NO831759L - PROCEDURE FOR THE PREPARATION OF TERT. BUTYL ethers - Google Patents
PROCEDURE FOR THE PREPARATION OF TERT. BUTYL ethersInfo
- Publication number
- NO831759L NO831759L NO831759A NO831759A NO831759L NO 831759 L NO831759 L NO 831759L NO 831759 A NO831759 A NO 831759A NO 831759 A NO831759 A NO 831759A NO 831759 L NO831759 L NO 831759L
- Authority
- NO
- Norway
- Prior art keywords
- butene
- isobutene
- tert
- hydrocarbon
- alkyl ether
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 title 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 56
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 52
- 239000004215 Carbon black (E152) Substances 0.000 claims description 24
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 23
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 21
- 229930195733 hydrocarbon Natural products 0.000 claims description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims description 20
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 18
- -1 butyl alkyl ethers Chemical class 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 238000006317 isomerization reaction Methods 0.000 claims description 11
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 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 description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000005194 fractionation Methods 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 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 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000010702 ether synthesis reaction Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 235000012976 tarts Nutrition 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 239000001282 iso-butane Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
-
- 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)
Description
Foreliggende oppfinnelse vedrører en fremgangsmåte for fremstilling av tert.butyl-alkyletere fra en C^-hydro-karbontilførsel som eventuelt også inneholder C 3 og C^-komponenter hvorfra butadienet på forhånd er blitt separert, bestående i å tilføre C^-hydrokarbontilførselen fri for eller hovedsakelig fri for butadien til en tert.butyl-alkyleter-synteseseksjon inneholdende en katalysator som utgjøres av en sur ionebytterharpiks, foretrukket av den sulfonerte divinylbenzen-styrentype, reagerer isobutenet inneholdt iC^-hydrokarbontilførselen med en alifatisk alkohol for å fremstille en tert.butyl-alkyleter og separere tert.butyl-alkyleteren fra de resterende C^-hydrokarboner, og det sær-egne ved fremgangsmåten i henhold til oppfinnelsen er at de resterende C^-hydrokarboner underkastes en fraksjonering i to eller flere trinn for å separere de mettede hydrokarboner fra buten-1 og buten-2 og buten-1 og/eller buten-2 føres til et isomeriseringstrinn hvor de delvis omdannes til isobuten for oppnåelse av en hydrokarbonfraksjon inneholdende hovedsakelig buten-1, buten-2 og isobuten sammen med tunge produkter, idet hydrokarbonfraksjonen hovedsakelig inneholder buten-1, buten-2 og isobuten og eventuelt en del av de tunge og mettede komponenter som føres til tert.butyl-alkyleter-sytesereaksjonen. The present invention relates to a method for the production of tert.butyl alkyl ethers from a C 3 -hydrocarbon feed which possibly also contains C 3 and C 3 -components from which the butadiene has been previously separated, consisting in adding the C 3 -hydrocarbon feed free of or substantially free of butadiene to a tert-butyl alkyl ether synthesis section containing a catalyst consisting of an acidic ion exchange resin, preferably of the sulfonated divinylbenzene-styrene type, the isobutene contained in the C 1 -hydrocarbon feed reacts with an aliphatic alcohol to produce a tert-butyl -alkyl ether and separate the tert-butyl alkyl ether from the remaining C 1 hydrocarbons, and the peculiarity of the method according to the invention is that the remaining C 1 hydrocarbons are subjected to a fractionation in two or more stages in order to separate the saturated hydrocarbons from butene-1 and butene-2 and butene-1 and/or butene-2 are taken to an isomerization step where they are partially converted to isobutene for up reaching a hydrocarbon fraction containing mainly butene-1, butene-2 and isobutene together with heavy products, the hydrocarbon fraction mainly containing butene-1, butene-2 and isobutene and optionally part of the heavy and saturated components which are carried to tert.butyl- the alkyl ether synthesis reaction.
Disse og andre trekk ved oppfinnelsen fremgår av patentkravene. These and other features of the invention appear in the patent claims.
Oppfinnelsen vedrører spesielt en fremgangsmåte for fremstilling av tert.butyl-metyleter. The invention relates in particular to a method for the production of tert-butyl methyl ether.
Det er kjent mange prosesser på området for fremstilling av tert.butyl-alkyletere, bestående av å reagere isobuten, inneholdt i hydrokarbonstrømmer av forskjellig opprinnelse og spesielt i strømmen som skriver seg fra damp-cracking, katalytisk cracking eller dehydrogenering av isobutan, med en alkohol, foretrukket metanol eller etanol, i nærvær av en sur ionebytterharpiks og i denne forbindelse refereres til Many processes are known in the field for the production of tert.butyl alkyl ethers, consisting of reacting isobutene, contained in hydrocarbon streams of various origins and especially in the stream resulting from steam-cracking, catalytic cracking or dehydrogenation of isobutane, with an alcohol , preferably methanol or ethanol, in the presence of an acidic ion exchange resin and in this connection is referred to
de italienske patentskrifter 1.012.686, 1.012.690.the Italian patents 1,012,686, 1,012,690.
De kjente prosesser tillater en nesten total isobutenom-dannelse, men de andre komponenter forblir praktisk - uendret og kan derfor ikke anvendes direkte som sådanne som bensinkomponenter. The known processes allow an almost total isobutene formation, but the other components remain practically unchanged and therefore cannot be used directly as such as gasoline components.
Fremgangsmåten i henhold til den foreliggende oppfinnelse tillater omdannelse av en del av de andre komponenter enn isobutenet, i hydrokarbontilførselen med fire karbonatomer til tert.butyl-alkyletere, sammen med isobutenet som opp-rinnelig var inneholdt i tilførselen. The method according to the present invention allows the conversion of a part of the components other than the isobutene in the hydrocarbon feed with four carbon atoms to tert-butyl alkyl ethers, together with the isobutene which was originally contained in the feed.
Fremgangsmåten i henhold til oppfinnelsen består mer detaljert av følgende trinn: 1)C^-hydrokarbontilførselen, enten fri for eller hovedsakelig fri for butadien, tilføres en tert.butyl-alkyleter-synteseseksjon inneholdende en katalysator som utgjøres av en sur ionebytterharpiks, foretrukket av den sulfonerte divinylbenzen-styrentype. 2) Isobutenet inneholdt i C^-hydrokarbontilførselen fra punkt 1) reageres med en alifatisk alkohol tilført synteseseksjonen, idet den molare forhold mellom alkohol og isobuten er mellom 0,9 og 1,3 idet reaksjoneproduktet er en tert.butyl-alkyleter. 3) Tert. butyl-=alkyleteren separeres fra C^-hydrokarbonene ved destillasjon enten i den samme reaksjonssone eller i en separat sone. 4) Fraksjonering av den resterende C^-hydrokarbontilførsel i to eller tre trinn ved en temperatur på mellom 40 og 130°C og et trykk på mellom 4 ata og 26 ata under anvendelse av mellom 100 og 200 plater for å separere de mettede hydrokarboner (butan og. isobutan) fra buten-1 og buten-2. 5) Buten-1 og/eller buten-2 og de useparerte mettede komponenter fra trinn 4) føres til et isomeriseringstrinn hvori buten-1 og/eller buten-2 omdannes delvis til isobuten til uavhengig av utgangsolefinet eller utgangsblandingen å oppnå en hydrokarbonfraksjon inneholdende hovedsakelig buten-1, buten-2 og isobuten hvori det molare forhold buten-1/ buten-;2 tilsvarer, praktisk termodynamisk likevekt, mens det molare forhold isobuten/lineært buten ligger mellom 0,6 og 0,3. 6) Hydrokarbonfraksjonen inneholdende buten-1, buten-2 og isobuten separeres fra de tunge produkter. 7) Hydrokarbonfraksjonen inneholdende buten-1, buten-2 og isobuten og eventuelt også en del av de tunge og mettede komponenter tilføres tert.butyl-alkyleter-synteseseksjonen enten direkte eller etter blanding med C^-hydrokarbonstrømmen som er fri for eller hovedsakelig fri for butadien. C^-hydrokarbontilførselen inneholder eventuelt også C3og C^-komponenter. The method according to the invention consists in more detail of the following steps: 1) The C₁-hydrocarbon feed, either free of or substantially free of butadiene, is fed to a tert-butyl alkyl ether synthesis section containing a catalyst consisting of an acidic ion exchange resin, preferred by the sulfonated divinylbenzene-styrene type. 2) The isobutene contained in the C1 hydrocarbon feed from point 1) is reacted with an aliphatic alcohol supplied to the synthesis section, the molar ratio between alcohol and isobutene being between 0.9 and 1.3, the reaction product being a tert-butyl alkyl ether. 3) Tart. the butyl-=alkyl ether is separated from the C₁ hydrocarbons by distillation either in the same reaction zone or in a separate zone. 4) Fractionation of the remaining C₁ hydrocarbon feed in two or three stages at a temperature of between 40 and 130°C and a pressure of between 4 ata and 26 ata using between 100 and 200 plates to separate the saturated hydrocarbons ( butane and isobutane) from butene-1 and butene-2. 5) Butene-1 and/or butene-2 and the unseparated saturated components from step 4) are fed to an isomerization step in which butene-1 and/or butene-2 are partially converted to isobutene to obtain, independently of the starting olefin or the starting mixture, a hydrocarbon fraction containing mainly butene-1, butene-2 and isobutene in which the molar ratio butene-1/butene-;2 corresponds to practical thermodynamic equilibrium, while the molar ratio isobutene/linear butene lies between 0.6 and 0.3. 6) The hydrocarbon fraction containing butene-1, butene-2 and isobutene is separated from the heavy products. 7) The hydrocarbon fraction containing butene-1, butene-2 and isobutene and possibly also a part of the heavy and saturated components is supplied to the tert-butyl alkyl ether synthesis section either directly or after mixing with the C^-hydrocarbon stream which is free of or mainly free of butadiene. The C2 hydrocarbon feed possibly also contains C3 and C2 components.
C^-tilførselen omfatter normalt C^-hydrokarboner, isobutan, isobuten, buten-1, n-butan, trans-buten-2, cis-buten-2 og C,--hydrokarboner. C og C,.-hydrokarboner er i små mengder The C2 feed normally comprises C2 hydrocarbons, isobutane, isobutene, butene-1, n-butane, trans-butene-2, cis-butene-2 and C2 hydrocarbons. C and C,.-hydrocarbons are in small amounts
og de andre kan være i relative mengder som kan variere sterkt alt etter opprinnelsen. and the others can be in relative amounts that can vary greatly depending on the origin.
For å oppnå et konstant molart forhold mellom buten-1, buten-2 og isobuten gjennomføres isomerisering av buten-1, og/eller buten-2 under anvendelse av en prosess som beskrevet i italiensk patentskrift nr. 1.017.878 med en katalysator basert på silisiumholdig aluminiumoksyd som f.eks. beskrevet i US-patentskrift 4.013.589 og 4.013.590. Det er interes-sant å merke at fremgangsmåten i henhold til oppfinnelsen muliggjør ikke bare oppnåelse av tert.butyl-alkyletere men eventuelt også rent buten-1 eller alternativt buten-2, som kan anvendes for andre formål enn dem nevnt heri. In order to achieve a constant molar ratio between butene-1, butene-2 and isobutene, isomerization of butene-1 and/or butene-2 is carried out using a process as described in Italian patent document no. 1,017,878 with a catalyst based on silicon-containing alumina such as e.g. described in US Patents 4,013,589 and 4,013,590. It is interesting to note that the method according to the invention makes it possible not only to obtain tert-butyl alkyl ethers, but possibly also pure butene-1 or alternatively butene-2, which can be used for purposes other than those mentioned herein.
Fremgangsmåten i henhold til oppfinnelsen kan følgelig anvendes under mange forhold og det er funnet at engod vesentlige variasjoner i isobuteninnholdet av strømmen tilført synteseseksjonen ikke endrer arbeidsbetingelsene for syntesen. The method according to the invention can consequently be used under many conditions and it has been found that even significant variations in the isobutene content of the stream supplied to the synthesis section do not change the working conditions for the synthesis.
Fremgangsmåten i henhold til oppfinnelsen illustreres i det etterfølgende med henvisning til den vedføyde figur hvori 1 indikerer C^-hydrokarbontilførselen fri for eller hovedsakelig fri for butadien, 2 viser strømmen fra isomeriseringsreaktoren 13 omfattende buten-1, buten-2 og isobuten, og en hvis mengde av mettede hydrokarboner, 3 viser den totale strøm av 1 og 2 og 4 idet synteseenheten for tert.butyl-metyleter (MTBE), MTBE-strømmen 5, metanolstrømmen 6 tilført til synteseseksjonen, C^-fraksjonen 7 hovedsakelig fri for isobuten, et mulig selektivt hydrogeneringstrinn 19 for restbutadien og eventuelle acetylenforbindelser, tilførsels-strømmen 8 til fraksjoneringsseksjonen for de mettede hydrokarboner og olefiner, kolonnen 9 for separering av isobutanet 10, kolonnen 11 for separering av buten-1 i strømmen 12, The method according to the invention is illustrated in the following with reference to the attached figure in which 1 indicates the C₁ hydrocarbon feed free of or substantially free of butadiene, 2 shows the flow from the isomerization reactor 13 comprising butene-1, butene-2 and isobutene, and one whose amount of saturated hydrocarbons, 3 shows the total stream of 1 and 2 and 4 being the tert-butyl methyl ether (MTBE) synthesis unit, the MTBE stream 5, the methanol stream 6 fed to the synthesis section, the C^ fraction 7 essentially free of isobutene, a possible selective hydrogenation step 19 for residual butadiene and any acetylene compounds, feed stream 8 to the fractionation section for the saturated hydrocarbons and olefins, column 9 for separating the isobutane 10, column 11 for separating butene-1 in stream 12,
og kolonnen 13 for separering av n-butan i strømmen 14 fra cis- og trans-buten-2 i strømmen 15. and the column 13 for separating n-butane in stream 14 from cis- and trans-butene-2 in stream 15.
Buten-l-strømmen 12 kan tilføres isomeriseringsreaktorenThe butene-1 stream 12 can be fed to the isomerization reactor
16 gjennom ledningen 17, eller kan tas ut med nødvendig renhet gjennom ledningen 18. 20 representerer hydrogen-strømmen. Tabell 1 illustrerer noen eksempelvise eksperimentelle arbeidsbetingelser sammen med de relative resultater oppnådd ved fremgangsmåten i henhold til oppfinnelsen med henvisning til tegningen under anvendelse av den selektive hydrogeneringsenhet 19 og hydrogenstrømmen 20 16 through line 17, or can be taken out with the necessary purity through line 18. 20 represents the hydrogen flow. Table 1 illustrates some exemplary experimental working conditions together with the relative results obtained by the method according to the invention with reference to the drawing using the selective hydrogenation unit 19 and the hydrogen stream 20
men uten resirkulering av buten-1 til isomeriseringssonen. but without recycling the butene-1 to the isomerization zone.
Tabell 2 illustrerer eksempelvise eksperimentelle arbeidsbetingelser og resultater oppnådd ved fremgangsmåten i henhold til oppfinnelsen, på nytt med henvisning til figuren, uten å anvende den selektive hydrogeneringssone 19 men med resirkulering av buten-1 til isomeriseringssonen. Table 2 illustrates exemplary experimental working conditions and results obtained by the method according to the invention, again with reference to the figure, without using the selective hydrogenation zone 19 but with recycling of butene-1 to the isomerization zone.
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21384/82A IT1151183B (en) | 1982-05-20 | 1982-05-20 | PROCEDURE FOR THE PRODUCTION OF TER-BUTYL ALCHYL ETHERS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO831759L true NO831759L (en) | 1983-11-21 |
Family
ID=11180967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO831759A NO831759L (en) | 1982-05-20 | 1983-05-18 | PROCEDURE FOR THE PREPARATION OF TERT. BUTYL ethers |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS58210039A (en) |
| KR (1) | KR860001854B1 (en) |
| AU (1) | AU1401783A (en) |
| BE (1) | BE896787A (en) |
| BG (1) | BG37678A3 (en) |
| BR (1) | BR8302433A (en) |
| CA (1) | CA1220230A (en) |
| CH (1) | CH653664A5 (en) |
| DD (1) | DD209803A5 (en) |
| DE (1) | DE3318301A1 (en) |
| DK (1) | DK221683A (en) |
| ES (1) | ES523006A0 (en) |
| FR (1) | FR2527202B1 (en) |
| GB (1) | GB2121407B (en) |
| GR (1) | GR78857B (en) |
| IN (1) | IN159788B (en) |
| IT (1) | IT1151183B (en) |
| LU (1) | LU84805A1 (en) |
| MW (1) | MW1883A1 (en) |
| NL (1) | NL8301819A (en) |
| NO (1) | NO831759L (en) |
| NZ (1) | NZ204032A (en) |
| PH (1) | PH19481A (en) |
| PL (1) | PL242093A1 (en) |
| PT (1) | PT76730B (en) |
| SE (1) | SE8302577L (en) |
| TR (1) | TR21617A (en) |
| YU (1) | YU110083A (en) |
| ZA (1) | ZA833068B (en) |
| ZW (1) | ZW9783A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4731490A (en) * | 1986-07-23 | 1988-03-15 | Arco Chemical Company | Process for methyl, tertiary butyl ether production |
| FR2614297B1 (en) * | 1987-04-24 | 1989-07-21 | Inst Francais Du Petrole | PROCESS FOR PRODUCING METHYL-TERTIOBUTYL-ETHER FROM N-BUTENES. |
| CA2111018A1 (en) * | 1993-01-06 | 1994-07-07 | Jacob N. Rubin | Integrated mtbe process |
| FR2710907B1 (en) * | 1993-10-08 | 1996-01-05 | Inst Francais Du Petrole | Process for the production of tertiary ethers from a catalytic cracking charge comprising two stages of extractive distillation. |
| IT1270675B (en) | 1994-10-19 | 1997-05-07 | Enichem Spa | PROCEDURE FOR THE SEPARATION OF PARAFFINS IN MIXTURE WITH OLEFINS |
| CN103755512B (en) * | 2013-12-24 | 2016-01-06 | 山东滨州裕华化工厂有限公司 | The technique of liquefied gas separation of C 4 cut after ether |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1224294B (en) * | 1961-01-09 | 1966-09-08 | Bayer Ag | Process for the production of tertiary butyl alkyl ethers |
| FR2455019A1 (en) * | 1979-04-24 | 1980-11-21 | Inst Francais Du Petrole | PROCESS FOR PRODUCING METHYLTERTIOBUTYL ETHER FROM METHANOL AND ISOBUTENE |
| DE2921576A1 (en) * | 1979-05-28 | 1980-12-04 | Davy International Ag | METHOD FOR THE PRODUCTION OF METHYL-TERT.-BUTYLAETHER |
-
1982
- 1982-05-20 IT IT21384/82A patent/IT1151183B/en active
-
1983
- 1983-04-28 GR GR71241A patent/GR78857B/el unknown
- 1983-04-28 NZ NZ204032A patent/NZ204032A/en unknown
- 1983-04-28 AU AU14017/83A patent/AU1401783A/en not_active Abandoned
- 1983-04-29 ZW ZW97/83A patent/ZW9783A1/en unknown
- 1983-04-29 ZA ZA833068A patent/ZA833068B/en unknown
- 1983-05-05 CH CH2465/83A patent/CH653664A5/en not_active IP Right Cessation
- 1983-05-05 SE SE8302577A patent/SE8302577L/en not_active Application Discontinuation
- 1983-05-06 BR BR8302433A patent/BR8302433A/en unknown
- 1983-05-12 GB GB08313098A patent/GB2121407B/en not_active Expired
- 1983-05-13 KR KR1019830002066A patent/KR860001854B1/en active
- 1983-05-13 MW MW18/83A patent/MW1883A1/en unknown
- 1983-05-13 LU LU84805A patent/LU84805A1/en unknown
- 1983-05-17 FR FR8308163A patent/FR2527202B1/en not_active Expired
- 1983-05-17 YU YU01100/83A patent/YU110083A/en unknown
- 1983-05-18 BG BG8361013A patent/BG37678A3/en unknown
- 1983-05-18 DK DK221683A patent/DK221683A/en not_active Application Discontinuation
- 1983-05-18 NO NO831759A patent/NO831759L/en unknown
- 1983-05-18 TR TR21617A patent/TR21617A/en unknown
- 1983-05-18 PH PH28926A patent/PH19481A/en unknown
- 1983-05-19 CA CA000428516A patent/CA1220230A/en not_active Expired
- 1983-05-19 DE DE19833318301 patent/DE3318301A1/en not_active Withdrawn
- 1983-05-19 BE BE0/210806A patent/BE896787A/en not_active IP Right Cessation
- 1983-05-19 PT PT76730A patent/PT76730B/en unknown
- 1983-05-19 DD DD83251077A patent/DD209803A5/en unknown
- 1983-05-20 PL PL24209383A patent/PL242093A1/en unknown
- 1983-05-20 IN IN632/CAL/83A patent/IN159788B/en unknown
- 1983-05-20 ES ES523006A patent/ES523006A0/en active Granted
- 1983-05-20 JP JP58087816A patent/JPS58210039A/en active Pending
- 1983-05-20 NL NL8301819A patent/NL8301819A/en not_active Application Discontinuation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO831758L (en) | PROCEDURE FOR THE PREPARATION OF TERT. BUTYLAL COOLETERS AND BUTEN-1. | |
| US4423251A (en) | Process employing sequential isobutylene hydration and etherification | |
| US4503265A (en) | Process for the production of methyl tert.-butyl ether (MTBE) and of hydrocarbon raffinates substantially freed from i-butene and from methanol | |
| KR19980033193A (en) | Novel process for preparing isobutene and propylene from hydrocarbon classifications containing four carbon atoms | |
| GB2144145A (en) | Process for producing butene-1 | |
| EA019388B1 (en) | Production of light olefins and isoprene from butane | |
| CZ20013640A3 (en) | Process for preparing extremely pure raffinate II and methyl-tert-butyl ether | |
| JPS6245850B2 (en) | ||
| US5382707A (en) | Integrated MTBE process | |
| KR20070070093A (en) | Process for fine purification of 1-butenic streams | |
| JPH048413B2 (en) | ||
| US9260357B2 (en) | Hydrocarbon conversion process | |
| CS242853B2 (en) | Method of methyl-tertiary butyl ether preparation | |
| FI78675B (en) | FOERFARANDE FOER FRAMSTAELLNING AV EN BLANDNING AV TERT-BUTYLALKOHOL OCH SEC-BUTYL-TERT-BUTYLETER. | |
| US6159433A (en) | Plant for the conversion of olefinic C4 and C5 cuts to an ether and to propylene | |
| HU200977B (en) | Process for gaining of mixture of buthen-1 or buthen-1-izobuthen of big cleanness from fractions of c-below-4-hydrocarbon | |
| JP2691223B2 (en) | Increasing 2-methyl-2-butene concentration in isoamylene | |
| NO831759L (en) | PROCEDURE FOR THE PREPARATION OF TERT. BUTYL ethers | |
| US20040192994A1 (en) | Propylene production | |
| EP0514593B1 (en) | Production of ether from alcohol and isoolefin in the presence of H2O with H2O/alcohol recycle | |
| US4091046A (en) | Production of isoprene from isobutane | |
| US5399787A (en) | Olefin isomerization process using etherification feed isomerization | |
| ES8308824A1 (en) | Process for the separation of methyl tert-butyl ether from reaction mixtures containing it. | |
| NO874006L (en) | PROCEDURE FOR THE MANUFACTURING OF FUEL COMPONENTS FROM OLEFINES. | |
| US5723686A (en) | Recycle of alcohol in a combined hydroisomerization and etherification process |