EP1856018A2 - Procede de production de propene a partir de courants d'alimentation riches en 2-butene et en isobutene - Google Patents

Procede de production de propene a partir de courants d'alimentation riches en 2-butene et en isobutene

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Publication number
EP1856018A2
EP1856018A2 EP06724887A EP06724887A EP1856018A2 EP 1856018 A2 EP1856018 A2 EP 1856018A2 EP 06724887 A EP06724887 A EP 06724887A EP 06724887 A EP06724887 A EP 06724887A EP 1856018 A2 EP1856018 A2 EP 1856018A2
Authority
EP
European Patent Office
Prior art keywords
stream
weight
butene
isobutene
metathesis
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.)
Withdrawn
Application number
EP06724887A
Other languages
German (de)
English (en)
Inventor
Marcus Sigl
Markus Schubert
Jürgen STEPHAN
Frank Poplow
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1856018A2 publication Critical patent/EP1856018A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/02—Alkenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/02—Alkenes
    • C07C11/06—Propene
    • 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
    • C07C11/09—Isobutene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
    • C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • C07C2521/04—Alumina
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/24—Chromium, molybdenum or tungsten
    • C07C2523/30—Tungsten
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/32—Manganese, technetium or rhenium
    • C07C2523/36—Rhenium
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/40—Ethylene production

Definitions

  • the present invention relates to a one-step process for the preparation of propene by the ethenolysis of a 2-butene and isobutene-containing stream.
  • catalysts based on MoO 3 , CoO-MoO 3 , MoS 2 , Mo (CO) 6 or various supported Mo complexes can be used at even higher temperatures of up to 540 0 C also systems based on WO 3 , WS 2 , W (CO) 6 or supported W complexes (Mol, J. C, Chapt 4.12.2 "alkenes metathesis" in “Handbook of Heterogeneous Catalysis”, Eds. Ertl, G., Knözinger, H., Weitkamp, J., VCH, Weinheim 1997; Weissermehl, K., Arpe, H.-J., Chapt.
  • SiO 2 and / or Al 2 O 3 -supported tungsten oxides are preferably suitable for the person skilled in the art for the metathesis at higher temperatures.
  • Substance stream (stream C 5 ), and possibly another hydrocarbon-containing material stream (stream C x ), possibly consisting of several separate streams.
  • the feed stream preferably contains
  • the feed stream is provided by either of the two methods comprising steps Ia and IIa and steps Ib and IIb, respectively.
  • steps Ia and IIa the procedure is followed
  • step Ia subjecting naphtha or other hydrocarbon compounds to a steam cracking or FCC process in step Ia and removing a C 4 -olefin mixture from the resulting material stream, the isobutene, 2-butene, and butadiene and optionally butine and, if appropriate, Contains 1-butene and
  • a C 4 -Kohlen- hydrogen stream (raffinate I) consisting essentially of, isobutene, 2-butenes and optionally butanes and optionally 1-butene prepared by means of Selective hydrogenation the butadienes and butynes hydrogenated to butenes or butanes or the butadienes and butynes by extractive distillation far removed so that the content of 1, 3-butadiene maximum 1000 ppm by weight.
  • step Ib) in step Ib from a butane-containing hydrocarbon stream by dehydration and subsequent purification produces a C 4 olefin mixture containing isobutene, 2-butenes, and butadienes and optionally butynes, optionally 1-butene, and optionally butanes
  • a C4 hydrocarbon stream consisting essentially of isobutene, 2-butenes and optionally butanes and optionally 1-butene is prepared by selectively adding the butadienes and Butene hydrogenated to butenes or butanes or the butadienes and butynes removed by extractive distillation far enough so that the content of 1, 3-butadiene is at most 1000 ppm by weight.
  • the corresponding hydrocarbon is evaporated and in the Gas phase contacted with a catalyst at a temperature of 450 to 500 0 C in contact.
  • the particulate catalyst is fluidized by the countercurrent hydrocarbon stream.
  • the catalyst used is usually synthetic crystalline zeolites.
  • the substep selective hydrogenation in the liquid phase over a metal selected from the group nickel, palladium and platinum, on a support, preferably palladium on alumina, at a temperature of 20 to 200 0 C, a pressure of 1 to 50 bar, a Volume speed of 0.5 to 30 m 3 Frischfeed per m 3 of catalyst per hour and a ratio of recycle to feed of 0 to 30 with a molar ratio of hydrogen to diolefins of 0.5 to 50 carried out.
  • a metal selected from the group nickel, palladium and platinum, on a support, preferably palladium on alumina, at a temperature of 20 to 200 0 C, a pressure of 1 to 50 bar, a Volume speed of 0.5 to 30 m 3 Frischfeed per m 3 of catalyst per hour and a ratio of recycle to feed of 0 to 30 with a molar ratio of hydrogen to diolefins of 0.5 to 50 carried out.
  • a butadiene extraction is carried out from the C 4 olefin mixture with a butadiene-selective solvent selected from the class of polar aprotic solvents, such as acetone, furfural, acetonitrile, dimethylacetamide, dimethylformamide and N-methylpyrrolidone.
  • a butadiene-selective solvent selected from the class of polar aprotic solvents, such as acetone, furfural, acetonitrile, dimethylacetamide, dimethylformamide and N-methylpyrrolidone.
  • Particularly preferred is a combination of extractive distillation and selective hydrogenation, wherein, if the content of 1, 3-butadiene in the obtained in step Ia or step Ib C 4 olefin mixture is 5 wt .-% or more, the content of 1 , 3-butadiene by means of extractive distillation to a content between 1000 ppm by weight and 5 wt .-% and lower the content of 1, 3-butadiene then selectively by means of selective hydrogenation to 1000 ppm by weight or less.
  • the content of 1-butene in the feed stream is lowered to the content defined by passing the 1-butene in the C 4 -olefin mixture or raffinate I.
  • Hydroisomerization largely converts to 2-butene or preferably in a hydroformylation reaction to valeraldehyde largely selectively reacted and the valeraldehyde is separated.
  • the hydroformylation reaction can generally be carried out in a manner conventional and familiar to the person skilled in the art.
  • a good overview with numerous other references can be found for example in M. Beller et al., Journal of Molecular Catalysis A, 104, 1995, pages 17 to 85 or in Ullmann's Encyclopedia of Industrial Chemistry, 6 th edition, 2000 electronic release, Chapter " ALDEHYDES, ALIPHATIC AND ARALIPHATIC - Saturated Aldehydes ".
  • transition metal is preferably prepared from 1-butene with the addition of synthesis gas (CO: H 2 from 3: 1 to 1: 3, preferably 1, 5: 1 to 1: 1, 15) Valeraldehyd (n-pentanal).
  • rhodium complexes are usually used with phosphorus-containing ligands. Typically this is in the phosphorus-containing ligands to a mono- or di-phosphine, preferably a triarylphosphine, particularly preferably triphenylphosphine.
  • the hydroformylation reaction is carried out usually at temperatures of 50 to 150 0 C, preferably from 70 to 120 0 C and pressures of 5 to 50 bar, preferably 10 to 30 bar.
  • the content of isobutene in the feed stream or in the raffinate I can be reduced by known methods to the respectively desired values.
  • the distillation takes place in a suitable apparatus, e.g. a bubble tray column, packed column, packed column or dividing wall column.
  • a suitable apparatus e.g. a bubble tray column, packed column, packed column or dividing wall column.
  • the distillation column is designed with 20 to 80 theoretical plates.
  • the reflux ratio is generally 5 to 50.
  • the distillation is generally carried out at a pressure of 5 to 20 bar.
  • the top stream will mainly be isobutene and 1-butene
  • the bottom stream will mainly contain 2-butenes and n-butane.
  • the content of low boilers (isobutene and 1-butene) in the bottom stream is less than 40%, preferably less than 30% and particularly preferably 5 to 20%.
  • the content of high boilers (2-butenes and n-butane) in the top stream is less than 40%, preferably less than 30% and particularly preferably 5 to 20%.
  • the usual procedure is to bring the feed stream or raffinate I into contact with an alkyl alcohol, preferably a C 1 -C 4 -alkyl alcohol and a conventional catalyst for the formation of alkyl tert-butyl ether, and to form the Separates alkyl tert-butyl ether.
  • alkyl alcohol preferably a C 1 -C 4 -alkyl alcohol and a conventional catalyst for the formation of alkyl tert-butyl ether, and to form the Separates alkyl tert-butyl ether.
  • Particularly preferred alcohols are methanol and butanols.
  • the etherification is preferably carried out in the presence of an acidic ion exchanger in a three-stage reactor cascade in which flooded fixed bed catalysts are flowed through from top to bottom, wherein the reactor inlet temperature 0 to 60 0 C, preferably 10 to 50 0 C, the starting temperature 25 to 85 ° C. , preferably 35 to 75 ° C, the pressure 2 to 50 bar, preferably 3 to 20 bar and the ratio of alcohol to isobutene 0.8 to 2.0, preferably 1, 0 to 1, 5.
  • the usual procedure is to bring the feed stream or raffinate I into contact with a customary catalyst for the polymerization of isobutene and to remove the polyisobutene formed from the remaining feed stream or raffinate. separates.
  • the catalyst used is preferably a homogeneous or heterogeneous catalyst from the class of Bronsted or Lewis acids.
  • the catalyst is preferably boron trifluoride or aluminum trichloride.
  • the oligomerization of isobutene (method d) is carried out under proton catalysis at temperatures between 50 and 15O 0 C and pressures between 10 and 40 bar.
  • the catalysts used are preferably sulfuric acid or acidic ion exchangers.
  • Main products are dimers, trimers to a lesser extent and higher oligomers by-products.
  • oxygenates for example water, acetone or ethanol
  • diolefins should be less than 300 ppm by weight, preferably less than 150 ppm by weight, more preferably less than 100 ppm by weight.
  • allene, 1,2-butadiene or propadiene are strong feed poisons for metathesis catalysts and should be less than 15 ppm by weight, preferably less than 10 ppm by weight, very particularly preferably less than 5 ppm by weight.
  • the purification of the C 4 stream consists of one or more stages and can also contain pressure swing processes (pressure swing adsorption), but at least one adsorptive process is preferred.
  • the purification preferably takes place immediately before the metathesis stage.
  • the purification step may also comprise a selective hydrogenation which still removes residual traces of diolefins which have not been fully hydrogenated in the first selective hydrogenation stage or may have newly formed in later stages of the process, for example in an isomerization.
  • the purification stage preferably contains at least one adsorbent bed based on an aluminum oxide or a molecular sieve for the removal of oxygenates. Particularly preferred is an embodiment in which at least two adsorbent beds are contained based on an alumina or molecular sieve, which are each alternately in the adsorption or Regeneriermodus. Preferred adsorbents are a 13X molecular sieve or high surface area gamma aluminas).
  • Rhenium-containing catalysts which are operated at temperatures in the range from 0 to 150 ° C., preferably in the range from 35 to 110 ° C.
  • W-containing, re-free Catalysts which are operated in the gas phase at temperatures of 200 to 600 0 C, preferably from 220 to 450 0 C.
  • the Re-containing catalysts preferably contain at least 1 wt .-% Re in oxidic form on a support which consists of at least 75 wt .-% of a high-surface area alumina, most preferably gamma-alumina exists. Particular preference is given to catalysts which have a Re content of between 5 and 12% by weight and are supported on pure gamma Al 2 O 3 .
  • the catalysts may also contain dopants to increase the activity, for example, oxides of Nb, Ta, Zr, Ti, Fe, Mn, Si, Mo, W, phosphate or sulfate.
  • the catalysts have surfaces of at least 50 m 2 / g, preferably at least 100 m 2 / g, and a pore volume of at least 0.3 ml / g, preferably at least 0.4 ml / g.
  • Suitable Re-containing catalysts are described, for example, in DE-A-102004009804, DE-A-102004009805 or DE-A-102004009803.
  • Suitable W-containing, free catalysts preferably contain at least 3 wt .-% W, at least partially in oxidic form, on a support selected from the group aluminum oxides, aluminosilicates, zeolites or, preferably SiO 2 .
  • the catalysts preferably have a surface area of at least 50 m 2 / g and a pore volume of at least 0.3 ml / g, more preferably at least 0.5 ml / g.
  • the activity or isomerization activity can be modified by suitable doping, for example alkali metal and alkaline earth metal compounds, TiO 2 , ZrO 2 , HfO 2 , or compounds or elements from the group Ag, Sb, Mn, W, Mo, Zn, Si.
  • suitable doping for example alkali metal and alkaline earth metal compounds, TiO 2 , ZrO 2 , HfO 2 , or compounds or elements from the group Ag, Sb, Mn, W, Mo, Zn, Si.
  • the separation can be carried out so that from the product stream, in addition to unreacted ethene, 2-butene, isobutene and optionally 1-butene now also the products 2-methyl-2-butene and propene, and optionally further C 5 and C 6 olefins, contains, in the first workup step first ethene separated overhead and returned to the metathesis.
  • propene in "polymer grade" purity is removed overhead, and finally, in the last column, a top stream having an isobutene content of at least 70% by weight is preferred more than 80 wt .-% separated and can be recycled.
  • the sump consisting mainly of 2-butene, 2-methyl-2-butene and optionally other C 5 - and C 6 -olefins is recycled to the metathesis reaction.
  • the removal of a C 4 purge stream is usually required in the third column.
  • B. double bond isomerization or dimerization and higher olefins with 7 or more carbon atoms form (C 7+ ).
  • an additional purge stream C 7+ can optionally be taken.
  • This purge stream C 7+ is preferably withdrawn at the bottom of the column, on which the butane purge is also carried out. For clarity, this embodiment is shown in drawing 1.
  • the separation can be carried out so that from the product stream, in addition to unreacted ethene, 2-butene, isobutene and optionally 1-butene now also the products 2-methyl-2-butene and propene, and optionally further C 5 and C 6 olefins, contains, in the first workup step, first ethene is separated off together with propene and isobutene overhead, and the bottom, consisting mainly of 2-butene, 2-methyl-2-butene and optionally further C 5 - and C 6 - olefins is recycled to the metathesis. In a second stage ethene is separated overhead and returned to the metathesis stage.
  • a 2-butene-rich feed is fed to a metathesis stage to convert the 2-butene to the higher-valent monomer propene.
  • An important aspect of the process according to the invention is that although isobutene present in the feed stream and optionally residues of 1-butene also partially react to form higher olefins (C 5 and C 6 ), these become at least after distillative separation of the product stream partially fed back to the metathesis, from them isobutene is formed for the most part, so that no or only a small net sales arises. Losses thus occur mainly by purge streams, with which the enrichment of the feed stream with compounds such as n-butane or i-butane or possibly resulting high boilers (C 7 + ) is prevented.
  • higher olefins preferably accumulate at most in an amount of 20 mol%, based on the propene, more preferably in an amount of at most 10 mol%, and most preferably in an amount of at most 5 mol%.
  • a 2-butenes and isobutene-rich stream is reacted in the liquid phase on a fixed bed catalyst, 10% by weight of Re 2 O 7 on gamma Al 2 O 3 .
  • Ethene consisting of fresh ethene and recycle ethene, is added stoichiometrically to the C 4 content.
  • the temperature is gradually raised during the reaction within one to two weeks from 35 to 120 0 C.
  • the reaction pressure is 35 bar.
  • the catalyst must be regenerated oxidatively.
  • a parallel-connected reactor (A / B mode) can take over production.
  • a 2-butene and isobutene-rich stream is reacted in the gas phase on a fixed bed catalyst, 10 wt .-% WO 3 on SiO 2 .
  • Ethene consisting of fresh ethene and recycle ethene, is added stoichiometrically to the C 4 content.
  • the temperature is gradually raised during the reaction from 230 to 430 0 C within a few weeks. Thereafter, the catalyst must be regenerated oxidatively.
  • a parallel-connected reactor (A / B mode) can take over production.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Procédé de production d'un courant de produit essentiellement formé d'éthène (courant C2= ), d'un courant de produit essentiellement formé de propène (courant C3=), d'un courant de produit essentiellement formé d'isobutène et, éventuellement, d'autres oléfines à 4 atomes de carbone (courant C4= ) et d'un courant de produit essentiellement formé de 2-méthyl-2-butène et, éventuellement, de 2-butène (courant C5=) et, éventuellement, d'un autre courant de produit contenant d'autres hydrocarbures (courant Cx), formé éventuellement de plusieurs courants partiels séparés, procédé caractérisé en ce qu'il comprend une étape de métathèse dans laquelle on met en contact un courant d'hydrocarbures en C4 renfermant au moins 15 % en poids de 2-butène, au moins 5 % en poids d'isobutène, et pas plus de 5 % en poids de 1-butène (courant d'alimentation) avec de l'éthène, en présence d'un catalyseur usuel de métathèse, et en ce que le courant d'hydrocarbures ainsi formé est séparé dans les courants C2=, C3=, C4= et éventuellement Cx et en ce que le courant C5= est recyclé en totalité ou en partie dans l'étape de méthathèse.
EP06724887A 2005-02-28 2006-02-24 Procede de production de propene a partir de courants d'alimentation riches en 2-butene et en isobutene Withdrawn EP1856018A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005009665A DE102005009665A1 (de) 2005-02-28 2005-02-28 Verfahren zur Herstellung von Propen aus 2-Buten- und Isobuten-reichen Feedströmen
PCT/EP2006/060275 WO2006089956A2 (fr) 2005-02-28 2006-02-24 Procede de production de propene a partir de courants d'alimentation riches en 2-butene et en isobutene

Publications (1)

Publication Number Publication Date
EP1856018A2 true EP1856018A2 (fr) 2007-11-21

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EP06724887A Withdrawn EP1856018A2 (fr) 2005-02-28 2006-02-24 Procede de production de propene a partir de courants d'alimentation riches en 2-butene et en isobutene

Country Status (9)

Country Link
US (1) US20080200745A1 (fr)
EP (1) EP1856018A2 (fr)
JP (1) JP2008531643A (fr)
KR (1) KR20070107069A (fr)
CN (1) CN101128408A (fr)
CA (1) CA2598322A1 (fr)
DE (1) DE102005009665A1 (fr)
MX (1) MX2007010286A (fr)
WO (1) WO2006089956A2 (fr)

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CN102070389A (zh) * 2011-01-12 2011-05-25 王伟跃 利用炼厂副产物制丙烯的工艺
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CN106795442B (zh) * 2014-10-09 2019-04-02 巴斯夫欧洲公司 提纯有机组合物的方法
ES2826406T3 (es) * 2014-10-09 2021-05-18 Basf Se Proceso de regeneración de un adsorbedor
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WO2016071268A1 (fr) 2014-11-03 2016-05-12 Basf Se Procédé de préparation de 1,3-butadiène à partir de n-butènes par déshydrogénation oxydative
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Also Published As

Publication number Publication date
WO2006089956A2 (fr) 2006-08-31
MX2007010286A (es) 2008-04-10
WO2006089956A3 (fr) 2007-03-08
CA2598322A1 (fr) 2006-08-31
US20080200745A1 (en) 2008-08-21
JP2008531643A (ja) 2008-08-14
DE102005009665A1 (de) 2006-08-31
CN101128408A (zh) 2008-02-20
KR20070107069A (ko) 2007-11-06

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