WO2014044693A1 - Verfahren zur herstellung von butadien mit entfernung von sauerstoff aus c4-kohlenwasserstoffströmen - Google Patents

Verfahren zur herstellung von butadien mit entfernung von sauerstoff aus c4-kohlenwasserstoffströmen Download PDF

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Publication number
WO2014044693A1
WO2014044693A1 PCT/EP2013/069329 EP2013069329W WO2014044693A1 WO 2014044693 A1 WO2014044693 A1 WO 2014044693A1 EP 2013069329 W EP2013069329 W EP 2013069329W WO 2014044693 A1 WO2014044693 A1 WO 2014044693A1
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Prior art keywords
stream
butane
butadiene
oxygen
gas
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Ceased
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PCT/EP2013/069329
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German (de)
English (en)
French (fr)
Inventor
Alireza REZAI
Gauthier Luc Maurice Averlant
Martin Dieterle
Godwin Tafara Peter Mabande
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BASF SE
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BASF SE
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Priority to EP13763254.3A priority Critical patent/EP2897927B1/de
Priority to CN201380060131.2A priority patent/CN104797547A/zh
Priority to KR1020157009687A priority patent/KR20150058355A/ko
Priority to JP2015532390A priority patent/JP2015530394A/ja
Priority to EA201590567A priority patent/EA201590567A1/ru
Publication of WO2014044693A1 publication Critical patent/WO2014044693A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
    • C07C5/333—Catalytic processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
    • B01J23/622—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead
    • B01J23/626—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead with tin
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    • B01J23/56—Platinum group metals
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J35/56—Foraminous structures having flow-through passages or channels, e.g. grids or three-dimensional monoliths
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    • C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
    • C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
    • C01B3/22—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by decomposition of gaseous or liquid organic compounds
    • C01B3/24—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by decomposition of gaseous or liquid organic compounds of hydrocarbons
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    • C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
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    • C07C7/00—Purification; Separation; Use of additives
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G70/00—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G70/00—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00
    • C10G70/02—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00 by hydrogenation
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    • C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
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    • C01B2203/0266—Processes for making hydrogen or synthesis gas containing a decomposition step
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    • C01B2203/0435—Catalytic purification
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    • C01B2203/0465—Composition of the impurity
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    • C01—INORGANIC CHEMISTRY
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    • C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
    • C01B2203/12—Feeding the process for making hydrogen or synthesis gas
    • C01B2203/1205—Composition of the feed
    • C01B2203/1211—Organic compounds or organic mixtures used in the process for making hydrogen or synthesis gas
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    • C01B2203/1247—Higher hydrocarbons
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    • 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
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    • C07C2521/08—Silica
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    • 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
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    • 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
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    • 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
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    • C07C2523/32—Manganese, technetium or rhenium
    • C07C2523/34—Manganese
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    • C07C2523/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
    • C07C2523/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/85—Chromium, molybdenum or tungsten
    • C07C2523/88—Molybdenum
    • C07C2523/887—Molybdenum containing in addition other metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/14—Phosphorus; Compounds thereof
    • C07C2527/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2527/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
    • C07C2527/19—Molybdenum
    • C07C2527/192—Molybdenum with bismuth
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F23—COMBUSTION APPARATUS; COMBUSTION PROCESSES
    • F23C—METHODS OR APPARATUS FOR COMBUSTION USING FLUID FUEL OR SOLID FUEL SUSPENDED IN  A CARRIER GAS OR AIR 
    • F23C2900/00—Special features of, or arrangements for combustion apparatus using fluid fuels or solid fuels suspended in air; Combustion processes therefor
    • F23C2900/9901—Combustion process using hydrogen, hydrogen peroxide water or brown gas as fuel

Definitions

  • the oxidic support material is preferably selected from oxides of the metals of the second, third and fourth main group and the third and fourth transition group.
  • the support material is particularly preferably selected from oxides of magnesium, calcium, aluminum, silicon, titanium and zirconium or mixtures thereof, in particular of silicon dioxide (S1O2) and / or zirconium dioxide (Zr02).
  • the monolith is preferably constructed of cordierite.
  • the stream 11 is wholly or partially recycled to the stage K).
  • Suitable selective solvents for the process according to the invention are, for example, butyrolactone, nitriles such as acetonitrile, propionitrile, methoxypropionitrile, ketones such as acetone, furfurol, N-alkyl-substituted lower aliphatic acid amides such as dimethylformamide, diethylformamide, dimethylacetamide, diethylacetamide, N-formylmorpholine, N-alkyl-substituted cyclic Acid amides (lactams) such as N-alkylpyrrolidones, in particular N-methylpyrrolidone.
  • nitriles such as acetonitrile, propionitrile, methoxypropionitrile
  • ketones such as acetone, furfurol
  • N-alkyl-substituted lower aliphatic acid amides such as dimethylformamide, diethylformamide, dimethylacetamide, dieth
  • the butane-containing gas stream (2) to be dehydrogenated is preferably introduced into the heat exchanger (12) at two or more points, preferably as a main stream with a higher mass flow and one or more secondary streams with a lower mass flow in relation to the main stream.
  • each catalytically active zone (5) which are arranged in front of each catalytically active zone (5), provided, which can be provided as additional heating, an electric heater (22), which is preferably releasably introduced as plug-in system, within the O . Schemes B of the reactor (1) , or as a muffle burner (22), in the supply line (7) for the butane gas stream to be dehydrogenated (2) after the exit thereof from the heat exchanger (12).
  • the product gas stream leaving the oxidative dehydrogenation comprises g 2 to 40% by volume of butadiene, 5 to 80% by volume of n-butane, 0 to 15% by volume of 2-butenes, 0 to 5% by volume of 1-butene , 5 to 70% by volume of steam, 0 to 10% by volume of low-boiling hydrocarbons (methane, ethane, ethene, propane and propene), 0.1 to 15% by volume of hydrogen, 0 to 70% by volume of inert gas , 0 to 10% by volume of carbon oxides, 0 to 10% by volume of oxygen and 0 to 10% by volume of oxygenates, the total amount of the ingredients being 100% by volume.
  • Unstabilized 1,3-butadiene can form dangerous butadiene peroxides in the presence of oxygen.
  • the peroxides are viscous liquids. Their density is higher than that of butadiene. Moreover, since they are only slightly soluble in liquid 1,3-butadiene, they settle on the bottoms of storage containers. Despite their relatively low chemical reactivity, the peroxides are very unstable compounds that can spontaneously decompose at temperatures between 85 and 110 ° C. A particular danger is the high impact sensitivity of the peroxides, which explode with the explosiveness of an explosive. The danger of polymer formation is given especially in the distillative removal of butadiene (steps L and M) and can there lead to deposits of polymers (formation of so-called "popcorn") in the columns.
  • the gas stream h is preferably first cooled.
  • the cooling of the compressed gas is carried out with heat exchangers, which may for example be designed as a tube bundle, spiral or plate heat exchanger.
  • the dissipated heat is preferably used for heat integration in the process.
  • water is separated from the product stream.
  • the separation of the water is preferably carried out in a quench.
  • the quench also serves to separate oxygen-containing by-products.
  • the loaded with C 4 hydrocarbons solvent stream is passed into a desorption column.
  • the desorption step is carried out by relaxation and / or heating of the loaded solvent.
  • the preferred process variant is the addition of stripping steam and / or the supply of live steam in the bottom of the desorber.
  • the C 4 -depleted solvent may be fed as a mixture together with the condensed vapor (water) to a phase separation, so that the water is separated from the solvent. All apparatuses known to the person skilled in the art are suitable for this purpose. It is also possible to use the separated water from the solvent to produce the stripping steam. Preference is given to 70 to 100% by weight of solvent and 0 to 30% by weight.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
PCT/EP2013/069329 2012-09-20 2013-09-18 Verfahren zur herstellung von butadien mit entfernung von sauerstoff aus c4-kohlenwasserstoffströmen Ceased WO2014044693A1 (de)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP13763254.3A EP2897927B1 (de) 2012-09-20 2013-09-18 Verfahren zur herstellung von butadien mit entfernung von sauerstoff aus c4-kohlenwasserstoffströmen
CN201380060131.2A CN104797547A (zh) 2012-09-20 2013-09-18 从c4-烃物流中除去氧气的制备丁二烯的方法
KR1020157009687A KR20150058355A (ko) 2012-09-20 2013-09-18 C₄ 탄화수소 스트림으로부터 산소의 제거에 의한 부타디엔의 제조 방법
JP2015532390A JP2015530394A (ja) 2012-09-20 2013-09-18 Ｃ４炭化水素流からの酸素の除去によるブタジエンの製造方法
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EP2945923B1 (de) * 2013-01-15 2017-03-15 Basf Se Verfahren zur oxidativen dehydrierung von n-butenen zu butadien
RU2788907C1 (ru) * 2020-12-22 2023-01-25 Юоп Ллк Способ и устройство дегидрирования парафинов

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JP2019501938A (ja) * 2016-01-13 2019-01-24 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 酸化的脱水素化によるｎ−ブテンからの１，３−ブタジエンの製造方法
JP7064897B2 (ja) * 2018-02-15 2022-05-11 Ｅｎｅｏｓ株式会社 不飽和炭化水素の製造方法
JP7064896B2 (ja) * 2018-02-15 2022-05-11 Ｅｎｅｏｓ株式会社 不飽和炭化水素の製造方法
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EP2945923B1 (de) * 2013-01-15 2017-03-15 Basf Se Verfahren zur oxidativen dehydrierung von n-butenen zu butadien
WO2016083135A1 (de) * 2014-11-28 2016-06-02 Wacker Chemie Ag Entfernung von sauerstoff aus kohlenwasserstoffgasen
RU2788907C1 (ru) * 2020-12-22 2023-01-25 Юоп Ллк Способ и устройство дегидрирования парафинов

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