KR102509969B1 - Palladium complex catalyst and method of synthesizing polyketone using the palladium complex catalyst - Google Patents

Abstract

A palladium composite catalyst having excellent catalytic activity for a terpolymerization reaction of one of vinyl arene and styrene, ethylene and carbon monoxide is disclosed. The palladium complex catalyst includes elemental palladium; and an iminopyridine ligand bound to the palladium element.

Description

Palladium complex catalyst and polyketone synthesis method using the same

The present invention relates to a palladium complex catalyst capable of accelerating a terpolymerization reaction for polyketone synthesis and a polyketone synthesis method using the same.

Developing a technology for synthesizing high value-added compounds from carbon monoxide (CO) through chemical fixation and conversion reactions is economically and environmentally important. For example, the technology of synthesizing polyketone, a high-performance processing plastic, through polymerization of carbon monoxide and ethylene using palladium as a catalyst meets these social needs, and according to this demand, polyketone through copolymerization of ethylene and carbon monoxide Technologies for synthesizing and improving the catalytic activity of the palladium catalyst for the polymerization reaction and controlling the physical properties of the polyketone have been reported. However, polyketone synthesized from the copolymerization reaction of ethylene and carbon monoxide has a melting point (Tm) of 250 ° C or higher, and a higher temperature must be applied for thermal processing of polyketone having such a melting point. Application has a problem that can lead to polymer degradation. Therefore, various studies have been conducted to lower the melting point of polyketone, and one of these studies was terpolymerization of propylene, ethylene and carbon monoxide, and the melting point of polyketone synthesized thereby was reduced to about 220 ° C.

On the other hand, terpolymers containing vinylarene showed different thermal properties (Tg and Tm) compared to ethylene-CO copolymers. Based on this, a polyketone synthesis technology with a relatively low melting point is being developed. . However, since palladium catalysts containing porphyrin ligands are not effective for polymerization reactions containing vinylarene, it is necessary to develop a novel palladium catalyst capable of accelerating a polyketone synthesis reaction using vinylarene.

One object of the present invention is to provide a palladium composite catalyst exhibiting excellent catalytic activity for a terpolymerization reaction of one of vinyl arene and styrene, ethylene and carbon monoxide.

Another object of the present invention is to provide a polyketone synthesis method using the palladium complex catalyst.

A palladium composite catalyst according to an embodiment of the present invention is a catalyst capable of promoting a terpolymerization reaction of one of vinyl arene and styrene, ethylene and carbon monoxide, and includes a palladium element; and an iminopyridine ligand bonded to the palladium element.

In one embodiment, the iminopyridine ligand may include one selected from compounds represented by Chemical Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formula 1, R1 is one selected from a methyl group and a phenyl group, and each of R2 and R3 is independently hydrogen (-H), a hydroxyl group (-OH), a methyl group (-CH ₃ ), an isopropyl group (-CH (CH ₃ ) ₂ ) and a methoxy group (-OCH ₃ ).

In one embodiment, the palladium complex catalyst may include one selected from compounds represented by Chemical Formulas 2-1 to 2-3.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formula 2-1, R1 is one selected from a methyl group and a phenyl group, and each of R2 and R3 is independently selected from hydrogen, a hydroxy group (-OH), a methyl group, an isopropyl group, and a methoxy group, and Formula 2 In -2 and 2-3, each of R _a , R _b , R _c and R _d is independently selected from a methyl group and acetonitrile (-NCCH ₃ ).

The polyketone synthesis method according to an embodiment of the present invention includes the step of terpolymerizing one of vinyl arene and styrene, ethylene and carbon monoxide in the presence of the palladium complex catalyst.

In one embodiment, in the terpolymerization reaction, the vinylarene or styrene and the palladium composite catalyst may be provided in a dissolved state, and the ethylene and carbon monoxide may be provided in a gaseous state.

In one embodiment, the solvent is trifluoroethanol (2,2,2-trifluoroethanol, TFE), hexafluoroisopropanol (Hexafluoroisopropanol, HFIP), dichloromethane, chlorobenzene, methanol (MeOH) And it may include one or more selected from the group consisting of ethanol (EtOH).

In one embodiment, the terpolymerization reaction may be performed at a temperature of about 25 °C to 50 °C.

In one embodiment, in the terpolymerization reaction of styrene, ethylene and carbon monoxide, the styrene is provided in a concentration of 10 to 30 mmol, and the palladium complex catalyst is provided in a ratio of 0.1 to 1 μmol based on 1000 μmol of the styrene The carbon monoxide and the ethylene may be provided at a pressure ratio of 1:3 to 1:30.

In one embodiment, benzoquinone may be provided by dissolving in the solvent together with the styrene and the palladium complex catalyst. In this case, the benzoquinone may be provided in an amount of 0.5 to 2.5 μmol based on 1000 μmol of styrene.

In one embodiment, in the terpolymerization reaction of vinylarene, ethylene and carbon monoxide, the vinylarene is provided at a concentration of 10 to 30 mmol, and the palladium complex catalyst is 0.1 to 1 μmol based on 1000 μmol of the vinylarene It is provided at a ratio of, and the carbon monoxide and the ethylene may be provided at a pressure ratio of 1:3 to 1:30.

In one embodiment, benzoquinone may be provided by dissolving in the solvent together with the vinylarene and the palladium complex catalyst. In this case, the benzoquinone may be provided in an amount of 0.5 to 2.5 μmol based on 1000 μmol of styrene.

According to the palladium complex catalyst of the present invention, it exhibits excellent catalytic activity for the terpolymerization reaction of one of vinyl arene and styrene, ethylene and carbon monoxide, including an iminopyridine ligand. can

In addition, according to the polyketone synthesis method of the present invention, polyketone having excellent physical properties such as a relatively low melting point (Tm) and glass transition temperature (Tg) can be synthesized with high efficiency.

Hereinafter, embodiments of the present invention will be described in detail. Since the present invention may have various changes and various forms, specific embodiments are illustrated in the drawings and described in detail in the text. However, this is not intended to limit the present invention to a specific form disclosed, and should be understood to include all modifications, equivalents, and substitutes included in the spirit and scope of the present invention.

Terms such as first and second may be used to describe various components, but the components should not be limited by the terms. These terms are only used for the purpose of distinguishing one component from another. For example, a first element may be termed a second element, and similarly, a second element may be termed a first element, without departing from the scope of the present invention.

Terms used in this application are only used to describe specific embodiments and are not intended to limit the present invention. Singular expressions include plural expressions unless the context clearly dictates otherwise. In this application, terms such as "comprise" or "have" are intended to designate that there is a feature, step, operation, component, part, or combination thereof described in the specification, but one or more other features or steps However, it should be understood that it does not preclude the possibility of existence or addition of operations, components, parts, or combinations thereof.

Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which the present invention belongs. Terms such as those defined in commonly used dictionaries should be interpreted as having a meaning consistent with the meaning in the context of the related art, and unless explicitly defined in the present application, they should not be interpreted in an ideal or excessively formal meaning. don't

The palladium complex catalyst according to an embodiment of the present invention may include a palladium element and an iminopyridine ligand bonded to the palladium element, and one of vinylarene and styrene, ethylene and carbon monoxide It can be used as a catalyst for the terpolymerization reaction of

In one embodiment, the iminopyridine ligand may include one selected from compounds represented by Chemical Formulas 1-1 to 1-3, and a nitrogen element (N) may be bonded to the palladium element.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formula 1, R1 may be one selected from a methyl group, a phenyl group, etc., and each of R2 and R3 is independently hydrogen (-H), a hydroxyl group (-OH), a methyl group (-CH ₃ ), an isopropyl group ( -CH(CH ₃ ) ₂ ), a methoxy group (-OCH ₃ ), and the like.

In one embodiment, the palladium complex catalyst may include one selected from compounds represented by Chemical Formulas 2-1 to 2-3.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formula 2-1, R1 may be one selected from a methyl group, a phenyl group, and the like, and each of R2 and R3 may be independently selected from hydrogen, a hydroxyl group (-OH), a methyl group, an isopropyl group, a methoxy group, and the like. can And in Chemical Formulas 2-2 and 2-3, R _a , R _b , R _c and R _d may each independently be one selected from a methyl group, acetonitrile (-NCCH ₃ ), and the like.

The palladium composite catalyst of the present invention can exhibit excellent catalytic activity for the terpolymerization reaction of one of vinyl arene and styrene, ethylene and carbon monoxide for polyketone synthesis having excellent physical properties. .

The polyketone synthesis method according to an embodiment of the present invention includes the step of terpolymerizing one of vinyl arene and styrene, ethylene and carbon monoxide in the presence of a palladium complex catalyst.

Since the palladium complex catalyst of the present invention described above can be used as the palladium complex catalyst, repeated detailed description thereof will be omitted.

In one embodiment, the terpolymerization reaction is a terpolymerization reaction of styrene, ethylene and carbon monoxide according to the following reaction formula 1 or a terpolymerization of vinyl arene, ethylene and carbon monoxide according to the following reaction formula 2 (terpolymerization) reaction.

[Scheme 1]

[Scheme 2]

는 약 0.05 이상 0.3 이하일 수 있다. In Scheme 1, the molecular weight of the synthesized polyketone is about 11 to 33 kDa, n may be an integer of about 60 to 180, in this case,

may be greater than or equal to about 0.05 and less than or equal to 0.3.

는 약 0.1 이상 0.7 이하일 수 있다. 예를 드면, 상기 반응식 2에서, R이 염소(Cl)인 경우에는

이 약 0.05 이상 0.20 이하일 수 있고, R이 메틸기인 경우에는

이 약 0.25 이상 0.40 이하일 수 있으며, R이 메톡시기인 경우에는

이 약 0.60 이상 0.70 이하일 수 있다. In Scheme 2, the molecular weight of the synthesized polyketone is about 13 to 120 kDa, n may be an integer of about 60 to 600, in this case,

may be greater than or equal to about 0.1 and less than or equal to 0.7. For example, in Scheme 2 above, when R is chlorine (Cl),

This may be about 0.05 or more and 0.20 or less, and when R is a methyl group,

This may be about 0.25 or more and 0.40 or less, and when R is a methoxy group,

It may be about 0.60 or more and 0.70 or less.

In the terpolymerization reaction of styrene, ethylene and carbon monoxide according to Scheme 1, the styrene and palladium complex catalyst may be provided in a dissolved state in a solvent, and the ethylene and carbon monoxide may be provided in a gaseous state .

In one embodiment, the solvent is trifluoroethanol (2,2,2-trifluoroethanol, TFE), hexafluoroisopropanol (Hexafluoroisopropanol, HFIP), dichloromethane, chlorobenzene, methanol (MeOH) ), one or more selected from ethanol (EtOH) and the like may be used. For example, trifluoroethanol or hexafluoroisopropanol may be used as the solvent.

In one embodiment, the styrene may be provided in a concentration of about 10 to 30 mmol, and the palladium complex catalyst may be provided in a ratio of about 0.1 to 1 μmol based on 1000 μmol of the styrene. Meanwhile, the carbon monoxide and the ethylene may be provided at a pressure ratio of about 1:3 to 1:30, and in this case, the ethylene may be provided at a ratio of about 3 to 9 mmol with respect to 1 mmol of the styrene. For example, the ethylene may be provided in a ratio of about 4 to 8 mmol with respect to 1 mmol of the carbon monoxide.

In one embodiment, for the terpolymerization reaction of Scheme 1, benzoquinone (BQ) may be provided by being dissolved in the solvent. The benzoquinone may act as an oxidizing agent that prevents palladium from being reduced to palladium black from the palladium complex catalyst. For example, the benzoquinone may be provided in an amount of about 0.5 to 2.5 μmol based on 1000 μmol of the styrene.

In one embodiment, the terpolymerization reaction of Scheme 1 may be performed at a temperature of about 25°C to 50°C.

In the terpolymerization reaction of vinylarene, ethylene and carbon monoxide according to Scheme 2, the vinylarene and palladium composite catalyst may be provided in a state dissolved in a solvent, and the ethylene and carbon monoxide are gaseous condition can be provided.

In one embodiment, the solvent is trifluoroethanol (2,2,2-trifluoroethanol, TFE), hexafluoroisopropanol (Hexafluoroisopropanol, HFIP), dichloromethane, chlorobenzene, methanol (MeOH) ), one or more selected from ethanol (EtOH) and the like may be used. For example, trifluoroethanol or hexafluoroisopropanol may be used as the solvent.

In one embodiment, the vinylarene may be provided in a concentration of about 10 to 30 mmol, and the palladium complex catalyst may be provided in a ratio of about 0.1 to 1 μmol based on 1000 μmol of the vinylarene. Meanwhile, the carbon monoxide and the ethylene may be provided at a pressure ratio of about 1:3 to 1:30, and in this case, the ethylene may be provided at a ratio of about 3 to 9 mmol with respect to 1 mmol of the vinylarene. For example, the ethylene may be provided in a ratio of about 4 to 8 mmol with respect to 1 mmol of the carbon monoxide.

In one embodiment, for the terpolymerization reaction of Scheme 2, benzoquinone (BQ) may be provided by being dissolved in the solvent. The benzoquinone may act as an oxidizing agent that prevents palladium from being reduced to palladium black from the palladium complex catalyst. For example, the benzoquinone may be provided in an amount of about 0.5 to 2.5 μmol based on 1000 μmol of styrene.

In one embodiment, the terpolymerization reaction of Scheme 2 may be performed at a temperature of about 25°C to 50°C.

According to the polyketone synthesis method of the present invention, polyketone having excellent physical properties such as a relatively low melting point (Tm) and glass transition temperature (Tg) can be synthesized with high efficiency.

Hereinafter, specific embodiments of the present invention will be described in detail. However, the following examples are merely some embodiments of the present invention, and the scope of the present invention is not limited to the following examples.

<Examples 1-1 to 1-3: Synthesis of Single Metal Palladium Composite Catalyst>

A template synthetic procedure for one-pot reaction of 2-acetyl pyridine, first aniline derivatives and (COD) PdMeCl according to Scheme 3-1 below Through this, palladium complexes 1a to 4a were synthesized.

Subsequently, palladium complexes 1a to 4a were treated with AgPF ₆ to synthesize cationic palladium complexes 1b to 4b.

[Scheme 3-1]

<Example 1-4: Synthesis of double metal palladium composite catalyst>

According to the following Scheme 3-2, 2-acetyl pyridine, second aniline derivatives, formic acid (HCOOH) and (COD) PdMeCl ('COD' represents cyclooctadiene) were reacted to form two A palladium complex 5a containing elemental palladium was synthesized.

Subsequently, the palladium complex 5a was treated with AgPF ₆ to synthesize a cationic palladium complex 5b.

[Scheme 3-2]

<Example 1-5: Synthesis of double metal palladium composite catalyst>

Palladium complex 6a containing two palladium elements was prepared by reacting 2-acetyl pyridine, tertiary aniline derivatives, formic acid (HCOOH) and (COD) PdMeCl according to Scheme 3-3 below. synthesized.

Subsequently, the palladium complex 6a was treated with AgPF ₆ to synthesize a cationic palladium complex 6b.

[Scheme 3-3]

<Examples 2-1 to 2-6>

Polyketone was synthesized by inducing terpolymerization of ethylene, carbon monoxide and styrene while changing the palladium complex catalyst according to Scheme 4-1 below.

Specifically, 1,4-benzoquinone (BQ) (3.5 mg, 32 μmol), palladium complex catalyst (6.35 μmol) and vinylarene (20 mmol) were mixed in TFE (2,2,2-trifluoroethanol) (10 mL) solvent. After the solution was filled in the autoclave, the air in the autoclave was replaced with ethylene gas at 30 bar. Subsequently, 5 bar of carbon monoxide gas was supplied until the total pressure reached 35 bar. The reaction mixture was stirred at 250 rpm and heated to 30 °C for 18 hours. After 18 hours, unreacted gas was removed, and the compound was transferred to a 20 mL vessel. Then, after separating the compound through filtering, it was dried in an oven at 65° C. for 3 days.

[Scheme 4-1]

<Experimental example>

Table 1 below shows the results of measuring the styrene insertion rate and catalytic activity for the terpolymerization reaction of Examples 2-1 to 2-6, and Table 2 shows the palladium complex 1b for the copolymerization reaction of ethylene and carbon monoxide. Table 3 shows the results of measuring the catalytic activities of palladium composites 1b to 6b for the copolymerization reaction of styrene and carbon monoxide. The copolymerization reactions in Tables 2 and 3 were carried out in trifluoroethanol (TFE) at 30 °C.

reaction catalyst ethylene
(bar) CO
(bar) styrene
(mmol) styrene
insertion(%) activity
(g/g-Pd) One 1b 30 5 20 20 1788 2 2b 30 5 20 30 1885 3 3b 30 5 20 24 3144 4 4b 30 5 20 5 2067 5 5b 30 5 20 11 2311 6 6b 30 5 20 13 1416

reaction catalyst ethylene
(bar) CO
(bar) styrene
(mmol) styrene
insertion(%) activity
(g/g-Pd) 7 1b 30 5 - - 657 8 2b 30 5 - - 618 9 3b 30 5 - - 592 10 4b 30 5 - - 1475 11 5b 30 5 - - 678 12 6b 30 5 - - 657

reaction catalyst ethylene
(bar) CO
(bar) styrene
(mmol) styrene
insertion(%) activity
(g/g-Pd) 13 1b - One 20 - 654 14 2b - One 20 - 2160 15 3b - One 20 - 2033 16 4b - One 20 - 228 17 5b - One 20 - 1139 18 6b - One 20 - 1129

Referring to Table 2, for the copolymerization reaction of ethylene and carbon monoxide, the catalyst 4b containing a bulky ligand showed the highest catalytic activity, but a short polymer chain was formed when using it. The fact that catalyst 4b shows the highest catalytic activity means that the steric effect of the ligand does not reduce the catalytic activity. Referring to Table 1, for the terpolymer reaction of ethylene, carbon monoxide and styrene, catalyst 3b has the highest catalyst activity. activity, catalyst 2b showed the highest styrene insertion. Catalyst 4b containing a sterically bulky ligand showed a relatively high activity, but a low styrene intercalation rate.

Referring to Table 3 together with Table 1, copolymerization of styrene and CO was investigated to evaluate the effect of styrene on the catalytic activity of terpolymerization in the presence of various catalysts. Catalyst 1b containing an OH group and Catalyst 4b containing an isopropyl group formed copolymers with activities of 654 g/g-Pd and 228 g/g-Pd. Interestingly, the methoxy group (-OMe) substitution catalyst 2b showed much higher activity compared to catalyst 3b (see reactions 14 and 15).

Overall, Catalyst 1b showed similar activity in the copolymerization of ethylene/CO and styrene/CO, but the styrene intercalation ratio was 20% due to the increased catalytic activity in terpolymerization. Catalyst 2b containing a methoxy group in the iminopyridine ligand showed much higher activity in the copolymerization of styrene/CO, and in terpolymerization, the styrene insertion ratio was higher than the other catalysts, but the catalytic activity was reduced. Catalyst 3b showed catalytic activity similar to that of catalyst 2b in copolymerization, but the activity of terpolymerization increased higher than that of other catalysts. Catalyst 4b showed increased catalytic activity in terpolymerization, although it was not effective in styrene/CO copolymerization. Catalyst 4b exhibited a low styrene intercalation rate, reflecting the low activity in styrene/CO copolymerization and low styrene intercalation rate in the terpolymer. Catalysts 5b and 6b showed similar activity in copolymerization of ethylene/CO and styrene/CO, but catalyst 5b showed higher activity than catalyst 6b in terpolymerization.

<Examples 3-1 to 3-9>

Polyketone was synthesized by inducing terpolymerization of ethylene, carbon monoxide and styrene using 3b (6.35 μmol) as a catalyst according to Scheme 4-1 and changing the solvent, CO pressure, and BQ amount. Polyketone was synthesized by inducing terpolymerization of ethylene, carbon monoxide and styrene for 18 hours under conditions of 10 mL of solvent and 30 ° C. in a 50 mL reactor, and other process processes were as described in Examples 2-1 to 2-6 It went on practically the same way.

<Experimental example>

Table 4 shows the results of measuring the catalytic activity for the terpolymerization reaction of Examples 3-1 to 3-9.

reaction catalyst
(6.35 µmol) ethylene
(bar) CO
(bar) styrene
(mmol) BQ
(μmol) menstruum activity
(g/g-Pd) One 3b 30 5 20 32 TFE 3144 2 3b 30 5 20 32 HFIP 1514 3 3b 30 5 20 32 MeOH 942 4 3b 30 5 20 32 EtOH 744 5 3b 30 5 30 32 TFE 2747 6 3b 30 One 20 32 TFE 2471 7 3b 20 5 20 32 TFE 2709 8 3b 30 5 20 16 TFE 2579

Referring to Table 4, in the terpolymerization reaction using catalyst 3b, the highest activity was exhibited when TFE was used as a solvent, and the higher the pressure of ethylene and carbon monoxide under the same conditions (Reactions 1 and 7, Scheme 5 and 6), the smaller the amount of styrene (compare reactions 1 and 5) and the greater the amount of benzoquinone (BQ) (compare reactions 1 and 8), the higher the activity. However, these conditions did not further increase the catalytic activity.

<Examples 4-1 to 4-3>

Polyketone was synthesized by inducing terpolymerization of ethylene and carbon monoxide using 3b (6.35 µmol) as a catalyst and different vinylarenes according to Scheme 4-2 below.

[Scheme 4-2]

<Experimental example>

Table 5 shows the results of measuring the vinyl arene insertion and catalytic activity for the terpolymerization reactions of Examples 4-1 to 4-3.

reaction R Vinyl arene insertion (%) activity
(g/g-Pd) One Cl 16 2085 2 Me 31 2357 3 OMe 55 4159

Referring to Table 5, the highest catalytic activity and the highest vinylarene insertion rate were exhibited when the vinylarene contained a methoxy group.

Although the above has been described with reference to preferred embodiments of the present invention, those skilled in the art can variously modify and change the present invention without departing from the spirit and scope of the present invention described in the claims below. You will understand that you can.

Claims (13)

As a catalyst capable of promoting a terpolymerization reaction of one of vinyl arene and styrene, ethylene and carbon monoxide,
elemental palladium; and
It includes an iminopyridine ligand bonded to the palladium element,
A palladium complex catalyst comprising one selected from compounds represented by Formulas 2-2 and 2-3:
[Formula 2-2]

[Formula 2-3]

In Chemical Formulas 2-2 and 2-3, each of Ra, Rb, Rc, and Rd is independently selected from a methyl group and acetonitrile (-NCCH ₃ ).

delete delete A method for synthesizing polyketone, comprising the step of terpolymerizing one of vinyl arene and styrene, ethylene and carbon monoxide in the presence of the palladium complex catalyst of claim 1. According to claim 4,
In the terpolymerization reaction, the styrene or vinylarene and the palladium complex catalyst are provided in a dissolved state in a solvent, and the ethylene and carbon monoxide are provided in a gaseous state. According to claim 5,
The solvent is trifluoroethanol (2,2,2-trifluoroethanol, TFE), hexafluoroisopropanol (Hexafluoroisopropanol, HFIP), dichloromethane, chlorobenzene, methanol (MeOH) and ethanol (EtOH) Characterized in that it comprises at least one selected from the group consisting of, a method for synthesizing polyketone. According to claim 6,
The terpolymerization reaction is characterized in that carried out at a temperature of 25 ℃ to 50 ℃, a method for synthesizing a polyketone. According to claim 6,
In the terpolymerization reaction of styrene, ethylene and carbon monoxide, the styrene is provided in a concentration of 10 to 30 mmol, the palladium complex catalyst is provided in a ratio of 0.1 to 1 μmol based on 1000 μmol of the styrene, and the carbon monoxide and the ethylene is provided at a pressure ratio of 1:3 to 1:30, polyketone synthesis method. According to claim 8,
A method for synthesizing a polyketone, characterized in that benzoquinone is dissolved in the solvent together with the styrene and the palladium complex catalyst. According to claim 9,
The method for synthesizing a polyketone, characterized in that the benzoquinone is provided in an amount of 0.5 to 2.5 μmol based on 1000 μmol of the styrene. According to claim 6,
In the terpolymerization reaction of vinylarene, ethylene, and carbon monoxide, the vinylarene is provided in a concentration of 10 to 30 mmol, and the palladium complex catalyst is provided in a ratio of 0.1 to 1 μmol based on 1000 μmol of the vinylarene, , The method for synthesizing polyketone, characterized in that the carbon monoxide and the ethylene are provided at a pressure ratio of 1:3 to 1:30. According to claim 11,
A method for synthesizing a polyketone, characterized in that benzoquinone is dissolved in the solvent together with the vinylarene and the palladium complex catalyst. According to claim 12,
The method for synthesizing a polyketone, characterized in that the benzoquinone is provided in an amount of 0.5 to 2.5 μmol based on 1000 μmol of the vinylarene.