EP1017686A1 - Procede de fabrication d'un oxiranne - Google Patents

Procede de fabrication d'un oxiranne

Info

Publication number
EP1017686A1
EP1017686A1 EP98951373A EP98951373A EP1017686A1 EP 1017686 A1 EP1017686 A1 EP 1017686A1 EP 98951373 A EP98951373 A EP 98951373A EP 98951373 A EP98951373 A EP 98951373A EP 1017686 A1 EP1017686 A1 EP 1017686A1
Authority
EP
European Patent Office
Prior art keywords
oxirane
extraction solvent
process according
mixture
diluent
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Withdrawn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
EP98951373A
Other languages
German (de)
English (en)
French (fr)
Inventor
Michel Strebelle
Patrick Gilbeau
Dominique Balthasart
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.)
Solvay SA
Original Assignee
Solvay SA
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 Solvay SA filed Critical Solvay SA
Publication of EP1017686A1 publication Critical patent/EP1017686A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/32—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids

Definitions

  • the present invention relates to a process for manufacturing an oxirane, more particularly to a process for separating the constituents of the reaction mixture obtained during the reaction between an olefinic compound and a peroxide compound in a liquid medium containing a diluent. It is known, in particular from patent application EP-A-1001 19, to transform an olefinic compound (that is to say an organic compound comprising at least one carbon-carbon double bond) into the corresponding oxirane by reaction with hydrogen peroxide in a liquid medium containing an alcohol.
  • an olefinic compound that is to say an organic compound comprising at least one carbon-carbon double bond
  • oxirane is systematically obtained as a mixture with alcohol and water.
  • the mixture of reaction products obtained at the outlet of the epoxidation reactor most often also contains unprocessed reactants as well as, optionally, certain impurities of the reactants and various reaction by-products.
  • the separation of the reaction product mixture into its constituents by distillation has serious drawbacks. It has in fact been observed that, when this mixture is subjected to distillation, a significant fraction of the oxirane produced can be degraded by hydrolysis and / or by alcoholysis. In addition, other parasitic reactions can also occur between different constituents of the reaction mixture during distillation, affecting the productivity of the process and which can complicate the production of an oxirane that meets the purity requirements.
  • the subject of the invention is a simple process for the manufacture of an oxirane by reaction between an olefinic compound and a peroxide compound, which makes it possible to easily obtain the oxirane in a substantially pure form, without degradation of a significant fraction of l oxirane during the separation step of the constituents of the reaction product mixture.
  • the invention therefore relates to a process for the manufacture of an oxirane by reaction between an olefinic compound and a peroxide compound in a liquid medium containing a diluent which is at least partially soluble in water, according to which a mixture of products is collected.
  • reaction comprising oxirane, diluent and water as well as, optionally, unconverted reactants
  • the said mixture is brought into contact with an extraction solvent so as to obtain two distinct liquid phases, namely, on the one hand , an extract containing at least part of the extraction solvent and at least 10% of the quantity of oxirane produced, and, on the other hand, a raffinate containing at least part of the diluent and at least part of the water, and said extract and said raffinate are then treated separately by distillation.
  • the extraction solvent can contain one or more compounds.
  • an extraction solvent is used which dissolves the oxirane well and in which the diluent is very slightly soluble. Solvents in which water is very sparingly or insoluble are very suitable. It is usually carried out in the absence of a water-soluble solvent. It may be advantageous to operate in the absence of salt.
  • an extraction solvent is used which, in addition, dissolves the starting olefinic compound well.
  • a substantially stable and chemically inert extraction solvent with respect to the constituents of the reaction product mixture under the extraction conditions, as well as in the subsequent distillation step.
  • Extraction solvents which give good results are those whose specific gravity differs from that of the mixture of reaction products by at least 0.02 g / cm- 5 , in particular at least 0.04 g / cm ⁇ . The best results are obtained when these specific weights differ by at least 0.05 g / cm ⁇ .
  • Compounds which can be used as extraction solvent in the process according to the invention are optionally halogenated saturated hydrocarbons containing from 3 to 20 carbon atoms, for example from 3 to 6 or from 10 to 20 carbon atoms, linear or branched, aliphatic or cyclic. Examples that may be mentioned include n-decane, n-tridecane, 1,2,3-trichloropropane and decaline (decahydronaphthalene). N-decane works well.
  • the extraction solvent can also be chosen from unsaturated hydrocarbons. These can optionally be halogenated. They generally contain from 3 to 20 carbon atoms. By way of example, mention may be made of allyl chloride.
  • Particularly efficient extraction solvents contain at least one compound chosen from o-dichlorobenzene, m-dichlorobenzene, 1,3,5-trimethylbenzene, decaline, o-chlorotoluene, 1,2,3- trichloropropane, allyl chloride, nitrobenzene, n-decane and their mixtures.
  • aromatic hydrocarbons optionally containing alkyl, halogen and / or nitrogen substituents. These generally contain from 6 to 12 carbon atoms. Examples that may be mentioned include o-, m- and p-xylenes, 1,3,5-trimethylbenzene, o-, m- and p-dichlorobenzenes, o-, m- and p-chlorotoluenes and nitrobenzene.
  • a mixture of at least two different solvents It may be advantageous to use a mixture of at least two different solvents. It may for example be mixtures of an aromatic hydrocarbon as described above with an aliphatic hydrocarbon as described above. Other mixtures which may be suitable are mixtures of aliphatic hydrocarbons. Mention may be made, by way of examples, of the mixtures of alkanes sold under the name ISOPAR® H and characterized by a range of boiling temperatures from 175 to 185 ° C. It can also be mixtures of aromatic hydrocarbons. Mention may be made, by way of examples, of the mixtures of alkylbenzenes marketed under the name SOLVESSO® 150 and characterized by a range of boiling temperatures from 190 to 196 ° C.
  • the oxirane prepared by the process according to the invention and present in the mixture of reaction products is an organic compound generally containing from 2 to 20 carbon atoms and comprising at least one epoxide group c ⁇ - c ' ⁇ O
  • the olefinic compounds which can be used in the process according to the invention generally contain from 2 to 20 carbon atoms. They are preferably those which contain 2, 3 or from 5 to 20 carbon atoms, more particularly 2, 3 or from 5 to 10 carbon atoms, for example 2 or 3 carbon atoms.
  • Examples of olefinic compounds which can be used in the process according to the invention are propylene, 1-butene, 2-methyl-1-propylene, 3-hexene, 1-octene, 1-decene and chloride of allyle.
  • the preferred olefinic compounds are propylene and allyl chloride.
  • Examples of oxirannes which can be separated by the process according to the invention are 1,2-epoxypropane, 1,2-epoxybutane, 1,2-epoxy-2-methylpropane, 3,4-epoxyhexane, 1,2-epoxyoctane, 1,2-epoxydecane and epichlorohydrin.
  • the process according to the invention is particularly suitable for the manufacture of epichlorohydrin. It also gives very good results for the manufacture of 1,2-epoxypropane.
  • the diluent used in the process according to the invention can be chosen from all organic solvents which are at least partially soluble in water. Solvents which are well suited are alcohols. Preferred alcohols contain from 1 to 5 carbon atoms and have only one -OH group. Examples that may be mentioned are methanol, ethanol, n-propanol, isopropanol, butanol and pentanol. Most often, it is methanol or tert-butanol.
  • the peroxide compound used in the process according to the invention can be chosen from hydrogen peroxide and any peroxide compound containing active oxygen and capable of carrying out an epoxidation.
  • any peroxide compound containing active oxygen and capable of carrying out an epoxidation As examples, mention may be made of the peroxide compounds obtained by oxidation of organic compounds such as ethylbenzene, isobutane and isopropanol. Inorganic peroxide compounds are well suited. Hydrogen peroxide is preferred.
  • the reaction product mixture generally contains at least 1% by weight of oxirane, most often at least 5% by weight. Usually, it contains at most 50% by weight. Preferably, it does not contain more than 20% thereof.
  • the reaction product mixture generally contains at least 30% by weight of diluent, most often at least 50% by weight. Usually, it contains at most 90% by weight. Preferably, it does not contain more than 75% thereof.
  • the reaction product mixture contains 5 to 25% water.
  • the content of unconverted olefinic compound in the reaction product mixture is generally from 5 to 20% by weight.
  • the molar ratio of the amount of olefinic compound used to the amount of peroxide compound used is generally at least 0.5, in particular at least 1.
  • the molar ratio is usually less than or equal to 10, especially at 4.
  • the contact between the extraction solvent and the mixture of reaction products is carried out according to conventional liquid-liquid extraction methods.
  • an extraction column is used in which the mixture of reaction products is brought into countercurrent contact with the extraction solvent.
  • the temperature at which the extraction solvent and the reaction product mixture are contacted is not critical. It can vary from 0 to 80 ° C. Temperatures above 40 ° C are suitable. In practice, it is advantageous to work at the temperature at which the reaction between the olefinic compound and the peroxide compound has been carried out.
  • the contacting of the extraction solvent with the mixture of reaction products is generally carried out at a pressure which can vary from atmospheric pressure to a pressure of 30 bars.
  • the pressure is advantageously greater than or equal to 1 bar and less than or equal to 20 bars.
  • the weight ratio between the extraction solvent and the mixture of reaction products depends on the solvent used and the extraction equipment used. In practice, the weight ratio between the extraction solvent and the mixture of reaction products is generally at least equal to 0.1. Preferably, it is equal to or greater than 1. This ratio usually does not exceed 5. Most often , it does not exceed 20. Good results have been obtained with a ratio of 1 to 5.
  • the subsequent stages of distillation of the extract and of the raffinate are carried out in a conventional manner and make it possible to easily collect the oxirane in a substantially pure form, to remove the water, to recycle the diluent and the reagents not converted to step of manufacturing the oxirane and the extraction solvent in the step of extracting the reaction product mixture.
  • the process according to the invention has proved to be very advantageous for separating 1,2-epoxy-3-chloropropane from the mixtures obtained by reaction of allyl chloride with hydrogen peroxide in the presence of a catalyst in a liquid medium containing an alcohol, in particular methanol.
  • the catalysts which can be used in these reactions generally contain a zeolite, namely a solid containing silica which has a microporous crystalline structure.
  • the zeolite is advantageously free of aluminum. It preferably contains titanium.
  • the zeolite can have a crystal structure of the ZSM-5, ZSM-11, MCM-41 type. Crystal structures different from that of beta zeolite are well suited.
  • ZSM-5 type zeolites are particularly suitable. Those with an infrared absorption band at about 950-960 cm ⁇ l are preferred.
  • Zeolites which are particularly suitable are titanium silicalites. Those corresponding to the formula xTi ⁇ 2 (lx) Si ⁇ 2 in which x is
  • 0.0001 to 0.5, preferably 0.001 to 0.05 are effective.
  • Materials of this type known as TS-1 and having a crystal structure of the ZSM-5 type, give particularly favorable results.
  • Examples 1 and 2 (in accordance with the invention) A mixture of reaction products was used comprising 67.3% by weight of methanol, 10.0% by weight of allyl chloride, 12.0% by weight of epichlorohydrin and 10.7% by weight of water. The specific gravity of this mixture was 0.85 kg / 1.
  • Example 2 decalin was used as the extraction solvent.
  • the partition coefficient was 0.21.
  • Example 3 (in accordance with the invention) The operations of Example 1 were repeated with the exception of the volumes used. 3 volumes of extraction solvent were brought into contact with 1 volume of reaction product mixture. Different extraction solvents were used (see Table 1 which also indicates the specific gravity and the boiling point of the solvents). The partition coefficients obtained are shown in Table 1. Table 1 Ex. Solvent Coefficient

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Epoxy Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP98951373A 1997-09-18 1998-09-10 Procede de fabrication d'un oxiranne Withdrawn EP1017686A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
BE9700756 1997-09-18
BE9700756A BE1011456A3 (fr) 1997-09-18 1997-09-18 Procede de fabrication d'un oxiranne.
PCT/EP1998/005750 WO1999014208A1 (fr) 1997-09-18 1998-09-10 Procede de fabrication d'un oxiranne

Publications (1)

Publication Number Publication Date
EP1017686A1 true EP1017686A1 (fr) 2000-07-12

Family

ID=3890733

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98951373A Withdrawn EP1017686A1 (fr) 1997-09-18 1998-09-10 Procede de fabrication d'un oxiranne

Country Status (10)

Country Link
US (1) US6350888B1 (enExample)
EP (1) EP1017686A1 (enExample)
JP (2) JP5073132B2 (enExample)
AR (1) AR023007A1 (enExample)
AU (1) AU9742598A (enExample)
BE (1) BE1011456A3 (enExample)
BR (1) BR9812516A (enExample)
SA (1) SA98190748B1 (enExample)
WO (1) WO1999014208A1 (enExample)
ZA (1) ZA988398B (enExample)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1122249A1 (fr) 2000-02-02 2001-08-08 SOLVAY (Société Anonyme) Procédé de fabrication d'un oxiranne
EP1420014A4 (en) * 2001-08-22 2004-09-29 Sumitomo Chemical Co PROCESS FOR PRODUCING PROPYLENE OXIDE
FR2846964B1 (fr) * 2002-11-12 2006-07-21 Procede de fabrication de 1,2-epoxy-3-chloropropane
FR2846965B1 (fr) * 2002-11-12 2006-10-13 Procede de fabrication de 1,2-epoxy-3-chloropropane
US7169945B2 (en) 2002-11-26 2007-01-30 Degussa Ag Process for the epoxidation of olefins
US7531674B2 (en) 2003-03-06 2009-05-12 Sumitomo Chemical Company, Limited Process for producing propylene oxide
EP1770081A1 (en) * 2003-11-20 2007-04-04 SOLVAY (Société Anonyme) Process for producing dichloropropanol from glycerol , the glycerol coming eventualy from the conversion of animal fats in the manufacture of biodiesel
KR20080037615A (ko) 2005-05-20 2008-04-30 솔베이(소시에떼아노님) 클로로히드린의 제조 방법
US20080214848A1 (en) * 2005-05-20 2008-09-04 Solvay (Societe Anonyme) Method For Making an Epoxy Starting From a Chlorhydrine
BRPI0618325A2 (pt) * 2005-11-08 2011-08-23 Solvay processo parar a produção de dicloropropanol
EP2043984A1 (en) * 2006-06-14 2009-04-08 Solvay S.A. Crude glycerol-based product, process for its purification and its use in the manufacture of dichloropropanol
KR100846435B1 (ko) * 2006-12-22 2008-07-16 한화석유화학 주식회사 옥시란 화합물의 제조 방법
US20100032617A1 (en) * 2007-02-20 2010-02-11 Solvay (Societe Anonyme) Process for manufacturing epichlorohydrin
FR2913421B1 (fr) * 2007-03-07 2009-05-15 Solvay Procede de fabrication de dichloropropanol.
FR2913684B1 (fr) 2007-03-14 2012-09-14 Solvay Procede de fabrication de dichloropropanol
CN101293882B (zh) * 2007-04-24 2011-04-20 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
TW200911740A (en) 2007-06-01 2009-03-16 Solvay Process for manufacturing a chlorohydrin
TWI500609B (zh) * 2007-06-12 2015-09-21 Solvay 含有環氧氯丙烷的產品，其製備及其不同應用中的用途
TW200911693A (en) 2007-06-12 2009-03-16 Solvay Aqueous composition containing a salt, manufacturing process and use
KR20100089835A (ko) * 2007-10-02 2010-08-12 솔베이(소시에떼아노님) 용기의 내부식성 향상을 위한 실리콘-함유 조성물의 용도
FR2925045B1 (fr) 2007-12-17 2012-02-24 Solvay Produit a base de glycerol, procede pour son obtention et son utilisation dans la fabrication de dichloropropanol
TWI478875B (zh) * 2008-01-31 2015-04-01 Solvay 使水性組成物中之有機物質降解之方法
EP2103604A1 (de) * 2008-03-17 2009-09-23 Evonik Degussa GmbH Verfahren zur Herstellung von Epichlorhydrin
JP5619721B2 (ja) 2008-04-03 2014-11-05 ソルヴェイ（ソシエテ アノニム） グリセロールを含む組成物、それを得る方法およびジクロロプロパノールの製造でのその使用
EP2149569A1 (en) * 2008-08-01 2010-02-03 Hexion Specialty Chemicals Research Belgium S.A. Process for the manufacture of a 1,2-Epoxide
EP2149570A1 (en) * 2008-08-01 2010-02-03 Hexion Specialty Chemicals Research Belgium S.A. Process for the manufacture of epichlorohydrin using hydrogen peroxide and a manganese komplex
FR2935968B1 (fr) 2008-09-12 2010-09-10 Solvay Procede pour la purification de chlorure d'hydrogene
CN101880263B (zh) * 2009-05-09 2012-07-11 中国石油化工集团公司 一种环氧氯丙烷的制备方法
MX2012000556A (es) * 2009-07-16 2012-04-11 Basf Se Metodo para la separacion de acetonitrilo a partir de agua.
EP2343288A1 (en) 2009-11-27 2011-07-13 Momentive Specialty Chemicals Research Belgium S.A. Process for the manufacture of propylene oxide
EP2354131A1 (en) 2010-02-02 2011-08-10 Momentive Specialty Chemicals Research Belgium Process for the manufacture of a 1,2-epoxide and a device for carrying out said process
KR20140009163A (ko) 2010-09-30 2014-01-22 솔베이(소시에떼아노님) 천연유래 에피클로로히드린의 유도체
FR2966825B1 (fr) * 2010-10-29 2014-05-16 Solvay Procede de fabrication d'epichlorhydrine
EA201391089A1 (ru) 2011-01-27 2014-06-30 Солвей Са Способ изготовления 1,2-эпокси-3-хлорпропана
EA201391090A1 (ru) 2011-01-27 2013-12-30 Солвей Са Способ получения 1,2-эпокси-3-хлорпропана
CN105439983A (zh) * 2011-02-04 2016-03-30 蓝立方知识产权有限责任公司 混合物的相分离
CN103420949B (zh) * 2012-05-18 2016-05-25 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
CN103420948B (zh) * 2012-05-18 2016-05-25 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
CN103420947B (zh) * 2012-05-18 2016-07-06 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
CN103420946B (zh) * 2012-05-18 2016-08-03 中国石油化工股份有限公司 一种环氧氯丙烷的分离方法
CN104003961B (zh) * 2013-02-27 2016-05-25 中国石油化工股份有限公司 一种连续萃取环氧氯丙烷的方法
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CN111592506A (zh) * 2020-06-02 2020-08-28 中国科学院理化技术研究所 环氧氯丙烷分离工艺

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Also Published As

Publication number Publication date
WO1999014208A1 (fr) 1999-03-25
JP2010159281A (ja) 2010-07-22
ZA988398B (en) 2000-03-22
BR9812516A (pt) 2000-07-25
AR023007A1 (es) 2002-09-04
AU9742598A (en) 1999-04-05
BE1011456A3 (fr) 1999-09-07
US6350888B1 (en) 2002-02-26
SA98190748B1 (ar) 2006-05-01
JP5073132B2 (ja) 2012-11-14
JP2001516753A (ja) 2001-10-02

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