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WO2008018121A1 - Procédé servant à produire un composé 2-hydroxyester - Google Patents

Procédé servant à produire un composé 2-hydroxyester Download PDF

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Publication number
WO2008018121A1
WO2008018121A1 PCT/JP2006/315684 JP2006315684W WO2008018121A1 WO 2008018121 A1 WO2008018121 A1 WO 2008018121A1 JP 2006315684 W JP2006315684 W JP 2006315684W WO 2008018121 A1 WO2008018121 A1 WO 2008018121A1
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WIPO (PCT)
Prior art keywords
water
atom
organic solvent
hydroxyester compound
carbon atoms
Prior art date
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Ceased
Application number
PCT/JP2006/315684
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English (en)
Japanese (ja)
Inventor
Ichiro Kozono
Hajime Mori
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Nippoh Chemicals Co Ltd
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Nippoh Chemicals Co Ltd
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Priority to PCT/JP2006/315684 priority Critical patent/WO2008018121A1/fr
Publication of WO2008018121A1 publication Critical patent/WO2008018121A1/fr
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
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment

Definitions

  • the present invention removes a reaction liquid ammonia salt containing 2-hydroxyester compound and an ammonia salt alcohol and the like, and efficiently purifies the 2-hydroxyester compound.
  • the present invention relates to a method for producing a 2-hydroxyester compound.
  • 2-Hydroxyester compounds are industrially important compounds as intermediates for raw materials for pharmaceuticals and agricultural chemicals and photographic materials.
  • starting materials there are a method using amide, alcohol and formic acid ester, a method using 2-hydroxycarboxylic acid and alcohol, and a method using cyanohydrin and alcohol.
  • cyanohydrin can be easily prepared from aldehyde and hydrocyanic acid, various methods for producing 2-hydroxy ester compounds starting from cyanohydrin have been proposed! Speak.
  • a ketone cyanohydrin and sulfuric acid are reacted to esterify the reaction product and an alcohol, and an anhydrous sulfate such as an alkali metal is added thereto to add a 2-hydroxy fatty acid ester.
  • an anhydrous sulfate such as an alkali metal
  • ammonium sulfate is used depending on the type of acid used.
  • Ammonium, ammonium nitrate, ammonium phosphate, ammonium chloride are by-produced.
  • a method for fractionating such ammonium salt for example, a method in which sodium sulfate is added to a reaction liquid slurry containing ammonium salt, alcohol, 2-hydroxyester, etc., and 2-hydroxyester is recovered by distillation. (U.S. Pat. No. 20,418,820) and a method of solid-liquid separation of a reaction liquid slurry (Japanese Patent Laid-Open No. 4-230241).
  • MHBA 2-hydroxybutanoic acid methyl
  • MHBA dissolves ammonia salts such as ammonium chloride. Therefore, the filtrate after the solid-liquid separation contains a considerable amount of salt ammonia.
  • the filtrate is heated to purify MHBA by distillation, MHBA undergoes thermal decomposition due to the presence of salt ammonium and the yield decreases. Also, in order to improve the yield, a large amount of solvent is required when trying to drain the MHBA contained in the solid ammonium liquid solid-liquid separated.
  • the present invention provides a reaction solution slurry force containing ammonia salt, alcohol, 2-hydroxyester, etc. 2-hydroxyester compound that removes ammonia salt by a simple method.
  • the manufacturing method of a thing is provided.
  • the present invention suppresses dissolution of a 2-hydroxyester compound in a separated water layer in a method for producing a relatively high water-soluble 2-hydroxyester compound such as MHBA. It is possible to provide a method for efficiently recovering the 2-hydroxyester compound in the separated water layer.
  • the present invention is a method for producing a 2-hydroxyester compound, which comprises the 2-hydroxyester compound, an alcohol, an organic solvent, and an ammonium salt.
  • a step of distilling alcohols from the solution a step of adding water to the residual liquid obtained in the step of distilling off the alcohols to separate the organic solvent layer and the aqueous layer, and an organic matter obtained in the step of separating.
  • This is a method for producing a 2-hydroxyester compound, which comprises the step of distilling the solvent layer to purify the 2-hydroxyester compound.
  • the 2-hydroxyester compound and the ammonium salt can be easily separated. Since the obtained organic solvent layer has a small amount of ammonium salt, a 2-hydroxyester compound can be easily produced in a high yield by distillation.
  • the 2-hydroxyester compound contained in the aqueous layer after the two-layer separation can be recovered together with water by distillation under specific conditions. If this is reused in the purification process, the recovery rate can be further improved.
  • a first aspect of the present invention is a process for producing a 2-hydroxyester compound represented by the general formula (1), wherein the 2-hydroxyester compound, the alcohol, the organic solvent, and the ammonia- A process of distilling off alcohol, which is a mixed liquid containing um salt,
  • Water is added to the residual liquid obtained in the step of distilling off the alcohols to obtain an organic solvent layer and an aqueous layer. Separating into, and
  • R 1 is a hydrogen atom, a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 12 carbon atoms and including an oxygen atom, a sulfur atom, or a nitrogen atom, or 3 to 3 carbon atoms. 6 or a substituted or unsubstituted alicyclic hydrocarbon group which may contain an oxygen atom, a sulfur atom or a nitrogen atom, or has 3 to 14 carbon atoms and contains an oxygen atom, a sulfur atom or a nitrogen atom
  • R 2 is an alkyl group which has 1 to 12 carbon atoms and may contain an oxygen atom, a sulfur atom or a nitrogen atom.
  • the 2-hydroxyester compound in the mixed solution is distilled as it is, the 2-hydroxyester compound is decomposed by the ammonium salt contained in the mixed solution in a slurry state. Therefore, alcohols are removed from the liquid mixture by distillation in advance, ammonia salts, etc. are removed by adding two layers by adding water, and then an organic solvent containing only the 2-hydroxyester compound is recovered. To do. When the organic solvent is distilled, the decomposition of the 2-hydroxyester compound can be suppressed and a 2-hydroxyester compound can be produced.
  • the present invention will be described in detail.
  • the object of the present invention is a 2-hydroxyester compound represented by the general formula (1).
  • the 2-hydroxyester compound is produced by using an alcohol on a cyanohydrin shown below.
  • R 1 is a hydrogen atom, a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may contain an oxygen atom, a sulfur atom, or a nitrogen atom, or 3 to 3 carbon atoms. 6 Substituted or unsubstituted alicyclic hydrocarbon group which may contain oxygen atom, sulfur atom or nitrogen atom, or has 3 to 14 carbon atoms and may contain oxygen atom, sulfur atom or nitrogen atom, substituted Alternatively, it represents an unsubstituted aryl group or aralkyl group.
  • the mixed solution used in the present invention is prepared by any reaction system as long as it contains the above-mentioned 2 hydroxyester compound, alcohol, organic solvent, and ammonium salt. May be.
  • the ammonium salt is not limited to the case where it is a by-product of the production process of the 2-hydroxyester compound.
  • an ammonium salt is by-produced in the process of producing cyanohydrin, and cyanohydrin containing such an ammonium salt is used as a raw material, such a reaction solution used in the present invention has such a reaction.
  • Ammonium salt of origin may be included. Therefore, ammonium salts such as ammonium sulfate, ammonium nitrate, ammonium chloride, and ammonium phosphate can be targeted.
  • the organic solvent contained in the mixed solution is an inert solvent that does not cause a side reaction when the alcohols are distilled off, and a solvent having a solubility in water of 8% by mass or less is used.
  • aromatic hydrocarbons having 6 to 12 carbon atoms such as benzene, toluene, xylene and black benzene
  • aliphatic hydrocarbons having 6 to 18 carbon atoms such as hexane and heptane, ethyl acetate, butyl acetate, etc.
  • esters such as jetyl ether, methyl t-butyl ether, and chlorinated hydrocarbons such as methylene chloride and chloroform. Since both are reaction-inert solvents, the degradation of cyanohydrin, which is an unstable raw material, can be suppressed. Moreover, since the solubility with respect to water is low, two-layer separation with an aqueous layer is easy. In addition, since the target 2-hydroxyester compound is excellent in solubility, it can be easily separated from the ammonium salt.
  • esters such as jetyl ether, methyl t-butyl ether, and chlorinated hydrocarbons such as methylene chloride and chloroform. Since both are reaction-inert solvents, the degradation of cyanohydrin, which is an unstable raw material, can be suppressed. Moreover, since the solubility with respect to water is low, two-layer separation with an aqueous layer is easy. In addition, since the target 2-hydroxyester compound is excellent in solubility, it can
  • the composition of the mixed solution used in the present invention is different in the reaction system as described above and is intended to produce 2-hydroxy ester compound, and therefore, generally, an organic solvent and 2-
  • the weight ratio with respect to the hydroxy ester compound is preferably 1:10 to L0: 1, more preferably 1: 3 to 3: 1.
  • the ratio of 2-hydroxyester compounds contained in the aqueous layer is sufficiently low in the separation step because the amount of 2-hydroxyester compounds is less than the weight ratio of 1:10. Therefore, recovery of the 2-hydroxyester compound is facilitated. Further, when the 2-hydroxyester compound is more than the weight ratio of 10: 1, the amount of the organic solvent is relatively small, so that productivity is improved and the recovery cost of the organic solvent can be kept low. .
  • the weight ratio of the slightly water-soluble organic solvent to the ammonium salt is preferably 1:10 to: L0: 1, more preferably 1: 5 to 5: 1. Particularly preferred is 1: 3 to 3: 1.
  • the weight ratio of alcohols to organic solvent is preferably 10: 1 to 1:10, more preferably 5: 1 to 1: 5, particularly preferably 3: 1 to 1: 3. Alcohol strength When the ratio is less than 10: 1 with respect to the organic solvent, the operability in the step of distilling off alcohols is improved, and the recovery cost of alcohols is further reduced. Further, it is preferable that the amount of alcohol is more than 1:10 with respect to the organic solvent because the yield of 2-hydroxyester is increased and the recovery cost of the organic solvent can be suppressed.
  • an organic solvent can be added during the reaction or after the reaction to obtain the above mixed solution.
  • the mixed solution that can be used in the present invention include the reaction solution obtained in the above-mentioned US Pat. No. 20,41820, JP-A-4-230241, JP-A-6-247896, and the like, and further an organic solvent, etc. There is what added.
  • a method for producing a 2-hydroxyester compound containing an ammonium salt used in the present invention is not particularly limited, but an acid is mixed with a mixture of cyanohydrin, a corresponding alcohol, a solvent and water.
  • the reaction solution thus obtained was mixed with the 2-hydroxyester compound, alcohol It can be used as a mixed solution containing alcohols, organic solvent, and ammonium salt.
  • the reaction solution can be prepared simply by charging cyanohydrin, alcohol, solvent, and water, then mixing the acid and heating, eliminating the need for operations such as solid-liquid separation, distillation, and concentration for intermediate separation.
  • a pressure reaction device such as autoclave is not necessary, and it can be easily prepared.
  • the yield of ester candy is high.
  • a 2-hydroxyester compound is produced in one step without adding an acid to the mixture obtained by adding the above alcohol, solvent and water to the above cyanohydrin.
  • the acid to be used is not particularly limited, and examples thereof include inorganic acids such as hydrogen chloride gas, hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid, and organic acids such as p-toluenesulfonic acid, methanesulfonic acid, formic acid and acetic acid.
  • a solvent which is inert to the reaction and has a solubility in water of 8% by mass or less can be used.
  • benzene, toluene, xylene, black benzene and the like have 6 carbon atoms.
  • aromatic hydrocarbons having 6 to 12 carbon atoms More preferred are aromatic hydrocarbons having 6 to 12 carbon atoms, saturated aliphatic hydrocarbons having 6 to 18 carbon atoms, and chlorinated hydrocarbons.
  • toluene since the solubility of the 2-hydroxyester compound is high and the solubility in water is low, and furthermore, the recovery is easy and it is inert.
  • Esters such as ethyl acetate and butyl acetate are active under the reaction conditions, and side reactions such as hydrolysis and transesterification may occur.
  • the concentration of cyanohydrin contained in the solvent varies depending on the amounts of water and alcohol to be added, but is generally preferably 5.0 to 60.0% by mass, more preferably 20.0% in the mixed solution. -40. 0 mass 0/0, particularly preferably at 26. 0-37. 0 wt 0/0. 60.
  • 0 mass 0/0 Ru exceeded solid content formed during Iminoeterui spoon is too large, the stirring of the slurry It becomes difficult. On the other hand, if it is less than 5.0% by mass, the solvent recovery step becomes complicated and disadvantageous.
  • the alcohol to be added is theoretically 1 to 5 mol, more preferably 1.5 to 4 mol, especially considering the force reaction yield of 1 mol per 1 mol of cyanohydrin. Preferably it is 2-4 mol. If the amount is less than 1 mol, the yield decreases. On the other hand, if the amount exceeds 5 mol, the operation for removing the excessively added alcohol becomes complicated and disadvantageous.
  • water is preferably from 0.7 to 2 monolayer, more preferably from 0.8 to 8 1.5 monole, particularly preferably ⁇ or 0.8 to 1.2 mol. If the amount is less than 0.7 mol, the yield decreases. On the other hand, if it exceeds 2 mol, the yield decreases, which is disadvantageous.
  • concentration of the cyanohydrin in the mixed solution can be adjusted by appropriately selecting the amount of solvent in consideration of the water and alcohol to be added.
  • the acid to be used is preferably 1 to 1.5 mol, more preferably 1.05 to L 25 mol per 1 mol of cyanohydrin. If the amount is less than 1 mol, the reaction promoting effect decreases, whereas if it exceeds 1.5 mol, the yield decreases, which is disadvantageous.
  • the acid contained in the molecule for example, nitrogen atom of amine in the molecule
  • an acid capable of forming a salt are not included in the above-mentioned introduction amount of the acid.
  • the liquid temperature at the time of acid introduction is preferably 0 to 80 ° C, more preferably 25 to 60 ° C, and particularly preferably 35 to 45 ° C. Below 0 ° C, the reaction time becomes longer, which is disadvantageous. On the other hand, if it exceeds 80 ° C, the raw material alcohol and acid may react to form a by-product, which is disadvantageous. When using an aqueous hydrochloric acid solution as the acid, it is preferable to adjust the temperature to the above temperature range.
  • the introduction time of the acid can be arbitrarily selected depending on the productivity and the heat removal efficiency of the reaction heat, but is 1 to 20 hours, particularly 1 to 15 hours.
  • the reaction solution is allowed to react for 0 to 20 hours in the range of 0 ° C to reflux temperature under normal pressure.
  • the ability to obtain the target 2-hydroxyester compound is obtained at different temperatures.
  • the reaction solution is aged at a temperature ranging from 0 ° C to the reflux temperature under normal pressure, preferably 35-45 ° C, more than 0 hours and 4 hours or less, more preferably 1-2 hours. . This is referred to as first aging.
  • the weight ratio of the components in the reaction solution obtained by the above method is preferably 1: 6 to 3: 1, more preferably 2: 3 to 5: the weight ratio of the organic solvent to the 2-hydroxyester compound. 3. Particularly preferred is 5: 6 to 5: 4.
  • the weight ratio of the organic solvent to the ammonium salt is preferably 1: 3 to 6: 1, more preferably 4: 3 to: LO: 3, particularly preferably 5: 6 to 5: 4.
  • the ratio of alcohols to organic solvent is preferably 5: 1 to 1:10, more preferably 1: 1 to 1:10.
  • alcohols are distilled off from the mixed solution containing the 2-hydroxyester compound and the ammonium salt.
  • the 2-hydroxyester compound can be produced with high purity from the organic solvent in the purification step of the 2-hydroxyester compound.
  • the distillation should be carried out under conditions that allow the alcohols to be distilled.
  • the distillation temperature is preferably 60 to 130 ° C, more preferably. 60 to 100 ° C, particularly preferably 70 to 90 ° C.
  • the alcohol when it is methanol or ethanol contained in the mixed solution, it can be easily distilled from the mixed solution within the above temperature range. If the temperature exceeds 130 ° C, the 2-hydroxyester compound contained in the mixed solution may be decomposed by the action of water or ammonia salt, which is disadvantageous. Excessive decompression conditions are required.
  • the pressure is within a known range as long as the alcohol can be distilled!
  • the alcohol distilled off in the step of distilling off the alcohol is 2-hydroxyl It can also be used as a raw material for the production of steril compounds.
  • Water is added to the residual liquid after the alcohols are distilled off to separate the organic solvent layer and the aqueous layer.
  • Simply separating the ammonium salt contained in the residual liquid by solid-liquid separation does not prevent the ammonium salt from dissolving in the organic solvent, but after adding water, the organic solvent layer and the aqueous layer are separated. By separating into two layers, the concentration of ammonia salt contained in the organic solvent can be efficiently reduced.
  • the 2-hydroxyester compound is mainly dissolved, and in the aqueous layer, a part of the 2-hydroxyester compound in which the ammonium salt is mainly dissolved is also included in the aqueous layer.
  • the ammonium salt contained in the residual liquid is insoluble in the organic solvent, the ammonium salt is dissolved in water by adding force water that exists in the form of a slurry in the residual liquid. Therefore, the organic solvent power can also remove ammonia salts. Therefore, the amount of water to be added needs to be an amount sufficient to dissolve the contained ammonium salt and can be separated into two layers with an organic solvent. Preferably, it is 2.6 to 5.0 mass times, more preferably 2.6 to 3.0 mass times, and particularly preferably 2.6 to 2.8 mass times that of salt ammonium. Since 2-hydroxy ester compound is soluble in water, the recovery rate of 2-hydroxy ester compound may decrease if the amount of water added exceeds 5.0 mass times. On the other hand, when the amount is less than 2.6 mass times, the ammonium salt is not completely dissolved, resulting in an obstacle to the liquid separation operation.
  • water is preferably added when the temperature is 70 ° C or lower, more preferably 40 ° C or lower. . If water is added above 70 ° C, the 2-hydroxyester compound may be hydrolyzed by water due to the effect of temperature.
  • the temperature of water to be added is not limited, but is preferably 0 to 40 ° C, more preferably 20 to 40 ° C. If the temperature of the added water exceeds 40 ° C, depending on the pH of the reaction solution, the 2-hydroxyester compound may be hydrolyzed by water. On the other hand, below 0 ° C, the solubility of ammonia salt may decrease.
  • the water in the kettle may be neutralized after the addition of water.
  • the pH of the liquid in the kettle is preferably 3 to 9, more preferably 5 to 8, particularly preferably 6.5 to 7.5. If the pH exceeds 9, Hydrolysis can occur even at warm temperatures.
  • the pH in the present invention refers to the pH at a temperature of 25 ° C.
  • the organic solvent layer after the two-layer separation obtained in the step (3) is distilled to produce a 2-hydroxyester compound. Since the solvent layer is one in which the content of water and ammonia salt is extremely reduced by the step (3) above, the organic solvent layer is heated to the distillation temperature of the 2-hydroxyester compound. However, they are not hydrolyzed by these, and the 2-hydroxyester compound can be produced with high yield.
  • the water layer separated in the above two-layer separation process also contains a force-soluble 2-hydroxyester compound containing an ammonium salt.
  • a force-soluble 2-hydroxyester compound containing an ammonium salt In the present invention, it is confirmed that the pH of the aqueous layer is 3 to 8, and after adjusting to Z or PH 3 to 8, the aqueous layer is distilled to recover water and 2 hydroxyester compound. To do.
  • the water layer also contains a water-soluble 2-hydroxyester compound, discarding the water layer as it is decreases the yield.
  • the 2-hydroxyester compound is easily hydrolyzed by heating, and the recovery efficiency decreases.
  • an acid is often added to the reaction system for hydrolysis, and the resulting aqueous layer may be strongly acidic. It is hydrolyzed by heating.
  • the present inventors have found that when the pH of the aqueous layer is adjusted to 3 to 8, decomposition of the 2-hydroxyester compound can be avoided even under heating conditions.
  • P H of the aqueous layer more preferably 4-7, particularly preferably 5-6.
  • the pH of the aqueous layer is not limited in time if it is adjusted before distillation.
  • sodium hydroxide or the like is added to the mixed solution before the alcohol is distilled off.
  • the pH may be adjusted to 3-8, or when adding water to the residual liquid after the alcohol has been distilled off, or before adding water to the residual liquid.
  • the two-layer separated aqueous layer can be adjusted to pH 3-8.
  • Sodium, potassium hydroxide or alkali metal or alkaline earth metal carbonates, organic acid salts such as sodium acetate, and phosphates can be used. If the pH of the aqueous layer shows pH 3 to 8 without any adjustment, just distill it as is!
  • water and the 2-hydroxyester compound are also recovered by distillation.
  • the 2-hydroxyester compound may be recovered alone, but when the 2-hydroxyester compound forms an azeotropic composition with water, the two are recovered by azeotropic distillation.
  • the distillation conditions are such that hydrolysis of the 2-hydroxyester compound can be avoided and that strong water and the 2-hydroxyester compound can be azeotroped, for example, at a temperature of 10 ° C. Distill at ⁇ 100 ° C, more preferably 20 ° C-90 ° C, particularly preferably 30 ° C-80 ° C.
  • the pressure is normal pressure or lower, preferably 1.2 kPa to 101.3 kPa, more preferably 2.3 kPa to 70.1 kPa, particularly preferably 4.2 kPa to 47.4 kPa.
  • the 2-hydroxy ester compound shown by the general formula (1) Contact !, Te, R 1 and R 2 are methyl or Echiru, these 2-hydroxy ester Louis ⁇ was and high water-solubility This is preferred because it easily forms an azeotropic composition with water.
  • distillate is reused in the following two-layer separation step in the following production process, water can be reused as added water, and the 2-hydroxyester compound is obtained.
  • the yield can be improved because it is not discarded but reused in the manufacturing process.
  • the 2-hydroxyester compound represented by the general formula (1) is mixed with a mixture containing a 2-hydroxyester compound, an alcohol, an organic solvent, and an ammonium salt.
  • Ammonium salt can also be separated efficiently and easily in terms of liquid mixture power. After obtaining an organic solvent that mainly dissolves the 2-hydroxyester compound, this is distilled to easily produce the target product. Can do.
  • the production method of the present invention can be applied regardless of the reaction step of the 2-hydroxyester compound, and it is particularly easy to prepare a reaction solution containing an organic solvent and add water thereto. In addition, it can be used to dissolve ammonium salt in the water layer, so its application range is wide.
  • the liquid in the container was cooled to 40 ° C, and 314 g of water and 4.2 g of sodium hydroxide were added. As a result, the pH of the liquid water layer in the container was adjusted to 7.1, and the salt ammonia was dissolved in water.
  • a 500 mL container having a stirrer, a thermocouple thermometer, a heat exchanger for vapor condensing, a container for receiving a distillate, and a pipe connected to a vacuum pump was obtained in the above two-layer separation process.
  • the entire layer was charged and the pressure in the distillation system was reduced to 26.7 kPa.
  • the liquid in the container was heated and toluene was recovered by distillation. Then, it was once cooled and the pressure in the distillation system was reduced to 2.7 kPa.
  • the solution in the container was heated to the heat and distilled to obtain 107.6 g of methyl 2-hydroxybutanoate.
  • the yield of methyl 2-hydroxybutanoate by the above process was 51.3%. Separate the separated aqueous and organic layers The total yield of methyl 2-hydroxybutanoate obtained was 72.2%.
  • the liquid in the container was cooled to 40 ° C, and 237 g of water and 3.6 g of sodium hydroxide were added. As a result, the pH of the liquid aqueous layer in the container was adjusted to 5.3, and the salt ammonia was dissolved in water.
  • a 300 mL container having a stirrer, a thermocouple thermometer, a heat exchanger for vapor condensing, a container for receiving a distillate, and a pipe connected to a vacuum pump was obtained in the above two-layer separation process.
  • the entire layer was charged and the pressure in the distillation system was reduced to 26.7 kPa.
  • the liquid in the container was heated and toluene was recovered by distillation. Then, it was once cooled and the pressure in the distillation system was reduced to 2.7 kPa.
  • the yield of methyl 2-hydroxybutanoate by the above process was 47.8%.
  • a 600 mL container having a stirrer, a thermocouple thermometer, a heat exchanger for steam condensation, a container for receiving a distillate, and a pipe connected to a vacuum pump was obtained in the above two-layer separation process. All the layers were charged. The pressure in the distillation system was reduced to 26.7 kPa, and the liquid in the vessel was heated to collect toluene by distillation. Then, it was once cooled and the pressure in the distillation system was reduced to 2.7 kPa. The solution in the container was heated to distillation to obtain methyl 2-hydroxybutanoate by distillation. The yield of methyl 2-hydroxybutanoate by the above process was 25.7%. The total yield of methyl 2-hydroxybutanoate obtained by distilling the separated aqueous layer and organic layer was 38.0%.
  • the present invention relates to a method for producing a 2-hydroxyester from a reaction solution containing an ammonium salt, and is a simple and excellent method for producing a 2-hydroxyester, which is useful.

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

Abstract

L'invention concerne un procédé servant à produire un composé 2-hydroxyester avec un rendement de production élevé à partir d'un mélange réactionnel liquide contenant un sel d'ammonium. La présente invention concerne donc un procédé servant à produire un composé 2-hydroxyester représenté par la formule générale (1) lequel comprend : l'étape consistant à enlever par distillation un alcool d'un mélange liquide contenant le composé 2-hydroxyester décrit ci-dessus, l'alcool, un solvant organique et un sel d'ammonium ; l'étape consistant à ajouter de l'eau au résidu liquide obtenu dans l'étape d'élimination de l'alcool par distillation et à séparer ensuite le mélange en une phase de solvant organique et une phase aqueuse ; et l'étape consistant à distiller la phase de solvant organique obtenue dans l'étape de séparation pour de cette manière purifier le composé 2-hydroxyester. [Formule chimique 1] R1-CH(OH)-COOR2 (1) Dans la formule, R1 représente un atome d'hydrogène, un groupe hydrocarboné aliphatique substitué ou non substitué ayant de 1 à 12 atomes de carbone et contenant éventuellement un atome d'oxygène, un atome de soufre ou un atome d'azote, un groupe hydrocarboné alicyclique substitué ou non substitué ayant de 3 à 6 atomes de carbone et contenant éventuellement un atome d'oxygène, un atome de soufre ou un atome d'azote, ou un groupe aryle ou aralkyle substitué ou non substitué ayant de 3 à 14 atomes de carbone et contenant éventuellement un atome d'oxygène, un atome de soufre ou un atome d'azote ; et R2 représente un groupe alkyle ayant de 1 à 12 atomes de carbone et contenant éventuellement un atome d'oxygène, un atome de soufre ou un atome d'azote.
PCT/JP2006/315684 2006-08-08 2006-08-08 Procédé servant à produire un composé 2-hydroxyester Ceased WO2008018121A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004534040A (ja) * 2001-05-21 2004-11-11 フェルメンタ・バイオテック・リミテッド ２−ヒドロキシ−４−フェニル酪酸エステルの立体選択的合成
JP2006219421A (ja) * 2005-02-10 2006-08-24 Nippo Kagaku Kk ２−ヒドロキシエステル類の製造方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004534040A (ja) * 2001-05-21 2004-11-11 フェルメンタ・バイオテック・リミテッド ２−ヒドロキシ−４−フェニル酪酸エステルの立体選択的合成
JP2006219421A (ja) * 2005-02-10 2006-08-24 Nippo Kagaku Kk ２−ヒドロキシエステル類の製造方法

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