JP2002265416A - Method of decomposing ether - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method of simply and easily decomposing ether compounds. SOLUTION: The ether compound represented by general formula (I): R<2> -O-R<1> (wherein R<1> and R<2> are each a hydrocarbon group that has a molecular weight of <=1,000,000 and may bear oxygen atoms and the like in the main chain) is decomposed by breaking the C-O bonds in ether compounds in the presence of a halide of one metal selected from the groups 5-6 in the periodic table, arbitrarily in addition of a trapping agent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for decomposing an ether compound, and more particularly, to a method for decomposing C in an ether compound.
The present invention relates to a method for decomposing an ether compound by breaking an —O bond.

[0002]

BACKGROUND OF THE INVENTION Ether compounds, particularly polyether compounds, are relatively stable and are widely used as materials for cushions and the like.

[0003] In recent years, the problem of treating industrial waste has become an important social issue. In particular, regarding the treatment of polymer products, it has become increasingly important not only to incinerate this as fuel, but also to decompose it into lower-molecular compounds, recover them, and reuse them effectively. I have. However, it was not easy to decompose an ether compound having a stable ether bond.

On the other hand, if thermal decomposition is performed to decompose into low molecular weight compounds, this thermal decomposition reaction requires a high-temperature and high-pressure thermal decomposition apparatus. It costs money.

[0005] Therefore, if a method for decomposing an ether compound and converting it to a relatively low-molecular compound can be found under normal pressure and not so high temperature, equipment such as a thermal decomposition device is not required, and low A low molecular weight compound can be easily and easily obtained at low cost from an ether compound, and its industrial utility value is enormous.

An object of the present invention is to easily and easily decompose an ether compound.

[0007]

SUMMARY OF THE INVENTION The present inventors have determined that ether bonds can be stoichiometrically or catalytically cleaved in the presence of a metal halide containing a metal belonging to Group 5 or 6 of the periodic table. Found and led to the present invention.

Namely, in the present invention, an ether compound ^{R 2 -O-R 1 (I} ) ( wherein represented by the following formula (I), R ¹ and R ² are each, independently of one another, identical or different Has a molecular weight of 1,000,000 or less, may have a substituent, and contains at least one hetero atom selected from the group consisting of an oxygen atom, a nitrogen atom, a sulfur atom and a silicon atom in the main chain. A hydrocarbon group which may be a hydrocarbon group.), And is decomposed by cutting a C—O bond in an ether compound in the presence of a metal halide containing a metal belonging to Group 5 or 6 of the periodic table. A method for decomposing an ether compound is provided.

In the present invention, the metal of Groups 5 and 6 of the periodic table is preferably Mo, W, Nb or Ta.

In the above decomposition method, a trapping agent may be further added. Further, the trapping agent has the following formula (I)
R ³ —C (＝ O) —Y (II) which is an acid halide represented by I) (wherein R ³ is a hydrogen atom; a C ₁ -C ₂₀ hydrocarbon which may have a substituent) A group; a C _1- which may have a substituent;
C ₂₀ alkoxy group; C ₆ -C optionally having substituent (s)
_{20 an} aryloxy group; an amino group which may have a substituent; a silyl group or a hydroxyl group which may have a substituent, and Y is a halogen atom. Is preferred.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, an ether compound represented by the following formula (I) is represented by R ² -OR ¹ (I) (wherein R ¹ and R ² have the above-mentioned meanings) In the presence of a metal halide containing a metal of Groups 5 and 6 of the periodic table,
There is provided a method for decomposing an ether compound, which is decomposed by breaking a C—O bond in the ether compound.

R ¹ and R ² are each independently of the other
The same or different hydrocarbon groups having a molecular weight of 1,000,000 or less and optionally having a substituent.

As used herein, a hydrocarbon group may be saturated or unsaturated, acyclic, or saturated or unsaturated, cyclic. When the hydrocarbon group is acyclic, it may be linear or branched. Hydrocarbon groups include alkyl groups, alkenyl groups, alkynyl groups, allyl groups, alkyldienyl groups, polyenyl groups, aryl groups,
Examples include an alkylaryl group, an arylalkyl group, a cycloalkyl group, a cycloalkenyl group, a (cycloalkyl) alkyl group, and the like.

The molecular weight of R ¹ and R ² is 1,000,000 or less, preferably 500,000 or less, more preferably 20,000,000 or less.
Less than 10,000. In addition, in this specification, a molecular weight means the weight average molecular weight.

A substituent may be introduced into R ¹ and R ² , for example, a C ₁ -C ₁₀ hydrocarbon group, a C ₁ -C ₁₀ alkoxy group, a C ₆ -C _{10 10} Examples include an aryloxy group, an amino group, a hydroxyl group or a silyl group.

R ¹ and R ² may contain at least one hetero atom selected from the group consisting of an oxygen atom, a nitrogen atom, a sulfur atom and a silicon atom in the main chain. For example, a polymer composed of a monomer containing at least one hetero atom selected from the group consisting of an oxygen atom, a nitrogen atom, a sulfur atom and a silicon atom can be mentioned.

Examples of the ether compound represented by the above formula (I) include polymers, copolymers and terpolymers having one or more ether bonds in the main chain, and such polymers include thermoplastic resins. polymer,
Thermosetting polymers, engineering plastics,
Conductive polymers can be mentioned without limitation.

The ether compound represented by the above formula (I) is preferably a polyether.

In the method for decomposing an ether bond of the present invention, a metal halide containing a metal belonging to Group 5 or 6 of the periodic table is used.

The metals belonging to Groups 5 and 6 of the periodic table include, for example, Cr, Mo, W, V, Nb, and Ta. Mo, W, Nb, and Ta are preferred.

In the present specification, a metal halide is a compound having a metal halide bond, and includes a complex. For example, NbX ₅ , TaX ₅ , Mo
X ₂ , MoX ₃ , MoX ₄ , MoX ₅ , MoX ₆ , WX ₂ , W
X ₃ , WX ₄ , WX ₅ , and WX ₆ (wherein, X represents a halogen atom such as a chlorine atom, a bromine atom, a fluorine atom, an iodine atom, etc.) and complexes thereof can be preferably exemplified. , Molybdenum (V) chloride, tungsten (VI) chloride, niobium (V) chloride, tantalum (V) chloride, and complexes thereof are particularly preferred.

The amount of the metal halide is from 0.0001 mol to 100 mol, preferably from 0.01 mol to 10 mol, more preferably from 0.1 mol to 100 mol, per 1 mol of the ether compound (I). It is 2 mol, particularly preferably about 0.1 mol to about 1 mol.

As a method for decomposing the ether compound represented by the above formula (I), typically, a metal halide is added to a solution of the ether compound represented by the above formula (I), followed by stirring. However, the order of adding the ether compound (I) and the metal halide is not limited. The ether compound (I) and the metal halide may be simultaneously added to the solvent, the metal halide may be added after the addition of the ether compound (I), or after the metal halide is added, An ether compound (I) may be added.

In this method for decomposing an ether compound,
The metal halide does not participate in the reaction as a catalyst, but stoichiometrically participates in the reaction, and the ether compound (I)
It seems to have reacted with to produce an intermediate.

For example, the following scheme is proposed as a reaction mechanism.

[0026]

Embedded image (In the formula, R ¹ and R ² have the above-mentioned meanings. M is a metal belonging to Groups 5 and 6 of the periodic table, X is a halogen atom, and n represents an integer of 1 to 6.) The ether compound (I) reacts with a metal halide to cleave the C—O bond in the ether compound, and the compound of the above formula (IV)
And a complex represented by the above formula (V).

When an ether bond is present in R ¹ and / or R ² , it is considered that such an ether bond is cleaved by the above-mentioned metal halide by a similar reaction.

This reaction mechanism is only a hypothesis, and the present invention is not limited to this reaction mechanism.

The reaction is preferably carried out at -100 ° C to 300 ° C.
, And particularly preferably -80 ° C to 200 ° C.
C., more preferably in the temperature range of 0.degree. C. to 200.degree. The pressure is, for example, from 0.1 bar to 250
It is in the range of 0 bar, preferably in the range of 0.5 bar to 10 bar.

As the solvent, a solvent capable of dissolving the ether compound represented by the above formula (I) is preferable.
As the solvent, an aliphatic or aromatic organic solvent is used. Ether solvents such as tetrahydrofuran or diethyl ether; halogenated hydrocarbons such as dichloroethane and methylene chloride; halogenated aromatic hydrocarbons such as o-dichlorobenzene; amides such as N, N-dimethylformamide; dimethylsulfoxide; Sulfoxide; aromatic hydrocarbons such as benzene and toluene are used.

In the present invention, when decomposing the ether compound, a trapping agent may be further added. By adding a trapping agent, the catalytic reaction of the ether compound can be allowed to proceed by using a catalytic amount of the above metal halide. It is possible to prevent the addition of a further polymer to the compound, to prevent the ether compound or the compound generated after decomposition from aggregating, or
There are advantages such as the ability to regenerate the metal halide in the course of the reaction.

As the trapping agent, for example, an organic halogen compound is preferable, and more preferably, the following formula (II)
The acid halides represented by I) can be mentioned. R ³ —C (＝ O) —Y (III) R ³ is a hydrogen atom; C _{1 to} C ₂₀ which may have a substituent.
Hydrocarbon group; C ₁ -C ₂₀ alkoxy group optionally having a substituent; C ₆ -C ₂₀ aryloxy group optionally having a substituent; amino group optionally having a substituent A silyl group or a hydroxyl group which may have a substituent.

In this specification, C₁~ C₂₀The hydrocarbon group is
It may be saturated or unsaturated, acyclic,
Or an unsaturated cyclic group. C₁~ C₂₀Hydrocarbon
When the radical is acyclic, it may be linear or branched.
Is also good. C₁~ C₂₀Hydrocarbon groups include C₁~ C₂₀Alkyl
Group, C_Two~ C₂₀Alkenyl group, C_Two~ C₂₀Alkynyl group,
C_Three~ C₂₀Allyl group, C_Four~ C₂₀Alkyldienyl group, C
_Four~ C₂₀Polyenyl group, C₆~ C₁₈Aryl group, C₆~ C
₂₀Alkylaryl group, C₆~ C₂₀Arylalkyl
Group, C_Four~ C₂₀Cycloalkyl group, C_Four~ C₂₀Cycloal
Kenyl group, (C _Three~ C_TenCycloalkyl) C₁~ C_TenAl
And a kill group.

C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂₀ alkynyl, C ₃ -C ₂₀ allyl, C
₄ -C ₂₀ alkadienyl group, and, C ₄ -C ₂₀ polyenyl group, respectively, C ₁ -C ₁₀ alkyl group, C ₂ -C ₁₀ alkenyl group, C ₂ -C ₁₀ alkynyl group, C ₃ -C ₁₀ allyl group, C ₄ -C ₁₀ alkadienyl group, and is preferably a C ₄ -C _{1 0} polyenyl group.

C ₆ -C ₁₈ aryl group, C ₆ -C ₂₀ alkylaryl group, C ₆ -C ₂₀ arylalkyl group, C ₄ -C ₂₀
Cycloalkyl group, and, C ₄ -C ₂₀ cycloalkenyl group, each, C ₆ -C ₁₀ aryl group, C ₆ -C ₁₂ alkylaryl group, C ₆ -C ₁₂ arylalkyl group, C ₄ ~
It may be a C ₁₀ cycloalkyl group or a C ₄ -C ₁₀ cycloalkenyl group.

Examples of optionally substituted alkyl groups useful in the practice of the present invention include, but are not limited to, methyl, ethyl, propyl, n-butyl,
There are t-butyl, dodecanyl, trifluoromethyl, perfluoro-n-butyl, 2,2,2-trifluoroethyl, benzyl, 2-phenoxyethyl and the like.

Examples of optionally substituted aryl groups useful in the practice of the present invention include, but are not limited to, phenyl, 2-tolyl, 3-tolyl, 4-
Tolyl, naphthyl, biphenyl, 4-phenoxyphenyl, 4-fluorophenyl, 3-carbomethoxyphenyl, 4-carbomethoxyphenyl and the like.

Examples of optionally substituted alkoxy groups useful in the practice of the present invention include, but are not limited to, methoxy, ethoxy, 2-methoxyethoxy, t-butoxy, and the like.

Examples of an optionally substituted aryloxy group useful in the practice of the present invention include, but are not limited to, phenoxy, naphthoxy, phenylphenoxy, 4-methylphenoxy, 2-tolyloxy , 3-tolyloxy, 4-tolyloxy, naphthyloxy, biphenyloxy, 4-phenoxyphenyloxy, 4-fluorophenyloxy, 3-carbomethoxyphenyloxy, 4-carbomethoxyphenyloxy and the like.

A substituent may be introduced into the C ₁ -C ₂₀ hydrocarbon group, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryloxy group, amino group and silyl group. Examples thereof include a C ₁ -C ₁₀ hydrocarbon group, a C ₁ -C ₁₀ alkoxy group, a C ₆ -C ₁₀ aryloxy group, an amino group, a hydroxyl group and a silyl group.

Examples of the optionally substituted amino group useful in the practice of the present invention include, but are not limited to, amino, dimethylamino, methylamino, methylphenylamino, phenylamino and the like. is there.

The silyl group which may be substituted and which is useful in the practice of the present invention includes, but is not limited to, trimethylsilyl, triethylsilyl, trimethoxysilyl, triethoxysilyl, diphenylmethylsilyl and triphenylsilyl. Examples include phenylsilyl, triphenoxysilyl, dimethylmethoxysilyl, dimethylphenoxysilyl, and methylmethoxyphenyl.

Y is a halogen atom. Examples of the halogen atom include a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom, and preferably a chlorine atom and a bromine atom. In the method for decomposing an ether compound of the present invention, a halogen atom contained in the metal halide is preferable from the viewpoint of regenerating and using the metal halide.

The amount of the trapping agent depends on the amount of the ether compound (I)
It is 0.1 mol to 100 mol, preferably 0.5 mol to 50 mol, and more preferably 0.1 mol to 1 mol.
The amount is from 5 mol to 2 mol, particularly preferably about 1 mol.

As a method for decomposing the ether compound represented by the above formula (I) using a trapping agent, typically,
A trapping agent such as a metal halide or an acid halide is added to a solution of the ether compound represented by the above formula (I), and the mixture is stirred. However, the ether compound (I), the metal halide and the trapping agent may be added simultaneously to the solvent, or after adding the ether compound (I),
The metal halide and the trapping agent may be added simultaneously, or the metal halide may be added after the addition of the ether compound (I), and then the trapping agent may be added.

In the method for decomposing the ether compound,
By using an acid halide as a trapping agent, the metal halide appears to participate in the reaction as a catalyst.

For example, the following scheme is proposed as a reaction mechanism.

[0048]

Embedded image (Wherein, R ¹ , R ² , R ³ and Y have the above meanings.
M is a metal of Groups 5 and 6 of the periodic table, and X is a halogen atom. n shows the integer of 1-6. The ether compound (I) reacts with a metal halide to cleave the C—O bond in the ether compound, and the compound of the formula (IV)
And a complex represented by the above formula (V). Next, the acid halide (II) reacts with the complex (V) to produce an ester compound (VI) and a metal halide. According to this decomposition method, when X = Y, the metal halide is regenerated and can be used again for the decomposition reaction.

When an ether bond is present in R ¹ and / or R ² , it is considered that such an ether bond is cleaved by the above-mentioned metal halide and acid halide by a similar reaction.

This reaction mechanism is merely a hypothesis, and the present invention is not limited to this reaction mechanism.

The reaction is preferably carried out at -100 ° C to 300 ° C.
, And particularly preferably -80 ° C to 200 ° C.
C., more preferably in the temperature range of 0.degree. C. to 200.degree. The pressure is, for example, from 0.1 bar to 250
It is in the range of 0 bar, preferably in the range of 0.5 bar to 10 bar.

As the solvent, a solvent capable of dissolving the ether compound represented by the above formula (I) is preferable.
As the solvent, an aliphatic or aromatic organic solvent is used. Ether solvents such as tetrahydrofuran or diethyl ether; halogenated hydrocarbons such as dichloroethane and methylene chloride; halogenated aromatic hydrocarbons such as o-dichlorobenzene; amides such as N, N-dimethylformamide; dimethylsulfoxide; Sulfoxide; aromatic hydrocarbons such as benzene and toluene are used.

[0053]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below based on embodiments.
However, the present invention is not limited to the following examples.

All reactions were performed under a nitrogen atmosphere. Dibutyl ether is dried over lithium aluminum halide, tetrahydrofuran is dried over sodium phenylmethylketyl, and 1,2-dichloroethene is P ₂
And dried at O _5. Other materials were used as they were.

The ¹ H-NMR and ¹³ C-NMR spectra were 25
The temperature was measured using a Bruker ARX-apparatus at 0 ° C using a deuterated chloroform solution (containing 1% of TMS) as an internal standard.
Gas chromatographic analysis was performed on silica glass capillary columns SHIMADZU CBP1-M25-O25 and SHIMADZU C-R6A-Chrom
The measurement was performed with a SHIMADZU GC-14A gas chromatograph equipped with an atopac integrator. Single crystal X-ray diffraction was measured using an Enraf-Nonius CAD4 diffractometer with molybdenum or copper electrodes.

Example 1 n-butyl benzoate molybdenum (V) chloride (0.1 mmol, 27 mg), dichloroethane
(DCE) (5 ml) in dibutyl ether (1 mmol,
130 mg) and benzoyl chloride (1 mmol, 141 mg). The reaction mixture was stirred at 80 ° C. for 3 hours. 3 N HCl was added to terminate the reaction, and column chromatography was performed using silica gel as a packing material to obtain the title compound. Colorless liquid. Isolation yield 75%.

¹ H NMR (CDCl ₃ , Me ₄ Si): δ 0.98 (t, J =
7.4 Hz, 3H), 1.44-1.53 (m, 2H), 1.72-1.78 (m, 2H),
4.33 (t, J = 6.6 Hz, 2H), 7.35 (t, J = 7.7 Hz, 2
H), 7.52-7.56 (m, 1H), 8.03-8.04 (m, 2H); ¹³ C NMR
(CDCl ₃ , Me ₄ Si): δ 13.77,19.30, 30.28, 64.84, 12
8.32 (2C), 129.55 (2C), 130.58, 132.79, 166.70. High resolution mass spectrometer Calculated C ₁₁ H ₁₄ O ₂ 178.0993.

The following scheme is considered as a reaction mechanism in Example 1.

[0059]

Embedded image This reaction mechanism is merely a hypothesis, and the present invention is not limited to this reaction mechanism.

Example 2 n-Butyl caproate The same procedure as in Example 1 was performed. However, instead of benzoyl chloride, caproyl chloride is used and the reaction mixture is
Stirred for hours. Colorless liquid, isolation yield 78%.

¹ H NMR (CDCl ₃ , Me ₄ Si): δ 0.87-0.97
(m, 6H), 1.22-1.85 (m, 10H), 2.29 (t, J = 7.5 Hz, 2
H), 4.07 (t, J = 6.7 Hz, 2H); ¹³ C NMR (CDCl ₃ , Me ₄ Si
): δ 13.72, 13.92, 19.17, 22.33, 24.73, 30.73, 3
1.35, 34.39, 64.12, 174.05. High resolution mass spectrometry calculated value C ₁₀ H ₂₀ O ₂ 172.1462.

Example 3 n-octyl benzoate The same procedure as in Example 1 was performed. However, dioctyl ether was used instead of dibutyl ether, and the reaction mixture was stirred for 1 hour. Colorless liquid.

¹ H NMR (CDCl ₃ , Me ₄ Si): δ 0.88 (t, J =
6.8 Hz, 3H), 1.28-1.47 (m, 10H), 1.69-1.80 (m, 2
H), 4.31 (t, J = 6.7 Hz, 2H), 7.41-7.45 (m, 3H), 7.4
8-7.57 (m, 1H), 8.04-8.06 (m, 2H); ¹³ C NMR (CDCl ₃ ,
Me ₄ Si): δ 14.11, 22.67,26.08, 28.75, 29.23, 2
9.28, 31.82, 65.15, 128.32 (2C), 129.55 (2C), 130.5
7, 132.79, 166.70. High-resolution mass spectrometer calculated value C ₁₅ H
₂₂ O ₂ 234.1619.

Example 4 n-octyl caproate The same procedure as in Example 1 was performed. However, dioctyl ether was used instead of dibutyl ether, and caproyl chloride was used instead of benzoyl chloride. Colorless liquid.

¹ H NMR (CDCl ₃ , Me ₄ Si): δ 0.88 (t, J =
6.8 Hz, 3H), 0.90 t, J = 6.6 Hz), 1.26-1.32 (m,
16H), 1.57-1.66 (m, 2H), 2.29 (t, J = 7.5, 2
H), 4.06 (t, J = 6.7 Hz); ¹³ C NMR (CDCl ₃ , Me ₄ Si):
δ 13.92, 14.09, 22.34, 22.65, 24.73, 25.95, 28.
68, 29.22 (2C), 35.35, 31.80, 34.40, 64.42, 174.0
4. High resolution mass spectrometer Calculated value C ₁₄ H ₂₈ O ₂ , 228.2088
Found 229.2167.

Example 5 Methyl benzoate The same procedure as in Example 1 was performed. However, t-butyl methyl ether was used instead of dibutyl ether, and the reaction mixture was stirred at 50 ° C. for 1 hour. Colorless liquid, isolation yield 76
%.

¹ H NMR (CDCl ₃ , Me ₄ Si): δ 3.88 (s, 3
H), 7.41 (m, J = 7.7 Hz, 2H), 7.50-7.54 (m, 1H), 8.
02-8.04 (m, 2H); ¹³ C NMR (CDCl ₃ , Me ₄ Si): δ 52.0
5, 128.36 (2C), 129.58 (2C), 130.17, 132.91, 167.0
6. High resolution mass spectrometer Calculated _{C 8 H 8 O 2, 136.0524} .

Example 6 Propyl caproate The same procedure as in Example 1 was performed. However, allyl propyl ether was used instead of dibutyl ether, and caproyl chloride was used instead of benzoyl chloride. The reaction mixture was stirred for 1 hour. Colorless liquid, isolation yield 81%.

¹ H NMR (CDCl ₃ , Me ₄ Si): δ 0.90 (t, J =
6.8 Hz, 3H), 0.94 (t, J = 7,4 Hz, 3H), 1.27-1.34 (m, 4
H), 1.61-1.68 (m, 4H), 2.30 (t, J = 7.5 Hz, 2H), 4.0
3 (t, J = 6,7 Hz , 2H); 13 C NMR (CDCl 3, Me 4 Si): δ
10.43, 13.94, 22.06, 22.38, 24.76, 31.38, 34.40,
65.87, 174.07. High resolution mass spectrometer Calculated value C ₉ H ₁₈ O ₂ ,
158.1306.

Example 7 2-Propinyl caproate The same procedure as in Example 1 was performed. However, allyl trimethylsilyl ether was used instead of dibutyl ether, and caproyl chloride was used instead of benzoyl chloride. Colorless liquid.

¹ H NMR (CDCl ₃ , Me ₄ Si): δ 0.88 (t, J =
6.8 Hz, 3H), 1.25-1.34 (m, 4H), 1.58-1.67 (m, 2H),
2.32 (t, J = 7.5 Hz, 2H), 4.56 (d, J = 5.8Hz, 2H),
5.22 (dd, J ₁ = 10.4 Hz, J ₂ = 1.1 Hz, 1H), 5.30 (dd,
J ₁ = 17.2 Hz, J ₂ = 1.1 Hz, 1H), 5.90 (ddt, J ₁ = 1
7.2 Hz, J ₂ = 10.4 Hz, J ₃ = 7.5, 1H); ¹³ C NMR (CDCl
₃ , Me ₄ Si): δ 13.90, 22.31, 24.64, 31.30, 34.2
5, 64.92, 118.07, 132.34, 173.55. High resolution mass spectrometer Calculated C ₉ H ₁₆ O ₂ , 156.1149.

Example 8 butyl benzoate The same procedure as in Example 1 was performed. However, in place of molybdenum chloride (V), tungsten chloride (VI) was used.

Example 9 Butyl benzoate The same procedure as in Example 1 was performed. However, instead of molybdenum (V) chloride, niobium (V) chloride was used and the reaction mixture was used.
Stirred for 24 hours.

Example 10 Butyl benzoate The same procedure as in Example 1 was performed. However, tantalum (V) chloride was used instead of molybdenum (V) chloride, and the reaction mixture was stirred for 6 hours.

Table 1 shows the yields of Examples 1 to 10. The yield indicates the GC yield. Isolation yields are given in parentheses.

[0076]

[Table 1]

Example 11 n-Butyl valerate The procedure was performed in the same manner as in Example 1. However, valeryl chloride was used instead of benzoyl chloride. Colorless liquid. 32% isolated yield.

[0078]¹H NMR (CDCl_Three, Me_FourSi) δ 0.94 (t, J =
7.4 Hz, 3H), 1.20 (s, 9H), 1.36-1.42 (m, 2H), 1.58
-1.63 (m, 2H), 4.06 (t, J = 6.6 Hz, 2H).¹³C NMR
(CDCl _Three, Me_FourSi) δ 13.75, 19.19, 27.22 (3C), 30.72,
 38.75, 64.19, 178.68. High Resolution Mass Spectrometer Calculated
C₉H₁₈O_Two: 158.1307.

[0079]

According to the method of the present invention, an ether compound can be easily decomposed.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07C 29/68 C07C 29/68 C08L 71/00 C08L 71/00

Claims (4)

[Claims] 1. An ether compound represented by the following formula (I): R ² —O—R ¹ (I) (wherein R ¹ and R ² are each independently of the same or different and have a molecular weight of Is 1,000,000 or less, and may have a substituent, and the main chain contains at least one hetero atom selected from the group consisting of an oxygen atom, a nitrogen atom, a sulfur atom and a silicon atom. It is a good hydrocarbon group.) In the presence of a metal halide containing a metal belonging to Groups 5 and 6 of the periodic table, the ether compound is decomposed by breaking a C—O bond in the ether compound. Disassembly method. 2. The metal of Groups 5 and 6 of the periodic table is Mo, W,
The method for decomposing an ether compound according to claim 1, wherein the method is Nb or Ta. 3. The method for decomposing an ether compound according to claim 1, wherein a trapping agent is further added. 4. The method according to claim 1, wherein the trapping agent is an acid halide represented by the following formula (II): R ³ —C (＝ O) —Y (II) wherein R ³ is a hydrogen atom; and C ₁ optionally -C ₂₀ hydrocarbon group; which may have a substituent group C ₁ ~
C ₂₀ alkoxy group; C ₆ -C optionally having substituent (s)
_{20 an} aryloxy group; an amino group which may have a substituent; a silyl group or a hydroxyl group which may have a substituent, and Y is a halogen atom. A method for decomposing an ether compound according to claim 3.