SE445995B - PROCEDURE FOR THE PREPARATION OF METHYL-TERT.BUTYLETER - Google Patents
PROCEDURE FOR THE PREPARATION OF METHYL-TERT.BUTYLETERInfo
- Publication number
- SE445995B SE445995B SE7902561A SE7902561A SE445995B SE 445995 B SE445995 B SE 445995B SE 7902561 A SE7902561 A SE 7902561A SE 7902561 A SE7902561 A SE 7902561A SE 445995 B SE445995 B SE 445995B
- Authority
- SE
- Sweden
- Prior art keywords
- reactor
- methanol
- preparation
- methyl
- reaction mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920002125 Sokalan® Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 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
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000036632 reaction speed Effects 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
- 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
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
- 101100127285 Drosophila melanogaster unc-104 gene Proteins 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 239000002802 bituminous coal Substances 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
Description
7902561-5 Vi har nu funnit att högre omvandlingsgrader kan uppnås, om en del av reaktionsblandningen direkt recirkuleras. 7902561-5 We have now found that higher conversion rates can be achieved, if a portion of the reaction mixture is immediately recycled.
-Uppfinningen avser därför ett förfarande för framställning av mety]-tert.-butyleter genom omsättning av isobuten med metanol i närvaro av en katalysator, varvid reaktionen äger rum i vätskefas i en reaktor. Uppfinningen utmärks därvid av att en del av reaktionsblandningen från reaktorn direkt recirkuleras. Förfarandet enligt uppfinningen har visat sig ge en högre omvandlingsgrad vid konstant volymhastig~ het (LHSV) under i övrigt identiska betingelser, jämfört med då förfarandet utförs utan recirkulering. Fördelen med förfarandet enligt uppfinningen är att en mindre reaktor krävs, och som ytterligare fördel kan omnämnas att den relativt varma reaktoreffluenten onödiggör föruppvärmning av det tillförda råmaterialet under reaktionen.The invention therefore relates to a process for preparation of methyl] -ter.-butyl ether by reacting isobutene with methanol in the presence of a catalyst, the reaction taking place liquid phase in a reactor. The invention is thereby distinguished of that part of the reaction mixture from the reactor directly recycled. The method according to the invention has shown give a higher conversion rate at constant volume rate ~ (LHSV) under otherwise identical conditions, compared with when the process is performed without recycling. The advantage of the process of the invention is to a smaller reactor required, and as an additional benefit it may be mentioned that it relatively hot reactor effluent necessitates preheating of the feedstock added during the reaction.
Molförhållandet metanol till isobuten kan variera men ett molförhållande av l:l är mycket lämpligt.The molar ratio of methanol to isobutene may vary but one molar ratio of 1: 1 is very suitable.
Den temperatur vid vilken reaktionen äger rum ligger van~ ligtvis mellan 50 och l30°C, företrädesvis mellan 60 och l00°C.The temperature at which the reaction takes place is usual preferably between 50 and 130 ° C, preferably between 60 and 100 ° C.
Lämpliga tryck, vid vilka reaktionen kan utföras, är 5450 bar eller däröver.Suitable pressures at which the reaction can be carried out are 5450 bar or more.
De använda katalysatorerna är katjonbytare, som innehål- ler sulfonsyragrupper och är baserade på vinylaromatiska ' polymerer. Sådana jonbytare beskrivs i den holländska I patentansökan 273 294. Andra sulfonerade hartser är även lämpliga, såsom sulfonerat kol erhållet genom 7902561-5 behandling av bituminöst kol med svavelsyra och sulfonerade fenol-formaldehydhartser. An- dra lämpliga produkter är sulfonerade hartser av kumaron-in- den med cyklopentadien, sulfonerade hartser av kumaron-inden med fulfural och sulfonerade hartser såsom av cyklopentadienïmfl furfural. Det är föredraget att såsom katalysatorer använda katjonbytare, som i huvudsak utgörs av sulfonerat polystyren- harts, exempelvis en tvärförbunden divinylbensen-polystyren- matris med 0,5-20 % sampolymeriserad divinylbensen innehål- lande joniserbara sulfonsyragrupper. Andra lämpliga katalysa- torer är perfluorerade polymerer eller sampolymerer, som lika- ledes innehåller sulfonsyragrupper.The catalysts used are cation exchangers, which contain sulfonic acid groups and are based on vinyl aromatic 'polymers. Such ion exchangers are described in the Dutch I patent application 273 294. Other sulfonated resins are also suitable, such as sulfonated carbon obtained by 7902561-5 treatment of bituminous coal with sulfuric acid and sulfonated phenol-formaldehyde resins. An- suitable products are sulfonated coumaron-in-resin the one with cyclopentadiene, sulfonated resins of coumarone-indene with fulfural and sulphonated resins such as cyclopentadienim fl furfural. It is preferred to use as catalysts cation exchanger, which consists essentially of sulfonated polystyrene resin, for example a crosslinked divinylbenzene-polystyrene- matrix with 0.5-20% copolymerized divinylbenzene containing ionizable sulfonic acid groups. Other suitable catalysts are perfluorinated polymers or copolymers, which are led contains sulfonic acid groups.
Exempel på lämpliga hartser är Amberlite IR-12 OH, Amberlite 200, Amberlyst 15 Hkf- , Dowex 50-X-4, Dowex M5C-lH, Duolite C-26, Permutit QH, Chempro-C-20 och Imac C8P/H\f . En speci- ellt lämplig katalysator är Duolite C-26, som ger en hög reak- tionshastighet. Vid framställningen av etern är reaktions- hastigheten ca 2 gånger högre med Duolite C-26 såsom kataly- gator än med Amberlyst 15 H såsom katalysator. Jonbytar- kapaciteten hos syrahartset är företrädesvis minst 2,0 mekv, H+/g torrharts, i synnerhet 3,0 - 5,5 mekv. H+/g torrharts.Examples of suitable resins are Amberlite IR-12 OH, Amberlite 200, Amberlyst 15 Hkf-, Dowex 50-X-4, Dowex M5C-1H, Duolite C-26, Permutit QH, Chempro-C-20 and Imac C8P / H \ f. A speci- The most suitable catalyst is Duolite C-26, which gives a high reaction speed. In the preparation of the ether, the reaction speed about 2 times higher with Duolite C-26 as a catalyst streets than with Amberlyst 15 H as catalyst. Jonbytar- the capacity of the acid resin is preferably at least 2.0 meq, H + / g dry resin, in particular 3.0 - 5.5 meq. H + / g dry resin.
Recirkuleringen utförs företrädesvis på ett sådant sätt att viktförhållandet recirkulerad ström till ström av isobuten- och metanolbasmaterial är från(L5:l till 6:1. Det före- dragna viktförhâllandet är från l:l till 2:1.The recycling is preferably performed in such a way that weight ratio recycled stream to stream of isobutylene and methanol base material is from (L5: 1 to 6: 1). drawn weight ratio is from 1: 1 to 2: 1.
Ehuru en högre omvandlingsgrad uppnås genom recirkulering av reaktionsblandningen kan omvandlingen till metyl-tert.-butyl- eter uppgå till 95% om en andra reaktor anordnas nedströms hu- vudreaktorn. Efter att reaktionsblandningen har lämnat det för- sta reaktorsystemet (med recirkulering) kyls blandningen till ca 7000 och inmatas därefter i den andra reaktorn i syfte att låta isobutenen och metanolen reagera vidare. 7902561-5 Reaktionsblandningen kan renas ytterligare från isobuten och metanol men det är även möjligt att avlägsna endast isobute- nen och att använda metyl-tert.butyletern, som fortfarande innehåller metanol, exempelvis såsom komponent i lågblyben- sin eller blyfri bensin i syfte att öka bensinens oktantal.Although a higher degree of conversion is achieved by recycling the reaction mixture, the conversion to methyl tert-butyl ether to 95% if a second reactor is arranged downstream of the vudreaktorn. After the reaction mixture has left the pre- The reactor system (with recirculation) cools the mixture about 7000 and is then fed into the second reactor in order to allow the isobutene and methanol to react further. 7902561-5 The reaction mixture can be further purified from isobutylene and methanol but it is also possible to remove only isobutylene and to use the methyl tert-butyl ether, which is still contains methanol, for example as a component in low-lead its or unleaded petrol in order to increase the octane number of petrol.
Spår av i reaktionsblandningen närvarande syra, som härrör från katalysatorn, kan exempelvis avlägsnas genom behandling med aktiv aluminiumoxid. För detta ändamål får reaktionsblandning- en passera ett kärl med aktiv aluminiumoxid och neutralise- ras där. Aluminiumoxiden förnyas regelbundet eller behandlas med en 2-%-ig vattenlösning av natriumkarbonat och används_pâ nytt.Traces of acid present in the reaction mixture, from the catalyst, can be removed, for example, by treatment with active alumina. For this purpose, the reaction mixture a pass a vessel with active alumina and neutralize race there. The alumina is regularly renewed or treated with a 2% aqueous solution of sodium carbonate and used new.
Uppfinningen åskådliggörs närmare medelst följande utförings- exempel, vari temperaturangivelserna avser Celsiusgrader.The invention is further illustrated by the following embodiments. examples, in which the temperature indications refer to degrees Celsius.
Exempel l En reaktor (0,3 liter) fylldes delvis med en vattenhaltig upp- slamning innehållande 90 g (torr) sulfonerat styren-divinylben- sen-syrajonbytarharts med en jonbytarkapacitet av 4,75 mekv.Example 1 A reactor (0.3 liters) was partially filled with an aqueous solution. slurry containing 90 g (dry) of sulfonated styrene-divinylbenzene late-acid ion exchange resin with an ion exchange capacity of 4.75 meq.
H+/g torrharts, och hartset tvättades därefter med torr metanol för erhållande av en vattenfri hartsbädd.H + / g dry resin, and the resin was then washed with dry methanol to obtain an anhydrous resin bed.
Ett utgångsmaterial av metanol och isobuten (molförhållande l,25:l) matades kontinuerligt genom reaktorn vid ett tryck av 25 bar och med en volymhastighet av 50 l.l katalysator'l.h_l, och reaktionsblandningen avdrogs kontinuerligt. Utgångsmate- rialets begynnelsetemperatur var 700 och temperaturen vid re- aktorutloppet var 1300. Omvandlingen av metanol och isobuten till metyl-tert.butyleter uppmättes i effluentströmmen. Omvand- lingen till metyl-tert.butyleter var 73% (räknat på isobuten).A starting material of methanol and isobutene (molar ratio 1.25: 1) was fed continuously through the reactor at a pressure of 25 bar and with a volume rate of 50 l.l catalyst'l.h_l, and the reaction mixture was continuously withdrawn. Starting material the initial temperature of the material was 700 and the temperature at the prosecutor outlet was 1300. The conversion of methanol and isobutylene to methyl tert-butyl ether was measured in the effluent stream. Trans- The yield of methyl tert-butyl ether was 73% (based on isobutylene).
Exempel 2 (enligt uppfinningen) Exempel l upprepades men med den skillnaden att den reaktions- blandning som uttogs från reaktorn uppdelades i två strömmar.Example 2 (according to the invention) Example 1 was repeated but with the difference that the reaction mixture taken from the reactor was divided into two streams.
En ström rvcirkulerades via en ledning till reaktorns inlopp, 7902561-5 varvid viktförhållandet recirkulerad ström till den tillförda blandningen av metanol och isobuten uppgick till 1,5. Även i detta fall var utgångsmaterialets volymhastighet 50 1.1 kataly- -1 -1 sator .h . let passera en förvärmningsanordning i syfte att inställa dess Det var icke nödvändigt att låta utgängsmateria- temperatur på 700. Temperaturen vid reaktorutloppet var 1040.A stream was circulated via a line to the reactor inlet, 7902561-5 wherein the weight ratio of recirculated current to the supplied the mixture of methanol and isobutene was 1.5. Also in in this case, the volume rate of the starting material was 50 1.1. -1 -1 sator .h. passed a preheater in order to set it It was not necessary to allow the starting material temperature of 700. The temperature at the reactor outlet was 1040.
Den andra strömmen avdrogs och omvandlingen till metyl-tertJnu- tyleter fastställdes. Omvandlingsgraden var 84 % (räknat på isobuten) .The second stream was withdrawn and the conversion to methyl tert-ion tyl ether was determined. The conversion rate was 84% (calculated on isobutene).
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7803135A NL7803135A (en) | 1978-03-23 | 1978-03-23 | PROCESS FOR PREPARING TERTIARY ALKYL ETHERS. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7902561L SE7902561L (en) | 1979-09-24 |
| SE445995B true SE445995B (en) | 1986-08-04 |
Family
ID=19830543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7902561A SE445995B (en) | 1978-03-23 | 1979-03-21 | PROCEDURE FOR THE PREPARATION OF METHYL-TERT.BUTYLETER |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS54130508A (en) |
| CA (1) | CA1131662A (en) |
| CH (1) | CH638477A5 (en) |
| DE (1) | DE2911077A1 (en) |
| FR (1) | FR2420518A1 (en) |
| GB (1) | GB2017693B (en) |
| IT (1) | IT1112964B (en) |
| NL (1) | NL7803135A (en) |
| SE (1) | SE445995B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2440931A1 (en) | 1978-11-08 | 1980-06-06 | Inst Francais Du Petrole | PROCESS FOR PRODUCING ETHERS BY REACTION OF OLEFINS WITH ALCOHOLS |
| US4262146A (en) | 1980-01-15 | 1981-04-14 | Phillips Petroleum Company | Production of aliphatic ethers |
| FR2481269A1 (en) * | 1980-04-28 | 1981-10-30 | Inst Francais Du Petrole | PROCESS FOR PRODUCING ETHERS BY REACTING OLEFINS WITH ALCOHOLS |
| CA1254236A (en) * | 1981-07-27 | 1989-05-16 | Donald J. Makovec | Process for the preparation of methyl tert-butyl ether |
| CN100509734C (en) * | 2001-06-28 | 2009-07-08 | 日本瑞翁株式会社 | Solvents containing cycloalkyl alkyl ethers and process for production of the ethers |
| FR2969147B1 (en) | 2010-12-21 | 2013-01-04 | Total Raffinage Marketing | PRODUCTION OF FUEL ADDITIVES BY DEHYDRATION AND SIMULTANEOUS SKELETAL ISOMERISATION OF ISOBUTANOL ON ACID CATALYSTS FOLLOWED BY ETHERIFICATION |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2629769B2 (en) * | 1976-07-02 | 1980-03-13 | Chemische Werke Huels Ag, 4370 Marl | Process for the production of pure methyl tertiary butyl ether |
| JPS5938933B2 (en) * | 1976-11-22 | 1984-09-20 | 日石三菱株式会社 | Continuous production method of tertiary alkyl ether |
-
1978
- 1978-03-23 NL NL7803135A patent/NL7803135A/en not_active Application Discontinuation
-
1979
- 1979-02-20 CA CA321,866A patent/CA1131662A/en not_active Expired
- 1979-03-20 JP JP3185779A patent/JPS54130508A/en active Granted
- 1979-03-21 FR FR7907141A patent/FR2420518A1/en active Granted
- 1979-03-21 CH CH267079A patent/CH638477A5/en not_active IP Right Cessation
- 1979-03-21 DE DE19792911077 patent/DE2911077A1/en active Granted
- 1979-03-21 SE SE7902561A patent/SE445995B/en not_active IP Right Cessation
- 1979-03-21 IT IT21194/79A patent/IT1112964B/en active
- 1979-03-21 GB GB7909977A patent/GB2017693B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE7902561L (en) | 1979-09-24 |
| IT1112964B (en) | 1986-01-20 |
| CA1131662A (en) | 1982-09-14 |
| FR2420518B1 (en) | 1984-06-29 |
| JPS54130508A (en) | 1979-10-09 |
| NL7803135A (en) | 1979-09-25 |
| DE2911077C2 (en) | 1988-10-06 |
| IT7921194A0 (en) | 1979-03-21 |
| JPS6339577B2 (en) | 1988-08-05 |
| DE2911077A1 (en) | 1979-10-04 |
| GB2017693A (en) | 1979-10-10 |
| CH638477A5 (en) | 1983-09-30 |
| GB2017693B (en) | 1982-08-11 |
| FR2420518A1 (en) | 1979-10-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7026519B2 (en) | Obtaining tert-butanol | |
| US4256465A (en) | Method for producing methyl tert-butyl ether and fuel composition containing the same | |
| US4570026A (en) | Production of isobutene from methyl tertiary butyl ether | |
| SU1132787A3 (en) | Method of obtaining isobutene | |
| KR20070070093A (en) | Process for fine purification of 1-butenic streams | |
| US4404409A (en) | Process for preparing methyl tertiary-butyl ether | |
| US4180688A (en) | Method for continuously producing tert-butyl alcohol | |
| US5371301A (en) | Single stage diisopropyl ether process using aqueous extraction and ion exchange treating for SO3 removal | |
| JP4292072B2 (en) | Production of t-butanol | |
| SE445995B (en) | PROCEDURE FOR THE PREPARATION OF METHYL-TERT.BUTYLETER | |
| US5324866A (en) | Integrated process for producing diisopropyl ether from isopropyl alcohol | |
| EP0366501B1 (en) | Heat integration process | |
| US4322565A (en) | Process for purifying ethers | |
| US4546206A (en) | Process for producing methyl tert. alkyl ether | |
| US5600023A (en) | Single stage diisopropyl ether process using organic solvent aqueous extraction and ion exchange treating for SO3 removal | |
| WO1992001661A1 (en) | Reactor quenching for catalytic olefin hydration in ether production | |
| EP0579153A2 (en) | Process for producing tertiary alcohol, and for preparing catalyst therefor | |
| KR101088407B1 (en) | Method for producing tert-butanol by means of reactive rectification | |
| EP0075838A1 (en) | Process for the preparation of methyl tert-butyl ether | |
| US3362987A (en) | Process for producing acetic acid | |
| CA1195699A (en) | Production of aliphatic ethers | |
| US4262146A (en) | Production of aliphatic ethers | |
| US5399788A (en) | Two-stage process for producing diisopropyl ether using hydration | |
| JPS6058893B2 (en) | Method for producing tertiary alcohol | |
| KR830002476B1 (en) | Method for preparing methyl t-butyl ether |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
Ref document number: 7902561-5 Effective date: 19931008 Format of ref document f/p: F |