NL8301819A - PROCESS FOR PREPARING TERT BUTYL ALKYL ETHERS. - Google Patents
PROCESS FOR PREPARING TERT BUTYL ALKYL ETHERS. Download PDFInfo
- Publication number
- NL8301819A NL8301819A NL8301819A NL8301819A NL8301819A NL 8301819 A NL8301819 A NL 8301819A NL 8301819 A NL8301819 A NL 8301819A NL 8301819 A NL8301819 A NL 8301819A NL 8301819 A NL8301819 A NL 8301819A
- Authority
- NL
- Netherlands
- Prior art keywords
- butene
- isobutene
- butyl alkyl
- hydrocarbon
- tert
- Prior art date
Links
- -1 TERT BUTYL ALKYL ETHERS Chemical class 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 55
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 23
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 21
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims abstract description 21
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 20
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 15
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 238000006317 isomerization reaction Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 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 claims 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 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- 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
- 239000001282 iso-butane Substances 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-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 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 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
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical class CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 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
- 239000000047 product Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000004230 steam cracking Methods 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)
Abstract
Description
·.. ......% 833052/vdV/kd· .. ......% 833052 / vdV / kd
Korte aanduiding: Werkwijze ter bereiding van tert.butylalkylethers .Short designation: Process for preparing tert-butyl alkyl ethers.
De uitvinding heeft betrekking op een werkwijze ter bereiding van tert.butylalkylethers.The invention relates to a process for preparing tert-butyl alkyl ethers.
Meer in het bijzonder heeft de uitvinding betrekking op een werkwijze ter bereiding van tert.butylmethyl-5 ether.More particularly, the invention relates to a process for preparing tert-butylmethyl-5 ether.
Er zijn veel werkwijzen bekend ter bereiding van tert.butylalkylethers, waarbij men isobuteen, dat aanwezig is in koolwaterstofstromen van verschillende oorsprong en in het bijzonder afkomstig van stoomkraken, katalytisch kraken 10 of dehydrogeneren van isobutaan met een alcohol bij voorkeur methanol of ethanol, in tegenwoordigheid van een zuur ionenui twisselend hars laat reageren.Many processes are known for preparing tert-butyl alkyl ethers using isobutene, which is present in hydrocarbon streams of various origins, in particular from steam cracking, catalytic cracking or dehydrogenation of isobutane with an alcohol, preferably methanol or ethanol, in the present of an acidic ion onion twisting resin.
In dit verband kunnen de Italiaanse octrooischrif-ten 1.012.686, 1.012.687 en 1.012.690 worden genoemd.In this connection, Italian patents 1,012,686, 1,012,687 and 1,012,690 can be mentioned.
15 De bekende werkwijzen maken een vrijwel totale isobuteen omzetting mogelijk, doch de andere bestanddelen blijven vrijwel onveranderd, en kunnen derhalve niet als zodanig direkt als bestanddelen van benzine worden toegepast.The known processes permit almost total isobutylene conversion, but the other components remain virtually unchanged, and therefore cannot be used as such directly as petrol components.
De werkwijze volgens de onderhavige uitvinding maakt 20 de omzetting mogelijk van een gedeelte van de bestanddelen van de koolwaterstofvoeding met 4 koolstofatomen, met uitzondering van isobuteen, in tert.butylalkylethers, tezamen met het oorspronkelijk in de voeding aanwezige isobuteen.The process of the present invention allows the conversion of a portion of the components of the 4-carbon hydrocarbon feedstock, with the exception of isobutene, into tert-butyl alkyl ethers, along with the isobutylene originally present in the feed.
De werkwijze volgens de onderhavige uitvinding 25 omvat de volgende trappen: 1) Toevoeren van de (^-koolwaterstofvoeding, die vrij of vrijwel vrij is van butadieen, aan een zone voor de synthese van tert.butylalkylether, die een katalysator bevat bestaande uit een zuur-ionen uitwisselend hars, bij voorkeur 30 van het gesulfoneerde divinylbenzeen-styreen type.The process of the present invention includes the following steps: 1) Feeding the (--hydrocarbon feed, which is free or substantially free of butadiene, to a tert-butyl alkyl ether synthesis zone containing a catalyst consisting of an acid ion-exchange resin, preferably of the sulfonated divinylbenzene-styrene type.
2) Het in de C^-koolwaterstofvoeding van punt 1) aanwezige isobuteenlaten reageren met een alifatische alcohol die aan deze synthesezone wordt toegevoerd, waarbij de molaire verhouding van de alcohol ten opzichte van isobuteen 8301819 -2- i ligt tussen 0,9 en 1,3 en het reactieprodukt een tert-.butyl-alkylether is.2) The isobutylates present in the C 1 hydrocarbon feed of point 1) react with an aliphatic alcohol which is fed to this synthesis zone, the molar ratio of the alcohol to isobutene 8301819 -2-1 being between 0.9 and 1 , 3 and the reaction product is a tert-butyl alkyl ether.
3) De tert.butylalkylether scheiden van de C^-kool-waterstoffen door destillatie, ofwel in dezelfde reactie- 5 zone ofwel in een afzonderlijke zone.3) Separating the tert-butyl alkyl ether from the C 1 hydrocarbons by distillation, either in the same reaction zone or in a separate zone.
4) De overblijvende C^-koolwaterstofvoeding in twee of drie trappen bij een temperatuur van tussen 40°C en 130°C en een druk tussen 4 ata en 26 ata, fractioneren onder toepassing van 100 tot 220 platen om de verzadigde koolwater- 10 stoffen (butaan en isobutaan) te scheiden van buteen-1 en buteen-2.4) Fractionate the residual C 2 hydrocarbon feed in two or three stages at a temperature between 40 ° C and 130 ° C and a pressure between 4 ata and 26 ata using 100 to 220 plates to separate the saturated hydrocarbons. (butane and isobutane) to separate from butene-1 and butene-2.
5) Het buteen-1 en/of buteen 2 en de niet-afgescheiden verzadigde bestanddelen van trap 4) toevoeren aan een isomerisatietrap waarin buteen-1 en/of buteen-2 gedeeltelijk 15 worden omgezet in isobuteen, om onafhankelijk van het alkeen of het mengsel waarvan is uitgegaan, een koolwaterstoffractie te verkrijgen die voornamelijk buteen-1, buteen-2 en isobuteen bevat, waarin de molaire buteen-l/buteen-2 verhouding vrijwel overeenkomt met het thermodynamische evenwicht, 20 terwijl de molaire isobuteen/lineaire buteen verhouding ligt tussen 0,6 en 0,3.5) Feed the butene-1 and / or butene 2 and the non-separated saturated components of step 4) to an isomerization step in which butene-1 and / or butene-2 are partially converted into isobutylene, to be independent of the olefin or the starting mixture to obtain a hydrocarbon fraction containing mainly butene-1, butene-2 and isobutylene, in which the butene-1 / butene-2 molar ratio corresponds almost to the thermodynamic equilibrium, while the isobutylene / linear butene molar ratio is between 0.6 and 0.3.
6) De koolwaterstoffractie die buteen-1, buteen-2 en isobuteen bevat, scheiden van de zware produkten.6) Separate the hydrocarbon fraction containing butene-1, butene-2 and isobutene from the heavy products.
7) De koolwaterstoffractie die buteen-1, buteen-2 25 en isobuteen bevat, en eventueel ook een gedeelte van de zware en verzadigde bestanddelen, toevoeren aan de zone voor de tert.butylalkylethersynthese, ofwel direkt, ofwel na vermenging met de C^-koolwaterstofstroom die vrij of vrijwel vrij is van butadieen. De (^-koolwaterstofvoeding 30 kan eveneens C^- en C^-bestanddelen bevatten. De C^-voeding bevat gewoonlijk koolwaterstoffen, isobutaan, isobuteen, buteen-1, n-butaan, trans-buteen-2, cis-buteen-2 en (^-koolwaterstoffen. De en koolwaterstoffen zijn in geringe hoeveelheden aanwezig, en de andere bestanddelen kunnen in 35 hoeveelheden aanwezig zijn die afhankelijk van de oorsprong sterk kunnen variëren.7) Feed the hydrocarbon fraction containing butene-1, butene-2 and isobutene, and optionally also some of the heavy and saturated components, to the tert-butyl alkyl ether synthesis zone, either directly or after mixing with the C 2 - hydrocarbon stream that is free or substantially free from butadiene. The ^-hydrocarbon feedstock 30 may also contain C 2 and C 2 ingredients. The C 2 feed usually contains hydrocarbons, isobutane, isobutene, butene-1, n-butane, trans-butene-2, cis-butene-2 and hydrocarbons. The and hydrocarbons are present in small amounts, and the other components may be present in amounts which can vary widely depending on the origin.
Om een constante molaire verhouding tussen buteen-1 8301819 I » .s -3- buteen-2 en isobuteen te verkrijgen wordt de isomerisatie van buteen-1 en/of buteen-2 uitgevoerd onder toepassing van een werkwijze zoals beschreven in het Italiaanse octrooi-schrift 1.017.878, met een katalysator op basis van silicium-5 houdend aluminiumoxyde, zoals beschreven in de Amerikaanse octrooischriften 4.013.589 en 4.013.590.To obtain a constant molar ratio between butene-1 8301819 I-s-3-butene-2 and isobutene, the isomerization of butene-1 and / or butene-2 is carried out using a process as described in the Italian patent No. 1,017,878, with a catalyst based on silicon-alumina, as described in U.S. Pat. Nos. 4,013,589 and 4,013,590.
Het is van belang op te merken dat de werkwijze volgens de onderhavige uitvinding het niet alleen mogelijk maakt om tert.butylalkylether te verkrijgen, doch eventueel 10 eveneens zuiver buteen-1 of anderzijds buteen-2, dat kan worden toegepast voor doeleinden die afwijken van de hierboven genoemde.It is important to note that the process of the present invention not only makes it possible to obtain tert-butyl alkyl ether, but optionally also pure butene-1 or other butene-2, which can be used for purposes other than the mentioned above.
De werkwijze volgens de onderhavige uitvinding is derhalve zeer veelzijdig, en gevonden is dat zelfs belang-15 rijke veranderingen in het isobuteengehalte van de voeding aan de synthesezone de uitvoeringsomstandigheden van deze synthese niet veranderen.The method of the present invention is therefore very versatile, and it has been found that even significant changes in the isobutene content of the feed to the synthesis zone do not change the operating conditions of this synthesis.
De werkwijze volgens de uitvinding wordt hierna op niet-beperkende wijze nader toegelicht aan de hand van 20 bijgaande tekening.The method according to the invention is further elucidated in a non-limiting manner with reference to the accompanying drawing.
In de tekening stelt (1) de C^-koolwaterstofvoeding voor die vrij of vrijwel vrij is van butadieen, (2) de uit de isomerisatiereactor (13) afkomstige stroom die buteen-1, buteen-2 en isobuteen, en een bepaalde hoeveelheid 25 verzadigde koolwaterstoffen bevat, (3) de totale stroom van (1) en (2), (4) de synthese-eenheid voor tert.butylmethyl-ether (MTBE), (5) de stroom MTBE, (6) de aan de synthesezone toegevoerde stroom methanol, (7) de C^-fractie die vrijwel vrij is van isobuteen, (19) een eventuele selectieve hydro-30 generingstrap voor de resterende butadieen en acetylenische verbindingen, (8) de aan de fractioneringstrap voor de verzadigde koolwaterstoffen en alkenen toegevoerde stroom, (9) de kolom voor het afscheiden van isobutaan (10), (11) de kolom voor het afscheiden van buteen-1 (12), en (13) de 35 kolom voor het scheiden van n-butaan (14) van cis- en trans-buteen-2 (15).In the drawing (1) represents the C 1 hydrocarbon feed which is free or substantially free of butadiene, (2) the stream from the isomerization reactor (13) containing butene-1, butene-2 and isobutylene, and a certain amount of saturated hydrocarbons, (3) the total flow of (1) and (2), (4) the tert-butyl methyl ether synthesis unit (MTBE), (5) the MTBE flow, (6) the synthesis zone. methanol stream supplied, (7) the C 1 fraction substantially free of isobutene, (19) an optional selective hydrogenation stage for the remaining butadiene and acetylenic compounds, (8) the fractionation stage for the saturated hydrocarbons and olefins. supplied stream, (9) the column for separating isobutane (10), (11) the column for separating butene-1 (12), and (13) the column for separating n-butane (14) of cis- and trans-butene-2 (15).
De buteen-1 stroom (12) kan worden toegevoerd aan 8301819 « · -4- het isomerisatiereactievat (16) via leiding (17), of kan met de gewenste zuiverheid worden afgevoerd via leiding (18). (20) stelt de waterstofstroom voor.The butene-1 stream (12) can be fed to the isomerization reaction vessel (16) through line (17), or it can be discharged with the desired purity through line (18). (20) represents the hydrogen flow.
Tabel A toont als niet-beperkend voorbeeld enkele 5 experimentele uitvoeringsomstandigheden tezamen met de resultaten die zijn verkregen volgens de werkwijze der uitvinding, onder verwijzing naar de figuur, en onder toepassing van de selectieve hydrogeneringseenheid (19) en de waterstof-stroom (20), doch zonder terugvoer van buteen-1 naar de iso-10 merisatie-zone.Table A shows as a non-limiting example some experimental operating conditions together with the results obtained according to the method of the invention, with reference to the figure, and using the selective hydrogenation unit (19) and the hydrogen flow (20), but without return of butene-1 to the iso-10 merization zone.
Tabel B toont als niet-beperkend voorbeeld enkele experimentele uitvoeringsomstandigheden en de resultaten die zijn verkregen volgens de werkwijze der uitvinding, eveneens onder verwijzing naar de tekening, doch zonder toepassing 15 van de selectieve hydrogeneringszone (19), doch met terugvoer van buteen-1 naar de isomerisatie zone.Table B shows as a non-limiting example some experimental operating conditions and the results obtained according to the method of the invention, also with reference to the drawing, but without using the selective hydrogenation zone (19), but with recycling of butene-1 to the isomerization zone.
8301819 I . § -5- _αοιιιιι»««· *-· 8 ______________________ I4 < οι « I I i I « · I · 88301819 I. § -5- _αοιιιιι »« «· * - · 8 ______________________ I4 <οι« I I i I «· I · 8
M CMM CM
X · .-- ,ë ~ rT ~cm 10 0 uj ______________________r* i * ' « .* 0 g 5* 8 « « _·*_____________~__S__ST____8 . h n n h n σ a, ·· · · · . jX · .--, ë ~ rT ~ cm 10 0 uj ______________________ r * i * '«. * 0 g 5 * 8« «_ · * _____________ ~ __S__ST ____ 8. h n n h n σ a, ·· · · ·. j
I I | Ο N IN·-·® I 9 X ' CM _ * « . OI I | IN N IN · - · ® I 9 X 'CM _ * «. O
N —---------— --— ~ — —.N —---------— --— ~ - -.
rtJc CM <0 new®,® <111 O I CO V 10 1 2rtJc CM <0 new®, ® <111 O I CO V 10 1 2
J?_____________^________NJ? _____________ ^ ________ N
cm c* ® n 0 Λ I · · · · ·cm c * ® n 0 Λ I · · · · ·
1 1 0 0 ® l 0 1 1 1 Q1 1 0 0 ® l 0 1 1 1 Q
X « 0 CM _ ____________X «0 CM _ ____________
k to er N CO *Mk to er N CO * M
< I I CM *e , CO I I I ÏJ<I I CM * e, CO I I I ÏJ
M re <0 I o JC CM f) rl · ·· ** ' " « • co 0 cm n re 0 a 0 0 Q, · · 1 · · ·#· ·M re <0 I o JC CM f) rl · ·· ** '"« • co 0 cm n re 0 a 0 0 Q, · 1 · · · # · ·
O 0®<”*0®IOre.r«| QO 0® <”* 0®IOre.r« | Q
•e X re N o ----“re----— — —--— —• e X re N o ---- “re ----— - —--— -
Jg<fea®00 « OT N . ®Jg <fea®00 «OT N. ®
SieBrtrto iocom I <*. os pi tn m ® < je___________co___________ _*· **“ re -" cm ^~<ό in co 0 tn re 0 uJ ······ · · · , · h aOrtrt0R‘,rtSrt,8 CQ X _ _ _____________ _j-e S*j 40 t. o co <r m co °S2 2 6·* j; ·η <0 o- *r w «o co o £> v cotOretnivNHl 0 be <o re m v cn x________-e___________<mSieBrtrto iocom I <*. os pi tn m ® <je___________co___________ _ * · ** “re -" cm ^ ~ <ό in co 0 tn re 0 uJ ······ · ·, · h aOrtrt0R ', rtSrt, 8 CQ X _ _ _____________ _j-e S * j 40 t.o co <rm co ° S2 2 6 · * j; · η <0 o- * rw «o co o £> v cotOretnivNHl 0 be <o re mv cn x ________-e ___________ < m
fflCMO» VcMN®©<M OfflCMO »VcMN® © <MO
• #····*··· * 0.|OrlN®OCMre®O Q no · h 0 pj j*___1___________________r* u OerrfON'COCU'iN to 3 (O^CM®reo»®«xt>· co 'N,|(<)®®rereCM®re · p• # ···· * ··· * 0. | OrlN®OCMre®OQ no · h 0 pj j * ___ 1 ___________________ r * u OerrfON'COCU'iN to 3 (O ^ CM®reo »®« xt> · co ' N, | (<) ®®rereCM®re · p
C4 N N re W N NC4 N N re W N N
X ____ H _^ ______________ _ NX ____ H _ ^ ______________ _ N
Ο» «ί ·» N N Μ Μ O OΟ »« ί · »N N Μ Μ O O
« ···· · · · · · a howot innMO 0 I CM re CM CM 0«···· · · · · · a howot innMO 0 I CM re CM CM 0
CM JX_____________._________ _J-CCM JX _____________._________ _J-C
u Λ ο ο m u β η β m re «^|N*rO®l&®CM'N © M re CON CM CM re p a cm re cm cm__ a ® to w m to n ® to ® Λ ·«······ Λu Λ ο ο mu β η β m re «^ | N * rO®l & ®CM'N © M re CON CM CM re pa cm re cm cm__ a ® to wm to n ® to ® Λ ·« ···· ·· Λ
iOre-ooowa®i XiOre-ooowa®i X
X 0 O’ re re — - ·X 0 O're re - - ·
C, (M'JOO'Om^® CMC, (M'JOO'Om ^ ® CM
jg CROCMNreONre. Qjg CROCMNreONre. Q
^*|re«®MreO<MOI O^ * | re «®MreO <MOI O
t* n m re co cm a X______rC__r*____________ n ” —— ——t * n m re co cm a X ______ rC__r * ____________ n ”—— ——
CNCN
1 β I I1 β I I
Je 0) β CN kYou 0) β CN k
a) a> (D I <Ua) a> (D I <U
4-) β ·Η <D β 4-1 β (d <D β β Ό 4J <1) <d Φ 2 n-e td ajr-e re β β <u r-eiH® <y I 4-) (0 JÜ 4J ·-· ^4-) β · Η <D β 4-1 β (d <D β β Ό 4J <1) <d Φ 2 ne td ajr-e re β β <u r-eiH® <y I 4-) (0 JÜ 4J - - ^
cn 004J4JfiSfCI D00r-Icn 004J4JfiSfCI D00r-I
4J 04J33<UX»4-)WX!04-)« cd ^ cn Xi λ ω ) β c l a: « (04J 04J33 <UX »4-) WX! 04-)« cd ^ cn Xi λ ω) β c l a: «(0
cd 0044ΠΛβΜ 4Jcd 0044ΠΛβΜ 4J
r-e (Nnww3*.|le-Hin Or-e (Nnww3 *. | le-Hin O
CU BO-H-HXir-ifi4-)üO Eh 8301819 -6- η * « m n <η to ο ο cv «···· « · _ » ο ο μ «η r» f* ( ο , X <Γ CM CM Ο r* .. ___ _ «Η fa otftrHootn r>CU BO-H-HXir-ifi4-) üO Eh 8301819 -6- η * «mn <η to ο ο cv« ···· «· _» ο ο μ «η r» f * (ο, X <Γ CM CM Ο r * .. ___ _ «Η fa otftrHootn r>
Λ r-tcocoioocni CM-R-tcocoioocni CM
I t-« «H (O SI O N ' CMI t- «« H (O SI O N 'CM
03 U» o Ö> Ό03 U »o Ö> Ό
JÉ r-4 r-( COJÉ r-4 r- (CO
• ° N 5 § · 8 3 -—--0• ° N 5 §8 8 -—-- 0
fa ID o O to Ofa ID o O to O
jC <-l O O Or» »-fjC <-l O O Or »» -f
S I I I Μ O Γ*· I CMS I I I Μ O Γ * · I CM
o» O <n Oo »O <n O
JC_ _____^ _ CMJC_ _____ ^ _ CM
• . H CO (O f» O•. H CO (O f »O
O. I I' · · · · H · O 0» O CO · . . o X H CO V CO I oO. I I '· · · · H · O 0 »O CO ·. . o X H CO V CO I o
Ί HΊ H
H — .................-................- ..... «».H - .................-................- ..... «».
fafa
Λ 'T COCO 'T CO
"N I I 00 et N CO (V"N I I 00 and N CO (V
09 CM ·-* t-i rt Ό09 CM · - * t-i rt Ό
JÉ t- rH l- Π I COJÉ t- rH l- Π I CO
«-<·-» ··«- <· -» ··
• C» CM CO CO · O• C »CM CO CO · O
o> · · · · ·o> · · · · ·
IOHNO I I I OIOHNO I I I O
*> *_- °» 2 ti co io co co t>.*> * _- ° »2 ti co io co co t>.
•C . »-C CO CO IO ι-t -t• C. -C CO CO IO ι-t -t
I Π Η CO III OI Π Η CO III O
(4 to co(4 to co
Jé Η HJé Η H
• p-ot^r-ctMcncM o O.·······! · .. «o.HOtr«-c<ocM o _ X H rl U o s-----n JSOCOCOCMCOr^CO m 'NIOffiCOCOtoKrHI O»• p-ot ^ r-ctMcncM o O. ········! · .. «o.HOtr« -c <ocM o _ X H rl U o s ----- n JSOCOCOCMCOr ^ CO m 'NIOffiCOCOtoKrHI O »
68 «0 U> CM «-C t-i O68 «0 U> CM« -C t-i O
Jé co inJé co in
• Ol 4 Ifl N (O m n O• Ol 4 Ifl N (O m n O
cv······· · •H rC O.,(O CO (O CM I ocv ········ · • H rC O., (O CO (O CM I o
• X vr CM CM O• X for CM CM O
CO ______________HCO ______________H
oJjr^rtt^^fto co •CCOOCMCoCMCACM Ol m'S.CONCMIOIOCOO I ooJjr ^ rtt ^^ fto co • CCOOCMCoCMCACM Ol m'S.CONCMIOIOCOO I o
te 9t >H rM O Vat 9t> H rM O V
JÉ r-t ι-t ri «ü jj I- - W •(Oi-CCOlOV'iOM · CQ o,········ oJÉ r-t ι-t ri «ü yy I- - W • (Oi-CCOlOV'iOM · CQ o, ········· o
f£ .. *-CHCMe»CMf.inO Of £ .. * -CHCMe »CMf.inO O
g „ *-2-Si--_2__Λ fa.o r-ι ^ o r·. m co o n JSinO-CMC^CMCOCMCn c^ 'VCOC-OCOCOCOOCM o 63 CM Λ n «H O C*g „* -2-Si --_ 2__Λ fa.o r-ι ^ o r ·. m co o n JSinO-CMC ^ CMCOCMCn c ^ 'VCOC-OCOCOCOOCM o 63 CM «n« H O C *
JÉ CM · i-C_r-t -) (OJÉ CM · i-C_r-t -) (O
• ocomcocMcooco o (X* ···*·«· · ^.MOtnmcM iocoo o• ocomcocMcooco o (X * ··· * · «· · ^ .MOtnmcM iocoo o
X CM H CM CM OX CM H CM CM O
fa ~......" .coOicO'Tirti-cino «o ^.ajr'CMotajcOioo* mfa ~ ...... ".coOicO'Tirti-cino« o ^ .ajr'CMotajcOioo * m
68.C0CMOO>t'O)COCM CO68.C0CMOO> t'O) COCM CO
JÉ 0) lO CQ 09 m _______________________________ coJÉ 0) 10 CQ 09 m _______________________________ co
•UVCOOxOf«IOCO O• UVCOOxOf «IOCO O
CV······· ·RESUME······· ·
O*‘«r4.OCMC0'ft | OO * "« r4.OCMC0'ft | O
X «f «Τ' oX «f« Τ 'o
H ----------- --- “ \HH ----------- --- “\ H
fa^CMcoincM'Vca ·-«fa ^ CMcoincM'Vca · - «
jC«OMC>f-*^<0 COjC «OMC> f - * ^ <0 CO
'Vrt'MOIeJCOf'COl N'Vrt'MOIeJCOf'COl N
68 CM CM CM -* -c _JÉ ._.-» r-4_ <068 CM CM CM - * -c _JÉ ._.- »r-4_ <0
CMCM
I 1 II 1 I
M G CM MM G CM M
<D (1) I <D<D (1) I <D
PC <1) G P GPC <1) G P G
flJfDGG P <D G <1> 5 P G Q) t-i G G <D ΪΉflJfDGG P <D G <1> 5 P G Q) t-i G G <D ΪΉ
r^CWCd <U I <d Λ +Jr ^ CWCd <U I <d Λ + J
W004J4JGCÖI G00 Γ-» +J 0 4J G G Q) -P W Λ 0-P «1W004J4JGCÖI G00 Γ- »+ J 0 4J G G Q) -P W Λ 0-P« 1
GJidWJ3iaaJGGI^!W GGJidWJ3iaaJGGI ^! W G
(0 OO+JOGW -P(0 OO + JOGW -P
rHncQWGIP'Hin OrHncQWGIP'Hin O
Oiü-H-H^GPOUOiü-H-H ^ GPOU
l 83018191 8301819
Claims (4)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2138482 | 1982-05-20 | ||
| 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 |
|---|---|
| NL8301819A true NL8301819A (en) | 1983-12-16 |
Family
ID=11180967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8301819A NL8301819A (en) | 1982-05-20 | 1983-05-20 | PROCESS FOR PREPARING TERT BUTYL ALKYL 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 AU AU14017/83A patent/AU1401783A/en not_active Abandoned
- 1983-04-28 GR GR71241A patent/GR78857B/el unknown
- 1983-04-28 NZ NZ204032A patent/NZ204032A/en unknown
- 1983-04-29 ZA ZA833068A patent/ZA833068B/en unknown
- 1983-04-29 ZW ZW97/83A patent/ZW9783A1/en unknown
- 1983-05-05 SE SE8302577A patent/SE8302577L/en not_active Application Discontinuation
- 1983-05-05 CH CH2465/83A patent/CH653664A5/en not_active IP Right Cessation
- 1983-05-06 BR BR8302433A patent/BR8302433A/en unknown
- 1983-05-12 GB GB08313098A patent/GB2121407B/en not_active Expired
- 1983-05-13 MW MW18/83A patent/MW1883A1/en unknown
- 1983-05-13 LU LU84805A patent/LU84805A1/en unknown
- 1983-05-13 KR KR1019830002066A patent/KR860001854B1/en not_active Expired
- 1983-05-17 YU YU01100/83A patent/YU110083A/en unknown
- 1983-05-17 FR FR8308163A patent/FR2527202B1/en not_active Expired
- 1983-05-18 NO NO831759A patent/NO831759L/en unknown
- 1983-05-18 DK DK221683A patent/DK221683A/en not_active Application Discontinuation
- 1983-05-18 BG BG061013A patent/BG37678A3/en unknown
- 1983-05-18 PH PH28926A patent/PH19481A/en unknown
- 1983-05-18 TR TR21617A patent/TR21617A/en unknown
- 1983-05-19 PT PT76730A patent/PT76730B/en unknown
- 1983-05-19 DD DD83251077A patent/DD209803A5/en unknown
- 1983-05-19 BE BE0/210806A patent/BE896787A/en not_active IP Right Cessation
- 1983-05-19 CA CA000428516A patent/CA1220230A/en not_active Expired
- 1983-05-19 DE DE19833318301 patent/DE3318301A1/en not_active Withdrawn
- 1983-05-20 ES ES523006A patent/ES523006A0/en active Granted
- 1983-05-20 IN IN632/CAL/83A patent/IN159788B/en unknown
- 1983-05-20 PL PL24209383A patent/PL242093A1/en unknown
- 1983-05-20 NL NL8301819A patent/NL8301819A/en not_active Application Discontinuation
- 1983-05-20 JP JP58087816A patent/JPS58210039A/en active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4513153A (en) | Integrated process for producing tert.butyl alkyl ethers and butene-1 | |
| US4423251A (en) | Process employing sequential isobutylene hydration and etherification | |
| KR102371934B1 (en) | Dehydrogenation of lpg or ngl and flexible utilization of the olefins thus obtained | |
| US5382707A (en) | Integrated MTBE process | |
| EP0667329A1 (en) | Integrated process for the simultaneous production of alkyl tert-butyl ethers and 1-butene | |
| MX2012000240A (en) | Producing isobutene by cracking mtbe. | |
| NL8002334A (en) | PROCESS FOR THE PREPARATION OF METHYL-TERT-BUTYL ETHER FROM MATHANOL AND ISOBUTENE. | |
| CZ20013640A3 (en) | Process for preparing extremely pure raffinate II and methyl-tert-butyl ether | |
| JP3854650B2 (en) | Olefin metathesis | |
| CS242853B2 (en) | Method of methyl-tertiary butyl ether preparation | |
| RU2722665C1 (en) | Removal of paraffin from streams containing c4 | |
| NL8301819A (en) | PROCESS FOR PREPARING TERT BUTYL ALKYL ETHERS. | |
| EP0042252B1 (en) | Isobutene by dehydroisomerisation of normal butane | |
| US5132467A (en) | Process for the conversion of normal alkenes to tertiary alkyl ethers | |
| AU635640B2 (en) | Production of ether from alcohol and isoolefin in the presence of h2o with h2o/alcohol recycle | |
| KR920006264A (en) | Simultaneous Hydrogenation / Dehydrogenation Reactions in a Single Reaction Zone | |
| US5108719A (en) | Reactor system for ether production | |
| US4988366A (en) | High conversion TAME and MTBE production process | |
| WO2003031539A1 (en) | An oxygenated gasoline component and a method of producing thereof | |
| CN1237044C (en) | Process for producing C4-acetate | |
| JPH0352826A (en) | Preparation of pure c4-c7-tertiary alkene | |
| US11845707B2 (en) | Processes and systems for C3+ monoolefin conversion | |
| GB1589457A (en) | Method for purifying methyl tert butyl ether | |
| KR20180047941A (en) | Polyisobutene feed pretreatment method | |
| EP4387945A1 (en) | Metathesis of c4/c5 to propylene and 1-hexene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |