WO2003051829A1 - Procede de purification de melange reactionnel d'oxydation liquide - Google Patents

Procede de purification de melange reactionnel d'oxydation liquide Download PDF

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Publication number
WO2003051829A1
WO2003051829A1 PCT/JP2002/012950 JP0212950W WO03051829A1 WO 2003051829 A1 WO2003051829 A1 WO 2003051829A1 JP 0212950 W JP0212950 W JP 0212950W WO 03051829 A1 WO03051829 A1 WO 03051829A1
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WO
WIPO (PCT)
Prior art keywords
oxidation reaction
purified
reaction solution
aqueous layer
cumene
Prior art date
Application number
PCT/JP2002/012950
Other languages
English (en)
Japanese (ja)
Inventor
Shigeru Goto
Noriaki Oku
Toshikazu Ohmae
Original Assignee
Sumitomo Chemical Company, Limited
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 Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Priority to AU2002354166A priority Critical patent/AU2002354166A1/en
Publication of WO2003051829A1 publication Critical patent/WO2003051829A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • C07C407/003—Separation; Purification; Stabilisation; Use of additives

Definitions

  • the present invention relates to a method for purifying an oxidation reaction solution. More specifically, the present invention relates to a method for purifying an oxidation reaction solution containing cumene hydroperoxide obtained by oxidizing cumene, wherein the water used for purification is effectively used, and therefore, a relatively small amount of water is used.
  • the present invention relates to a method for purifying an oxidation reaction solution, which has excellent characteristics that an oxidation reaction solution can be purified and a wastewater treatment amount can be reduced. Background art
  • a method for obtaining propylene oxide by oxidizing cumene into cumene hydroperoxide and subjecting the cumene hydroperoxide and propylene to an epoxidation reaction is known.
  • the concentration of the organic acid in the oxidation reaction solution containing cumene hydropoxide obtained by oxidizing cumene is preferably 0.5% by weight or less, more preferably 0.1% by weight. % Is disclosed in JP-A-2001-031662.
  • Japanese Patent Application Laid-Open No. 2001-270875 discloses that it is necessary that the concentration be 100 ppm by weight or less, and that washing with water before the epoxidation step is preferable from the viewpoint of efficient batch removal of sodium. It has been disclosed. Further, with respect to the water concentration in the oxidation reaction solution containing cumenehydroxide used in the epoxidation step, JP-A-2001-270876 discloses a step of removing water.
  • An object of the present invention is a method for purifying an oxidation reaction solution containing cumene hydrooxide obtained by oxidizing cumene, wherein the water used for purification is effectively used, and thus the oxidation reaction is performed with a relatively small amount of water. It is an object of the present invention to provide a method for purifying an oxidation reaction solution, which has excellent characteristics that the solution can be purified and the amount of wastewater treatment can be reduced.
  • Purification here means neutralizing the organic acids present in the oxidation reaction solution containing cumene hydroxide obtained by oxidizing cumene with alcohol, and forming the salts and excess alkali added. To be removed by water washing.
  • the present invention relates to a method for purifying an oxidation reaction solution containing cumene hydroperoxide obtained by oxidizing cumene including the following steps.
  • First step Add the alkaline aqueous solution (2) and all or part of the aqueous layer (3) obtained in the second step below to the oxidation reaction solution (1) to be purified (1) and mix them. Step of separating into (5) and aqueous layer (6)
  • Second step Add all or part (8) of the aqueous layer (7) obtained in the following third step to the oil layer (5) obtained in the first step and mix, and then add the oil layer (9) and the aqueous layer (3) Separation process
  • Third step a step of adding water (10) to the oil layer (9) obtained in the second step, mixing and then separating into a purified oil layer (11) and an aqueous layer (7).
  • FIG. 1 shows an example of the flow of the present invention. The broken line in the figure should be installed as necessary
  • Oxidation reaction solution to be purified > 2. Aqueous solution, 3. Aqueous layer, 4. Part or all of aqueous layer, 5. Oil layer, 6. Aqueous layer, 7. Aqueous layer, 8. Aqueous layer Part or all, 9. Reservoir, 10. Water, 11. Refined reservoir Reservoir for implementing the invention
  • the present invention is a method for purifying an oxidation reaction solution containing cumene hydridoperoxide obtained by oxidizing cumene.
  • the oxidation of cumene is usually performed by autoxidation with oxygenated gas such as air or oxygen-enriched air. This oxidation reaction may be carried out without using an additive, or an additive such as an alkali may be used.
  • the reaction temperature is usually 50 to 200, and the reaction pressure is usually between atmospheric pressure and 5 MPa.
  • the alkali includes an alkali metal compound such as Na ⁇ H or K ⁇ H and an aqueous solution thereof, or an alkali earth metal compound or Na 2 C ⁇ 3 or NaHCO 3 Alkali metal carbonate or ammonia and (NH 4 ) 2 CO 3 , alkali metal ammonium carbonate and the like and an aqueous solution thereof are used.
  • an alkaline aqueous solution (2) and all or a part of the aqueous layer (3) obtained in the second step described below are added to the oxidation reaction solution (1) to be purified, mixed, and then mixed. This is the step of separating into a back oil layer (5) and an aqueous layer (6).
  • Alkaline aqueous solution supplied to the first step is N A_ ⁇ _H, alkali metals such as or an aqueous solution of an alkali metal compound such as K_ ⁇ _H, Al force Li earth metal compound or N a 2 C_ ⁇ 3, NaHCO 3
  • An aqueous solution of carbonate, ammonia, (NH 4 ) 2 C 3 , alkali metal ammonium carbonate, or the like is used, and may be added directly to the oxidation reactor or may be added after the reaction.
  • the operating temperature of the present apparatus (that is, the temperature of the oxidation reaction solution to be purified) is preferably equal to or lower than the temperature represented by the following formula (1) as described in JP-A-200270874.
  • the operating pressure is preferably between atmospheric pressure and 5 MPa.
  • a common mixing device and oil-water separation device can be used as in the first step.
  • the operating temperature and pressure of the present apparatus are preferably in the same ranges as in the first step.
  • the third step is a step in which water (10.) is added to the oil layer (9) obtained in the second step, mixed, and then separated into a purified oil layer (11) and an aqueous layer (7). is there.
  • a common mixing apparatus and an oil-water separation apparatus can be used as in the first and second steps.
  • the operating temperature and pressure are also preferably in the same range as in the first step.
  • the present invention includes the above-described first to third steps as essential steps. However, if necessary, these steps can be further added in series to enhance the effect of purification.
  • the oxidation reaction solution containing cumene hydroperoxide purified according to the present invention is usually dehydrated and then subjected to an epoxidation reaction between cumene hydroperoxide and propylene in the presence of an epoxidation catalyst to form propylene oxide.
  • the epoxidation reaction is preferably carried out in the presence of a catalyst comprising a titanium-containing silicon oxide, from the viewpoint of obtaining the target product with high yield and high selectivity.
  • a catalyst comprising a titanium-containing silicon oxide
  • These catalysts are preferably so-called titanium-silica catalysts containing titanium chemically bonded to silicon oxide.
  • a titanium compound supported on a silica carrier, a compound compounded with silicon oxide by a coprecipitation method or a sol-gel method, or a zeolite compound containing titanium can be used.
  • the epoxidation reaction is carried out by bringing propylene and cumene hydroxide into contact with a catalyst.
  • the reaction can be carried out in a liquid phase using a solvent.
  • the solvent must be liquid at the temperature and pressure of the reaction and must be substantially inert to the reactants and products.
  • the solvent may consist of the substances present in the hydroperoxide solution used.
  • cumene hydroperoxide is a mixture of the raw material and cumene, it can be used as a substitute for the solvent without adding a solvent.
  • Other useful solvents include aromatic monocyclic compounds (eg, benzene, toluene, cyclobenzene, orthodichlorobenzene) and alkanes (eg, octane, decane, dodecane).
  • the epoxidation reaction temperature is generally 0 to 200 ° C, but preferably 25 to 200 ° C.
  • the pressure may be sufficient to keep the reaction mixture in a liquid state. In general, it is advantageous for the pressure to be between 100 and 1000 kPa.
  • the epoxidation reaction can be advantageously carried out using a catalyst in the form of a slurry or fixed bed.
  • a catalyst in the form of a slurry or fixed bed.
  • it is preferred to use a fixed bed. It can be carried out by a batch method, a semi-continuous method, a continuous method, or the like.
  • the liquid containing the reactants is passed through the fixed bed, the liquid mixture leaving the reaction zone contains no or substantially no catalyst.
  • the present invention in the purification of an oxidation reaction solution containing cumenehydroxide peroxide, water used for purification can be effectively used, and thus the oxidation reaction solution can be purified with a relatively small amount of water, and It is possible to provide a method for purifying an oxidation reaction solution having an excellent feature that the amount of wastewater treatment can be reduced.

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

Abstract

L'invention concerne un procédé de purification de mélange réactionnel d'oxydation liquide contenant de l'hydroperoxyde de cumène, qui résulte de l'oxydation de cumène et comporte les étapes suivantes : premièrement, ajouter et mélanger au mélange réactionnel (1) d'oxydation liquide à purifier une solution (2) alcaline aqueuse et tout ou partie (4) de la phase aqueuse (3) devant être obtenue dans la deuxième étape, et séparer le mélange résultant de façon à obtenir une couche d'huile (5) et une couche aqueuse (6) ; deuxièmement, ajouter et mélanger à la couche d'huile (5) obtenue dans la première étape tout ou partie (8) de la couche aqueuse (7) devant être obtenue dans la troisième étape, et séparer le mélange résultant de façon à obtenir une couche d'huile (9) et une couche aqueuse (3) ; troisièmement ajouter et mélanger de l'eau (10) à la couche d'huile (9) obtenue dans la deuxième étape, et séparer le mélange résultant de façon à obtenir une couche d'huile (11) purifiée et une couche d'eau (7).
PCT/JP2002/012950 2001-12-19 2002-12-11 Procede de purification de melange reactionnel d'oxydation liquide WO2003051829A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002354166A AU2002354166A1 (en) 2001-12-19 2002-12-11 Method of purifying liquid oxidation reaction mixture

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001/385840 2001-12-19
JP2001385840A JP2003183248A (ja) 2001-12-19 2001-12-19 酸化反応液の精製方法

Publications (1)

Publication Number Publication Date
WO2003051829A1 true WO2003051829A1 (fr) 2003-06-26

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2002/012950 WO2003051829A1 (fr) 2001-12-19 2002-12-11 Procede de purification de melange reactionnel d'oxydation liquide

Country Status (4)

Country Link
JP (1) JP2003183248A (fr)
AU (1) AU2002354166A1 (fr)
TW (1) TW200301242A (fr)
WO (1) WO2003051829A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4438458B2 (ja) 2003-09-25 2010-03-24 住友化学株式会社 溶液からの目的物質の回収方法
JP2008074909A (ja) * 2006-09-19 2008-04-03 Nippon Shokubai Co Ltd 重合開始剤又はその溶液及び電子情報材料用重合体の製造方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05178773A (ja) * 1991-12-26 1993-07-20 Sumitomo Chem Co Ltd フェノール及びメチルエチルケトンの製造方法
EP0816335A1 (fr) * 1996-06-27 1998-01-07 General Electric Company Procédé d'oxydation du cumène
WO2001005778A1 (fr) * 1999-07-14 2001-01-25 Sumitomo Chemical Company, Limited Procede de production d'oxyde de propylene
WO2001070710A1 (fr) * 2000-03-24 2001-09-27 Sumitomo Chemical Company, Limited Procede de production d'oxyde de propylene
JP2001270875A (ja) * 2000-03-24 2001-10-02 Sumitomo Chem Co Ltd プロピレンオキサイドの製造方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05178773A (ja) * 1991-12-26 1993-07-20 Sumitomo Chem Co Ltd フェノール及びメチルエチルケトンの製造方法
EP0816335A1 (fr) * 1996-06-27 1998-01-07 General Electric Company Procédé d'oxydation du cumène
WO2001005778A1 (fr) * 1999-07-14 2001-01-25 Sumitomo Chemical Company, Limited Procede de production d'oxyde de propylene
WO2001070710A1 (fr) * 2000-03-24 2001-09-27 Sumitomo Chemical Company, Limited Procede de production d'oxyde de propylene
JP2001270875A (ja) * 2000-03-24 2001-10-02 Sumitomo Chem Co Ltd プロピレンオキサイドの製造方法

Also Published As

Publication number Publication date
JP2003183248A (ja) 2003-07-03
TW200301242A (en) 2003-07-01
AU2002354166A1 (en) 2003-06-30

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