JP2007126547A - Polyalkylene carbonate production method - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To establish a technique of industrially and stably producing a polyalkylene carbonate by making it possible to handle the polymer during production without raising any environmental and hygienic problems in a reaction of carbon dioxide with an epoxide. <P>SOLUTION: A polyalkylene carbonate production method having no environmental and hygienic problems has been found out by polymerizing carbon dioxide and an epoxide in the presence of a hydroxyl- or carboxyl-containing organic compound or water in a solvent containing a carbonate solvent or an ether solvent capable of dissolving the polyalkylene carbonate. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a process for producing a polyalkylene carbonate by reacting carbon dioxide with an epoxide.

  Carbon dioxide is released on the earth in large quantities due to industrial production activities or the respiration of living organisms, causing global warming. However, since carbon dioxide has poor reactivity, it cannot be effectively used as a resource. If this carbon dioxide gas can be used effectively as an industrial resource, it is significant from the viewpoint of effective use of limited resources on the earth.

  As a method of industrially utilizing such abundant carbon dioxide gas, a synthetic resin production method using carbon dioxide gas as a raw material has been proposed. For example, the Chemical Society of Japan Journal 1982, No. 2, page 295 describes a method for producing a synthetic resin using carbon dioxide as a raw material. In this production method, a reaction between zinc acetate and an aliphatic dicarboxylic acid is used as a catalyst. A product or a reaction product of alkylzinc and water is used ([Non-Patent Document 1]).

  Polymer Journal 1981, Vol. 13, page 407 describes a method for producing a synthetic resin using carbon dioxide as a raw material. In this production method, reaction products of zinc hydroxide and various organic carboxylic acids as a catalyst are described. Is used. ([Non-Patent Document 2])

  These catalysts have a problem of low polymerization activity. However, for the purpose of improving the activity of the catalyst, as described in JP-A-2-47134, a method of reacting zinc oxide and aliphatic dicarboxylic acid in the presence of an organic solvent by a mechanical pulverization means has been reported. . Furthermore, as disclosed in JP-A-3-28227, zinc sulfide is added to a catalyst system composed of a reaction between zinc oxide and an aliphatic dicarboxylic acid to further improve the activity. ([Patent Document 2])

  In this reaction, it is also known that the molecular weight of the resulting polyalkylene carbonate can be controlled by adding a small amount of an organic acid such as acetic acid or benzoic acid without impairing the catalytic activity. ([Patent Document 3], [Patent Document 4])

  When producing polyalkylene carbonates using these zinc-containing catalysts, the polymerization solvents are aliphatic hydrocarbons such as hexane and octane, aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and carbon tetrachloride. Has been used. In general, aliphatic hydrocarbons and aromatic hydrocarbon solvents cannot dissolve polyalkylene carbonates up to the polymer concentration used in industrial solution polymerization. Therefore, in the polymerization using these solvents, the polyalkylene carbonate is polymerized in a precipitated state. Many of the polyalkylene carbonates are amorphous polymers and have a glass transition point lower than the temperature used for the polymerization. Therefore, the polymer precipitated during the polymerization is indefinite and easy to unite, and handling of the produced polymer becomes very difficult. Further, since the catalyst is taken into the precipitated polymer during the polymerization, the activity tends to be low. Furthermore, when removing the catalyst after polymerization, filtration or washing with a dilute acid aqueous solution, dilute alkaline aqueous solution, etc. is performed. However, since the operation cannot be performed in a state where the polyalkylene carbonate is precipitated, it is necessary to replace the polyalkylene carbonate with a soluble solvent. Yes, irrational operation was necessary.

On the other hand, many halogenated solvents such as dichloromethane can dissolve polyalkylene carbonate, but there are various problems in environmental hygiene for industrial use. For example, dichloromethane has become clear that it is a harmful substance that directly affects the human body as an environmentally destructive substance that causes ozone depletion and global warming. . Therefore, it is a highly regulated substance, and it is necessary to completely prevent leakage and release to the atmosphere during manufacturing, and it is difficult to use it for industrial mass production. Furthermore, from the viewpoint of product hygiene, it is necessary to make the amount of residual solvent in the product as zero as possible, which requires a large amount of solvent removal energy.
JP-A-2-47134 JP-A-3-28227 US Pat. No. 4,943,777 JP 55-12156 Journal of the Chemical Society of Japan, 1982, No. 2, page 295 Polymer Journal 1981 Volume 13 Page 407

  The present invention has been made in view of the above points, and there is no problem in terms of environment and hygiene in the reaction of carbon dioxide and epoxide, the polymer can be handled during production, and the polyalkylene carbonate is stably produced. Is to establish the technology to industrially manufacture.

  As a result of intensive studies to solve the above problems, the inventors of the present invention have developed a carbonate-based solvent or an ether-based solvent capable of dissolving polyalkylene carbonate in the presence of an organic compound having a hydroxyl group or a carboxylic acid group, or water. By polymerizing using the solvent which contains it, the polyalkylene carbonate manufacturing method which does not have a problem on environment and hygiene was discovered, and it came to complete this invention.

  In addition to having the ability to dissolve polyalkylene carbonate, the polymerization solvent has no environmental damage and excellent hygiene, does not adversely affect the polymerization activity, has no problem in removing the catalyst after polymerization, polyalkylene It is necessary to have excellent solvent separation from carbonate. As a result of intensive studies, it has been found that a carbonate-based solvent or an ether-based solvent satisfies these requirements. In particular, dimethyl carbonate, methyl ethyl carbonate, 1,3-dioxolane, dioxane and the like produce polyalkylene carbonate having a temperature of 25 ° C. or higher. It has been found that a solvent that dissolves at 5% by weight or more at temperature is useful, and has led to the invention.

  According to the present invention, in production in which the molecular weight of the polyalkylene carbonate in the reaction of carbon dioxide and epoxide is controlled, it is possible to provide a stable production without using an environmentally destructive substance and with excellent hygiene.

  Below, the manufacturing method of the polyalkylene carbonate in connection with this invention is demonstrated concretely.

  The epoxide that can be used in the present invention is preferably a monoepoxide, such as ethylene oxide, propylene oxide, 1-butene oxide, 2-butene oxide, isobutylene oxide, 1-pentene oxide, 2-pentene oxide, 1-hexene oxide, 1-octene oxide, 1-decene oxide, cyclopentene oxide, cyclohexene oxide, styrene oxide, vinylcyclohexene oxide, 3-phenylpropylene oxide, 3,3,3-trifluoropropylene oxide, 3-naphthylpropylene oxide, 3-phenoxypropylene Oxide, 3-naphthoxypropylene oxide, butadiene monoxide, 3-trimethylsilyloxypropylene oxide, methyl glycidyl carbonate, ethyl glycidyl Carbonates, such as can be displayed cholesterinase glycidyl carbonate, among others, ethylene oxide, propylene oxide, cyclohexene oxide. These may be used singly or in combination of two or more.

  As the catalyst used in the present invention, it is preferable to apply a catalyst containing zinc. The zinc-containing catalyst is roughly classified into a complex catalyst and a zinc oxide-aliphatic dicarboxylic acid reactant, and any of the catalyst systems can be applied. Hereinafter, a specific method for producing a zinc oxide-aliphatic dicarboxylic acid reactant will be described. explain.

  The zinc oxide may be produced in any way, for example, a method of thermally decomposing zinc oxalate to 400 ° C. or higher, a method of heating and dehydrating zinc hydroxycarbonate, a method of burning metallic zinc, or Zinc oxide produced by, for example, a method in which zinc ore is calcined with a reducing agent and the generated zinc vapor is oxidized with air can be used.

  Examples of the aliphatic dicarboxylic acid include oxalic acid, malonic acid, glutaric acid, adipic acid, 1,5-pentanedicarboxylic acid, 1,6-hexanedicarboxylic acid, 1,8-octanedicarboxylic acid, and 1,10-decanedicarboxylic acid. And dicarboxylic acids such as acids. Of these, glutaric acid and adipic acid are particularly preferred. These can also be used alone or in combination of two or more.

  An organic solvent can be allowed to coexist during the production of the catalyst. Examples of the organic solvent include aliphatic hydrocarbons such as pentane, hexane, heptane, octane, decane, and kerosene, aromatic hydrocarbons such as benzene, toluene, and xylene, phenols such as phenol, cresol, and xylenol, or ether derivatives thereof. Ethers such as diethyl ether, dibutyl ether, methyl butyl ether, ethylene glycol dimethyl ether, dioxane, dioxolane or alkyl or aryl derivatives thereof, alcohols such as methanol, ethanol, propanol, isobutanol, hexanol, ethylene glycol, diethylene glycol, glycerin or the like Its derivatives are methyl acetate, ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, ethyl butyrate. Esters, nitriles such as acetonitrile, propionitrile, butyronitrile and derivatives thereof, amines such as ethylenediamine, butylamine, aniline and derivatives thereof, amides such as N, N-dimethylformamide, etc. Even when used, it is effective in improving the pulverized state and improving the activity.

  However, the organic solvent is preferably a liquid at the pulverization temperature, and more preferably an organic solvent that can take in water produced by the reaction between zinc oxide and aliphatic dicarboxylic acid. Specifically, benzene, toluene, xylene, dioxane, tetrahydrofuran, oxetane, methanol, ethanol, propanol, isobutanol, ethyl acetate, butyl acetate, methyl propionate, acetonitrile, propionitrile, dimethylformamide and the like are preferable. Moreover, these organic solvents can also be used independently and can also be used in mixture of 2 or more types.

  Zinc sulfide can be added to the zinc oxide-aliphatic dicarboxylic acid reactant to improve the activity. Zinc sulfide may be produced by any method. For example, zinc sulfide produced by a method of adding ammonium sulfide to a zinc sulfate solution or a method of precipitating hydrogen sulfide into an acidic zinc salt solution is used. Can be used.

  The catalyst is synthesized by intimate contact and reaction by means of a mechanical grinding process. The mechanical pulverization process is performed using, for example, a ball mill, a vibration mill, an impact mill, a planetary ball mill, or the like. The charging ratio of zinc oxide and aliphatic dicarboxylic acid during pulverization is in the range of 0.1 to 10 mol, preferably 0.5 to 2 mol. In addition, when zinc sulfide is added, the charging ratio of zinc oxide and zinc sulfide at the time of pulverization is usually 0.001 to 0.1 mol of zinc sulfide, preferably 0.01 to 0, relative to 1 mol of zinc oxide. .05 mole range. When an organic solvent is added, the amount of the organic solvent to be added is 1 to 5000 parts by weight, preferably 5 to 1000 parts by weight, with respect to 100 parts by weight of the total weight of these zinc oxide and aliphatic dicarboxylic acid.

  It is preferable to select the pulverization conditions appropriately according to the type of raw material and the pulverizer, but if a rotary ball mill is taken as an example, a stainless steel ball 100 having a diameter of 15 mm and a ball inner cylinder having an inner volume of 800 mm and an inner diameter of 100 mm are used. When an individual is accommodated and the amount of an object to be processed is 20 to 40 g, the rotation speed is 125 rpm, usually 10 minutes to 30 days, preferably 20 minutes to 7 days. Taking a vibration mill and a planetary ball mill as an example, when a stainless steel ball of 2.8 kg is accommodated in a ball inner cylinder with a stainless steel inner capacity of 800 ml and an inner diameter of 100 mm, and the amount of workpiece is 20 to 40 g The impact acceleration is 2 to 15 G, and it is usually performed to the extent corresponding to the grinding treatment for 1 minute to 10 days, preferably 5 minutes to 4 days. Moreover, what is necessary is just to select grinding | pulverization temperature normally room temperature vicinity, and it is preferable to grind | pulverize at 0-150 degreeC.

  Using these catalysts, carbon dioxide and epoxies are polymerized in the presence of a carbonate solvent or an ether solvent to produce a polyalkylene carbonate. As the carbonate-based solvent or ether-based solvent, a solvent in which the polyalkylene carbonate to be produced is dissolved at 5% by weight or more at a temperature of 25 ° C. or more is preferable, more preferably 25 to 200 ° C., particularly preferably 25 to 150 ° C. % Or more is preferred. Examples of these include, for example, carbonate solvents such as dimethyl carbonate, methyl ethyl carbonate, diethyl carbonate, dipropyl carbonate, methyl propyl carbonate, and ethyl propyl carbonate that can dissolve polyalkylene carbonate, and ethers such as 1,3-dioxolane and dioxane. A solvent can be used. These solvents may be used alone or in combination of two or more. Further, a carbonate solvent or an ether solvent can be mixed and used in an aliphatic hydrocarbon solvent or an aromatic hydrocarbon solvent that is free from environmental health problems to a level at which the polyalkylene carbonate can be dissolved.

  In addition to having the ability to dissolve polyalkylene carbonate, the polymerization solvent can be used industrially as a solvent for environmental impact and hygiene, has no adverse effect on polymerization activity, and has no problem in removing the catalyst after polymerization. Etc. are required. The above-mentioned polymerization solvent satisfies these requirements, but further needs to be excellent in solvent separation from the polyalkylene carbonate. Solvent separation from polyalkylene carbonate can be achieved by flashing the polymerization solvent, evaporating to dryness, or by precipitating in a poor solvent such as hexane or methanol, and then evaporating the residual solvent in the precipitate and the poor solvent used. Do. Accordingly, since solvent removal by vaporization is required, a solvent having a relatively low boiling point is preferable. Among the above polymerization solvents, dimethyl carbonate, methyl ethyl carbonate, 1,3-dioxolane and dioxane are particularly preferable.

  In the above polymerization reaction, the molecular weight of the polymer to be produced can be controlled by adding a molecular weight control agent, that is, an organic compound having a trace amount of hydroxyl group or carboxylic acid group, or water. Examples of the organic compound having a hydroxyl group or a carboxylic acid group used here include aromatic carboxylic acids, aliphatic carboxylic acids, phenolic compounds, and alcoholic compounds. Specifically, as aromatic carboxylic acid, benzoic acid, o-toluic acid, m-toluic acid, p-toluic acid, phthalic acid, isophthalic acid, terephthalic acid, 1-naphthoic acid, 2-naphthoic acid, and fat Acetic acid, propionic acid, butyric acid, phenylacetic acid, trimethylacetic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, and phenolic compounds such as phenol, hydroquinone, resorcin, o-cresol, m -Cresol, p-cresol, 2,6-dimethylphenol, bisphenol A, and examples of alcohol compounds include benzyl alcohol and t-butanol. Moreover, these molecular weight control agents can also be used independently, and 2 or more types can also be mixed and used for them.

  The addition amount of the molecular weight control agent is preferably in the range of 0.05 to 20, particularly 0.10 to 10, in terms of molar ratio to Zn contained in the catalyst. If the amount added is too large, the reaction rate may decrease and productivity may decrease.

  The charge ratio of the solvent and the epoxide is usually in the range of 10:90 to 99: 1, particularly 20:80 to 90:10 in terms of volume ratio. The pressure of the carbon dioxide gas is not particularly limited, but the polymerization is preferably performed at a pressure of 0.1 to 20 MPa, preferably 0.2 to 10 MPa, more preferably 0.5 to 5 MPa. The polymerization temperature is usually 0 to 200 ° C, preferably 50 to 150 ° C. By increasing the polymerization time, it is possible to increase the polymer yield. The polymerization time is not particularly limited, but the polymerization is usually carried out in the range of 10 minutes to 240 hours, preferably 30 minutes to 80 hours, more preferably 1 to 10 hours. The order of addition of the polymerization solvent, epoxide, carbon dioxide gas and catalyst is not particularly limited. The polymerization can be carried out by any of batch, semi-continuous and continuous methods, and the polymerization can be carried out in two or more stages having different reaction conditions.

  After completion of the polymerization reaction, the catalyst residue can be removed by filtration or by washing with a dilute acid aqueous solution, dilute alkali aqueous solution or the like.

  EXAMPLES Hereinafter, although an Example demonstrates this invention, Of course, this invention is not limited to this Example.

<Example 1>
Catalyst preparation Commercially available 10.4 g of zinc oxide, 16.3 g of glutaric acid, 0.25 g of zinc sulfide, and 23.1 g of dioxane, containing 30 stainless steel balls with a diameter of 15.8 mm and 30 stainless steel balls with a diameter of 19 mm. The sample was placed in an inner cylinder of a stainless steel ball mill having an inner volume of 500 ml and contacted with a planetary ball mill at an acceleration of 3.5 G for 9 hours. The obtained contact-treated product was dried under reduced pressure at 150 ° C. for 3 hours to obtain a zinc-containing catalyst.

In an autoclave having a polymerization internal volume of 0.3 liter, 89 g of dimethyl carbonate, 0.24 g of the zinc-containing catalyst, and 23 g of ethylene oxide were charged, and carbon dioxide was added at room temperature to a pressure of 1.5 MPa. Then, it heated up to 80 degreeC and superposed | polymerized for 2 hours. Immediately after the temperature increase, the pressure increased to 2.7 MPa, but carbon dioxide was consumed with the reaction and the pressure decreased. After completion of the polymerization, the autoclave was cooled and then depressurized to take out the polymerization solution. The polymerization solution was in a state where the polymer was completely dissolved. The taken-out polymer solution was filtered with a filter having a pore size of 1 micron to remove the solid zinc-containing catalyst, and the filtrate was dried to obtain a polymer. The polymer yield was 14.3 g and the catalytic activity was 58.7 g / g-cat. The weight average molecular weight analyzed by GPC was 260,000. Further, the residual zinc concentration in the polymer obtained by drying after filtration was 28 ppm.

<Example 2>
In Example 1, polymerization was carried out in the same manner as in Example 1 except that 1,3-dioxolane was used instead of dimethyl carbonate for the polymerization, and the catalyst obtained in Example 1 was used. After polymerization, the taken out polymerization solution was in a state in which the polymer was completely dissolved. The taken-out polymer solution was filtered with a filter having a pore size of 1 micron to remove the solid zinc-containing catalyst, and the filtrate was dried to obtain a polymer. The polymer yield was 19.2 g and the catalyst activity was 79.1 g / g-cat. The weight average molecular weight analyzed by GPC was 350,000. Moreover, the residual zinc concentration in the polymer obtained by drying after filtration was 30 ppm.

<Comparative Example 1>
In Example 1, polymerization was carried out in the same manner as in Example 1 except that n-hexane was used instead of dimethyl carbonate for the polymerization, and the catalyst obtained in Example 1 was used. After the polymerization, the polymer solution taken out had white and amorphous polymer deposited. Filtration was performed through a wire mesh having a 1 mm pore diameter to separate the polymer mass from the mother liquor, and the polymer mass was dried. The polymer yield was 12.3 g and the catalytic activity was 48.3 g / g-cat. The weight average molecular weight analyzed by GPC was 510,000. The residual zinc concentration in the polymer obtained by drying after filtration was 3300 ppm.

<Example 3>
In Example 2, polymerization was performed in the same manner as in Example 2 except that 0.10 g of benzoic acid was added as a molecular weight control agent to the solvent. After the polymerization, the removed polymer solution was filtered through a filter having a pore size of 1 micron to remove the solid zinc-containing catalyst, and the filtrate was dried to obtain a polymer. The polymer yield was 11.5 g and the catalytic activity was 44.8 g / g-cat. The weight average molecular weight analyzed by GPC was 64,000. The residual zinc concentration in the polymer obtained by drying after filtration was 4 ppm.

<Example 4>
In Example 3, polymerization was performed in the same manner as in Example 3 except that the reaction time was 6 hours. After the polymerization, the removed polymer solution was filtered through a filter having a pore size of 1 micron to remove the solid zinc-containing catalyst, and the filtrate was dried to obtain a polymer. The polymer yield was 16.6 g and the catalyst activity was 65.6 g / g-cat. The weight average molecular weight analyzed by GPC was 70,000. Moreover, the residual zinc concentration in the polymer obtained by drying after filtration was 6 ppm.

<Example 5>
In Example 2, polymerization was performed in the same manner as in Example 2 except that 0.015 g of water was added as a molecular weight control agent to the solvent. After the polymerization, the removed polymer solution was filtered through a filter having a pore size of 1 micron to remove the solid zinc-containing catalyst, and the filtrate was dried to obtain a polymer. The polymer yield was 12.4 g and the catalyst activity was 48.6 g / g-cat. The weight average molecular weight analyzed by GPC was 28,000. The residual zinc concentration in the polymer obtained by drying after filtration was 4 ppm.

<Example 6>
In Example 2, polymerization was performed in the same manner as in Example 2 except that 0.11 g of glutaric acid was added as a molecular weight control agent to the solvent. After the polymerization, the removed polymer solution was filtered through a filter having a pore size of 1 micron to remove the solid zinc-containing catalyst, and the filtrate was dried to obtain a polymer. The polymer yield was 11.4 g and the catalytic activity was 44.8 g / g-cat. The weight average molecular weight analyzed by GPC was 38,000. Moreover, the residual zinc concentration in the polymer obtained by drying after filtration was 7 ppm.

<Example 7>
In Example 2, polymerization was performed in the same manner as in Example 2 except that 0.059 g of o-cresol was added as a molecular weight control agent to the solvent. After the polymerization, the removed polymer solution was filtered through a filter having a pore size of 1 micron to remove the solid zinc-containing catalyst, and the filtrate was dried to obtain a polymer. The polymer yield was 20.8 g and the catalytic activity was 75.9 g / g-cat. The weight average molecular weight analyzed by GPC was 87,000. The residual zinc concentration in the polymer obtained by drying after filtration was 5 ppm.

<Example 8>
In Example 2, polymerization was performed in the same manner as in Example 2 except that 0.083 g of trimethylacetic acid was added as a molecular weight control agent to the solvent. After the polymerization, the removed polymer solution was filtered through a filter having a pore size of 1 micron to remove the solid zinc-containing catalyst, and the filtrate was dried to obtain a polymer. The polymer yield was 10.7 g and the catalyst activity was 40.2 g / g-cat. The weight average molecular weight analyzed by GPC was 29,000. The residual zinc concentration in the polymer obtained by drying after filtration was 4 ppm.

<Example 9>
In Example 2, polymerization was performed in the same manner as in Example 2 except that 0.11 g of benzyl alcohol was added as a molecular weight control agent to the solvent. After the polymerization, the removed polymer solution was filtered through a filter having a pore size of 1 micron to remove the solid zinc-containing catalyst, and the filtrate was dried to obtain a polymer. The polymer yield was 27.7 g and the catalytic activity was 109.8 g / g-cat. The weight average molecular weight analyzed by GPC was 66,000. Moreover, the residual zinc concentration in the polymer obtained by drying after filtration was 7 ppm.

<Example 10>
In Example 8, polymerization was performed in the same manner as in Example 8 except that the amount of benzyl alcohol added was increased to 0.18 g. After the polymerization, the removed polymer solution was filtered through a filter having a pore size of 1 micron to remove the solid zinc-containing catalyst, and the filtrate was dried to obtain a polymer. The polymer yield was 27.7 g and the catalyst activity was 105.4 g / g-cat. The weight average molecular weight analyzed by GPC was 45,000. The residual zinc concentration in the polymer obtained by drying after filtration was 4 ppm.

<Example 11>
In Example 8, polymerization was performed in the same manner as in Example 8 except that the amount of benzyl alcohol added was increased to 0.40 g. After the polymerization, the removed polymer solution was filtered through a filter having a pore size of 1 micron to remove the solid zinc-containing catalyst, and the filtrate was dried to obtain a polymer. The polymer yield was 28.6 g and the catalytic activity was 113.2 g / g-cat. The weight average molecular weight analyzed by GPC was 21,000. Moreover, the residual zinc concentration in the polymer obtained by drying after filtration was 6 ppm.

Claims (7)

A method for producing a polyalkylene carbonate, which comprises using a carbonate solvent or an ether solvent in solution copolymerization of carbon dioxide and epoxide in the presence of an organic compound having a hydroxyl group or a carboxylic acid group, or water. The method for producing a polyalkylene carbonate according to claim 1, wherein a zinc-containing catalyst is used in the reaction of carbon dioxide and epoxide. The method for producing a polyalkylene carbonate according to claim 2, wherein the zinc-containing catalyst is a zinc-containing solid catalyst obtained by bringing zinc oxide and an aliphatic dicarboxylic acid into contact with each other by a mechanical pulverization means. The method for producing a polyalkylene carbonate according to claim 1, wherein the carbonate solvent or ether solvent is a solvent for dissolving 5% by weight or more of the produced polyalkylene carbonate at a temperature of 25 ° C or higher. The method for producing a polyalkylene carbonate according to claim 4, wherein the carbonate solvent is at least one of dimethyl carbonate and methyl ethyl carbonate. The process for producing a polyalkylene carbonate according to claim 4, wherein the ether solvent is at least one of 1,3-dioxolane and dioxane. 2. The method for producing a polyalkylene carbonate according to claim 1, wherein the organic compound having a hydroxyl group or a carboxylic acid group is an aromatic carboxylic acid, an aliphatic carboxylic acid, a phenol compound, or an alcohol compound.