JP2015151400A - Method for producing organic compound, and method for producing ester - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for producing organic compounds which can promote the reaction of a substance.SOLUTION: A method for producing organic compounds comprises: a mixing step of mixing a first liquid and a second liquid which are not mixed each other; and a reaction step of producing the emulsion of the first and second liquids by irradiating the mixed solution mixed in the mixing step with a microwave and an ultrasonic wave to react a first substance contained in the first liquid with a second substance contained in the second liquid.

Description

  The present invention relates to a method for producing an organic compound and a method for producing an ester in which substances are reacted by irradiation with microwaves and ultrasonic waves.

  Conventionally, when an ester is produced by an esterification reaction or the like and raw materials are immiscible with each other, the reaction is performed while stirring using a magnetic stirrer or the like (for example, Patent Document 1). reference).

International Publication No. WO2007 / 088702

  The present invention provides a method for producing an organic compound and a method for producing an ester, which can further accelerate the reaction when reacting substances contained in liquids that are immiscible with each other, such as fat and alcohol. Objective.

  The present inventors have found that the reaction of substances contained in both liquids can be promoted by irradiating microwaves and ultrasonic waves to liquids that are not miscible with each other after intensive research on the above-mentioned problems, The invention has been completed.

That is, the present invention is as follows.
[1] By irradiating the first liquid and the second liquid, which are immiscible liquids, with microwaves and ultrasonic waves, the first substance contained in the first liquid, and the second liquid The manufacturing method of the organic compound which makes the 2nd substance contained in the liquid react.

[2] The organic material according to [1], wherein emulsions of the first and second liquids are generated by irradiation with microwaves and ultrasonic waves, and the first substance and the second substance are reacted. Compound production method.

[3] The first liquid is a hydrophilic liquid,
The method for producing an organic compound according to [1] or [2], wherein the second liquid is a lipophilic liquid.

[4] The method for producing an organic compound according to any one of [1] to [3], wherein the reaction is one or more reactions selected from the group consisting of a substitution reaction, an addition reaction, an elimination reaction, and a rearrangement reaction. .

[5] A method for producing an ester using the method for producing an organic compound according to [3],
The first substance is an organic compound having a hydroxyl group,
The second substance is an acid or an ester;
In the reaction, an ester is produced by synthesizing the organic compound having a hydroxyl group and the acid or ester to produce an ester.

[6] The first substance is an organic compound having an alcoholic hydroxyl group,
The second substance is an ester;
In the reaction, the ester is produced by transesterifying the organic compound having an alcoholic hydroxyl group and the ester to produce an ester.

[7] The second substance is a fatty acid ester,
The method for producing an ester according to [6], wherein in the reaction, the organic compound having the alcoholic hydroxyl group and the fatty acid ester are transesterified to produce a fatty acid ester.

[8] The first substance is a sugar,
In the reaction described above, the method for producing an ester according to [7], wherein the sugar and the fatty acid ester are transesterified to produce a sugar fatty acid ester.

[9] The first substance is sucrose,
In the reaction, the ester production method according to [8], wherein the sucrose and the fatty acid ester are transesterified to produce a sucrose fatty acid ester.

[10] The first substance is an organic compound having an alcoholic hydroxyl group,
The second substance is an acid;
The method for producing an ester according to [5], wherein in the reaction, an ester is produced by esterifying the organic compound having an alcoholic hydroxyl group and the acid.

[11] The second substance is a fatty acid,
The method for producing an ester according to [10], wherein in the reaction, the organic compound having the alcoholic hydroxyl group and the fatty acid are esterified to produce a fatty acid ester.

[12] The first substance is a sugar,
The method for producing an ester according to [11], wherein in the reaction, a sugar fatty acid ester is produced by esterifying the sugar and the fatty acid.

[13] The first substance is sucrose,
The method for producing an ester according to [12], wherein in the reaction, the sucrose and the fatty acid are esterified to produce a sucrose fatty acid ester.

[14] The method for producing an organic compound according to [1] or [2], wherein the reaction is an ion exchange reaction.

[15] The method for producing an organic compound according to any one of [1] to [4], wherein the reaction is performed in a flow reactor.

  According to the method for producing an organic compound according to the present invention, the reaction can be further promoted.

Diagram showing the configuration of the chemical reactor Diagram showing an example of the internal configuration of the reactor Graph showing the yield of sucrose fatty acid ester

  A mixing step of mixing the first liquid and the second liquid, which are immiscible liquids, and irradiating the first and second liquids mixed in the mixing step with microwaves and ultrasonic waves; A synthesis reaction method comprising a reaction step of reacting a first substance contained in the first liquid with a second substance contained in the second liquid, and production of an ester using the synthesis reaction method A method will be described.

  The first liquid may be a liquid containing the first substance, may be the first substance itself, or may contain a substance other than the first substance. The first substance contained in the first liquid may be a single substance or a plurality of substances. The second liquid may be a liquid containing the second substance, may be the second substance itself, or may contain a substance other than the second substance. The second substance contained in the second liquid may be a single substance or a plurality of substances. “Immiscible with each other” means that when two liquids are mixed and allowed to stand for a certain time or longer, both liquids are separated into two layers. The first and second liquids that are immiscible with each other may be, for example, a hydrophilic liquid and a lipophilic liquid, or may be lipophilic liquids that are immiscible with each other. In addition, when both the first and second liquids are lipophilic liquids, the solubility parameters (SP values) of the first and second liquids are values that are separated so that they are not miscible. Also good. Further, as will be described later, when an emulsion is generated in the reaction step, the first and second liquids may be any liquid as long as they can constitute an emulsion, for example, Independently, it may or may not have a low viscosity (high fluidity). Here, the hydrophilic liquid is a liquid having a hydrophilic property that is soluble in water, and the lipophilic liquid is a liquid having a lipophilic property that is soluble in oils. When an organic compound is produced by the above synthetic reaction method, that is, when the synthetic reaction method is an organic compound production method, at least one of the first and second substances may be an organic compound. Good. Hereinafter, the case where the synthetic reaction method is a method for producing an organic compound will be described.

  Here, the case where the first liquid is a hydrophilic liquid and the second liquid is a lipophilic liquid will be mainly described. For example, when an ester is produced according to the present invention, that is, when the present invention is an ester production method using an organic compound production method, the first substance is an organic compound having a hydroxyl group, The substance may be an acid or an ester. The organic compound having a hydroxyl group may be an organic compound having an alcoholic hydroxyl group or an organic compound having a hydroxyl group that is not alcoholic. When the ester is produced by transesterification, the first substance may be an organic compound having an alcoholic hydroxyl group, and the second substance may be an ester. When the ester is produced by an esterification reaction, the first substance may be an organic compound having an alcoholic hydroxyl group, and the second substance may be an acid.

  Although the organic compound which has alcoholic hydroxyl group is not specifically limited, For example, sugar or alcohol may be sufficient. The sugar is not particularly limited, and may be, for example, a monosaccharide, disaccharide, trisaccharide, oligosaccharide, polysaccharide, or sugar alcohol. Examples of monosaccharides include triose, tetrose, pentose, hexose, heptose, octose, nonose, and decose. The disaccharide may be a monosaccharide homodisaccharide or a heterodisaccharide. Examples of the disaccharide include sucrose, sucrose, lactose, maltose, trehalose, tulanose, and cellobiose. Examples of the trisaccharide include raffinose, melezitose, and maltotriose. Examples of the oligosaccharide include fructooligosaccharide, galactooligosaccharide, and mannan oligosaccharide. Examples of the polysaccharide include glycogen, starch, cellulose, and fructan. Examples of the sugar alcohol include tetritol (eg, erythritol), pentitol (eg, pentaerythritol, arabitol, ribitol, xylitol, etc.), hexitol (eg, sorbitol, galactitol, mannitol, etc.), heptitol, octitol, nonitol, Examples include dexitol, sorbitan, and dodecitol. The alcohol may be, for example, a hydrophilic alcohol. Examples of the hydrophilic alcohol include methanol, ethanol, 1-propanol, 2-propanol, 2-methyl-1-propanol, 2-butanol, 2-methyl-2-propanol, glycerin, polyglycerin, ethylene glycol, and diethylene glycol. Or polyethylene glycol. Examples of the organic compound having a hydroxyl group that is not alcoholic include acids such as phenol.

  The ester that is the second substance used in the transesterification reaction is not particularly limited, but may be a fatty acid ester or an ester of an acid other than a fatty acid. Although fatty acid ester is not specifically limited, For example, fatty acid alkyl ester or glycerol fatty acid ester etc. may be sufficient. The fatty acid is not particularly limited, and may be, for example, a short chain fatty acid having 7 or less carbon atoms, a medium chain fatty acid having 8 to 10 carbon atoms, or a long chain fatty acid having 12 or more carbon atoms. The fatty acid may be a saturated fatty acid or an unsaturated fatty acid. Further, the unsaturated fatty acid may be a monounsaturated fatty acid (monoene fatty acid) or a polyunsaturated fatty acid (polyene fatty acid). Examples of fatty acids include lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, arachidic acid, arachidonic acid, behenic acid, lignoceric acid, nervonic acid, or erucic acid. Can be mentioned. Examples of esters of acids other than fatty acids include methyl salicylate, acetylsalicylic acid, phenyl acetate, and phthalate.

  The acid that is the second substance used for the esterification reaction is not particularly limited, but may be a fatty acid or an acid other than a fatty acid. The fatty acid may be, for example, those described above. Examples of acids other than fatty acids include phosphoric acid, sulfuric acid, sulfonic acid, and acids containing aromatics. Although the acid containing an aromatic is not specifically limited, For example, aromatic carboxylic acid or phenols may be sufficient. Examples of the aromatic carboxylic acid include benzoic acid, salicylic acid, phthalic acid, and terephthalic acid. Examples of phenols include phenol, cresol, dibutylhydroxytoluene, bisphenol A, eugenol, and gallic acid.

  In the mixing step, the first liquid and the second liquid may be simply added together, or premixing before the reaction step may be performed. In the former case, since the first and second liquids are immiscible with each other, both liquids may remain separated in the mixed liquid. When premixing is performed, for example, the first liquid and the second liquid may be stirred by a stirring means so as to be mixed more uniformly. The stirring may be, for example, stirring using a stirring means for rotating a blade-shaped member or a rod-shaped member, a magnetic stirrer, or the like, or bubbling stirring.

  As will be described later, when an emulsion is produced in the reaction step, the emulsifier for promoting the production of the first and second liquid emulsions in the mixing step or the reaction step is used as the first and second emulsifiers. It may or may not be added to the liquid. The emulsifier is not particularly limited, and examples thereof include glycerin fatty acid esters or sucrose fatty acid esters as fatty acid ester-based ones, and polyoxyethylene fatty acid alcohols as fatty acid alcohol-based ones. Fatty acid salt-based compounds can include fatty acid potassium or sodium salt, ammonium-based compounds can include alkylammonium salts, and sulfuric acid, sulfonic acid-based compounds can include alkyl sulfates. Etc. Moreover, when the ester produced | generated by a reaction step is an emulsifier, you may use the ester which is the emulsifier as an emulsifier for accelerating | stimulating the production | generation of the 1st and 2nd liquid emulsion. By doing so, it is possible to promote the formation of an ester which is the same emulsifier, and it is possible to avoid the added emulsifier from becoming an impurity. For example, when a sugar fatty acid ester is produced in the reaction step, the sugar fatty acid ester may be added as an emulsifier in the mixing step or the reaction step.

  In the reaction step, the first and second liquids are irradiated with microwaves and ultrasonic waves. In addition, the emulsion of both liquids may be produced | generated by the irradiation of the microwave and an ultrasonic wave, or it may not be so. In the present embodiment, the former case will be mainly described. Generating an emulsion may be to make an emulsion that is not in an emulsion state, or to maintain an emulsion state. An emulsion is a dispersion system of first and second liquids that are immiscible with each other. When one of the first and second liquids is a hydrophilic liquid and the other is a lipophilic liquid, the emulsion may be, for example, an oil-in-water emulsion or a water-in-oil type. It may be an emulsion. When both the first and second liquids are lipophilic liquids, the emulsion may be, for example, an oil-in-oil emulsion.

  Microwaves are irradiated to promote the reaction of the first and second substances contained in both liquids by heating the first and second liquids. Therefore, the output (power) of the microwave to be irradiated may be controlled according to the temperature of the liquid. By the control, the temperature of the liquid may be maintained at a predetermined temperature or a predetermined temperature range. The liquid whose temperature is to be measured may be, for example, a mixed liquid of the first and second liquids before the reaction, and a mixed liquid of the mixed liquid of the first and second liquids and the product after the reaction. It may be. The frequency of the microwave is not particularly limited. For example, it may be 2.45 GHz, 5.8 GHz, 24 GHz, 915 MHz, or other 300 MHz to 300 GHz. The frequency may be within the range. Moreover, the microwave of one frequency may be irradiated and the microwave of two or more frequencies may be irradiated. In the latter case, for example, microwaves of two or more frequencies may be irradiated at the same time, or may be irradiated at different times. When microwaves having two or more frequencies are irradiated at different times, for example, microwaves having a frequency that is easily absorbed by the raw material are irradiated at the start of the reaction, and the product is generated when the reaction proceeds. A microwave having a frequency that is easily absorbed by the light may be irradiated. Further, for example, microwaves having two or more frequencies may be irradiated at the same position or may be irradiated at different positions. When microwaves of two or more frequencies are respectively irradiated at different positions, for example, they are easily absorbed by the raw material at a position upstream of the flow reactor, that is, at a position where the ratio of the raw material is higher than that of the product. A microwave having a frequency may be irradiated, and a microwave having a frequency that is easily absorbed by the product may be irradiated at a position downstream of the reactor, that is, at a position where the ratio of the product is higher than that of the raw material.

  Ultrasound is irradiated to mix the first and second liquids. An emulsion may be generated by the mixing. That is, ultrasonic waves may be irradiated to produce an emulsion by dispersing one of the first and second liquids as a dispersoid in a dispersion medium that is the other liquid. Therefore, at least one of the output (power) and frequency of the irradiated ultrasonic waves may be controlled so that the first and second liquids are appropriately mixed, or an emulsion of both liquids is generated. . For example, the ultrasonic power of the power in the first and second liquids is irradiated, and control is performed to gradually increase the ultrasonic power until both liquids are properly mixed or an emulsion is formed. Also good. Depending on the types and amounts of the first and second liquids, the output and frequency of ultrasonic waves suitable for mixing both liquids, or the output of ultrasonic waves necessary for generating an emulsion, The frequency will be determined. Therefore, you may make it irradiate the liquid mixture of the 1st and 2nd liquid with the ultrasonic wave of the power and frequency according to the kind and quantity of the 1st and 2nd liquid. The frequency of the ultrasonic waves is not particularly limited, but may be, for example, 20 kHz, 25 kHz, 40 kHz, or other frequencies within the range of 15 kHz to 10 GHz. Further, ultrasonic waves with one frequency may be irradiated, and ultrasonic waves with two or more frequencies may be irradiated. In the latter case, for example, ultrasonic waves having two or more frequencies may be irradiated at the same time, or may be irradiated at different times. Further, for example, ultrasonic waves having two or more frequencies may be irradiated at the same position or may be irradiated at different positions. As a method of irradiating ultrasonic waves, for example, an ultrasonic vibrator is disposed inside a container (reactor) containing first and second liquids, and the ultrasonic vibrator is changed to the first and second liquids. You may make it irradiate with an ultrasonic wave directly, or it arrange | positions an ultrasonic transducer | vibrator in contact with the container which accommodates the 1st and 2nd liquid, and superposes the 1st and 2nd liquid through the container. You may make it irradiate a sound wave.

  The microwave and the ultrasonic wave may be irradiated at the same time, or may be irradiated at different times. In the latter case, in order to obtain the effect of microwave irradiation and the effect of ultrasonic irradiation simultaneously, for example, microwave irradiation and ultrasonic irradiation are alternately performed in a short period of time. You may make it switch. In addition, it is preferable that at least microwaves are applied to the first and second liquids mixed by ultrasonic waves or the emulsion generated by ultrasonic waves. This is to promote the reaction of substances contained in both liquids, for example, the reaction of substances contained in the dispersion medium and dispersoid of the emulsion. In addition, for example, microwaves and ultrasonic waves are irradiated for the production of an emulsion, but may also be irradiated for the maintenance of the emulsion. That is, in order to maintain the emulsion continuously, microwaves and ultrasonic waves may be irradiated.

  In the reaction step, the first and second substances contained in the first and second liquids react. In addition, when an emulsion is produced, it is included in the first and second liquids (which liquid may be a dispersoid) that are the dispersion medium and the dispersoid of the produced emulsion in the reaction step, respectively. The first and second substances to be reacted will react. The first and second substances may be contained in the first and second liquids, for example, before the emulsion is generated or after the emulsion is generated. May be. In the latter case, for example, an emulsion of the first liquid not containing the first substance and the second liquid is generated, and then the first substance is added and dissolved in the first liquid. The first substance contained in the first liquid may react with the second substance contained in the second liquid, the second liquid not containing the second substance, and the first An emulsion with the liquid is generated, after which the second substance is added and dissolved in the second liquid, whereby the first substance contained in the first liquid and the second substance contained in the second liquid The substance may react. In addition, when a substance is added to a liquid after an emulsion is produced | generated, it is suitable for the substance to be added to the liquid which is a dispersion medium, but it may not be so. Further, during the reaction, a third substance other than the first and second substances may be involved in the reaction. For example, the third substance may be insoluble in either the first or second liquid. In addition, the third substance may or may not be a catalyst, for example. The reaction of the first and second substances in the reaction step can be of various known types, the first and second substances, their usage, temperature, time, pressure, pH, solvent, catalyst. The reaction conditions such as separation of the target product from the reaction mixture, collection, production and the like may be known. The reaction is not particularly limited, and may be, for example, a substitution reaction, an addition reaction, an elimination reaction, or a rearrangement reaction, or a combination of two or more of these reactions.

A substitution reaction is a type of reaction in which an atom or atomic group in a molecule is replaced with another atom or atomic group. The substitution reaction is not particularly limited, and may be, for example, an amidation reaction, a halogenation reaction, an amine substitution reaction, an esterification reaction, an ester exchange reaction, an ion exchange reaction, or the like.
The amidation reaction is not particularly limited, and may be, for example, the following reaction.
RCOOR ¹ + NR ² R ³ R ⁴ → RCONR ³ R ⁴ + R ¹ OR ²
In the formula, R, R ¹ , R ² , R ³ , and R ⁴ are not particularly limited. For example, each independently has a hydrogen atom, or an alkyl group or substituent that may have a substituent. It may be an aryl group or the like. When the reaction is an amidation reaction, for example, the first substance may be NR ² R ³ R ⁴ and the second substance may be RCOOR ¹ or vice versa.

Further, the halogenation reaction is not particularly limited, but may be, for example, the following reaction.
R ⁵ OH + HX → R ⁵ X + H ₂ O
In the formula, R ⁵ is not particularly limited, and may be, for example, an alkyl group which may have a substituent or an aryl group which may have a substituent. X is a halogen atom, and may be, for example, a chlorine atom (Cl), a fluorine atom (F), a bromine atom (Br), or an iodine atom (I). When the reaction is a halogenation reaction, for example, the first substance may be HX and the second substance may be R ⁵ OH.

Moreover, the amine substitution reaction is not particularly limited, but may be, for example, the following reaction.
R ⁶ OH + NH ₃ → R ⁶ NH ₂ + H ₂ O
R ⁶ OH + R ⁷ OH + NH ₃ → R ⁶ R ⁷ NH + 2H ₂ O
R ⁶ OH + R ⁷ OH + R ⁸ OH + NH ₃ → R ⁶ R ⁷ R ⁸ N + 3H ₂ O
In the formula, R ⁶ , R ⁷ , and R ⁸ are not particularly limited. For example, they may be independently an alkyl group that may have a substituent or an aryl group that may have a substituent. Good. When the reaction is an amine substitution reaction, for example, the first substance may be NH ₃ and the second substance may be R ⁶ OH, R ⁷ OH, R ⁸ OH.

  When the reaction is an ester synthesis reaction, for example, an ink raw material or biodiesel fuel can be produced, or an ester such as a sucrose fatty acid ester used as a food emulsifier can be produced. When the reaction is an ester synthesis reaction, for example, the first substance is an organic compound having a hydroxyl group, the second substance is an acid or an ester, and in the reaction step, an organic compound having a hydroxyl group and an acid Alternatively, an ester may be synthesized with an ester to produce an ester. The ester synthesis reaction may be, for example, a transesterification reaction or an esterification reaction. When the reaction is a transesterification reaction, for example, the first substance is an organic compound having an alcoholic hydroxyl group, the second substance is an ester, and in the reaction step, an organic compound having an alcoholic hydroxyl group and An ester may be produced by an ester exchange reaction with an ester. When the ester is a fatty acid ester, the fatty acid ester may be produced by transesterifying the organic compound having an alcoholic hydroxyl group and the fatty acid ester in the reaction step. When the ester is a fatty acid ester and the organic compound having an alcoholic hydroxyl group is a sugar, the sugar fatty acid ester may be produced by transesterifying the sugar and the fatty acid ester in the reaction step. When the sugar is sucrose, in the reaction step, sucrose fatty acid ester may be produced by transesterification of sucrose and fatty acid ester. Although transesterification reaction is not specifically limited, For example, the following can be mentioned. The left side of the arrow is the first and second substances, and the right side of the arrow is the ester produced by the transesterification reaction and the alcohol as a byproduct. In this case, for example, a liquid containing sugar or alcohol may be a dispersion medium, and a liquid containing an ester may be a dispersoid, or it may not be.

Sugar + fatty acid ester → sugar fatty acid ester + alcohol Sucrose + fatty acid ester → sucrose fatty acid ester + alcohol Sucrose + palmitic acid ester → sucrose palmitic acid ester + alcohol Sucrose + stearic acid ester → sucrose stearic acid ester + alcohol Sucrose + myristic acid ester → Sucrose myristic acid ester + alcohol Sucrose + oleic acid ester → Sucrose oleic acid ester + alcohol Sucrose + lauric acid ester → Sucrose lauric acid ester + alcohol Sucrose + erucic acid ester → Sugar erucic acid ester + alcohol sorbitan + fatty acid ester → sorbitan fatty acid ester + alcohol glycerin + fatty acid ester → glycerin fatty acid ester + alcohol polyglycerin + fatty acid ester → poly Glycerin fatty acid ester + alcohol Methanol + triglyceride → fatty acid methyl ester + glycerin

  In each of the transesterification reactions, one or more hydroxyl groups of sugar or sucrose are substituted with fatty acid esters. Moreover, the position of the hydroxyl group in which the transesterification is performed is not ask | required. In the transesterification reaction between sucrose and a fatty acid ester, the fatty acid ester substituted with two or more hydroxyl groups of sucrose may be the same type of fatty acid ester or a different type of fatty acid ester. . In the latter case, for example, the fatty acid ester substituted with two hydroxyl groups of sucrose may be palmitic acid ester and stearic acid ester.

  When the reaction is an esterification reaction, for example, the first substance is an organic compound having an alcoholic hydroxyl group, the second substance is an acid, and an organic compound having an alcoholic hydroxyl group is used in the reaction step. An ester may be produced by esterifying a compound and an acid. When the acid is a fatty acid, the fatty acid ester may be produced by esterifying the organic compound having an alcoholic hydroxyl group and the fatty acid in the reaction step. When the acid is a fatty acid and the organic compound having an alcoholic hydroxyl group is a sugar, the sugar fatty acid ester may be produced by esterifying the sugar and the fatty acid in the reaction step. When the sugar is sucrose, the sucrose fatty acid ester may be produced by an esterification reaction between sucrose and a fatty acid in the reaction step. The esterification reaction is not particularly limited, and examples thereof include the following. The left side of the arrow is the first and second substances, and the right side of the arrow is the ester produced by the esterification reaction and water as a by-product. In this case, for example, a liquid containing sugar or alcohol may be a dispersion medium, and a liquid containing fatty acid may be a dispersoid, or it may not be.

Sugar + fatty acid → sugar fatty acid ester + water Sucrose + palmitic acid → sucrose palmitic acid ester + water Sucrose + palmitic acid → sucrose stearic acid ester + water Sucrose + myristic acid → sucrose myristic acid ester + water sucrose + Oleic acid → sucrose oleic acid ester + water sucrose + lauric acid → sucrose lauric acid ester + water sucrose + erucic acid → sucrose erucic acid ester + water sorbitan + fatty acid → sorbitan fatty acid ester + water glycerin + fatty acid → Glycerin fatty acid ester + water Polyglycerin + fatty acid → Polyglycerin fatty acid ester + water Methanol + Fatty acid → Fatty acid methyl ester + water

Moreover, although ion exchange reaction is not specifically limited, For example, the following can be mentioned. You may make the sodium cyanide which is the 1st substance contained in the water (water layer) which is the 1st liquid react with the alkyl chloride contained in the 2nd liquid (oil layer). In that case, the reaction proceeds by an ion exchange reaction with a quaternary ammonium salt as a catalyst, and alkyl cyanide is synthesized. The alkyl chloride is not particularly limited, and may be, for example, C ₈ H ₁₇ -Cl. Further, the quaternary ammonium salt that is a catalyst is not particularly limited, and may be, for example, (CH ₃ (CH ₂ ) ₁₅ ) Bu ₃ P ⁺ Br ⁻ or the like. In that case, Br ⁻ of the catalyst and CN ⁻ of sodium cyanide (NaCN) are ion-exchanged, CN is supplied to the oil layer, and is exchanged with Cl of alkyl chloride to produce alkyl cyanide. For example, when the alkyl chloride is C ₈ H ₁₇ -Cl, C ₈ H ₁₇ -CN is generated.

The addition reaction is a reaction in which two or more kinds of molecules are directly bonded, or a reaction in which another molecule is newly added to a specific part of a certain molecule. The addition reaction is not particularly limited, and may be, for example, an alkene halogenation reaction or a ring-opening polymerization reaction.
Although the halogenation reaction of alkene is not specifically limited, For example, the following reaction may be sufficient.
C _n H _2n + HX → C _n H _{2n + 1} X
C _n H _2n + X ₂ → C _n H _2n X ₂
In the formula, X is a halogen atom, and may be, for example, a chlorine atom (Cl), a fluorine atom (F), a bromine atom (Br), or an iodine atom (I). N is an integer of 2 or more. When the reaction is halogenation reaction of alkene, for example, the first substance is HX or X _2, the second material may be a alkene.

  The cyclic compound used in the ring-opening polymerization reaction is not particularly limited, and may be, for example, a cyclic carbonyl compound such as lactone or lactam, an oxirane compound such as epoxide, or a cyclic olefin. More specifically, the ring-opening polymerization reaction may be a ring-opening polymerization reaction of ε-caprolactone in which ε-caprolactone is reacted with an alcohol or an amine. When the reaction is a ring-opening polymerization reaction, for example, the first substance may be an alcohol or an amine, and the second substance may be a cyclic compound.

An elimination reaction is a reaction in which atoms or atomic groups are removed from a molecule by breaking bonds. The elimination reaction is not particularly limited, and may be, for example, an alcohol dehydration reaction or a reaction for obtaining a hydrogen halide and an alkene from an alkyl halide.
The rearrangement reaction is a reaction in which the arrangement of atoms in the molecule changes.
When the reaction is an elimination reaction or a rearrangement reaction, for example, the first substance may be a raw material for those reactions, and the second substance may be a catalyst used in the reaction, or The reverse is also possible.

  Further, the reaction in the reaction step may be an emulsion polymerization reaction or may not be an emulsion polymerization reaction. When the reaction in the reaction step is an emulsion polymerization reaction, the liquid that is a dispersoid (herein referred to as the second liquid) is a liquid that includes a monomer that is the second substance. The monomer may be one type or two or more types. Further, an emulsifier having the dispersoid as an emulsion may be added in the mixing step, or the emulsion may be generated only by ultrasonic irradiation without adding an emulsifier. In the case of an emulsion polymerization reaction, the first substance contained in the liquid (here, the first liquid) that is a dispersion medium is a polymerization initiator that initiates polymerization of the monomer. The polymerization initiator, which is the first substance, may be added to the dispersion medium after the emulsion is generated, or may be added to the dispersion medium before the emulsion is generated. When the emulsion polymerization reaction is performed, in the reaction step, polymerization of the monomer contained in the dispersoid is started by the polymerization initiator contained in the dispersion medium, and polymer particles grow. When the monomer is not supplied from the dispersion medium, the polymerization is stopped.

  The monomer in the emulsion polymerization is not particularly limited, and may be, for example, styrene, methacrylic acid ester, or acrylic acid ester. The polymerization initiator is not particularly limited, but may be, for example, an azoamide type. As the azoamide polymerization initiator, for example, 2,2′-azobis [2- (2-imidazolin-2-yl) propane] · dihydrochloride (2,2′-Azobis [2- (2-imidazolin) -2-yl) propane] Dihydrochloride), or 2,2′-azobis [N- (2-carboxyethyl) -2-methylpropaneamidine] (2,2′-Azobis [N- (2-carboxyethyl) -2 -methylpropionamidine]) and the like. The polymerization initiator may be added to water as a dispersion medium. That is, the first liquid may be water having a polymerization initiator.

  Further, the above-described reaction may be performed, for example, in a batch-type (batch-type) reactor or in a flow-type (continuous) reactor. Hereinafter, an example of a flow type reactor will be described.

  FIG. 1 is a diagram illustrating an example of a configuration of a chemical reaction apparatus 1 in which the above reaction is performed. The chemical reaction apparatus 1 includes a mixing unit 12, a reactor 13, a microwave generator 14, a waveguide 15, a microwave control unit 16, an ultrasonic vibrator 17, an ultrasonic oscillator 18, and an ultrasonic wave. The control part 19 and the process liquid storage tank 20 are provided.

  In the mixing unit 12, the first and second liquids are premixed before being charged into the reactor 13. Each of the first and second liquids may or may not contain a plurality of substances independently. For example, the mixing unit 12 may mix the first and second liquids by rotating a blade-shaped member, a wing-shaped member, or a screw-shaped member. Further, the catalyst may be mixed in the mixing unit 12 together with the first and second liquids. The catalyst may be a solid catalyst (heterogeneous catalyst) or a liquid catalyst (homogeneous catalyst). The solid catalyst, for example, may or may not have microwave absorption or microwave sensitivity. When the solid catalyst has microwave absorptivity or microwave sensitivity, the solid catalyst is heated by the microwave when the microwave is irradiated inside the reactor 13 described later, and in the vicinity of the solid catalyst. The chemical reaction will be promoted. For example, when 2.45 GHz microwaves are irradiated, carbons other than fullerene (eg, graphite, carbon nanotubes, activated carbon, etc.), iron, nickel, cobalt, Or there is ferrite. In addition, preheating may or may not be performed in the mixing unit 12. The first and second liquids mixed in the mixing unit 12 are input to the upstream side of the reactor 13.

  The reactor 13 is a horizontal flow type reactor in which the contents flow in the horizontal direction with an unfilled space above. The contents are a mixture of the first and second liquids. In addition, since a product is produced | generated from the substance contained in the 1st and 2nd liquid by the chemical reaction in the reactor 13, you may consider that the product is contained in the content of the reactor 13. FIG. That is, the contents can be said to be the first and second liquids and / or products. The contents are usually liquid. The inner wall of the reactor 13 is preferably made of a material that reflects microwaves. An example of a substance that reflects microwaves is metal. The internal configuration of the reactor 13 will be described later.

  The microwave generator 14 generates a microwave. The chemical reaction apparatus 1 may include one microwave generator 14 or may include two or more microwave generators 14. The frequency of the microwave is not particularly limited, and may be, for example, 2.45 GHz, 5.8 GHz, 24 GHz, 913 MHz, or other frequencies in the range of 300 MHz to 300 GHz.

  The waveguide 15 transmits the microwave generated by the microwave generator 14 to the unfilled space of the reactor 13. As shown in FIG. 1, there are usually as many waveguides 15 as the number of microwave generators 14. In addition, it is preferable to use the waveguide 15 having a standard corresponding to the frequency of the microwave generated by the microwave generator 14.

  The microwave control unit 16 controls the output of the microwave irradiated to the reactor 13 according to the temperature measured by the temperature measurement unit 25 described later. By the control by the microwave control unit 16, the inside of the reactor 13 can be maintained at a desired temperature or a desired temperature range.

The ultrasonic transducer 17 generates ultrasonic waves. The ultrasonic transducer 17 is disposed inside the reactor 13 and is connected to the ultrasonic oscillator 18 via a flange or the like. Note that it is preferable that microwaves do not leak in the connection. The ultrasonic vibrator 17 applies ultrasonic vibrations to the contents of the reactor 13 according to the high frequency output received from the ultrasonic oscillator 18. It is preferable that the first and second liquids are mixed with each other according to the ultrasonic vibration. For example, the first and second liquid emulsions may be generated by the ultrasonic vibration.
The ultrasonic oscillator 18 generates a high frequency output and supplies it to the ultrasonic transducer 17. The ultrasonic oscillator 18 is controlled by the ultrasonic control unit 19.

  The ultrasonic control unit 19 controls the high frequency output of the ultrasonic oscillator 18. The control may be, for example, control of output (power) magnitude or on / off control. For example, the ultrasonic control unit 19 uses ultrasonic waves so that the magnitude of the high-frequency output according to the first and second liquids and the on / off pattern of the high-frequency output according to the first and second liquids are obtained. The oscillator 18 may be controlled.

  When the contents of the reactor 13 include a catalyst, a catalyst separation unit (not shown) for separating the catalyst from the product after the reaction in the reactor 13 between the reactor 13 and the treatment liquid storage tank 20. ) May or may not be present. In the catalyst separation unit, for example, the solid catalyst may be separated by a filter or precipitation. When the solid catalyst contains a magnetic material, the solid catalyst may be separated by adsorbing the solid catalyst with a magnet. The separated solid catalyst can be reused as appropriate. When a liquid catalyst is used, the catalyst may be separated by distillation, extraction, or neutralization in the catalyst separation unit.

  A product discharged from the reactor 13 is placed in the processing liquid storage tank 20. And it will be divided into final products and by-products as appropriate. For example, when the raw material is free fatty acid and esterification is performed in the reactor 13, a product that is biodiesel fuel and a by-product that is water are obtained, and both are separated in the treatment liquid storage tank 20. . In that case, an acid catalyst is used. For example, when the raw material is triglyceride and transesterification is performed in the reactor 13, a product that is biodiesel fuel and a by-product that is glycerin are obtained, and both are separated in the treatment liquid storage tank 20. It is done. In that case, an alkali catalyst is used. For example, when the raw material is sucrose and an ester synthesis reaction with a fatty acid ester or an esterification reaction with a fatty acid is performed in the reactor 13, a product that is a sucrose fatty acid ester, alcohol, water, etc. By-products are obtained, and both are separated in the treatment liquid storage tank 20.

  It should be noted that a cooler (not shown) for cooling the substance after the reaction in the reactor 13 may be provided in the subsequent stage of the reactor 13 or not. In the former case, for example, the cooler may cool the substance after the reaction in the reactor 13 with water.

  FIG. 2 is a diagram illustrating an example of the internal structure of the reactor 13 according to the present embodiment. In FIG. 2, the reactor 13 has a plurality of chambers 31, 32, and 33 that are continuous in series. Each of the chambers 31 to 33 is partitioned by a plurality of partition plates 21 that partition the inside of the reactor 13. As described above, the unfilled space 22 exists above the reactor 13. The unfilled space 22 is irradiated with the microwave generated by the microwave generator 14 through the waveguide 15. The partition plate 21 may be microwave transmissive, microwave absorptive, or may reflect microwaves. Examples of the material that transmits microwaves include Teflon (registered trademark), quartz glass, ceramic, and silicon nitride alumina. Moreover, the partition plate 21 may be comprised by the combination of arbitrary 2 or more materials among a microwave transparent material, a microwave absorptive material, and a microwave reflective material.

  The contents 30 that are the first and second liquids that have entered the reactor 13 flow between the chambers 31 to 33 and are finally output from the downstream (the right end of the reactor 13 in FIG. 2). The partition plate 21 has a flow path through which the contents flow. The flow path is a flow path in which the contents mainly flow from the upstream side (left side in FIG. 2) to the downstream side (right side in FIG. 2) of the reactor 13, but the short arrows shown in FIG. Thus, a part may flow from the downstream side to the upstream side. The flow path of the partition plate 21 may be, for example, a flow path in which the content overflows above the partition plate 21, or may be a flow path in which the content flows in a gap between the partition plates 21. As such a partition plate 21, for example, various partition plates 21 described in International Publication No. WO2013 / 001629 may be used. The reactor 13 may or may not have a slope that decreases from the upstream side toward the downstream side.

  It should be noted that a stirring means for stirring the contents 30 may or may not exist inside the reactor 13. If stirring means are present, the stirring means may or may not be present for each chamber 31-33.

  In addition, as shown in FIG. 2, the reactor 13 may also include a temperature measurement unit 25. The temperature inside the reactor 13 is preferably the temperature of the content 30 of the reactor 13. Although FIG. 2 shows a case where the temperature measuring unit 25 is present in each of the chambers 31 to 33, this need not be the case. For example, the temperature measurement unit 25 may measure temperature using a thermocouple, measure temperature using an infrared sensor, measure temperature using an optical fiber, or measure temperature using other methods. Good. The temperature measured by the temperature measuring unit 25 is passed to the microwave control unit 16 and used for controlling the microwave output by the microwave generator 14. The control is for maintaining the temperature of each of the chambers 31 to 33 at a desired temperature or a desired temperature range as described above.

  Further, the ultrasonic oscillator 18 outputs a high frequency output to the ultrasonic transducer 17 according to the control by the ultrasonic control unit 19, and the ultrasonic transducer 17 generates an ultrasonic wave according to the high frequency output. As a result, in each of the chambers 31 to 33, the contents 30 are irradiated with ultrasonic waves, and the first and second liquids are mixed. In addition, the emulsion of the 1st and 2nd liquid may be produced | generated or maintained by the irradiation. By performing such mixing, the contact area between the first and second liquids is increased, and as a result, the reaction between the first and second substances is promoted. This is believed to be particularly noticeable when an emulsion is produced or maintained. Therefore, compared with the case where two liquids that are not miscible with each other are simply stirred and reacted with a stirring blade or the like, if the reaction time is the same, the yield is higher than when no ultrasonic wave is irradiated. When the yield is the same, the reaction time is shorter than when no ultrasonic wave is irradiated.

  The shape of the reactor 13 does not matter. For example, the reactor 13 may have a cylindrical shape in which the left-right direction in FIG. 2 is the length direction, may have a rectangular parallelepiped shape, or may have another shape. The wall surface of the reactor 13 may be covered with a heat insulating material. By doing so, it is possible to prevent the heat inside the reactor 13 from being released to the outside.

  Next, the operation of the chemical reaction apparatus 1 will be briefly described. The first and second liquids are supplied to the mixing unit 12 by the pump 11. And it mixes in the mixing part 12, and is thrown into the reactor 13. FIG. The supply speed of the raw material or the like to the reactor 13 may be determined in advance.

  The raw material supplied to the reactor 13 flows from the upstream side to the downstream side. At that time, the microwave generated by the microwave generator 14 is transmitted to the unfilled space 22 of the reactor 13 through the waveguide 15 and irradiated to the contents 30. As a result, the content 30 is heated, and the reaction is promoted. In addition, the temperature of each chamber 31-33 is measured by the temperature measurement part 25, and is passed to the microwave control part 16 by the path | route which is not shown in figure. And the microwave control part 16 controls the output of the microwave generator 14 so that the temperature of each chamber 31-33 may become desired temperature or a desired temperature range. Further, the ultrasonic wave generated by the ultrasonic transducer 17 is irradiated to the contents 30. As a result, the first and second liquids are mixed, and the reaction of the substances contained in the first and second liquids is promoted. The reaction is the aforementioned synthesis reaction, and may be, for example, an ester synthesis reaction or an ion exchange reaction. In addition, the emulsion of the 1st and 2nd liquid may be produced | generated or maintained by irradiation of a microwave and an ultrasonic wave.

  The product output from the reactor 13 is charged into the processing liquid storage tank 20, and is divided into a target product and a by-product in the processing liquid storage tank 20. In this way, the final product is obtained. By repeatedly executing such processing, target products are sequentially generated.

Moreover, although the case where the ultrasonic transducer | vibrator 17 exists in each chamber 31-33 of the reactor 13 was demonstrated, it may not be so. For example, in the case of the first and second liquids in which the emulsion is maintained for a long time even after the irradiation of ultrasonic waves is finished, the ultrasonic vibrator 17 is disposed only in the chamber 31, and the emulsion is stored in the chamber 31. You may make it produce | generate.
Moreover, although the reactor 13 which has the three chambers 31-33 continued in series was demonstrated, the number of these chambers is not ask | required. The number of chambers may be one, two, or four or more.

  Moreover, although the chemical reaction apparatus 1 provided with the temperature measurement part 25 and the microwave control part 16 was demonstrated, the chemical reaction apparatus 1 does not need to be provided with the temperature measurement part 25 and the microwave control part 16. FIG. For example, when the temperature of the reactor 13 can be maintained at a desired temperature or temperature range by setting the microwave output to a predetermined value, the microwave output control using the temperature is performed. It is not necessary to perform.

Moreover, although the case where the 1st and 2nd liquid was mixed and thrown into the reactor 13 was demonstrated, it may not be so. For example, the first and second liquids may be charged into the reactor 13 without being premixed. In such a case, the chemical reaction device 1 may not include the mixing unit 12.
Moreover, although the case where the chemical reaction apparatus 1 was provided with the process liquid storage tank 20 was demonstrated, it may not be so. For example, with respect to a mixture of products and by-products output from the chemical reaction device 1, the product may be extracted in another device.

  In the above description, the case where the reaction is performed in the horizontal flow type reactor 13 having the unfilled space 22 inside is described. However, the reaction is performed in the flow type reactor 13 having no unfilled space inside. May be. In that case, microwaves are directly irradiated to the contents 30. The flow reactor 13 having no unfilled space inside may be, for example, a vertical reactor. In the vertical reactor, the content flows from below to above or from above to below.

In the above description, the case where the ultrasonic transducer 17 is disposed inside the reactor 13 has been described. However, the ultrasonic transducer 17 is disposed outside the reactor 13, and the reactor 13 itself is disposed by the ultrasonic transducer 17. The contents 30 may be irradiated with ultrasonic waves by vibrating the.
In the above description, the case where the reaction is performed in the flow type reactor 13 has been described. However, the reaction may be performed in a batch type reactor.

  Moreover, although the above-mentioned description demonstrated the case where the manufacturing method of an organic compound and the manufacturing method of ester using the manufacturing method of the organic compound provided with a mixing step, it may not be so. You may make it make the 1st and 2nd substance contained in both liquids react by irradiating a microwave and an ultrasonic wave with respect to the 1st and 2nd liquid, without performing premixing.

  In the above description, at least one of the first and second liquids to be irradiated with the microwave and the ultrasonic wave is a liquid that is heated when heated. There may be. Specifically, the first solid obtained by solidifying the first liquid and the second liquid are mixed, and the first solid contained in the mixture is irradiated by preheating or irradiation with microwaves or ultrasonic waves. May be melted into the first liquid. Even in that case, as a result, the first and second liquids which are immiscible with each other are irradiated with microwaves and ultrasonic waves, and the reaction of the first and second substances contained in both liquids is promoted. can do.

  As described above, according to the method for producing an organic compound according to the present invention and the method for producing an ester using the method for producing an organic compound, when reacting substances contained in two liquids that are immiscible with each other, Since the liquid emulsion is produced and reacted, the area of the interface between the two liquids is increased, and as a result, the reaction is promoted. As a result, higher yields and shorter time reactions can be realized. When the reaction is ester synthesis, for example, the ester can be produced with higher yield. Even if the emulsion is not generated by irradiating the first and second liquids with microwaves and ultrasonic waves, both are mixed by the irradiation, and the area of the interface between the two liquids increases. The reaction will be promoted.

EXAMPLES Next, although this invention is demonstrated concretely based on an Example, this invention is not limited only to these Examples.
Example 1 Production of Sucrose Fatty Acid Ester In a three-necked flask, 34 g of sucrose, 2 g of sucrose fatty acid ester as an emulsifier, and 50 g of water were added and completely dissolved by heating and stirring at 60 ° C. for 30 minutes. Further, 27 g of methyl palmitate was heated and melted at 60 ° C. and charged into a three-necked flask. The three-necked flask was placed in a microwave reactor equipped with a stirrer and a thermometer (thermocouple), and then an ultrasonic horn was introduced from the top of the three-necked flask. Then, microwaves and ultrasonic waves were simultaneously irradiated while stirring, and a transesterification reaction was performed for 10 hours while maintaining the temperature at 90 ° C. ± 2 ° C. The liquid during the transesterification reaction was an oil-in-water emulsion. After completion of the reaction, the mixture was diluted with 100 ml of ethanol, the water-ethanol phase was dried under reduced pressure to obtain a solid, 100 ml of methyl ethyl ketone was added, the solid was filtered, and then the methyl ethyl ketone was removed from the filtrate with an evaporator. 26.6 g of a solid containing 82.9% by weight of sucrose palmitate was obtained. The yield was 33.0%.

Comparative Example 1 Microwave irradiation only A three-necked flask was charged with 34 g of sucrose, 2 g of sucrose fatty acid ester as an emulsifier, and 50 g of water, and completely dissolved by heating and stirring at 60 ° C. for 30 minutes. Further, 27 g of methyl palmitate was heated and melted at 60 ° C. and charged into a three-necked flask. The three-necked flask was placed in a microwave reactor equipped with a stirrer and a thermometer (thermocouple), and then microwaved while stirring and transesterified for 10 hours while maintaining the temperature at 90 ° C ± 2 ° C. Reaction was performed. In Comparative Example 1, no ultrasonic irradiation was performed. Further, the liquid during the transesterification reaction was a two-layer liquid. After completion of the reaction, the mixture was diluted with 100 ml of ethanol, the water-ethanol phase was dried under reduced pressure to obtain a solid, 100 ml of methyl ethyl ketone was added, the solid was filtered, and then the methyl ethyl ketone was removed from the filtrate with an evaporator. 14.7 g of a solid containing 59.0% by weight of sucrose palmitate was obtained. The yield was 11.0%.

Comparative Example 2 Normal heating only 34 g of sucrose, 2 g of sucrose fatty acid ester as an emulsifier, and 50 g of water were placed in a three-necked flask and completely dissolved by heating and stirring at 60 ° C. for 30 minutes. Further, 27 g of methyl palmitate was heated and melted at 60 ° C. and charged into a three-necked flask. The three-necked flask was placed in an oil bath, and a transesterification reaction was performed for 10 hours while maintaining the temperature measured with a thermometer (thermocouple) at 90 ° C. ± 2 ° C. while stirring. In Comparative Example 2, microwave irradiation and ultrasonic irradiation were not performed. Further, the liquid during the transesterification reaction was a two-layer liquid. After completion of the reaction, the mixture was diluted with 100 ml of ethanol, the water-ethanol phase was dried under reduced pressure to obtain a solid, 100 ml of methyl ethyl ketone was added, the solid was filtered, and then the methyl ethyl ketone was removed from the filtrate with an evaporator. 10.2 g of a solid containing 35.5% by weight of sucrose palmitate was obtained. The yield was 2.7%.

  In addition, the liquid state at the time of the transesterification reaction in Examples 1 and Comparative Examples 1 and 2 was determined in a state in which irradiation with microwaves and ultrasonic waves and stirring were stopped. Moreover, as the microwave reactor of Example 1 and Comparative Example 1, μ-Reactor (manufactured by Shikoku Keiki Kogyo Co., Ltd.) was used. The transesterification in Examples 1 and Comparative Examples 1 and 2 was performed at normal pressure. Further, UH-600S (manufactured by SMT Co., Ltd.) was used as the ultrasonic horn, and the ultrasonic frequency was 20 kHz. In Examples 1 and Comparative Examples 1 and 2, the same commercially available sucrose fatty acid ester was used as the emulsifier.

上記表、及び図３のグラフから、マイクロ波（ＭＷ）と超音波（ＵＳ）とを照射した場合（実施例１）の収率が、通常加熱（ＣＨ）のみの場合（比較例２）や、マイクロ波の照射のみの場合（比較例１）と比較して、顕著に高いことが分かる。実施例１の場合には、エマルションを生成することによって、ショ糖とエステル（パルミチン酸メチル）の接している界面の面積を増大させることができると共に、内部加熱を行うことができるマイクロ波を照射することによって、両物質が反応するために必要な活性化エネルギーを、両物質の界面に効率よく供給することができ、その結果として、比較例１，２と比較して、非常に高い収率を得ることができているのではないかと推定できる。 The yields of Examples 1 and Comparative Examples 1 and 2 are as shown in the following table and the graph of FIG.

From the above table and the graph of FIG. 3, when the microwave (MW) and the ultrasonic wave (US) are irradiated (Example 1), the yield is normal heating (CH) only (Comparative Example 2) It can be seen that it is significantly higher than the case of only microwave irradiation (Comparative Example 1). In the case of Example 1, by generating an emulsion, it is possible to increase the area of the interface where sucrose and ester (methyl palmitate) are in contact, and to irradiate microwaves that can be internally heated. As a result, the activation energy necessary for the reaction between the two substances can be efficiently supplied to the interface between the two substances. As a result, the yield is very high compared to Comparative Examples 1 and 2. Can be estimated.

  In this example, the case where the transesterification reaction is carried out has been described, but also in the esterification reaction, in other substitution reactions, addition reactions, elimination reactions, rearrangement reactions, or combinations of two or more thereof. Similarly, it is considered that the reaction is further promoted by generating an emulsion by irradiating microwaves and ultrasonic waves.

  In addition, this invention is not limited to the above Example, A various change is possible, and it cannot be overemphasized that they are also included in the scope of the present invention.

  The ester obtained by the organic compound production method of the present invention and the ester production method using the organic compound production method can be used as, for example, an ink raw material, biodiesel fuel, or an emulsifier for food. it can.

DESCRIPTION OF SYMBOLS 1 Chemical reaction apparatus 12 Mixing part 13 Reactor 14 Microwave generator 15 Waveguide 16 Microwave control part 17 Ultrasonic vibrator 18 Ultrasonic oscillator 19 Ultrasonic control part

Claims (15)

By irradiating the first liquid and the second liquid, which are immiscible liquids, with microwaves and ultrasonic waves, the first substance contained in the first liquid and the second liquid are contained in the second liquid. The manufacturing method of the organic compound made to react with the 2nd substance. The production of an organic compound according to claim 1, wherein the first and second liquid emulsions are formed by irradiation with microwaves and ultrasonic waves, and the first substance and the second substance are reacted. Method. The first liquid is a hydrophilic liquid;
The method for producing an organic compound according to claim 1, wherein the second liquid is a lipophilic liquid. The method for producing an organic compound according to any one of claims 1 to 3, wherein the reaction is at least one reaction selected from the group consisting of a substitution reaction, an addition reaction, an elimination reaction, and a rearrangement reaction. An ester production method using the organic compound production method according to claim 3,
The first substance is an organic compound having a hydroxyl group,
The second substance is an acid or an ester;
In the reaction, an ester is produced by synthesizing the organic compound having a hydroxyl group and the acid or ester to produce an ester. The first substance is an organic compound having an alcoholic hydroxyl group,
The second substance is an ester;
6. The method for producing an ester according to claim 5, wherein in the reaction, the organic compound having the alcoholic hydroxyl group and the ester are subjected to a transesterification reaction to produce an ester. The second substance is a fatty acid ester;
The method for producing an ester according to claim 6, wherein in the reaction, the organic compound having the alcoholic hydroxyl group and the fatty acid ester are subjected to a transesterification reaction to produce a fatty acid ester. The first substance is a sugar;
The method for producing an ester according to claim 7, wherein in the reaction, the sugar and the fatty acid ester are transesterified to produce a sugar fatty acid ester. The first substance is sucrose;
The method for producing an ester according to claim 8, wherein in the reaction, the sucrose and the fatty acid ester are transesterified to produce a sucrose fatty acid ester. The first substance is an organic compound having an alcoholic hydroxyl group,
The second substance is an acid;
6. The method for producing an ester according to claim 5, wherein in the reaction, an ester is produced by esterifying the organic compound having the alcoholic hydroxyl group and the acid. The second substance is a fatty acid;
The method for producing an ester according to claim 10, wherein in the reaction, the fatty acid ester is produced by esterifying the organic compound having the alcoholic hydroxyl group and the fatty acid. The first substance is a sugar;
The method for producing an ester according to claim 11, wherein in the reaction, the sugar and the fatty acid are esterified to produce a sugar fatty acid ester. The first substance is sucrose;
The method for producing an ester according to claim 12, wherein in the reaction, the sucrose and the fatty acid are esterified to produce a sucrose fatty acid ester. The method for producing an organic compound according to claim 1, wherein the reaction is an ion exchange reaction. The said reaction is a manufacturing method of the organic compound in any one of Claims 1-4 performed in a flow type reactor.

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