GB2144146A - Process for the recovery of butene-1 - Google Patents

Process for the recovery of butene-1 Download PDF

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Publication number
GB2144146A
GB2144146A GB08417309A GB8417309A GB2144146A GB 2144146 A GB2144146 A GB 2144146A GB 08417309 A GB08417309 A GB 08417309A GB 8417309 A GB8417309 A GB 8417309A GB 2144146 A GB2144146 A GB 2144146A
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United Kingdom
Prior art keywords
butene
stream
weight
butadiene
distillation column
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Granted
Application number
GB08417309A
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GB8417309D0 (en
GB2144146B (en
Inventor
Renzo Comiotto
Maglie Bruno De
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SnamProgetti SpA
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SnamProgetti SpA
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Filing date
Publication date
Priority to IT2229483A priority Critical patent/IT1194351B/en
Application filed by SnamProgetti SpA filed Critical SnamProgetti SpA
Publication of GB8417309D0 publication Critical patent/GB8417309D0/en
Publication of GB2144146A publication Critical patent/GB2144146A/en
Application granted granted Critical
Publication of GB2144146B publication Critical patent/GB2144146B/en
Application status is Expired legal-status Critical

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00Purification; Separation; Use of additives
    • C07C7/005Processes comprising at least two steps in series
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00Purification; Separation; Use of additives
    • C07C7/04Purification; Separation; Use of additives by distillation

Abstract

Polymerization grade butene-1 is recovered from a C4 stream containing butene-1, isobutane, n-butane, butenes-2, reduced amounts of C3 and C5 hydrocarbons, butadiene and acetylenic hydrocarbons, by submitting the stream to the following stages: separation by means of distillation (18) of the isobutane (5), separation from residual stream (6), by distillation (19), of butene-1 (7) at a purity level of from 80% to 95%, selective hydrogenation (17) of the butadiene and of the acetylenic derivatives contained in the stream of butene-1 at the given purity level, and distillation (20) of the hydrogenated stream (10) with separation of polymerization grade butene-1 (13). Isobutene can be removed from the C4 stream prior to its being thus treated by conversion into an ether (16). <IMAGE>

Description

SPECIFICATION Process for the recovery of butene-1 The present invention relates to a process for the recovery of butene-1, e.g. polymerization grade butene-1.

Butene-1 is contained inC4 hydrocarbon streams consisting of various amounts of the following components: butene-1, isobutane, isobutene, n-butane, butenes-2, C3 and C5 saturated and olefinic hydrocarbons, butadiene, and acetylenic derivatives.

The C4 hydrocarbon streams to be used as the raw material according to the present invention should have a low content of butadiene and acetylenic derivatives, so if, for example, the starting material emanates from steam cracking processes, the butadiene contained therein in large amounts should be removed by means of a solvent or in some other way.

The composition of the C4 hydrocarbon stream to be used according to the present invention is preferably as follows: C3 0.2-1.5% by weight i-C4 1-30% by weight i-C4- 10-60% by weight n-C4 3-20% by weight 1-C4 10-40% by weight 2-C4- 8-30% by weight C5 0.1-1.0% by weight Butadiene + Acetylenic 0.1-6% by weight.

The problem to be solved is the recovery of the butene-1, keeping as low as possible the transformation of butene-1 into butene-2 during the selective hydrogenation of the butadiene and the acetylenic derivatives.

The known art discloses that the selective hydrogenation of the butadiene and the acetylenic hydrocarbons has to be effected before the separation of the various components from the butene-1.

However, when the known processes are carried out, a noticeable isomerization of butene-1 to butene-1 occurs during the hydrogenation.

The rate of such isomerization depends on the permitted quantity of butadiene in the butene-1. The lower is the maximum permitted content of butadiene in the butene-1, the lower must be the quantity of residual butadiene in the C4 stream after the hydrogenation, and the higher is the loss of butene-1 as a result of its isomerization to butene-2.

For purely indicative reasons, starting from a content of butadiene of about 2% in the stream to be fed to the hydrogenation stage, if the maximum permitted content of butadiene in the butene-1 is 200 ppm, the loss of butene-1 as a result of isomerization is about 2% by weight; if the maximum permitted content of butadiene in the butene-1 is 50 ppm, the loss of butene-1 as a result of isomerization is higher than 5% by weight.

It has now been surprisingly found that it is possible to reduce the disadvantages of the prior art, the use of a selective hydrogenation of the butadiene and acetylenic derivatives, at a suitable point in the process.

According to the present invention, there is provided a process for the recovery of butene-1 from a C4 fraction which contains butene-1 and which is free or substantially free of isobutene, which process comprises (a) distilling the fraction in a first distillation column at a pressure of from 5 to 20 atmospheres absolute to obtain a head product comprising isobutane and a bottom product comprising residual components; (b) distilling the bottom product comprising residual components in a second distillation column at a pressure of from 3 to 10 atmospheres absolute to obtain a head product comprising butene-1 having a purity of from 80 to 95% and a bottom product comprising high boiling compounds (e.g. n-butane, cis-butene-2 and trans-butene-2); (c) subjecting the head product comprising butene-1 to selective hydrogenation so as to reduce the content of butadiene and acetylenic derivatives of the product to a value of from 30 to 200 ppm; and (d) feeding the product from the selective hydrogenation to a third distillation column, operting at a pressure of from 3 to 10 atmospheres absolute, so as to obtain butene-1 from the vicinity of the head of the column.

The C4 stream is submitted to a conventional treatment for the separation of isobutene by converting it into an alkyl-tert-butyl ether, for example by reaction with an aliphatic alcohol, preferably methanol, and preferably in the presence of a heterogeneous catalyst having functional sulphonic groups on a styrene-divinylbenzene matrix, in particular of the Amberlyst 15 type. In this way, practically all of the isobutene may be converted into an alky-tert-butyl ether, which in turn may be removed by distillation in a known manner.

The process according to the present invention comprises the stages of distilling in a first distillation column, operated at a pressure in the range from 5 to 20 atmospheres absolute, the C4 fraction, containing the previously set forth components, free from isobutene or substantially free from isobutene, obtaining a head stream consisting essentially of isobutane, and a bottom stream consisting of the residual components, which is in turn distilled in a second distillation column at a pressure of from 3 to 10 atmospheres absolute, obtaining a head stream consisting of butene-1 at a purity level within the range from 80% to 95% (containing butene-1 plus fundamentally butane and butadiene plus acetylenic derivatives) and a bottom stream containing high boiling compounds, n-butane and cis- and trans-butene-2.

The head stream from the second distillation column is fed to a selective hydrogenation unit for butadiene and the acetylenic derivatives, the concentration of these compounds being reduced to a value within the range from 30 to 200 ppm in order to fulfil the requirements for polymerization grade butene-1.

The hydrogenating unit may be operated at an inlet temperature of from 35 to 50"C, and at an operating pressure of from 4 to 20 atmospheres absolute.

The stream from the selective hydrogenation unit, deprived of dienic and acetylenic compounds, is fed to a distillation column operated at a pressure within the range of from 3 to 10 atmospheres absolute, there being obtained from a plate close to the head of the column, polymerization grade butene-1, and, as the bottom stream, n-butane and butenes-2, with reduced amounts of butene-1.

The process according to the present invention has the advantage of requiring quite mild reaction conditions, and also that the selective hydrogenation may be effected in the presence of an inhibitor of the isomerization of butene-1 to butene-2, which inhibitor may be added to the C4 fraction.

Furthermore, the process according to the present invention has the additional advantage of allowing the dimensions of the equipment required for the selective hydrogenation, and as a consequence the cost of this equipment, to be reduced.

As for the components of the various streams, reference will be made to the following Example, which is not intended to be limitative of the invention in regard to the concentration of the various components in any single stream and to the operational pressures of the various stages.

Example This Example was performed according to the schematic illustration of the accompanying drawing, which is not limitative of the invention, which shows a C4 stream 1 comprising, among others, butene-1, isobutene, butadiene and acetylenic derivatives; a stream 2 of methanol fed to an etherifying unit 16 for etherifying the isobutene; a stream 3 of methyl-tert-butyl ether produced in the unit 3; a stream 4 substantially free from isobutene; a first distillation column 18 operated at about 14 atmospheres absolute; a top stream 5 essentially comprising isobutane; a residual stream 6 which is fed to a second distillation column 19 operated at a pressure of about 6 atmospheres absolute; a stream 8 containing heavy products; a hydrogenation unit 17 to which hydrogen is fed by a line 9 and to which the stream 7 is fed and from which is discharged a stream 11 essentially consisting of excess hydrogen and butene-1; and a hydrogenated stream 10 which is fed to a fractionation column 20 operated at a pressure of about 7 atmospheres absolute, from the top of which is obtained a stream 12 consisting of uncondensable matter and butene-1, from the tenth plate from the top of which is obtained a stream 13 of polymerization grade butene-1, and from the bottom of which is obtained a residue 14 substantially consisting of n-butane and butenes-2.

Stream 15 is the sum of the streams 5,8 and 14.

The operating parameters of the process are given in the following table, wherein the position numbers refer to those given in the drawing.

Position 1 4 5 6 7 8 9 kg/hr %wt kg/hr %wt kg/hr %wt kg/hr %wt kg/hr %wt kg/hr %wt kg/hr %wt H2 - - - - - - - - - - - - 6 100.0 C3 hydrocarbons 90 0.9 90 0.9 90 3.2 - - - - - - - Isobutane 2360 23.6 2360 24.5 2358 83.0 2 negl. 2 0.1 - - - - Isobutene 220 2.2 10 0.1 1 negl. 9 0.1 9 0.3 - - - Butene-1 3090 30.9 3075 3.91 367 12.9 2708 39.8 2705 91.8 3 0.1 - 1,3-Butadiene 70 0.7 70 0.7 6 0.2 64 0.9 64 2.2 - - - n-Butane 1730 17.3 1730 17.9 10 0.4 1720 25.3 152 5.2 1568 40.6 - trans-Butene-2 1430 14.3 1440 14.9 6 0.2 1434 21.1 12 0.4 1422 36.8 - cis-Butene-2 870 8.7 875 9.1 3 0.1 872 12.8 1 negl. 871 22.5 - C5 hydrocarbons 140 1.4 - - - - - - - - - - - TOTAL 10000 100.0 9650 100.0 2841 100.0 6809 100.0 2945 100.0 3684 100.0 6 100.0 Position 10 11 12 13 14 15 kg/hr %wt kg/hr %wt kg/hr %wt kg/hr %wt kg/hr %wt kg/hr %wt H2 1 negl. 3 6.8 1 2.0 - - - - - C3 Hydrocarbons - - - - - - - - - - 90 1.3 Isobutane 2 0.1 - - - - 2 0.1 - - 2358 33.3 Isobutene 9 0.3 - - - - 9 0.4 - - 1 negl.

Butene-1 2602 89.5 38 89.5 38 86.4 50 98.0 2462 99.0 90 24.3 460 6.5 1,3-Butadiene - 43ppm - - - - - 50ppm - - 6 0.1 n-Butane 183 6.3 2 4.5 - - 11 0.4 171 46.2 1749 24.7 trans-Butene-2 82 2.8 1 2.3 - - 2 0.1 81 21.9 1509 21.3 cis-Butene-2 28 1.0 - - - - - - 28 7.6 902 12.8 C5 Hydrocarbons - - - - - - - - - - - TOTAL 2907 100.0 44 100.0 51 100.0 2486 100.0 370 100.0 7075 100.0

Claims (6)

1. A process for the recovery of butene-1 from a C4 fraction which contains butene-1 and which is free or substantially free of isobutene, which process comprises (a) distilling the fraction in a first distillation column at a pressure of from 5 to 20 atmospheres absolute to obtain a head product comprising isobutane and a bottom product comprising residual components; (b) distilling the bottom product comprising residual components in a second distillation column at a pressure of from 3 to 10 atmospheres absolute to obtain a head product comprising butene-1 having a purity of from 80 to 95% and a bottom product comprising high boiling compounds (e.g. n-butane, cis-butene-2 and trans-butene-2); (c) subjecting the head product comprising butene-1 to selective hydrogenation so as to reduce the content of butadiene and acetylenic derivatives of the product to a value of from 30 to 200 ppm; and (d) feeding the product from the selective hydrogenation to a third distillation column, operting art a pressure of from 3 to 10 atmospheres absolute, so as to obtain butene-1 from the vicinity of the head of the column.
2. A process according to claim 1, wherein the C4 fraction comprises one or more hydrocarbons containing three carbon atoms, isobutane, n-butane, butene-1, cist-butene-2, trans-butene-2, one or more hydrocarbons containing five carbon atoms, butadiene, and one or more acetylenic compounds.
3. A process according to claim 2, wherein the C4 fraction is one obtained by the removal of isobutene from a C4 fraction comprising: C3 components 0.2-1.5% by weight isobutane 1-30% by weight isobutene 1(or 10)-130% by weight n-butane 3 to 20% by weight butene-1 10-40% by weight cis-butene-2 and trans-butene-2 . 8-30% by weight Cg components 0.1-1.0% by weight butadiene and acetylenic components 0.1-6% by weight.
4. A process according to claim 1, substantially as hereinbefore described with reference to the drawing.
5. Process for the recovery of polymerization grade butene-1 from a C4 fraction which contains it, free from isobutene or substantially free from isobutene, comprising the stages of to distill in a first distillation column, at a pressure comprised in the range from 5 to 20 abs. atm., such fraction, obtaining a top stream essentially containing isobutane and a bottom stream containing the residual components, and of to distill the stream containing the residual components, in a second distillation column, at a pressure comprised in the range from 3 to 10 abs. atm., obtaining a top stream of butene-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 hydrogenation unit being finally fed to a distillation column, operated at a pressure comprised within the range from 3 to 10 abs. atm., obtaining from a plate close to the top of the column, polymerization grade butene-1.
6. Butene-1 when recovered by a process according to any of claims 1 to 5.
GB08417309A 1983-07-28 1984-07-06 Process for the recovery of butene-1 Expired GB2144146B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
IT2229483A IT1194351B (en) 1983-07-28 1983-07-28 A process for the recovery of butene-1 polymerization grade

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GB8417309D0 GB8417309D0 (en) 1984-08-08
GB2144146A true GB2144146A (en) 1985-02-27
GB2144146B GB2144146B (en) 1987-02-18

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GB08417309A Expired GB2144146B (en) 1983-07-28 1984-07-06 Process for the recovery of butene-1

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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) ZA8405088B (en)

Cited By (15)

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US8319747B2 (en) 2008-12-11 2012-11-27 Apple Inc. Single layer touch panel with segmented drive and sense electrodes
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
US8593425B2 (en) 2009-04-10 2013-11-26 Apple Inc. Touch sensor panel design
US8633915B2 (en) 2007-10-04 2014-01-21 Apple Inc. Single-layer touch-sensitive display
US8957874B2 (en) 2009-06-29 2015-02-17 Apple Inc. Touch sensor panel design
US9261997B2 (en) 2009-02-02 2016-02-16 Apple Inc. Touch regions in diamond configuration
US9280251B2 (en) 2014-07-11 2016-03-08 Apple Inc. Funneled touch sensor routing
US9652088B2 (en) 2010-07-30 2017-05-16 Apple Inc. Fabrication of touch sensor panel using laser ablation
US9874975B2 (en) 2012-04-16 2018-01-23 Apple Inc. Reconstruction of original touch image from differential touch image
US9880655B2 (en) 2014-09-02 2018-01-30 Apple Inc. Method of disambiguating water from a finger touch on a touch sensor panel
US9886141B2 (en) 2013-08-16 2018-02-06 Apple Inc. Mutual and self capacitance touch measurements in touch panel
US9996175B2 (en) 2009-02-02 2018-06-12 Apple Inc. Switching circuitry for touch sensitive display
US10289251B2 (en) 2014-06-27 2019-05-14 Apple Inc. Reducing floating ground effects in pixelated self-capacitance touch screens
US10365773B2 (en) 2016-03-31 2019-07-30 Apple Inc. Flexible scan plan using coarse mutual capacitance and fully-guarded measurements

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003063281A (en) * 2001-08-29 2003-03-05 Sanwa Tekki Corp Trolly line hanger ear and insulation coupling element

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Publication number Priority date Publication date Assignee Title
DE1280845B (en) * 1965-10-29 1968-10-24 Huels Chemische Werke Ag A process for the selective hydrogenation of butadiene (1, 3) in a larger amounts of butene-1 and small amounts of butadiene (1, 3) containing C-hydrocarbon mixture
FR2474024B1 (en) * 1980-01-23 1984-09-21 Inst Francais Du Petrole
FR2493306B1 (en) * 1980-10-30 1983-12-23 Inst Francais Du Petrole
FR2495605B1 (en) * 1980-12-05 1984-09-28 Inst Francais Du Petrole
FR2508437B1 (en) * 1981-06-26 1983-11-18 Inst Francais Du Petrole
US4820472A (en) * 1981-07-14 1989-04-11 Westinghouse Electric Corp. Nuclear reactor spent fuel storage rack

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8633915B2 (en) 2007-10-04 2014-01-21 Apple Inc. Single-layer touch-sensitive display
US10331278B2 (en) 2007-10-04 2019-06-25 Apple Inc. Single-layer touch-sensitive display
US9317165B2 (en) 2007-10-04 2016-04-19 Apple Inc. Single layer touch-sensitive display
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
US9996175B2 (en) 2009-02-02 2018-06-12 Apple Inc. Switching circuitry for touch sensitive display
US9261997B2 (en) 2009-02-02 2016-02-16 Apple Inc. Touch regions in diamond configuration
US8982096B2 (en) 2009-04-10 2015-03-17 Apple, Inc. Touch sensor panel design
US8593425B2 (en) 2009-04-10 2013-11-26 Apple Inc. Touch sensor panel design
US8593410B2 (en) 2009-04-10 2013-11-26 Apple Inc. Touch sensor panel design
US10001888B2 (en) 2009-04-10 2018-06-19 Apple Inc. Touch sensor panel design
US9582131B2 (en) 2009-06-29 2017-02-28 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
US9874975B2 (en) 2012-04-16 2018-01-23 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
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
US10365773B2 (en) 2016-03-31 2019-07-30 Apple Inc. Flexible scan plan using coarse mutual capacitance and fully-guarded measurements

Also Published As

Publication number Publication date
PL248948A1 (en) 1985-04-24
PT78990A (en) 1984-08-01
ES534969D0 (en)
HUT36762A (en) 1985-10-28
GR82261B (en) 1984-12-13
DE3426349A1 (en) 1985-02-14
BE900248A (en) 1985-01-28
BR8403665A (en) 1985-07-02
SE8403426L (en) 1985-01-29
KR850001141A (en) 1985-03-16
IT1194351B (en) 1988-09-22
GB8417309D0 (en) 1984-08-08
CS250667B2 (en) 1987-05-14
BE900248A1 (en)
NL8402384A (en) 1985-02-18
DD222000A5 (en) 1985-05-08
AU561302B2 (en) 1987-05-07
ZA8405088B (en) 1985-02-27
DK369484D0 (en) 1984-07-27
PT78990B (en) 1986-10-23
KR870000583B1 (en) 1987-03-23
CA1232919A1 (en)
DK369484A (en) 1985-01-29
CA1232919A (en) 1988-02-16
ES534969A0 (en) 1985-08-16
ES8507007A1 (en) 1985-08-16
FR2549825B1 (en) 1987-01-09
SE8403426D0 (en) 1984-06-27
GB2144146B (en) 1987-02-18
AU3096084A (en) 1985-01-31
YU132184A (en) 1986-12-31
IT8322294D0 (en) 1983-07-28
JPS6051131A (en) 1985-03-22
RO90623A (en) 1986-12-10
LU85466A1 (en) 1985-04-17
TR22082A (en) 1986-03-17
NO843022L (en) 1985-01-29
FR2549825A1 (en) 1985-02-01

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