TW201504269A - Method of separating aliphatic polycarbonate polymer and catalyst from preparing process of copolymer - Google Patents

Abstract

Provided is a method of separating a catalyst from a solution containing a copolymer and the catalyst dissolved therein, after a polymerization reaction is performed using the catalyst, and more specifically, selection and utilization of an adsorbent used for separation.

Description

Method for separating aliphatic copolycarbonate copolymer and catalyst from copolymer production method

The present invention relates to a method for separating an aliphatic polycarbonate polymer and a catalyst from a method for preparing a copolymer; more specifically, a method for copolymerizing carbon dioxide and an epoxy compound (epoxide) from the presence of a catalyst. In the reaction mixture obtained by the compound, a method of separating an aliphatic polycarbonate polymer and a catalyst, the catalyst being a complex containing an onium salt.

The method of copolymerizing an epoxide and carbon dioxide to prepare a polycarbonate using a complex containing a phosphonium salt as a catalyst has been disclosed in Korean Patent No. 10-0853358 and No. 10-0981270, the same as the present invention. And a method of separately collecting and regenerating a catalyst as a product in a mixed solution of a self-catalyst and a copolymer.

There is a case where the metal catalyst used for the polymerization of the polymer is not separated from the final product, such as the Ziegler Natta catalyst; however, this is very rare and, for the following reasons, The media should have to be removed or collected.

In the final step of preparing a polycarbonate by copolymerization of an epoxy compound with carbon dioxide using a complex containing a phosphonium salt as a catalyst, the catalyst system Arranged on the terminal groups of the long polymer with direct chemical bonding to the polymer chain. In the absence of separation of the catalyst, the polymer polymer decomposes into carbon dioxide and cyclic propylene carbonate (CPC) over time, resulting in a decrease in the molecular weight of the copolymer and deterioration of all physical properties. , thus reducing the value of the product.

In addition, if the ligand containing the chromophore and the transition metal complex salt is not completely removed from the product, the final product will have a color, so there will be problems in quality and commercial value, and Due to the toxicity of transition metals, the application of polymers is also limited.

In particular, in the copolymerization catalyst of the carbon dioxide/epoxy compound which is the target of the present invention, since the metal itself is expensive and the catalyst contains many high-priced ligands, in order to ensure economic efficiency, it is necessary to remove and collect the use. Catalyst.

In order to separate or remove the catalyst used in the polymerization of the polymer, alumina, tannin, ion exchange resin, etc. are usually used (see "Prog. Polym. Sci. 2004, 29, 1053"), and the use is drastically used. A method of removing a catalyst by direct action of a catalyst with a functional group present on the surface of an absorbent, such as -OH, -SH. However, in general, tantalum rubber and alumina have a low catalyst removal rate, and therefore must be used in a large amount to sufficiently remove the catalyst, so that material cost and preparation cost (solution use, loss of pressure, etc.) and the like are increased.

Therefore, there is a need for an efficient and economical process for obtaining high purity aliphatic polycarbonate polymers from the preparation of copolymers and for separating and removing catalysts and reaction by-products.

[Previous Technical Literature]

[Patent Document]

(Patent 1) Korean Patent No. 10-0853358

(Patent 2) Korean Patent No. 10-0981270

[Non-patent literature]

(Non-patent 1) Prog. Polym. Sci. 2004, 29, 1053

An object of the present invention is to provide a high purity aliphatic polycarbonate polymer which can be obtained from a reaction mixture obtained by using a complex containing a cerium salt as a catalyst to prepare a copolymer. A method of efficiently separating and removing residual catalyst and by-products.

The present invention provides a more efficient and economical separation and removal of catalysts in a reaction mixture from the polymerization of an aliphatic polycarbonate polymer carried out in the presence of a ruthenium-containing complex catalyst. And by-products to obtain a high purity aliphatic polycarbonate polymer.

In one aspect, the present invention provides a method of separating an aliphatic polycarbonate polymer and a catalyst, wherein the aliphatic polycarbonate polymer and the catalyst are polymerized in an aliphatic polycarbonate in the presence of a catalyst. In the reaction mixture of the reaction, the catalyst contains a complex of a phosphonium salt, and the method uses two solvents which are not mixed with each other in the reaction mixture.

The two solvents which are not mixed with each other may be an organic solvent and an aqueous solution.

The method can include: a) polymerizing carbon dioxide and an epoxide compound in the presence of the ruthenium salt-containing complex catalyst; b) adding the two solvents which are not mixed with each other to the reaction mixture of step a), and An extraction step is performed to separate the organic layer and the aqueous layer; c) an aliphatic polycarbonate is obtained from the separated organic layer; and d) the catalyst is collected from the separated aqueous layer.

The organic solvent may be at least one selected from the group consisting of toluene, benzene, xylene, tetrahydrofuran, dichloromethane, dichloroethane, ethyl acetate, propyl acetate, isopropyl acetate, and butyl acetate, and The aqueous solution may contain from 0.1% by weight to 10% by weight of the inorganic salt.

The epoxy compound may be at least one selected from the group consisting of: or without halogen, (C1 to C20) alkoxy, (C6 to C20) aryloxy, or (C6 to C20) aryl (C1 to C20) alkyl (aralkyl)oxy ((C6-C20)ar(C1-C20)alkyl(aralkyl)oxy) substituted (C2 to C20) alkylene oxide; Halogen, (C1 to C20) alkoxy, (C6 to C20) aryloxy, or (C6 to C20) aryl (C1 to C20) alkyl (aralkyl)oxy substituted (C4 to C20) ring Cycloalkylene oxide; and with or without halogen, (C1 to C20) alkoxy, (C6 to C20) aryloxy, (C6 to C20) aryl (C1 to C20) alkyl (aralkyl (C8 to C20) styrene substituted by (oxy) or (C1 to C20) alkyl. The aliphatic polycarbonate polymer may be polypropylene carbonate, polyethylene carbonate, polycyclohexene carbonate, polybutylene carbonate, poly Cyclopentene Polycyclopentene carbonate, polycyclooctene carbonate.

The complex salt containing a phosphonium salt can have the following chemical formula 1:

In the above Chemical Formula 1, M is a trivalent cobalt or a trivalent chromium; A is an oxygen atom or a sulfur atom; Q is a diradical connecting a diazo atom; R ¹ to R ¹⁰ are each independently hydrogen; halogen; (C1 To C20)alkyl; (C1 to C20) alkyl containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C2 to C20) alkenyl; containing halogen, nitrogen, oxygen, hydrazine, (C2 to C20) alkenyl group of one or more of sulfur and phosphorus; (C1 to C20) alkyl (C6 to C20) aryl; containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus (C1 to C20) alkyl (C6 to C20) aryl; (C6 to C20) aryl (C1 to C20) alkyl; containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus (C6 to C20) aryl (C1 to C20) alkyl; (C1 to C20) alkoxy; (C6 to C30) aryloxy; formazan; (C1 to C20) alkylcarbonyl ((C1-C20) An alkylcarbonyl); or a (C6 to C20) arylcarbonyl group ((C6-C20) arylcarbonyl); or a metal radical such as a Group 14 metal substituted with a (C1 to C20) alkyl group or a (C6 to C20) aryl group; Two of R ¹ to R ¹⁰ may be bonded to each other to form a ring; at least one of the hydrogens included in R ¹ to R ¹⁰ and Q is selected from the following chemical formulas a, b, And a proton group of the group consisting of c;

X ^- each independently is a halogen anion; HCO ₃ ^- ; BF ₄ ^- ; ClO ₄ ^- ; NO ₃ ^- ; PF ₆ ^- ; (C6 to C20) aryloxy anion; contains a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom a (C6 to C20) aryloxy anion of one or more of a sulfur atom and a phosphorus atom; (C1 to C20) an alkylcarboxy anion; containing a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and (C1 to C20) alkylcarboxy anion of one or more of phosphorus atoms; (C6 to C20) arylcarboxy anion; containing one of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom or a plurality of (C6 to C20) arylcarboxy anions; (C1 to C20) alkoxy anions; containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom (C1) To a C20) alkoxy anion; (C1 to C20) alkyl carbonate anion; (C1-C20) alkylcarbonate anion; containing one of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom or (C1 to C20) alkyl carbonate anion; (C6 to C20) aryl carbonate anion ((C6-C20) arylcarbon (ate anion); (C6 to C20) aryl carbonate anion containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom; (C1 to C20) alkylsulfonate anion ((C1-C20)alkylsulfonate anion); (C1 to C20) alkylsulfonate anion containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom; (C1 to C20 An alkylguanamine anion; a (C1 to C20) alkylguanamine anion containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom; (C6 to C20) An arylguanidinium anion; an (C6 to C20) arylguanamine anion containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom; (C1 to C20) (C1-C20)alkylcarbamate anion; (C1 to C20) alkylamine formic acid containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom Anion; (C6 to C20) an arylamine anion; or a halogen atom, a nitrogen atom, an oxygen atom, (C6 to C20) aryl amine formate anions atom, a sulfur atom, a phosphorus atom and one or more of; the Z containing nitrogen or phosphorus ^{atom; R 21, R 22, R} 23, R 31, R 32, R ³³ , R ³⁴ and R ³⁵ are each independently (C1 to C20) alkyl; (C1 to C20) alkyl containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C2 to C20) Alkenyl; (C2 to C20) alkenyl group containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C1 to C20) alkyl (C6 to C20) aryl; containing halogen, nitrogen (C1 to C20) alkyl (C6 to C20) aryl group of one or more of oxygen, hydrazine, sulfur, and phosphorus; (C6 to C20) aryl (C1 to C20) alkyl; containing halogen, nitrogen, (C6 to C20) aryl (C1 to C20) alkyl of one or more of oxygen, hydrazine, sulfur, and phosphorus; or 14th substituted by (C1 to C20) alkyl or (C6 to C20) aryl a metal radical such as a metal group; two of R ²¹ , R ²² and R ²³ , or two of R ³¹ , R ³² , R ³³ , R ³⁴ and R ³⁵ , may be bonded to each other to form a ring; R ⁴¹ , R ⁴² and R ⁴³ are each independently hydrogen; (C1 to C20) alkyl; containing one or more of halogen, nitrogen, oxygen, helium, sulfur, and phosphorus (C1 to C20) alkyl; (C2 to C20) alkenyl; (C2 to C20) alkenyl containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C1 to C20) Alkyl (C6 to C20) aryl; (C1 to C20) alkyl (C6 to C20) aryl containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C6 to C20) aryl a (C1 to C20) alkyl group; (C6 to C20) aryl (C1 to C20) alkyl group containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; or (C1 to C20) a metal radical such as an alkyl group or a (C6 to C20) aryl group substituted with a Group 14 metal; R ⁴¹ , R ⁴² , and R ⁴³ may be bonded to each other to form a ring; X'-based oxygen atom, sulfur atom Or NR, wherein R is a (C1 to C20) alkyl group; n is an integer obtained by adding 1 to the total number of proton groups included in R ¹ to R ¹⁰ and Q; X ^- can be coordinated to M; and imine A nitrogen atom can coordinate or decoordinate with M.

In another aspect, the present invention provides an aliphatic polycarbonate in a reaction mixture of an aliphatic polycarbonate polymerized in the presence of a catalyst. An ester polymer and a catalyst, a device for separating from the reaction mixture, the catalyst comprising a complex of a phosphonium salt, the apparatus comprising: a reactor 100 for performing a complex complex with the cerium-containing salt Polymer-catalyzed polymerization of aliphatic polycarbonate; a phase separator 200 by adding two solvents which are not mixed with each other to a reaction mixture obtained by polymerization of the reactor, and performing an extraction treatment Separating the organic layer and the aqueous layer; a refiner 300 for obtaining the aliphatic polycarbonate from the organic layer separated by the phase separator; and a catalyst collector (not shown) for The catalyst is collected from the aqueous layer separated by the phase separator.

According to the method of the present invention, two kinds of mutually incompatible solvents are used in the reaction mixture of the polymerization of the aliphatic polycarbonate polymer in the presence of a ruthenium-containing complex catalyst to remove the polymerization reaction. The resulting cyclic carbonate by-product is obtained to obtain a high purity aliphatic polycarbonate and the catalyst used in the reaction is easily removed.

Further, the method of the present invention uses two immiscible solvents to remove the catalyst in the reaction mixture of the polymerization of the aliphatic polycarbonate polymer in the presence of a ruthenium-containing complex catalyst. The use of existing silicone or resin to remove the catalyst does not result in a back biting phenomenon of the previously prepared aliphatic polycarbonate, so that a cyclic carbonate may not be formed and during polymerization. The resulting cyclic carbonate can be removed.

In addition, the method of the present invention removes the catalyst by a simple procedure (using two kinds of solvents which are not mixed with each other instead of using existing silicone, resin, etc.) to increase the removal rate of the catalyst and by-products, and the effect is equivalent. Significant. Furthermore, the method is significantly economical since no other equipment is required.

Further, by the method of the present invention, the removal rate of the cyclic carbonate formed during the polymerization reaction in which the catalyst participates is high, and the bite phenomenon of the aliphatic polycarbonate polymer does not occur, and high can be obtained. A purity of the aliphatic polycarbonate polymer to enhance the quality of the product containing it.

The above and other objects, features and advantages of the present invention will become apparent from the accompanying drawings.

100‧‧‧reactor

200‧‧‧ phase separator

300‧‧‧Refiner

410‧‧‧First pump

420‧‧‧Second pump

430‧‧‧ third pump

440‧‧‧fourth pump

510‧‧‧Organic solvent discharge section

520‧‧‧Polycarbonate discharge

BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 is a schematic view showing a method of separating an aliphatic polycarbonate polymer and a catalyst from a reaction mixture of an aliphatic polycarbonate polymerization according to an exemplary embodiment of the present invention.

[best mode]

The present invention provides a method for separating an aliphatic polycarbonate polymer and a catalyst, wherein the aliphatic polycarbonate polymer and the catalyst are in a reaction mixture of an aliphatic polycarbonate polymerization carried out in the presence of a catalyst, The catalyst is a complex containing a phosphonium salt in which two solvents which are not mixed with each other are used in the reaction mixture.

The process according to the invention is simple and effective, which removes the catalyst used in the reaction and the cyclic carbonate formed during the polymerization to obtain a high purity aliphatic polycarbonate polymer.

Furthermore, the process of the present invention does not require existing separation methods or separation equipment required for materials such as adsorbents, which are significantly economical and have high removal rates for cyclic carbonates, which are When the polymerization reaction with a catalyst proceeds, the purity of the aliphatic polycarbonate polymer is deteriorated.

Further, the bite phenomenon of the aliphatic polycarbonate polymer produced by the separation using the existing silicone rubber, resin, etc., does not occur here, that is, no cyclic carbonate is formed here, so that An aliphatic polycarbonate polymer having high purity is obtained in high yield.

The reaction mixture is an object of the present invention, which may be a catalyst copolymerization using an epoxide and a carbon dioxide in the method described in Korean Patent Application Laid-Open No. 10-2009-0090154, and then the remaining carbon dioxide and epoxy a solution obtained in a state where the compound is not removed; a solution obtained in a state where only carbon dioxide is removed after the polymerization reaction; or a carbon dioxide and an epoxide are removed after the polymerization reaction, and the other is added again The solution obtained in the state where the solvent is used for subsequent treatment.

According to an exemplary embodiment of the present invention, the two solvents which are not mixed with each other may be an organic solvent and an aqueous solution.

According to an exemplary embodiment of the present invention, an aliphatic polycarbonate polymer and a catalyst in a reaction mixture of an aliphatic polycarbonate polymerization carried out in the presence of a ruthenium-containing complex catalyst are used. The method for separating from the reaction mixture comprises: a) polymerizing carbon dioxide and an epoxy compound in the presence of a complex catalyst containing a phosphonium salt; b) adding two solvents which are not mixed with each other to the reaction mixture of step a), and performing an extraction treatment to separate the organic layer and the aqueous layer; c) obtaining an aliphatic polycarbonate from the separated organic layer; And d) collecting the catalyst from the separated aqueous layer.

According to an exemplary embodiment of the present invention, the organic solvent may be at least one selected from the group consisting of toluene, benzene, xylene, tetrahydrofuran, dichloromethane, dichloroethane, ethyl acetate, propyl acetate, Isopropyl acetate and butyl acetate, and in terms of more efficient separation, the organic solvent may be toluene, tetrahydrofuran or a mixed solvent thereof.

According to an exemplary embodiment of the present invention, the aqueous solution may contain 0.1% by weight to 20% by weight of an inorganic salt, preferably 0.1% by weight to 10% by weight, more preferably 0.8% by weight to 10% by weight, and more preferably Effective removal of catalyst and cyclic carbonate.

According to an exemplary embodiment of the present invention, the inorganic salt may be any inorganic salt as long as the salt is generally used; however, the inorganic salt may be added in terms of increasing the removal rate of the catalyst and reaction by-products. It is sodium chloride, ammonium chloride, sodium hydrogencarbonate, or a mixture of the foregoing.

According to an exemplary embodiment of the present invention, the extraction treatment of step b), that is, the extraction treatment in the separation of the organic layer and the aqueous layer, includes the addition of two solvents which are not mixed with each other to the reaction of the step a) The mixture may be subjected to one or more extractions, preferably three or more times, to increase the high purity aliphatic polycarbonate and to increase the removal rate of the catalyst and by-products.

More preferably, in order to increase the purity of the high-purity aliphatic polycarbonate polymer and to increase the removal of the catalyst and by-products, the organic solvent may be toluene or tetrahydrofuran. Or a mixed solvent thereof, and the aqueous solution may contain 0.8% by weight to 10% by weight of an inorganic salt.

According to an exemplary embodiment of the present invention, the aliphatic polycarbonate polymer is a polycarbonate obtained by polymerizing carbon dioxide and an epoxy compound described below, which may be a polypropylene carbonate or a polyethylene carbonate. Polycyclohexene carbonate, polybutylene carbonate or polycyclopentene carbonate, preferably polypropylene carbonate, polyvinyl carbonate or polybutylene carbonate.

According to an exemplary embodiment of the present invention, the epoxy compound may be at least one selected from the group consisting of: or without halogen, (C1 to C20) alkoxy, (C6 to C20) aryloxy Or (C6 to C20) aryl (C1 to C20) alkyl (aralkyl)oxy substituted (C2 to C20) alkylene oxide; with or without halogen, (C1 to C20) alkoxy, (C6 to C20) aryloxy, or (C6 to C20) aryl (C1 to C20) alkyl (aralkyl)oxy substituted (C4 to C20) cycloalkylene oxide; and with or without halogen , (C1 to C20) alkoxy, (C6 to C20) aryloxy, (C6 to C20) aryl (C1 to C20) alkyl (aralkyl)oxy, or (C1 to C20) alkyl substituted (C8 to C20) styrene oxide.

The complex salt containing a phosphonium salt can have the following chemical formula 1:

In the above Chemical Formula 1, M is a trivalent cobalt or a trivalent chromium; A is an oxygen atom or a sulfur atom; Q is a diradical connecting a diazo atom; R ¹ to R ¹⁰ are each independently hydrogen; halogen; (C1 To C20)alkyl; (C1 to C20) alkyl containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C2 to C20) alkenyl; containing halogen, nitrogen, oxygen, hydrazine, (C2 to C20) alkenyl group of one or more of sulfur and phosphorus; (C1 to C20) alkyl (C6 to C20) aryl; containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus (C1 to C20) alkyl (C6 to C20) aryl; (C6 to C20) aryl (C1 to C20) alkyl; containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus (C6 to C20) aryl (C1 to C20) alkyl; (C1 to C20) alkoxy; (C6 to C30) aryloxy; formazan; (C1 to C20) alkylcarbonyl ((C1-C20) An alkylcarbonyl); or a (C6 to C20) arylcarbonyl group ((C6-C20) arylcarbonyl); or a metal radical such as a Group 14 metal substituted with a (C1 to C20) alkyl group or a (C6 to C20) aryl group; Two of R ¹ to R ¹⁰ may be bonded to each other to form a ring; at least one hydrogen group included in R ¹ to R ¹⁰ and Q is selected from the following chemical formulas a, b And proton groups of the group consisting of c;

X ^- each independently is a halogen anion; HCO ₃ ^- ; BF ₄ ^- ; ClO ₄ ^- ; NO ₃ ^- ; PF ₆ ^- ; (C6 to C20) aryloxy anion; contains a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom a (C6 to C20) aryloxy anion of one or more of a sulfur atom and a phosphorus atom; (C1 to C20) an alkylcarboxy anion; containing a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and (C1 to C20) alkylcarboxy anion of one or more of phosphorus atoms; (C6 to C20) arylcarboxy anion; containing one of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom or a plurality of (C6 to C20) arylcarboxy anions; (C1 to C20) alkoxy anions; containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom (C1) To a C20) alkoxy anion; (C1 to C20) alkyl carbonate anion; (C1 to C20) alkane containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom Carbonate anion; (C6 to C20) aryl carbonate anion; containing a halogen atom, a nitrogen atom, an oxygen atom, (C6 to C20) aryl carbonate anion of one or more of an atom, a sulfur atom, and a phosphorus atom; (C1 to C20) alkyl sulfonate anion; containing a halogen atom, a nitrogen atom, an oxygen atom, a ruthenium atom, sulfur (C1 to C20) alkyl sulfonate anion of one or more of atoms and phosphorus atoms; (C1 to C20) alkyl guanyl anion; containing a halogen atom, a nitrogen atom, an oxygen atom, a ruthenium atom, a sulfur atom, And (C1 to C20)alkylguanamine anion of one or more of phosphorus atoms; (C6 to C20) arylguanamine anion; containing a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a (C6 to C20) arylguanamine anion of one or more of phosphorus atoms; (C1 to C20) alkylamine formate; containing a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a (C1 to C20) alkylamine formate anion of one or more of the phosphorus atoms; (C6 to C20) an arylamine formate; or a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and (C6 to C20) arylamine anion anion of one or more of phosphorus atoms; Z-based nitrogen atom or phosphorus atom ^{R 21, R 22, R 23} , R 31, R 32, R 33, R 34, and R ³⁵ are each independently (C1 to C20) alkyl; contain halogen, nitrogen, oxygen, silicon, sulfur, phosphorus, and one Or a (C1 to C20) alkyl group; (C2 to C20) alkenyl; (C2 to C20) alkenyl group containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; C20) alkyl (C6 to C20) aryl; (C1 to C20) alkyl (C6 to C20) aryl group containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C6 to C20) An aryl (C1 to C20) alkyl group; a (C6 to C20) aryl (C1 to C20) alkyl group containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; a C20) alkyl or a (C6 to C20) aryl substituted metal radical such as a Group 14 metal; R ²¹ , R ²² and R ²³ , or R ³¹ , R ³² , R ³³ , R ³⁴ , And R ³⁵ may be bonded to each other to form a ring; R ⁴¹ , R ⁴² , and R ⁴³ are each independently hydrogen; (C1 to C20) alkyl; containing halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus One or more (C1 to C20) alkyl groups; (C2 to C20) alkenyl groups; containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus (C2 to C2) 0) alkenyl; (C1 to C20) alkyl (C6 to C20) aryl; (C1 to C20) alkyl (C6 to C20) containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus Aryl; (C6 to C20) aryl (C1 to C20) alkyl; (C6 to C20) aryl (C1 to C20) containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus An alkyl group; or a metal radical such as a Group 14 metal substituted with a (C1 to C20) alkyl group or a (C6 to C20) aryl group; two of R ⁴¹ , R ⁴² , and R ⁴³ may be bonded to each other to form a ring; X' is an oxygen atom, a sulfur atom or NR, wherein R is a (C1 to C20) alkyl group; n is an integer obtained by adding 1 to the total number of proton groups included in R ¹ to R ¹⁰ and Q; X ^- Coordination with M; and one of the imine nitrogen atoms can coordinate or decoordinate with M.

Preferably, in the above chemical formula 1 containing a phosphonium salt of the present invention, M is a trivalent cobalt; an A-based oxygen atom; and a Q-system trans-1, 2-transhexyl (trans-1, 2-cyclohexylene), a phenyl or ethyl group; R ¹ and R ² are the same or different first-order (C1 to C20) alkyl groups; R ³ to R ¹⁰ are each independently hydrogen or -[YR ⁵¹ _3-a (CR ⁵² R ⁵³ ) _b N ⁺ R ⁵⁴ R ⁵⁵ R ⁵⁶ _a ]; Y system C or Si; R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ , R ⁵⁵ and R ⁵⁶ are each independently hydrogen; halogen; (C1 to C20) alkyl; a (C1 to C20) alkyl group containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C2 to C20) alkenyl; containing one of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus Or more (C2 to C20) alkenyl; (C1 to C20) alkyl (C6 to C20) aryl; containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus (C1 to C20) Alkyl (C6 to C20) aryl; (C6 to C20) aryl (C1 to C20) alkyl; containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus (C6 to C20) Aryl (C1 to C20) alkyl; (C1 to C20) alkoxy; (C6 to C30) aryloxy; indolyl; (C1 to C20) alkylcarbonyl; (C6 to C20) arylcarbonyl; Hydrocarbyl substituted Group 14 metals metal radical ;; R ^54, R ⁵⁵ and R ⁵⁶ in the both may be connected each other to form a ring; a system integer of 1 to 3, b and integer of from 1 to 20 lines; or n-4-based a larger integer, obtained by adding 1 to the total number of quaternary amine salts included in R ³ to R ¹⁰ ; and when a is a system 1, at least three of R ³ to R ¹⁰ may be -[YR ⁵¹ _{3- a} (CR ⁵² R ⁵³ ) _b N ⁺ R ⁵⁴ R ⁵⁵ R ⁵⁶ _a ], when a is 2, at least two of R ³ to R ¹⁰ may be -[YR ⁵¹ _3-a (CR ⁵² R ⁵³ ) _b N ⁺ R ⁵⁴ R ⁵⁵ R ⁵⁶ _a ], when a is 3, at least one of R ³ to R ¹⁰ may be -[YR ⁵¹ _3-a (CR ⁵² R ⁵³ ) _b N ⁺ R ⁵⁴ R ⁵⁵ R ⁵⁶ _a ].

More preferably, the above Chemical Formula 1 may be a complex having the following Chemical Formula 2:

In the above Chemical Formula 2, R ⁶¹ and R ⁶² are each independently a methyl group or an ethyl group; X ^- each independently is a nitrogen or acetate anion; the nitrogen of the imine may coordinate or decoordinate with the cobalt, and each anion may be combined with Cobalt coordination.

In addition, the present invention also provides an aliphatic polycarbonate polymer containing 2% by weight to 7% by weight, preferably 2% by weight to 5% by weight, based on the obtained aliphatic polycarbonate polymer, of a cyclic carbonate.

Further, according to the method of the present invention, the present invention also provides an aliphatic polycarbonate polymer containing 10 ppm or less, preferably 5 ppm, more preferably 2 ppm or less of a metal catalyst.

In order to effectively separate the method according to an exemplary embodiment of the present invention, in the complex catalyst represented by the above Chemical Formula 1, it is preferred that M is a trivalent cobalt; an A-based oxygen atom; and a Q system. Trans-1,2-cyclohexylene, phenyl or ethyl; R ¹ and R ² are the same or different first-order (C1 to C20) alkyl; R ³ to R ¹⁰ are each independently hydrogen or -[ YR ⁵¹ _3-a (CR ⁵² R ⁵³ ) _b N ⁺ R ⁵⁴ R ⁵⁵ R ⁵⁶ _a ]; Y system C or Si; R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ , R ⁵⁵ and R ⁵⁶ are each independently hydrogen Halogen; (C1 to C20) alkyl; (C1 to C20) alkyl containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C2 to C20) alkenyl; containing halogen, nitrogen (C2 to C20) alkenyl group of one or more of oxygen, hydrazine, sulfur, and phosphorus; (C1 to C20) alkyl (C6 to C20) aryl; containing halogen, nitrogen, oxygen, hydrazine, sulfur, and (C1 to C20)alkyl (C6 to C20) aryl; (C6 to C20) aryl (C1 to C20) alkyl; containing halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus One or more of (C6 to C20) aryl (C1 to C20) alkyl; (C1 to C20) alkoxy; (C6 to C30) aryloxy; formazan; (C1 to C20) alkylcarbonyl ; (C6 to C20) aryl-carbonyl group; or a hydrocarbyl-substituted metalloid of Group 14 of the metals radical; and R ^54, both R ⁵⁵ and R ⁵⁶ in the can connected to each other to form a ring; A system of 1 to 3 An integer, and b is an integer from 1 to 20; n is an integer of 4 or greater, obtained by adding 1 to the total number of quaternary amine salts included in R ³ to R ¹⁰ ; and when a is 1, R ³ to R At least three of ¹⁰ may be -[YR ⁵¹ _3-a (CR ⁵² R ⁵³ ) _b N ⁺ R ⁵⁴ R ⁵⁵ R ⁵⁶ _a ], when a is 2, at least two of R ³ to R ¹⁰ may be Is -[YR ⁵¹ _3-a (CR ⁵² R ⁵³ ) _b N ⁺ R ⁵⁴ R ⁵⁵ R ⁵⁶ _a ], when a is 3, at least one of R ³ to R ¹⁰ may be -[YR ⁵¹ _{3- a} (CR ⁵² R ⁵³ ) _b N ⁺ R ⁵⁴ R ⁵⁵ R ⁵⁶ _a ], and the two solvents which are not mixed with each other may be an organic solvent combination such as toluene, tetrahydrofuran or a mixture thereof, and the aqueous solution contains 0.5% by weight. Up to 10% by weight of an inorganic salt, thereby providing an aliphatic group containing from 2% by weight to 7% by weight, preferably from 2% by weight to 5% by weight, based on the aliphatic polycarbonate polymer obtained, of a cyclic carbonate Polycarbonate polymer.

The substituents described in the present invention, including "alkyl", "alkoxy" and other "alkyl" moieties, include both straight chain and branched chain types. In addition, the "aryl group" described in the present invention is derived from an organic radical which removes an aromatic hydrocarbon of a hydrogen atom, and includes a single ring system or a fused ring system of 4 to 7 ring atoms, preferably each. The ring has 5 or 6 ring atoms, and even includes a form in which a plurality of aryl groups are linked by a single bond. Specific examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, a fluorenyl group, a fluorenyl group and the like, but the invention is not limited thereto. "Alkenyl" as defined herein means a straight-chain, branched or cyclic hydrocarbon radical containing from 2 to 20 carbon atoms and at least one carbon-carbon double bond.

The term "containing one or more of halogen, nitrogen, oxygen, helium, sulfur, and phosphorus" as used herein means a substituent including one or more of halogen, nitrogen, oxygen, helium, sulfur, and phosphorus, For example, "an alkyl group containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus" means that one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus are substituted. Alkyl group. Specifically, it includes a haloalkyl group, an alkoxy group, and an aminoalkyl group, but the present invention is not limited thereto.

According to an exemplary embodiment of the present invention, the (C1 to C20) alkyl group, the (C1 to C20) alkoxy group, and the (C3 to C20) cycloalkyl group may preferably be a (C1 to C10) alkyl group, ( C1 to C10) alkoxy, (C3 to C12) cycloalkyl; (C6 to C20) aryl may preferably be (C6 to C12) aryl.

Further, the present invention provides an apparatus for separating an aliphatic polycarbonate polymer and a catalyst in a reaction mixture of an aliphatic polycarbonate polymerization carried out in the presence of a catalyst from the reaction mixture, the catalyst system a complex comprising a phosphonium salt, the apparatus comprising: a reactor 100 for performing an aliphatic polycarbonate polymerization catalyzed by the rhodium-containing complex catalyst; a phase separator 200 The organic layer and the aqueous layer are separated by adding a solvent which is not mixed with each other to the reaction mixture obtained by the polymerization of the reactor, and performing an extraction treatment; a refiner 300 for using the phase separator The aliphatic polycarbonate is obtained in the separated organic layer; and a catalyst collector (not shown) for collecting the catalyst from the aqueous layer separated by the phase separator.

According to the apparatus of the present invention, the reactor 100 is an epoxy compound and The place where carbon dioxide reacts in the presence of a ruthenium salt complex catalyst to carry out polymerization of the aliphatic polycarbonate. When the polymerization is completed in the reactor, the reaction mixture can be moved to the phase separator 200, and two solvents which are not mixed with each other are placed in the phase separator to separate into an organic layer and an aqueous layer, wherein The phase separation can be carried out without adding the reaction mixture to the phase separator, and adding two kinds of mutually incompatible solvents to the reactor, so that in this case, the reactor can be separated by one phase. Device.

The reaction complex prepared in the reactor of the present invention can be moved to the phase separator 200 by the first pump 410, and the aqueous solution containing the inorganic salt can be added to the phase separator 200 by the second pump 420.

The organic layer separated from the phase separator can be moved to the refiner 300 by the third pump 430, and the organic solvent can be discharged to the organic solvent discharge portion 510 by distillation under reduced pressure, and can be collected by aliphatic polycarbonate. The ester discharge portion 520 obtains an aliphatic polycarbonate and can be additionally refined to obtain a higher purity aliphatic polycarbonate.

The aqueous layer separated from the phase separator can be moved to the catalyst collector (not shown) by the fourth pump 440, the catalyst and reaction by-products can be removed, and by additional refining, The resulting catalyst can be collected for reuse.

The invention will be described in more detail below with reference to examples and comparative examples. However, the following examples are merely illustrative of the invention and are not intended to limit the scope of the invention.

[Examples]

[Example 1] Preparation of Polypropylene Carbonate Diol Solution

100.0 ml of propylene oxide and 50.0 ml of toluene were placed in a 500 ml high-pressure reactor, and 6.3 g of adipic acid and 0.5 g of a catalyst having the structure of the following structural formula 1 were placed. The reactor was completely sealed and maintained under conditions of 20 bar of carbon dioxide, a reactor internal temperature of 50 ° C to 55 ° C, and a stirring rate of 500 rpm. After 15 hours, the reactor was cooled to room temperature, the pressure of carbon dioxide was lowered to atmospheric pressure, and 0.5 g of malonic acid was added to complete the reaction.

[Example 2] A method of extracting a catalyst with a 0.8% by weight aqueous sodium chloride solution to remove a catalyst

500 ml of toluene was added to a polypropylene carbonate glycol solution (cyclopropene carbonate: 9%) and stirred, and the reaction of the polypropylene carbonate glycol solution was carried out under the polymerization conditions of the above Example 1. 400 ml of a 0.8% by weight aqueous sodium chloride solution was added and stirred for 30 minutes, followed by removal of the aqueous layer. The extracted toluene layer was distilled under reduced pressure to remove toluene to obtain 141 g of a polypropylene carbonate diol. (cyclopropene carbonate: 6%, cobalt: 1.6 ppm, molecular weight: 1626 g/m)

[Example 3] Method of extracting three times with 0.8% by weight aqueous sodium chloride solution to remove catalyst

500 ml of toluene was added to a polypropylene carbonate glycol solution (cyclopropene carbonate: 9%) and stirred, and the reaction of the polypropylene carbonate glycol solution was carried out under the polymerization conditions of the above Example 1. 400 ml of a 0.8% by weight aqueous sodium chloride solution was added and stirred for 30 minutes, followed by removal of the aqueous layer. 400 ml of a 0.8% aqueous sodium chloride solution was added to the separated toluene layer and further extracted to carry out twice. The extracted toluene layer was distilled under reduced pressure to remove toluene to obtain 137 g of a polypropylene carbonate diol. (cyclopropene carbonate: 3%, cobalt: 0 ppm, molecular weight: 2339 g/m)

[Example 4] Method of extracting three times with 0.1% by weight aqueous sodium chloride solution to remove catalyst

500 ml of toluene was added to a polypropylene carbonate glycol solution (cyclopropene carbonate: 9%) and stirred, and the reaction of the polypropylene carbonate glycol solution was carried out under the polymerization conditions of the above Example 1. 400 ml of a 0.1% by weight aqueous sodium chloride solution was added and stirred for 30 minutes, followed by removal of the aqueous layer. The extracted toluene layer was distilled under reduced pressure to remove toluene to obtain 120 g of a polypropylene carbonate diol. (cyclopropene carbonate: 3%, cobalt: 18 ppm, molecular weight: 2322 g/m)

[Example 5] Method of extracting three times with 5.0% by weight aqueous sodium chloride solution to remove catalyst

500 ml of toluene was added to a polypropylene carbonate glycol solution (cyclopropene carbonate: 16%) and stirred, and the reaction of the polypropylene carbonate glycol solution was carried out under the polymerization conditions of the above Example 1. Add 400 ml of 5.0 A weight % sodium chloride aqueous solution was stirred and allowed to stand for 30 minutes, followed by removal of the aqueous layer. 400 ml of a 5.0% aqueous sodium chloride solution was added to the separated toluene layer and further extracted to carry out twice. The extracted toluene layer was distilled under reduced pressure to remove toluene to obtain 139 g of a polypropylene carbonate diol. (cyclopropene carbonate: 2%, cobalt: 0 ppm)

[Example 6] Method of extracting three times with a 11.0% by weight aqueous sodium chloride solution to remove a catalyst

500 ml of toluene was added to a polypropylene carbonate glycol solution (cyclopropene carbonate: 16%) and stirred, and the reaction of the polypropylene carbonate glycol solution was carried out under the polymerization conditions of the above Example 1. 400 ml of a 11.0% by weight aqueous sodium chloride solution was added and stirred for 30 minutes, followed by removal of the aqueous layer. 400 ml of a 11.0% aqueous sodium chloride solution was added to the separated toluene layer and further extracted to carry out twice. The extracted toluene layer was distilled under reduced pressure to remove toluene to obtain 135 g of a polypropylene carbonate diol. (cyclopropene carbonate: 6%, cobalt: 12 ppm)

[Example 7] Method of extracting three times with a tetrahydrofuran-water mixture to remove a catalyst

400 ml of toluene and 100 ml of tetrahydrofuran were added to a polypropylene carbonate diol solution (cyclopropene carbonate: 6%), and the reaction of the polypropylene carbonate diol solution was carried out under the polymerization conditions of the above Example 1. Finished. 400 ml of water was added and stirred for 30 minutes, followed by removal of the aqueous layer. 400 ml of water was added to the separated toluene layer and further extracted for two times. The extracted toluene layer was distilled under reduced pressure to remove an organic solvent to obtain 136 g of a polypropylene carbonate diol. (cyclopropene carbonate: 2%, cobalt: 15 ppm, molecular weight: 1536 g/m)

[Example 8] Method of extracting three times with acetonitrile-5.0% by weight aqueous sodium chloride solution to remove catalyst

500 ml of acetonitrile was added to a polypropylene carbonate glycol solution (cyclopropene carbonate: 6%), and the reaction of the polypropylene carbonate glycol solution was carried out under the polymerization conditions of the above Example 1. 400 ml of a 5.0% by weight aqueous sodium chloride solution was added and stirred for 30 minutes, followed by removal of the aqueous layer. 400 ml of water was added to the separated toluene layer and further extracted for two times. The extracted toluene layer was distilled under reduced pressure to remove an organic solvent to obtain 105 g of a polypropylene carbonate diol. (cyclopropene carbonate: 5%, cobalt: 7 ppm, molecular weight: 2115 g/m)

[Comparative Example 1] Method for removing catalyst by ion exchange resin

A column having a diameter of 4.0 cm and a length of 30.0 cm was filled with an ion exchange resin (Amberlyst 15), and a sufficient amount of dichloromethane was poured thereinto. 30 g of polypropylene carbonate diol (cyclopropene carbonate: 12%) was diluted with 100 ml of dichloromethane in a column packed with ion exchange resin or silicone, and the reaction of the polypropylene carbonate diol was carried out. This was done under polymerization conditions and then flowed into a column packed with adsorbent at a flow rate of 3.0 ml/min. The organic solvent was removed by distillation under reduced pressure to obtain 30 g of a polypropylene carbonate diol. (cyclopropene carbonate: 12%, cobalt: 60 ppm, molecular weight: 1870 g/m)

[Comparative Example 2] Method for removing catalyst by silicone

A column having a diameter of 4.0 cm and a length of 30.0 cm was filled with 20 g of silicone and a sufficient amount of dichloromethane was poured thereinto. 30 g of polypropylene carbonate diol (cyclopropene carbonate: 12%) was diluted with 100 ml of dichloromethane in a column packed with ion exchange resin or silicone, and the reverse of the polypropylene carbonate diol This should be done under polymerization conditions and then flowed into a column packed with adsorbent at a flow rate of 3.0 ml/min. The organic solvent was removed by distillation under reduced pressure to obtain 30 g of a polypropylene carbonate diol. (cyclopropene carbonate: 12%, cobalt: 49 ppm, molecular weight: 1870 g/m)

As is apparent from the results of the examples, since the aliphatic polycarbonate polymer obtained by the separation method of the present invention has a high cyclic carbonate (which is a by-product during polymerization) removal rate, it is in aliphatic polycarbonate. The content of the cyclic carbonate in the ester polymer is remarkably low, and the metal cobalt content due to the catalyst is also remarkably low, so that the removal rate of the catalyst is high.

Further, it is also known that the cyclic carbonate produced by the separation according to the existing separation method does not occur, and therefore, the separation method of the present invention is a remarkable and effective treatment, which can be efficiently and economically obtained with a simple treatment. Purity aliphatic polycarbonate polymer.

100‧‧‧reactor

200‧‧‧ phase separator

300‧‧‧Refiner

410‧‧‧First pump

420‧‧‧Second pump

430‧‧‧ third pump

440‧‧‧fourth pump

510‧‧‧Organic solvent discharge section

520‧‧‧Polycarbonate discharge

Claims (8)

A method for separating an aliphatic polycarbonate polymer and a catalyst, the aliphatic polycarbonate polymer and the catalyst in a reaction mixture of an aliphatic polycarbonate polymerization carried out in the presence of a catalyst, the contact The medium is a complex containing an onium salt in which two solvents which are not mixed with each other are used in the reaction mixture. The method of claim 1, wherein the two solvents which are not mixed with each other are an organic solvent and an aqueous solution. The method of claim 1, comprising: a) polymerizing carbon dioxide and an epoxide compound in the presence of the cerium salt-containing complex catalyst; b) adding the two solvents which are not mixed with each other In the reaction mixture of step a), and subjected to an extraction treatment to separate the organic layer and the aqueous layer; c) obtaining an aliphatic polycarbonate from the separated organic layer; and d) collecting the separated aqueous layer from the separated layer catalyst. The method of claim 2 or 3, wherein the organic solvent is selected from at least one of toluene, benzene, tetrahydrofuran, and (dichloromethane, ethyl acetate), and the aqueous solution contains 0.1% by weight to 10% by weight. Inorganic salt. The method of claim 1 or 3, wherein the aliphatic polycarbonate polymer is polypropylene carbonate, polyethylene carbonate, polycyclohexene carbonate, polybutadiene Polybutylene carbonate, or polycyclopentene carbonate. The method of claim 3, wherein the epoxy compound is selected from at least one of the group consisting of: or without halogen, (C1 to C20) alkoxy, (C6 to C20) aryloxy, or (C6) To C20) aryl (C1 to C20) alkyl (aralkyl)oxy ((C6-C20)ar(C1-C20)alkyl(aralkyl)oxy) substituted (C2 to C20) alkylene oxide (alkylene) Oxide; substituted with or without halogen, (C1 to C20) alkoxy, (C6 to C20) aryloxy, or (C6 to C20) aryl (C1 to C20) alkyl (aralkyl)oxy (C4 to C20) cycloalkylene oxide; and with or without halogen, (C1 to C20) alkoxy, (C6 to C20) aryloxy, (C6 to C20) aryl (C1 to C20) an alkyl (aralkyl)oxy group or a (C1 to C20) alkyl substituted (C8 to C20) styrene oxide. The method of claim 1 or 3, wherein the complex salt containing a sulfonium salt has the following chemical formula 1: In Chemical Formula 1, M is a trivalent cobalt or a trivalent chromium; A is an oxygen atom or a sulfur atom; Q is a diradical connecting a dinitrogen atom; R ¹ to R ¹⁰ are each independently hydrogen; halogen; (C1 to C20) alkyl; (C1 to C20) alkyl containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C2 to C20) alkenyl; containing halogen, nitrogen, oxygen, hydrazine, sulfur And (C2 to C20) alkenyl group of one or more of phosphorus; (C1 to C20) alkyl (C6 to C20) aryl; one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus (C1 to C20) alkyl (C6 to C20) aryl; (C6 to C20) aryl (C1 to C20) alkyl; containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus (C6 to C20) aryl (C1 to C20) alkyl; (C1 to C20) alkoxy; (C6 to C30) aryloxy; indenyl; (C1 to C20) alkylcarbonyl ((C1-C20) Alkylcarbonyl); or (C6 to C20) an arylcarbonyl group ((C6-C20) arylcarbonyl); or a metal radical such as a Group 14 metal substituted with a (C1 to C20) alkyl group or a (C6 to C20) aryl group; ¹ to R ¹⁰ may be connected to each other to form a ring; at least one hydrogen group included in R ¹ to R ¹⁰ and Q is selected from the following chemical formulas a, b, and a proton group of the group consisting of c; X ^- each independently is a halogen anion; HCO ₃ ^- ; BF ₄ ^- ; ClO ₄ ^- ; NO ₃ ^- ; PF ₆ ^- ; (C6 to C20) aryloxy anion; contains a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom a (C6 to C20) aryloxy anion of one or more of a sulfur atom and a phosphorus atom; (C1 to C20) an alkylcarboxy anion; containing a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and (C1 to C20) alkylcarboxy anion of one or more of phosphorus atoms; (C6 to C20) arylcarboxy anion; containing one of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom or a plurality of (C6 to C20) arylcarboxy anions; (C1 to C20) alkoxy anions; containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom (C1) To a C20) alkoxy anion; (C1 to C20) alkyl carbonate anion; (C1-C20) alkylcarbonate anion; containing one of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom or (C1 to C20) alkyl carbonate anion; (C6 to C20) aryl carbonate anion ((C6-C20) arylcarbo Nate anion); (C6 to C20) aryl carbonate anion containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom; (C1 to C20) alkylsulfonate anion ((C1-C20)alkylsulfonate anion); (C1 to C20) alkylsulfonate anion containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom; (C1 to C20 An alkylguanamine anion; a (C1 to C20) alkylguanamine anion containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom; (C6 to C20) An arylguanidinium anion; an (C6 to C20) arylguanamine anion containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom; (C1 to C20) (C1-C20)alkylcarbamate anion; (C1 to C20) alkylamine formic acid containing one or more of a halogen atom, a nitrogen atom, an oxygen atom, a halogen atom, a sulfur atom, and a phosphorus atom Anion; (C6 to C20) an arylamine anion; or a halogen atom, a nitrogen atom, an oxygen atom, a (C6 to C20) arylcarbamate anion of one or more of a halogen atom, a sulfur atom, and a phosphorus atom; a Z-based nitrogen atom or a phosphorus atom; R ²¹ , R ²² , R ²³ , R ³¹ , R ³² , R ³³ , R ³⁴ , and R ³⁵ are each independently (C1 to C20) alkyl; (C1 to C20) alkyl having one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; C20) alkenyl; (C2 to C20) alkenyl group containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C1 to C20) alkyl (C6 to C20) aryl; containing halogen, (C1 to C20) alkyl (C6 to C20) aryl group of one or more of nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C6 to C20) aryl (C1 to C20) alkyl; containing halogen, nitrogen (C6 to C20) aryl (C1 to C20) alkyl group of one or more of oxygen, hydrazine, sulfur, and phosphorus; or substituted by (C1 to C20) alkyl or (C6 to C20) aryl a metal radical such as a Group 14 metal; two of R ²¹ , R ²² and R ²³ , or two of R ³¹ , R ³² , R ³³ , R ³⁴ , and R ³⁵ , may be bonded to each other to form a ring; R ⁴¹ , R ⁴² , and R ⁴³ are each independently hydrogen; (C1 to C20) alkyl; containing one of halogen, nitrogen, oxygen, helium, sulfur, and phosphorus or a plurality of (C1 to C20) alkyl groups; (C2 to C20) alkenyl groups; (C2 to C20) alkenyl groups containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C1 to C20) An alkyl (C6 to C20) aryl group; a (C1 to C20) alkyl (C6 to C20) aryl group containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; (C6 to C20) Aryl (C1 to C20) alkyl; (C6 to C20) aryl (C1 to C20) alkyl containing one or more of halogen, nitrogen, oxygen, hydrazine, sulfur, and phosphorus; or (C1 to C20) a metal radical such as a Group 14 metal substituted with an alkyl group or a (C6 to C20) aryl group; two of R ⁴¹ , R ⁴² , and R ⁴³ may be bonded to each other to form a ring; X'-based oxygen atom, sulfur An atom or NR, wherein R is a (C1 to C20) alkyl group; n is an integer obtained by adding 1 to the total number of proton groups included in R ¹ to R ¹⁰ and Q; X ^- can be coordinated to M; and imine One of the nitrogen atoms may coordinate or decoordinate with M. An apparatus for separating an aliphatic polycarbonate polymer and a catalyst in a reaction mixture of an aliphatic polycarbonate polymerization carried out in the presence of a catalyst from the reaction mixture, the catalyst containing a strontium salt a device comprising: a reactor for carrying out polymerization of an aliphatic polycarbonate catalyzed by the ruthenium salt-containing complex catalyst; a phase separator by which two species are not in phase with each other The mixed solvent is added to the reaction mixture obtained by the polymerization obtained in the reactor, and subjected to an extraction treatment to separate the organic layer and the aqueous layer; a refiner for the organic layer separated from the phase separator Obtaining the aliphatic polycarbonate; A catalyst collector for collecting the catalyst from an aqueous layer separated by the phase separator.