JP2009191205A - Fatty acid ester production method and fatty acid ester production apparatus - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an efficient method for producing a fatty acid ester. <P>SOLUTION: The method for producing a fatty acid ester by a transesterification reaction between a fat and oil material and an alcohol has a plurality of units 2, 3, 4 where a fatty acid ester-generation step (step A) and an anion exchanger-regeneration step (step B) are carried out. While the step A is carried out in at least one of the units 2, 3 and 4, the step B is carried out in at least one of the other units of 2, 3 and 4, so that the fatty acid ester is continuously generated by carrying out the step A and the step B alternately in each of the units 2, 3 and 4, where the step A comprises a process for bringing the fat and oil material and the alcohol into contact with the alcohol and the fatty acid ester and an anion exchanger insoluble in the fat and oil material, and the step B comprises a regeneration process for substituting a counter ion of the anion exchanger. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to a fatty acid ester production method and a fatty acid ester production apparatus. Specifically, the present invention relates to a fatty acid ester production method and a fatty acid ester production apparatus by an ester exchange reaction between fats and oils using an anion exchanger.

  In recent years, fatty acid esters (fatty acid esters for biodiesel fuel) synthesized by transesterification of fats and oils and alcohols have attracted attention as biodiesel fuel. Compared with conventional petroleum diesel fuel (light oil), this biodiesel fuel has cleaner exhaust gas, reduced emissions of carbon monoxide, hydrocarbons, particulate matter, etc. It has many advantages such as the absence of sulfur oxides and sulfates in the gas and high lubrication performance. In addition, since it can be synthesized from waste cooking oil that contributes to environmental pollution, it is also expected as an environmentally friendly waste treatment technology.

  Moreover, the said biodiesel fuel has the advantage that it can be used for any diesel engine as it is. Moreover, since waste edible oil that contributes to environmental pollution can also be used as a raw material, it is a biomass raw material that can double the environmental burden. In the United States and Europe, oil diesel fuel mixed with about 1 to 20% biodiesel fuel has already begun to be used, and that alone reduces the load on the engine due to its high lubricity, and the environment. It has been reported that the burden on health and health is also lost. Thus, the movement to actively use biodiesel fuel, which is superior to petroleum diesel fuel in all respects, has been gradually activated in recent years.

  However, these biodiesel fuels have a big problem that they are more expensive than petroleum-based diesel fuels. In the current production process, biodiesel fuel is usually synthesized by transesterification of triglyceride, which is the main component of vegetable oil, with alcohols. As a catalyst for this synthesis, sodium hydroxide or potassium hydroxide is used as a catalyst. A soaking alkali such as is used. In the synthesis described above, since a batch reaction is exclusively used, the production apparatus is inefficient and the cost for separating the catalyst is added, and the cost of biodiesel fuel is generally higher than that of light oil. It has become.

  It is known that an ion-exchange resin having a catalytic activity for transesterification is effective as a heterogeneous phase catalyst used in the production of a fatty acid ester to be a biodiesel fuel (Non-patent Document 1). In addition to the advantage of being cheaper and more stable than the enzyme catalyst, the ion exchange resin has the advantage that saponification, which is a side reaction, does not occur because it does not have a free OH group. However, the ion exchange resin used for the production of fatty acid esters as biodiesel fuel inevitably deteriorates the catalyst performance due to its use. For industrial use, it is necessary to regenerate the catalyst performance. (Patent Document 1). Therefore, in order to produce biodiesel fuel using a heterogeneous solid catalyst, it is necessary to construct a system for producing a large amount of biodiesel fuel by efficiently performing a fatty acid ester production reaction and an ion exchange resin regeneration reaction. It was desired.

H. Toda et al., Conference Proceedings of 10th the APCChE Congress, 2D-8 (2004) JP 2006-355941 A

  The present invention was devised in view of the above problems, and provides an efficient fatty acid ester production method and production apparatus suitable for producing a large amount of biodiesel fuel using a heterogeneous solid catalyst. The purpose is to do.

  In the process of producing biodiesel fuel, fats and lower alcohols as raw materials are continuously supplied from one of the columns packed with an insoluble catalyst, and an ester reaction is conducted under the flow, and the product is supplied from the other column. The extraction method is efficient. In a transesterification reaction using an anion exchanger as a catalyst, when a fat and oil and lower alcohols as raw materials are loaded onto a column packed with an active catalyst, a fatty acid ester is produced by the transesterification reaction, and a pair of catalysts. The ions gradually change from the active form to the inactive form of fatty acid ions. That is, it was found that the inert form ratio increased at the column inlet with the feed of the raw material, and the distribution of the inactive form progressed toward the column outlet. Although the details of the mechanism of generation of the inactive form are unclear, the catalyst in the inactive form can be subjected to transesterification again by the step of reconverting to the active form, that is, regeneration. In this case, when a single column is used as a reactor, the transesterification reaction is interrupted in the regeneration step, and it is difficult to continue efficient production.

As a result of diligent investigations, the present inventors have found that the phenomenon of generation of an inactive catalyst in the transesterification reaction is similar to the multi-component competitive adsorption process without substance conversion, and a plurality of columns are successively regenerated. It was found that a continuous transesterification reaction can be carried out by using it in the reaction.
Furthermore, the present inventors show that the decrease in the activity of the catalyst layer due to the generation of the inactive form is particularly remarkable in the vicinity of the column inlet, and it is possible to improve the efficiency of the regeneration process by preferentially regenerating this part into the active form. On the other hand, since the active form exists at a relatively high density in the rear part of the column, the remaining active form can be effectively used for the esterification reaction by continuing the esterification reaction. The headline and the present invention were completed.

  That is, the gist of the present invention is a method for producing a fatty acid ester by a transesterification reaction between fats and alcohols and performing a fatty acid ester production step (A step) and an anion exchanger regeneration step (B step). While having a plurality of units and performing the A step with one or more of the units, the B step is performed with one or more of the units, and the A step and the B step are performed in each unit. By alternately performing, the fatty acid ester is continuously produced, and the step A includes a step of bringing the fats and alcohols into contact with an anion exchanger insoluble in the fats and oils, alcohols and fatty acid esters. The step B resides in a method for producing a fatty acid ester, characterized in that it comprises a regeneration step of substituting the counter ion of the anion exchanger (claim 1).

At this time, the step B is
(1) a substitution step of washing the anion exchanger with a weak acid solution;
(2) an activation step of replacing the counter ion of the anion exchanger washed in the replacement step with an alkaline solution;
(3) It is preferable to have a swelling step in which the anion exchanger that has been subjected to substitution of the counter ion in the activation step is swollen with a solvent (claim 2).

Another gist of the present invention is a fatty acid ester production apparatus using a transesterification reaction between oils and fats and alcohols,
A container having two or more ports formed therein, and having an anion exchanger insoluble in the oils and fats, alcohols and fatty acid esters therein, fatty acid ester production reaction (A reaction), and anion exchanger regeneration A plurality of containers in which a reaction (B reaction) is performed;
A mechanism for controlling the B reaction to occur in one or more of the other containers while the A reaction is performed in one or more of the containers;
A mechanism for controlling the A reaction and the B reaction alternately in each container;
When the A reaction is performed in the container, the oil and fats and alcohols are allowed to flow in from one mouth of the container, and a fatty acid ester generated from the other mouth is flown out. It exists in the fatty acid ester manufacturing apparatus (Claim 3).

  At this time, when the B reaction is performed in the container, the fatty acid ester production apparatus of the present invention allows a weak acid solution and / or an alkaline solution to flow from one mouth of the container and the weak acid solution and / or from the other mouth. Alternatively, it is preferable to provide a mechanism for discharging the discharged liquid containing the alkaline solution.

  Moreover, the fatty acid ester production apparatus of the present invention connects two or more containers in which the A reaction is performed in series through one port and the other port, and performs the B reaction in a connected container. It is preferable to provide a mechanism for removing the container from the connection and adding the container to the connection when the reaction A is performed in an unconnected container.

Furthermore, when removing the container from the connection to perform the B reaction, the fatty acid ester production apparatus of the present invention removes the most upstream container of the connection and adds a container to the connection to perform the A reaction. In some cases, it is more preferable to provide a mechanism for connecting the container to the most downstream side of the connection.
In the fatty acid ester production apparatus of the present invention, the total volume of the anion exchanger included in the container added to the connection and the total volume of the anion exchanger included in the container removed from the connection are substantially equal. Is preferably equal to (claim 7).

According to the present invention, by obtaining at least one of the following advantages, a large amount of fatty acid ester can be efficiently produced using a heterogeneous solid catalyst.
(1) The reaction is performed continuously and is efficient.
(2) A product and catalyst separation step is not required.
(3) An apparatus for catalyst regeneration is not required.
(4) The catalyst is used for the reaction and regeneration step without removing it from the column.
(5) Only the catalyst portion having reduced activity can be regenerated, and the efficiency of the regenerated drug is good.

  Hereinafter, the present invention will be described in detail with reference to examples and the like. However, the present invention is not limited to the following examples and the like, and can be arbitrarily modified and implemented without departing from the gist of the present invention.

  The method for producing a fatty acid ester of the present invention (hereinafter sometimes referred to as “the production method of the present invention”) is a method for producing a fatty acid ester by an ester exchange reaction between fats and oils, and at least producing a fatty acid ester. A process (hereinafter also referred to as “A process”) and an anion exchanger regeneration process (hereinafter also referred to as “B process”) are performed.

[A. Fatty acid ester production process (process A)]
In step A, at least a step of bringing oils and alcohols and alcohols into contact with the anion exchanger is performed. Usually, said contact is performed by distribute | circulating fats and oils and the alcohol to the container (unit) with which the anion exchanger was hold | maintained. Thereby, fats and oils and alcohol react in presence of an anion exchanger, and fatty acid ester produces | generates.

[A-1. Anion exchanger]
The anion exchanger according to the present invention acts as a heterogeneous phase catalyst in the step A, and if it is insoluble in the raw material oils and alcohols and the product fatty acid ester, the kind thereof Is optional. Here, being insoluble in fats and oils, alcohols and fatty acid esters means that the anion exchanger is not substantially dissolved in fats and oils, alcohols and fatty acid esters. For example, those that can be confirmed to have an eluate of several ppm level using an analyzer such as chromatography, and polystyrene cross-linked with divinylbenzene, polyacrylic acid, cross-linked poly (meth) acrylic acid Examples include synthetic polymers such as esters and phenol resins; ion exchangers using a crosslinked body of a naturally produced polysaccharide such as cellulose as a carrier (base). Of these, synthetic polymers are preferred, and crosslinked polystyrene is more preferred.

  Examples of the anion exchanger according to the present invention include an anion exchange resin and an anion exchange membrane. In addition, an ion exchanger may use only 1 type and may use 2 or more types by arbitrary combinations and a ratio.

Among the anion exchangers, an anion exchange resin is preferable. Examples of the anion exchange resin include a strong basic anion exchange resin and a weak basic anion exchange resin. Among them, a strong basic anion exchange resin is preferable.
Examples of strongly basic anion exchange resins according to the present invention include, for example, Diaion SA20A (Mitsubishi Chemical Corporation), Diaion SA21A (Mitsubishi Chemical Corporation), Diaion PA308 (Mitsubishi Chemical). Diaion PA306S (Mitsubishi Chemical), Diaion PA408 (Mitsubishi Chemical), Diaion PA412 (Mitsubishi Chemical), Diaion PA418 (Mitsubishi Chemical), Diaion HPA25 (Mitsubishi Chemical) Etc.) can be used.

  Strongly basic anion exchange resins are used in transesterification reactions with the counter ion as the active form. The active form is preferably a hydroxide form. However, since a commercially available strong base anion exchange resin usually has a counter ion in a chloride form, it is preferable to use the purchased strong base anion exchange resin after replacing it with a hydroxide form. As the conditions for substitution into the hydroxide form, for example, a 0.5 to 2 mol / L aqueous sodium hydroxide solution is used as the substitution agent, and the flow rate of the substitution agent is 1 L of anion exchange resin. About 1 to 10 L / hour is preferable. The liquid flow rate is usually 5 to 20 L per 1 L of anion exchange resin. Further, after the substitution is completed, the strongly basic anion exchange resin is usually washed thoroughly with water and washed with a predetermined alcohol.

  In addition, the shape of the strongly basic anion exchange resin according to the present invention is arbitrary, such as a film shape or a particle shape, depending on the usage pattern. However, among these, the particulate form is preferable. Moreover, when it is a particulate form, there is no restriction | limiting in the particle size, Usually, 10 micrometers or more, Especially 50 micrometers or more, Especially 150 micrometers or more are preferable, and it is 2 mm or less normally. If the particle size is too small, there may be industrial disadvantages such as increased liquid flow resistance. If the particle size is too large, the substance diffusion in the particles may be insufficient and the reaction efficiency may be lowered. The particle size of the strongly basic anion exchange resin can be measured by measurement using an optical microscope or mechanical measurement such as a laser method.

  In addition, the strong basic anion exchange resin according to the present invention may be used alone or both in the case of using it for the production of fatty acid ester and in the case of regenerating it. You may make it use the above together by arbitrary combinations and ratios.

The amount of the anion exchanger used in the production method of the present invention is arbitrary as long as the fatty acid ester formation reaction (that is, the transesterification reaction for the alcoholysis of fats and oils) proceeds. However, the amount of oil / fat per liter of anion exchanger is usually 0.1 kg / hour or more, preferably 0.5 kg / hour or more, and usually 50 kg / hour or less, In particular, it is preferable to be 30 kg / hour or less.
In addition, the anion exchanger according to the present invention is regenerated in Step B after use and used again.

[A-2. Oils and Fats]
Fats and oils are one of the reaction substrates in the production method of the present invention. There is no restriction | limiting in the kind of fats and oils, For example, natural fats and oils, synthetic fats and oils, a mixture thereof, etc. can be used arbitrarily. Specific examples include soybean oil, palm oil, palm oil, palm kernel oil, rice bran oil, corn oil, peanut oil, sunflower oil, olive oil, safflower oil, coconut oil, oak oil, almond oil, black walnut oil, Vegetable oils such as apricot oil, cocoa butter oil, safflower oil, safflower oil, linseed oil, flaxseed oil, cottonseed oil, rapeseed oil, kiri oil, castor oil, cottonseed stearin, sesame oil; lard oil, chicken oil, Butter oil, cod liver oil, deer oil, dolphin oil, sardine oil, mackerel oil, horse fat, pork fat, bone oil, sheep fat, cow leg oil, murine dolphin oil, shark oil, sperm whale oil, whale oil, beef tallow, cow Animal fats and oils such as bone fat; vegetable oils discarded from restaurants, food factories, general households, etc. In addition, fats and oils containing these fats and oils alone or mixed, fats and oils containing diglycerides and monoglycerides, synthesized triglycerides, synthetic triglycerides containing monoglycerides and / or diglycerides, and some of these fats and oils are oxidized or reduced, etc. Modified oils and fats modified by treatment can also be used. Furthermore, the processed fats and oils and waste oils and fats which have these fats and oils as a main component can also be used as a reaction substrate. In addition, fats and oils may use only 1 type and may use 2 or more types together by arbitrary combinations and a ratio.

  By the way, foreign substances other than fats and oils may be mixed in fats and oils. Specific examples include fats and oils, crude oil, heavy oil, light oil, mineral oil, essential oil, coal, fatty acid, sugar, metal powder, metal salt, protein, amino acid, hydrocarbon, cholesterol, flavor, pigment compound, enzyme, Perfume, alcohol, fiber, resin, rubber, paint, cement, detergent, aromatic compound, aliphatic compound, soot, glass, earth and sand, nitrogen-containing compound, sulfur-containing compound, phosphorus-containing compound, halogen-containing compound, etc. There may be. These foreign components may remain present in the fats and oils, but preferably, the fats and oils are subjected to the reaction after being removed, for example, by sedimentation, filtration, liquid separation or the like.

[A-3. Alcohol]
Alcohols are one of the reaction substrates in the production method of the present invention. There is no restriction | limiting in the kind of alcohol, Arbitrary things can be used.
However, among alcohols, those having a carbon number of usually 8 or less, preferably 5 or less are suitably used. This is because if the carbon number is too large, it may cause operational difficulties such as difficulty in separation and recovery from the reaction mixture, and may inhibit the efficiency of the substitution step, which is a component of the present invention. In addition, the minimum of carbon number is 1 or more.

  The hydrocarbon skeleton of alcohols may be linear or branched, but is preferably saturated. This is because when the carbon chain is unsaturated, there is a possibility that an oxidative modification product that inhibits the reaction is easily provided, the melting point is high and the handling is difficult, and the conditions at the time of combustion of the resulting fatty acid ester are severe.

Examples of alcohols include methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, n-butyl alcohol, t-butyl alcohol and the like.
Especially, it is preferable to use methanol and / or ethanol from the viewpoint of availability and availability of the resulting fatty acid ester.

Moreover, alcohols may be used only by 1 type and may use 2 or more types together by arbitrary combinations and a ratio.
In the production method of the present invention, alcohols act as reaction substrates for the alcoholysis (transesterification reaction) of fats and oils, and also have a solvent action for adjusting the dilution and viscosity of fats and oils. is there.

[A-4. Molar ratio of fats and alcohols]
The ratio of the number of moles of fats and oils to the number of moles of alcohol used for the reaction is arbitrary as long as the fatty acid ester formation reaction proceeds, but usually 1/30 or more, particularly 1/20 or more, more preferably 1/15 or more. Moreover, it is usually 1/1 or less, particularly preferably 1/2 or less, and further preferably 1/3 or less. If the amount of fats and oils is too large, the amount of alcohol is relatively small, and as a result, the volume of the reaction product is remarkably reduced. On the other hand, even if there are too few fats and oils, the equilibrium reaction does not proceed to the alcohololysis side, and a single phase of fats and oils that do not dissolve in alcohols may be generated, resulting in a two-phase system, and a sufficient reaction rate is achieved. You may not be able to get it. The fats and alcohols preferably form a homogeneous phase as a mixture of both.

[A-5. Other substances]
In the transesterification reaction, a substance that does not inhibit the reaction may coexist in addition to the fats and oils and alcohols that are raw materials. Examples of such substances include substances that are mixed with oils and fats and alcohols to form a homogeneous phase, such as ethers such as diethyl ether and tetrahydrofuran, and aromatic hydrocarbons such as benzene and toluene.

[A-6. Reaction conditions]
The reaction temperature is arbitrary as long as the fatty acid ester formation reaction proceeds. However, it is usually 10 ° C or higher, preferably 30 ° C or higher, and is usually 100 ° C or lower, preferably 70 ° C or lower, more preferably 60 ° C or lower. Furthermore, among them, it is more preferable to allow the reaction to proceed gently at around room temperature (25 ° C.). If the reaction temperature is too high, the heat resistance of the anion exchanger may be insufficient, and the product may be colored. On the other hand, if the reaction temperature is too low, the reaction rate is small and sufficient productivity may not be obtained.

  The reaction time (contact time) of the transesterification reaction depends on the reaction temperature and the amount of anion exchanger used, but is preferably set so that the reaction rate of fats and oils can reach the equilibrium reaction rate. For example, when the reaction temperature is 40 ° C., it is usually 5 minutes or more, preferably 10 minutes or more, and usually 2 hours or less, preferably 1 hour or less. In addition, said equilibrium reaction rate is not necessarily 100%, but changes according to molar ratio.

  The reaction pressure of the transesterification reaction is arbitrary as long as the fatty acid ester formation reaction proceeds. Although it is easy to operate under normal pressure, for example, the pressure may be increased to about 1 to 10 atm if necessary.

  The contact method between the reaction substrate and the anion exchanger as a catalyst employs a continuous method in the production method of the present invention. A large amount of fatty acid ester can be efficiently produced in the production method of the present invention by continuously carrying out the fatty acid ester production reaction in the A step and also carrying out the B step described later by a continuous method.

  In addition, the reaction system may contain other components other than the anion exchanger, the reaction substrate, and the reaction solvent according to the present invention as long as the production reaction of the fatty acid ester is not inhibited. When the example is given, the foreign-material component etc. which may be contained in fats and oils are mentioned. In addition, as for another component, only 1 type may be contained and 2 or more types may be contained by arbitrary combinations and ratios.

[A-7. Advantages of performing step A]
According to A process mentioned above, 1 or 2 or more can be acquired among the following advantages.
(I) The step of catalyst separation, which is a problem of a soaking alkali catalyst, can be eliminated.
(Ii) The production amount of fatty acid ester per strong basic anion exchanger to be used is large.
(Iii) The amount of fatty acid ester produced per hour is large.
(Iv) Productivity is high because oils and fats can be used at high concentrations.
(V) Anion exchangers are generally less expensive than complex metal oxides and have stable catalytic activity.
(Vi) Even when the performance of the anion exchanger is deteriorated, the exchange group can be easily regenerated.
(Vii) In particular, the strong base ion exchange resin according to the present invention has a low rate of decrease in catalytic activity over time.

[B. Anion exchanger regeneration process (process B)]
In step B, at least a regeneration step for replacing the counter ion of the anion exchanger is performed. Thereby, it is possible to regenerate the anion exchanger that has lost its activity by being used in the A process and to use it again in the A process. Further, in step B, steps other than the regeneration step may be performed. Examples of the anion exchanger regeneration method performed in step B include the following examples.

[B-1. Example of anion exchanger regeneration method]
Examples of the method for regenerating the anion exchanger include the following (1) substitution step, (2) activation step, and (3) swelling method.
(1) A substitution step of washing the anion exchanger used for the production of the fatty acid ester with a weak acid solution.
(2) An activation step of replacing the counter ion of the anion exchanger washed in the replacement step with an alkaline solution.
(3) A swelling step in which the anion exchanger that has been subjected to counter ion substitution in the activation step is swollen with a solvent.
In the regeneration method of the present invention, steps other than the substitution step, the activation step, and the swelling step can be performed as necessary.

[B-1-1. Replacement process]
In the substitution step of this example, the anion exchanger used for the production of the fatty acid ester is washed with a weak acid solution. Thereby, the fats and oils adhering to the anion exchanger are removed. Further, in the step A, a hydrolysis reaction occurs in equilibrium with the transesterification reaction, thereby generating a free fatty acid. In the substitution step, this free fatty acid can also be washed. That is, the fatty acid ions adsorbed on these anion exchangers can be removed by substituting them with lower weak acid ions with a weak acid solution. In the substitution step, there is also a meaning of performing solvent substitution.

  The weak acid solution used for washing is not particularly limited as long as the oils and fats can be removed. In addition, a weak acid solution may use only 1 type and may use 2 or more types together by arbitrary combinations and a ratio. In addition, when two or more kinds of weak acid solutions are used in combination, they may be used in combination. However, if washing is performed twice or more, the weak acid solution may be used separately each time.

  Examples of the weak acid used in the weak acid solution include organic acids such as citric acid, acetic acid, malic acid, and formic acid. In particular, when a by-product such as glycerin produced as a by-product in step A is used as an edible or cosmetic raw material, a weak acid that is safe even if taken into the human body, such as citric acid, acetic acid, malic acid, is preferable. In particular, when citric acid is used, it is easy to separate citric acid and oleic acid, so that it is easy to treat a mixture of citric acid and oleic acid generated as a waste liquid in step A and reuse citric acid. . In addition, weak acid may use only 1 type and may use 2 or more types together by arbitrary combinations and a ratio.

  On the other hand, examples of the solvent that dissolves the weak acid in the weak acid solution include alcohols such as methanol, ethanol, and isopropyl alcohol; and organic solvents such as ethers such as tetrahydrofuran and 1,4-dioxane. In particular, when a by-product produced as a by-product in the step A is used as an edible or cosmetic raw material, a solvent that is safe even if taken into the human body, such as ethanol, is preferable. Moreover, when using the said by-product as an industrial raw material, if methanol etc. are used, it is economically useful and preferable. In addition, only 1 type may be used for a solvent and it may use 2 or more types together by arbitrary combinations and a ratio.

  The concentration of the weak acid solution may be appropriately adjusted so as to be within a practical range, and is usually 0.01 mol / L or more, preferably 0.1 mol / L or more, usually 5 mol / L or less, especially 1 mol / L or less. Is preferred.

  The weak acid solution may contain components other than the weak acid and the solvent as long as the effects of the present invention are not significantly impaired. In addition, as for components other than a weak acid and a solvent, only 1 type may be contained and 2 or more types may be contained by arbitrary combinations and ratios.

  The amount of the weak acid solution used is arbitrary as long as oils and fats can be removed, but usually 0.1 mol equivalent or more, particularly 0.5 mol, etc. with respect to the ion exchange capacity of the anion exchanger. The amount is preferably at least 1 mol, particularly preferably at most 100 mol, more preferably at most 50 mol, particularly preferably at most 10 mol. This is because if the amount of the weak acid solution is too small, the entire amount of the fatty acid adsorbed may not be replaced, resulting in insufficient regeneration. If the amount is too large, it may be inefficient and uneconomical due to unnecessary handling of the weak acid. .

  Although there is no restriction | limiting in the temperature in a substitution process, Usually, 0 degreeC or more, especially 5 degreeC or more, especially 25 degreeC or more is preferable, and usually 60 degreeC or less, especially 55 degreeC or less, Especially 50 degreeC or less is preferable. If the temperature is too low, there is a possibility that the liquid phase viscosity is increased and the washing efficiency is lowered, and if it is too high, chemical decomposition and deterioration of the anion exchanger may be promoted.

  The time required for the substitution step is usually 0.1 hour or longer, preferably 1 hour or longer, usually 20 hours or shorter, especially 10 hours or shorter, particularly preferably 5 hours or shorter.

  Further, the substitution step may be performed once or may be performed in two or more times.

[B-1-2. Activation process]
In the activation step of this example, the anion exchanger washed in the substitution step is replaced with a counter ion to regenerate its ion form from a weak acid form such as a lower carboxylic acid form to a hydroxide form. Thereby, the catalytic activity of the anion exchanger is recovered.
An alkaline solution is used to replace the counter ion. As the alkaline solution, an alkali hydroxide aqueous solution or a lower alcohol solution is usually used. In addition, an alkaline solution may use only 1 type and may use 2 or more types together by arbitrary combinations and a ratio.
As the alkali hydroxide, for example, sodium hydroxide, potassium hydroxide, lithium hydroxide, tetramethylammonium hydroxide and the like are used, and among them, sodium hydroxide and potassium hydroxide are preferable. The concentration of the alkali hydroxide is usually 0.1 mol / L or more, preferably 0.3 mol / L or more, and usually 5 mol / L or less, preferably 2 mol / L or less.
The amount of alkali hydroxide used is usually 0.1 times or more, preferably 0.5 times or more, and usually 10 times or less the exchange capacity of the anion exchanger filled in the system. Preferably it is 5 times or less. The time required for the activation step is usually 0.1 hours or more and 2 hours or less. In addition, when an alkali hydroxide is used as an aqueous solution, the inside of the system may be washed with water before and after the activation step.

  The activation step may be performed once or may be performed in two or more steps.

[B-1-3. Swelling process]
In the swelling step of this example, the anion exchanger that has been subjected to substitution of counter ions in the activation step is swollen with a solvent. By causing the anion exchanger according to the present invention to swell in an amphiphilic environment, the anion exchanger is transferred to a non-aqueous fatty acid ester reaction system that is not directly mixed in the aqueous regeneration (substitution) step. Can do. For this reason, the catalytic activity of the anion exchanger is increased, and the production efficiency of the fatty acid ester can be improved.

  The solvent used for swelling is optional as long as it can swell the anion exchanger and does not impair the activity of the counter ion. For example, alcohols and reaction solvents mentioned in the description of the step A can be used. Of these, methanol and / or ethanol are preferred. This is because it is used as it is for the production of fatty acid esters. In addition, from the viewpoint of preventing impurities from being mixed into the reaction system when an anion exchanger is used in the production of fatty acid esters, alcohols that are reaction substrates for the production of the fatty acid esters may be used as the solvent. preferable. In addition, the said solvent may use only 1 type and may use 2 or more types together by arbitrary combinations and a ratio. Moreover, when using 2 or more types of solvents together, you may mix and use, but if swelling is performed 2 times or more, you may use a solvent for each time.

  The solvent used for the swelling may contain components other than the above-described solvents as long as the effects of the present invention are not significantly impaired. In addition, as for components other than a solvent, only 1 type may be contained and 2 or more types may be contained by arbitrary combinations and ratios.

  The amount of the solvent used in the swelling step is arbitrary as long as the effect of the present invention is not significantly impaired, but usually 0.5 times or more of the volume of the anion exchanger subjected to substitution of the counter ion in the activation step. Among these, 1-fold amount or more, particularly 5-fold amount or more is preferable, and usually 100-fold amount or less, especially 50-fold amount or less, particularly 10-fold amount or less is preferable. If the amount of the solvent used is too small, the swelling is insufficient and the production efficiency of the fatty acid ester may be lowered. On the other hand, if the amount of solvent used is too large, it may be uneconomical and inefficient.

  Although there is no restriction | limiting in the temperature in a swelling process, Usually, 0 degreeC or more, especially 5 degreeC or more, especially 25 degreeC or more is preferable, and below the boiling point of a solvent, below 60 degreeC, especially 50 degreeC or less is preferable. If the temperature is too low, the liquid viscosity is high, so that the swelling speed may be slow. If it is too high, there is a possibility of bumping of the solvent or vapor scattering.

  The time required for the swelling step is usually 0.1 hour or more, preferably 1 hour or more, usually 20 hours or less, especially 10 hours or less, particularly preferably 5 hours or less.

  Moreover, the swelling process may be performed once or may be performed in two or more times.

[B-2. Others]
In step B described above, as long as the anion exchanger can be regenerated, other steps are performed at any time before, during, and after the replacement step, activation step, and swelling step described above. You may do it.
Further, in each of the above steps, the liquid passing direction may be performed from any direction above and below the system.

[C. Production method and production apparatus of fatty acid ester of the present invention]
The method for producing a fatty acid ester of the present invention includes a plurality of units for performing the above-described A step and B step, and performing the B step with one or more other units while performing the A step with one or more of the units. is there. And fatty acid ester is produced | generated continuously by performing A process and B process alternately within each unit.
The group of units passing through the A process and the group of units passing through the B process may be the same or different, but the sum of the anion exchangers present in the units of each group must be equal. Is preferred.

This manufacturing method will be described in detail below with reference to a manufacturing apparatus (hereinafter referred to as “the manufacturing apparatus of the present invention”) as a preferred specific example in which this is realized.
That is, the manufacturing apparatus of the present invention
(I) A container having two or more mouths, which has an anion exchanger insoluble in fats and oils, alcohols and fatty acid esters therein, and a fatty acid ester production reaction (A reaction. A plurality of containers in which an anion exchanger regeneration reaction (B reaction, corresponding to the above-described B step) is performed;
(II) a mechanism (first mechanism) for controlling the B reaction to be performed in one or more of the other containers while the A reaction is performed in one or more of the containers;
(III) a mechanism (second mechanism) for controlling the A reaction and the B reaction alternately in each of the containers;
(IV) When the A reaction is performed in the container, a mechanism (third mechanism) for causing the fats and alcohols to flow in from one mouth of the container and causing the fatty acid ester generated from the other mouth to flow out. It is characterized by having.

Moreover, as a preferable aspect,
(V) When the B reaction is carried out in the container, a weak acid solution and / or an alkaline solution is introduced from one port of the container, and a discharged liquid containing the weak acid solution and / or the alkaline solution is discharged from the other port. Mechanism (fourth mechanism), and
(VI) Two or more containers in which the A reaction is performed are connected in series through one port and the other port, and when the B reaction is performed in the connected container, the container is removed from the connection and connected. A mechanism (fifth mechanism) for adding the container to the connection when performing the A reaction in a non-container,
What has any one or more of these is mentioned.

In addition, the above (VI) removes the most upstream container of the connection when the container is removed from the connection to perform the B reaction, and the connection when the container is added to the connection to perform the A reaction. It is preferable to include a mechanism (sixth mechanism) for connecting the container to the most downstream side. Here, upstream and downstream refer to upstream and downstream of the flow of fluid (oils and fats, alcohols, fatty acid esters, and the like) related to the A reaction.
Furthermore, it is preferable that the total volume of the anion exchanger included in the container added to the connection is substantially equal to the total volume of the anion exchanger included in the container removed from the connection. Here, the total volume of the anion exchanger is substantially the same, the amount of ion exchange of the added anion exchanger and the removed anion exchanger are equal to the extent that the reaction amount of fatty acid ester production does not change. That means.

[C-1. container]
A container having two or more mouths is used. From the viewpoint that the production apparatus of the present invention is preferably a flow-through type, a column is usually used as a container. This container has an anion exchanger inside, and constitutes a unit for performing the A step and the B step in the production method of the present invention. Hereinafter, the column will be described in detail as an example.

The anion exchanger, which is a catalyst, is usually used while being packed in a column, which is a reactor. The column can be of any shape, but is preferably cylindrical. The length of the column is usually 0.1 m or more, preferably 0.3 m or more, more preferably 0.5 m or more, and usually 10 m or less, preferably 5 m or less, more preferably 3 m or less. If the column is too short, it is inefficient as a catalytic reactor, and if the column is too long, the pressure loss at the time of liquid passage may increase and liquid passage may not be possible.
The inner diameter of the column is usually 0.01 m or more, preferably 0.3 m or more, and usually 5 m or less, preferably 2 m or less. If the column inner diameter is too small, it is difficult to pack the catalyst, and if the column inner diameter is too large, the catalyst is not uniformly packed and the esterification reaction is inefficient.

Use multiple columns. Among these, it is preferable to use three or more. Each column may be an individual design, but preferably have the same shape.
The arrangement of the columns is arbitrary, but at least two or more columns are connected in series as a reactor for performing the A reaction, and at least one more column is subjected to a regeneration step to perform the B reaction. It is preferable that the pipe is connected via a switching valve.

[C-2. A Reaction Conditions]
The raw oils and fats and alcohols are supplied to the column inlet in a mixed state or independently. The total feed rate of fats and oils and lower alcohols is usually 0.1 kg / hour or more, preferably 0.5 kg / hour or more, usually 50 kg / hour or less, preferably 30 kg / hour or less per liter of catalyst. .
The reaction conditions such as the reaction temperature are the same as those described in the description of the step A.

[C-3. Operation of A reaction]
The A reaction, that is, fatty acid ester formation reaction (transesterification reaction) is preferably performed by connecting a column filled with at least two or more active catalysts in series through one port and the other port. In this case, the reaction product is collected from the outlet of the most downstream column. While the A reaction is being performed, regeneration of the anion exchanger with reduced activity (B reaction) is simultaneously performed in another column.

[C-4. Conditions for B reaction]
The conditions for the B reaction are the same as those described in the description of the B process.
The direction of liquid flow may be from any of the columns.

[C-5. Switch column]
After completion of the B reaction in the previous section, one of the columns used for the A reaction is disconnected from the reaction system connected in series, and the piping is switched to provide the B reaction. At this time, it is preferable that the column to be disconnected is the column at the most upstream among the columns connected in series. This is because the anion exchanger in the most upstream column loses the most activity among the columns used in the A reaction. Here, upstream and downstream refer to upstream and downstream of the flow of fluid (oils and fats, alcohols, fatty acid esters, and the like) related to the A reaction.
At the same time, the column after completion of the B reaction is connected to the reaction system of the connected column for use in the A reaction as described above and used as a part of the transesterification reactor. At this time, the newly connected column is preferably connected to the most downstream side of the transesterification reactor composed of a series of columns connected in series. This is because the reaction is most complete and the product with high purity is obtained at the most downstream.
These series of operations are completed in a short time at the same time by switching the valve or the like, so that the A reaction (transesterification reaction) can be continued without interruption.

[C-6. Reaction product]
The liquid phase obtained from the outlet of the reactor is usually separated into a fatty acid ester layer and a glycerin layer. Centrifugation can also be used to promote the separation. If necessary, the fatty acid ester layer is subjected to water washing, alkali washing, adsorbent treatment, etc., and further alcohol is removed to produce a product. As the adsorbent, activated carbon, acid clay, diatomaceous earth, or the like can be used. On the other hand, a glycerol layer is isolate | separated by specific gravity difference, and glycerol is collect | recovered by a well-known method.

[C-7. Embodiment]
Hereinafter, an embodiment of a fatty acid ester production apparatus and production method of the present invention will be described with reference to the drawings. In addition, this invention is not limited to the following embodiment, In the range which does not deviate from the summary of this invention, it can change arbitrarily and can implement.

  FIG. 1 is a diagram schematically showing an outline of a fatty acid ester production apparatus as one embodiment of the present invention. In addition, in FIG. 1, the piping concerning the reaction system of the A reaction (the piping through which fats and oils, alcohols, fatty acid esters and glycerin circulate) is shown by a solid line, and the piping concerning the reaction system of the B reaction (the alkyl hydroxide and the fatty acid are (Circulating piping) is indicated by a one-point difference line, and control by the controller 100 is indicated by a broken line.

  The manufacturing apparatus 1 includes columns 2, 3, and 4 as containers (units) that are systems for performing the A process (A reaction) and the B process (B reaction). Each column 2, 3, 4 has an opening (not shown) one above and below in the figure, and an anion exchanger (not shown) is placed in each column 2, 3, 4 in the inside. Are filled with the same total volume.

  The production apparatus 1 includes a substrate tank 5 as a reaction substrate supply source for supplying oils and alcohols used in the step A to the columns 2, 3, and 4. The substrate tank 5 is connected via a pipe 6 and a valve 7. The columns 2, 3 and 4 are connected to the upper openings in the figure. The substrate tank 5 may include an oil / fat tank and an alcohol tank separately in order to supply the oil / fat and the alcohol separately. Further, the pipe 6 is provided with a pump (not shown) for sending oils and fats and alcohols, so that the oils and alcohols flow into the columns 2, 3 and 4. Yes. The valve 7 switches the connection between the substrate tank 5 and the columns 2, 3, 4 in accordance with the control of the controller 100, thereby supplying fats and oils and alcohols to any of the columns 2, 3, 4. Can be controlled.

  When fats and oils and alcohols are supplied, the A reaction proceeds in the columns 2, 3, and 4, and fatty acid esters and glycerin are generated. The produced fatty acid ester and glycerin are designed to flow out from the lower openings of the columns 2, 3, and 4 in the figure. Thus, in order to collect | recover the fatty acid ester and glycerol which are produced | generated by A process, the manufacturing apparatus 1 is provided with the collection tank 8. FIG. The recovery tank 8 is connected to the lower openings of the columns 2, 3, and 4 in the figure via a pipe 9 and a valve 10. As a result, the fatty acid ester and glycerin flowing out from the columns 2, 3, and 4 are recovered in the recovery tank 8. The valve 10 switches the connection between the columns 2, 3, 4 and the collection tank 8 according to the control of the controller 100, whereby the fatty acid ester and glycerin flowing out from any of the columns 2, 3, 4 are collected. It can be done.

Furthermore, the manufacturing apparatus 1 includes a pipe 11 that connects the lower opening of the column 2 and the upper opening of the column 3, the lower opening of the column 3 and the upper opening of the column 4. And a pipe 13 for connecting the opening on the lower side of the column 4 in the drawing and the opening on the upper side of the column 2 in the drawing. Thereby, the fatty acid ester and glycerin which flow out from the column 2, the column 3 and the column 4, and the unreacted oils and alcohols flow into the column 3, the column 4 and the column 2, respectively.
The pipes 11, 12, and 13 are provided with valves 14, 15, and 16, respectively, and the controller 100 controls the opening and closing of these valves 14, 15, and 16, so that fluid flows through the pipes 11, 12, and 13. Whether it flows or not is controlled.

  Therefore, when the A reaction is performed in the columns 2, 3, 4 by the substrate tank 5, the pipes 6, 11, 12, 13 and the valves 7, 14, 15, 16, the one of the columns 2, 3, 4 A third mechanism is configured to allow oils and fats and alcohols to flow in from the mouth (upper opening in the figure) and flow out fatty acid ester generated from the other mouth (lower mouth in the figure).

  The manufacturing apparatus 1 includes a regeneration liquid tank 17 as a regeneration liquid supply source for supplying the regeneration liquid (alkaline solution here) used in the B process to the columns 2, 3, and 4. And through the valve 19 are connected to the lower openings of the columns 2, 3 and 4 in the figure. The pipe 18 is provided with a pump (not shown) for sending an alkaline solution, whereby the alkaline solution is supplied to the columns 2, 3, 4. The valve 19 switches the connection between the regenerative liquid tank 17 and the columns 2, 3, 4 according to the control of the controller 100, so that the alkaline solution is supplied to any of the columns 2, 3, 4. It can be controlled.

  Therefore, when the B reaction is performed in the columns 2, 3, and 4 by the regeneration liquid tank 17, the pipe 18, and the valve 19, from one of the ports 2, 3, and 4 (lower opening in the figure) A fourth mechanism is configured to allow the weak acid solution and / or the alkali solution to flow in and the discharged liquid containing the weak acid solution and / or the alkali solution to flow out from the other port (the upper opening in the figure).

  The manufacturing apparatus 1 includes a recovery tank 20 for recovering the effluent generated in the process B, and the recovery tank 20 is connected to the upper opening of the columns 2, 3, 4 in the figure via a pipe 21 and a valve 22. Has been. As a result, the discharged liquid containing fatty acids, fats and oils flowing out from the columns 2, 3 and 4 is collected in the collection tank 20. The valve 22 switches the connection between the columns 2, 3, 4 and the collection tank 20 according to the control of the controller 100, so that the effluent discharged from any of the columns 2, 3, 4 can be collected. It has become.

  The controller 100 controls switching and opening / closing of the valves 7, 10, 14, 15, 16, 19, 22. The controller 100 is configured by a computer such as a CPU (Central Processing Unit), a RAM (Random Access Memory), a ROM (Read Only Memory), and the like, and an electronic computer including an interface unit. The said electronic computer comes to exhibit the function.

  The controller 100 switches the valves 7, 10, 14, 15, 16, 19, 22, while the A reaction is performed in one or more of the columns 2, 3, 4, Thus, control is performed so that the B reaction is performed. Therefore, these valves 7, 10, 14, 15, 16, 19, 22 and the controller 100 constitute the first mechanism described above.

  In addition, the controller 100 switches the valves 7, 10, 14, 15, 16, 19, and 22 to control the A reaction and the B reaction alternately in each of the columns 2, 3, and 4. ing. Therefore, these valves 7, 10, 14, 15, 16, 19, 22 and the controller 100 constitute the second mechanism described above.

  Further, the controller 100 switches the valves 7, 10, 14, 15, 16, 19, and 22 to connect two or more columns 2, 3, and 4 in which the A reaction is performed through one port and the other port in series. And when the B reaction is performed in the connected columns 2, 3 and 4, the column 2, 3 and 4 are removed from the connection, and the A reaction is performed in the unconnected columns 2, 3 and 4. In such a case, control is performed so that the columns 2, 3, and 4 are added to the connection. At this time, among the columns 2, 3, and 4 connected to perform the A reaction, the controller 100 removes the columns 2, 3, and 4 from the connection to perform the B reaction. When the columns 2, 3, and 4 are added to the connection to perform the A reaction, the columns 2, 3, and 4 are controlled to be connected to the most downstream side of the connection. . Here, upstream and downstream refer to upstream and downstream of the flow of fluid (oils and fats, alcohols, fatty acid esters, glycerin, and the like) related to the A reaction. Therefore, these valves 7, 10, 14, 15, 16, 19, 22 and the controller 100 constitute the fifth mechanism and the sixth mechanism described above.

  Since the manufacturing apparatus 1 of the present embodiment is configured as described above, in use, the controller 100 switches the valve 7 to connect the substrate tank 5 and the column 2 and opens the valve 14 to downstream of the column 2. The column 3 is connected in series and the valves 15 and 16 are closed, and the valve 10 is switched to connect the column 3 and the recovery tank 8. Further, the controller 100 switches the valve 19 to connect the regenerative liquid tank 17 and the column 4, and switches the valve 22 to connect the column 4 and the recovery tank 20. The outline of the reaction apparatus 1 at this time is schematically shown in FIG. In FIG. 2, the illustration of valves and pipes through which no fluid flows is omitted. In FIG. 2, the hatched portion represents a state where the anion exchangers in the columns 2 and 4 are deactivated. Furthermore, in FIG. 2, the arrow represents the direction of fluid flow.

  As a result, the process A is performed in the system constituted by the columns 2 and 3, and at the same time, the process B is performed in the system constituted by the column 4. Fatty acid ester and glycerin are produced by the progress of step A. At this time, since the column 2 and the column 3 are connected in series, the production efficiency of the fatty acid ester is good. However, the anion exchanger in the column 2 is gradually deactivated with the passage of time, and the production efficiency of the fatty acid ester is also lowered. On the other hand, as the B process proceeds, the anion exchanger in the column 4 is regenerated by being washed and replaced.

  Next, the controller 100 switches the valve 7 to connect the substrate tank 5 and the column 3, opens the valve 15, connects the column 4 in series downstream of the column 3, and closes the valves 14 and 16. To switch the column 4 and the recovery tank 8 together. As a result, the column 2 connected to the most upstream for the A reaction is removed from the system for performing the A reaction, and the column 4 is connected to the most downstream of the system for performing the A reaction. Further, the controller 100 switches the valve 19 to connect the regenerative liquid tank 17 and the column 2, and switches the valve 22 to connect the column 2 and the recovery tank 20. The outline of the reaction apparatus 1 at this time is schematically shown in FIG. In FIG. 3, the illustration of valves and pipes through which no fluid flows is omitted. Further, in FIG. 3, the hatched portion represents a state where the anion exchanger in the column 2 is deactivated. Furthermore, in FIG. 3, the arrow represents the direction in which the fluid flows.

  As a result, the A process is performed in the system constituted by the columns 3 and 4, and at the same time, the B process is performed in the system constituted by the column 2. Fatty acid ester and glycerin are produced by the progress of step A. At this time, since the column 4 is regenerated, transesterification can be performed very efficiently. On the other hand, as the B process proceeds, the anion exchanger in the column 2 is regenerated by being washed and replaced.

  Thereafter, the controller 100 controls the valves 7, 10, 14, 15, 16, 19, and 22 in the same manner, and repeats regeneration of the anion exchanger through the B process in the order of the column 3, the column 4, and the column 2. While performing, A reaction is performed in the other column which has not performed B process. As described above, since the A process and the B process are alternately performed in each column (unit), the fatty acid ester can be continuously generated in this embodiment.

Moreover, according to this embodiment, the following advantages are obtained.
(1) The reaction is performed continuously and is efficient.
(2) A product and catalyst separation step is not required.
(3) An apparatus for catalyst regeneration is not required.
(4) The catalyst is used for the reaction and regeneration step without removing it from the column.
(5) Only the catalyst portion having reduced activity can be regenerated, and the efficiency of the regenerated drug is good.

In addition, in said embodiment, you may change and implement in the range which does not deviate from the summary of this invention.
For example, a washing column may be provided as a washing system for washing the fatty acid ester and glycerin collected in the collecting tank 8, and a drying column may be provided as a drying system for drying.
Further, for example, the number of columns 2, 3, and 4 may be increased or decreased, or some or all of the columns 2, 3, and 4 may be connected in parallel as necessary.
Further, for example, a weak acid solution as a cleaning solution may be used together with an alkaline solution as a regeneration solution.
Further, for example, a recovery system for separating and recovering oils and fatty acids and the like contained in the waste liquid recovered in the recovery tank 20 may be provided.

  According to the present invention, a fatty acid ester can be produced efficiently and can be used as a biodiesel fuel with a small environmental load. The produced fatty acid ester can be used as it is, or appropriately mixed with light oil or the like.

It is a figure which shows typically the outline | summary of the fatty-acid-ester manufacturing apparatus as one Embodiment of this invention. It is a figure which shows typically the outline | summary of the usage condition of the fatty-acid-ester manufacturing apparatus as one Embodiment of this invention. It is a figure which shows typically the outline | summary of the usage condition of the fatty-acid-ester manufacturing apparatus as one Embodiment of this invention.

Explanation of symbols

DESCRIPTION OF SYMBOLS 1 Manufacturing apparatus 2,3,4 Column 5 Substrate tank 6,9,11,12,13,18,21 Piping 7,10,14,15,16,19,22 Valve 8,20 Recovery tank 17 Regeneration liquid tank

Claims (7)

A method for producing a fatty acid ester by a transesterification reaction between fats and alcohols,
A plurality of units for performing a fatty acid ester production step (step A) and an anion exchanger regeneration step (step B);
While performing step A with one or more of the units, performing step B with one or more of the other units,
By alternately performing the A step and the B step within each unit, a fatty acid ester is continuously generated,
The step A includes a step of bringing the fats and alcohols into contact with an anion exchanger insoluble in the fats and oils, alcohols and fatty acid esters,
The method of producing a fatty acid ester, wherein the step B includes a regeneration step of substituting the counter ion of the anion exchanger. Step B is
(1) a substitution step of washing the anion exchanger with a weak acid solution;
(2) an activation step of replacing the counter ion of the anion exchanger washed in the replacement step with an alkaline solution;
(3) The method for producing a fatty acid ester according to claim 1, further comprising a swelling step in which the anion exchanger having been subjected to counter ion substitution in the activation step is swollen with a solvent. A fatty acid ester production apparatus using a transesterification reaction between fats and alcohols,
A container having two or more ports formed therein, and having an anion exchanger insoluble in the oils and fats, alcohols and fatty acid esters therein, fatty acid ester production reaction (A reaction), and anion exchanger regeneration A plurality of containers in which a reaction (B reaction) is performed;
A mechanism for controlling the B reaction to occur in one or more of the other containers while the A reaction is performed in one or more of the containers;
A mechanism for controlling the A reaction and the B reaction alternately in each container;
When the A reaction is performed in the container, the oil and fats and alcohols are allowed to flow in from one mouth of the container, and a fatty acid ester generated from the other mouth is flown out. Fatty acid ester production equipment. A mechanism for causing a weak acid solution and / or an alkaline solution to flow from one port of the vessel and a drain solution containing the weak acid solution and / or the alkaline solution to flow out from the other port when the B reaction is performed in the vessel; The apparatus for producing a fatty acid ester according to claim 3, wherein the apparatus is provided. Two or more containers in which the A reaction is performed are connected in series through one port and the other port,
A mechanism is provided that removes the container from the connection when the B reaction is performed in a connected container, and adds the container to the connection when the A reaction is performed in a non-connected container. The fatty acid ester production apparatus according to claim 3 or 4. When removing a container from the connection to perform the B reaction, the container at the most upstream side of the connection is removed, and when adding a container to the connection to perform the A reaction, a container is disposed at the most downstream side of the connection. The apparatus for producing a fatty acid ester according to claim 5, further comprising a mechanism for connection. 6. The total volume of the anion exchanger included in the container added to the connection is substantially equal to the total volume of the anion exchanger included in the container removed from the connection. Or the fatty acid ester production apparatus according to 6;

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