CA1220230A - Process for producing tert.butyl alkyl ethers - Google Patents
Process for producing tert.butyl alkyl ethersInfo
- Publication number
- CA1220230A CA1220230A CA000428516A CA428516A CA1220230A CA 1220230 A CA1220230 A CA 1220230A CA 000428516 A CA000428516 A CA 000428516A CA 428516 A CA428516 A CA 428516A CA 1220230 A CA1220230 A CA 1220230A
- Authority
- CA
- Canada
- Prior art keywords
- butene
- tert
- hydrocarbon
- isobutene
- butyl alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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
ABSTRACT OF THE DISCLOSURE:
The process for synthesising tert.butyl alkyl ethers is combined with a process for isomerising butene-1 and/or butene-2 in order to increase the ether yield, the butene-1 and/or butene-2 being separated from the C4 satu-rated hydrocarbons after formation of the tert.butyl alkyl ether and its separation from the residual C4 stream.
The process for synthesising tert.butyl alkyl ethers is combined with a process for isomerising butene-1 and/or butene-2 in order to increase the ether yield, the butene-1 and/or butene-2 being separated from the C4 satu-rated hydrocarbons after formation of the tert.butyl alkyl ether and its separation from the residual C4 stream.
Description
31~
This invention relates to a process for producing tert.butyl alkyl ethers.
More particularly, the present invention relates to a process for producing tert.butyl methyl ether.
Many processes are known in the art for producing tert.butyl alkyl ethers, consisting of reacting isobutene, contained in hydrocarbon streams of various origin and in particular in the stream originating from steam cracking, catalytic cracking or dehydrogenation of isobutane, with an alcohol, preferably methanol or ethanol, in the presence of an acid ion exchange resin.
In this respect, reference can be made to Italian patents 1,012,686, 1,012,587 and 1,012,690.
The known processes allow an almost total iso-butene conversion, but the other components remain practi-cally unchanged, and cannot therefore be used as such directly as petrol components.
The process according to the present invention allows the conversion of part of the components of the hydrocarbon feedstock with 4 carbon atoms, other than iso-butene, into tert.butyl alkyl ethers, together with the isobutene originally con-tained in said feedstock.
The present invention provides a process for producing tert.butyl alkyl ethers from a C4 hydrocarbon feed-stock possibly also containing C3 and C5 components from which the butadiene has previously been separated, consisting of feeding the C4 hydrocarbon feedstock free or substantially free of bu-tadiene to a tert.butyl alkyl ether synthesis sec-tion containing a catalyst constituted by an acid ion exchange resin, preferably of the sulphonated divinylbenzene-styrene type, reac-ting the isobutene contained in the C4 hydrocarbon feedstock with an aliphatic alcohol in order to : , 3~D
produce a tert.butyl alkyl ether, and separating the tert.-butyl alkyl e-ther from the residual C~ hydrocarbons, charac-terised in that the residual C4 hydrocarbons are subjected to fractionation in two or three stages in order to separate the saturated hydrocarbons from the butene-1 and butene-2, and the butene-l and/or butene-2 are fed to an isomerisation stage where they are partly converted into isobutene to obtain a hydrocarbon frac-tion containing essentially butene-l, butene-2 and isobutene together with heavy products, the hydrocarbon fraction containing essentially butene-l, butene-2 and isobutene and possibly part of the heavy and saturated components being fed to the tert.butyl alkyl ether synthesis reaction.
In particular a process according to the present invention may consist of the following stages:
1) Feeding the C4 hydrocarbon feedstock, either free or substantially free of butadiene, to a tert.butyl alkyl ether synthesis section, said section containing a catalyst constituted by an acid ion exchange resin, preferably of the sulphonated divinylbenzene-styrene type.
This invention relates to a process for producing tert.butyl alkyl ethers.
More particularly, the present invention relates to a process for producing tert.butyl methyl ether.
Many processes are known in the art for producing tert.butyl alkyl ethers, consisting of reacting isobutene, contained in hydrocarbon streams of various origin and in particular in the stream originating from steam cracking, catalytic cracking or dehydrogenation of isobutane, with an alcohol, preferably methanol or ethanol, in the presence of an acid ion exchange resin.
In this respect, reference can be made to Italian patents 1,012,686, 1,012,587 and 1,012,690.
The known processes allow an almost total iso-butene conversion, but the other components remain practi-cally unchanged, and cannot therefore be used as such directly as petrol components.
The process according to the present invention allows the conversion of part of the components of the hydrocarbon feedstock with 4 carbon atoms, other than iso-butene, into tert.butyl alkyl ethers, together with the isobutene originally con-tained in said feedstock.
The present invention provides a process for producing tert.butyl alkyl ethers from a C4 hydrocarbon feed-stock possibly also containing C3 and C5 components from which the butadiene has previously been separated, consisting of feeding the C4 hydrocarbon feedstock free or substantially free of bu-tadiene to a tert.butyl alkyl ether synthesis sec-tion containing a catalyst constituted by an acid ion exchange resin, preferably of the sulphonated divinylbenzene-styrene type, reac-ting the isobutene contained in the C4 hydrocarbon feedstock with an aliphatic alcohol in order to : , 3~D
produce a tert.butyl alkyl ether, and separating the tert.-butyl alkyl e-ther from the residual C~ hydrocarbons, charac-terised in that the residual C4 hydrocarbons are subjected to fractionation in two or three stages in order to separate the saturated hydrocarbons from the butene-1 and butene-2, and the butene-l and/or butene-2 are fed to an isomerisation stage where they are partly converted into isobutene to obtain a hydrocarbon frac-tion containing essentially butene-l, butene-2 and isobutene together with heavy products, the hydrocarbon fraction containing essentially butene-l, butene-2 and isobutene and possibly part of the heavy and saturated components being fed to the tert.butyl alkyl ether synthesis reaction.
In particular a process according to the present invention may consist of the following stages:
1) Feeding the C4 hydrocarbon feedstock, either free or substantially free of butadiene, to a tert.butyl alkyl ether synthesis section, said section containing a catalyst constituted by an acid ion exchange resin, preferably of the sulphonated divinylbenzene-styrene type.
2) Reacting the isobutene con-tained in the C4 hydro-c ..
- 2 ~ 23~
of point l) with an aliphatic alcohol fed to said synthesis section, the molar ratio of the alcohol to the isobutene be-ing between 0.9 and 1.3, the reaction product being a tert.
butyl alkyl ether.
- 2 ~ 23~
of point l) with an aliphatic alcohol fed to said synthesis section, the molar ratio of the alcohol to the isobutene be-ing between 0.9 and 1.3, the reaction product being a tert.
butyl alkyl ether.
3) Separating the tert.bu-tyl alkyl ether from -the C4 hydrocarbons by distillation either in the same reaction zone or in a separate zone.
4) Fractionation of the residual C4 hydrocarbon feed in two or three stages at a temperature of between 40 C
and 130C and a pressure of between 4 ata and 26 ata, using between 100 and 220 plates to separate the sa-turated hydro-carbons (butane and isobutane) from the butene-l and butene-2.
and 130C and a pressure of between 4 ata and 26 ata, using between 100 and 220 plates to separate the sa-turated hydro-carbons (butane and isobutane) from the butene-l and butene-2.
5) Feeding the butene-l and/or butene-2 and the unse-parated saturated components of s-tage 4) to an isomerisation lS stage in which the butene~l and/or butene-2 are partly con-verted into isobutene, to obtain, whatever the starting olefin or the starting mixture, a hydrocarbon fraction containing essentially butene-l, butene-2 and isobutene in which the butene-l/butene-2 molar ratio corresponds practically to thermodynamic equilibrium, whereas the isobutene/linear bu-tene molar ratio lies between 0.6 and 0.3.
6) Separating the hydrocarbon fraction containing butene-l, butene-2 and isobutene from the heavy products.
7) Feeding the hydrocarbon fraction containing butene-l, butene-2 and isobutene, and possibly also part of the heavy and saturated components, to the tert.butyl alkyl ether syn-thesis section, either directly or after mixing with the C4 hydrocarbon stream which is free or substantially free of butadiene. The C4 hydrocarbon feedstock possibly also contains C3 and C5 components.
The C4 feedstock normally comprises C3 hydrocarbons, isobutane, isobutene, butene-l, n-butane, trans butene-2, cis butene-2,and C5 hydrocarbons. The C3 and C5 hydrocarbons are in small quantities, and the others can be in relative f~ ~2~3~
quantities which vary greatly according to its origin.
In order to obtain a constant molar ratio between butene-1, butene-2 and isobutene, isomerisation of the butene-1 and/or butene-2 is carried out using a process such as that described in Italian patent 1,017,878,with a catalyst based on silicised alumina such as that described in USA
patents 4,013,589 and 4,013,590.
It is interesting to note that the process accord-ing to the present invention enables not only the tert.butyl alkyl ether to be obtained, but possibly also pure butene-1 or alternatively butene-2, which can be used for purposes other than those mentioned herein.
The process according to the present inven-tion is therefore very versatile, and it has been found tha-t even significant variations in the isobutene content of the stream fed to the synthesis section do not change the operating conditions of said synthesis.
The process according to the present invention is illustrated hereinafter in a non-limiting manner with refer-ence to the scheme of the accompanying figure.
In it, (1) indicates the C4 hydrocarbon feedstockfree or substantially free of butadiene, (2) the stream from the isomerisation reactor (13) comprising butene-1, butene-2 and isobutene, and a certain quantity of saturated hydrocar-bons, (3) the total stream of (1) and (2), (4) the synthesisunit for the tert.butyl methyl ether (MTBE), (5) -the MTB~
stream, (6) the methanol stream fed to -the synthesis section, (7) the C4 fraction substantially free of isobutene, (19) a possible selective hydrogenation stage for the residual buta-diene and any acetylenic compounds, (8) the feed stream tothe fractionation section for the saturated hydrocarbons and olefins, (9) the column for separating -the isobutane (10), (11) the column for separating the butene-1 (12), and (13) the column for separating the n-butane (14) from -the cis and trans butene-2 (15).
The butene-1 stream (12) can be fed to the isomeri-sation reactor (16) through the line (17), or can be dis-charged at -the required purity through the llne (18). (20) represents the hydrogen stream.
Table 1 illustrates by way o~ non-limiting example some experimental operating conditions together with the relative resul-ts obtained by the process according to the invention, with reference to Figure using the selective hy-drogenation unit (19) and the hydrogen stream (20), butwithout recycling the butene-1 to the isomerisation zone.
5 ~L~?o tcttt ~2 ~) o t'` oO ~ I ~ I 7 ~ Q' N t __ __ _ __, _ _ __ _ _ __ _,_ _~ _ _ __ _ _ _ ~ N
._ _ _ _ __ _ _ _ _.._ __ _ _ _ _ _ _ __ _ _ _ _ _ L~ O I t,~t m N I O
ID - Irl r,r O
r~ -- -- -- -- -- ----- --_ --_ _ __ _ _ _ _ _ __ _ _ _ ._ l l l C~ t l _ o t`. r~t ~ N
Y tU r~ a~- lu _____________ ____ :r ~rt a~
r t C~t cr t~ 1~ V
C~ I I ; o ;r I r~ ~t tO I O
~- _ _ _ _ _ __ _ _ _ _ __ _ __ _ _ _._ _ _ _ __ __ _._ r1 . ~ t~t ~ It',t ~ t ~qO~
~ Nrt <O cr,t ~1 S I I ~ ~ r tr~ n _ _ _ _ _ _ _ ._ _ _ __ __ __ ~_ __ __ _ __ _ _ _ Ir,t O C~ a tJt O O
o o 0~l o ta I o r I . r l I O
_ _ _ __ _ ------ rt tLl rD <r~ trt tXt O I tXt t n I L'Ct t-.~ _Y trt r~r <~ r tt.~l L~t ~t ~rt o tD rl O
~t O rt rl Otrt~ rt r I I rl Lrt I --~ ~ r~ 0 ~;t tO L-t ~ ~r trt ~t~ C~) tr,t , t U r~ CCt O O
t,r~ ________ I ___________,________ _ ; L tD trt rt ~ tr~ tCt r ~ r crt ~ q t~ N N .~ L'Ct O
- N `~t' I ~; tn a~ ~ tu tD trt co --'--_ _ _ _ _N t~ tO
rt _ _ _ _ __ _ _ _ _ ~ I V
D Ct o N tr,t t r t ~rt N I ¦ O
. _.. . . ., .. _ . . . .. __._. __.. , ._.. __.__ _ t7t t t I t ,t t,l~
C h S-d~ ~ t i ~_t ~:: ct J t h I rti t ~Lt ~ ~ 3 ~p L~t .~ ~t r ~ l~t ~j ~t ,t~ ~ t`- 1 t~,t O ~t o t,~J C~) Lq t q ~ I L~ r~ U~t O
Table 2 illus~r~es by ~ay of non-limi~ing exa~ple some experii~e operati.ng condit;.ons and th~ results obtained by ~he process accordin~
to the invention, again ~ith reference to Fi~ure ~ ithout usin~
~he selective hyclrogenation ~one (19) bu~ ~ecycling th2 butene 1 '~o the isc,meriset:ion ~oneD
_ 7............ 3~
. ~ u> ~ o o ~ i O O tr~ r I t~ t~ I O
c~ . ___ L t~> L') r~ )O U ) i~
r~ CC C1 ) ~ Ot~ ~ c ~ r1 C~
_~ O
' ' .1 . o cuc~ t~ o U~ _~
. L U) O O U~ O
S I I I r l0~ 0 ~ I
R, I ~.'-I 0 cf~ ~ ,., O
O O 0 0~ C~O ~; I . . r~
L . ~ ~`'~ ~`~~ __ X C'~ t~ L') U~
~ l _ CO C~ . O
~ I ~ O .1 t O I I I Q
~, C') U) C~ C'~ t`
S . I ~ r lU~ I O .
X LD r l t` D t` r l NU i N O
~e r I r I ~Jr; C~ N r l r~
~` i C O ~ 0 NC" t` ~ .:
r~ LO CC C~ ) ~ t~ rl I -~_. a~
~;~ _ ~ Ir 1 O
~ ~ a~ u~ u~ t~ c~) O ~
E-l 0 ~ o co t~ c3 ~CD CC O J 0~
.~D a~ I O ~J
.__ ! cOcO ~ ~o ~ O
~1 r; N CrC~J t~ U~ O ~1 . ~UO~ O 1~1 t~.~` ~ N 0 1~ . oc~ o N
X N . r ~ r-l t~
. _. _ _ _ ' . OCO ~ CO ' C~i cr~I~> co O
c~ cu o u; a;~ u; ~ o o N ' C~ ~ N _ s a~ o) c cncc u~ U a~ ~
. . x .. '`J O cn t~ O~ c C~J ~
. u) c~) o ~t~ a) ~ o , ~ O~< r , O N CD11') I O
~ -- ___ ~
L _ N C )(C~ N ~ CC r~
~ ~ ~ CC~C0 0t~i ~O I t~
C r lr~ C~) _ __ m u~
~1 c i a) Cl) rd cV ~) ~ t~ ~
r~ CV O
O ~ rd C
~ ~ 3 ~ G~
Co Q O ~L~ n U~
~, c,~ .rl.r~ ~ ~ ~ V ~ E~
The C4 feedstock normally comprises C3 hydrocarbons, isobutane, isobutene, butene-l, n-butane, trans butene-2, cis butene-2,and C5 hydrocarbons. The C3 and C5 hydrocarbons are in small quantities, and the others can be in relative f~ ~2~3~
quantities which vary greatly according to its origin.
In order to obtain a constant molar ratio between butene-1, butene-2 and isobutene, isomerisation of the butene-1 and/or butene-2 is carried out using a process such as that described in Italian patent 1,017,878,with a catalyst based on silicised alumina such as that described in USA
patents 4,013,589 and 4,013,590.
It is interesting to note that the process accord-ing to the present invention enables not only the tert.butyl alkyl ether to be obtained, but possibly also pure butene-1 or alternatively butene-2, which can be used for purposes other than those mentioned herein.
The process according to the present inven-tion is therefore very versatile, and it has been found tha-t even significant variations in the isobutene content of the stream fed to the synthesis section do not change the operating conditions of said synthesis.
The process according to the present invention is illustrated hereinafter in a non-limiting manner with refer-ence to the scheme of the accompanying figure.
In it, (1) indicates the C4 hydrocarbon feedstockfree or substantially free of butadiene, (2) the stream from the isomerisation reactor (13) comprising butene-1, butene-2 and isobutene, and a certain quantity of saturated hydrocar-bons, (3) the total stream of (1) and (2), (4) the synthesisunit for the tert.butyl methyl ether (MTBE), (5) -the MTB~
stream, (6) the methanol stream fed to -the synthesis section, (7) the C4 fraction substantially free of isobutene, (19) a possible selective hydrogenation stage for the residual buta-diene and any acetylenic compounds, (8) the feed stream tothe fractionation section for the saturated hydrocarbons and olefins, (9) the column for separating -the isobutane (10), (11) the column for separating the butene-1 (12), and (13) the column for separating the n-butane (14) from -the cis and trans butene-2 (15).
The butene-1 stream (12) can be fed to the isomeri-sation reactor (16) through the line (17), or can be dis-charged at -the required purity through the llne (18). (20) represents the hydrogen stream.
Table 1 illustrates by way o~ non-limiting example some experimental operating conditions together with the relative resul-ts obtained by the process according to the invention, with reference to Figure using the selective hy-drogenation unit (19) and the hydrogen stream (20), butwithout recycling the butene-1 to the isomerisation zone.
5 ~L~?o tcttt ~2 ~) o t'` oO ~ I ~ I 7 ~ Q' N t __ __ _ __, _ _ __ _ _ __ _,_ _~ _ _ __ _ _ _ ~ N
._ _ _ _ __ _ _ _ _.._ __ _ _ _ _ _ _ __ _ _ _ _ _ L~ O I t,~t m N I O
ID - Irl r,r O
r~ -- -- -- -- -- ----- --_ --_ _ __ _ _ _ _ _ __ _ _ _ ._ l l l C~ t l _ o t`. r~t ~ N
Y tU r~ a~- lu _____________ ____ :r ~rt a~
r t C~t cr t~ 1~ V
C~ I I ; o ;r I r~ ~t tO I O
~- _ _ _ _ _ __ _ _ _ _ __ _ __ _ _ _._ _ _ _ __ __ _._ r1 . ~ t~t ~ It',t ~ t ~qO~
~ Nrt <O cr,t ~1 S I I ~ ~ r tr~ n _ _ _ _ _ _ _ ._ _ _ __ __ __ ~_ __ __ _ __ _ _ _ Ir,t O C~ a tJt O O
o o 0~l o ta I o r I . r l I O
_ _ _ __ _ ------ rt tLl rD <r~ trt tXt O I tXt t n I L'Ct t-.~ _Y trt r~r <~ r tt.~l L~t ~t ~rt o tD rl O
~t O rt rl Otrt~ rt r I I rl Lrt I --~ ~ r~ 0 ~;t tO L-t ~ ~r trt ~t~ C~) tr,t , t U r~ CCt O O
t,r~ ________ I ___________,________ _ ; L tD trt rt ~ tr~ tCt r ~ r crt ~ q t~ N N .~ L'Ct O
- N `~t' I ~; tn a~ ~ tu tD trt co --'--_ _ _ _ _N t~ tO
rt _ _ _ _ __ _ _ _ _ ~ I V
D Ct o N tr,t t r t ~rt N I ¦ O
. _.. . . ., .. _ . . . .. __._. __.. , ._.. __.__ _ t7t t t I t ,t t,l~
C h S-d~ ~ t i ~_t ~:: ct J t h I rti t ~Lt ~ ~ 3 ~p L~t .~ ~t r ~ l~t ~j ~t ,t~ ~ t`- 1 t~,t O ~t o t,~J C~) Lq t q ~ I L~ r~ U~t O
Table 2 illus~r~es by ~ay of non-limi~ing exa~ple some experii~e operati.ng condit;.ons and th~ results obtained by ~he process accordin~
to the invention, again ~ith reference to Fi~ure ~ ithout usin~
~he selective hyclrogenation ~one (19) bu~ ~ecycling th2 butene 1 '~o the isc,meriset:ion ~oneD
_ 7............ 3~
. ~ u> ~ o o ~ i O O tr~ r I t~ t~ I O
c~ . ___ L t~> L') r~ )O U ) i~
r~ CC C1 ) ~ Ot~ ~ c ~ r1 C~
_~ O
' ' .1 . o cuc~ t~ o U~ _~
. L U) O O U~ O
S I I I r l0~ 0 ~ I
R, I ~.'-I 0 cf~ ~ ,., O
O O 0 0~ C~O ~; I . . r~
L . ~ ~`'~ ~`~~ __ X C'~ t~ L') U~
~ l _ CO C~ . O
~ I ~ O .1 t O I I I Q
~, C') U) C~ C'~ t`
S . I ~ r lU~ I O .
X LD r l t` D t` r l NU i N O
~e r I r I ~Jr; C~ N r l r~
~` i C O ~ 0 NC" t` ~ .:
r~ LO CC C~ ) ~ t~ rl I -~_. a~
~;~ _ ~ Ir 1 O
~ ~ a~ u~ u~ t~ c~) O ~
E-l 0 ~ o co t~ c3 ~CD CC O J 0~
.~D a~ I O ~J
.__ ! cOcO ~ ~o ~ O
~1 r; N CrC~J t~ U~ O ~1 . ~UO~ O 1~1 t~.~` ~ N 0 1~ . oc~ o N
X N . r ~ r-l t~
. _. _ _ _ ' . OCO ~ CO ' C~i cr~I~> co O
c~ cu o u; a;~ u; ~ o o N ' C~ ~ N _ s a~ o) c cncc u~ U a~ ~
. . x .. '`J O cn t~ O~ c C~J ~
. u) c~) o ~t~ a) ~ o , ~ O~< r , O N CD11') I O
~ -- ___ ~
L _ N C )(C~ N ~ CC r~
~ ~ ~ CC~C0 0t~i ~O I t~
C r lr~ C~) _ __ m u~
~1 c i a) Cl) rd cV ~) ~ t~ ~
r~ CV O
O ~ rd C
~ ~ 3 ~ G~
Co Q O ~L~ n U~
~, c,~ .rl.r~ ~ ~ ~ V ~ E~
Claims (8)
1. A process for producing tert.butyl alkyl ethers from a C4 hydrocarbon feedstock possibly also containing C3 and C5 components from which the butadiene has previously been separated, consisting of feeding the C4 hydrocarbon feedstock free or substantially free of butadiene to a tert.-butyl alkyl ether synthesis section containing a catalyst constituted by an acid ion exchange resin reacting the iso-butene contained in the C4 hydrocarbon feedstock with an aliphatic alcohol in order to produce a tert.butyl alkyl ether, and separating the tert.butyl alkyl ether from the residual C4 hydrocarbons, characterised in that the residual C4 hydrocarbons are subjected to fractionation in two or three stages in order to separate the saturated hydrocarbons from the butene-1 and butene-2, and the butene-1 and/or butene-2 are fed to an isomerisation stage where they are partly converted into isobutene to obtain a hydrocarbon frac-tion containing essentially butene-1, butene-2 and isobutene together with heavy products, the hydrocarbon fraction containing essentially butene-1, butene-2 and isobutene and possibly part of the heavy and saturated components being fed to the tert.butyl alkyl ether synthesis reaction.
2. A process as defined in claim 1, wherein the butene-1, butene-2 and isobutene are present in the hydro-carbon fraction obtained from the isomerisation stage in such proportions that the butene-1/butene-2 molar ratio corresponds to thermodynamic equilibrium, whereas the iso-butene/linear butene molar ratio lies between 0.6 and 0.3.
3. A process as defined in claim 1, wherein the hydrocarbon fraction obtained from the butene-1 and/or butene-2 isomerisation stage is fed to the synthesis section after mixing with the C4 hydrocarbon stream free or sub-stantially free of butadiene.
4. A process as defined in claim 2, wherein the hydrocarbon fraction obtained from the butene-1 and/or butene-2 isomerisation stage is fed to the synthesis section after mixing with the C4 hydrocarbon stream free or sub-stantially free of butadiene.
5. A process as defined in claim 1, 2 or 3, wherein the isomerisation stage is effected by feeding only the cis and trans butene-2.
6. A process as defined in claim 4, wherein the isomerisation stage is effected by feeding only the cis and trans butene-2.
7. A process as defined in claim 1, 2 or 3, wherein the acid ion exchange resin is of the sulphonated divinylbenzene-styrene type.
8. A process as defined in claim 6, wherein the acid ion exchange resin is of the sulphonated divinylbenzene-styrene type.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21384A/82 | 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 |
|---|---|
| CA1220230A true CA1220230A (en) | 1987-04-07 |
Family
ID=11180967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000428516A Expired CA1220230A (en) | 1982-05-20 | 1983-05-19 | Process for producing 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 GR GR71241A patent/GR78857B/el unknown
- 1983-04-28 AU AU14017/83A patent/AU1401783A/en not_active Abandoned
- 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 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 MW MW18/83A patent/MW1883A1/en unknown
- 1983-05-13 LU LU84805A patent/LU84805A1/en unknown
- 1983-05-13 KR KR1019830002066A patent/KR860001854B1/en active
- 1983-05-17 YU YU01100/83A patent/YU110083A/en unknown
- 1983-05-17 FR FR8308163A patent/FR2527202B1/en not_active Expired
- 1983-05-18 DK DK221683A patent/DK221683A/en not_active Application Discontinuation
- 1983-05-18 BG BG061013A patent/BG37678A3/en unknown
- 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 DD DD83251077A patent/DD209803A5/en unknown
- 1983-05-19 PT PT76730A patent/PT76730B/en unknown
- 1983-05-19 BE BE0/210806A patent/BE896787A/en not_active IP Right Cessation
- 1983-05-19 DE DE19833318301 patent/DE3318301A1/en not_active Withdrawn
- 1983-05-20 JP JP58087816A patent/JPS58210039A/en active Pending
- 1983-05-20 NL NL8301819A patent/NL8301819A/en not_active Application Discontinuation
- 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
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