JP2000239231A - Method for producing unsaturated esters - Google Patents

Abstract

(57) [Problem] To provide a method for producing unsaturated esters. SOLUTION: General formula (1) (Wherein R ¹ , R ² , and R ³ are hydrogen, halogen, alkyl, alkenyl, aralkyl, aryl, and R ⁴ is alkyl or phenyl) and the general formula (2) R ⁵ OH (2) (wherein, R ⁵ is alkyl, aralkyl, aryl.)
A transesterification reaction of a hydroxy compound represented by the formula (3) in the presence of an alkoxide compound of a lanthanoid group metal A method for producing an unsaturated ester represented by the formula:

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a method for producing unsaturated esters.

[0002]

2. Description of the Related Art A transesterification reaction in which an ester compound reacts with a different compound containing another ester to obtain an ester compound different from the ester compound of the substrate is widely performed industrially as a method for synthesizing unsaturated esters. Have been done.
Various catalysts are known for promoting this transesterification reaction, and examples thereof include alkali metal alkoxides described in U.S. Pat. No. 2,744,884 and organotin compounds described in JP-A-56-104851. However, in order for these catalysts to exhibit activity, high temperature conditions such as heating and refluxing the reaction substrate are usually required, and side reactions such as polymerization of unsaturated esters and addition of substrate alcohol to unsaturated esters proceed. It was not always sufficient, for example, because it became easier.

[0003]

DISCLOSURE OF THE INVENTION The present invention provides a process for producing an unsaturated ester of interest under mild conditions by a transesterification reaction of the unsaturated ester with a corresponding hydroxy compound. It seeks to provide the law.

[0004]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, have reached the present invention. That is, the present invention relates to the general formula (1) (Wherein R ¹ , R ² and R ³ are each independently a hydrogen atom, a halogen atom, an optionally substituted alkyl group,
R ⁴ represents an optionally substituted alkenyl group, an optionally substituted aralkyl group or an optionally substituted aryl group, wherein R ⁴ has 1 to 10 carbon atoms which may be substituted;
Represents an alkyl group or a phenyl group which may be substituted. And an unsaturated ester represented by the general formula (2): R ⁵ OH (2) wherein R ⁵ is an optionally substituted alkyl group, an optionally substituted aralkyl group or a substituted A transesterification reaction of a hydroxy compound of formula (3) in the presence of an alkoxide compound of a lanthanoid group metal. (Wherein R ¹ , R ² , R ³ and R ⁵ have the same meanings as described above).

[0005]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. The present invention is characterized in that when producing an unsaturated ester (3) by a transesterification reaction, the unsaturated ester (1) and the hydroxy compound (2) are reacted in the presence of an alkoxide of a lanthanoid metal. In the present invention, La, Ce, Pr, N belonging to the lanthanoid group are used as catalysts.
d, Pm, Sm, Eu, Gd, Tb, Dy, Ho, E
At least one selected from the alkoxy compounds of r, Tm, Yb, and Lu can be used, but an industrially available La and Sm alkoxy compound is preferably used.

The alkoxide compound of a lanthanoid metal is, for example, a compound represented by the following general formula (4): Ln (OR ⁶ ) (OR ⁷ ) (OR ⁸ ) (4) (where Ln represents a lanthanoid metal element, and R ⁶ , R ⁷
And R ⁸ are the same or different and represent an alkyl group having 1 to 10 carbon atoms. )). R
⁶ , R ⁷ and R ⁸ include an alkyl group having 1 to 10 carbon atoms, which may be linear, branched or cyclic, for example, methyl, ethyl, n-propyl, i-propyl , N-butyl, i-butyl, t-butyl, n-pentyl, n-hexyl, n-octyl, cyclopropyl, cyclobutyl,
Cyclopentyl, cyclohexyl and the like can be mentioned. Further, they may combine with each other to form a divalent or trivalent alkoxide.

[0007] In addition, depending on the kind of the metal or the kind of the aliphatic hydrocarbon group, a polymer may be formed in addition to the monomer represented by the general formula (4), and these may be used in the present invention. .

[0008] As the alkoxide, methoxide, ethoxide, n-propoxide, i-propoxide, t-butoxide and the like are preferably used because of ease of preparation. More preferably, because it is soluble in the solvent described below, n-propoxide, i-propoxide, t-butoxide, more preferably that the catalyst preparation cost is inexpensive, because it is advantageous in production, etc. i-propoxide.

These lanthanide metal alkoxide catalysts can be prepared by a known method, and may be subjected to a reaction after isolation, or may be used as a solution after preparation. Furthermore, the alkoxide of the lanthanoid metal once prepared is reacted with the hydroxy compound (2) as a reaction raw material, and can be used as an alkoxide catalyst containing the hydroxy compound (2) as a reaction raw material.

Although the amount of the lanthanoid metal alkoxide compound is not particularly limited, it is generally 0.001 to 200 mol%, preferably 0.01 to 200 mol%, based on the unsaturated ester (1).
The range is about 20 mol%. After the reaction is completed, the lanthanoid metal alkoxide catalyst can be subjected to the reaction again by removing the solvent, products, and the like by ordinary means such as filtration and / or distillation. In addition, if a lanthanoid metal alkoxide catalyst is supported on a carrier such as a polymer, silica gel, or activated carbon, or a known method such as microencapsulation using a resin is used, the catalyst can be easily recovered and reused. .

The unsaturated ester used as a raw material in the present invention is represented by the general formula (1), wherein R ¹ , R ² and R ³ are each independently a hydrogen atom, a halogen atom or a halogen atom. An atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, an aralkyl group which may be substituted, and an aryl group which may be substituted.

Examples of the optionally substituted alkyl group include an alkyl group having 1 to 10 carbon atoms.
Any of a branched chain or a cyclic group may be used, and examples of the substituent include a halogen atom and an alkoxy group. Specific examples of the alkyl group which may be substituted include, for example,
Methyl, ethyl, n-propyl, i-propyl, n-butyl,
s-butyl, t-butyl, n-pentyl, n-hexyl, cyclohexyl, menthyl, chloromethyl, dichloromethyl,
Trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, 1-chloroethyl, 2-chloroethyl, 1-
Bromoethyl, 2-bromoethyl, 1,2-dichloroethyl,
1,2-dibromoethyl, 2,2,2-trichloroethyl, 2,2,2,
-Tribromoethyl, methoxymethyl, 2-methoxyethyl and the like.

[0013] Examples of the substituent of the optionally substituted alkenyl group include a halogen atom and a haloalkyl group.
Examples of the alkenyl group which may be substituted include vinyl,
1-methylvinyl, 1-propenyl, 2-methyl-1-propenyl, 2,2-dichlorovinyl, 2,2-dibromovinyl, 2-chloro-2-fluorovinyl, 2-chloro-2-trifluoromethylvinyl , 2-bromo-2-tribromomethylvinyl and the like.

Examples of the aralkyl group which may be substituted include benzyl, diphenylmethyl, phenylethyl, naphthylmethyl, naphthylethyl and the like, and these aromatic rings are substituted with the above-mentioned alkyl group, alkoxyl group, halogen atom and the like. What was done can be illustrated. Examples of the alkoxyl group substituted on the aromatic ring include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, t-butoxy, cyclohexoxy and the like.

Examples of the optionally substituted aryl group include, for example, phenyl, 1-naphthyl, 2-naphthyl and the like, and those in which these aromatic rings are substituted with the above-mentioned alkyl, alkoxyl, halogen and the like. Examples can be given.

In the unsaturated esters represented by the general formula (1), R ⁴ represents an alkyl group having 1 to 10 carbon atoms or a phenyl group which may be substituted. As the alkyl group having 1 to 10 carbon atoms, the same groups as those described for R ⁶ , R ⁷ and R ⁸ can be exemplified. Examples of the substituent of the optionally substituted phenyl group include the aforementioned alkyl group, alkoxy group and halogen atom.

Specific examples of the unsaturated ester (1) as a raw material include, for example, methyl acrylate, methyl crotonate, methyl methacrylate, methyl tiglate,
Methyl dimethyl acrylate, methyl 2-pentenoate, methyl 2-fluoroacrylate, methyl 3,3-dichloroacrylate, methyl 4,4-dichlorocrotonate, methyl 2-dichloromethyl acrylate, 5,5-dichloropentane Methyl -2,4-dienoate, methyl 3-benzylacrylate, methyl 2-benzylacrylate, methyl 2- (p-methylbenzyl) acrylate, methyl 2- (p-methoxybenzyl) acrylate, 2- ( p-
(Chlorobenzyl) methyl acrylate, methyl cinnamate, methyl p-methylcinnamate, methyl p-methoxycinnamate, methyl p-chlorocinnamate, ethyl acrylate, ethyl crotonate, ethyl methacrylate, ethyl tiglate, 3,3 -Ethyl dimethyl acrylate, ethyl 2-pentenoate, ethyl 2-fluoroacrylate, ethyl 3,3-dichloroacrylate, ethyl 4,4-dichlorocrotonate, ethyl 2-dichloromethyl acrylate, 5,5-dichloro Penta-
Ethyl 2,4-dienoate, ethyl 3-benzylacrylate, 2-
Ethyl benzyl acrylate, ethyl 2- (p-methylbenzyl) acrylate, ethyl 2- (p-methoxybenzyl) acrylate, ethyl 2- (p-chlorobenzyl) acrylate, ethyl cinnamate, ethyl p-methylcinnamate , Ethyl p-methoxycinnamate, ethyl p-chlorocinnamate, acrylic acid
i-propyl, i-propyl crotonate, i-propyl methacrylate, i-propyl tiglate, i-propyl 3,3-dimethylacrylate, i-propyl 2-pentenoate, i-propyl 2-fluoroacrylate, I-propyl 3,3-dichloroacrylate, i-propyl 4,4-dichlorocrotonate, i-propyl 2-dichloromethylacrylate, 5,5-dichloropenta-2,4-
I-propyl dienoate, i-propyl 3-benzylacrylate, i-propyl 2-benzylacrylate, i-propyl 2- (p-methylbenzyl) acrylate, i-propyl 2- (p-methoxybenzyl) acrylate Propyl, i-propyl 2- (p-chlorobenzyl) acrylate, i-propyl cinnamate, i-propyl p-methylcinnamate, i-propyl p-methoxycinnamate, i-propyl p-chlorocinnamate, acrylic acid t-butyl, t-butyl crotonate, t-butyl methacrylate,
T-butyl tiglate, t-butyl 3,3-dimethylacrylate, t-butyl 2-pentenoate, t-butyl 2-fluoroacrylate
Butyl, t-butyl 3,3-dichloroacrylate, t-butyl 4,4-dichlorocrotonate, t-butyl 2-dichloromethylacrylate, t-butyl 5,5-dichloropenta-2,4-dienoate T-butyl 3-benzyl acrylate, t-butyl 2-benzyl acrylate, t-butyl 2- (p-methylbenzyl) acrylate
Butyl, t-butyl 2- (p-methoxybenzyl) acrylate, t-butyl 2- (p-chlorobenzyl) acrylate, t-butyl cinnamate, t-butyl p-methylcinnamate, p-methoxycinnamate t-butyl, t-butyl p-chlorocinnamate, phenyl acrylate, phenyl crotonate, phenyl methacrylate, phenyl tiglate, phenyl 3,3-dimethylacrylate, phenyl 2-pentenoate, phenyl 2-fluoroacrylate, Phenyl 3,3-dichloroacrylate, phenyl 4,4-dichlorocrotonate, phenyl 2-dichloromethylacrylate, phenyl 5,5-dichloropenta-2,4-dienoate, phenyl 3-benzylacrylate, 2-phenyl Phenyl benzyl acrylate, phenyl 2- (p-methylbenzyl) acrylate, phenyl 2- (p-methoxybenzyl) acrylate, phenyl 2- (p-chlorobenzyl) acrylate, Phenyl oxalate, phenyl p-methylcinnamate, phenyl p-methoxycinnamate, phenyl p-chlorocinnamate and the like. Preferably, acrylic acid esters and methacrylic acid esters are used.

[0018] The hydroxy compound represented by the general formula (2) used in the present invention is an optionally substituted alkyl alcohol, an optionally substituted aralkyl alcohol or an optionally substituted aryl alcohol,
Examples of the substituent of the alkyl alcohol which may be substituted include an alkoxy group, a phenoxy group, a cyano group, a dialkylamino group, a halogen atom, a furyl group, a tetrahydrofuryl group, an ethylene oxide, and a hydroxy group. Specific examples of the alkyl alcohol which may be substituted include, for example, methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol,
n-butyl alcohol, s-butyl alcohol, t-butyl alcohol, n-pentyl alcohol, neopentyl alcohol, amyl alcohol, n-hexyl alcohol, n-
Octyl alcohol, n-decyl alcohol, cyclohexyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, 2-dimethylaminoethanol, 2-diethylaminoethanol, 2-cyanoethanol, 2-methoxyethanol, 2-ethoxyethanol, 2-phenoxyethanol, full Furyl alcohol, tetrahydrofurfuryl alcohol, glycidol, chloromethyl alcohol, dichloromethyl alcohol, trichloromethyl alcohol, bromomethyl alcohol, dibromomethyl alcohol, tribromomethyl alcohol, fluoromethyl alcohol, difluoromethyl alcohol, trifluoromethyl alcohol, fluoroethyl Alcohol, difluoroethyl alcohol, trifluoroethyl alcohol, tetrafluoroethyl Alcohol, pentafluoroethyl alcohol, perfluoropropyl alcohol,
Hexafluoroisopropyl alcohol, perfluorobutyl alcohol, perfluoropentyl alcohol,
Examples include perfluorohexyl alcohol, perfluorooctyl alcohol, perfluorodecyl alcohol, and the like.

Examples of the substituent of the aralkyl alcohol which may be substituted include an alkyl group, an alkoxy group, a phenoxy group, a nitro group, a cyano group and a halogen atom. Specific examples of the aralkyl alcohol which may be substituted include, for example, benzyl alcohol, 3-phenoxybenzyl alcohol, 2-hydroxy-2- (3-phenoxyphenyl) ethanenitrile, (2-methylphenyl) methyl alcohol, (3 -Methylphenyl) methyl alcohol, (4-methylphenyl) methyl alcohol, (2,3-dimethylphenyl) methyl alcohol, (2,4-dimethylphenyl) methyl alcohol, (2,5-dimethylphenyl)
Methyl alcohol, (2,6-dimethylphenyl) methyl alcohol, (3,4-dimethylphenyl) methyl alcohol, naphthylmethyl alcohol, anthracenyl methyl alcohol, 1-phenylethyl alcohol, 1- (1-naphthyl) ethyl alcohol , 1- (2-naphthyl) ethyl alcohol and haloaralkyl alcohols in which these are substituted with halogen such as fluorine, chlorine and bromine atoms; and in the above-mentioned haloaralkyl alcohol, halogen atoms are substituted with methoxy, ethoxy, n-propoxy, i-propoxy. , N-
Alkoxy aralkyl alcohol arbitrarily changed to butoxy, s-butoxy, t-butoxy and the like, cyano aralkyl alcohol, nitroaralkyl alcohol and the like.

The optionally substituted aryl alcohols include, for example, phenol, 1-naphthol, 2-naphthol and the like, and those in which these aromatic rings are substituted with an alkyl group, an alkoxy group, a halogen atom or the like.

The hydroxy compound (2) has a
Preferred are secondary or primary alcohols, and particularly preferred are primary alcohols.

[0022] The amount of the hydroxy compound (2) used is usually 1 equivalent or more based on the unsaturated ester (1), and may be used in excess if necessary, or used as a solvent. If desired, the unsaturated esters may be used in excess, or may be used as a solvent. Generally, after the reaction is completed, unreacted raw materials can be recovered by an operation such as distillation.

The reaction between the unsaturated ester (1) and the hydroxy compound (2) in the presence of a lanthanoid metal alkoxide compound is usually carried out in an atmosphere of an inert gas such as argon or nitrogen. The reaction can be carried out under any of normal pressure, increased pressure and reduced pressure. Preferably, the reaction is carried out under normal pressure or reduced pressure. Since the transesterification reaction is biased toward the raw material, alcohols derived from the unsaturated ester (1) of the raw material, which generally has a low boiling point, are taken out of the reaction system. It is preferable to carry out the reaction continuously while removing by a method such as distillation.

The reaction can be carried out without a solvent or in a solvent. Examples of the solvent used include halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, and hexane, heptane, octane and nonane. Aliphatic hydrocarbons, benzene, toluene, xylene, aromatic hydrocarbons such as chlorobenzene, diethyl ether,
Examples include ether solvents such as tetrahydrofuran. Also, by adding a solvent that causes azeotropic distillation with the alcohol derived from the unsaturated ester (1) as the raw material, only the alcohol can be continuously removed.

The reaction temperature is not particularly limited, but is preferably 0.
To 150 ° C, particularly preferably about 10 to 100 ° C, and it is preferable to use mild conditions in order to suppress side reactions.

Unsaturated esters (3) formed by such a reaction
The catalyst can be removed by washing with water or acidic water or the like, and can be easily separated from the reaction mixture by performing an operation such as distillation if necessary.

[0027]

According to the present invention, unsaturated esters (3) can be easily obtained under mild conditions, which is advantageous as an industrial production method.

[0028]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.

Example 1 In a 20-mL eggplant flask purged with nitrogen, 0.04 g (0.1 mmol) of triisopropoxysamarium (III), 1.72 g (20 mmol) of methyl acrylate, and 5.3 g (40 mmol) of 1-octanol were added. After that, the mixture was stirred at 25 ° C. for 2 hours. When the reaction mixture was analyzed by gas chromatography, the yield of 1-octyl acrylate was 5
0% (selectivity 72%).

Example 2 8.2 mg (0.03 mmol) of triisopropoxysilanetan (III), 511.8 mg (6 mmol) of methyl acrylate, and 1.554 g (12 mmol) of 1-octanol were added to a 20-mL eggplant flask purged with nitrogen. After
Stirred at 25 ° C. for 2 hours. When the reaction mixture was analyzed by gas chromatography, the yield of 1-octyl acrylate was 50% (selectivity 81%).

Example 3 In Example 2, triisopropoxysilanetan (III) was used.
Instead of 8.2 mg, tri-t-butoxysilanetan (III) 1
The reaction was carried out in the same manner as in Example 2 using 1.6 mg, and the yield of the obtained 1-octyl acrylate was 52%.
(Selectivity 80%).

Comparative Example 1 In Example 2, triisopropoxysilanetan (III)
When a reaction was carried out in the same manner as in Example 2 using 7.2 mg of dibutyltin oxide instead of 8.2 mg, the yield of 1-octyl acrylate was 1%.

Comparative Example 2 In Example 2, triisopropoxysilanetan (III)
Instead of 8.2 mg, 12.8 m of triphenyltin hydroxide
g, and the reaction was carried out in the same manner as in Example 2. As a result, the yield of 1-octyl acrylate was 1%.

Example 4 In a 20 mL eggplant-shaped flask purged with nitrogen, 39 mg (0.11 mmol) of tri-t-butoxysilanetan (III), 1143.8 mg (11.4 mmol) of methyl methacrylate,
3.03 g of 2-ethylhexyl alcohol (23 mmo
After adding l), the mixture was stirred at 25 ° C for 2 hours. When the reaction mixture was analyzed by gas chromatography, the yield of 2-ethylhexyl methacrylate was 67% (selectivity 98%).
%)Met.

Comparative Example 3 In Example 4, tri-t-butoxysilanetan (III) 3
When the reaction was carried out in the same manner as in Example 4 using 7.5 mg of sodium ethoxide instead of 9 mg, the yield of the obtained 2-ethylhexyl methacrylate was 19% (selectivity 99%).

Example 5 11.4 mg (0.03 mmol) of tri-t-butoxysilanetan (III), 578.1 mg (5.8 mmol) of methyl methacrylate were placed in a 20 mL eggplant-shaped flask purged with nitrogen.
1.19 g of tetrahydrofurfuryl alcohol (12 m
mol), and the mixture was stirred at 25 ° C for 2 hours. When the reaction mixture was analyzed by gas chromatography, the yield of tetrahydrofurfuryl methacrylate was 32% (selectivity 93%).

Comparative Example 4 In Example 5, tri-t-butoxysilanetan (III) 1
When the reaction was carried out in the same manner as in Example 5 except that 2.1 mg of sodium ethoxide was used instead of 1.4 mg, the yield of the obtained tetrahydrofurfuryl methacrylate was 15%.
(Selectivity 72%).

Example 6 30.4 mg (0.10 mmol) of tri-i-propoxysilanetan (III) was placed in a 20-mL eggplant flask purged with nitrogen.
2.06 g (20.6 mmol) of methyl methacrylate,
1.18 g of 2-diethylaminoethanol (10 mmol
After l) was added, the mixture was stirred at 100 ° C for 4 hours. When the reaction mixture was analyzed by gas chromatography, the yield of diethylaminoethyl methacrylate was 66% (selectivity 9
3%).

Comparative Example 5 The procedure of Example 6 was repeated except that tri-i-propoxysilanetan (III) was used.
Instead of 30.4mg, 6.3mg of sodium methoxide
When the reaction was carried out in the same manner as in Example 6, the yield of the obtained diethylaminoethyl methacrylate was 47%.
(Selectivity 92%).

Comparative Example 6 In Example 6, tri-i-propoxysilanetan (III)
When 23.6 mg of dibutyltin oxide was used instead of 30.4 mg, and the reaction was carried out in the same manner as in Example 6, the yield of the obtained diethylaminoethyl methacrylate was 38%.
(Selectivity 88%).

Example 7 In a 20 mL eggplant-shaped flask purged with nitrogen, 48.5 mg (0.15 mmol) of tri-i-propoxysilanetan (III) were added.
5.91 g (59.0 mmol) of methyl methacrylate,
After adding 0.93 g (15 mmol) of ethylene glycol, the mixture was stirred at 100 ° C. for 4 hours. When the reaction mixture was analyzed by gas chromatography, the yield of ethylene glycol dimethacrylate was 46% (selectivity 48%).

Comparative Example 7 To a 20 mL eggplant flask purged with nitrogen, 21.8 mg (0.40 mmol) of sodium methoxide, 3.12 g (31.1 mmol) of methyl methacrylate, and 0.48 g (7.7 mmol) of ethylene glycol were added. Later, 10
Stirred at 0 ° C. for 4 hours. When the reaction mixture was analyzed by gas chromatography, the yield of ethylene glycol dimethacrylate was 22% (selectivity 23%).

Comparative Example 8 In Example 7, tri-i-propoxysilanetan (III)
When 36.1 mg of dibutyltin oxide was used instead of 48.5 mg, and the reaction was carried out in the same manner as in Example 6, the target substance, diethylaminoethyl methacrylate, was not obtained.

Continued on the front page (72) Inventor Kazunori Iwakura 2-10-1, Tsukahara, Takatsuki-shi, Osaka Sumitomo Chemical Co., Ltd. F-term (reference) 4H006 AA02 AC48 BA08 BA32 KA03 KC14 4H039 CD10 CD40 CD90 CE10

Claims (11)

[Claims] [Claim 1] General formula (1) (Wherein R ¹ , R ² and R ³ are each independently a hydrogen atom, a halogen atom, an optionally substituted alkyl group,
R ⁴ represents an optionally substituted alkenyl group, an optionally substituted aralkyl group or an optionally substituted aryl group, wherein R ⁴ has 1 to 10 carbon atoms which may be substituted;
Represents an alkyl group or a phenyl group which may be substituted. And R ⁵ OH (2) wherein R ⁵ is an alkyl group which may be substituted, an aralkyl group which may be substituted or A transesterification reaction of a hydroxy compound of formula (3) in the presence of an alkoxide compound of a lanthanoid group metal. (Wherein, R ¹ , R ² , R ³ and R ⁵ have the same meanings as described above). Wherein the alkoxide compound of the lanthanide group metal has the general formula ^{(4) Ln (OR 6)} (OR 7) (OR 8) (4) ( wherein, Ln represents a lanthanoid metal element, R ^6, R ⁷
And R ⁸ are the same or different and represent an alkyl group having 1 to 10 carbon atoms. 2. The method according to claim 1, which is a compound represented by the formula: 3. The method according to claim 1, wherein the lanthanoid metal is La or Sm. 4. The alkanoate compound of a lanthanoid metal is L
The production method according to claim 1, wherein the production method is a (OiPr) ₃ , La (OtBu) ₃ or Sm (OiPr) ₃ . 5. The production method according to claim 1, wherein R ^{4 of the} unsaturated ester represented by the general formula (1) is methyl or ethyl. 6. The method according to claim 1, wherein the unsaturated ester represented by the general formula (1) is an acrylate or a methacrylate. 7. The method according to claim 1, wherein the hydroxy compound represented by the general formula (2) is a primary or secondary alcohol. 8. The production method according to claim 1, wherein the hydroxy compound represented by the general formula (2) is a primary alcohol. 9. The production method according to claim 1, wherein the alkoxide compound of the lanthanoid metal is reused. 10. The method according to claim 1, wherein the lanthanoid metal alkoxide compound is a microencapsulated lanthanoid metal alkoxide compound. 11. The production method according to claim 1, wherein the lanthanoid metal alkoxide compound is a lanthanoid metal alkoxide compound supported on a polymer, silica gel or activated carbon.