20 NO NO751787A patent/NO144524C/no unknown
- 1975-05-21 SE SE7505804A patent/SE425482B/xx not_active IP Right Cessation
- 1975-05-21 ZM ZM64/75A patent/ZM6475A1/xx unknown
- 1975-05-21 NL NLAANVRAGE7505998,A patent/NL183886C/xx not_active IP Right Cessation
- 1975-05-21 CH CH649575A patent/CH605509A5/xx not_active IP Right Cessation
- 1975-05-21 SU SU752136591A patent/SU858557A3/ru active
- 1975-05-21 DD DD186165A patent/DD118067A5/xx unknown
- 1975-05-21 BE BE156545A patent/BE829303A/xx not_active IP Right Cessation
- 1975-05-21 RO RO7582288A patent/RO72850A/ro unknown
- 1975-05-21 CA CA228,655A patent/CA1048062A/en not_active Expired
- 1975-05-21 AR AR258895A patent/AR226992A1/es active
- 1975-05-21 JP JP50059793A patent/JPS516914A/ja active Granted
- 1975-05-21 PH PH17183A patent/PH13250A/en unknown
- 1975-05-22 BR BR4088/75D patent/BR7503196A/pt unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3979461A (en) | Process for the preparation of methyl tert-butyl ether | |
| US4071567A (en) | Process for the production of methyl tert-butyl ether | |
| CA1048062A (en) | Process for the production of methyl tert-butyl ether | |
| SU1223839A3 (ru) | Способ получени метилтретбутилового эфира | |
| US4320232A (en) | Process for conjointly preparing methyl tert.-butyl ether and obtaining isobutene | |
| US4282389A (en) | Process for the simultaneous manufacture of pure MTBE and a substantially isobutene-free mixture of C4 -hydrocarbons | |
| US7002050B2 (en) | Process for preparing tert-butanol from isobutene-containing hydrocarbon mixtures | |
| CA1253886A (en) | Process for producing methyl tertiary butyl ether | |
| CA1133951A (en) | Isolation of isobutene from c4-hydrocarbon mixtures containing isobutene | |
| KR100513915B1 (ko) | 3급-부틸 알콜의 제조방법 | |
| US4413150A (en) | Two product process for methyl tertiary butyl ether production | |
| KR101075381B1 (ko) | 3급 부탄올의 제조방법 | |
| GB2096604A (en) | Decomposition of alkyl tert- alkyl ethers | |
| US4236034A (en) | Process for producing tert-butanol from mixed butylenes | |
| RU2030383C1 (ru) | Способ получения метил-трет-бутилового эфира | |
| EP0390596A3 (en) | Combined etherification and alkylation process | |
| US4270011A (en) | Process for the production of tertiary butyl alcohol | |
| US7115787B2 (en) | Method for producing tert-butanol by means of reactive rectification | |
| EP0071238A1 (en) | Process for the preparation of methyl tert-butyl ether | |
| US4569725A (en) | Separation of a C4 -hydrocarbon mixture essentially containing n-butenes and butanes | |
| KR790001105B1 (ko) | 3급 알킬에테로의 제조방법 | |
| GB2060616A (en) | Process for the production of tertiary butyl alcohol | |
| JPS5951224A (ja) | Ｃ↓４炭化水素留分からイソブチレンを分離する方法 | |
| KR830000879B1 (ko) | 제3부틸 알코올의 제조방법 | |
| US3205244A (en) | Improved catalytic synthesis of carboxylic acids from olefins, carbon monoxide and water |