JP2005305280A - Alkoxylation reaction catalyst - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To produce an alkoxylation catalyst which has high activity and can be used for producing an alkylene oxide adduct to an aliphatic alcohol, which has a narrow molecular weight distribution, and to provide the alkylene oxide adduct to the aliphatic alcohol produced by using the alkoxylation catalyst. <P>SOLUTION: This alkoxylation catalyst to be used for reacting the aliphatic alcohol (B) with the alkylene oxide (C) is one or more selected from organometallic compounds shown by the formula: M[RfSO<SB>3</SB>]<SB>n</SB>(wherein M is an element selected from Cu, Cd, Ti, Hf, Cr, Mo, Mn, Fe, Pd and rare-earth metals; (n) is an integer equal to the valence of M; Rf is a 1-16C perfluoroalkyl group). <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a method for producing an alkylene oxide adduct of an aliphatic alcohol. More specifically, the present invention relates to a catalyst for addition polymerization of an alkylene oxide to an aliphatic alcohol and a method for producing an alkylene oxide adduct.

  Addition polymers obtained by addition polymerization of an alkylene oxide to an organic compound containing an active hydrogen atom such as an aliphatic alcohol in the presence of a basic catalyst or an acidic catalyst are known as raw materials for various chemicals. As the basic catalyst, alkali metal oxides such as sodium hydroxide and potassium hydroxide, composite metal oxides, and amines such as diethylamine and triethylamine are usually used. Moreover, as an acid catalyst, mineral acids, such as a sulfuric acid, hydrochloric acid, and phosphoric acid, and its metal salt are used normally.

  When an aliphatic alcohol alkylene oxide adduct is produced using these acid or basic catalysts, an unreacted raw material, for example, an active hydrogen atom-containing organic compound such as an aliphatic alcohol remains in the reaction product. There is a problem that the addition oxyalkylene distribution of the addition polymer obtained by the reaction is not normally dispersed normally but dispersed broadly. When these alkylene oxide adducts are used as a surfactant or the like, there are problems such as an odor caused by residual alcohol and a surfactant function not sufficiently developed due to the broad molecular weight.

Regarding the oxyalkylene group addition number distribution state of the aliphatic alcohol alkylene oxide adduct, the distribution constant c of the following formula (2) derived from the Weibull distribution rule is defined as a narrowing degree index. The smaller the distribution constant c, that is, the smaller the content of unreacted aliphatic alcohol, the narrower the molecular weight distribution.
c = (v + n ₀ / n ₀₀ −1) / [Ln (n ₀₀ / n ₀ ) + n ₀ / n ₀₀ −1] (2)
In these formulas, Ln (n ₀₀ / n ₀ ) means the natural logarithm of (n ₀₀ / n ₀ ), v represents the average number of moles of alkylene oxide added per mole of aliphatic alcohol, and n ₀₀ represents the number of moles of the aliphatic alcohol used in the reaction, and n ₀ represents the number of moles of the unreacted aliphatic alcohol. This formula is applied when the amount of unreacted aliphatic alcohol is not less than the detection limit (0.001% by mass).
In the production method using an alkali metal oxide such as potassium hydroxide, c of the obtained alkylene oxide adduct is 5 or more. Even when the composite metal oxide is used as an alkoxylation catalyst, c of the alkylene oxide adduct does not become 1 or less. (See Patent Documents 1 and 2) In order to reduce c to 1 or less, a method using perchlorates as a catalyst for addition of alkylene oxide has been proposed. (See Patent Document 3)

Japanese Patent Laid-Open No. 1-164437 JP-A-3-242242 US Pat. No. 4,112,231

  However, in the above production method, c is 1 or less. However, when the reaction activity of the catalyst is small and the reaction time is long and the reaction time is shortened by increasing the amount of the catalyst, the product is remarkably colored, There are problems such as deteriorating the appearance and increasing the aldehyde content of the product.

As a result of intensive studies on the above problems, the present inventors have found that when perfluoroalkylsulfonic acid metal salt is used as an alkoxylation catalyst, high activity, short reaction time, and addition polymerization of a high mole number alkylene oxide to an aliphatic alcohol. The inventors have found that an alkylene oxide adduct of an aliphatic alcohol having a narrower molecular weight distribution (the above distribution constant c is less than 0.7) can be obtained, and the present invention has been completed.
That is, the present invention
(I) Alkoxylation of aliphatic alcohol (B) and alkylene oxide (C), characterized by comprising one or more of the organometallic salts (A) represented by the following general formula (1) Reaction catalyst M [RfSO ₃ ] _n (1)
[Wherein M is copper (Cu), cadmium (Cd), titanium (Ti), hafnium (Hf), chromium (Cr), molybdenum (Mo), manganese (Mn), iron (Fe), palladium (Pd) And n represents an integer value equal to the valence of the M element. Rf represents a perfluoroalkyl group having 1 to 16 carbon atoms. ];
(II) Production of an aliphatic alcohol alkylene oxide adduct characterized by adding (C) to (B) in the presence of one or more of the organometallic salt (A) represented by the general formula (1) Method;
(III) an aliphatic alcohol alkylene oxide adduct having a narrow molecular weight distribution obtained by the production method.

The alkoxylation reaction catalyst of the present invention has the following effects.
(1) Since the catalyst has high activity, the reaction time can be greatly shortened, and a high mole number alkylene oxide can be added.
(2) An alkylene oxide adduct having a narrow molecular weight distribution (c <0.7) is obtained.
(3) An unreacted alcohol is small and a low odor alkylene oxide is obtained.

The alkoxylation catalyst of the present invention is represented by the following general formula (1).
M [RfSO ₃ ] _n (1)
In the formula, metal (M) is copper (Cu), cadmium (Cd), titanium (Ti), hafnium (Hf), chromium (Cr), molybdenum (Mo), manganese (Mn), iron (Fe), palladium An atom selected from (Pd) and a rare earth metal atom.
Of these metal atoms, Cu, Cd, Ti, Cr, Fe, and rare earth atoms (for example, scandium (Sc), yttrium (Y), lanthanum (La), etc.), more preferably Cu, Cd , Cr, Ti, Fe, Sc, and La, and most preferably Ti, Fe, and Sc.

RfSO ₃ is a perfluoroalkylsulfonic acid group, and Rf represents a perfluoroalkyl group having 1 to 16 carbon atoms. Specifically, trifluoromethanesulfonic acid group, pentafluoroethanesulfonic acid group, heptafluoropropanesulfonic acid group, nonafluorobutanesulfonic acid group, undecafluoropentanesulfonic acid group, tridecafluorohexanesulfonic acid group, pentadecacarbon group Examples thereof include the same or different perfluoroalkylsulfonic acid groups selected from a fluoroheptanesulfonic acid group and a heptadecafluorooctanesulfonic acid group. Of these RfSO ₃ , preferably a trifluoromethanesulfonic acid group, a pentafluoroethanesulfonic acid group, a heptafluoropropanesulfonic acid group, a nonafluorobutanesulfonic acid group, more preferably a trifluoromethanesulfonic acid group or a pentafluoroethanesulfonic acid group. is there.

  The metal catalyst of the present invention can be obtained by a known synthesis method. Mukaiyama, N .; Iwasawa, R.W. Stevens, T.W. It can be synthesized by the method described in detail in Haga, Tetrahedron, 40, 1381 (1984).

Next, although an example of a synthesis method is described, it is not limited to this.
Add 0.95 to 2.00 times the equivalent amount of scandium to 12-16N trifluoromethanesulfonic acid solution to dissolve scandium as scandium trifluoromethanesulfonate (scandium triflate) The solution was dissolved at a boiling point of 100 to 150 ° C. for 1 to 3 hours to obtain scandium triflate. When the aqueous solution thus obtained was subjected to low-temperature vacuum evaporation of surplus water at a temperature of 40 to 80 ° C. and a degree of vacuum of 50 to 250 Torr by using an evaporator, a white solid was obtained in about 1 hour. It was. Furthermore, high temperature vacuum drying was performed for 24 hours at a temperature of 100 to 300 ° C. and a degree of vacuum of 10 to 10 ⁻² Torr to obtain a white powder of scandium triflate, which was then sealed with nitrogen gas. Scandium triflate was obtained.
Although the specific example of the metal catalyst obtained by said method is described in Table 1, it is not limited to these. The composition of the obtained scandium triflate is measured by an atomic absorption method.

  Of these, Nos. 1, 2, 4, 7, 8, 10, and 11 in the above table are preferred, Nos. 1, 2, 4, 7, and 10 are more preferred. 1, 4, and 10.

  Another invention of the present invention is an aliphatic alcohol alkylene obtained by ring-opening addition polymerization of an alkylene oxide (C) to an aliphatic alcohol (B) in the presence of at least one of the above organometallic salts (A). It is a manufacturing method of an oxide adduct (D).

  As aliphatic alcohol (B) in this invention, a C1-C25 aliphatic alcohol is preferable, More preferably, it is C1-C22, Most preferably, it is C1-C18 aliphatic alcohol. These may be linear or branched alcohols, or monohydric or dihydric or higher alcohols. These alcohols may be natural alcohols or synthetic alcohols (eg, Ziegler alcohol, oxo alcohol, etc.).

  Specific examples of the monohydric alcohol include methanol, ethanol, n-propanol, butanol, pentyl alcohol, hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, decyl alcohol, undecyl alcohol, dodecyl alcohol, tridecyl alcohol, tetradecyl Saturated aliphatic alcohols such as alcohol, hexadecyl alcohol, octadecyl alcohol, nonadecyl alcohol; propenyl alcohol, butenyl alcohol, 1-pentenyl alcohol, 1-octenyl alcohol, 1-decenyl alcohol, 1-dodecenyl Unsaturated aliphatic alcohols such as alcohol, tridecenyl alcohol, pentadecenyl alcohol, oleyl alcohol, gadreyl alcohol, linoleyl alcohol Le; methylcyclohexyl alcohol, ethylcyclohexyl alcohol, n- propyl cyclohexyl alcohol, octyl cyclohexyl alcohol, nonyl cyclohexyl alcohol, alicyclic alcohols, such as adamantyl alcohol.

Specific examples of the polyhydric alcohol include dihydric alcohol (alkylene glycol such as ethylene glycol, propylene glycol, 1,3- or 1,4-butanediol, 1,6-hexanediol and neopentyl glycol; and cyclohexanediol and Cycloalkylene glycols such as cyclohexanedimethanol, etc., trihydric alcohols (glycerin, trimethylolpropane, trimethylolethane, alkanetriols such as hexanetriol, etc.); 4- to 8-valent polyhydric alcohols (pentaerythritol, sorbitol, mannitol, Intramolecular dehydration of alkane polyols such as sorbitan, intermolecular dehydration of alkane polyols such as diglycerin and dipentaerythritol; and sucrose, glucose, mannose, fructose And sugar and their derivatives such as methyl glucoside); and the like.
Among these alcohols, monovalent aliphatic alcohols are preferable from the viewpoint of the degree of narrowing, more preferably monovalent primary or secondary alcohols, and particularly preferably monovalent primary alcohols. Specific examples of particularly preferable ones include dodecyl alcohol, tridecyl alcohol, tetradecyl alcohol, hexadecyl alcohol, and octadecyl alcohol.

  In the present invention, the alkylene oxide (C) is preferably an alkylene oxide having 2 to 8 carbon atoms, particularly preferably 2 to 6 carbon atoms. Specific examples of preferable ones include ethylene oxide (hereinafter abbreviated as EO), propylene oxide (hereinafter abbreviated as PO), 1,2- or 2,3-butylene oxide, tetrahydrofuran, styrene oxide and the like. More preferred are EO and PO, and particularly preferred is EO.

As the usage-amount of (A), 0.001-1 mass part is preferable with respect to 100 mass parts of the sum total of (B) and (C) from the point of reaction rate and economical efficiency. More preferably, it is 0.003-0.8 mass part, Most preferably, it is 0.005-0.5 mass part.
The number of moles added of (C) to (B) is preferably from 1 to 160 on average, and more preferably from 1 to 80 on average, from the viewpoint of the degree of narrowing.

As a reaction condition in the case of reacting (B) and (C), for example, after mixing (B) and (A) and performing nitrogen substitution, at a pressure of −0.8 to 5 kgf / cm ² , Examples include a method in which (C) is introduced at a temperature of 80 to 200 ° C., a predetermined amount of (C) is added, and then ripening is performed until the pressure in the reaction system becomes equilibrium at 80 to 200 ° C.

  The weight average molecular weight (Mw) of the aliphatic alcohol alkylene oxide adduct (D) thus obtained is preferably 76 to 7,400, more preferably 76 to 3,900. Particularly preferred is 76-1,250. When Mw is in this range, the surface activity such as osmotic force is particularly good and preferable. In the present invention, the molecular weight is a value measured by gel permeation chromatograph (GPC).

  In (D), the distribution constant c which is a narrowing degree index calculated from the equation (2) derived from the Weibull distribution rule is preferably 0.2 to 0.7, and more preferably 0.2. It is -0.65, Most preferably, it is 0.3-0.6. The smaller this value, the smaller the unreacted alcohol content and the narrower the molecular weight distribution.

  Since the catalyst of the present invention is highly active, the reaction time can be significantly shortened by the production method of the present invention. In addition, an alkylene oxide having a high mole number can be addition-polymerized with an aliphatic alcohol, and an alkylene oxide adduct (D) of an aliphatic alcohol having a high degree of narrowing (distribution constant c is less than 0.7) can be obtained.

  (D) obtained by the reaction can be used for various purposes as it is or by adjusting the pH. For example, ["KYOWARD 600" manufactured by Kyowa Chemical Industry Co., Ltd.] After the adsorption treatment with an adsorbent such as, the catalyst can be removed from the polymer by filtration. At this time, if necessary, the time required for the filtration operation can be shortened by using a diatomaceous earth filter aid [for example, Radiolite manufactured by Showa Chemical Industry Co., Ltd.] as a filter aid.

  Since (D) obtained by the production method of the present invention has a low content of unreacted aliphatic alcohol, it is preferable to obtain an anionic activator such as a low odor sulfate or carboxymethylated product in terms of odor improvement. It can be used as an intermediate. Of course, it is also useful for applications such as the above-mentioned emulsifiers and dispersants.

[Example]
EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to this. Moreover, a part shows a mass part and% shows the mass%.

The measurement conditions of molecular weight by GPC are as follows.
<< GPC measurement conditions >>
Model: HLC-8120 (manufactured by Tosoh Corporation)
Column TSK gel SuperH4000
TSK gel SuperH3000
TSK gel SuperH2000
(Both manufactured by Tosoh Corporation)
Column temperature: 40 ° C. Detector: RI
Solvent: Tetrahydrofuran Flow rate: 0.6 ml / min Sample concentration: 0.25%
Injection volume: 10 μl
Standard: Polyoxyethylene glycol (manufactured by Tosoh Corporation; TSK STANDARD
POLYETHYLENE OXIDE)
Data processor: SC-8020 (manufactured by Tosoh Corporation)

The measurement of the unreacted aliphatic alcohol concentration by gas chromatography (hereinafter abbreviated as GC) is as follows.
<< GC measurement conditions >>
Model: Gas chromatograph GC-14B (manufactured by Shimadzu Corporation)
Detector: FID
Column: Glass column (inner diameter = about 3 mm, length = about 2 m)
Column filler: Silicon GE SE-30 5%
Column temperature: raised from 90 ° C to 280 ° C. Temperature rising rate = 4 ° C./min Carrier gas: Nitrogen Sample: 50% acetone solution Injection volume: 1 μl
Quantification: Quantification was performed using an aliphatic alcohol having 2 or 3 carbon atoms as an internal standard depending on the aliphatic alcohol used.

[Synthesis 1] (Synthesis of catalyst)
Add 1.05 times the amount of scandium oxide equivalent to that required for dissolution of scandium as scandium trifluoromethanesulfonate (scandium triflate) to a 15N trifluoromethanesulfonate solution at a boiling temperature of 120 ° C. After dissolution for 2 hours, scandium triflate was obtained. The aqueous solution thus obtained was subjected to low-temperature vacuum evaporation of surplus water at a temperature of 60 ° C. and a vacuum degree of 100 Torr by using an evaporator, and a white solid was obtained in about 1 hour. Further, high-temperature vacuum drying was performed for 24 hours at a temperature of 200 ° C. and a vacuum degree of 10 ⁻¹ torr to obtain a white powder of scandium triflate, which was then sealed with nitrogen gas.
The composition of scandium triflate analyzed by the atomic absorption method is Sc: 9.28%, Fe: 60 ppm, Al: 150 ppm, Sn: 21 ppm, Mn: 12 ppm, Ni: 13 ppm, Ca: 61 ppm, Mg: 10 ppm, Si: A high-purity scandium triflate having a concentration of 14 ppm and a scandium triflate of 99.1% was obtained.

[Synthesis Example 2] (Synthesis of catalyst)
Titanium tetraflate was obtained in the same manner as in Example 1 except that the scandium oxide in Example 1 was replaced with titanium oxide. The composition of titanium tetraflate analyzed by the atomic absorption method was Ti: 7.55%, Fe: 65 ppm, Al: 168 ppm, Mn: 10 ppm, Cu: 20 ppm, Ni: 11 ppm, Ca: 62 pm, Mg: 32 ppm, Si: A high-purity titanium tetraflate having a content of 14 ppm and 99.3% of titanium tetraflate was obtained.
[Example 1] (Synthesis of aliphatic alcohol alkylene oxide adduct)
To a glass autoclave having a stirring and temperature control function, 186 parts (1 mol) of lauryl alcohol and 0.02 part of scandium triflate of [Synthesis Example 1] were added, and the inside of the mixed system was replaced with nitrogen. Dehydration was performed at 120 ° C. for 1 hour under reduced pressure (about 20 mmHg). Next, 132 parts (3 moles) of EO was reacted at 120 ° C. for 3 hours while being introduced at 120 ° C. so that the gauge pressure was 1 to ² kgf / cm ² . After removing unreacted EO under reduced pressure, 3 parts of “KYOWARD 600 (manufactured by Kyowa Chemical Industry Co., Ltd.)” is added to the product. An oxide adduct (A1-1) was obtained. The molecular weight distribution and unreacted aliphatic alcohol content of this product were measured by GPC and GC. As a result, Mw / Mn was 1.05, unreacted alcohol content was 1.50%, and Weibull distribution constant c was 0.56.

[Example 2] (Synthesis of aliphatic alcohol alkylene oxide adduct)
In the same manner as in Example 2, 186 parts (1 mol) of lauryl alcohol and 0.02 part of scandium triflate of Example 1 were added, the inside of the mixed system was replaced with nitrogen, and then under reduced pressure (about 20 mmHg). Dehydration was performed at 120 ° C. for 1 hour. Next, 308 parts (7 mol) of EO was reacted at 120 ° C. for 5 hours while introducing the gauge pressure at 1 to ² kgf / cm ² at 120 ° C. After the reaction, unreacted EO was removed under reduced pressure, and adsorption treatment and filtration were performed in the same manner as in Example 1 to obtain the aliphatic alcohol alkylene oxide adduct (A1-2) of the present invention. The molecular weight distribution and unreacted aliphatic alcohol content of this product were measured by GPC and GC. As a result, Mw / Mn was 1.04, unreacted alcohol amount was 0.58%, and Weibull distribution constant c was 0.52.

[Example 3] (Synthesis of aliphatic alcohol alkylene oxide adduct)
In the same manner as in Example 2, 186 parts (1 mol) of lauryl alcohol and 0.02 part of scandium triflate of Example 1 were added, the inside of the mixed system was replaced with nitrogen, and then under reduced pressure (about 20 mmHg). Dehydration was performed at 120 ° C. for 1 hour. Subsequently, 528 parts (12 mol) of EO was reacted at 120 ° C. for 7 hours while introducing the gauge pressure to be 1 to ² kgf / cm ² at 120 ° C. After the reaction, unreacted EO was removed under reduced pressure, and adsorption treatment and filtration were performed in the same manner as in Example 1 to obtain the aliphatic alcohol alkylene oxide adduct (A1-3) of the present invention. The molecular weight distribution and unreacted aliphatic alcohol content of this product were measured by GPC and GC. As a result, Mw / Mn was 1.04, unreacted alcohol content was 0.20%, and Weibull distribution constant c was 0.47. .

[Example 4] (Synthesis of aliphatic alcohol alkylene oxide adduct)
In place of the scandium triflate in [Example 1], 0.02 part of titanium tetraflate of [Synthesis Example 2] was used, and the aliphatic alcohol alkylene oxide adduct (A1- 4) was obtained.
This product had an Mw / Mn of 1.04, an unreacted alcohol amount of 1.25%, and a Weibull distribution constant c of 0.48.

[Comparative Example 1] (Synthesis of aliphatic alcohol alkylene oxide adduct)
In a glass autoclave with stirring and temperature control functions, 186 parts (1 mol) of lauryl alcohol and 0.06 part of aluminum perchlorate 9-hydrate in place of scandium triflate are used, and the inside of the mixed system is replaced with nitrogen. After that, dehydration was performed at 120 ° C. for 1 hour under reduced pressure (about 20 mmHg). Next, 132 parts (3 moles) of EO was reacted at 120 ° C. for 20 hours while introducing a gauge pressure of 1 to ² kgf / cm ² at 120 ° C. After the reaction, unreacted EO was removed under reduced pressure, and adsorption treatment and filtration were carried out in the same manner as in Example 1 to obtain an aliphatic alcohol alkylene oxide adduct (H-1).
The molecular weight distribution of (H-1) and the amount of unreacted aliphatic alcohol were measured by GPC and GC. As a result, Mw / Mn was 1.05, the amount of unreacted aliphatic alcohol was 1.78%, and the distribution constant c was calculated. The value was 0.65.

[Comparative Example 2] (Synthesis of aliphatic alcohol alkylene oxide adduct)
186 parts (1 mol) of lauryl alcohol and 0.3 part of potassium hydroxide were charged into a glass autoclave having a stirring and temperature control function, and the mixed system was replaced with nitrogen, and then under reduced pressure (about 20 mmHg). Dehydration was performed at 120 ° C. for 1 hour. Subsequently, 308 parts (7 mol) of EO was reacted at 120 ° C. for 5 hours while introducing the gauge pressure at 1 to 3 kgf / cm 2 at 120 ° C. After the reaction, unreacted EO was removed under reduced pressure, and adsorption treatment and filtration were performed in the same manner as in Example 1 to obtain an aliphatic alcohol alkylene oxide adduct (H-2).
This product had an Mw / Mn of 1.32, an unreacted aliphatic alcohol amount of 7.7%, and a calculated value of the distribution constant c of 3.21.

[Comparative Example 3] (Synthesis of aliphatic alcohol alkylene oxide adduct)
186 parts (1 mol) of lauryl alcohol was charged into a glass autoclave equipped with stirring and temperature control, and the system was purged with nitrogen, then dehydrated at 120 ° C. under reduced pressure (about 20 mmHg), and heated to 40 ° C. Then, 0.3 part of boron trifluoride diethyl ether was added, and the inside of the mixed system was replaced with nitrogen. Subsequently, 440 parts (10 mol) of EO was reacted at 80 ° C. for 8 hours while introducing the gauge pressure to be about 1 kgf / cm 2 at 80 ° C. The reaction product was neutralized with alkali to obtain an aliphatic alcohol alkylene oxide adduct (H-3).
The Mw / Mn of this product was 1.14, the amount of unreacted aliphatic alcohol was 1.04%, and the calculated value of the distribution constant c was 1.66. In this comparative example, about 8% by-product of polyethylene glycol was observed.

The results are summarized in Table 2.

It is useful as a catalyst for alkoxylation reaction of aliphatic alcohol and alkylene oxide.

Claims (8)

An alkoxylation reaction catalyst of an aliphatic alcohol (B) and an alkylene oxide (C), comprising one or more organic metal salts (A) represented by the following general formula (1).
M [RfSO ₃ ] _n (1)
[Wherein M is copper (Cu), cadmium (Cd), titanium (Ti), hafnium (Hf), chromium (Cr), molybdenum (Mo), manganese (Mn), iron (Fe), palladium (Pd) And a rare earth metal atom, and n represents an integer equal to the valence of M. Rf represents a perfluoroalkyl group having 1 to 16 carbon atoms. ]   The alkoxylation reaction catalyst according to claim 1, wherein M in the general formula (1) is a rare earth metal atom.   The alkoxylation reaction catalyst according to claim 2, wherein the rare earth metal atom is at least one selected from the group consisting of scandium (Sc), yttrium (Y), and lanthanum (La).   A method for producing an aliphatic alcohol alkylene oxide adduct, wherein the (B) is subjected to addition polymerization in the presence of one or more of the metal catalysts according to claim 1.   The production method according to claim 4, wherein (B) is an aliphatic alcohol having 1 to 25 carbon atoms.   6. The production method according to claim 4, wherein (C) is ethylene oxide.   An aliphatic alcohol alkylene oxide adduct obtained by the production method of claim 4. The aliphatic alcohol alkylene oxide adduct according to claim 7, wherein the Weibull distribution constant c is 0.2 to 0.7.