Polyalkylene glycol producing catalyst, and method for producing polyalkylene glycol using same

A technology for polyalkylene glycol and manufacturing method, applied in chemical instruments and methods, organic chemistry, compounds of elements of Group 5/15 of the periodic table, etc. Shows the problems of preparing polyalkylene polyols, etc., to achieve the effect of no residual odor, low total unsaturation, and narrow molecular weight distribution

Active Publication Date: 2011-08-31
TOSOH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, Patent Document 8 does not show an example of preparing polyalkylene polyols, so it is completely unclear how to prepare polyalkylene polyols using the nitrogen-containing phosphonium salt of the above formula (III), and what kind of polyalkylene polyols can be prepared thereby. polyalkylene polyol

Method used

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  • Polyalkylene glycol producing catalyst, and method for producing polyalkylene glycol using same
  • Polyalkylene glycol producing catalyst, and method for producing polyalkylene glycol using same
  • Polyalkylene glycol producing catalyst, and method for producing polyalkylene glycol using same

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Embodiment

[0133] Next, the present invention will be described in more detail by way of examples, but the present invention should not be limitedly interpreted as the following examples. In addition, in the following examples, NMR spectrum, GC-MS, and hydroxyl value were measured as follows.

[0134] Determination of NMR spectrum:

[0135] Measurement was performed using a nuclear magnetic resonance spectrometer (manufactured by JEOL Ltd., trade name: GSX270WB), using tetramethylsilane (TMS) as an internal standard and deuterated chloroform as a deuterated solvent.

[0136] Determination of number average molecular weight:

[0137]Using gel permeation chromatography (GPC) (manufactured by Tosoh Corporation, trade name: HLC 8020GPC), the measurement was performed using tetrahydrofuran as a solvent, and the dissolution curve measured at 40° C. was used as a standard polystyrene-equivalent value.

[0138] GC-MS determination:

[0139] Using a gas chromatography-mass spectrometer (manufa...

Synthetic example 1

[0149] Tetrakis(tetramethylguanidino)phosphonium chloride was synthesized as follows: [(Me 2 N) 2 C=N] 4 P + Cl - (In the formula, Me represents a methyl group. The same applies to the following.).

[0150] Take 4.01g (10.0mmol) of phosphorus pentachloride to a 300ml four-neck flask equipped with a thermometer, dropping funnel, condenser tube and magnetic rotor, and add 60ml of dehydrated toluene (manufactured by Wako Pure Chemicals) to prepare slurry solution. The slurry solution was immersed in a cooling bath cooled to -30°C with dry ice-acetone to lower the internal temperature to -30°C, and then 22.2 g was added dropwise from the dropping funnel over 1 hour under vigorous stirring. (20 mmol) of 1,1,3,3-tetramethylguanidine. After stirring at -30°C for 1 hour, the cooling bath was removed and the temperature was slowly raised to room temperature. Furthermore, this slurry solution was heated at 100 degreeC for 10 hours, and the white slurry solution was obtained. Aft...

Synthetic example 2

[0160] Tetrakis(tetramethylguanidino)phosphonium hydroxide was synthesized as follows: [(Me 2 N) 2 C=N] 4 P + Oh - .

[0161] 3.2 g (6 mmol) of tetrakis[(dimethylamino)imino]phosphonium chloride was dissolved in 100 ml of ion-exchanged water to prepare a 0.06 mol / L solution. This solution was passed through a column (30 mm in diameter, 600 mm in height) filled with 100 ml of hydroxyl-type anion exchange resin (manufactured by Organo Corporation, amberlite IRA410 OH) at room temperature at a flow rate of 300 ml / hour, and then 150 ml of ion exchange resin was passed through at the same flow rate. water. After the effluent was concentrated, it was dried at 40°C and 1mmHg to obtain 3.1g of tetrakis(tetramethylguanidino)phosphonium hydroxide: [(Me 2 N) 2 C=N] 4 P + Oh - of white crystals. The yield is 99%.

[0162] 1 H-NMR measurement result (deuterated solvent: CDCl 3 , internal standard: tetramethylsilane):

[0163] Chemical shift: 2.83 ppm (methyl).

[0164] GC-M...

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Abstract

Disclosed is a catalyst composed of a salt of a phosphazenium cation and an active hydrogen compound anion, which can be easily synthesized, does not contain metal components at all, and does not leave any odor on a resulting product. Also disclosed are a method for producing the catalyst and a method for economically and efficiently producing a polyalkylene oxide using the catalyst. Specifically, a salt of a phosphazenium cation and an active hydrogen compound anion, which is represented by general formula (2), is used as a polyalkylene glycol producing catalyst. (In general formula (2), R1 and R2 each independently represents an alkyl group having 1-10 carbon atoms, an unsubstituted or substituted phenyl group having 6-10 carbon atoms, or an unsubstituted or substituted phenylalkyl group having 6-10 carbon atoms, provided that R1 and R2 or R2's may combine together to form a ring structure; n represents a real number of 1-8; and Yn- represents an anion of an active hydrogen compound which is obtained by removing n protons from an active hydrogen compound Y).

Description

technical field [0001] The present invention relates to a catalyst for the economical production of polyalkylene glycols by ring-opening polymerization of alkylene oxides. Polyalkylene oxides are important polymers used as raw materials for polyurethane foams, elastomers, etc., or surfactants, etc., by reacting with isocyanate compounds. Background technique [0002] As catalysts for producing polyalkylene oxides by ring-opening polymerization of alkylene oxides, there are known, for example, active hydrogen compounds and Zn 3 [Fe(CN) 6 ] 2 ·H 2 A compound represented by O·dioxane (for example, refer to Patent Document 1). In addition, it is known that a zinc hexacyanocobaltate complex can be used as a catalyst (for example, refer to Patent Document 2). Furthermore, as a catalyst, it is known to use a product obtained by adding a hexane solution of diethylzinc to a dispersion obtained by adding 1,4-butanediol and It is obtained using a nonionic surfactant (for example,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/10C08G65/28
CPCC08G65/10C08G65/2672C08G65/2675C07F9/5355
Inventor 山本敏秀井上善彰
Owner TOSOH CORP
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