JP4406489B2 - Alkoxylation catalyst and process for producing alkylene oxide adducts using this catalyst - Google Patents

Description

【００５４】
表１の結果から明らかなように、本発明の触媒によれば、高い触媒活性が得られることが確認できた。特に、実施例３の触媒によれば、比較例１の触媒と比較して、触媒活性が２．５倍程度まで向上した。
【００５５】
このように、本発明の触媒は触媒活性が高いため、反応に要する時間が短縮される。例えば、上記反応条件および操作方法による反応において、比較例２の触媒を用いた場合の反応時間は２７６分であったのに対して、実施例６の触媒を用いた場合の反応時間は８８分であった。
【００５６】
次に、実施例６および比較例２の触媒を用いて、上記反応条件および操作方法による反応を実施し、副生物である高分子ポリエチレングリコール（分子量２００００以上）の生成量を測定した。その結果、高分子ポリエチレングリコールの生成量は、実施例６の触媒を用いた場合は０．０４重量％であり、比較例２の触媒を用いた場合は０．０６重量％であった。なお、これらの数値は、全生成物量に対する重量％である。
このように、本発明によれば、触媒の選択性を劣化させることなく、高い触媒活性を達成することができる。
【００５７】
また、実施例６および比較例２の触媒を用いて、上記反応条件および操作方法による反応を実施し、生成物であるエチレンオキサイド付加物の付加モル分布を測定した。実施例６の触媒を用いた場合の結果を図１に示し、比較例２の触媒を用いた場合の結果を図２に示す。図１および図２に示すように、実施例６の触媒によっても、比較例２の触媒と同様に、狭い付加モル分布を得ることができる。
このように、本発明によれば、触媒反応で生成するアルキレンオキサイド付加物の付加モル分布を狭くするという特性を劣化させることなく、高い触媒活性を達成することができる。
【００５８】
【発明の効果】
以上説明したように、本発明のアルコキシル化用触媒は、アルコキシル化触媒活性を有する複合金属酸化物と、炭化水素鎖を有する分子とを含み、前記複合金属酸化物表面に前記分子が結合し、前記分子が、更に金属原子を含み、この金属原子と、前記複合金属酸化物表面の金属原子とが、酸素原子を介して結合し、前記分子に含まれる金属原子が、チタンおよびアルミニウムの少なくとも１種の金属であるため、高い触媒活性を得ることができる。
【図面の簡単な説明】
【図１】 実施例６の触媒を用いた反応により生成したエチレンオキサイド付加物の付加モル分布を示す図である。
【図２】 比較例２の触媒を用いた反応により生成したエチレンオキサイド付加物の付加モル分布を示す図である。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an alkoxylation catalyst and a method for producing an alkylene oxide adduct using the alkoxylation catalyst.
[0002]
[Prior art]
Alkylene oxide adducts of organic compounds having active hydrogen or their derivatives are widely used as solvents, surfactants and various chemical intermediates. In particular, alkylene oxide adducts obtained by adding ethylene oxide or propylene oxide to alcohols, fatty acids, fatty acid esters, amines or alkylphenols are widely used as nonionic surfactants.
Among them, an adduct having a narrow alkylene oxide addition molar distribution has advantages such as higher detergency and foaming power and less odor derived from unreacted substances than an adduct having a wide addition molar distribution. is doing.
[0003]
As an alkoxylation catalyst for producing such an alkylene oxide adduct, a composite metal oxide as shown below has been proposed.
1) Magnesium oxide to which metal ions such as aluminum are added (Japanese Patent Laid-Open No. 1-164437: for example, magnesium oxide containing 3% by weight of aluminum is disclosed).
2) A calcined hydrotalcite obtained by calcining natural or synthetic hydrotalcite (Japanese Patent Laid-Open No. 2-71841).
3) Magnesium oxide containing zinc, antimony, tin and the like (Japanese Patent Laid-Open No. 7-227540).
4) Aluminum / magnesium composite oxide obtained by firing aluminum hydroxide / magnesium (JP-A-8-268919).
[0004]
According to the composite metal oxide, the alkoxylation reaction can be catalyzed by the joint effect of the acid point and base point on the catalyst surface, and an adduct having a narrow alkylene oxide addition molar distribution can be produced. .
[0005]
[Problems to be solved by the invention]
In the production of an alkylene oxide adduct, the higher the catalytic activity of the alkoxylation catalyst used, the higher the production efficiency. This is because when the catalyst activity is high, the reaction time can be shortened and the reaction can be carried out with a small amount of catalyst, so that the catalyst can be easily separated and recovered after the reaction.
For this reason, in the catalyst for alkoxylation, further improvement in catalytic activity is required.
[0006]
An object of the present invention is to provide a catalyst for alkoxylation having high catalytic activity and a method for producing an alkylene oxide adduct using the catalyst.
[0007]
[Means for Solving the Problems]
In order to achieve the above object, the alkoxylation catalyst of the present invention is an alkoxylation catalyst containing a composite metal oxide having an alkoxylation catalyst activity, further comprising a molecule having a hydrocarbon chain, and the composite metal The molecule is bonded to the surface of the oxide , the molecule further contains a metal atom, and the metal atom and the metal atom on the surface of the composite metal oxide are bonded through an oxygen atom and included in the molecule. The metal atom is at least one metal of titanium and aluminum .
[0008]
Such an alkoxylation catalyst has a high catalytic activity. This is presumed to be because the surface of the composite metal oxide is hydrophobized by molecules containing hydrocarbon chains, so that dispersibility in a lipophilic reaction solvent is improved.
Further, in this alkoxylation catalyst, there is no limitation on the composition and firing conditions of the composite metal oxide. Therefore, it is possible to obtain high catalytic activity without impairing the characteristics (for example, selectivity of the catalyst, addition molar distribution of the alkylene oxide adduct generated by the catalytic reaction) depending on the composition and firing conditions of the composite metal oxide. it can.
[0009]
In the catalyst for the alkoxylation, said molecule further comprises a metal atom, a metal atom, a metal atom of the complex metal oxide surface, which is attached via an oxygen atom. According to this configuration , high catalytic activity can be realized more reliably. This is presumably because the metal atom contained in the molecule functions as a new active site.
[0010]
The metal atom contained in the molecule is at least one metal of titanium and aluminum .
[0011]
In the alkoxylation catalyst, the composite metal oxide preferably contains magnesium and aluminum. According to this preferred example, it is possible to produce an alkylene oxide adduct having a narrow addition molar distribution in addition to ensuring high catalytic activity.
[0012]
In the alkoxylation catalyst, the composite metal oxide further contains at least one metal selected from the group consisting of Fe, Ni, Cr, Mn, Ti, B, Ga, Ce, Mo, and Zr. It is preferable to contain. According to this preferred example, the selectivity of the catalyst is improved, so that when used in the production of an alkylene oxide adduct, the production of high molecular polyalkylene glycol as a by-product can be suppressed, and the production efficiency can be improved. it can.
[0013]
The method for producing an alkylene oxide adduct of the present invention is characterized by adding an alkylene oxide to an organic compound in the presence of the alkoxylation catalyst of the present invention.
[0014]
DETAILED DESCRIPTION OF THE INVENTION
In the alkoxylation catalyst of the present invention, hydrocarbon chain-containing molecules are bonded to the surface of the composite metal oxide having alkoxylation catalytic activity.
[0015]
The composite metal oxide is not particularly limited as long as it has alkoxylation activity. Preferred examples of the composite metal oxide include magnesium / aluminum composite oxide. In this case, the atomic ratio of magnesium to aluminum is expressed as Al / (Mg + Al), for example, 0.1 to 0.7, preferably 0.3 to 0.6, and more preferably 0.4 to 0.00. 5.
[0016]
Furthermore, the composite metal oxide is preferably a magnesium / aluminum composite oxide containing a third metal. Examples of the third metal include Fe, Ni, Cr, Mn, Ti, B, Ga, Ce, Mo, and Zr. These may be used alone or in combination of two or more. Among these, Fe, Cr, and Mn are preferable, and Mn is particularly preferable. Content of the 3rd metal is atomic ratio with respect to all the metals in complex metal oxide, for example, 0.01-0.5, Preferably it is 0.05-0.3, More preferably, it is 0.1-0. 2.
[0017]
The composite metal oxide can be prepared by a conventionally known method such as an impregnation method or a coprecipitation method. Below, an example of the preparation method of the composite metal oxide powder by a coprecipitation method is demonstrated.
[0018]
First, a mixed aqueous solution containing ions of each metal is prepared, and a precipitant is added to the mixed aqueous solution. The mixed aqueous solution can be prepared, for example, by mixing aqueous solutions containing metal compounds such as nitrates, sulfates, carbonates, acetates, and chlorides of each metal. Moreover, as a precipitant, an alkali metal hydroxide, carbonate, or a mixture thereof can be used, for example.
[0019]
The precipitate deposited by adding the precipitant is washed with water and dried, and then fired to obtain a composite metal oxide. A calcination temperature is 300-1000 degreeC, for example, Preferably it is 600-900 degreeC, More preferably, it is 700-900 degreeC. The firing time is, for example, 0.5 to 10 hours, preferably 1 to 5 hours, and more preferably 2 to 4 hours. Further, the firing is preferably performed in an inert gas atmosphere, and more preferably in a nitrogen atmosphere.
[0020]
The hydrocarbon-containing molecule is not particularly limited as long as it contains a hydrocarbon chain and can bind to the surface of the composite metal oxide.
[0021]
The hydrocarbon chain contained in the hydrocarbon-containing molecule is not particularly limited, and a hydrophobic chain is preferable. For example, it is a hydrocarbon chain having 2 to 30, preferably 3 to 25, more preferably 8 to 18 carbon atoms. The hydrocarbon chain may be linear or branched and may be saturated or unsaturated. Further, it may contain heteroatoms such as O, N, P, and S.
[0022]
Further, the hydrocarbon chain-containing molecule has a metal atom at one end of the hydrocarbon chain, and the metal atom is bonded to the surface of the composite metal oxide by bonding the metal atom of the composite metal oxide via an oxygen atom. It is preferably fixed. As the metal atom, Al and Ti are particularly preferable.
[0023]
As such a hydrocarbon chain-containing molecule, for example, a coupling agent can be used. In particular, it is preferable to use a titanate coupling agent and an aluminum coupling agent. Moreover, a coupling agent may be used individually by 1 type, or may use 2 or more types together.
[0024]
Examples of titanate coupling agents include titanium acylate compounds and titanium chelate compounds. Specifically, for example, isopropyl triisostearoyl titanate, isopropyl tri-n-dodecylbenzenesulfonyl titanate, isopropyl tris (dioctyl pyrophosphate) titanate, tetraisopropyl bis (dioctyl phosphite) titanate, tetraisopropyl bis (ditridecyl phosphite) ) Titanate, tetra (2,2-diallyloxymethyl-1-butyl) bis (ditridecyl phosphite) titanate, bis (dioctyl pyrophosphate) oxyacetate titanate, bis (dioctyl pyrophosphate) ethylene titanate, isopropyl trioctanoyl titanate , Isopropyl dimethacrylisostearoyl titanate, isopropyl tri (dioctyl phosphate) titanate, iso B pills tricumylphenyl titanate, isopropyl tri (N- aminoethyl - aminoethyl) such as titanates. Among these, isopropyl triisostearoyl titanate, isopropyl trioctanoyl titanate, and isopropyl dimethacrylisostearoyl titanate are preferable, and isopropyl triisostearoyl titanate is particularly preferable.
[0025]
Examples of the aluminum coupling agent include an aluminum acylate compound and an aluminum chelate compound. Specifically, acetoalkoxy aluminum diisopropylate is preferable.
[0026]
A method for bonding the hydrocarbon chain-containing molecule to the surface of the composite metal oxide is not particularly limited. For example, when a coupling agent is used, a known method can be employed as a surface treatment method of an inorganic powder with a coupling agent, such as a gas phase method, a liquid phase method, an autoclave method, or a mechanochemical method. In particular, the liquid phase method is preferable because the operation is simple and the apparatus is not restricted.
[0027]
An example of the treatment of the coupling agent by the liquid phase method will be described. First, an adsorbing liquid is prepared by dispersing a coupling agent in a solvent, and the composite metal oxide is immersed in the adsorbing liquid. Thereafter, the catalyst is filtered off from the adsorbed liquid, and this is washed and dried to obtain a composite metal oxide having a coupling agent bonded to the surface.
[0028]
Although it does not specifically limit as a solvent which comprises adsorption liquid, For example, benzene, n-hexane, toluene, ethanol, isopropanol, trichlene, methanol, ethyl acetate etc. can be used. Among these, benzene, n-hexane and isopropanol are preferable, and benzene and n-hexane are particularly preferable.
[0029]
The amount of the coupling agent contained in the adsorbent is appropriately determined depending on the type of the coupling agent and the composite metal oxide, and is, for example, 1 × 10 ⁻⁶ to 1 mol, preferably 1 per 1 g of the composite metal oxide. × 10 ^-5 to 1 mol, more preferably 1 × 10 ^{-4 to} 5 × 10 ^-1 mol. If the amount of the coupling agent is less than 1 × 10 ⁻⁶ mol, the effect of increasing the catalytic activity may be difficult to express. Further, even if the amount of the coupling agent is more than 1 mol, it is not possible to expect an effect of increasing the catalytic activity commensurate with the amount, which may be disadvantageous in terms of cost. This is because the effect of increasing the catalytic activity reaches saturation when the entire surface of the composite metal oxide is coated with the monomolecular film of the coupling agent.
[0030]
The temperature of the adsorbing liquid is, for example, 10 to 80 ° C, preferably 15 to 60 ° C, and more preferably 20 to 40 ° C. Moreover, the immersion time of a catalyst is 0.5 to 100 hours, for example, Preferably it is 1 to 50 hours, More preferably, it is 12 to 24 hours.
[0031]
Next, an example of the method for producing the alkylene oxide adduct of the present invention will be described. The production method of the present invention is carried out by reacting an organic compound with an alkylene oxide in the presence of the alkoxylation catalyst of the present invention.
[0032]
The organic compound is not particularly limited as long as it can be alkoxylated. Specific examples include organic compounds having active hydrogen and derivatives thereof. Examples include alcohols, phenols, polyols, fatty acids, fatty acid esters, carboxylic acids, thiols, fatty acid amides, aliphatic amines, and mixtures thereof. Among these, alcohols, fatty acid esters, and aliphatic amines are preferable, and alcohols are particularly preferable.
[0033]
Examples of alcohols include saturated or unsaturated alcohols having 2 to 30 carbon atoms, preferably 6 to 24 carbon atoms, and more preferably 12 to 18 carbon atoms. In particular, primary and secondary alcohols are preferable, and primary alcohols are more preferable. Alcohols may be used alone or as a mixture of two or more.
[0034]
Examples of phenols include mono-, di-, and trialkylphenols. In particular, mono-, di- or trialkylphenols having an alkyl group having 4 to 12 carbon atoms are preferred.
[0035]
As the polyols, polyethylene glycol, polypropylene glycol, glycerin, sorbitol and the like are preferable. In the case of polyethylene glycol and polypropylene glycol, the average degree of polymerization is, for example, 2 to 2000, preferably 4 to 500, and more preferably 10 to 200.
[0036]
Examples of the fatty acids include saturated or unsaturated fatty acids having 8 to 22 carbon atoms, preferably 10 to 20 carbon atoms, more preferably 12 to 18 carbon atoms, and mixtures thereof. In particular, caprylic acid, capric acid, lauric acid, myristic acid, oleic acid, stearic acid and mixtures thereof are preferred. Such fatty acids can be obtained by, for example, decomposition of coconut oil, palm oil, palm kernel oil, soybean oil, sunflower oil, rapeseed oil, and fish fat oil. Moreover, as fatty acid ester, what esterified the said fatty acid with a C1-C4 alkyl group is mentioned, for example.
[0037]
Examples of the aliphatic amines include aliphatic amines having a saturated or unsaturated alkyl group having 8 to 44 carbon atoms, preferably 10 to 22 carbon atoms, and more preferably 12 to 18 carbon atoms. In particular, primary aliphatic amines are preferred. Examples of fatty acid amides include fatty acid amides having a saturated or unsaturated acyl group having 8 to 22, preferably 10 to 20, and more preferably 12 to 18 carbon atoms. In particular, primary or secondary fatty acid amides are preferred.
[0038]
As the alkylene oxide to be reacted with the organic compound, it is preferable to use an alkylene oxide having 2 to 8 carbon atoms. Particularly, an alkylene oxide having 2 to 4 carbon atoms, that is, ethylene oxide, propylene oxide, and butylene oxide is preferable.
[0039]
The reaction conditions for the alkoxylation reaction using the catalyst of the present invention are not particularly limited, and can be carried out, for example, under conventional reaction conditions. Hereinafter, preferable reaction conditions will be described. The reaction temperature is, for example, 80 to 230 ° C, preferably 120 to 200 ° C, more preferably 160 to 180 ° C. Although reaction pressure is suitably determined by reaction temperature, it is 0-20 atm, for example, Preferably it is 2-8 atm, More preferably, it is 2-6 atm. The amount of the catalyst used is appropriately determined depending on the ratio of the organic compound to be subjected to the reaction and the alkylene oxide, and is, for example, 0.01 to 20 parts by weight, preferably 0.000, relative to 100 parts by weight of the organic compound. 05 to 10 parts by weight, more preferably 0.1 to 5 parts by weight.
[0040]
Next, an example of a specific reaction operation will be described. First, an organic compound as a starting material and a catalyst are charged into an autoclave, the inside of the autoclave is replaced with nitrogen, and then alkylene oxide is introduced and reacted under predetermined temperature and pressure conditions. After completion of the reaction, the product is cooled, and then the catalyst is filtered off from the product to obtain an alkylene oxide adduct.
[0041]
【Example】
EXAMPLES Hereinafter, although an Example demonstrates this invention still in detail, this invention is not limited by the following Example.
[0042]
Example 1
_{2.5MgO · Al 2 O 3 · mH} 2 O aluminum hydroxide magnesium represented by the composition formula (Kyowa Chemical Industry Co., Ltd., trade name:. "Kyowaad 300", same below), and a stream of nitrogen, 700 Firing at 3 ° C. for 3 hours gave an aluminum / magnesium composite oxide powder. 100 ml of benzene and 0.0957 g (1.0 × 10 ⁻³ mol) of isopropyl tristearoyl titanate (manufactured by Ajinomoto Co., Inc., trade name: “KR TTS”, the same shall apply hereinafter) were mixed and stirred at room temperature for 10 minutes. To this was added 3.0 g of the composite metal oxide powder, and the mixture was stirred at room temperature for 30 minutes and then allowed to stand overnight. After standing, the composite metal oxide powder filtered off from the solvent was washed with 500 ml of benzene, and then washed with 250 ml of acetone. The washed composite metal oxide powder was vacuum dried at room temperature for 1 hour as a preliminary drying, and further vacuum dried at 50 ° C. for 3 hours to obtain a catalyst.
[0043]
(Example 2)
A catalyst was obtained in the same manner as in Example 1 except that 0.957 g (1.0 × 10 ⁻² mol) of isopropyl tristearoyl titanate was used.
[0044]
(Example 3)
A catalyst was obtained in the same manner as in Example 1 except that 9.57 g (1.0 × 10 ⁻¹ mol) of isopropyl tristearoyl titanate was used.
[0045]
Example 4
A catalyst was obtained in the same manner as in Example 1 except that 47.85 g (5.0 × 10 ⁻¹ mol) of isopropyl tristearoyl titanate was used.
[0046]
(Example 5)
A catalyst was obtained in the same manner as in Example 1, except that acetoalkoxyaluminum diisopropylate (manufactured by Ajinomoto Co., Inc., trade name: “AL-M”) was used instead of isopropyl tristearoyl titanate. In addition, 4.96 g (1.0 × 10 ⁻¹ mol) of acetoalkoxyaluminum diisopropylate was used with respect to 100 ml of benzene.
[0047]
(Example 6)
Magnesium nitrate hexahydrate 68.03 g (0.265 mol), aluminum nitrate nonahydrate 47.69 g (0.127 mol), manganese nitrate hexahydrate 24.33 g (0.085 mol) Was dissolved in 450 g of deionized water to obtain a solution A. On the other hand, 13.47 g (0.127 mol) of sodium carbonate was dissolved in 450 g of deionized water to obtain a solution B.
Solution A and Solution B were added dropwise to a catalyst preparation tank previously charged with 1800 g of deionized water in 1 hour while maintaining the pH at 9 with 2M NaOH and maintaining the temperature at 40 ° C. Aged for hours. The precipitate was filtered off from the solution, washed with 6 liters of deionized water, and spray-dried to obtain 30 g of a composite metal hydroxide. This composite metal hydroxide was calcined at 800 ° C. for 3 hours in a nitrogen atmosphere to obtain 19 g of a composite metal oxide powder containing Mg, Al, and Mn.
A catalyst was obtained in the same manner as in Example 3 except that this composite metal oxide powder was used.
[0048]
(Comparative Example 1)
Aluminum hydroxide-magnesium represented by the composition formula of _{2.5MgO · Al 2 O 3 · mH} 2 O, in a nitrogen stream to obtain a catalyst was calcined for 3 hours at 700 ° C..
[0049]
(Comparative Example 2)
A catalyst was obtained in the same manner as in Example 6 except that the coupling treatment was not performed.
[0050]
Using the catalysts obtained in Examples 1 to 6 and Comparative Examples 1 and 2, an alkylene oxide addition reaction was performed to evaluate the catalytic activity. The results are shown in Table 1. In addition, reaction conditions, operation methods, and evaluation methods of catalyst activity are as follows.
[0051]
[Reaction conditions and operation method]
The autoclave was charged with 400 g of lauryl alcohol and 0.4 g of catalyst, and the autoclave was purged with nitrogen, and then heated while stirring. Next, 663 g of ethylene oxide (EO) (7 mol per 1 mol of lauryl alcohol) was introduced while maintaining the inside of the autoclave at 180 ° C. and 3 atm to react lauryl alcohol with EO.
[0052]
[Method for evaluating catalytic activity]
The reaction is carried out under the above reaction conditions and operation method, and the EO supply rate (g-EO / min) from the time when the inside of the autoclave becomes constant temperature (180 ° C) and constant pressure (3 atm) is converted per unit catalyst amount. And an evaluation scale for catalyst activity (unit: g-EO / (min · g-cat)). The EO supply rate corresponds to EO consumption per unit time under constant temperature and pressure. In this measurement, the catalyst concentration was adjusted so as to be small enough to correctly evaluate the catalyst activity under the control of the chemical reaction rate.
[0053]

[0054]
As is clear from the results in Table 1, it was confirmed that the catalyst of the present invention can provide high catalytic activity. In particular, according to the catalyst of Example 3, the catalytic activity was improved to about 2.5 times that of the catalyst of Comparative Example 1.
[0055]
Thus, since the catalyst of the present invention has high catalytic activity, the time required for the reaction is shortened. For example, in the reaction according to the above reaction conditions and operation method, the reaction time when the catalyst of Comparative Example 2 was used was 276 minutes, whereas the reaction time when the catalyst of Example 6 was used was 88 minutes. Met.
[0056]
Next, using the catalysts of Example 6 and Comparative Example 2, the reaction was carried out under the above reaction conditions and operation methods, and the amount of high-molecular polyethylene glycol (molecular weight of 20000 or more) as a by-product was measured. As a result, the amount of high molecular polyethylene glycol produced was 0.04% by weight when the catalyst of Example 6 was used, and 0.06% by weight when the catalyst of Comparative Example 2 was used. In addition, these numerical values are weight% with respect to the total product amount.
Thus, according to the present invention, high catalytic activity can be achieved without degrading the selectivity of the catalyst.
[0057]
Moreover, the reaction of the said reaction conditions and operation method was implemented using the catalyst of Example 6 and Comparative Example 2, and the addition molar distribution of the ethylene oxide adduct which is a product was measured. The result when the catalyst of Example 6 is used is shown in FIG. 1, and the result when the catalyst of Comparative Example 2 is used is shown in FIG. As shown in FIGS. 1 and 2, the catalyst of Example 6 can obtain a narrow addition molar distribution similarly to the catalyst of Comparative Example 2.
Thus, according to the present invention, high catalytic activity can be achieved without degrading the characteristic of narrowing the addition molar distribution of the alkylene oxide adduct produced by the catalytic reaction.
[0058]
【The invention's effect】
As described above, the alkoxylation catalyst of the present invention includes a composite metal oxide having an alkoxylation catalytic activity and a molecule having a hydrocarbon chain, and the molecule is bonded to the surface of the composite metal oxide , The molecule further contains a metal atom, the metal atom and the metal atom on the surface of the composite metal oxide are bonded through an oxygen atom, and the metal atom contained in the molecule is at least one of titanium and aluminum. Since it is a seed metal , high catalytic activity can be obtained.
[Brief description of the drawings]
1 is a graph showing an addition molar distribution of an ethylene oxide adduct produced by a reaction using a catalyst of Example 6. FIG.
2 is a graph showing an addition molar distribution of an ethylene oxide adduct generated by a reaction using a catalyst of Comparative Example 2. FIG.

Claims (4)

A catalyst for alkoxylation comprising a composite metal oxide having an alkoxylation catalyst activity, further comprising a molecule having a hydrocarbon chain, wherein the molecule is bonded to the surface of the composite metal oxide ,
The molecule further includes a metal atom, and the metal atom and the metal atom on the surface of the composite metal oxide are bonded through an oxygen atom,
The alkoxylation catalyst, wherein the metal atom contained in the molecule is at least one metal of titanium and aluminum . The catalyst for alkoxylation according to claim 1 , wherein the composite metal oxide contains magnesium and aluminum. The alkoxylation according to claim 2 , wherein the composite metal oxide further contains at least one metal selected from the group consisting of Fe, Ni, Cr, Mn, Ti, B, Ga, Ce, Mo, and Zr. Catalyst. A method for producing an alkylene oxide adduct, comprising adding an alkylene oxide to an organic compound in the presence of the alkoxylation catalyst according to any one of claims 1 to 3 .

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