WO2008038619A1 - Procédé de production de sel quaternaire de (méth)acrylate de dialkylaminoalkyle - Google Patents

Procédé de production de sel quaternaire de (méth)acrylate de dialkylaminoalkyle Download PDF

Info

Publication number
WO2008038619A1
WO2008038619A1 PCT/JP2007/068521 JP2007068521W WO2008038619A1 WO 2008038619 A1 WO2008038619 A1 WO 2008038619A1 JP 2007068521 W JP2007068521 W JP 2007068521W WO 2008038619 A1 WO2008038619 A1 WO 2008038619A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
reactor
dialkylaminoalkyl
reaction
acrylate
Prior art date
Application number
PCT/JP2007/068521
Other languages
English (en)
Japanese (ja)
Inventor
Kunihiko Hirose
Taketsugu Aoyama
Juichi Gotoh
Shinju Yamamoto
Original Assignee
Mt Aquapolymer, 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 Mt Aquapolymer, Inc. filed Critical Mt Aquapolymer, Inc.
Priority to CN2007800355933A priority Critical patent/CN101516828B/zh
Publication of WO2008038619A1 publication Critical patent/WO2008038619A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups

Definitions

  • the present invention relates to a method for producing a dialkylaminoalkyl (meth) acrylate quaternary salt.
  • Dialkylaminoalkyl (meth) atalylate quaternary salts are raw materials for cationic polymers, and are a polymer flocculant, paper strength enhancer, and antistatic agent. In addition, it is used for various purposes as a raw material for manufacturing soil improvers and the like.
  • DAM uses water as a solvent, and in the presence of the solvent, dialkylaminoalkyl (meth) acrylate (hereinafter referred to as “Da”) and a quaternizing agent (for example, methyl chloride) Is produced in the form of an aqueous solution of DAM.
  • a quaternizing agent for example, methyl chloride
  • a raw material is charged using one reactor, and after completion of the reaction, a product is extracted (for example, Patent Documents 1 and 2), or a raw material is supplied.
  • Patent Document 3 that continuously extracts the reaction solution from the reactor is adopted.
  • the present inventors perform the supply of the quaternizing agent to the reactor with the ejector, thereby further preventing the reaction solution from flowing back into the supply pipe of the quaternizing agent. It has been found that the quaternizing agent is sufficiently blown, the solubility of the quaternizing agent in the reaction solution is improved, and the reactivity is excellent (Patent Document 4).
  • Patent Document 1 JP-A-4 217649
  • Patent Document 2 JP-A-8-268985
  • Patent Document 3 Japanese Unexamined Patent Publication No. 2003-342244
  • Patent Document 4 Japanese Unexamined Patent Application Publication No. 2004-155669
  • Methyl chloride is widely used as a quaternizing agent that is a raw material for the above-mentioned DAM. 4th grade In the case of using chlorinated methethylyl as a chemical agent, it is mixed with air and air and mixed with gas. ⁇ Chloroform ;; chlorinated methictill explosion explosion range 1100 .. 77 ⁇ ;; 1177 .. 44VV // VV %%))
  • the gas gas can be stored in the gas-phase part of the reaction reactor. Control of the composition of the composition is extremely important. .
  • DDAAMM is polymerized in the reaction reactor. Combined and good, only low quality DDAAMM can be obtained, and the remaining concentration of chlorinated methethylyl is low and low rinse. In this case, the reaction of the hydrolyzed water decomposition progresses between here and the 44th-classification reaction reaction slows down.
  • DDAAMM's product price value has increased due to the increase in the ((Memethata)) aacrylyluric acid ((hereinafter referred to as “AAAA”)) of living organisms. This causes problems such as low drop in the value. .
  • the present invention describes the composition of the Gagasus group in the gas-gas phase portion in the reaction reactor. Control and control within the range of the range, while maintaining safety and safety integrity, while maintaining high productivity and high productivity and high purity.
  • the method of manufacturing and manufacturing the DDAAMM is to provide and provide the method of manufacturing and manufacturing the DDAAMM. .
  • the present invention is based on the following didiaaralkylkiluaamiminonoaralkylkiru ((memetata)) atta ri relate salt of the 44th grade salt. Provide manufacturing and manufacturing methods. .
  • the didiaalkyloxylamiminonoalalkylyl ((metheta)) attaylyl relate, chlorinated methethylyl and water According to the supply and supply of this, the didiaaralkylkiluaamiminonoarukikiruru ((Memetata)) atta ri relato salt 44 grade salt is manufactured and manufactured This is a method of slicking, in which the concentration of oxyoxygen in the gas phase portion in the reaction reactor (([[ ⁇ ⁇ ]]))) 33 ⁇ ; 1122 volume% volume,
  • Acid concentration of the chlorinated methethylyl chloride (([[MMCC]])) from 2222 to 8800 volume%, and the concentration of the chlorinated methethylyl chloride
  • the ratio ratio of oxygen concentration (([OO]] // [[MMCC]])) is controlled to 00 .. 0055--00 .. Jiji which makes this and this as a special feature [0012] Item 2.
  • the ratio of the oxygen concentration to the sum of the oxygen concentration and the nitrogen concentration ([ ⁇ ] / ([ ⁇ ] + [N])) in the gas phase portion in the reactor is 0. ⁇ Response to 05-0.2
  • Item 2 A method for producing a dialkylaminoalkyl (meth) acrylate quaternary salt according to Item 1.
  • Item 3 Item 1 or 2 in which a dialkylaminoalkyl (meth) atalylate aqueous solution of quaternary salt is charged in the reactor in advance and then dialkylaminoalkyl (meth) acrylate, methyl chloride and water are supplied thereto.
  • Item 4 Concentration of dialkylaminoalkyl (meth) acrylate quaternary salt ([DAM]), concentration of dialkylaminoalkyl (meth) acrylate ([Da]) and chloride Item 4.
  • DAM dialkylaminoalkyl
  • [Da] concentration of dialkylaminoalkyl (meth) acrylate
  • chloride Item 4.
  • Item 5 The process for producing a dialkylaminoalkyl (meth) acrylate quaternary salt according to any one of Items 1 to 4, wherein the temperature of the reaction solution during the reaction is maintained at 30 to 80 ° C.
  • Item 6 The dialkylaminoalkyl (1) according to any one of Items 1 to 5, wherein the reactor is a sealed reactor, and the internal pressure of the reactor during the reaction is maintained at 0.10 to 1 MPaG.
  • Methoda Atallylate A method for producing a quaternary salt.
  • Item 7 Items wherein dialkylaminoalkyl (meth) acrylate, methyl chloride and water are continuously supplied to the reactor, and the reaction liquid in the reactor is continuously extracted; A method for producing a dialkylaminoalkyl (meth) acrylate quaternary salt according to any one of the above.
  • Item 8 The process for producing a dialkylaminoalkyl (meth) ate quaternary salt according to any one of Items 1 to 7, wherein the dialkylaminoalkyl (meth) acrylate is dimethylaminoethyl (meth) acrylate. .
  • Item 9 The method for producing a dialkylaminoalkyl (meth) acrylate quaternary salt according to any one of Items 1 to 8, wherein the methyl chloride is supplied by an ejector.
  • Item 10 The method according to Item 9, wherein a part of the reaction solution is extracted from the reactor, cooled through a heat exchanger, and the cooled reaction solution is supplied into the reactor together with methyl chloride by an ejector.
  • Item 11 The reaction solution continuously withdrawn from the reactor is separated into one or more sealed Item 11.
  • the reaction is performed by controlling the gas composition in the gas phase part in the reactor within a predetermined range, so that DAM having high productivity and high purity can be obtained while maintaining safety. Can be manufactured.
  • the production method of the present invention is a DAM production method that is extremely excellent even on an industrial scale.
  • FIG. 1 is a schematic diagram showing an example of a reactor.
  • FIG. 2 is a schematic diagram showing an example of a reactor equipped with an ejector.
  • FIG. 3 is a schematic diagram showing an example of a reaction apparatus composed of a reaction tank A, an aging tank B, and a finishing tank C. Explanation of symbols
  • (meta) acrylate refers to ate relay or meta acrylate.
  • the present invention is a method for producing DAM by supplying Da, methyl chloride and water to a reactor, wherein the concentration of oxygen in the gas phase portion in the reactor (hereinafter referred to as [O] and 3); 12 bodies
  • the size, material, and structure of the reactor used in the present invention are not particularly limited as long as each material can be reacted to produce DAM.
  • the reactor has an inner surface coated and / or lined with glass, Teflon (registered trademark) or the like, and can avoid elution of metal components in the resulting DAM aqueous solution.
  • a pure DAM aqueous solution can be obtained, which is preferable.
  • the reactor used in the present invention includes, for example, as shown in FIG. 1, a Da supply pipe (2), a water supply pipe (1), a methyl chloride supply pipe (3), a stirring blade (5), and A reaction liquid outlet (4) is provided.
  • the reactor is usually provided with a jacket type heat exchanger (10).
  • FIG. 2 shows an example of a reactor equipped with an ejector (8).
  • the ejector is also called an aspirator.
  • the reaction liquid in the reactor is extracted by the circulation pump (7) and supplied to the nozzle part (11) of the ejector (8), and the pressure in the ejector is reduced.
  • Methyl chloride is sucked from the suction part (9) and supplied to the reaction solution.
  • the reaction outlet (4) is usually provided at the bottom of the reactor.
  • the ejector is provided at the top of the reactor. If the reactor has at least one ejector, it is sufficient to select the optimum number according to the size of the reactor and the reaction amount.
  • a heat exchanger for cooling the extracted reaction liquid is provided in the middle of the flow path for supplying the reaction liquid extracted from the reactor (6) by the circulation pump (7) to the ejector (8). It may be provided (not shown). As a result, heat removal in the reactor can be effectively performed, and temperature control in the reactor becomes extremely simple. Furthermore, in addition to the reactor described above, a finishing tank for treating the reaction solution and an aging tank may be provided.
  • dialkylaminoalkyl (meth) acrylate, methyl chloride and water are used as raw materials.
  • Da include dimethylaminoethyl (meth) acrylate, jetylaminoethyl (meth) acrylate, dipropylaminoethyl (meth) acrylate and dimethylaminopropyl (meth) acrylate.
  • Preferred is dimethylaminoethyl (meth) acrylate.
  • Methyl chloride is flammable but weakly burns. Mixes with air to form explosive gas mixture. The explosion range is from 10.7 to 17.4V / V%, and the boiling point is 24.1 ° C.
  • water used in the present invention it is preferable to use water having a purity as high as possible that does not contain a metal or the like. Specific examples include distilled water and ion exchange water.
  • the reaction may be a batch type or a continuous type.
  • the continuous type is preferred. Specific examples of the continuous type include a mode in which Da, methyl chloride and water are continuously supplied to the reactor, and the reaction liquid in the reactor is continuously withdrawn.
  • Various modes can be adopted as a supply form of methyl chloride to the reactor. Examples thereof include a method of introducing gaseous methyl chloride as it is into the gas phase of the reactor, a method of introducing it into the reaction solution of the reactor, and a method of supplying liquefied methyl chloride.
  • Ejector When supplied using methyl chloride, methyl chloride is fed into the reactor through the suction part (9) of the ejector (8) (Fig. 2). Da and water can be supplied according to conventional methods.
  • methyl chloride, and water may be supplied to the reaction solution, or may be supplied to the upper space of the reaction solution in the reactor. As described above, when methyl chloride is supplied to the reaction solution via the ejector, it is preferably supplied to the reaction solution. As for Da, in order to prevent DAC crystals from precipitating during the supply process and blocking the introduction pipe, the tip of the Da introduction pipe is positioned in the space above the reaction solution, and Da is supplied from there. Is preferable
  • a DAM aqueous solution as a reaction solvent.
  • the resulting DAM becomes crystalline and has a hygroscopic property so that it adheres to the inner wall of the reactor and makes it difficult to remove heat.
  • DAM since DAM is crystalline, it becomes oxygen-free and DAM is polymerized.
  • there is a method using water as a solvent In this case, however, there is a problem that the raw material Da is hydrolyzed and the purity of the product is lowered.
  • the order in which the DAM aqueous solution as a reaction solvent and the raw materials are charged into the reactor is not particularly limited as long as the reaction of the raw materials proceeds.
  • the DAM aqueous solution is charged in the reactor in advance! /
  • a method of supplying each raw material from the reactor, and simultaneously with supplying the raw material or while supplying the raw material, the DAM aqueous solution For example, a method of charging in a reactor.
  • the former is preferred. This is because, if a DAM aqueous solution is previously charged as a reaction solvent in the reactor and then each raw material is supplied, problems such as crystallization of DAM, polymerization of DAM, and hydrolysis of raw material Da can be reduced.
  • the DAM contained in the DAM aqueous solution charged in advance is usually the same type of DAM as the DAM obtained by the reaction.
  • the concentration of the DAM aqueous solution is a force S that can be in various ranges, 50 to 84% by weight, preferably 75 to 84% by weight, and more preferably 78 to 83% by weight.
  • the inside of the reactor during the reaction satisfies the following conditions.
  • Da methyl chloride and water may be supplied into the reactor.
  • nitrogen and air can be supplied as necessary.
  • Nitrogen or air can be supplied by blowing nitrogen or air into Da or water.
  • [O] in the gas phase part in the reactor is 3 to 12% by volume, preferably 4 to 10% by volume, and more.
  • [MC] is controlled to 22 to 80% by volume, preferably 35 to 65% by volume, and more preferably 40 to 55% by volume.
  • [O] / [MC] in the gas phase in the reactor is set to 0.05-0.5, and further to 0.0-07.
  • control it is preferable to control to 35, particularly from 0.10 to 0.2.
  • the ratio of the oxygen concentration to the sum of the oxygen concentration and the nitrogen concentration ([ ⁇ ] / ([ ⁇ ] + [N])) in the gas phase portion in the reactor is set to 0 ⁇ 05- 0.2, then 0.07
  • the concentration of these gases can be measured using a gas chromatograph after extracting the gas in the gas phase in the reactor.
  • the pressure inside the reactor during the reaction is 0.1 to IMPaG, preferably (or 0.1—0.8 MPaG, more preferably (It is preferable that the pressure be maintained at 0.1 to 0.6 MPaG. S This can increase the amount of methyl chloride dissolved in the reaction solution.)
  • the feed rate of each raw material should be set appropriately according to the size of the reactor, the production amount per unit time, and the like. Is achieved.
  • the supply rate of Da is 3 to 70 mass% with respect to the mass of the reaction liquid in the reactor.
  • More preferred is 5 to 35% by mass / hour.
  • the supply rate of methyl chloride is based on the mass of the reaction solution in the reactor;! -30 mass%
  • More preferred is 2 to 15% by mass / hour.
  • the supply rate of water is preferably 2 to 15 mass% / hour, more preferably 2 to 15 mass% / hour, based on the mass of the reaction liquid in the reactor.
  • the inside of the reactor at a constant temperature in the stage of continuously supplying each raw material into the reactor and the stage of reaction.
  • the reaction temperature is preferably 30 to 80 ° C, more preferably 40 to 70. C.
  • the reaction solution is extracted after the reaction is completed, and the loca reaction solution is extracted.
  • the raw materials are supplied during the reaction and the reaction solution in the reactor is withdrawn.
  • the reaction solution is then measured by the power supplied to the finishing or aging tank.
  • the reaction liquid extraction speed may be set as appropriate according to the amount of raw material supplied.
  • the extraction rate of the reaction liquid is preferably 5 to 130 mass% / hour, more preferably 9 to 65 mass% / hour, based on the mass of the reaction liquid in the reactor.
  • the reaction proceeds at an appropriate raw material ratio, so that high-productivity and high-purity DAM can be produced.
  • the reaction liquid extracted from the reactor is supplied to one or more sealed finishing tanks, and then the pressure of the reaction liquid in the finishing tank is set to atmospheric pressure.
  • the finishing tank means a tank intended to remove methyl chloride present in the reaction liquid by lowering the pressure of the reaction liquid to atmospheric pressure and further aeration as necessary.
  • the reaction liquid extracted from the reactor may be directly processed in the finishing tank (see, for example, FIG. 3) or may be processed in the finishing tank through an aging tank described later. [0061] Since unreacted methyl chloride is dissolved in the reaction liquid in the reactor, it is hydrolyzed to hydrogen chloride, which is not preferable in terms of the quality of the final product.
  • the pressure inside the finishing tank is not particularly limited, but is preferably a pressure equal to or lower than the pressure in the reactor, more preferably atmospheric pressure to 0.7 MPaG, and still more preferably atmospheric pressure. . By setting the strength and the range, it is preferable because polymerization of DAM in the reaction solution can be prevented.
  • the pressure of the extracted reaction liquid can be lowered step by step, and the above problem can be solved.
  • Supply of the reaction solution to the finishing tank may be continuous or intermittent, but continuous supply is preferable because DAM can be stably produced.
  • a force S for blowing a gas containing at least oxygen into the reaction liquid transferred to the finishing tank can be achieved.
  • oxygen can be supplied to the reaction liquid in the finishing tank to prevent polymerization of DAM, and unreacted substances after the reaction, particularly methyl chloride, can be removed.
  • the gas air is usually used as long as it contains at least oxygen.
  • the number of finishing tanks may be at least one, but from the viewpoint of removal of methyl chloride, a larger number of tanks is preferable.
  • the number of finishing tanks is usually 1 or more, preferably 2 or more, more preferably 3 or more.
  • the size, material and structure of the finishing tank may be appropriately selected according to the purpose such as the raw materials used and the production amount of DAM. Specifically, the same ones as exemplified in the reactor can be used.
  • DAM is 60 to 80% by mass. In this case, it is preferable to add water in the finishing tank to obtain a final product concentration.
  • Aging tank In the present invention, it is preferable to supply the reaction liquid continuously extracted from the reactor to one or more sealed aging tanks.
  • the aging tank is a tank that is higher than the reaction rate of DAM in the reaction liquid extracted from the reactor! Usually, the reactor, the aging tank and the finishing tank are connected in this order.
  • the pressure in the aging tank is maintained at a pressure lower than the pressure in the reactor, and the temperature in the aging tank is set to a temperature equal to or lower than the temperature in the reactor to ripen the reaction. be able to.
  • the reaction can be sufficiently advanced in the aging tank, and each unreacted raw material is contained in the product. It is preferable because it can be prevented from remaining in the substrate.
  • the reaction solution may be supplied to the aging tank continuously or intermittently. However, continuous supply is preferable because DAM can be stably produced.
  • the pressure in the aging tank is usually lower than the pressure in the reactor, and when an aging tank is used, it can be set to atmospheric pressure in the aging tank.
  • the pressure is preferably atmospheric pressure to 0.8 MPaG, more preferably atmospheric pressure to 0.6 MPaG.
  • the temperature in the aging tank is usually 30 to 60 ° C., preferably below the temperature in the reactor. Furthermore, it is preferable to keep the pressure in the aging tank at a constant pressure, and it is preferable to keep the temperature in the aging tank constant.
  • reaction liquid it is preferable to supply the reaction liquid to the finishing tank after supplying the reaction liquid to the aging tank and aging the reaction liquid. In this case, it is preferable to gradually reduce the pressure in the reactor, the aging tank and the finishing tank. As a result, it is possible to prevent the polymerization of DAM caused by methyl chloride and oxygen dissolved in the reaction solution being volatilized at once and the reaction solution becoming a low oxygen state.
  • atmospheric pressure is used in the aging tank, only aeration and water addition need be performed in the finishing tank.
  • the number of aging tanks may be at least one, but from the viewpoint of improving productivity, a larger number of tanks is preferable.
  • the number of aging tanks is usually 1 or more, preferably 2 or more, more preferably 3 or more.
  • the first aging tank is preferably 0.05 to 0.8 MPaG
  • the second aging tank is preferably set to atmospheric pressure to 0.5 MPag.
  • the size, material and structure of the aging tank may be appropriately selected according to the purpose, such as the raw materials used and the production volume of DAM. Specifically, the same ones as exemplified in the reactor can be used.
  • the residence time ([reaction liquid mass] / [reaction liquid extraction speed (mass / hour)]) in the present invention can be set in various ranges depending on the reaction conditions, the number of finishing tanks and aging tanks, and the like.
  • the residence time is usually 4 hours or longer, preferably 4.5 hours or longer, more preferably 5 hours or longer.
  • the residence time is usually 1 hour or longer, preferably 1.5 hours or longer, more preferably 2 hours or longer, more preferably 2 to; 15 hours.
  • the residence time is usually 1500 ppm or less, preferably ⁇ 1200 ppm or less, and more preferably ⁇ 1000 ppm or less.
  • DAC dimethylaminoethyl acrylate
  • reaction tank 8 As the reaction tank 8, the ripening tank B, and the finishing tank C, a 10m 3 tank reactor equipped with a stirrer inside, attached with an external jacket (not shown), and glass-lined on the inner wall surface is used. did.
  • Methyl chloride (6) through the supply pipe (3) into the sealed reaction tank (6) via the suction part (9) of (11) (Hereinafter abbreviated as “MC”).
  • MC was continuously supplied at a supply rate of 410 kg / hour, and the amount consumed by the reaction was supplied so that the pressure inside the reaction tank A was maintained at 0.28 MPaG.
  • DA dimethylaminoethyl acrylate
  • reaction solution in reaction tank A is continuously withdrawn into aging tank B through a transfer pipe (4 '). 0.
  • Depressurized to 12 MPaG and further from aging tank B C was continuously extracted through a transfer pipe (12).
  • the pressure in finishing tank C is maintained at atmospheric pressure, and at the same time, air is blown into the reaction liquid in finishing tank C to remove excess MC dissolved in the reaction liquid, so that the product concentration is 79%. Water was continuously supplied to finishing tank C at 95 kg / hour.
  • the total concentration of DAC, DA, and MC in reactor A was 81.0%, and the concentrations of MC and oxygen in the gas phase of reactor A were 46.1% and 6.5%, respectively. It was.
  • the total concentration is a calculated value from the charged amount, and the concentration in the gas phase is an analytical value by gas chromatography.
  • the content of acrylic acid (hereinafter abbreviated as “AA”) in the DAC aqueous solution as the final product was measured, and the state of the final product was visually observed.
  • the results are shown in Table 1.
  • the A A concentration is an analysis value by liquid chromatography.
  • the pure water supply in reaction tank A is 395 kg / hour (Example 2) and 260 kg / hour (Example 3), respectively, and the pure water supply in finishing tank C is Okg / hour (Example 2).
  • the DAC was continuously produced in the same manner and in the same amount as in Example 1 except that 135 kg / hour (Example 3) was used.
  • Table 1 shows the total concentration of DAC and DA in the reaction vessel, and the concentrations of MC and oxygen in the gas phase of the reaction vessel. [0084] The final product DAC aqueous solution was evaluated in the same manner as in Example 1. Table 1 shows the results.
  • a DAC was produced in the same manner and in the same manner as in Example 1 except that the amount of MC supplied in the reaction tank A was 435 kg / hour (Example 4) and 390 kg / hour (Example 5), respectively.
  • Table 1 shows the total concentration of DAC and DA in the reaction vessel, and the concentrations of MC and oxygen in the gas phase of the reaction vessel.
  • a DAC was produced in the same manner and in the same manner as in Example 1 except that the pure water supply in the reaction tank A was 200 kg / hour and the pure water supply in the finishing tank C was 195 kg / hour.
  • Table 1 shows the total concentration of DAC and DA in the reaction vessel, and the concentrations of MC and oxygen in the gas phase of the reaction vessel.
  • DAC could be stably produced, and the final product had a low AA concentration and excellent product quality.
  • Examples 1 to 5 are examples in which the amount of water supplied is within a more preferable range, and there was no load on the circulation pump.
  • Table 2 shows the total concentration of DAC and DA in the reaction vessel, and the concentrations of MC and oxygen in the gas phase of the reaction vessel.
  • Comparative Example 1 is an example in which [0] and [0] / [MC] in the gas phase part are less than the lower limit of the present invention.
  • the polymerization of DAC has occurred in a force reactor, which is an example where MC] slightly exceeds the upper limit of the present invention.
  • the DAM production method of the present invention can produce DAM with high productivity and high purity safely. Therefore, it is suitable for industrial scale DAM production.

Landscapes

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

Abstract

L'invention concerne un procédé destiné à produire un DAM à productivité et pureté élevées tout en garantissant la sécurité, par réglage de la composition du gaz dans une phase gazeuse d'un réacteur à une valeur entrant dans la fourchette prédéfinie. L'invention concerne, plus particulièrement, un procédé de production d'un sel quaternaire de (méth)acrylate de dialkylaminoalkyle par alimentation d'un (méth)acrylate de dialkylaminoalkyle, d'un chlorure de méthyle et d'eau dans un réacteur, la réaction étant réalisée lors du dosage de la concentration d'oxygène ([O2]), de la concentration de chlorure de méthyle ([MC]), et du taux de concentration d'oxygène par rapport à celui de chlorure de méthyle ([O2]/[MC]) dans la phase gazeuse du réacteur compris entre 3 et 12 vol%, 22 et 80 vol% et 0,05 et 0,5, respectivement.
PCT/JP2007/068521 2006-09-27 2007-09-25 Procédé de production de sel quaternaire de (méth)acrylate de dialkylaminoalkyle WO2008038619A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN2007800355933A CN101516828B (zh) 2006-09-27 2007-09-25 二烷基氨基烷基（甲基）丙烯酸酯季盐的制造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006263357A JP5207608B2 (ja) 2006-09-27 2006-09-27 ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法
JP2006-263357 2006-09-27

Publications (1)

Publication Number Publication Date
WO2008038619A1 true WO2008038619A1 (fr) 2008-04-03

Family

ID=39230055

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2007/068521 WO2008038619A1 (fr) 2006-09-27 2007-09-25 Procédé de production de sel quaternaire de (méth)acrylate de dialkylaminoalkyle

Country Status (4)

Country Link
JP (1) JP5207608B2 (fr)
CN (1) CN101516828B (fr)
TW (1) TW200815318A (fr)
WO (1) WO2008038619A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5732766B2 (ja) 2010-07-23 2015-06-10 トヨタ自動車株式会社 車両の制御装置および制御方法
JP6725864B2 (ja) * 2015-08-21 2020-07-22 Dic株式会社 活性エネルギー線硬化性組成物及びそれを用いたフィルム

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004155726A (ja) * 2002-11-07 2004-06-03 Mitsubishi Rayon Co Ltd 不飽和第四級アンモニウム塩の製造方法
JP2004155669A (ja) * 2002-11-01 2004-06-03 Toagosei Co Ltd ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0495053A (ja) * 1990-08-08 1992-03-27 Mitsubishi Gas Chem Co Inc 不飽和第４級アンモニウム塩水溶液の製造方法
JPH07206790A (ja) * 1994-01-20 1995-08-08 Mitsui Toatsu Chem Inc 不飽和第四級アンモニウム塩の製造方法
JP2004010508A (ja) * 2002-06-04 2004-01-15 Toagosei Co Ltd ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004155669A (ja) * 2002-11-01 2004-06-03 Toagosei Co Ltd ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法
JP2004155726A (ja) * 2002-11-07 2004-06-03 Mitsubishi Rayon Co Ltd 不飽和第四級アンモニウム塩の製造方法

Also Published As

Publication number Publication date
CN101516828A (zh) 2009-08-26
CN101516828B (zh) 2012-11-21
JP5207608B2 (ja) 2013-06-12
TW200815318A (en) 2008-04-01
JP2008081444A (ja) 2008-04-10

Similar Documents

Publication Publication Date Title
EP2526083B1 (fr) Production continue de sels quaternaires
CN108250176A (zh) 一种氟代碳酸乙烯酯的快速连续流合成工艺
US20230020208A1 (en) Organic acid and thermal treatment of purified 2,5-furandicarboxylic acid
CN104829495A (zh) 一种双组份溶剂制备高纯度高收率盐酸二甲双胍的方法
CN112678850A (zh) 一种六氟磷酸锂的生产装置及方法
WO2008038619A1 (fr) Procédé de production de sel quaternaire de (méth)acrylate de dialkylaminoalkyle
CN104557540A (zh) 一种丙烯酸羟基酯连续法清洁生产工艺
CN111825705B (zh) 一种三氟化硼二甲基硫醚络合物的制备方法
JP2023507469A (ja) 精製２，５－フランジカルボン酸の水及び熱による処理
CN111777506A (zh) 一种有机物溴乙酸及酯的绿色化学合成方法
EP2456751B1 (fr) Procédé de production d'un sel d'ammonium quaternaire insaturé
JP4062055B2 (ja) ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法
AU2017200997A1 (en) Process for preparing choline hydroxide from trimethylamine and ethylene oxide
JP2008081443A (ja) ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法及びその製造装置
CN106916068A (zh) 一种简单便捷的苯扎氯铵生产方法
CN104974126B (zh) 一种原位氧化环己酮制备ε-己内酯的方法
CN108164416A (zh) 一种基于生物柴油制备壬二酸单甲酯的新工艺
JP4178837B2 (ja) ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法
CN113061076A (zh) 一种氯代特戊烷的制备方法
CN104744275A (zh) 一种季铵盐型阳离子单体水溶液的制备方法
JP2004010508A (ja) ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法
CN107266324A (zh) 一种2‑氨基‑3‑氯苯甲酸甲酯的合成方法
CN118108631A (zh) 一种制备异丙基异氰酸酯的方法
CN109912441A (zh) 高纯度2,5-二苯胺基对苯二甲酸的制备方法
CN106800299A (zh) 高纯三氟化硼快速制备工艺及回收精制方法

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200780035593.3

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07828338

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 07828338

Country of ref document: EP

Kind code of ref document: A1