JPH06182206A - Catalyst for production of alkoxylate of active hydrogen-containing organic compound - Google Patents

Abstract

PURPOSE:To obtain a catalyst for production of alkoxylate of an active hydrogen-contg. org. compd. to bring an active hydrogen-contg. org. compd. and an alkylene oxide into reaction. CONSTITUTION:This catalyst for production of alkoxylate of an active hydrogen- contg. org. compd. to effect the reaction between an active hydrogen-contg. org. compd. and an alkylene oxide consists of a multiple oxide of magnesium and at least one selected from the group consisting of iron, nickel, cerium and ytterbium. This catalyst for production of alkoxylate has an advantage that the distribution of alkylene oxide-added polymn. degree in the produced alkoxylate is narrow in the reaction of an active hydrogen-contg. org. compd. and an alkylene oxide, and that the amt. of unreacted active hydrogen-contg. org. compd. and the amt. of byproduct are small.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a catalyst for producing an alkoxylate of an active hydrogen-containing organic compound composed of a magnesium-based composite oxide.

[0002]

Alkoxylates obtained by adding alkylene oxides such as ethylene oxide and propylene oxide to active hydrogen-containing compounds such as alcohols and phenols are used as surfactants and chemical intermediates.

The alkoxylation reaction for obtaining such an alkoxylate is represented by the following formula.

[0004]

[Chemical 1]

This reaction is carried out in the presence of an acidic or basic catalyst. The catalysts that have been conventionally used are
Lithium, sodium, potassium, etc., Group I alkali metal hydroxides, alkoxides, etc., soluble strongly basic compound catalysts, boron, zinc, indium, tin, antimony, etc. halides, sulfuric acid, phosphoric acid, etc. There are acidic catalysts such as inorganic acids.

[0006]

However, these known catalysts have advantages and disadvantages. The alcohol alkoxylate obtained by using a strongly basic catalyst such as caustic potash or caustic soda has a wide distribution of degree of polymerization of alkylene oxide and a large amount of unreacted raw material alcohol remains. When unreacted alcohol remains, it gives an unpleasant odor to the alkoxylate or its sulfate ester salt (Japanese Patent Publication No. 51-43483), and adversely affects the performance as a surfactant (US Pat. No. 3). No. 682,849), the residual amount of unreacted alcohol is desired to be as small as possible.

On the other hand, when an acidic catalyst is used, these drawbacks are alleviated considerably, but when the number of addition moles of alkylene oxide increases, a side reaction occurs, and a large amount of dioxane, dioxolane, dialkyl ether, polyalkylene glycol. And so on.

Further, JP-A-57-42646 discloses that alcohols having 2 to 36 carbon atoms are based on strontium hydroxide or a hydrate thereof or barium hydroxide or a hydrate thereof, and magnesium oxide is added thereto. It is disclosed that the alkoxylation reaction is carried out at a temperature of 120 ° C. to 260 ° C. by contacting with an alkoxylating agent in the presence of an appropriate amount of a catalyst added.

JP-A-58-110531 discloses at least one alkanol having 6 to 30 carbon atoms.
A method for producing an alkanol alkoxylate, which comprises reacting a seed with at least one alkylene oxide having 2 to 4 carbon atoms, wherein the first component is at least one basic magnesium compound soluble in alkanol, and A group consisting of aluminum, boron, zinc, titanium, silicon, molybdenum, vanadium, gallium, germanium, yttrium, zirconium, niobium, cadmium, indium, tin, antimony, tungsten, hafnium, tantalum, thallium, lead and bismuth as two components. Reacting in the presence of a cocatalyst containing at least one alkanol-soluble compound of at least one element selected from the group consisting of: Reaction products of um and alcohol, as well as ammonia compounds, amide thiolate, thiophenoxide, and nitride compounds are mentioned.
And the magnesium metals, magnesium oxide and magnesium hydroxide previously contemplated for use as alkoxylation catalysts are substantially insoluble in C ₆ to C ₃₀ alkanols at temperatures suitable for the present invention and thus the present invention. It is specified that it is not directly suitable for the purpose of.

JP-A-58-131930 discloses at least one alkanol having 6 to 30 carbon atoms.
In the method for producing an alkanol alkoxylate, which comprises reacting a seed with at least one alkylene oxide having 2 to 4 carbon atoms, at least one basic magnesium compound soluble in alkanol, and a reaction activator. As at least 2.0 mole percent 1 calculated on the basis of moles of alkanol
It is disclosed that at least one alkoxylate of at least one C ₁ to C ₃₀ alkanol having from 30 to 30 C ₂ to C ₄ alkylene oxide moieties is present and reacted.

JP-A-1-164437 and JP-A-3-1643
No. 242421 and JP-A-3-242242 disclose Al ³⁺ , Ga ³⁺ , In ³⁺ , Tl ³⁺ , Co ³⁺ , S.
for reacting an organic compound having active hydrogen with an alkylene oxide, which comprises magnesium oxide to which one or more metal ions selected from the group consisting of c ³⁺ , La ³⁺ and Mn ²⁺ are added. A catalyst for alkoxylation is disclosed.

The inventors of the present invention have keenly studied a novel catalyst for producing an active hydrogen-containing organic compound alkoxylate having a narrow degree of polymerization distribution of alkylene oxide, a high conversion rate of a raw material active hydrogen-containing compound, and a small amount of by-products. As a result of research and search, it has been found that a composite oxide of at least one selected from the group consisting of iron, nickel, cerium and ytterbium and magnesium has a unique and excellent catalytic effect not found in known catalysts. That is, when the magnesium-based composite oxide provided by the present invention is used as a catalyst in a reaction of adding an alkylene oxide to an active hydrogen-containing organic compound, the distribution of the degree of polymerization of the alkylene oxide is narrow, and the conversion of the raw material active hydrogen-containing compound is The inventors have found that an alkoxylate having a high rate and a small amount of by-products is provided, and completed the present invention.

[0013]

Means for Solving the Problems The present invention relates to a catalyst for producing an alkoxylate for producing an alkylene oxide adduct of an active hydrogen-containing compound by carrying out an alkoxylation reaction between an organic compound having active hydrogen and an alkylene oxide, For reacting an active hydrogen-containing organic compound with an alkylene oxide, characterized by comprising a composite oxide of at least one selected from the group consisting of nickel, cerium and ytterbium and magnesium.
The present invention provides a catalyst for the production of active hydrogen-containing organic compound alkoxylates.

The alkoxylate produced by the addition polymerization reaction of an active hydrogen-containing compound such as alcohol or phenol with an alkylene oxide by the catalyst for producing an alkoxylate according to the present invention has a content of unreacted active hydrogen-containing compound or by-product. And a narrow distribution of addition degree of alkylene oxide is obtained.

The active hydrogen-containing organic compound used in the present invention may be any one that can be alkoxylated, but it is composed of alcohols, phenols, polyols, carboxylic acids, thiols and amines. One kind or a mixture of two or more kinds selected from the group is preferably used. Alcohols having 1 to 30 carbon atoms
The linear or side chain monohydric and polyhydric alcohols are preferred, and monohydric alcohols having 6 to 24 carbon atoms are more preferred. Specific examples include linear monohydric alcohols such as 1-hexanol, 1-octanol, 1-decanol, 1-dodecanol, 1-tetradecanol and the like. Examples of phenols include phenol, cresol, nonylphenol and bisphenol A. Examples of the polyols include glycerin, sorbitol, hexanetriol, sorbit, monoethylene glycol, diethylene glycol, triethylene glycol and the like. Examples of the carboxylic acids include acetic acid, stearic acid, acrylic acid, oleic acid, benzoic acid, maleic acid and terephthalic acid. Examples of the thiols include methyl mercaptan and lauryl mercaptan. Examples of amines include tert-butylamine, ethylenediamine, aniline and the like.

The alkylene oxide used in the present invention may be any epoxide-containing substance in view of its properties, but ethylene oxide, propylene oxide, butylene oxide or a mixture of two or more thereof is preferably used. Iron, nickel, cerium and ytterbium for producing a catalyst for producing an active hydrogen-containing compound alkoxylate comprising a complex oxide of at least one selected from the group consisting of iron, nickel, cerium and ytterbium according to the present invention and magnesium As a supply source of the compound, a compound containing at least one element selected from the group consisting of iron, nickel, cerium and ytterbium can be used. The compound used is not particularly limited as long as it is a compound containing at least one element selected from iron, nickel, cerium and ytterbium, but iron, nickel, cerium and ytterbium chlorides, nitrates, sulfates and the like are preferable. Used.

Various magnesium compounds can be used as a magnesium source for producing the catalyst of the present invention. Magnesium oxide, hydroxide, chloride, nitrate, sulfate and the like are preferably used.

In the catalyst used in the present invention, the amount of iron, nickel, cerium and ytterbium oxide to be combined with magnesium oxide is 0.1 to 30% by weight based on the catalytic amount as iron, nickel, cerium and ytterbium. Is preferred, and 0.5 to 20% by weight is more preferred.

The method for producing the composite oxide of at least one selected from the group consisting of iron, nickel, cerium and ytterbium of the present invention and magnesium is as follows:
For example, immersing magnesium oxide in an aqueous solution of water-soluble salts of iron, nickel, cerium and ytterbium,
After evaporating to dryness, it is crushed and further 400-1000
Calcination at 50 ° C., preferably 500 ° C. to 800 ° C. (impregnation method), or a mixed aqueous solution of an aqueous solution of a water-soluble salt of iron, nickel, cerium, and ytterbium and an aqueous solution of magnesium, such as aqueous ammonia or urea. Neutralize with to precipitate a hydroxide or complex oxide hydrate, which is filtered, washed and dried, and then 400 to 1000 ° C.,
Preferably, there is a method of firing at 500 ° C to 800 ° C (coprecipitation method) and the like.

The method for adding the complex oxide of at least one selected from the group consisting of iron, nickel, cerium and ytterbium and magnesium of the present invention to the reaction between the active hydrogen-containing organic compound and the alkylene oxide is active hydrogen. It may be mixed with the contained organic compound or independently provided with an addition port. In either case, there is a method of adding the entire amount from the beginning or a method of continuously or intermittently adding a fixed amount during the reaction. Furthermore, there is also a method of heating and reacting a mixture of an active hydrogen-containing organic compound and an alkylene oxide in a predetermined amount in a catalyst packed bed. Any method is possible, and in practice, it may be appropriately selected in consideration of the reaction format and the operation method.

[0021]

The reaction system of the alkoxylation of the active hydrogen-containing organic compound and the alkylene oxide using the catalyst of the present invention may be a batch system, a semi-batch system or a continuous system. The reaction temperature is 80 ° C to 250 ° C, preferably 130 ° C.
-220 degreeC, Most preferably, it is 130-200 degreeC. If the reaction temperature is too low, the reaction rate will be slow, and conversely, if it is too high, the generated alkoxylate will be decomposed, so this should be avoided.

The reaction pressure is not particularly limited,
Although it is possible to use either normal pressure or increased pressure, when the reaction pressure is low, the solubility of the alkylene oxide in the active hydrogen-containing reactant is lowered, so that the reaction rate is reduced and the alkylene oxide is dispersed. Industrially, it is desirable to pressurize with an inert gas such as nitrogen. The amount of the catalyst used varies depending on the reaction conditions such as the type of active hydrogen-containing organic compound or alkylene oxide used in the reaction and the alkylene oxide, the molar ratio of the two, the reaction temperature and the reaction pressure, and is usually 0.1% of the amount of the alcohol or the like. -30% by weight is preferable, and 2-
10% by weight is more preferred.

After reacting the active hydrogen-containing organic compound with the alkylene oxide in the presence of the catalyst of the present invention, the catalyst can be filtered off by filtration or the like.

The alkoxylates obtained with the catalysts according to the invention are essentially neutral, and thus such that neutralization of the alkoxylates by addition of acids or alkalis as with conventional catalysts is carried out. No action required.

[0025]

The present invention will be described in more detail with reference to the following examples. However, this embodiment is one aspect of the invention and does not limit the invention.

Example 1 Magnesium oxide (MgO) powder 4 was prepared by dissolving 3.8 g of ytterbium (III) nitrate tetrahydrate in 500 g of pure water.
After adding 8 g and stirring sufficiently, it was evaporated to dryness. Then 11
After drying overnight at 0 ° C., it was pulverized, gradually heated while being evacuated, and heat-treated at 600 ° C. for 2 hours to obtain a catalyst.

In order to react 1-dodecanol with 4 moles of ethylene oxide, a stainless steel autoclave having a gas discharge pipe and a gas blowing pipe was used, which had a water content of 100 ppm.
-257 g of dodecanol and 26 g of the above catalyst were charged, the inside of the autoclave was replaced with nitrogen, and then the temperature was raised to 175 ° C with stirring. Then, the pressure inside the autoclave was adjusted to 1 kg / cm ² with nitrogen, and then ethylene oxide was gradually introduced while paying attention so that the partial pressure of ethylene oxide inside the autoclave was ½ or less of the total pressure. While maintaining the reaction temperature at 175 ° C., 243 g of ethylene oxide was introduced. The time required for introducing ethylene oxide was 3.5 hours. The temperature was kept at 175 ° C until the partial pressure of ethylene oxide in the autoclave was lowered (aging step), then the reaction solution was cooled to 70 ° C, and the catalyst was filtered off. The unreacted 1-dodecanol content of the ethoxylate of 1-dodecanol thus obtained was 5.0.
% (Gas chromatography area%). The ethylene oxide addition polymerization degree distribution of this ethoxylate was determined by gas chromatography and the results are shown in Table 1 and FIG. Similarly, FIG. 1 shows the ethylene oxide addition polymerization degree distribution of an ethoxylate (Comparative Example 2 described later) obtained using a conventional KOH catalyst. As is clear from the comparison between the two, the ethoxylate obtained using the catalyst of the present invention exhibits a very narrow distribution of degree of ethylene oxide addition polymerization as compared with the ethoxylate produced using the conventional catalyst. The amount of by-product polyethylene glycol contained in this ethoxylate was 1.0% by weight, which was smaller than that of the ethoxylate obtained by using the conventional BF ₃ catalyst (Comparative Example 3 described later).

Example 2 Ytterbium (III) nitrate tetrahydrate of Example 1.
Nickel (II) nitrate hexahydrate 7.6 g instead of 8 g
A composite oxide of magnesium and nickel was obtained according to the procedure of Example 1 except that was used. Further, the reaction was carried out in the same manner as in Example 1. The time required to introduce ethylene oxide was 14 hours. The amount of unreacted 1-dodecanol contained in the ethoxylate thus obtained was 4.3.
% (Gas chromatography area%). The results of the ethylene oxide addition polymerization degree distribution of this ethoxylate obtained by gas chromatography are shown in Table 1 and FIG. As shown in FIG. 2, the ethylene oxide addition polymerization degree distribution was a very narrow distribution of the ethylene oxide addition polymerization degree as compared with the ethoxylate obtained using the conventional KOH catalyst and BF ₃ catalyst.

Example 3 Ytterbium (III) nitrate tetrahydrate of Example 1
Cerium (III) nitrate hexahydrate 4.7 g instead of 8 g
A composite oxide of magnesium and cerium was obtained according to the procedure of Example 1 except that g was used. Further, the reaction was carried out in the same manner as in Example 1. The time required to introduce ethylene oxide was 10 hours. The amount of unreacted 1-dodecanol contained in the ethoxylate thus obtained was 4.4.
% (Gas chromatography area%). The results of the ethylene oxide addition polymerization degree distribution of this ethoxylate obtained by gas chromatography are shown in Table 1 and FIG. As shown in FIG. 3, the ethylene oxide addition polymerization degree distribution was very narrow compared to the ethoxylates obtained using the conventional KOH catalyst and BF ₃ catalyst.

Example 4 Ytterbium (III) nitrate tetrahydrate of Example 1.
A composite oxide of magnesium and iron was obtained according to the procedure of Example 1 except that 11.0 g of iron (III) nitrate nonahydrate was used instead of 8 g. Further, the reaction was carried out in the same manner as in Example 1. The time required to introduce ethylene oxide was 7 hours. The amount of unreacted 1-dodecanol contained in the ethoxylate thus obtained was 3.4% (gas chromatography area%). The results of the ethylene oxide addition polymerization degree distribution of this ethoxylate determined by gas chromatography are shown in Table 1 and FIG. As shown in FIG. 4, the ethylene oxide addition polymerization degree distribution was very narrow compared to the ethoxylates obtained using the conventional KOH catalyst and BF ₃ catalyst.

Example 5 Magnesium nitrate hexahydrate (250 g) and ytterbium nitrate tetrahydrate (3.0 g) were dissolved in pure water (500 ml) and mixed to obtain an aqueous solution. Let The formed precipitate was filtered, washed with distilled water, dried at 110 ° C. overnight, and pulverized. The obtained powder was gradually heated while being evacuated, and heat-treated at 600 ° C. for 2 hours to obtain a catalyst. The reaction was performed in the same manner as in Example 1 except that 13 g of this catalyst was used. The time required to introduce ethylene oxide was 3 hours. The amount of unreacted 1-dodecanol contained in the obtained ethoxylate was 4.4% (gas chromatography area%). Table 1 and FIG. 5 show the results of the distribution of the degree of ethylene oxide addition polymerization of this ethoxylate determined by the gas chromatography method.
As shown in FIG. 5, the ethylene oxide addition degree of polymerization distribution was a very narrow ethylene oxide addition degree of distribution distribution as compared with the ethoxylates obtained using the conventional KOH catalyst and BF ₃ catalyst.

Comparative Example 1 Magnesium oxide powder alone was heat treated while being evacuated in the same manner as in Example 1 to obtain 26 g of a catalyst.
It was used to react 1-dodecanol with ethylene oxide as in Example 1. 90 g of ethylene oxide was introduced into the autoclave during the reaction for 40 hours, and the catalytic activity was remarkably low as compared with Examples 1-5.
Table 1 shows the results of the distribution of the degree of addition polymerization of ethylene oxide of this ethoxylate determined by the gas chromatography method.

Comparative Example 2 257 g of 1-dodecanol and KO were placed in an autoclave.
H 0.5 g (0.10% by weight based on the product after the reaction) was charged, and KOH was completely dissolved by heating and dehydration under reduced pressure to form potassium alcoholate of 1-dodecanol, and then the temperature was further raised to 155 ° C. The mixture was heated and adjusted with nitrogen so that the internal pressure of the autoclave became 1 kg / cm ^2, and ethylene oxide was gradually introduced while paying attention so that the partial pressure of ethylene oxide in the autoclave became 1/2 or less of the total pressure. While maintaining the reaction temperature at 155 ° C., 243 g of ethylene oxide was introduced. The time required to introduce ethylene oxide was 3 hours. The unreacted 1-dodecanol content of the ethoxylate obtained after aging is about 13%.
(Gas chromatography area%). The ethylene oxide addition polymerization degree distribution of this ethoxylate was determined by gas chromatography and the results are shown in Table 1 and FIG.
~ 5. As is clear from the figure, the ethoxylate obtained using the conventional catalyst has a considerably broader ethylene oxide addition polymerization degree distribution than the ethoxylate obtained using the catalyst of the present invention.

Comparative Example 3 257 g of 1-dodecanol (C
After charging 0.53 g of ₂ H ₅ ) ₂ O.BF ₃ (0.05% by weight as BF ₃ with respect to the reaction product), 50
The temperature inside the autoclave is raised to 1 ° C and the pressure inside the autoclave is 1 kg /
It was adjusted to be cm ² , and ethylene oxide was gradually introduced while paying attention so that the partial pressure of ethylene oxide in the autoclave was 1/2 or less of the total pressure. Reaction temperature 5
While maintaining the temperature at 0 ° C, 243 g of ethylene oxide was introduced. The time required for introduction was 1.5 hours. The unreacted 1-dodecanol content of the obtained ethoxylate was 3.8% (gas chromatography area%).
The results of the ethylene oxide addition polymerization degree distribution of this ethoxylate obtained by gas chromatography are shown in Table 1 and FIGS. The amount of by-product polyethylene glycol was 4.8% by weight, which was considerably higher than the ethoxylate obtained by using the catalyst of the present invention. Example 6 3.9 g of ytterbium (III) nitrate tetrahydrate and 7.7 g of nickel (II) nitrate hexahydrate were each added to 50 parts of pure water.
Into a mixed aqueous solution obtained by mixing those dissolved in 0 g,
After 48 g of magnesium oxide powder was added and sufficiently stirred, the mixture was evaporated to dryness. Then, it was dried at 110 ° C. overnight, pulverized, gradually raised in temperature while being evacuated, and heat-treated at 600 ° C. for 2 hours to obtain a catalyst. Reaction was carried out in the same manner as in Example 1 except that 26 g of this catalyst was used. The time required to introduce ethylene oxide was 4 hours. The amount of unreacted 1-dodecanol contained in the ethoxylate thus obtained was 5.0% (gas chromatography area%).
Table 2 shows the results of the distribution of the degree of ethylene oxide addition polymerization of this ethoxylate obtained by gas chromatography.

Example 7 Following the procedure of Example 6 except that 4.8 g of cerium (III) nitrate hexahydrate was used in place of 7.7 g of nickel (II) nitrate hexahydrate of Example 6. A complex oxide of magnesium with ytterbium and cerium was obtained. Further, the reaction was carried out in the same manner as in Example 6. The time required to introduce ethylene oxide was 4 hours. The amount of unreacted 1-dodecanol contained in the ethoxylate thus obtained was 4.9% (gas chromatography area%). Table 2 shows the results of the distribution of the degree of ethylene oxide addition polymerization of this ethoxylate obtained by gas chromatography.

Example 8 Following the procedure of Example 6 except that 11.3 g of iron (III) nitrate nonahydrate was used in place of 7.7 g of nickel (II) nitrate hexahydrate of Example 6. A complex oxide of magnesium, ytterbium and iron was obtained. Further, the reaction was carried out in the same manner as in Example 6. The time required to introduce ethylene oxide was 4 hours. The amount of unreacted 1-dodecanol contained in the ethoxylate thus obtained was 4.1%.
(Gas chromatography area%). Table 2 shows the results of the distribution of the degree of ethylene oxide addition polymerization of this ethoxylate obtained by gas chromatography.

Example 9 Ytterbium (III) nitrate tetrahydrate of Example 6
Cerium (III) nitrate hexahydrate 4.8 instead of 9 g
A composite oxide of magnesium, nickel and cerium was obtained according to the procedure of Example 6 except that g was used.
Further, the reaction was carried out in the same manner as in Example 6. The time required to introduce ethylene oxide was 11 hours. The amount of unreacted 1-dodecanol contained in the ethoxylate thus obtained was 5.1% (gas chromatography area%).
Met. Table 2 shows the results of the distribution of the degree of ethylene oxide addition polymerization of this ethoxylate obtained by gas chromatography.

Example 10 Ytterbium (III) nitrate tetrahydrate of Example 6
A composite oxide of magnesium, nickel and iron was obtained according to the procedure of Example 6 except that 11.4 g of iron (III) nitrate nonahydrate was used instead of 9 g. Further, the reaction was carried out in the same manner as in Example 6. The time required to introduce ethylene oxide was 7.5 hours. The amount of unreacted 1-dodecanol contained in the ethoxylate thus obtained was 3.7% (gas chromatography area%). Table 2 shows the results of the distribution of the degree of ethylene oxide addition polymerization of this ethoxylate obtained by gas chromatography.

Example 11 Ytterbium (III) nitrate tetrahydrate of Example 6 3.
Performed except that 4.9 g of cerium (III) nitrate hexahydrate and 11.3 g of iron (III) nitrate nonahydrate were used instead of 9 g and 7.7 g of nickel (II) nitrate hexahydrate. A composite oxide of magnesium, cerium and iron was obtained according to the procedure of Example 6. Further, the reaction was carried out in the same manner as in Example 6. The time required to introduce ethylene oxide was 7 hours. The amount of unreacted 1-dodecanol contained in the ethoxylate thus obtained was 4.0% (gas chromatography area%). Table 2 shows the results of the distribution of the degree of ethylene oxide addition polymerization of this ethoxylate obtained by gas chromatography.

[0040]

[Table 1]

[0041]

[Table 2]

[0042]

INDUSTRIAL APPLICABILITY The catalyst for producing an alkoxylate of the present invention can narrow the distribution of the degree of polymerization of alkylene oxide addition of the active hydrogen-containing organic compound alkoxylate produced in the reaction between the active hydrogen-containing organic compound and the alkylene oxide. Further, the residual amount of unreacted active hydrogen-containing organic compound and the by-product content can be reduced.

[Brief description of drawings]

FIG. 1 is a diagram showing a comparison of ethylene oxide addition polymerization degree distributions of ethoxylates obtained in Example 1 of the present invention and ethylene oxide addition polymerization degree distributions of ethoxylates obtained in Comparative Examples 2 and 3. The vertical axis represents the area% by gas chromatography of each ethoxylate component with respect to the total amount of ethoxylates, and the horizontal axis represents the number of moles of ethylene oxide added.

FIG. 2 is a diagram showing a comparison of ethylene oxide addition polymerization degree distributions of ethoxylates obtained in Example 2 of the present invention and ethylene oxide addition polymerization degree distributions of ethoxylates obtained in Comparative Example 2 and Comparative Example 3. The vertical axis represents the area% by gas chromatography of each ethoxylate component with respect to the total amount of ethoxylates, and the horizontal axis represents the number of moles of ethylene oxide added.

FIG. 3 is a diagram showing a comparison of ethylene oxide addition polymerization degree distributions of ethoxylates obtained in Example 3 of the present invention and ethylene oxide addition polymerization degree distributions of ethoxylates obtained in Comparative Examples 2 and 3. The vertical axis represents the area% by gas chromatography of each ethoxylate component with respect to the total amount of ethoxylates, and the horizontal axis represents the number of moles of ethylene oxide added.

FIG. 4 is a diagram showing a comparison of ethylene oxide addition polymerization degree distributions of ethoxylates obtained in Example 4 of the present invention and ethylene oxide addition polymerization degree distributions of ethoxylates obtained in Comparative Examples 2 and 3. The vertical axis represents the area% by gas chromatography of each ethoxylate component with respect to the total amount of ethoxylates, and the horizontal axis represents the number of moles of ethylene oxide added.

FIG. 5 is a diagram showing a comparison of ethylene oxide addition polymerization degree distributions of ethoxylates obtained in Example 5 of the present invention and ethylene oxide addition polymerization degree distributions of ethoxylates obtained in Comparative Examples 2 and 3. The vertical axis represents the area% by gas chromatography of each ethoxylate component with respect to the total amount of ethoxylates, and the horizontal axis represents the number of moles of ethylene oxide added.

Continuation of the front page (51) Int.Cl. ⁵ Identification code Office reference number FI technical display area C07C 43/11 7419-4H

Claims (1)

[Claims] 1. A method for reacting an active hydrogen-containing organic compound with an alkylene oxide, comprising a composite oxide of at least one selected from the group consisting of iron, nickel, cerium, and ytterbium and magnesium. A catalyst for producing an alkoxylate containing an active hydrogen-containing organic compound.