WO2008062709A1 - Procédé destiné à produire de l'éthylène - Google Patents

Procédé destiné à produire de l'éthylène Download PDF

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Publication number
WO2008062709A1
WO2008062709A1 PCT/JP2007/072180 JP2007072180W WO2008062709A1 WO 2008062709 A1 WO2008062709 A1 WO 2008062709A1 JP 2007072180 W JP2007072180 W JP 2007072180W WO 2008062709 A1 WO2008062709 A1 WO 2008062709A1
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WO
WIPO (PCT)
Prior art keywords
ethanol
ethylene
producing ethylene
producing
less
Prior art date
Application number
PCT/JP2007/072180
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English (en)
Japanese (ja)
Inventor
Michiaki Umeno
Toshihiro Takai
Original Assignee
Mitsui Chemicals, Inc.
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 Mitsui Chemicals, Inc. filed Critical Mitsui Chemicals, Inc.
Publication of WO2008062709A1 publication Critical patent/WO2008062709A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water

Definitions

  • the present invention relates to a method for producing high-purity ethylene by converting ethanol at a high conversion rate by a dehydration reaction of ethanol.
  • Ethylene is a compound useful as a raw material for various low-molecular compounds and high-molecular compounds.
  • naphtha cracker-derived materials are used as raw materials for various polymers.
  • the production of ethylene from coal, natural gas or biomass-derived raw materials has been studied from the viewpoint of the problems of oil resource reduction that has been pointed out in the past and environmental problems in recent years.
  • a method for producing ethylene by dehydration reaction of a lower alcohol such as methanol or ethanol or a lower aliphatic ether such as dimethyl ether is expected as a relatively simple and useful production method.
  • Patent Document 1 and Patent Document 2 describe a method for producing lower olefin by dehydration reaction of alcohol.
  • methanol is used as a raw alcohol, and the obtained olefin is also ethylene. The content is not so high!
  • Patent Document 3 describes a method for producing ethylene by dehydration of ethanol. Although the conversion rate is relatively high, it cannot be said that the amount of other olefins produced is small. Yield was also satisfactory!
  • Patent Document 1 JP-A-58-146516
  • Patent Document 2 USP5914433
  • Patent Document 3 Japanese Patent Laid-Open No. 1 233236
  • the present invention uses ethanol as a raw material, and converts ethanol at a high conversion rate to achieve a high purity. It is an object of the present invention to provide a method for producing tylene with a high yield.
  • the present inventors have adjusted the amount of water contained in the raw material ethanol, so that ethanol is converted at a high conversion rate, and high-purity ethylene is obtained at a high yield. We found that it can be obtained at a rate.
  • the present invention includes, for example, the following items
  • a method for producing ethylene characterized by subjecting ethanol containing water in an amount of not less than lwt% to not more than 50 wt% to a dehydration reaction.
  • ethylene can be converted at a high conversion rate and high-purity ethylene can be produced in a high yield.
  • High quality ethylene can be produced.
  • ethylene purity is high, it is particularly useful for adjusting the supply and demand balance of lower olefins.
  • biomass-derived materials are used as raw material ethanol, it is extremely useful for the carbon dioxide balance in the environment, and if its derivatives or polymers are produced from the obtained ethylene, the contribution to the global environment is tremendous. is there.
  • the present invention is described in detail below.
  • the ethanol used as a raw material in the present invention may be synthetic ethanol derived from naphtha, fermented ethanol derived from biomass, etc.!
  • Fermented ethanol derived from a biomass refers to ethanol obtained by bringing a microorganism that produces ethanol or a product derived from its crushed material into contact with a culture solution containing a carbon source obtained from a plant, and purifying ethanol obtained from the product. Point to. Purification of ethanol from the culture solution can be achieved by adding conventional methods such as distillation, membrane separation, and extraction. Use a force S to remove moisture by touching with S.
  • a force S is usually used, and this catalyst is not particularly limited, and a known catalyst can be used.
  • a known catalyst can be used.
  • Advantageous in the process is a fixed bed flow reaction in which the catalyst and the product can be easily separated.
  • ⁇ -alumina is preferable as the catalyst in this case, but other known catalysts can be used.
  • this dehydration reaction is an endothermic reaction, it is usually carried out under heating conditions.
  • the reaction temperature is not particularly limited as long as the reaction proceeds at a commercially useful reaction rate, but a temperature of 100 ° C or higher, preferably 250 ° C or higher, more preferably 300 ° C or higher is appropriate.
  • the upper limit is not particularly limited, but it is 500 ° C or less, preferably 400 ° C or less, in terms of energy balance and equipment.
  • reaction pressure is not particularly limited, but a pressure equal to or higher than normal pressure is preferable in order to facilitate subsequent gas-liquid separation.
  • a fixed bed flow reaction in which separation of the catalyst is easy industrially is preferable, but a liquid phase suspension bed, a fluidized bed, etc. may be used.
  • the most important is the amount of water contained in ethanol supplied as a raw material.
  • the water content is low in view of water removal efficiency.
  • the lower limit of the water content in ethanol is 0.1 lwt% or more, preferably 1wt% or more, more preferably 3wt% or more, and particularly preferably 5wt% or more.
  • the upper limit is not particularly limited, but is 50 wt% or less, preferably 30 wt% or less, more preferably 20 wt% or less, and particularly preferably 10 wt% or less in terms of mass balance and heat balance.
  • Ethylene obtained by gas-liquid separation is further distilled.
  • the distillation method There are no particular restrictions on the distillation method, operating temperature, residence time, etc., except that the operating pressure at this time is not less than normal pressure.
  • the obtained ethylene contains carbonyl compounds such as ketones, aldehydes, and esters, which are impurities mixed in the ethanol fermentation process, and carbon dioxide gas, which is a decomposition product thereof, or an enzyme.
  • Decomposition product of the product contains a trace amount of nitrogen-containing compounds such as amines and amino acids and ammonia and the decomposition product.
  • these trace amounts of impurities may cause a problem and may be removed by purification.
  • Purification may be performed by any known method, but a suitable purification operation includes an adsorption purification method.
  • the adsorbent to be used is not particularly limited, but the type of adsorbent that is preferred for high surface area materials is selected according to the type of impurities in the ethylene obtained by dehydration of biomass-derived ethanol. .
  • caustic water treatment may be used in combination.
  • the conversion rate of ethanol is preferably 99.0% or more, more preferably 99.5% or more, and particularly preferably 99.8% or more.
  • the ethylene yield is preferably 97.0% or more, more preferably 98.0% or more, and particularly preferably 98.4% or more.
  • Ethylene obtained by the method of the present invention, or poly produced using the ethylene as a raw material The ability of polymers such as propylene to use biomass feedstock is determined by measuring the content of carbon with mass 14 and the content of carbon with mass 12 or mass 13 with force S.
  • the CO obtained by burning the sample is absorbed with a CO absorbent or converted to benzene, and the amount of carbon having a mass number of 14 is measured with a liquid scintillation counter. By comparing, it will be half IJ additional.
  • Example 1 The same operation as in Example 1 was carried out except that biomass-derived ethanol that had been purified by distillation and adjusted to a water content of 8 wt% was used. The results are shown in Table 1.
  • Example 1 99.95 98.75 0.09 0.8 0.3 0.01
  • Example 2 99.80 98.48 0.09 0.9 0.3 0.03
  • Comparative Example 1 99.96 95.70 0.04 3.9 0.3 0.02 (%)

Landscapes

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

Abstract

L'invention concerne un procédé destiné à produire un éthylène de pureté élevée avec un rythme de production et un rendement élevés, utilisant un éthanol en tant que matière première. Ce procédé destiné à produire un éthylène est caractérisé en ce qu'il consiste à déshydrater un éthanol possédant une teneur en eau supérieure à 0,1 % en poids. La température de la réaction de déshydratation n'est de préférence pas inférieure à 250 ˚C. L'éthanol est de préférence dérivé d'une biomasse.
PCT/JP2007/072180 2006-11-21 2007-11-15 Procédé destiné à produire de l'éthylène WO2008062709A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006-313770 2006-11-21
JP2006313770A JP2010030902A (ja) 2006-11-21 2006-11-21 エチレンの製造方法

Publications (1)

Publication Number Publication Date
WO2008062709A1 true WO2008062709A1 (fr) 2008-05-29

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PCT/JP2007/072180 WO2008062709A1 (fr) 2006-11-21 2007-11-15 Procédé destiné à produire de l'éthylène

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JP (1) JP2010030902A (fr)
WO (1) WO2008062709A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010158236A (ja) * 2008-12-09 2010-07-22 Naoshi Monma もやし生育システム及び該システムにより育成されたもやし
EP2365989A1 (fr) * 2008-11-13 2011-09-21 Arkema France Fabrication de copolymeres ethylene/acide carboxylique a partir de matieres renouvelables, copolymeres obtenus et utilisations
JP2013060514A (ja) * 2011-09-13 2013-04-04 Sekisui Plastics Co Ltd ポリエチレン系樹脂発泡粒子、ポリエチレン系樹脂発泡成形体及びポリエチレン系樹脂発泡粒子の製造方法
JP2016150931A (ja) * 2015-02-19 2016-08-22 出光興産株式会社 軽質オレフィンの製造方法

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2594547A1 (fr) * 2011-11-17 2013-05-22 Solvay Sa Processus de fabrication d'au moins un composé de dérivé d'éthylène à partir de bioéthanol
FR2984311B1 (fr) * 2011-12-20 2015-01-30 IFP Energies Nouvelles Procede de production d'octenes mettant en oeuvre la dimerisation de l'ethylene en butenes et la dimerisation des butenes en octenes
JP6301952B2 (ja) * 2012-12-13 2018-03-28 トタル リサーチ アンド テクノロジー フエリユイ エチレン流から軽質成分を除去する方法
JP6059005B2 (ja) * 2012-12-26 2017-01-11 株式会社クレハ 植物由来の塩化ビニリデン共重合体組成物及び熱収縮性フィルム
KR101818180B1 (ko) * 2016-05-13 2018-02-21 한국화학연구원 에틸렌 올리고머화 방법
JP6704878B2 (ja) * 2017-07-24 2020-06-03 大日本印刷株式会社 積層フィルム
JP6827892B2 (ja) * 2017-07-24 2021-02-10 大日本印刷株式会社 ポリオレフィン樹脂フィルム
JP7257001B2 (ja) * 2019-03-15 2023-04-13 大日本印刷株式会社 ポリオレフィン樹脂フィルム
JPWO2021006245A1 (fr) * 2019-07-05 2021-01-14

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5436203A (en) * 1977-08-09 1979-03-16 Petroleo Brasileiro Sa Process for preparing ethene
JPS56122318A (en) * 1980-03-04 1981-09-25 Teikoku Kako Kk Preparation of ethylene
JPH02157232A (ja) * 1988-12-08 1990-06-18 Fueritsuku Kk 簡易エチレン発生組成物及びこれを用いた簡易エチレン発生体並びにこの簡易エチレン発生体を用いた青果物の追熟方法
WO1999038822A1 (fr) * 1998-01-30 1999-08-05 Kabushiki Kaisha Sangi Synthese de matiere premiere de l'industrie chimique et de carburant a indice d'octane eleve, et composition pour carburant a indice d'octane eleve
JP2003501406A (ja) * 1999-06-07 2003-01-14 エクソンモービル・ケミカル・パテンツ・インク Ｓａｐｏモレキュラーシーブの触媒活性の保護
WO2005040392A1 (fr) * 2003-10-24 2005-05-06 Swedish Biofuels Ab Procede de production d'hydrocarbures et de composes contenant de l'oxygene a partir de la biomasse
JP2006116439A (ja) * 2004-10-21 2006-05-11 National Institute Of Advanced Industrial & Technology エチレン製造用触媒およびこの触媒を用いるエチレンの製造方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5436203A (en) * 1977-08-09 1979-03-16 Petroleo Brasileiro Sa Process for preparing ethene
JPS56122318A (en) * 1980-03-04 1981-09-25 Teikoku Kako Kk Preparation of ethylene
JPH02157232A (ja) * 1988-12-08 1990-06-18 Fueritsuku Kk 簡易エチレン発生組成物及びこれを用いた簡易エチレン発生体並びにこの簡易エチレン発生体を用いた青果物の追熟方法
WO1999038822A1 (fr) * 1998-01-30 1999-08-05 Kabushiki Kaisha Sangi Synthese de matiere premiere de l'industrie chimique et de carburant a indice d'octane eleve, et composition pour carburant a indice d'octane eleve
JP2003501406A (ja) * 1999-06-07 2003-01-14 エクソンモービル・ケミカル・パテンツ・インク Ｓａｐｏモレキュラーシーブの触媒活性の保護
WO2005040392A1 (fr) * 2003-10-24 2005-05-06 Swedish Biofuels Ab Procede de production d'hydrocarbures et de composes contenant de l'oxygene a partir de la biomasse
JP2006116439A (ja) * 2004-10-21 2006-05-11 National Institute Of Advanced Industrial & Technology エチレン製造用触媒およびこの触媒を用いるエチレンの製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
IND. ENG. CHEM. RES., vol. 36, no. 11, 1997, pages 4466 - 4475 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2365989A1 (fr) * 2008-11-13 2011-09-21 Arkema France Fabrication de copolymeres ethylene/acide carboxylique a partir de matieres renouvelables, copolymeres obtenus et utilisations
JP2010158236A (ja) * 2008-12-09 2010-07-22 Naoshi Monma もやし生育システム及び該システムにより育成されたもやし
JP2013051963A (ja) * 2008-12-09 2013-03-21 Naoshi Monma もやしの製造方法
JP2013060514A (ja) * 2011-09-13 2013-04-04 Sekisui Plastics Co Ltd ポリエチレン系樹脂発泡粒子、ポリエチレン系樹脂発泡成形体及びポリエチレン系樹脂発泡粒子の製造方法
JP2016150931A (ja) * 2015-02-19 2016-08-22 出光興産株式会社 軽質オレフィンの製造方法

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