CA1232919A - Process for the recovery of polymerization grade butene-1 - Google Patents
Process for the recovery of polymerization grade butene-1Info
- Publication number
- CA1232919A CA1232919A CA000459574A CA459574A CA1232919A CA 1232919 A CA1232919 A CA 1232919A CA 000459574 A CA000459574 A CA 000459574A CA 459574 A CA459574 A CA 459574A CA 1232919 A CA1232919 A CA 1232919A
- Authority
- CA
- Canada
- Prior art keywords
- stream
- butene
- polymerization grade
- butadiene
- isobutene
- 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
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/08—Alkenes with four carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Extraction Or Liquid Replacement (AREA)
- Detergent Compositions (AREA)
Abstract
"PROCESS FOR THE RECOVERY OF POLYMERIZATION GRADE BUT-ENE-1"
Abstract of the disclosure Polymerizaiton grade butene-1 is recovered from a C4 stream containing butene-1, isobutane, isobutene, n-butane, buteanes-2 and reduced amounts of C3 and C5 hydro-carbons, butadiene and acetylenic hydrocarbons, by sub-mitting the stream to the following stages: etherifying with an aliphatic alcohol to the purpose of eliminating the isobutene, which is transformed into the alkyl-tert-butyl ether corresponding to the alcohol used, separa-tion of the tertiary ether thus formed from the remain-ing of the stream, separation by means of distillation of the isobutane, separation from the residual stream, by distillation, of butene-1 at a purity level of from 80% to 95%, selective hydrogenation of the butadiene and of the acetylenic derivatives contained in the said stream of butene-1 at the said purity level, distillation of the hydrogenated stream with separation of polymerization grade butene-1.
Abstract of the disclosure Polymerizaiton grade butene-1 is recovered from a C4 stream containing butene-1, isobutane, isobutene, n-butane, buteanes-2 and reduced amounts of C3 and C5 hydro-carbons, butadiene and acetylenic hydrocarbons, by sub-mitting the stream to the following stages: etherifying with an aliphatic alcohol to the purpose of eliminating the isobutene, which is transformed into the alkyl-tert-butyl ether corresponding to the alcohol used, separa-tion of the tertiary ether thus formed from the remain-ing of the stream, separation by means of distillation of the isobutane, separation from the residual stream, by distillation, of butene-1 at a purity level of from 80% to 95%, selective hydrogenation of the butadiene and of the acetylenic derivatives contained in the said stream of butene-1 at the said purity level, distillation of the hydrogenated stream with separation of polymerization grade butene-1.
Description
~Z3~
CASE _1803 ~ he present invention relate~ to a proce~s for the recovery ~ po3.ymerization ~rade butene~1.
l'he butene-1 is contained in the C~ h~drocarbo~
strea~ns consisting of ~arlable percentages o~ the ~ol 5 lowin~ co~ponent~: butene-1, isobutane1 i~obuteneg n~
bu~ane, butenes-29 C3 and ~5 hydrocarbons both ~aturated . and o~ ole~inic charaeter, butadiene; ace-tylenic deriv-; ati~es.
~he ~4 hydrocarbon stxeam~ to be llsed as the raw materi~l~ according to the present in~entio~ ha~e a low ~ontent o.~ bu~adiene and acetylenic derivative39 qo if the starting batch is originating from steam cracking proce~e~9 the bu~adiene co~tained the~ei~ r~e per oerltages has to be remo~ed by mean~ of a solvent or an~
other process.
; ~he compo~ition o~ the C4 hydrocarbon ~treams tv ~e u~ed aocording to the present inve~tion i~ c~mpri~ed within the ~ollowin~ ranges:
3 0~2 1~5 % by weight ~0 i-C 1 - 30 ~ ~y weight : i-C4- 10 - 60 % by ~eight ^ n-C 3 - 20 ~ by wei~ht C4- 10 - 40 % b~ welght ?-~4- 8 - 30 ~ by T~eight C5 0.1 - 1,0 % by weight Butadie~e ~ A¢etyle~ic0~1 - 6 ~ ~y weight The problem to be fa¢ed is the r~o~ery o~ the but-e~e-1 keeping a~ low a~ po~sible the tran~orm~tion o~
ute~e-1 into butene-2 in the stage of t~e selective hydrogenation of the butadie~e and the ~cetylenlc de~
::
.
9~g ri~ati~es 0 The art kno~ln te~ches that the selecti~e hydrogena tlon ~l the butadiene axld the acetylenlc hydrocarbon~
ha~3 to be eîfected before the sepa~ation stage~ o~ the 5 variou~ components from the butene-1, but ~ en opera t-ing by means o~ the l~nown F~rt proce~ses~ to~ether ~ith the hydrogenation al,~o a noticeable isomeriz~tion Ot~C~
o:E the buterle-1 to b~tene-2.
~he rate of ~uch isomeriza tion depends orl the quan-ti ~ o:~ butadiene allo~ved by the speci:~icat-loll~ oï but ene-1~ The lnwer i~ the ma~imum content of butadiene al~
lowed b~r the ~peci~ication.Y of butene-1, the lower must;
be the quantity of the re~idual butadiene in the ~4 stream a~ter ~he h~drogenation~ snd the higher the lo~ o~ but~
ene~1 becau~3e of the iso~erization to butene~2.
~or purely indicative rea~ons, ~tarting ~rom a con tent of butadiene in the stream to be fed to the hydro-genation ~tage OI about 2%, if the maxi.mum allo~ved con-tent of butadiene in the ~pecifications for b!lter~e-1 is : 20 200 ppm, the lo~ o~ bute~e-1 because o~ the isomeriza-tion iA about of 2~ ~y wei~ht, if the butene-1 specifica ~ tion allow~ a ~aximum content o~ 50 ppm o~ butadiene, : ~ the iso~erizatlon lo~s o~ bute~e-1 i~ hi~her than 5% by ~eightO
It has now been surpri~i~gly found that i~ i~ po~-ible to reduce the disadvantages o~ the tech~iq~e ~rom ~; the prior art, ~y resorting to a selective hydrogenation stage o~ the butadiene and acetylenic derivstives, po~-~ : itio~ed in a suitable point of the plant.
: ~ 30 ~he a4 stream i~ ~ubmitted to the oonventional trea~
men~s for ~he ~eparætion of isobut~n~ by mean~ of tr~n~ :~
''' ~;
. ~ .: . . , :: : ~ ''' ' : ,.
;~2329~
~ox~i.n~ it into an ~ yl--tert.~bu-tyl ether by reaction . with an ali.pha-kic alcohol~ pre~erably methanol~ i~ the presence o~ ~ heterogeneou~ catalyst ~;th ~unctional sulphonic ~roups on a styrene~divynilberlzene matrix~ in ; 5 particular o~ the ~mberly~t 15 type~ , By mea~s o~ the reacti.ons de~cri~ed, p.ractical~y all the i~o~utene i~ ~.rans~ormed i~to an alkyl-tert~bu-tyl ether~ wh~cl~ turn removed by di~tillatio~ in a l~rlow~ ~anner.
The process according to the present invsntion com pri.s~s the stages o~ to di~till in a ~ir~t disti.llati.on column operated at a pressure in the .ra~ge ~.rom 5 to 20 - abs. atm,, the Cq ~rac-tion~ containin~ the previou~ly ~et forth cornponexlt~;, fx ee f`.rom isobu tene or sub~tant~
l~r f~ee :~rom i~obutene$ ohtaining a ~op rtream consi~t~
ing e~sentially OI isobutane1 and a bo ttom ~tream con~
~i~ting o~ the residual compone2~ts9 whioh i~ in turn di~:
:~ ~ tilled in a second dis tillation column ~t a pre~ure compri~ed between 3 and 10 E3bs . atm~, obtaixling a top ~tream con~isting of butene~1 at R purity level wi~hi~
the range from 80% to ~5% (contai~ing butene-1 plu~ fun damentally butane and butadiene ~ acetylenic deriPatives ) ~: and a bottom stream containing high boilin~ oômpound~, n-butane ~nd t~iY- and tran~- butene-~.
~he top ~tream from the seoond distill~tion colu~
Eed to ~ ~elective hydrogenation u2~it of the butadi-ene and the acetylenic derivati.~es" the ooncentra~ion of ~aid compounds being redueed to ~ Yalue within the r~nge Xro~ 30 to 200 ppm ~n order to fulfi.lling the speci~i-;: ~ 30 c~ions for the polymeri%ation ~rade butene-1 .
q`he hydroæexlati~g unit i~ operated under the Iol-:,:
.
~:
:~, .
~'~3~ 9 ~ o lowi~ oondi.tion~: in:l et tempe~ature 35 to 50G9 opexat irlg p:res~ure ~ to 20 Qbs o a t~n~
'~he .stx eam o~i~irl~ tin3 ~rom the selectlYe hydrogexla tion unit;7 dep;rived o:~ the die~io a~ld ace~ylenic corr pol~.nd~3~ is f:ed to a distillat:Lon coluu!~ oper~ted at~ ~
p:re~sure within the ran~e :Erom 3 -to 10 ab~ 4 ~tm.,, obtain in~ f'rom a plate close to the top o;~ the coll~rr~ pol~mer izatio~ grade bu-texle 1 and as -the bot tom strcam, .n~but;-ane and butenes~27 with reduced amountæ o:f butene-10 ~he proae~ acoording to the present inventio~ m~Ln tains its ~.dvanta~es o~ requirin qui-tc ~oft reac-tion condi~ion~ al~o in the ca~e that the select:ive hy-lrogen,E,~
: tio~ ~le e~fected in the presen~e o~ ~nhibitors o~ -the l~o~erization o-f bond ~rom butene 1 to bu~ene-2 to be added to the batch C4.
'urthexnlnre the procesa accordin~ to the pre~ent i~vention has in any cases the additional adva~tatre of : Rllo~in~ the dlmensions to be xeduced o~ ~he e~uipme~
required by the seleoti~e h~drogenation a~d a~ ~ cons :~ 20 quence of the investment capital~ -As ~or the types of the component~ o~ the ~riou~
stream~ referenc~ shall be made to the followjl~g ~a~ple, hich h~s not to be i~tended a~ limltative o~ the ~.nYen ion i~ regard to the concentratlol~ o~ the variou~ oom pone~t~ in a~y ~in~le ~tre~m and to the operational pres sure~ o~ the various stage3.
E:~:ample 'I'he :Example has ~een performed according to the s~hematic iI~ trat1 on of the attached drawir~g~ which i~
: . 30 not Iimi ta~ive of the inven t;ion 9 irl whieh ( 1~ is the C4 : :
trearQ çomprisi.ngS a~nong other~ butene-l, isobute~e, : : : .
: ~ .
hutadiexle anc~s acetyle~ic deriv~tive~7 (2) i9 a E~trealn o:E me~h~rso3. beillg f'-ld to the etheri:Eyin~ unit ~1~) o:~
the lsobutene9 (3) i~ the strea.m o:f methyl~tert~but e tklex~ produ-~ed ~ ( 4 ) ics the ~ eam sub,~tantia1 ly ~ree :Erom iSObll~erle9 (18) is the ~ir,~3t dlsti:Llatiorl co~.um~
opexa ~ed a t about 14 abs . at~Q~ ~ ( 5 ) i.~ ~he top s tr~eS~n esserltially coSnpri~3:~xlg isobutane9 (~) ic~ ~he re~idual stream which i,s ~ed to -the ~econd di~f-3t11la~ion colllm (19) opexated at ~ pressure of` about 6 ~bs~ atmO~ (7) i,9 e ~txeam eonta-Lning e~s~tially bu-te1ne~1~ (8j ls a ~JG~eam cont~irlin~ tkle heavy produc ts; t'rle s tr eam (7 ) l~
:fed -to the hydrogenati.on unit (17) to whi.ch hydxo~en i8 fed by the line (9), and from which the s-tream ~11 ) iB
discharged ~ essentlal.ly eonsi ~Iting o:~ i;he excess hydro-~gen ~ld b~tene-1; (10) iæ the hydro~enated ~tream which i0 fed to the fractionatiorl column ~20) operated a~
pressure o:F abou-t 7 abs. atmO ~ from the top o:E which ~
~liream ( 12 ) i ob tai~ed 9 con~isting of u~ o~den,s~ble mat ter and butelle~ rom ~he ~enth plate ~.rom the top ~L
~0 ~treRm ~13 ) bein~; obtnined oi~ po:l.ymeriz~tion ~rade but-ene-1, and f'rom the bottom the reæidue (14) being obtained, sub3tantial.1y con~isting of n~ tane arld bu l;e~e~2 0 ~he stream ( 1 5 ) iB the sum Q:~ the stl~eam~ ~ 5 ), (8 3 a~ d ~ 1 4 ) .
The balance o:l~ the matter~ o~ the proce~ is shown ~n the followin,~ Table, where the position number~ are ref erred to the drawing .
~, ~2329~L~
o o o a) ~
~ .
~: III,,,,,, o 3 ~ ~ 0 !n O I O ~G ~ I O
CO '~-s ~ l l l l ~ l 0 c~ ~ l ~
bO I I I I I ID N t` I ~S\
0 ~ - O
3 l l o o ~ ~ m o bD I 8 .
~ a) c ~' s W, ~ ~ o~oLn ~ ~ ~
. ~ 0 a) ~ ~ 0 o 3 1 ~ 0 0 ~ o ~ \~ I o I IN ~) 0 ~ O ~ ~J I a ) W I I O ~D N 0 ~` I O
~ t` t` ~ 0 0 ~" ~ ~ , ~ 1 o ~ ~ ~ ~ O O O O l O
CO C ~1 1 0 ~S~
S I 0 0 .-1 t`ID O ~ ~) ~1 00 ~ ~ CO
, I O ~ O ~ o ~ I i O
N ~) ~1 ~ O
S I o,, ~ ;o~ o~
O t`'J 0 ~
3 l o ~ ~\i o ot~ ~ 0r~ O
: ` : ~ ~ ~ ~ ~ O
O O O O O O OO o O
S
D ~J C
C O C C T-- ~ ~3 Q) O ~ , o s~ ~ ~ I ~ c m ~ s~
~ 3 3 C m 3 ~ m u~ O O J~ ~ m ~
~: :
~'~32~L9 ~I 11 ~ ~1 LS~ L-- ~1 CO O
G ~ ~ f 11 ~ ~ O ~ ~ ~
~ I 'h ! 11 0 co ~ O ~n cn c~
. ' . . I 1 E: I 11 11 11 11 Il .. o I 11 11 11 11 IJ 11 ~_ , t~ I 11 11 11 ~ 11 0 11 ~ CO 11 0 I b~ I1~ 11 11 11 11 11 . , I.~d 1 ll ll ll ll ll ll t 11 11 t- ~ O ~ ~t~ 11 11 <~
11 11 o o cn P~ C~o 11 11 o ` I il 11 ~ O 11 11 0 ;: ~ I ~ I 1l 1l 1l n1l .~ ~ I ~ I o11 11 11 o ~ 1111 11o : ~ ~ I U U 11 11 11 1111 11~
: ~ ~ t~g~~ ~1 11 11a:) 11 11 ~IO
n 1l 1l 1l u 1~
~ 1 11 11 1l 11 t ~ U 1l 1l 1l 1l U
O U O
l H
. I ~ n o c~ l o O ~ I h : I - 11t!J ~ N n ~ Nc~ il ~; ..
~ I U ~ U '~ UCS~
. D a O ~ o O ~: a I ~i J, O
rl ~ ~ D O i ~ S~I ~ ¢
o o ~ t~)a~ t~; ~ E~
V H H 3 ~ s . ~ v ~, ~
~, 7~ : ~
CASE _1803 ~ he present invention relate~ to a proce~s for the recovery ~ po3.ymerization ~rade butene~1.
l'he butene-1 is contained in the C~ h~drocarbo~
strea~ns consisting of ~arlable percentages o~ the ~ol 5 lowin~ co~ponent~: butene-1, isobutane1 i~obuteneg n~
bu~ane, butenes-29 C3 and ~5 hydrocarbons both ~aturated . and o~ ole~inic charaeter, butadiene; ace-tylenic deriv-; ati~es.
~he ~4 hydrocarbon stxeam~ to be llsed as the raw materi~l~ according to the present in~entio~ ha~e a low ~ontent o.~ bu~adiene and acetylenic derivative39 qo if the starting batch is originating from steam cracking proce~e~9 the bu~adiene co~tained the~ei~ r~e per oerltages has to be remo~ed by mean~ of a solvent or an~
other process.
; ~he compo~ition o~ the C4 hydrocarbon ~treams tv ~e u~ed aocording to the present inve~tion i~ c~mpri~ed within the ~ollowin~ ranges:
3 0~2 1~5 % by weight ~0 i-C 1 - 30 ~ ~y weight : i-C4- 10 - 60 % by ~eight ^ n-C 3 - 20 ~ by wei~ht C4- 10 - 40 % b~ welght ?-~4- 8 - 30 ~ by T~eight C5 0.1 - 1,0 % by weight Butadie~e ~ A¢etyle~ic0~1 - 6 ~ ~y weight The problem to be fa¢ed is the r~o~ery o~ the but-e~e-1 keeping a~ low a~ po~sible the tran~orm~tion o~
ute~e-1 into butene-2 in the stage of t~e selective hydrogenation of the butadie~e and the ~cetylenlc de~
::
.
9~g ri~ati~es 0 The art kno~ln te~ches that the selecti~e hydrogena tlon ~l the butadiene axld the acetylenlc hydrocarbon~
ha~3 to be eîfected before the sepa~ation stage~ o~ the 5 variou~ components from the butene-1, but ~ en opera t-ing by means o~ the l~nown F~rt proce~ses~ to~ether ~ith the hydrogenation al,~o a noticeable isomeriz~tion Ot~C~
o:E the buterle-1 to b~tene-2.
~he rate of ~uch isomeriza tion depends orl the quan-ti ~ o:~ butadiene allo~ved by the speci:~icat-loll~ oï but ene-1~ The lnwer i~ the ma~imum content of butadiene al~
lowed b~r the ~peci~ication.Y of butene-1, the lower must;
be the quantity of the re~idual butadiene in the ~4 stream a~ter ~he h~drogenation~ snd the higher the lo~ o~ but~
ene~1 becau~3e of the iso~erization to butene~2.
~or purely indicative rea~ons, ~tarting ~rom a con tent of butadiene in the stream to be fed to the hydro-genation ~tage OI about 2%, if the maxi.mum allo~ved con-tent of butadiene in the ~pecifications for b!lter~e-1 is : 20 200 ppm, the lo~ o~ bute~e-1 because o~ the isomeriza-tion iA about of 2~ ~y wei~ht, if the butene-1 specifica ~ tion allow~ a ~aximum content o~ 50 ppm o~ butadiene, : ~ the iso~erizatlon lo~s o~ bute~e-1 i~ hi~her than 5% by ~eightO
It has now been surpri~i~gly found that i~ i~ po~-ible to reduce the disadvantages o~ the tech~iq~e ~rom ~; the prior art, ~y resorting to a selective hydrogenation stage o~ the butadiene and acetylenic derivstives, po~-~ : itio~ed in a suitable point of the plant.
: ~ 30 ~he a4 stream i~ ~ubmitted to the oonventional trea~
men~s for ~he ~eparætion of isobut~n~ by mean~ of tr~n~ :~
''' ~;
. ~ .: . . , :: : ~ ''' ' : ,.
;~2329~
~ox~i.n~ it into an ~ yl--tert.~bu-tyl ether by reaction . with an ali.pha-kic alcohol~ pre~erably methanol~ i~ the presence o~ ~ heterogeneou~ catalyst ~;th ~unctional sulphonic ~roups on a styrene~divynilberlzene matrix~ in ; 5 particular o~ the ~mberly~t 15 type~ , By mea~s o~ the reacti.ons de~cri~ed, p.ractical~y all the i~o~utene i~ ~.rans~ormed i~to an alkyl-tert~bu-tyl ether~ wh~cl~ turn removed by di~tillatio~ in a l~rlow~ ~anner.
The process according to the present invsntion com pri.s~s the stages o~ to di~till in a ~ir~t disti.llati.on column operated at a pressure in the .ra~ge ~.rom 5 to 20 - abs. atm,, the Cq ~rac-tion~ containin~ the previou~ly ~et forth cornponexlt~;, fx ee f`.rom isobu tene or sub~tant~
l~r f~ee :~rom i~obutene$ ohtaining a ~op rtream consi~t~
ing e~sentially OI isobutane1 and a bo ttom ~tream con~
~i~ting o~ the residual compone2~ts9 whioh i~ in turn di~:
:~ ~ tilled in a second dis tillation column ~t a pre~ure compri~ed between 3 and 10 E3bs . atm~, obtaixling a top ~tream con~isting of butene~1 at R purity level wi~hi~
the range from 80% to ~5% (contai~ing butene-1 plu~ fun damentally butane and butadiene ~ acetylenic deriPatives ) ~: and a bottom stream containing high boilin~ oômpound~, n-butane ~nd t~iY- and tran~- butene-~.
~he top ~tream from the seoond distill~tion colu~
Eed to ~ ~elective hydrogenation u2~it of the butadi-ene and the acetylenic derivati.~es" the ooncentra~ion of ~aid compounds being redueed to ~ Yalue within the r~nge Xro~ 30 to 200 ppm ~n order to fulfi.lling the speci~i-;: ~ 30 c~ions for the polymeri%ation ~rade butene-1 .
q`he hydroæexlati~g unit i~ operated under the Iol-:,:
.
~:
:~, .
~'~3~ 9 ~ o lowi~ oondi.tion~: in:l et tempe~ature 35 to 50G9 opexat irlg p:res~ure ~ to 20 Qbs o a t~n~
'~he .stx eam o~i~irl~ tin3 ~rom the selectlYe hydrogexla tion unit;7 dep;rived o:~ the die~io a~ld ace~ylenic corr pol~.nd~3~ is f:ed to a distillat:Lon coluu!~ oper~ted at~ ~
p:re~sure within the ran~e :Erom 3 -to 10 ab~ 4 ~tm.,, obtain in~ f'rom a plate close to the top o;~ the coll~rr~ pol~mer izatio~ grade bu-texle 1 and as -the bot tom strcam, .n~but;-ane and butenes~27 with reduced amountæ o:f butene-10 ~he proae~ acoording to the present inventio~ m~Ln tains its ~.dvanta~es o~ requirin qui-tc ~oft reac-tion condi~ion~ al~o in the ca~e that the select:ive hy-lrogen,E,~
: tio~ ~le e~fected in the presen~e o~ ~nhibitors o~ -the l~o~erization o-f bond ~rom butene 1 to bu~ene-2 to be added to the batch C4.
'urthexnlnre the procesa accordin~ to the pre~ent i~vention has in any cases the additional adva~tatre of : Rllo~in~ the dlmensions to be xeduced o~ ~he e~uipme~
required by the seleoti~e h~drogenation a~d a~ ~ cons :~ 20 quence of the investment capital~ -As ~or the types of the component~ o~ the ~riou~
stream~ referenc~ shall be made to the followjl~g ~a~ple, hich h~s not to be i~tended a~ limltative o~ the ~.nYen ion i~ regard to the concentratlol~ o~ the variou~ oom pone~t~ in a~y ~in~le ~tre~m and to the operational pres sure~ o~ the various stage3.
E:~:ample 'I'he :Example has ~een performed according to the s~hematic iI~ trat1 on of the attached drawir~g~ which i~
: . 30 not Iimi ta~ive of the inven t;ion 9 irl whieh ( 1~ is the C4 : :
trearQ çomprisi.ngS a~nong other~ butene-l, isobute~e, : : : .
: ~ .
hutadiexle anc~s acetyle~ic deriv~tive~7 (2) i9 a E~trealn o:E me~h~rso3. beillg f'-ld to the etheri:Eyin~ unit ~1~) o:~
the lsobutene9 (3) i~ the strea.m o:f methyl~tert~but e tklex~ produ-~ed ~ ( 4 ) ics the ~ eam sub,~tantia1 ly ~ree :Erom iSObll~erle9 (18) is the ~ir,~3t dlsti:Llatiorl co~.um~
opexa ~ed a t about 14 abs . at~Q~ ~ ( 5 ) i.~ ~he top s tr~eS~n esserltially coSnpri~3:~xlg isobutane9 (~) ic~ ~he re~idual stream which i,s ~ed to -the ~econd di~f-3t11la~ion colllm (19) opexated at ~ pressure of` about 6 ~bs~ atmO~ (7) i,9 e ~txeam eonta-Lning e~s~tially bu-te1ne~1~ (8j ls a ~JG~eam cont~irlin~ tkle heavy produc ts; t'rle s tr eam (7 ) l~
:fed -to the hydrogenati.on unit (17) to whi.ch hydxo~en i8 fed by the line (9), and from which the s-tream ~11 ) iB
discharged ~ essentlal.ly eonsi ~Iting o:~ i;he excess hydro-~gen ~ld b~tene-1; (10) iæ the hydro~enated ~tream which i0 fed to the fractionatiorl column ~20) operated a~
pressure o:F abou-t 7 abs. atmO ~ from the top o:E which ~
~liream ( 12 ) i ob tai~ed 9 con~isting of u~ o~den,s~ble mat ter and butelle~ rom ~he ~enth plate ~.rom the top ~L
~0 ~treRm ~13 ) bein~; obtnined oi~ po:l.ymeriz~tion ~rade but-ene-1, and f'rom the bottom the reæidue (14) being obtained, sub3tantial.1y con~isting of n~ tane arld bu l;e~e~2 0 ~he stream ( 1 5 ) iB the sum Q:~ the stl~eam~ ~ 5 ), (8 3 a~ d ~ 1 4 ) .
The balance o:l~ the matter~ o~ the proce~ is shown ~n the followin,~ Table, where the position number~ are ref erred to the drawing .
~, ~2329~L~
o o o a) ~
~ .
~: III,,,,,, o 3 ~ ~ 0 !n O I O ~G ~ I O
CO '~-s ~ l l l l ~ l 0 c~ ~ l ~
bO I I I I I ID N t` I ~S\
0 ~ - O
3 l l o o ~ ~ m o bD I 8 .
~ a) c ~' s W, ~ ~ o~oLn ~ ~ ~
. ~ 0 a) ~ ~ 0 o 3 1 ~ 0 0 ~ o ~ \~ I o I IN ~) 0 ~ O ~ ~J I a ) W I I O ~D N 0 ~` I O
~ t` t` ~ 0 0 ~" ~ ~ , ~ 1 o ~ ~ ~ ~ O O O O l O
CO C ~1 1 0 ~S~
S I 0 0 .-1 t`ID O ~ ~) ~1 00 ~ ~ CO
, I O ~ O ~ o ~ I i O
N ~) ~1 ~ O
S I o,, ~ ;o~ o~
O t`'J 0 ~
3 l o ~ ~\i o ot~ ~ 0r~ O
: ` : ~ ~ ~ ~ ~ O
O O O O O O OO o O
S
D ~J C
C O C C T-- ~ ~3 Q) O ~ , o s~ ~ ~ I ~ c m ~ s~
~ 3 3 C m 3 ~ m u~ O O J~ ~ m ~
~: :
~'~32~L9 ~I 11 ~ ~1 LS~ L-- ~1 CO O
G ~ ~ f 11 ~ ~ O ~ ~ ~
~ I 'h ! 11 0 co ~ O ~n cn c~
. ' . . I 1 E: I 11 11 11 11 Il .. o I 11 11 11 11 IJ 11 ~_ , t~ I 11 11 11 ~ 11 0 11 ~ CO 11 0 I b~ I1~ 11 11 11 11 11 . , I.~d 1 ll ll ll ll ll ll t 11 11 t- ~ O ~ ~t~ 11 11 <~
11 11 o o cn P~ C~o 11 11 o ` I il 11 ~ O 11 11 0 ;: ~ I ~ I 1l 1l 1l n1l .~ ~ I ~ I o11 11 11 o ~ 1111 11o : ~ ~ I U U 11 11 11 1111 11~
: ~ ~ t~g~~ ~1 11 11a:) 11 11 ~IO
n 1l 1l 1l u 1~
~ 1 11 11 1l 11 t ~ U 1l 1l 1l 1l U
O U O
l H
. I ~ n o c~ l o O ~ I h : I - 11t!J ~ N n ~ Nc~ il ~; ..
~ I U ~ U '~ UCS~
. D a O ~ o O ~: a I ~i J, O
rl ~ ~ D O i ~ S~I ~ ¢
o o ~ t~)a~ t~; ~ E~
V H H 3 ~ s . ~ v ~, ~
~, 7~ : ~
Claims
1. Process for the recovery of polymerization grade butene-1 from a C4 fractionwhich contains it, free from isobutene or substantially free from isobutene, compris ing the stages of to distill in a first distillation column, at a pressure comprised in the range form 5 to 20 abs. atm., such fraction, obtaining a top stream es-sentially containing isobutane and a bottom stream con-taining the residual components, and of the distill the stream containing the residual components, in a second distillation column, at a pressure comprised in the ran ge from 3 to 10 abs. atm., obtaining a top stream of but ene-1 at a purity level of from 80 to 95% and a bottom stream comprising the high boiling compounds, n-butane and butenes-2 cis- and trans-, characterized in that the top stream from the second distillation column is fed to a selective hydrogenation unit of the butadiene and the acetylenic derivatives, such compounds being reduced to a concentration comprised within the range from 30 to 200 ppm, the stream originating from the selective hydro genation unit being finally fed to a distillation column, operated at a pressure comprised within the range form 3 to 10 abs. atm., obtaining from a plate close to the top of the column, polymerization grade butene-1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22294/83A IT1194351B (en) | 1983-07-28 | 1983-07-28 | PROCEDURE FOR THE RECOVERY OF BUTENE-1 DEGREE POLYMERIZATION |
| IT22294A/83 | 1983-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1232919A true CA1232919A (en) | 1988-02-16 |
Family
ID=11194295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000459574A Expired CA1232919A (en) | 1983-07-28 | 1984-07-24 | Process for the recovery of polymerization grade butene-1 |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS6051131A (en) |
| KR (1) | KR870000583B1 (en) |
| AU (1) | AU561302B2 (en) |
| BE (1) | BE900248A (en) |
| BR (1) | BR8403665A (en) |
| CA (1) | CA1232919A (en) |
| CS (1) | CS250667B2 (en) |
| DD (1) | DD222000A5 (en) |
| DE (1) | DE3426349A1 (en) |
| DK (1) | DK369484A (en) |
| ES (1) | ES534969A0 (en) |
| FR (1) | FR2549825B1 (en) |
| GB (1) | GB2144146B (en) |
| GR (1) | GR82261B (en) |
| HU (1) | HUT36762A (en) |
| IT (1) | IT1194351B (en) |
| LU (1) | LU85466A1 (en) |
| NL (1) | NL8402384A (en) |
| NO (1) | NO843022L (en) |
| PL (1) | PL248948A1 (en) |
| PT (1) | PT78990B (en) |
| RO (1) | RO90623A (en) |
| SE (1) | SE8403426L (en) |
| TR (1) | TR22082A (en) |
| YU (1) | YU132184A (en) |
| ZA (1) | ZA845088B (en) |
Families Citing this family (26)
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|---|---|---|---|---|
| JP2003063281A (en) * | 2001-08-29 | 2003-03-05 | Sanwa Tekki Corp | Trolly line hanger ear and insulation coupling element |
| US8633915B2 (en) | 2007-10-04 | 2014-01-21 | Apple Inc. | Single-layer touch-sensitive display |
| US20090174676A1 (en) | 2008-01-04 | 2009-07-09 | Apple Inc. | Motion component dominance factors for motion locking of touch sensor data |
| US8487898B2 (en) | 2008-04-25 | 2013-07-16 | Apple Inc. | Ground guard for capacitive sensing |
| US8576193B2 (en) | 2008-04-25 | 2013-11-05 | Apple Inc. | Brick layout and stackup for a touch screen |
| US8319747B2 (en) | 2008-12-11 | 2012-11-27 | Apple Inc. | Single layer touch panel with segmented drive and sense electrodes |
| US9261997B2 (en) | 2009-02-02 | 2016-02-16 | Apple Inc. | Touch regions in diamond configuration |
| US8922521B2 (en) | 2009-02-02 | 2014-12-30 | Apple Inc. | Switching circuitry for touch sensitive display |
| US8593410B2 (en) | 2009-04-10 | 2013-11-26 | Apple Inc. | Touch sensor panel design |
| US8957874B2 (en) | 2009-06-29 | 2015-02-17 | Apple Inc. | Touch sensor panel design |
| US9652088B2 (en) | 2010-07-30 | 2017-05-16 | Apple Inc. | Fabrication of touch sensor panel using laser ablation |
| US9329723B2 (en) | 2012-04-16 | 2016-05-03 | Apple Inc. | Reconstruction of original touch image from differential touch image |
| US9886141B2 (en) | 2013-08-16 | 2018-02-06 | Apple Inc. | Mutual and self capacitance touch measurements in touch panel |
| US10936120B2 (en) | 2014-05-22 | 2021-03-02 | Apple Inc. | Panel bootstraping architectures for in-cell self-capacitance |
| US10289251B2 (en) | 2014-06-27 | 2019-05-14 | Apple Inc. | Reducing floating ground effects in pixelated self-capacitance touch screens |
| US9280251B2 (en) | 2014-07-11 | 2016-03-08 | Apple Inc. | Funneled touch sensor routing |
| US9880655B2 (en) | 2014-09-02 | 2018-01-30 | Apple Inc. | Method of disambiguating water from a finger touch on a touch sensor panel |
| WO2016048269A1 (en) | 2014-09-22 | 2016-03-31 | Onamp Research Llc | Ungrounded user signal compensation for pixelated self-capacitance touch sensor panel |
| EP3213173A4 (en) | 2014-10-27 | 2018-06-06 | Apple Inc. | Pixelated self-capacitance water rejection |
| US10795488B2 (en) | 2015-02-02 | 2020-10-06 | Apple Inc. | Flexible self-capacitance and mutual capacitance touch sensing system architecture |
| US10488992B2 (en) | 2015-03-10 | 2019-11-26 | Apple Inc. | Multi-chip touch architecture for scalability |
| US10365773B2 (en) | 2015-09-30 | 2019-07-30 | Apple Inc. | Flexible scan plan using coarse mutual capacitance and fully-guarded measurements |
| US10534481B2 (en) | 2015-09-30 | 2020-01-14 | Apple Inc. | High aspect ratio capacitive sensor panel |
| AU2017208277B2 (en) | 2016-09-06 | 2018-12-20 | Apple Inc. | Back of cover touch sensors |
| US10386965B2 (en) | 2017-04-20 | 2019-08-20 | Apple Inc. | Finger tracking in wet environment |
| US11662867B1 (en) | 2020-05-30 | 2023-05-30 | Apple Inc. | Hover detection on a touch sensor panel |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1280845B (en) * | 1965-10-29 | 1968-10-24 | Huels Chemische Werke Ag | Process for the selective hydrogenation of butadiene- (1,3) in a C-hydrocarbon mixture containing larger amounts of 1-butene and small amounts of butadiene- (1, 3) |
| FR2474024A1 (en) * | 1980-01-23 | 1981-07-24 | Inst Francais Du Petrole | PROCESS FOR PRODUCING BUTENE-1 FROM A C4 CUTTING OF HYDROCARBONS |
| FR2493306A1 (en) * | 1980-10-30 | 1982-05-07 | Inst Francais Du Petrole | High-purity 1-butene recovery from mixed butene streams - by isobutene polymerisation to gasoline and fractionation |
| FR2495605A1 (en) * | 1980-12-05 | 1982-06-11 | Inst Francais Du Petrole | High-purity butene-1 isolated from steam cracker butene(s) - by conversion of isobutene to methyl tert. butyl ether and fractionation |
| FR2508437A1 (en) * | 1981-06-26 | 1982-12-31 | Inst Francais Du Petrole | Steam-cracker butene(s) cut upgraded to pure butene-1, gasoline - and opt. jet fuel via initial polymerisation-dismutation on acid catalyst |
| US4820472A (en) * | 1981-07-14 | 1989-04-11 | Westinghouse Electric Corp. | Nuclear reactor spent fuel storage rack |
-
1983
- 1983-07-28 IT IT22294/83A patent/IT1194351B/en active
-
1984
- 1984-06-27 SE SE8403426A patent/SE8403426L/en not_active Application Discontinuation
- 1984-07-03 ZA ZA845088A patent/ZA845088B/en unknown
- 1984-07-04 GR GR75186A patent/GR82261B/el unknown
- 1984-07-05 CS CS845243A patent/CS250667B2/en unknown
- 1984-07-06 GB GB08417309A patent/GB2144146B/en not_active Expired
- 1984-07-16 LU LU85466A patent/LU85466A1/en unknown
- 1984-07-17 DE DE19843426349 patent/DE3426349A1/en not_active Ceased
- 1984-07-19 BR BR8403665A patent/BR8403665A/en unknown
- 1984-07-23 AU AU30960/84A patent/AU561302B2/en not_active Expired - Fee Related
- 1984-07-23 KR KR1019840004354A patent/KR870000583B1/en active IP Right Grant
- 1984-07-24 CA CA000459574A patent/CA1232919A/en not_active Expired
- 1984-07-25 NO NO843022A patent/NO843022L/en unknown
- 1984-07-25 TR TR22082A patent/TR22082A/en unknown
- 1984-07-26 FR FR8411913A patent/FR2549825B1/en not_active Expired
- 1984-07-26 PL PL24894884A patent/PL248948A1/en unknown
- 1984-07-26 YU YU01321/84A patent/YU132184A/en unknown
- 1984-07-27 HU HU842900A patent/HUT36762A/en unknown
- 1984-07-27 BE BE0/213405A patent/BE900248A/en not_active IP Right Cessation
- 1984-07-27 DD DD84265727A patent/DD222000A5/en unknown
- 1984-07-27 ES ES534969A patent/ES534969A0/en active Granted
- 1984-07-27 PT PT78990A patent/PT78990B/en unknown
- 1984-07-27 DK DK369484A patent/DK369484A/en not_active Application Discontinuation
- 1984-07-27 JP JP59155719A patent/JPS6051131A/en active Pending
- 1984-07-27 RO RO84115361A patent/RO90623A/en unknown
- 1984-07-30 NL NL8402384A patent/NL8402384A/en not_active Application Discontinuation
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