JP6786811B2 - Compositions containing organic base compounds, Lewis acids and active hydrogen-containing compounds - Google Patents

Description

The present invention relates to a composition containing an organic base compound, a Lewis acid and an active hydrogen-containing compound. The present invention also relates to an efficient method for producing a polyalkylene oxide having a high molecular weight, a low degree of unsaturation and a narrow molecular weight distribution using the present composition as a catalyst.

A method of performing ring-opening polymerization of an alkylene oxide in the presence of an organic base compound represented by the following general formula (A) and an active hydrogen-containing compound is known (see, for example, Patent Document 1).

(In the above general formula (A), l, m and n represent positive integers of 0 or 3 or less, respectively. D is a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group and a phenoxy of the same type or different types. A group, thiol residue, thiophenol residue, monosubstituted amino group, disubstituted amino group or 5- to 6-membered cyclic amino group. Q is a hydrocarbon group having 1 to 20 carbon atoms.)
Further, a method of ring-opening polymerization of an alkylene oxide in the presence of an organic base compound represented by the following general formula (B) and an active hydrogen-containing compound is known (see, for example, Patent Document 2).

(In the above general formula (B), R may be the same or different, and may be a hydrogen atom, a hydrocarbon group having 1 to 12 carbon atoms, or a silicon atom-containing hydrocarbon having 1 to 12 carbon atoms. It is a hydrogen group.)
Further, a method of ring-opening polymerization of an alkylene oxide in the presence of an organic base compound represented by the following general formula (C), triisobutylaluminum, and an active hydrogen-containing compound is known (see, for example, Non-Patent Document 1). .).

In the method proposed in Patent Document 1, the composition containing an organic base compound and an active hydrogen-containing compound was capable of producing a polyalkylene oxide having a molecular weight of less than 3000, but a polyalkylene oxide having a molecular weight of 3000 or more. Has a problem that it is difficult to produce the compound with high catalytic activity. Further, in Patent Document 1, the degree of unsaturation, which is an index of the amount of impurities in the produced polyalkylene oxide, has not received any attention.

Further, in the method proposed in Patent Document 2, the composition containing the organic base compound and the active hydrogen-containing compound was capable of producing a polyalkylene oxide having a molecular weight of less than 3000, but a poly having a molecular weight of 3000 or more. There is a problem that it is difficult to produce an alkylene oxide with high catalytic activity. Further, the method proposed in Patent Document 2 has a problem that the degree of unsaturation of the produced polyalkylene oxide increases when the polymerization time is shortened.

Further, in the method proposed in Non-Patent Document 1, the composition containing an organic base compound, triisobutylaluminum, and an active hydrogen-containing compound can produce a high-molecular-weight polyalkylene oxide having a molecular weight of 8500 to 80,000. However, it is necessary to use a large amount of an expensive phosphazene compound as an organic base compound, which poses a problem as an efficient method for producing a polyalkylene oxide. Further, in Non-Patent Document 1, no attention has been paid to the degree of unsaturation of the polyalkylene oxide produced.

Patent No. 3534546 JP 2005-223377

Polymer Chemistry, 2012, 3, 1189.

The present invention has been made in view of the background art described above, and an object of the present invention is a composition capable of efficiently producing a polyalkylene oxide having a high molecular weight, a low degree of unsaturation and a narrow molecular weight distribution. And a method for producing a polyalkylene oxide using the same.

The present inventors have made intensive studies in order to solve the above problems, an organic base compound having a specific pK _BH, a composition comprising a Lewis acid, and an active hydrogen-containing compound, a high molecular weight, low unsaturation degree and We have found that it is possible to efficiently produce a polyalkylene oxide having a narrow molecular weight distribution, and have completed the present invention.

That is, the present invention relates to the composition as shown below, a method for producing the same, and a method for producing a polyalkylene oxide using the same.

[1] A composition containing an organic base compound having a pK _BH of 23 or more, a Lewis acid, and an active hydrogen-containing compound.

[2] An organic base compound having a pK _BH of 23 or more is described in the following general formula (1).

(In the above general formula (1), R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Here, R ¹ and R ² are bonded to each other. ring structures, may form a ring structure R ¹ s or R ² together are linked together.)
Compound represented by, the following general formula (2)

(In the above general formula (2), R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Here, R ¹ and R ² are bonded to each other. ring structures, may form a ring structure R ¹ s or R ² together are linked together.)
Compound represented by, the following general formula (3)

(In the above general formula (3), R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, where R ¹ , R ² and R ^{3 are used.} two are ring structure connected with each other among the may form a ring structure R ¹ s or R ² together are linked together.)
Compound represented by, the following general formula (4)

(In the above general formula (4), R independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.)
The compound represented by, and the following general formula (5)

(In the above general formula (5), n represents an integer of 1 to 3).
The composition according to [1], which is at least one compound selected from the group consisting of the compounds represented by.

[3] The composition according to the above [1] or [2], wherein the Lewis acid is at least one compound selected from the group consisting of an aluminum compound, a zinc compound, and a boron compound.

[4] The ratio of the organic base compound having a pK _BH of 23 or more to the Lewis acid is organic base compound: Lewis acid = 1: 0.002 to 500 (molar ratio). The composition according to any one of [3].

[5] The ratio of active hydrogen in the active hydrogen-containing compound to the organic base compound having a pK _BH of 23 or more is active hydrogen in the active hydrogen-containing compound: organic base compound = 1: 0.001 to 10 (molar ratio). The composition according to any one of the above [1] to [4].

[6] The above, wherein the ratio of active hydrogen to Lewis acid in the active hydrogen-containing compound is active hydrogen: Lewis acid = 1: 0.001 to 10 (molar ratio) in the active hydrogen-containing compound. The composition according to any one of [1] to [5].

[7] Production of the composition according to any one of the above [1] to [6], which comprises mixing an organic base compound having a pK _BH of 23 or more and an active hydrogen-containing compound, and then mixing Lewis acid. Method.

[8] An alkylene oxide polymerization catalyst comprising the composition according to any one of the above [1] to [6].

[9] A method for producing a polyalkylene oxide, which comprises performing ring-opening polymerization of an alkylene oxide in the presence of the composition according to any one of the above [1] to [6].

Since the composition of the present invention has high catalytic activity, a polyalkylene oxide can be efficiently produced. Further, by polymerizing an alkylene oxide using the composition of the present invention, a polyalkylene oxide having a high molecular weight, a low degree of unsaturation and a narrow molecular weight distribution can be produced.

The present invention will be described in detail below.

The composition of the present invention contains an organic base compound having a pK _BH of 23 or more, a Lewis acid, and an active hydrogen-containing compound. In the present invention, "pK _BH " represents the acid dissociation constant of the conjugate acid (BH ⁺ ) produced by the protonation of the organic base compound (B) measured in acetonitrile, and can be calculated by the following formula. ..

In the present invention, the organic base compound is any compound as long as the acid dissociation constant (pK _BH ) of the conjugate acid (BH ⁺ ) produced by protonation of the organic base compound (B) measured in acetonitrile is 23 or more. It may be. When the pK _BH of the organic base compound is less than 23, it becomes difficult to produce a high molecular weight polyoxyalkylene polyol, and it takes a long time to polymerize the alkylene oxide, which makes it difficult to efficiently produce a polyalkylene oxide. It becomes.

In the present invention, examples of the organic base compound having a pK _BH of 23 or more include the following general formula (1).

(In the above general formula (1), R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Here, R ¹ and R ² are bonded to each other. ring structures, may form a ring structure R ¹ s or R ² together are linked together.)
Compound represented by, the following general formula (2)

(In the above general formula (2), R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Here, R ¹ and R ² are bonded to each other. ring structures, may form a ring structure R ¹ s or R ² together are linked together.)
Compound represented by, the following general formula (3)

(In the above general formula (3), R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, where R ¹ , R ² and R ^{3 are used.} two are ring structure connected with each other among the may form a ring structure R ¹ s or R ² together are linked together.)
Compound represented by, the following general formula (4)

(In the above general formula (4), R independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.)
Compound represented by, the following general formula (5)

(In the above general formula (5), n represents an integer of 1 to 3).
Examples thereof include the compounds indicated by, and these can be used alone or in combination of two or more.

In the above general formula (1), R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Here, ring structure R ¹ and R ² are bonded to each other to form a ring structure R ¹ s or R ² together are bonded to each other.

Examples of the hydrocarbon group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a vinyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an allyl group, an n-butyl group, an isobutyl group and a t-butyl group. , Cyclobutyl group, n-pentyl group, neopentyl group, cyclopentyl group, n-hexyl group, cyclohexyl group, phenyl group, heptyl group, cycloheptyl group, octyl group, cyclooctyl group, nonyl group, cyclononyl group, decyl group, Cyclodecyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecil group and the like can be mentioned.

Examples of the case where R ¹ and R ² are bonded to each other to form a ring structure include a pyrrolidinyl group, a pyrrolyl group, a piperidinyl group, an indrill group, an isoindryl group and the like.

Furthermore, as the ring structure R ¹ s or R ² together are linked together, for example, one substituent is an ethylene group, a propylene group, is an alkylene group such as butylene group, ring structure linked together with other substituent Can be mentioned.

Specific examples of the organic base compound represented by the above general formula (1) include 1-tert-butyl-2,2,4,5,4-penta (methylamino) -2λ5,4λ5-catenadi (phosphazene). , 1-tert-butyl-2,2,4,4-penta (ethylamino) -2λ5,4λ5-catenadi (phosphazene), 1-tert-butyl-2,2,4,4-penta (ethylamino) Isopropylamino) -2λ5,4λ5-catenadi (phosphazene), 1-tert-butyl-2,2,4,5,4-pentakis (dimethylamino) -2λ5,4λ5-catenadi (phosphazene), 1-tert-butyl- 2,2,4,5,4-pentakis (diethylamino) -2λ5,4λ5-catenadi (phosphazene), 1-tert-butyl-2,2,4,4,5-pentakis (diisopropylamino) -2λ5,4λ5- Catenadi (phosphazene), 1-ethyl-2,2,4,4,4-pentakis (dimethylamino) -2λ5,4λ5-catenadi (phosphazene), 1-tert-octyl-2,2,4,4,5- Pentakis (dimethylamino) -2λ5,4λ5-catenadi (phosphazene), 1-ethyl-2,2,4,5,4-pentakis (dimethylamino) -2λ5,4λ5-catenadi (phosphazene) and the like can be exemplified. ..

In the above general formula (2), R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Here, ring structure R ¹ and R ² are bonded to each other to form a ring structure R ¹ s or R ² together are bonded to each other.

Examples of the hydrocarbon group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a vinyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an allyl group, an n-butyl group, an isobutyl group and a t-butyl group. , Cyclobutyl group, n-pentyl group, neopentyl group, cyclopentyl group, n-hexyl group, cyclohexyl group, phenyl group, heptyl group, cycloheptyl group, octyl group, cyclooctyl group, nonyl group, cyclononyl group, decyl group, Cyclodecyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecil group and the like can be mentioned.

Examples of the case where R ¹ and R ² are bonded to each other to form a ring structure include a pyrrolidinyl group, a pyrrolyl group, a piperidinyl group, an indrill group, an isoindryl group and the like.

Furthermore, as the ring structure R ¹ s or R ² together are linked together, for example, one substituent is an ethylene group, a propylene group, is an alkylene group such as butylene group, ring structure linked together with other substituent Can be mentioned.

Specific examples of the organic base compound represented by the general formula (2) include 1-tert-butyl-2,2,2-tri (methylamino) phosphazene and 1-tert-butyl-2,2,2. -Tri (ethylamino) phosphazene, 1-tert-butyl-2,2,2-tri (isopropylamino) phosphazene, 1-tert-butyl-2,2,2-tris (dimethylamino) phosphazene, 1-tert- Butyl-2,2,2-tris (diethylamino) phosphazene, 1-tert-butyl-2,2,2-tris (diisopropylamino) phosphazene, 1-ethyl-2,2,2-tris (dimethylamino) phosphazene, 1-tert-octyl-2,2,2-tris (dimethylamino) phosphazene, 1-tert-butyl-2,2,2-tri (pyrrolidino) phosphazene (BTPP), 2-tert-butylimino-2-diethylamino- 1,3-Dimethylperhydro-1,3,2-diazaphosphorin (BEMP) and the like can be exemplified.

In the above general formula (3), R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Here, ^{two of} R ¹ , R ² and R ³ may form a ring structure in which they are bonded to each other, or a ring structure in which R ^{1 and} R ² are bonded to each other.

Examples of the hydrocarbon group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a vinyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an allyl group, an n-butyl group, an isobutyl group and a t-butyl group. , Cyclobutyl group, n-pentyl group, neopentyl group, cyclopentyl group, n-hexyl group, cyclohexyl group, phenyl group, heptyl group, cycloheptyl group, octyl group, cyclooctyl group, nonyl group, cyclononyl group, decyl group, Cyclodecyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecil group and the like can be mentioned.

Specific examples of the organic base compound represented by the general formula (3) include 1,1,3,3-tetramethylguanidine (TMG) and 2-tert-butyl-1,1,3,3-tetra. Methylguanidine (BTMG), 1,8-bis (tetramethylguanidino) naphthalene (TMGN), 1,5,7-triazabicyclo [4.4.0] deca-5-ene (TBD), 7-methyl- Examples include 1,5,7-triazabicyclo [4.4.0] deca-5-ene (MTBD) and the like.

In the above general formula (4), R independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.

Examples of the hydrocarbon group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a vinyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an allyl group, an n-butyl group, an isobutyl group and a t-butyl group. , Cyclobutyl group, n-pentyl group, neopentyl group, cyclopentyl group, n-hexyl group, cyclohexyl group, phenyl group, heptyl group, cycloheptyl group, octyl group, cyclooctyl group, nonyl group, cyclononyl group, decyl group, Cyclodecyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecil group and the like can be mentioned.

Specific examples of the organic base compound represented by the above general formula (4) include 2,8,9-trimethyl 2,5,8,9-tetraaza-1-phosphabicyclo [3.3.3] undecane. , 2,8,9-triethyl 2,5,8,9-tetraaza-1-phosphabicyclo [3.3.3] undecane, 2,8,9-tri (n-propyl) 2,5,8, 9-Tetraaza-1-phosphabicyclo [3.3.3] undecane, 2,8,9-triisopropyl 2,5,8,9-tetraaza-1-phosphabicyclo [3.3.3] undecane, 2,8,9-tri (n-butyl) 2,5,8,9-tetraaza-1-phosphabicyclo [3.3.3] undecane, 2,8,9-triisobutyl 2,5,8, 9-Tetraaza-1-phosphobicyclo [3.3.3] Undecane, 2,8,9-tri (tert-butyl) 2,5,8,9-Tetraaza-1-phospabicyclo [3.3. 3] Undecane and the like can be exemplified.

Specific examples of the organic base compound represented by the general formula (5) include 1,5-diazabicyclo [4.3.0] nona-5-ene (DBN) and 1,8-diazabicyclo [5. 4.0] Undeca-7-en (DBU) and the like can be exemplified.

Among these organic base compounds, 1-tert-butyl-2,2,4,4,5-pentakis (dimethylamino)-because the raw material is easily available and the composition has excellent catalytic performance. 2λ5,4λ5-catenadi (phosphazene), 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorin (BEMP), 1,1,3,3-tetra Methylguanidine (TMG), 7-methyl-1,5,7-triazabicyclo [4.4.0] deca-5-ene (MTBD), 2,8,9-triisopropyl 2,5,8,9 -Tetraaza-1-phosphabicyclo [3.3.3] undecane and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) are particularly preferred.

In the present invention, as the Lewis acid, for example, at least one compound selected from the group consisting of an aluminum compound, a zinc compound, and a boron compound can be mentioned.

Examples of the aluminum compound include trimethylaluminum, triethylaluminum, triisobutylaluminum, trinormalhexylaluminum, triethoxyaluminum, triisopropoxyaluminum, triisobutoxyaluminum, triphenylaluminum, diphenylmonoisobutylaluminum, monophenyldiisobutylaluminum and the like. Organic aluminum; aluminoxane such as methylaluminoxane, isobutylaluminoxane, methyl-isobutylaluminoxan; inorganic aluminum such as aluminum chloride, aluminum hydroxide, aluminum oxide can be mentioned.

Examples of the zinc compound include organic zinc such as dimethyl zinc, diethyl zinc and diphenyl zinc; and inorganic zinc such as zinc chloride and zinc oxide.

Examples of the boron compound include boron trifluoride, boron tribromide, boron triiodide, triethylboron, trimethoxyboron, triethoxyboron, triisopropoxyboron, tri-n-propoxyboron, triphenylboron and tris. (Pentafluorophenyl) boron and the like can be mentioned.

Among these Lewis acids, organoaluminum, aluminoxane, organozinc, and boron compounds are preferable, and organoaluminum is particularly preferable, because the composition has excellent catalytic performance.

In the present invention, examples of the active hydrogen-containing compound include water, a hydroxy compound, an amine compound, a carboxylic acid compound, a thiol compound, and a polyether polyol having a hydroxyl group.

Examples of the hydroxy compound include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, glycerin, and triol. Examples thereof include methylolpropane, hexanetriol, pentaerythritol, diglycerin, sorbitol, shoeclaw, glucose, 2-naphthol, bisphenol and the like.

Examples of the amine compound include ethylenediamine, N, N'-dimethylethylenediamine, piperidine, piperazine and the like.

Examples of the carboxylic acid compound include benzoic acid and adipic acid. Examples of the thiol compound include ethanedithiol and butanedithiol.

Examples of the polyether polyol having a hydroxyl group include a polyether polyol having a molecular weight of 200 to 3000.

Then, these active hydrogen-containing compounds may be used alone or in combination of several kinds.

In the composition of the present invention, the ratio of the organic base compound to the Lewis acid is preferably organic base compound: Lewis acid = 1: 0.002 to 500 (molar ratio), and more preferably organic base compound: Lewis acid =. 1: 0.1 to 10 (molar ratio), particularly preferably an organic base compound: Lewis acid = 1: 0.5 to 5 (molar ratio).

In the composition of the present invention, the ratio of the active hydrogen to the organic base compound in the active hydrogen-containing compound is preferably active hydrogen: organic base compound = 1: 0.001 to 10 (molar ratio) in the active hydrogen-containing compound. , More preferably, active hydrogen in the active hydrogen-containing compound: organic base compound = 1: 0.001 to 1 (molar ratio), particularly preferably, active hydrogen in the active hydrogen-containing compound: organic base compound = 1: 0. It is .001 to 0.1 (molar ratio).

In the composition of the present invention, the ratio of active hydrogen to Lewis acid in the active hydrogen-containing compound is preferably active hydrogen: Lewis acid = 1: 0.001 to 10 (molar ratio) in the active hydrogen-containing compound. Preferably, active hydrogen in the active hydrogen-containing compound: Lewis acid = 1: 0.001 to 1 (molar ratio), and particularly preferably, active hydrogen in the active hydrogen-containing compound: Lewis acid = 1: 0.001 to 0. .1 (molar ratio).

As a method for producing the composition of the present invention, any method can be used as long as the composition of the present invention can be prepared, and the present invention is not particularly limited. For example, a method of mixing an organic base compound, a Lewis acid, and an active hydrogen-containing compound can be mentioned. In that case, for example, benzene, toluene, xylene, cyclohexane, 1,2-dichloroethane, chlorobenzene, dichlorobenzene, 1,4-dioxane, 1,2-dimethoxyethane and the like may be used as the solvent.

Further, among organic base compounds, Lewis acids, and active hydrogen-containing compounds, a method of mixing two components and then mixing the remaining one component to prepare, a method of mixing one component with the remaining two components previously mixed, and the like. Any preparation method may be used. Among them, since the composition has excellent catalytic performance, it is preferable to prepare the composition by mixing the organic base compound and the active hydrogen-containing compound and then mixing with Lewis acid.

When preparing the composition of the present invention, heating / depressurizing treatment or the like may be performed. The temperature of the heat treatment may be, for example, 50 to 150 ° C., preferably 70 to 130 ° C. Further, as the pressure during the depressurization treatment, for example, 50 kPa or less, preferably 20 kPa or less can be mentioned.

Since the composition of the present invention is excellent in catalytic performance, it is useful as a catalyst for producing a polyalkylene oxide.

The method for producing a polyalkylene oxide of the present invention is characterized in that ring-opening polymerization of the alkylene oxide is carried out in the presence of the composition of the present invention described above.

In the method for producing a polyalkylene oxide of the present invention, examples of the alkylene oxide include alkylene oxides having 2 to 20 carbon atoms, and specifically, ethylene oxide, propylene oxide, 1,2-butylene oxide, and 2 , 3-Butylene oxide, Isobutylene oxide, Butadiene monooxide, Pentene oxide, Styrene oxide, Cyclohexene oxide and the like can be mentioned. Among these, ethylene oxide and propylene oxide are preferable because alkylene oxide is easily available and the obtained polyalkylene oxide has a high industrial value. The alkylene oxide may be used alone or in combination of two or more. When two or more kinds are mixed and used, for example, the first alkylene oxide may be reacted and then the second and third alkylene oxides may be reacted, or two or more kinds of alkylene oxides may be reacted at the same time. Is also good.

In the method for producing a polyalkylene oxide of the present invention, the polymerization pressure is preferably in the range of 0.05 to 1.0 MPa, preferably 0.1 to 0.6 MPa. In the method for producing a polyalkylene oxide of the present invention, the polymerization temperature is preferably in the range of 50 to 150 ° C, preferably in the range of 70 to 140 ° C.

In the method for producing a polyalkylene oxide of the present invention, the polymerization can be carried out in a solvent or in a solvent-free environment, and is preferably performed in a solvent-free environment. Examples of the solvent used in the solvent include benzene, toluene, xylene, cyclohexane, 1,2-dichloroethane, chlorobenzene, dichlorobenzene, 1,4-dioxane, 1,2-dimethoxyethane and the like.

In the method for producing a polyalkylene oxide of the present invention, since it is an efficient method for producing a polyalkylene oxide, it is preferable that the catalytic activity is 200 g / mol · min or more, and particularly 300 g / mol · min. It is preferable that the above is shown.

The polyalkylene oxide obtained by the method for producing a polyalkylene oxide of the present invention has a molecular weight of 1000 to 50,000 g / mol calculated from the hydroxyl value calculated by the method described in JIS K-1557 and the number of functional groups thereof. In particular, it preferably has 3000 to 30000 g / mol. Further, the degree of unsaturation calculated by the method described in JIS K-1557 is preferably 0.03 meq / g or less, particularly preferably 0.02 meq / g or less. Further, the molecular weight distribution calculated by gel permeation chromatography (GPC) is preferably 1.3 or less, particularly 1.1 or less.

Hereinafter, the present invention will be described with reference to Examples, but the present invention will not be construed as being limited by the present Examples. First, a method for calculating catalytic activity in the production of a polyalkylene oxide using the composition of the present invention and a method for analyzing the polyalkylene oxide produced by the present invention will be described.

(1) Catalytic activity (unit: g / mol · min)
The amount of the reacted alkylene oxide is a (unit: g), the amount of the organic base compound used is b (unit: mol), the time required for polymerization is c (unit: min), and the catalytic activity is calculated by the following formula. did.
Catalytic activity = a / (b × c)

(2) Molecular weight of polyalkylene oxide (unit: g / mol)
The hydroxyl value d (unit: mgKOH / g) of the polyalkylene oxide was measured by the method described in JIS K-1557. The number of functional groups of the obtained polyalkylene oxide was defined as e, and the molecular weight of the polyalkylene oxide was calculated by the following formula.
Molecular weight = (56100 / d) x e
(3) Degree of unsaturation of polyalkylene oxide (unit: meq / g)
The degree of unsaturation of the polyalkylene oxide was calculated by the method described in JIS K-1557.

(4) Molecular weight distribution of polyalkylene oxide (unit: none)
Gel permeation chromatograph (GPC) (manufactured by Toso Co., Ltd., (trade name) HLC8020), polystyrene was used as the standard substance, and tetrahydrofuran was used as the solvent, and the measurement was performed at 40 ° C., and the number average molecular weight of the polyalkylene oxide ( Mn), weight average molecular weight (Mw), and molecular weight distribution (Mw / Mn) were calculated.

Example 1.
A polyether polyol having a molecular weight of 1000 having three hydroxyl groups as an active hydrogen-containing compound in a 0.2 liter autoclave equipped with a stirring blade (manufactured by Sanyo Kasei Kogyo Co., Ltd. (trade name) Sanniks GP1000; hydroxyl value 160 mgKOH / g) 18 g (18 mmol, amount of active hydrogen 54 mmol), and 1-tert-butyl-2,2,4,5,4-pentakis (dimethylamino) -2λ5,4λ5-catenadi (phosphazene) corresponding to the above general formula (1). [Organic base compound A, pK _BH = 33.5] 99 mg (0.27 mmol, 0.005 mol with respect to 1 mol of active hydrogen) was added. After setting the inside of the autoclave to a nitrogen atmosphere, the inside temperature was set to 80 ° C., and dehydration treatment was performed under a reduced pressure of 0.5 kPa. Then, 0.54 ml (0.54 mmol, 2 mol with respect to 1 mol of the organic base compound A, 0.010 mol with respect to 1 mol of active hydrogen) of a 1.0 mol / L hexane solution of triisobutylaluminum (TIBAL) was added. The internal temperature was set to 80 ° C., and a reduced pressure treatment of 0.5 kPa was performed to obtain the composition of the present invention.

In the presence of the obtained composition, the internal temperature of the autoclave was set to 90 ° C., and 110 g of propylene oxide was intermittently supplied so as to maintain the reaction pressure of 0.3 MPa or less while reacting in the internal temperature range of 88 to 92 ° C. It was. Then, the residual propylene oxide was removed under a reduced pressure of 0.5 kPa to obtain 126 g of colorless and odorless polyalkylene oxide. The catalytic activity was 630 g / mol · min, the obtained polyalkylene oxide had a molecular weight of 7000 g / mol, the degree of unsaturation was 0.006 meq / g, and the molecular weight distribution was 1.05. The results are shown in Table 1.

Example 2.
A 0.2 liter autoclave equipped with a stirring blade and a polyether polyol having a molecular weight of 1000 having three hydroxyl groups as an active hydrogen-containing compound (manufactured by Sanyo Kasei Kogyo Co., Ltd. (trade name) Sanniks GP1000; hydroxyl value 160 mgKOH / g) 18 g (18 mmol, amount of active hydrogen 54 mmol), and 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorin corresponding to the above general formula (2) [organic] Basic compound B, pK _BH = 27.6] 74 mg (0.27 mmol, 0.005 mol with respect to 1 mol of active hydrogen) was added. After setting the inside of the autoclave to a nitrogen atmosphere, the inside temperature was set to 80 ° C., and dehydration treatment was performed under a reduced pressure of 0.5 kPa. Then, 0.54 ml (0.54 mmol, 2 mol with respect to 1 mol of the organic base compound B, 0.020 mol with respect to 1 mol of active hydrogen) of a 1.0 mol / L hexane solution of triisobutylaluminum (TIBAL) was added, and the internal temperature was increased. Was heated to 80 ° C. and subjected to a reduced pressure treatment of 0.5 kPa to obtain the composition of the present invention.

In the presence of the obtained composition, the internal temperature of the autoclave was set to 90 ° C., and 110 g of propylene oxide was intermittently supplied so as to maintain the reaction pressure of 0.3 MPa or less while reacting in the internal temperature range of 88 to 92 ° C. It was. Then, the residual propylene oxide was removed under a reduced pressure of 0.5 kPa to obtain 125 g of colorless and odorless polyalkylene oxide. The catalytic activity was 550 g / mol · min, the molecular weight of the obtained polyalkylene oxide was 7000 g / mol, the degree of unsaturation was 0.005 meq / g, and the molecular weight distribution was 1.05. The results are also shown in Table 1.

Example 3.
A 0.2 liter autoclave equipped with a stirring blade and a polyether polyol having a molecular weight of 1000 having three hydroxyl groups as an active hydrogen-containing compound (manufactured by Sanyo Kasei Kogyo Co., Ltd. (trade name) Sanniks GP1000; hydroxyl value 160 mgKOH / g) 18 g (18 mmol, amount of active hydrogen 54 mmol), and 7-methyl-1,5,7-triazabicyclo [4.4.0] deca-5-ene [organic base compound C] corresponding to the above general formula (3). , PK _BH = 25.5] 41 mg (0.27 mmol, 0.005 mol with respect to 1 mol of active hydrogen) was added. After setting the inside of the autoclave to a nitrogen atmosphere, the inside temperature was set to 80 ° C., and dehydration treatment was performed under a reduced pressure of 0.5 kPa. Then, 0.81 ml (0.81 mmol, 3 mol with respect to 1 mol of the organic base compound C, 0.015 mol with respect to 1 mol of active hydrogen) of a 1.0 mol / L hexane solution of triisobutylaluminum (TIBAL) was added, and the internal temperature was increased. Was heated to 80 ° C. and subjected to a reduced pressure treatment of 0.5 kPa to obtain the composition of the present invention.

In the presence of the obtained composition, the internal temperature of the autoclave was set to 80 ° C., and 92 g of propylene oxide was intermittently supplied so as to maintain the reaction pressure of 0.3 MPa or less while reacting in the internal temperature range of 88 to 92 ° C. It was. Next, after removing residual propylene oxide under a reduced pressure of 0.5 kPa, 18 g of ethylene oxide was intermittently supplied so as to maintain a reaction pressure of 0.25 MPa or less, and the reaction was carried out in an internal temperature range of 108 to 112 ° C. It was. Residual ethylene oxide was removed under a reduced pressure of 0.5 kPa to obtain 126 g of colorless and odorless polyalkylene oxide. The catalytic activity was 580 g / mol · min, the molecular weight of the obtained polyalkylene oxide was 6900 g / mol, the degree of unsaturation was 0.006 meq / g, and the molecular weight distribution was 1.06. The results are also shown in Table 1.

Example 4.
A 0.2 liter autoclave equipped with a stirring blade and a polyether polyol having a molecular weight of 1000 having three hydroxyl groups as an active hydrogen-containing compound (manufactured by Sanyo Kasei Kogyo Co., Ltd. (trade name) Sanniks GP1000; hydroxyl value 160 mgKOH / g) 9 g (9 mmol, amount of active hydrogen 27 mmol), and 2,8,9-triisopropyl 2,5,8,9-tetraaza-1-phosphabicyclo [3.3.3] corresponding to the above general formula (4). 81 mg (0.27 mmol, 0.010 mol with respect to 1 mol of active hydrogen) of undecane [organic base compound D, pK _BH = 32.9] was added. After setting the inside of the autoclave to a nitrogen atmosphere, the inside temperature was set to 80 ° C., and dehydration treatment was performed under a reduced pressure of 0.5 kPa. Then, 0.81 ml (0.81 mmol, 3 mol with respect to 1 mol of the organic base compound D, 0.030 mol with respect to 1 mol of active hydrogen) of a 1.0 mol / L hexane solution of triisobutylaluminum (TIBAL) was added, and the internal temperature was increased. Was heated to 80 ° C. and subjected to a reduced pressure treatment of 0.5 kPa to obtain the composition of the present invention.

In the presence of the obtained composition, the internal temperature of the autoclave was set to 90 ° C., and 138 g of propylene oxide was intermittently supplied so as to maintain the reaction pressure of 0.3 MPa or less while reacting in the internal temperature range of 88 to 92 ° C. It was. Next, after removing residual propylene oxide under a reduced pressure of 0.5 kPa, 27 g of ethylene oxide was intermittently supplied so as to maintain a reaction pressure of 0.25 MPa or less, and the reaction was carried out in an internal temperature range of 108 to 112 ° C. It was. Residual ethylene oxide was removed under a reduced pressure of 0.5 kPa to obtain 170 g of colorless and odorless polyalkylene oxide. The catalytic activity was 490 g / mol · min, the molecular weight of the obtained polyalkylene oxide was 18000 g / mol, the degree of unsaturation was 0.008 meq / g, and the molecular weight distribution was 1.09. The results are also shown in Table 1.

Reference example 5.
A 0.2 liter autoclave equipped with a stirring blade and a polyether polyol having a molecular weight of 1000 having three hydroxyl groups as an active hydrogen-containing compound (manufactured by Sanyo Kasei Kogyo Co., Ltd. (trade name) Sanniks GP1000; hydroxyl value 160 mgKOH / g) 18 g (18 mmol, amount of active hydrogen 54 mmol), and 1,8-diazabicyclo [5.4.0] undec-7-ene [organic base compound E, pK _BH = 24.3] corresponding to the above general formula (5). 82 mg (0.54 mmol, 0.010 mol with respect to 1 mol of active hydrogen) was added. After setting the inside of the autoclave to a nitrogen atmosphere, the inside temperature was set to 80 ° C., and dehydration treatment was performed under a reduced pressure of 0.5 kPa. Then, 1.08 ml (1.08 mmol, 2 mol with respect to 1 mol of the organic base compound E, 0.020 mol with respect to 1 mol of active hydrogen) of a 1.0 mol / L hexane solution of triisobutylaluminum (TIBAL) was added, and the internal temperature was increased. Was heated to 80 ° C. and subjected to a reduced pressure treatment of 0.5 kPa to obtain the composition of the present invention.

In the presence of the obtained composition, the internal temperature of the autoclave was set to 90 ° C., and 92 g of propylene oxide was intermittently supplied so as to maintain the reaction pressure of 0.3 MPa or less while reacting in the internal temperature range of 88 to 92 ° C. It was. Next, after removing residual propylene oxide under a reduced pressure of 0.5 kPa, 18 g of ethylene oxide was intermittently supplied so as to maintain a reaction pressure of 0.25 MPa or less, and the reaction was carried out in an internal temperature range of 108 to 112 ° C. It was. Residual ethylene oxide was removed under a reduced pressure of 0.5 kPa to obtain 125 g of colorless and odorless polyalkylene oxide. The catalytic activity was 510 g / mol · min, the obtained polyalkylene oxide had a molecular weight of 6900 g / mol, the degree of unsaturation was 0.007 meq / g, and the molecular weight distribution was 1.07. The results are also shown in Table 1.

Example 6.
A 0.2 liter autoclave equipped with a stirring blade and a polyether polyol having a molecular weight of 1000 having three hydroxyl groups as an active hydrogen-containing compound (manufactured by Sanyo Kasei Kogyo Co., Ltd. (trade name) Sanniks GP1000; hydroxyl value 160 mgKOH / g) 18 g (18 mmol, amount of active hydrogen 54 mmol), and 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorin corresponding to the above general formula (2) [organic] Basic compound B, pK _BH = 27.6] 74 mg (0.27 mmol, 0.005 mol with respect to 1 mol of active hydrogen) was added. After setting the inside of the autoclave to a nitrogen atmosphere, the inside temperature was set to 80 ° C., and dehydration treatment was performed under a reduced pressure of 0.5 kPa. Thereafter, 1.0 mol / L hexane solution 0.54 ml (0.54 mmol of triisopropoxyaluminum _{^{[Al (O i Pr) 3}} ], an organic base compound B: 0 2 mol, relative to active hydrogen 1mol against 1mol. 010 mol) was added, the internal temperature was set to 80 ° C., and a reduced pressure treatment of 0.5 kPa was performed to obtain the composition of the present invention.

In the presence of the obtained composition, the internal temperature of the autoclave was set to 90 ° C., and 92 g of propylene oxide was intermittently supplied so as to maintain the reaction pressure of 0.3 MPa or less while reacting in the internal temperature range of 88 to 92 ° C. It was. Next, after removing residual propylene oxide under a reduced pressure of 0.5 kPa, 18 g of ethylene oxide was intermittently supplied so as to maintain a reaction pressure of 0.25 MPa or less, and the reaction was carried out in an internal temperature range of 108 to 112 ° C. It was. Residual ethylene oxide was removed under a reduced pressure of 0.5 kPa to obtain 126 g of colorless and odorless polyalkylene oxide. The catalytic activity was 690 g / mol · min, the obtained polyalkylene oxide had a molecular weight of 7000 g / mol, the degree of unsaturation was 0.006 meq / g, and the molecular weight distribution was 1.06. The results are shown in Table 2.

Example 7.
A 0.2 liter autoclave equipped with a stirring blade and a polyether polyol having a molecular weight of 600 having three hydroxyl groups as an active hydrogen-containing compound (manufactured by Sanyo Kasei Kogyo Co., Ltd. (trade name) Sanniks GP600; hydroxyl value 280 mgKOH / g) 11 g (18 mmol, amount of active hydrogen 54 mmol), and 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorin corresponding to the above general formula (2) [organic] Basic compound B, pK _BH = 27.6] 74 mg (0.27 mmol, 0.005 mol with respect to 1 mol of active hydrogen) was added. After setting the inside of the autoclave to a nitrogen atmosphere, the inside temperature was set to 80 ° C., and dehydration treatment was performed under a reduced pressure of 0.5 kPa. Then, 0.81 ml (0.81 mmol, 3 mol with respect to 1 mol of the organic base compound B, 1 mol of active hydrogen) of a 1.0 mol / L hexane solution of aluminoxane having a methyl group and an isobutyl group (MMAO-3A manufactured by Toso Finechem) was used. 0.015 mol) was added thereto, the internal temperature was adjusted to 80 ° C., and a reduced pressure treatment of 0.5 kPa was carried out to obtain the composition of the present invention.

In the presence of the obtained composition, the internal temperature of the autoclave was set to 110 ° C., and 99 g of propylene oxide was intermittently supplied so as to maintain the reaction pressure of 0.3 MPa or less while reacting in the internal temperature range of 108 to 112 ° C. It was. Next, after removing residual propylene oxide under a reduced pressure of 0.5 kPa, 18 g of ethylene oxide was intermittently supplied so as to maintain a reaction pressure of 0.25 MPa or less, and the reaction was carried out in an internal temperature range of 128 to 132 ° C. It was. Residual ethylene oxide was removed under a reduced pressure of 0.5 kPa to obtain 127 g of colorless and odorless polyalkylene oxide. The catalytic activity was 970 g / mol · min, the obtained polyalkylene oxide had a molecular weight of 7000 g / mol, the degree of unsaturation was 0.009 meq / g, and the molecular weight distribution was 1.08. The results are also shown in Table 2.

Example 8.
A 0.2 liter autoclave equipped with a stirring blade and a polyether polyol having a molecular weight of 400 having three hydroxyl groups as an active hydrogen-containing compound (manufactured by Sanyo Kasei Kogyo Co., Ltd. (trade name) Sanniks GP400; hydroxyl value 420 mgKOH / g) 7.2 g (18 mmol, active hydrogen amount 54 mmol), and 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorin corresponding to the above general formula (2). [Organic base compound B, pK _BH = 27.6] 74 mg (0.27 mmol, 0.005 mol with respect to 1 mol of active hydrogen) was added. After setting the inside of the autoclave to a nitrogen atmosphere, the inside temperature was set to 80 ° C., and dehydration treatment was performed under a reduced pressure of 0.5 kPa. Then, 0.54 ml (0.54 mmol, 2 mol with respect to 1 mol of the organic base compound B, 0.010 mol with respect to 1 mol of active hydrogen) of a 1.0 mol / L hexane solution of diethylzinc (ZnEt2) was added, and the internal temperature was adjusted. The temperature was 80 ° C., and the pressure was reduced to 0.5 kPa to obtain the composition of the present invention.
In the presence of the obtained composition, the internal temperature of the autoclave was set to 110 ° C., and 103 g of propylene oxide was intermittently supplied so as to maintain the reaction pressure of 0.3 MPa or less while reacting in the internal temperature range of 108 to 112 ° C. It was. Next, after removing residual propylene oxide under a reduced pressure of 0.5 kPa, 18 g of ethylene oxide was intermittently supplied so as to maintain a reaction pressure of 0.25 MPa or less, and the reaction was carried out in an internal temperature range of 128 to 132 ° C. It was. Residual ethylene oxide was removed under a reduced pressure of 0.5 kPa to obtain 125 g of colorless and odorless polyalkylene oxide. The catalytic activity was 430 g / mol · min, the obtained polyalkylene oxide had a molecular weight of 6900 g / mol, the degree of unsaturation was 0.007 meq / g, and the molecular weight distribution was 1.07. The results are also shown in Table 2.

Example 9.
A 0.2 liter autoclave equipped with a stirring blade and a polyether polyol having a molecular weight of 250 having three hydroxyl groups as an active hydrogen-containing compound (manufactured by Sanyo Kasei Kogyo Co., Ltd. (trade name) Sanniks GP250; hydroxyl value 670 mgKOH / g) 4.5 g (18 mmol, amount of active hydrogen 54 mmol), and 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorin corresponding to the above general formula (2). [Organic base compound B, pK _BH = 27.6] 74 mg (0.27 mmol, 0.005 mol with respect to 1 mol of active hydrogen) was added. After setting the inside of the autoclave to a nitrogen atmosphere, the inside temperature was set to 80 ° C., and dehydration treatment was performed under a reduced pressure of 0.5 kPa. Then, 0.54 ml (0.54 mmol, 2 mol with respect to 1 mol of the organic base compound B, 0.010 mol with respect to 1 mol of active hydrogen) of a 1.0 mol / L hexane solution of triethylborane (BEt3) was added, and the internal temperature was adjusted. The temperature was 80 ° C., and the pressure was reduced to 0.5 kPa to obtain the composition of the present invention.

In the presence of the obtained composition, the internal temperature of the autoclave was set to 110 ° C., and 106 g of propylene oxide was intermittently supplied so as to maintain the reaction pressure of 0.3 MPa or less while reacting in the internal temperature range of 108 to 112 ° C. It was. Next, after removing residual propylene oxide under a reduced pressure of 0.5 kPa, 18 g of ethylene oxide was intermittently supplied so as to maintain a reaction pressure of 0.25 MPa or less, and the reaction was carried out in an internal temperature range of 128 to 132 ° C. It was. Residual ethylene oxide was removed under a reduced pressure of 0.5 kPa to obtain 126 g of colorless and odorless polyalkylene oxide. The catalytic activity was 540 g / mol · min, the molecular weight of the obtained polyalkylene oxide was 6900 g / mol, the degree of unsaturation was 0.008 meq / g, and the molecular weight distribution was 1.07. The results are also shown in Table 2.

Comparative example 1.
A 0.2 liter autoclave equipped with a stirring blade and a polyether polyol having a molecular weight of 1000 having three hydroxyl groups as an active hydrogen-containing compound (manufactured by Sanyo Kasei Kogyo Co., Ltd. (trade name) Sanniks GP1000; hydroxyl value 160 mgKOH / g) 18 g (18 mmol, amount of active hydrogen 54 mmol), and 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorin corresponding to the above general formula (2) [organic] Basic compound B, pK _BH = 27.6] 74 mg (0.27 mmol, 0.005 mol with respect to 1 mol of active hydrogen) was added. After the inside of the autoclave had a nitrogen atmosphere and the inside of the autoclave had a nitrogen atmosphere, the autoclave was dehydrated under a reduced pressure of 0.5 kPa at an internal temperature of 80 ° C.

The internal temperature of the autoclave was 90 ° C., and the reaction was carried out in the internal temperature range of 88 to 92 ° C. while intermittently supplying propylene oxide so as to maintain the reaction pressure of 0.3 MPa or less. As a result, the reaction was stopped when 10 g of propylene oxide was supplied. Residual propylene oxide was removed under a reduced pressure of 0.5 kPa to obtain 19 g of colorless and odorless polyalkylene oxide. The catalytic activity was 26 g / mol · min, the molecular weight of the obtained polyalkylene oxide was 1100 g / mol, the degree of unsaturation was 0.011 meq / g, and the molecular weight distribution was 1.05. The results are shown in Table 3.

Comparative example 2.
A 0.2 liter autoclave equipped with a stirring blade and a polyether polyol having a molecular weight of 1000 having three hydroxyl groups as an active hydrogen-containing compound (manufactured by Sanyo Kasei Kogyo Co., Ltd. (trade name) Sanniks GP1000; hydroxyl value 160 mgKOH / g) 18 g (18 mmol, 54 mmol of active hydrogen) and 0.54 ml (0.54 mmol, 0.010 mol per 1 mol of active hydrogen) of a 1.0 mol / L hexane solution of triisobutylaluminum (TIBAL) were added. After setting the inside of the autoclave to a nitrogen atmosphere, the inside temperature was set to 80 ° C., and dehydration treatment was performed under a reduced pressure of 0.5 kPa.

The internal temperature of the autoclave was 90 ° C., and the reaction was carried out in the internal temperature range of 88 to 92 ° C. while intermittently supplying propylene oxide so as to maintain the reaction pressure of 0.3 MPa or less. As a result, the reaction was stopped when 9 g of propylene oxide was supplied. As a result of removing residual propylene oxide under a reduced pressure of 0.5 kPa, a raw material, a polyether polyol (manufactured by Sanyo Chemical Industries, Ltd., Sanniks GP1000) was recovered. The results are also shown in Table 3.

Comparative example 3.
A 0.2 liter autoclave equipped with a stirring blade and a polyether polyol having a molecular weight of 1000 having three hydroxyl groups as an active hydrogen-containing compound (manufactured by Sanyo Kasei Kogyo Co., Ltd. (trade name) Sanniks GP1000; hydroxyl value 160 mgKOH / g) 18 g (18 mmol, amount of active hydrogen 54 mmol) and 27 mg (0.27 mmol, 0.005 mol with respect to 1 mol of active hydrogen) of triethylamine [organic base compound F, pK _BH = 18.5] were added. After setting the inside of the autoclave to a nitrogen atmosphere, the inside temperature was set to 80 ° C., and dehydration treatment was performed under a reduced pressure of 0.5 kPa. Then, 0.54 ml (0.54 mmol, 2 mol with respect to 1 mol of the organic base compound F, 0.010 mol with respect to 1 mol of active hydrogen) of a 1.0 mol / L hexane solution of triisobutylaluminum (TIBAL) was added, and the internal temperature was increased. Was 80 ° C., and a reduced pressure treatment of 0.5 kPa was performed.

The internal temperature of the autoclave was 90 ° C., and the reaction was carried out in the internal temperature range of 88 to 92 ° C. while intermittently supplying propylene oxide so as to maintain the reaction pressure of 0.3 MPa or less. As a result, the reaction was stopped when 9 g of propylene oxide was supplied. As a result of removing residual propylene oxide under a reduced pressure of 0.5 kPa, a raw material, a polyether polyol (manufactured by Sanyo Chemical Industries, Ltd., Sanniks GP1000) was recovered. The results are also shown in Table 3.

By using the composition of the present invention, a polyalkylene oxide can be efficiently produced. The obtained polyalkylene oxide is useful as a polyurethane raw material, a polyester raw material, a surfactant raw material, a lubricant raw material and the like. In particular, by reacting with various isocyanate compounds, hard foam used for heat insulating materials, soft foam used for automobile seats / cushions, bedding, etc., adhesives, paints, sealants, thermosetting elastomers, thermoplastics, etc. Expected to develop into elastomers.

Claims (8)

pK _BH is 25.5 or more organic basic compounds, Lewis acids, and looking containing an active hydrogen containing compound, an organic base compound of _{pK BH} is 25.5 or higher, the following general formula (1)
(In the above general formula (1), R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Here, R ¹ and R ² are bonded to each other. ring structures, may form a ring structure R ¹ s or R ² together are linked together.)
Compound represented by, the following general formula (2)
(In the above general formula (2), R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Here, R ¹ and R ² are bonded to each other. ring structures, may form a ring structure R ¹ s or R ² together are linked together.)
Compound represented by, the following general formula (3)
(In the above general formula (3), R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, where R ¹ , R ² and R ^{3 are used.} two are ring structure connected with each other among the may form a ring structure R ¹ s or R ² together are linked together.)
The compound represented by, and the following general formula (4)
(In the above general formula (4), R independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.)
A composition characterized by being at least one compound selected from the group consisting of the compounds represented by . The composition according to claim 1, wherein the Lewis acid is at least one compound selected from the group consisting of an aluminum compound, a zinc compound, and a boron compound. According to claim 1 or 2 , the ratio of the organic base compound having a pK _BH of 25.5 or more to Lewis acid is organic base compound: Lewis acid = 1: 0.002 to 500 (molar ratio). The composition described. The ratio of active hydrogen in the active hydrogen-containing compound to the organic base compound having a pK _BH of 25.5 or more is active hydrogen in the active hydrogen-containing compound: organic base compound = 1: 0.001 to 10 (molar ratio). The composition according to any one of claims 1 to 3 , wherein the composition is characterized by the above. Claims 1 to 1, wherein the ratio of active hydrogen to Lewis acid in the active hydrogen-containing compound is active hydrogen: Lewis acid = 1: 0.001 to 10 (molar ratio) in the active hydrogen-containing compound. The composition according to any one of claims 4 . The method for producing a composition according to any one of claims 1 to 5 , wherein an organic base compound having a pK _BH of 25.5 or more and an active hydrogen-containing compound are mixed, and then Lewis acid is mixed. An alkylene oxide polymerization catalyst comprising the composition according to any one of claims 1 to 5 . A method for producing a polyalkylene oxide, which comprises performing ring-opening polymerization of an alkylene oxide in the presence of the composition according to any one of claims 1 to 5 .