NO821136L - PROCEDURE FOR DIVOLUTION OF ALKYL-TERT.ALKYLETERS. - Google Patents
PROCEDURE FOR DIVOLUTION OF ALKYL-TERT.ALKYLETERS.Info
- Publication number
- NO821136L NO821136L NO821136A NO821136A NO821136L NO 821136 L NO821136 L NO 821136L NO 821136 A NO821136 A NO 821136A NO 821136 A NO821136 A NO 821136A NO 821136 L NO821136 L NO 821136L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- ether
- plates
- splitting
- tert
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 150000001336 alkenes Chemical class 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical class C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/08—Alkenes with four carbon atoms
- C07C11/09—Isobutene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/04—Methanol
-
- 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
- C07C2531/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- C07C2531/08—Ion-exchange resins
- C07C2531/10—Ion-exchange resins sulfonated
-
- 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
- Y02P20/10—Process efficiency
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
Description
Foreliggende oppfinnelse vedrører en fremgangsmåte for spaltning alkyl-tertalkyletére" for å fremstille det tilsvarende olefin og alkohol, og det særegne ved fremgangsmåten i henhold til oppfinnelsen er at alkyl-tert.alkyleteren tilføres en destillasjonskolonne inneholdende en katalysator egnet for eterspaltningen og at det fremstilte olefin trekkes ut kontinuerlig fra toppen av kolonnen, idet bunnproduktet utgjøres av ren alkohol eller i det minste en blanding av alkohol og eter. The present invention relates to a method for splitting alkyl-tert-alkyl ethers to produce the corresponding olefin and alcohol, and the peculiarity of the method according to the invention is that the alkyl-tert-alkyl ether is supplied to a distillation column containing a catalyst suitable for the ether splitting and that the produced olefin is extracted continuously from the top of the column, the bottom product being pure alcohol or at least a mixture of alcohol and ether.
Disse og andre trekk ved fremgangsmåten i henhold til oppfinnelsen fremgår av patentkravene. These and other features of the method according to the invention appear in the patent claims.
Oppfinnelsen vedrører spesielt en fremgangsmåte for spaltning av metyl-tert.butyleter (MTBE). The invention relates in particular to a method for splitting methyl tert.butyl ether (MTBE).
Metyl-tertalkyletere spaltes for å frembringe de tilsvarende de-finer i en høy grad av renhet, men spaltningen og separeringen frembyr vanligvis problemer på grunn av den letthet som de fremstilte olefiner har til å dimeriseres. Methyl tertalkyl ethers are cleaved to produce the corresponding olefins in a high degree of purity, but the cleaving and separation usually present problems because of the ease with which the olefins produced dimerize.
Både når man arbeider i væskefase og i dampfase vil olefinene gjerne gi dimeriseringsprodukter. Both when working in the liquid phase and in the vapor phase, the olefins will tend to give dimerization products.
Det er nå funnet mulig å unngå ulempene med den kjente teknikk ved på passende måte å utnytte den relative flyktighetsforskjell mellom det fremstile olefin og den tilsvarende eter og alkohol. It has now been found possible to avoid the disadvantages of the known technique by appropriately exploiting the relative volatility difference between the olefin produced and the corresponding ether and alcohol.
Fremgangsmåten i henhold til oppfinnelsen gjennomføres i en plate-destilasjonskolonne hvor i det minste en av platene er forsynt med et katalysatorlag basert på sulfonerte styren-divinylbenzen-harpikser. The method according to the invention is carried out in a plate distillation column where at least one of the plates is provided with a catalyst layer based on sulfonated styrene-divinylbenzene resins.
Katalysatorlaget gjennomstrømmes av en væske som strømmer ned fra de øvre plater og av dampen som stiger fra de underliggende plater, idet varmen for spaltning av alkyl-tertalkyleteren tilføres ved,kondensering av idet minste en del av den damp som skriver seg fra destillasjonsplatene under den eller de plater som er forsynt med spaltningskatalysatoren. The catalyst layer is flowed through by a liquid that flows down from the upper plates and by the steam that rises from the underlying plates, the heat for splitting the alkyl-tertalkyl ether being supplied by condensation of at least part of the steam that escapes from the distillation plates below it or the plates provided with the cracking catalyst.
Eteren tilføres i det minste en' plate over den høyeste plate forsynt med spaltningskatalysator. The ether is supplied to at least one plate above the highest plate provided with a cleavage catalyst.
Som nevnt er topp-produktet olefinet, mens bunnproduktet kan være enten den rene alkohol eller en blanding av alkohol og uspaltet eter, i samsvar med de betingelser hvorunder destilla-sjonsprosessen gjennomføres og i samsvar med etertilførselen. As mentioned, the top product is the olefin, while the bottom product can be either the pure alcohol or a mixture of alcohol and uncleaved ether, in accordance with the conditions under which the distillation process is carried out and in accordance with the ether supply.
Når den nevnte blanding av alkohol og eter oppnås kan denne for-delaktig destilleres for å separere alkoholen fra eteren, idet den sistnevnte resirkuleres til spaltnings-^og separerings-opera-sjonen i platekolonnen. When the aforementioned mixture of alcohol and ether is obtained, this can advantageously be distilled to separate the alcohol from the ether, the latter being recycled to the cleavage and separation operation in the plate column.
Oppfinnelsen vil bedre forstås fra det etterfølgende utførelses-eksempel. The invention will be better understood from the following embodiment example.
EKSEMPELEXAMPLE
En destillasjonskolonne ble bygget opp under anvendelse av flen-sede rørseksjoner med diameter 10 cm og lengde 100 cm, inneholdende seks klokke-destillasjonsplater (to klokker pr. plate). A distillation column was constructed using flanged pipe sections of diameter 10 cm and length 100 cm, containing six bell distillation plates (two bells per plate).
Kolonnen ble bygget opp ved å veksl eim lengder av røret fylt med katalysator med rørseksjoner innenholdende seks plater til å gi totalt to rørseksjoner inneholdende plater over tilførslen og seks rørseksjoner under tilførselen, hvorav tre seksjoner inneholdende plater ble alternert med tre seksjoner inneholdende katalysator. Katalysatoren var "Amberlyst 15" fremstilt av Rohm & Haas. The column was built up by alternating lengths of pipe filled with catalyst with pipe sections containing six plates to give a total of two pipe sections containing plates above the feed and six pipe sections below the feed, of which three sections containing plates were alternated with three sections containing catalyst. The catalyst was "Amberlyst 15" manufactured by Rohm & Haas.
Kolonnen ble tilført 1 kg/h MTBE hvortil det ble tilsatt er resirkulert blanding av metanol og MTBE inneholdende 50 g metanol og 200 g MTBE. The column was fed 1 kg/h of MTBE to which was added a recycled mixture of methanol and MTBE containing 50 g of methanol and 200 g of MTBE.
Det ble opprettholdt et tilbakeløpsforhold på 2:1, ProsessenA reflux ratio of 2:1 was maintained, the Process
ble gjennomført ved en trykk på 5 atmosfærer absolutt og en temperatur på mellom 45 og 110°C. Topp-produktet bestod av 560 g C. inneholdende 20 g metanol og spor av diisobuten. was carried out at a pressure of 5 atmospheres absolute and a temperature of between 45 and 110°C. The top product consisted of 560 g of C. containing 20 g of methanol and traces of diisobutene.
Bunnproduktet bestod av 590 g metanol sammen med 200. g MTBE. The bottom product consisted of 590 g of methanol together with 200 g of MTBE.
Bunnstrommen ble tilført en ytterligere fylt kolonne med atmos-færetrykk og som ble drevet under et tilbakeløpsforhold på 3:1. Bunnproduktet bestod av 540 g ren metanol og topp-produktet, som ble resirkulert til den første kolonne, bestod av 200 g MTBE og 50 g metanol. The bottoms were fed to a further column packed at atmospheric pressure and operated at a reflux ratio of 3:1. The bottom product consisted of 540 g of pure methanol and the top product, which was recycled to the first column, consisted of 200 g of MTBE and 50 g of methanol.
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21031/81A IT1137526B (en) | 1981-04-10 | 1981-04-10 | Olefin and alcohol prodn. from alkyl tert.-alkyl ether |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO821136L true NO821136L (en) | 1982-10-11 |
Family
ID=11175661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO821136A NO821136L (en) | 1981-04-10 | 1982-04-05 | PROCEDURE FOR DIVOLUTION OF ALKYL-TERT.ALKYLETERS. |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS57179126A (en) |
| KR (1) | KR850001733B1 (en) |
| AR (1) | AR231527A1 (en) |
| AU (1) | AU8173882A (en) |
| BE (1) | BE892808A (en) |
| BR (1) | BR8201673A (en) |
| CH (1) | CH648275A5 (en) |
| CS (1) | CS233728B2 (en) |
| DD (1) | DD202525A5 (en) |
| DE (1) | DE3210435A1 (en) |
| DK (1) | DK153082A (en) |
| ES (1) | ES511630A0 (en) |
| FR (1) | FR2503699A1 (en) |
| GB (1) | GB2096604B (en) |
| GR (1) | GR76143B (en) |
| LU (1) | LU84078A1 (en) |
| MW (1) | MW1682A1 (en) |
| NL (1) | NL8201473A (en) |
| NO (1) | NO821136L (en) |
| NZ (1) | NZ200039A (en) |
| PH (1) | PH16956A (en) |
| PL (1) | PL235880A1 (en) |
| PT (1) | PT74728B (en) |
| RO (1) | RO83670B (en) |
| SE (1) | SE8202232L (en) |
| TR (1) | TR21520A (en) |
| YU (1) | YU78982A (en) |
| ZA (1) | ZA821810B (en) |
| ZM (1) | ZM2582A1 (en) |
| ZW (1) | ZW6182A1 (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4570026A (en) * | 1983-08-12 | 1986-02-11 | Petro-Tex Chemical Corporation | Production of isobutene from methyl tertiary butyl ether |
| US4587373A (en) * | 1984-12-12 | 1986-05-06 | Mobil Oil Corporation | Dimethylether recovery and/or recycle in an MTC conversion plant |
| DE3509292A1 (en) * | 1985-03-15 | 1985-12-05 | Ulrich 3300 Braunschweig Haupt | METHOD FOR PRODUCING PURE TERTIAL OLEFINS |
| DE3868763D1 (en) * | 1987-08-04 | 1992-04-09 | Erdoelchemie Gmbh | METHOD FOR CLEAVING ALKYL-TERT.-ALKYL ETHERS. |
| US5133942A (en) * | 1989-06-07 | 1992-07-28 | Chemical Research & Licensing Company | Distillation column reactor with catalyst replacement apparatus |
| US5198196A (en) * | 1989-06-07 | 1993-03-30 | Chemical Research & Licensing Company | Method for removing and replacing catalyst in a distillation column reactor |
| US5057468A (en) * | 1990-05-21 | 1991-10-15 | Chemical Research & Licensing Company | Catalytic distillation structure |
| US5262012A (en) * | 1990-09-19 | 1993-11-16 | Chemical Research & Licensing Company | Catalytic distillation system |
| US5510089A (en) * | 1991-07-22 | 1996-04-23 | Chemical Research & Licensing Company | Method for operating a distillation column reactor |
| US6416659B1 (en) | 2000-08-17 | 2002-07-09 | Catalytic Distillation Technologies | Process for the production of an ultra low sulfur |
| DE102006040431A1 (en) * | 2006-08-29 | 2008-03-20 | Oxeno Olefinchemie Gmbh | Process for cleaving MTBE |
| DE102006040430B4 (en) | 2006-08-29 | 2022-06-15 | Evonik Operations Gmbh | MTBE cleavage process |
| DE102006040434A1 (en) * | 2006-08-29 | 2008-03-06 | Oxeno Olefinchemie Gmbh | Process for cleaving MTBE |
| US10792642B2 (en) | 2014-12-03 | 2020-10-06 | China Petroleum & Chemical Corporation | Catalyst and preparation method thereof, and method for preparing isobutylene by applying the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008860B2 (en) * | 1978-07-27 | 1991-12-04 | CHEMICAL RESEARCH & LICENSING COMPANY | Catalyst system |
-
1982
- 1982-03-17 NZ NZ200039A patent/NZ200039A/en unknown
- 1982-03-17 ZA ZA821810A patent/ZA821810B/en unknown
- 1982-03-19 AU AU81738/82A patent/AU8173882A/en not_active Abandoned
- 1982-03-22 DE DE19823210435 patent/DE3210435A1/en not_active Ceased
- 1982-03-23 BR BR8201673A patent/BR8201673A/en unknown
- 1982-03-23 PH PH27041A patent/PH16956A/en unknown
- 1982-03-23 GR GR67713A patent/GR76143B/el unknown
- 1982-03-24 KR KR8201264A patent/KR850001733B1/en not_active Expired
- 1982-03-24 ZW ZW61/82A patent/ZW6182A1/en unknown
- 1982-03-29 GB GB8209146A patent/GB2096604B/en not_active Expired
- 1982-03-31 MW MW16/82A patent/MW1682A1/en unknown
- 1982-04-01 RO RO107122A patent/RO83670B/en unknown
- 1982-04-01 FR FR8205612A patent/FR2503699A1/en active Granted
- 1982-04-02 DK DK153082A patent/DK153082A/en not_active IP Right Cessation
- 1982-04-05 NO NO821136A patent/NO821136L/en unknown
- 1982-04-06 ES ES511630A patent/ES511630A0/en active Granted
- 1982-04-06 AR AR289023A patent/AR231527A1/en active
- 1982-04-07 NL NL8201473A patent/NL8201473A/en not_active Application Discontinuation
- 1982-04-07 SE SE8202232A patent/SE8202232L/en not_active Application Discontinuation
- 1982-04-07 LU LU84078A patent/LU84078A1/en unknown
- 1982-04-07 DD DD82238826A patent/DD202525A5/en unknown
- 1982-04-07 CH CH2169/82A patent/CH648275A5/en not_active IP Right Cessation
- 1982-04-08 CS CS822525A patent/CS233728B2/en unknown
- 1982-04-08 PT PT74728A patent/PT74728B/en unknown
- 1982-04-08 ZM ZM25/82A patent/ZM2582A1/en unknown
- 1982-04-08 TR TR21520A patent/TR21520A/en unknown
- 1982-04-08 JP JP57057425A patent/JPS57179126A/en active Pending
- 1982-04-08 BE BE0/207794A patent/BE892808A/en not_active IP Right Cessation
- 1982-04-08 PL PL23588082A patent/PL235880A1/xx unknown
- 1982-04-09 YU YU00789/82A patent/YU78982A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2503699A1 (en) | 1982-10-15 |
| LU84078A1 (en) | 1983-04-13 |
| ES8304051A1 (en) | 1983-02-16 |
| FR2503699B1 (en) | 1984-12-14 |
| NL8201473A (en) | 1982-11-01 |
| GB2096604A (en) | 1982-10-20 |
| RO83670A (en) | 1984-05-23 |
| ZA821810B (en) | 1983-01-26 |
| CH648275A5 (en) | 1985-03-15 |
| NZ200039A (en) | 1984-07-06 |
| YU78982A (en) | 1985-04-30 |
| PT74728B (en) | 1985-01-08 |
| KR850001733B1 (en) | 1985-12-07 |
| SE8202232L (en) | 1982-10-11 |
| PH16956A (en) | 1984-04-27 |
| CS233728B2 (en) | 1985-03-14 |
| JPS57179126A (en) | 1982-11-04 |
| PT74728A (en) | 1982-05-01 |
| KR830008963A (en) | 1983-12-16 |
| AR231527A1 (en) | 1984-12-28 |
| GR76143B (en) | 1984-08-03 |
| TR21520A (en) | 1987-04-10 |
| DK153082A (en) | 1982-10-11 |
| BR8201673A (en) | 1983-02-16 |
| ES511630A0 (en) | 1983-02-16 |
| ZW6182A1 (en) | 1982-10-20 |
| DD202525A5 (en) | 1983-09-21 |
| PL235880A1 (en) | 1982-10-25 |
| GB2096604B (en) | 1985-01-03 |
| BE892808A (en) | 1982-10-08 |
| MW1682A1 (en) | 1983-09-14 |
| RO83670B (en) | 1984-07-30 |
| DE3210435A1 (en) | 1982-10-28 |
| ZM2582A1 (en) | 1983-07-21 |
| AU8173882A (en) | 1982-10-14 |
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