WO2015041471A1 - Method for preparing alkanol - Google Patents

Abstract

The present application relates to a method and an apparatus for preparing alkanol, the method and apparatus according to the present application improving the preparation process to be more economical and stable, and allowing the mass production of alkanol.

Description

Method for preparing alkanol

The present application relates to a method and apparatus for producing alkanol.

Alkanols, such as n-butanol, are used in a variety of applications as solvents and intermediates in the chemical industry. For example, n-butanol is used as a raw material for a solvent, butyl acetate, a medicine, a perfume, a plasticizer, and a stabilizer.

In the production of the alkanol, problems such as process conditions and production costs remain a very important problem. For example, in the conventional alkanol production process, a hydrogenation process for reducing an aldehyde group using a hydrogen gas of high temperature and high pressure is required, and therefore, expensive process equipment is required, and there is also a problem in process stability. Existed.

Therefore, there is a need for a process for producing the alkanol, which is more stable and can reduce the process investment cost. In addition, in order for the alkanol to be used in various industrial fields, a process capable of mass production is required.

The present application aims to provide a method and apparatus for producing alkanol.

The present application relates to a method for preparing alkanol. According to the above-described production method of the present application, it is possible to produce alkanol economically and stably by a simple process compared to the conventional method using a high-pressure hydrogen gas. In one example, in the production method of the present application, by using a specific catalyst, the hydrogen production reaction and the production process of alkanol can be performed simultaneously. For example, in the above production method, secondary alcohols such as isopropyl alcohol and cyclohexanol are decomposed into acetone and hydrogen, cyclohexanone and hydrogen, respectively, under a Raney nickel catalyst to generate hydrogen, and the generated hydrogen is n. Since n-butanol can be prepared by reducing the aldehyde group of -butylaldehyde, problems such as process risks caused by using a high-pressure hydrogen gas can be improved, and n-butanol can be economically produced.

The preparation method of alkanol of the present application includes a reaction step of reacting a compound of Formula 1 and a compound of Formula 2 below.

[Formula 1]

[Formula 2]

In Formula 1, R ₁ represents a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms, or represents alkenyl having 1 to 12 carbon atoms. For example, R ₁ represents an alkyl group having 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms, or 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, or carbon atoms. Alkenyl of 1 to 4, and in one example, R ₁ may be a methyl group, an ethyl group, a propyl group, a butyl group, or a vinyl group, but is not limited thereto.

In Formula 2, R ₂ , R _3, and R ₄ are each independently hydrogen, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 24 carbon atoms, and at least one of R ₂ , R _3, and R ₄ is hydrogen. to be. For example, when R ₂ is hydrogen, R ₃ and R ₄ are each independently hydrogen, 1 to 12 carbon atoms, for example, 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, 1 carbon atoms It may be an alkyl group of 4 to 4 or an aryl group having 6 to 24 carbon atoms, for example, 6 to 18 carbon atoms, 6 to 12 carbon atoms, when R ₃ is hydrogen, R ₂ and R ₄ is hydrogen, 1 to 12, for example, an alkyl group having 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms, or an aryl having 6 to 24 carbon atoms, for example, 6 to 18 carbon atoms or 6 to 12 carbon atoms. It may be a flag. In addition, when R ₄ is hydrogen, R ₂ and R ₃ is hydrogen, an alkyl group having 1 to 12 carbon atoms, for example, 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, 1 to 4 carbon atoms or It may be an aryl group having 6 to 24 carbon atoms, for example, 6 to 18 carbon atoms and 6 to 12 carbon atoms. The alkyl group may be a linear, branched or cyclic alkyl group, and is not particularly limited.

In one example, R ₂ and R ₃ each independently represent hydrogen, an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 24 carbon atoms, in which case at least one of R ₂ and R ₃ is hydrogen, R ₄ may be an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 24 carbon atoms. For example, when R ₂ is hydrogen, R ₃ is hydrogen, an alkyl group having 1 to 12 carbon atoms, for example, 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms, or It may be an aryl group having 6 to 24 carbon atoms, for example, 6 to 18 carbon atoms, 6 to 12 carbon atoms, and when R ₃ is hydrogen, R ₂ is hydrogen, 1 to 12 carbon atoms, for example, 1 to 12 carbon atoms It may be an alkyl group having 10, 1 to 8 carbon atoms, 1 to 6 carbon atoms, 1 to 4 carbon atoms or an aryl group having 6 to 24 carbon atoms, for example, 6 to 18 carbon atoms, 6 to 12 carbon atoms. The alkyl group having 1 to 12 carbon atoms may be, for example, a methyl group, an ethyl group, a propyl group, or a butyl group, and the aryl group having 6 to 24 carbon atoms may be, for example, a phenyl group, tolyl group, xylyl group, or naphthyl group. However, the present invention is not limited thereto. Accordingly, the compound of Formula 2 may be methanol, primary alcohol or secondary alcohol, for example, primary alcohol or secondary alcohol, preferably secondary alcohol. When R ₂ to R ₄ are all alkyl groups, the compound of Formula 2 is a tertiary alcohol, and the tertiary alcohol may not generate hydrogen in the presence of a metal catalyst. The reaction step can be carried out in the presence of a metal catalyst. The metal catalyst is used in the preparation method of the present application in order to increase the reaction rate and reaction efficiency of the dehydrogenation reaction to decompose the compound of Formula 2 to generate hydrogen and the reduction reaction of aldehyde using the produced hydrogen.

In one example, the metal catalyst may be at least one selected from the group consisting of copper, cobalt, molybdenum, nickel, nickel-aluminum alloy, nickel-molybdenum alloy, Raney cobalt, Raney nickel, and zinc-chromium alloy, Preferably Raney nickel.

The Raney nickel catalyst is particularly excellent in substrate specificity or catalytic specificity for secondary alcohols. Said "substrate specificity" or "catalyst specificity" means the effect of the catalytic activity with respect to a specific compound. For example, when a secondary alcohol is used as the compound of Formula 2 and Raney nickel is used as the metal catalyst in the method for preparing alkanol, dehydrogenation of the compound of Formula 2 and reduction of the compound of Formula 1 The effect of promoting the reaction can be maximized and alkanol can be prepared at high conversion.

The compound of Formula 1 is not particularly limited as long as it satisfies Formula 1. For example, in Formula 1, R ₁ may be an alkyl group having 2 to 6 carbon atoms or an alkenyl having 4 to 10 carbon atoms. The compound of Formula 1 may be, for example, n-butylaldehyde or 2-ethyl-2-hexenal.

The compound of Formula 2 is not particularly limited as long as it satisfies Formula 2, and may be, for example, a primary alcohol or a secondary alcohol, preferably a secondary alcohol. When tertiary alcohol is used, as described above, the tertiary alcohol cannot produce hydrogen for reducing the compound of formula 1 to alkanol in the presence of a metal catalyst in molecular structure. In addition, in the case of the primary alcohol, although hydrogen may be generated in the presence of a catalyst, when the primary alcohol generates hydrogen, it is converted into an aldehyde compound such as Chemical Formula 1, and the aldehyde compound receives hydrogen again. Since it is reduced to a primary alcohol, it can be difficult to provide hydrogen to the compound of formula (1). However, in the case of secondary alcohols, hydrogen is produced and converted into ketone compounds in the presence of a metal catalyst, in particular a Raney nickel catalyst, and the ketone compound is not reduced by hydrogen, in the presence of a Raney nickel catalyst, thereby Sufficient hydrogen may be provided for this reduction. Therefore, alkanol can be prepared with high efficiency when using a secondary alcohol as the compound of Formula 2.

In one example, the secondary alcohol may be a compound of formula (3).

[Formula 3]

In Formula 3, R ₅ and R ₆ each independently represent an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 24 carbon atoms, or R ₅ and R ₆ together form a cycloalkyl group having 3 to 16 carbon atoms can do. In one example, each of R ₅ and R ₆ independently represents an alkyl group having 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms or 1 to 4 carbon atoms, or 6 to 24 carbon atoms or 6 to 18 carbon atoms. Or an aryl group having 6 to 12 carbon atoms, and for example, may be a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a tolyl group, a xylyl group, or a naphthyl group, but is not limited thereto. In addition, R ₅ and R ₆ may together form a cycloalkyl group having 3 to 16 carbon atoms, for example, a cycloalkyl group having 4 to 12 carbon atoms or 5 to 8 carbon atoms, and may form a cyclohexyl group, for example. have.

In one example, the compound of Formula 3 is isopropyl alcohol, 2-butanol, 2-pentanol, 2-hexanol, 2-heptanol, glycerol, 3-methyl-2-butanol, α-phenylethanol, di 1 selected from the group consisting of phenylmethanol, 3-pentanol, 3,3-dimethyl-2-butanol, 4-phenyl-2-butanol, 1,2,3,4-tetrahydro-1-naphthol and cyclohexanol It may include more than one compound, preferably may include isopropyl alcohol, and / or cyclohexanol.

In one embodiment of the production method of the present application, the reaction step may include a dehydrogenation step in which the compound of Formula 2 is dehydrogenated in the presence of a metal catalyst, in particular, Raney nickel catalyst, the dehydrogenation step, The compound of Formula 2 may include being decomposed into a ketone compound and hydrogen in the presence of a Raney nickel catalyst.

As used herein, the term "dehydrogenation" refers to a reaction in which a compound containing hydrogen is decomposed to generate hydrogen. For example, in the dehydrogenation step, a secondary alcohol, a compound of Formula 2, is ketone in the presence of a metal catalyst. It may mean decomposed into a compound and hydrogen.

In one example, the ketone compound formed in the dehydrogenation step is acetone, cyclohexanone, butanone, 2-pentanone, 2-hexanone, 2-heptanone, dihydroxyacetone, methyl isopropyl ketone, It may include one or more compounds selected from the group consisting of acetophenone, benzophenone, 3-pentanone, 3,3-dimethyl-2-butanone, 4-phenyl-2-butanone and tetralone, When the compound of 2 is isopropyl alcohol and / or cyclohexanol, the ketone compound may be acetone and / or cyclohexanone.

The preparation method of the present application may further include a reduction step in which hydrogen decomposed from the compound of Formula 2 reduces the compound of Formula 1. In the reducing step, hydrogen decomposed from the compound of Formula 2 in the dehydrogenation step of the reaction step to reduce the compound of Formula 1 by reducing the compound of Formula 1, according to the formula 1 The alkanol may be produced by reducing the compound of. The reduction step may be performed after the above-described reaction step or at the same time as the reaction step, and may also be performed after the dehydrogenation step or simultaneously with the dehydrogenation step. As described above, both the dehydrogenation step and the reduction step may be carried out under a metal catalyst, in particular a Raney nickel catalyst, in which case the metal catalyst decomposes the compound of formula 2 into a ketone compound and hydrogen in the dehydrogenation step. By promoting the production of hydrogen, the hydrogen decomposed from the compound of Formula 2 may promote the reaction to reduce the compound of Formula 1. In addition, by using the metal catalyst can be carried out at the same time the production reaction of hydrogen and the production process of alkanol, it is possible to improve the economics and stability of the process.

The metal catalyst may be present in an amount of 50 to 500 parts by weight, for example 100 to 450 parts by weight, 200 to 400 parts by weight or 250 to 350 parts by weight, based on 100 parts by weight of the compound of Formula 1. When the metal catalyst is present in the content in the above range, it is possible to produce alkanol with excellent efficiency. For example, when the metal catalyst is present in less than 50 parts by weight based on 100 parts by weight of the compound of Formula 1, the degree of catalyst activity may be low to slow the reaction, or the conversion or selectivity may be low. On the other hand, when the metal catalyst is present in excess of 500 parts by weight based on 100 parts by weight of the compound of Formula 1, the catalyst content is increased, making the purification process difficult after the reaction and not having a high catalytic activity efficiency compared to the catalyst content. This can be.

In one example, the secondary alcohol used in the preparation method is 100 to 2000 parts by weight, for example 300 to 1800 parts by weight, 500 to 1600 parts by weight, 700 to 1400 parts by weight based on 100 parts by weight of the compound of Formula 1 900 to 1200 parts by weight or 1000 to 1100 parts by weight can be reacted. When the reaction amount of the secondary alcohol is less than 100 parts by weight, the yield of n-butanol produced may be reduced because hydrogen cannot be provided sufficiently, and when it exceeds 2000 parts by weight, the cost increases due to the excessive amount of use, Difficult problems can arise.

In another embodiment of the present application, the method for preparing alkanol may be performed in a state in which the compound of Formula 1 and the compound of Formula 2 are dissolved in an organic solvent. By further comprising an organic solvent in the compound of Formula 1 and the compound of Formula 2 as described above, it is possible to more easily mix the compound of Formula 1 and the compound of Formula 2 as a reactant, and maintain the concentration of the compound of Formula 2 optimally The reaction efficiency can be further improved.

In one example, the organic solvent may be an alcohol compound, an aromatic compound, a hydrocarbon compound, a heterocyclic compound, an ether compound. For example, the alcohol compound may be exemplified by a primary alcohol having 1 to 12 carbon atoms, and the aromatic compound may be benzene, toluene or xylene, and the heterocyclic compound may be tetrahydro. Furan, 1,4-dioxane, and the like can be exemplified, and the ether compound can be exemplified by diethyl ether, methyl-t-butyl ether, and the like.

In the preparation method of the alkanol of the present application, the reaction step of reacting the compound of Formula 1 and the compound of Formula 2 is 50 to 150 ℃, for example 60 to 120 ℃, 65 to 100 ℃, 70 to 90 ℃ or 75 to It may be carried out at a temperature of 85 ℃. Accordingly, by adjusting the process temperature in the above range it is possible to obtain a high reaction efficiency in the reaction step of the compound of Formula 1 and the compound of Formula 2. For example, when the reaction step is performed at less than 50 ° C., the compound of Formula 1 and the compound of Formula 2 may not sufficiently react, thereby greatly reducing the effect of the reaction or reducing the amount of alkanol produced. In addition, when the reaction temperature exceeds 100 ℃, there is a disadvantage that the unnecessary side reaction occurs excessively, the conversion or selectivity to alkanol is greatly reduced.

In the production method of the present application, in the presence of a metal catalyst, in particular, a Raney nickel catalyst, an aldehyde compound such as n-butylaldehyde by hydrogen dehydrogenated and decomposed to secondary alcohol, in particular isopropyl alcohol and / or cyclohexanol Since it can be reduced to alkanols, such as n-butanol, since the high-pressure hydrogen gas is not separately included as a reaction material as in the conventional method, the risk of the reaction process is low, and the production process equipment can be simplified. Moreover, according to the manufacturing method of this invention, since the economics of a process can be improved, mass production of n-butanol can be made possible.

The present application also relates to an apparatus for producing alkanol for use in the above production method.

Alkanol production apparatus of the present application may include a reactor and a reactant supply device. In one example, the reactor is filled with a metal catalyst, the reactant supply device may be a device for supplying a compound of Formula 1 and a compound of Formula 2 to the reactor.

[Formula 1]

[Formula 2]

In Formulas 1 and 2, R ₁ represents a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms, or represents alkenyl having 1 to 12 carbon atoms, and R ₂ , R ₃ and R ₄ are each independently , Hydrogen, a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 24 carbon atoms, at least one of R ₂ , R ₃ and R ₄ is hydrogen. Detailed description of the formula (1) and formula (2) is the same as described in the manufacturing method will be omitted.

In one example, the reactor is a device for reacting the compound of Formula 1 and the compound of Formula 2, the compound of Formula 1 and the compound of Formula 2 may be introduced into the reactor. In addition, the inside of the reactor is filled with a metal catalyst, the compound of Formula 1 and the compound of Formula 2 may be maintained under appropriate conditions for causing a reaction. The type of the reactor included in the production apparatus is not particularly limited as long as it is commonly used in compound synthesis, etc., and may be used by determining the size, form and type of the reactor in consideration of the reaction conditions, the amount of reactants and the product. For example, a three-necked flask equipped with a condenser and a stirrer may be used.

In one embodiment of the alkanol production apparatus of the present application, the compound of Formula 1 and the compound of Formula 2 are supplied to the reactor through the reactant supply device, the reactor may be filled with a metal catalyst.

In this case, the compound of Formula 1 and the compound of Formula 2 may react in the presence of the metal catalyst, the compound of Formula 2 may be dehydrogenated and decomposed into ketone compounds and hydrogen. In addition, alkanol may be prepared by reducing hydrogen decomposed from the compound of Formula 2 with the compound of Formula 1. In one example, the metal catalyst charged in the reactor may be Raney nickel, in this case, a high conversion rate due to the dehydrogenation and reduction reaction in the reaction step of the compound of Formula 1 and the compound of Formula 2 Alkanols can be prepared. Detailed description thereof is the same as described in the above-described method for preparing alkanol, and thus will be omitted.

In one example, the compound of Formula 1 is not particularly limited as long as it satisfies Formula 1. For example, in Formula 1, R ₁ may be an alkyl group having 2 to 6 carbon atoms or an alkenyl number of 4 to 10 carbon atoms. And preferably n-butylaldehyde or 2-ethyl-2-hexenal.

In addition, the compound of Formula 2 is not particularly limited as long as it satisfies Formula 2, and may be, for example, a secondary alcohol. In one example, the secondary alcohol may be a compound of formula (3).

[Formula 3]

In Formula 3, R ₅ and R ₆ each independently represent an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 24 carbon atoms, or R ₅ and R ₆ together form a cycloalkyl group having 3 to 16 carbon atoms can do. Detailed description of the formula (3) is the same as described in the manufacturing method will be omitted.

In one example, the compound of Formula 3 is isopropyl alcohol, 2-butanol, 2-pentanol, 2-hexanol, 2-heptanol, glycerol, 3-methyl-2-butanol, α-phenylethanol, di 1 selected from the group consisting of phenylmethanol, 3-pentanol, 3,3-dimethyl-2-butanol, 4-phenyl-2-butanol, 1,2,3,4-tetrahydro-1-naphthol and cyclohexanol It may comprise more than one compound, preferably may include isopropyl alcohol and / or cyclohexanol.

According to the production method and apparatus of the present application, high-purity n-butanol can be produced at high conversion rate, and since high-pressure hydrogen gas is not used as a reaction material, economical efficiency and stability of the process can be improved.

According to the manufacturing method and the manufacturing apparatus according to the present application, it is possible to improve the economics and stability of the manufacturing process, it is possible to mass-produce alkanol.

Hereinafter, the present invention will be described in more detail with reference to examples according to the present invention and comparative examples not according to the present invention, but the scope of the present invention is not limited to the following examples.

Example 1

2.0 g of n-butylaldehyde, 39.3 g of isopropyl alcohol, and 6.0 g of Raney nickel were placed in a 100 mL three-necked flask equipped with a condenser and a stirrer, and the flask internal temperature was raised to 80 ° C. and reacted for 3 hours. The resulting mixture was analyzed by GC, and the conversion was 100%. It was confirmed that the mixture was composed of 3% acetone, 74% isopropyl alcohol, and 23% n-butanol (GC% area).

Example 2

Into a 100 mL three-necked flask equipped with a condenser and a stirrer, 2.0 g of n-butylaldehyde, 48.1 g of cyclohexanol, and 6.0 g of Raney nickel were added, and the flask internal temperature was raised to 86 ° C. and reacted for 3 hours. As a result of analyzing the mixture of the product produced after the reaction and the reaction remaining in the flask by GC, the conversion was 100%, n-butanol 2%, cyclohexanol 97% and cyclohexanone 1% (GC% area) It was confirmed that the configuration.

Example 3

In a 100 mL three-necked flask equipped with a condenser and agitator, 2.0 g of n-butylaldehyde, 39.3 g of isopropyl alcohol, 24.1 g of cyclohexanol, and 6.0 g of Raney nickel were added, and the temperature of the flask was raised to 75 ° C. for 3.5 hours. Reacted. As a result of analyzing the mixture of the product produced after the reaction and the reactant remaining in the flask by GC, the conversion was 100%, acetone 2%, isopropyl alcohol 56%, n-butanol 2%, cyclohexanol 39% and It was confirmed that the composition consists of 1% of cyclohexanone (GC% area).

Example 4

In a 100 mL three-necked flask equipped with a condenser and a stirrer, 2.0 g of n-butylaldehyde, 21.8 g of toluene, 19.7 g of isopropyl alcohol, and 6.0 g of Raney nickel were added, and the temperature of the flask was raised to 74 ° C. and reacted for 3.5 hours. . As a result of analyzing the mixture of the product produced after the reaction and the reactant remaining in the flask by GC, the conversion was 100%, and acetone 1%, isopropyl alcohol 27%, n-butanol 3% and toluene 69% (GC% area).

Example 5

2.0 g of n-butylaldehyde, toluene 43.5 g, cyclohexanol 24.1 g, Raney nickel 6.0 g were added to a 100 mL three-neck flask equipped with a condenser and a stirrer, and the flask internal temperature was raised to 100 ° C. and reacted for 3 hours. . After the reaction, the resultant mixture and the mixture of reactants remaining in the flask were analyzed by GC. As a result, the conversion was 100%, n-butanol 1%, toluene 76%, cyclohexanol 22%, and cyclohexanone 1% ( GC% area).

Example 6

Into a 100 mL three-necked flask equipped with a condenser and agitator, 2.0 g of n-butylaldehyde, 26.1 g of toluene, 7.9 g of isopropyl alcohol, 9.6 g of cyclohexanol, and 6.0 g of Raney nickel were added, and the temperature of the flask was raised to 79 ° C. The reaction was carried out for 4 hours. After the reaction, the resultant mixture and the mixture of reactants remaining in the flask were analyzed by GC, and the conversion was 100%. Acetone and isopropyl alcohol 6%, n-butanol 3%, toluene 67%, cyclohexanol 23 It was confirmed that the composition consists of% and cyclohexanone 1% (GC% area).

Example 7

Into a 100 mL three-necked flask equipped with a condenser and a stirrer, 2.0 g of 2-ethyl-2-hexenal, 39.3 g of isopropyl alcohol, and 6.0 g of Raney nickel were added, and the temperature of the flask was raised to 80 ° C., followed by reaction for 2 hours. I was. After the reaction, the resultant mixture and the mixture of reactants remaining in the flask were analyzed by GC. The conversion was 100%. Acetone 2%, isopropyl alcohol 71%, 2-ethyl hexanol 27% (GC% area) Confirmed to consist of

Comparative Example 1

In a 100 mL three-necked flask equipped with a condenser and a stirrer, 2.0 g of n-butylaldehyde, 39.3 g of isopropyl alcohol, and 0.50 g of Pd / C (palladium on carbon) catalyst were added, and the temperature of the flask was raised to 76 ° C. for 4 hours. Reacted for a while. As a result of analyzing the mixture of the product produced after the reaction and the reactant remaining in the flask by GC, the production of n-butanol could not be observed.

Comparative Example 2

In a 100 mL three-necked flask equipped with a condenser and agitator, 2.0 g of n-butylaldehyde, 19.7 g of isopropyl alcohol, and 0.50 g of Ni / SiO ₂ -Al ₂ O ₃ catalyst were added, and the temperature of the flask was raised to 76 ° C., for 3.5 hours. Reacted for a while. As a result of analyzing the mixture of the product produced after the reaction and the reactant remaining in the flask by GC, the production of n-butanol could not be observed.

According to the method for preparing n-butanol according to an embodiment of the present application, n-butanol may be produced without using high pressure hydrogen gas as a reaction material at a reaction condition of about 70 to 100 ° C., in particular, Examples As shown in FIG. 1, when the temperature of the process and the content of the compound are properly adjusted, it can be seen that n-butanol can be prepared at a very high conversion rate.

On the other hand, when using a catalyst other than a Raney nickel catalyst like Comparative Examples 1 and 2, it can be confirmed that n-butanol is not produced.

Claims (21)

1. A method for preparing an alkanol, comprising: reacting a compound of Formula 1 with a compound of Formula 2 in the presence of a metal catalyst:

   [Formula 1]

   

   [Formula 2]

   

   In Formulas 1 and 2, R ₁ is an alkyl group having 1 to 12 carbon atoms or alkenyl having 1 to 12 carbon atoms, and R ₂ , R ₃ and R ₄ are each independently hydrogen, an alkyl group having 1 to 12 carbon atoms or 6 carbon atoms. To aryl group of 24, wherein at least one of R ₂ , R ₃ and R ₄ is hydrogen.
2. The preparation of alkanol according to claim 1, wherein the metal catalyst is at least one selected from the group consisting of copper, cobalt, molybdenum, nickel, nickel-aluminum alloy, nickel-molybdenum alloy, Raney cobalt, Raney nickel, and zinc-chromium alloy. Way.
3. The method of claim 2, wherein the metal catalyst is Raney nickel.
4. The method of claim 1, wherein in Formula 1, R ₁ is an alkyl group having 2 to 6 carbon atoms or alkenyl having 4 to 10 carbon atoms.
5. The method of claim 1, wherein the compound of formula 2 is a secondary alcohol.
6. The method of claim 5, wherein the secondary alcohol is a compound of Formula 3:

   [Formula 3]

   

   In Formula 3, R ₅ and R ₆ each independently represent an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 24 carbon atoms, or R ₅ and R ₆ together form a cycloalkyl group having 3 to 16 carbon atoms. .
7. A compound according to claim 6, wherein the compound of formula 3 is isopropyl alcohol, 2-butanol, 2-pentanol, 2-hexanol, 2-heptanol, glycerol, 3-methyl-2-butanol, α-phenylethanol, di 1 selected from the group consisting of phenylmethanol, 3-pentanol, 3,3-dimethyl-2-butanol, 4-phenyl-2-butanol, 1,2,3,4-tetrahydro-1-naphthol and cyclohexanol Method for producing an alkanol comprising at least a compound.
8. The method of claim 3, wherein the reaction step includes a dehydrogenation step in which the compound of Formula 2 is dehydrogenated in the presence of Raney nickel.
9. The method of claim 8, wherein the dehydrogenation step comprises the decomposition of the compound of Formula 2 to a ketone compound and hydrogen in the presence of Raney nickel.
10. 10. The ketone compound of claim 9, wherein the ketone compound is acetone, cyclohexanone, butanone, 2-pentanone, 2-hexanone, 2-heptanone, dihydroxyacetone, methylisopropylketone, acetophenone, benzophenone, 3 A process for producing an alkanol comprising at least one compound selected from the group consisting of -pentanone, 3,3-dimethyl-2-butanone, 4-phenyl-2-butanone and tetraron.
11. 10. The method of claim 9, wherein the hydrogen decomposed from the compound of Formula 2 further comprises a reducing step of reducing the compound of Formula 1.
12. The method of claim 1, wherein the metal catalyst is present in an amount of 50 to 500 parts by weight based on 100 parts by weight of the compound of Formula 1.
13. The method of claim 5, wherein 100 to 2000 parts by weight of the secondary alcohol is reacted with respect to 100 parts by weight of the compound of Formula 1.
14. The method of claim 1, wherein the reacting is performed in a state in which the compound of Formula 1 and the compound of Formula 2 are dissolved in an organic solvent.
15. The method of claim 1, wherein the step of reacting is carried out at a temperature of 50 to 150 ℃.
16. A reactor filled with a metal catalyst; An apparatus for producing an alkanol comprising a reactant supply device for supplying a compound of Formula 1 and a compound of Formula 2 to the reactor:

    [Formula 1]

    

    [Formula 2]

    

    In Formulas 1 and 2, R ₁ is an alkyl group having 1 to 12 carbon atoms or alkenyl having 1 to 12 carbon atoms, and R ₂ , R ₃ and R ₄ are each independently hydrogen, an alkyl group having 1 to 12 carbon atoms or 6 carbon atoms. To aryl group of 24, wherein at least one of R ₂ , R ₃ and R ₄ is hydrogen.
17. The apparatus of claim 16, wherein the metal catalyst is Raney nickel.
18. The apparatus of claim 16, wherein in Formula 1, R ₁ is an alkyl group having 2 to 6 carbon atoms or alkenyl having 4 to 10 carbon atoms.
19. The apparatus of claim 16, wherein the compound of Formula 2 is a secondary alcohol.
20. 20. The apparatus for preparing alkanol according to claim 19, wherein the secondary alcohol is a compound of Formula 3:

    [Formula 3]

    

    In Formula 3, R ₅ and R ₆ each independently represent an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 24 carbon atoms, or R ₅ and R ₆ together form a cycloalkyl group having 3 to 16 carbon atoms. .
21. A compound according to claim 20, wherein the compound of formula 3 is isopropyl alcohol, 2-butanol, 2-pentanol, 2-hexanol, 2-heptanol, glycerol, 3-methyl-2-butanol, α-phenylethanol, di 1 selected from the group consisting of phenylmethanol, 3-pentanol, 3,3-dimethyl-2-butanol, 4-phenyl-2-butanol, 1,2,3,4-tetrahydro-1-naphthol and cyclohexanol Apparatus for producing alkanol containing at least a compound.