JPH01250368A - Production of cyclohexanecarboguanamine - Google Patents

Abstract

PURPOSE:To obtain the subject compound useful as a raw material for resins for e.g., molding materials, etc., in colorless state at a low cost, by using cyanocyclohexane and dicyandiamide as starting raw materials and reacting the materials with each other at a specific ratio in an atmosphere essentially free from the influence of oxygen. CONSTITUTION:The objective compound of formula is produced by reacting cyanocyclohexane with dicyandiamide in an organic solvent having hydroxyl group in the molecule (e.g., ethylene glycol monomethyl ether or n-butanol) in the presence of a base (e.g., sodium hydroxide) at 90-200 deg.C, especially 110-180 deg.C in an atmosphere essentially free from the influence of oxygen, preferably at an oxygen concentration of <=5vol.%. The dicyandiamide is used in an amount of 0.60-0.95mol, preferably 0.65-0.90mol per 1mol of cyanocyclohexane and added to the reaction system at a rate of 0.05-0.35mol/h based on 1mol of cyanocyclohexane.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing cyclohexanecarboguanamine. More specifically, the present invention relates to a method for producing cyclohexanecarboguanamine represented by the following formula (I), which is useful as a starting material for resin raw materials such as molding materials, laminate materials, paint vehicles, resin modifiers, and pharmaceuticals.

[Conventional technology]

A method of synthesizing a guanamine compound by heating a cyanide compound and dicyandiamide is generally known [for example, Smolin and Labobot: The
Chemistry of l(eterocyclic
cCompounds (s-triazines and derivatives), 1959, p. 229, 1nte
rsscience Publishers Inc., Special Publication No. 1972-2353, Special Publication No. 1973-22190, etc.]
.

On the other hand, the method for synthesizing cyclohexanecarboguanamine is
According to the method disclosed in U.S. Pat. No. 3,379,661 and described in Example 1, cyanocyclohexane and dicyandiamide are added to a methyl cellosolve solvent, and the solvent is dissolved in the presence of a potassium hydroxide catalyst. Cyclohexanecarboguanamine is obtained by reacting at the boiling point. The method disclosed in the US patent is based on the general method for producing guanamine compounds described above.

However, according to our knowledge, cyclohexanecarboguanamine obtained using such a general guanamine production method is colored and can be used as a raw material for various resins, a resin modifier, or a starting material for pharmaceuticals. To be used, it must be purified into a white, high-quality product. A method for purifying guanamine compounds is described, for example, in Japanese Patent Publication Nos. 38-8328 and 3B-8329. According to these methods, guanamine compounds are purified by recrystallization or separation sublimation to obtain white guanamines. However, in this case, the number of steps increases, which is disadvantageous as an industrial method.

Furthermore, U.S. Pat. No. 3,379.661 does not describe the yield, and when we attempted to synthesize cyclohexanecarboguanamine according to the method described in the U.S. patent, we obtained only a low yield. (See Comparative Example 2 below).

In the present invention, as a method for producing cyclohexanecarboguanamine, a method of sequentially adding dicyandiamide to a solvent containing cyanocyclohexane is adopted, and in the same way, dicyandiamide is sequentially added to synthesize a guanamine compound from a cyanide compound. For example, Japanese Patent Publication No. 40-27814 and U.S. Pat.
, No. 904. Tokuko Sho 40-2781
According to the method disclosed in No. 4, a sulfoxide such as dimethyl sulfoxide is used as a solvent, and dicyandiamide is added to a solvent in which a cyanide compound is dissolved over a period of at least one hour. However, the method does not disclose the use of cyanocyclohexane as the cyanide, so we
An attempt was made to synthesize cyclohexanecarboguanamine using cyanocyclohexane as a cyanide compound based on the specific method described in Japanese Patent Publication No. 40-27814.
Only low yields were obtained. In other words,
It is presumed that the method of sequential addition using sulfoxide as a solvent in No. 0-27814 is not necessarily appropriate for this reaction.

According to the method described in U.S. Patent No. 2,606,904, a higher fatty acid nitrile having an alkyl or alkenyl group having 8 or more carbon atoms is reacted with dicyandiamide, and dicyandiamide is sequentially added to achieve a yield of 60 to 70%. Although the corresponding guanamines have been obtained, the yield is still insufficient and cannot be used as an industrial production method.

Furthermore, in the conventional method of synthesizing a guanamine compound from a cyanide compound and dicyandiamide, it is common to use dicyandiamide in an amount equal to or more than the molar amount of the cyanide compound.

Furthermore, regarding the method for synthesizing cyanocyclohexane, which is the starting material of the present invention, US Pat. No. 3,379,6
No. 61, Japanese Patent Publication No. 50-1034 and U.S. Patent No. 4,
No. 673,757. U.S. Patent No. 3,3
According to the method described in No. 79,661, 1,000 lb/1n2 (about 70.3 kg/c+*) of cyanocyclohexene in the presence of a palladium catalyst supported on carbon.
2) Cyanocyclohexane is obtained by hydrogenation under pressure. However, the conditions such as reaction temperature and amount of catalyst are not disclosed at all, and it is merely suggested that the reaction is possible, and there is no mention of the quality of the obtained cyanocyclohexane. However, this method has the disadvantage of high equipment costs due to the high reaction rate. According to the method described in Japanese Patent Publication No. 50-1034, cyanocyclohexane is obtained by catalytic hydrogenation of 4-cyanocyclohexene in the presence of a rhodium trichloride catalyst at a temperature of 100 to 110°C and a pressure of 80 to 100 atm. . This method also has the drawbacks of high pressure and high equipment costs, and also uses an expensive catalyst, making it disadvantageous as an industrial production method. Furthermore, according to the method described in US Pat. No. 4,673.757, cyanocyclohexene is catalytically hydrogenated at a temperature of 120° C. in the presence of a ruthenium-triphenylphosphine catalyst to obtain cyanocyclohexane. This method also uses an expensive catalyst and is disadvantageous as an industrial production method.

[Problems to be Solved by the Invention] Therefore, an object of the present invention is to provide a method for producing high purity cyclohexanecarboguanamine.

Another object of the present invention is to produce a high-yield and economically advantageous unpigmented white cyclohexanecarboguanamine of sufficient quality for use as a starting material for various resin raw materials, resin modifiers, and pharmaceutical products. The objective is to provide an industrial manufacturing method.

Still another object of the present invention is to provide an efficient and economically advantageous industrial method for producing high-quality cyanocyclohexane as a raw material for the synthesis of cyclohexanecarboguanamine.

[Means to solve the problem]

The above purpose is to produce cyclohexanecarboguanamine by reacting cyanocyclohexane and dicyandiamide in the presence of a base catalyst in an organic solvent having a hydroxyl group in the molecule at a temperature of 90 to 200°C. This is achieved by an improved method consisting of using dicyandiamide in a proportion of 0.60 to 0.95 mol based on the amount of dicyandiamide and carrying out the reaction in an atmosphere substantially free from the influence of oxygen.

These specifications are 0.0 for cyanocyclohexene.
0005-0.05% by weight of palladium metal catalyst at a temperature ranging from 0 to 100°C and from 2 to 20 kg/
It is also achieved by a process for producing cyanocyclohexane, which comprises catalytic hydrogenation of cyanocyclohexene under a hydrogen pressure of cm2.

In the present invention, the atmosphere substantially free from the influence of oxygen is preferably an atmosphere of at least one inert gas selected from the group consisting of nitrogen and argon. Methods include, for example, replacing the inside of the reaction system with an inert gas several times in advance, conducting the reaction while circulating an inert gas through the reaction system, or replacing the inside of the reaction system with an inert gas several times in advance. , and a method of reacting while circulating an inert gas. In the case of 0 unreacted, the higher the oxygen concentration in the atmosphere, the higher the coloring of the product cyclohexanecarboguanamine. % or less, preferably 2.5% by volume or less.

In the present invention, per mole of cyanocyclohexane, 0
．． 60-0.95 mol, preferably 0.65-0.90
Cyclohexanecarboguanamine is prepared using molar proportions of dicyandiamide. this is,
The aim is to suppress the by-product of melamine due to self-condensation of dicyandiamide, increase the yield, and at the same time obtain high-quality cyclohexanecarboguanamine with a low melamine content. This suppressing effect increases as the ratio of dicyandiamide to cyanocyclohexane decreases, but if it is less than 0.60 mol, productivity deteriorates.
On the other hand, if it exceeds 0.95 mol, the suppressing effect will be reduced.

Moreover, this inhibitory effect can be further enhanced by adopting sequential addition of dicyandiamide, generally in the range of 0.05 to 0.35 mol per hour per 1 mol of cyanocyclohexane. It is preferable to add dicyandiamide sequentially at a rate greater than this range; if added faster than this range, the effect of suppressing the by-product of melamine will be reduced, while if added slowly, the reaction time will become longer and productivity will decrease. Note that when dicyandiamide is added sequentially, there is no problem if dicyandiamide is added as it is, but if it is suspended and/or
Alternatively, it is easy to dissolve and add;
There is no problem even if the raw material cyanocyclohexane is mixed in.

In the present invention, since cyanocyclohexane is used in excess of dicyandiamide, unreacted cyanocyclohexane remains in the reaction solution after the reaction is completed. However, after the reaction is complete, this unreacted cyanocyclohexane can be easily recovered by means such as distillation, and can be recycled and reused in the next reaction. Although the distillation can be carried out under normal pressure, it is preferable to carry out the distillation under reduced pressure.

As described above, the present invention makes it possible to increase the yield of cyclohexanecarboguanamine based on dicyandiamide by suppressing the by-product of melamine due to self-condensation of dicyandiamide, and also makes it possible to effectively recover and recycle unreacted cyanocyclohexane. By using it, it is possible to increase the yield of cyclohexanecarboguanamine based on cyanocyclohexane.

In addition, in order to obtain high-quality cyclohexanecarboguanamine without coloring, we investigated the starting material cyanocyclohexane, and found that the amount of catalyst required to hydrogenate cyanocyclohexene to produce cyanocyclohexane. It has been found that reaction temperature and hydrogen pressure are important factors to obtain color-free cyclohexanecarboguanamine. That is, using palladium metal as a catalyst, using a catalyst amount of 0.0005 to 0.05ii%, preferably 0.001 to 0.045% by weight, based on the cyanocyclohexene charged as palladium metal, 100' (!, preferably 20-80℃
It is preferable to carry out the catalytic hydrogenation under conditions of a reaction temperature in the range of 2 to 20 kg/ClO2, preferably a hydrogen pressure of 2 to 15 kg/ClO2.
If the reaction temperature is too high or the hydrogen pressure is too high,
Or if it is too low, by-products that cause coloration of cyclohexanecarboguanamine are likely to be formed.
In order to remove these by-products, means such as distillation and purification are required.

On the other hand, if the amount of catalyst is too small or the reaction temperature is too low, the reaction will be slow and productivity will decrease, which is undesirable. You can also use it after doing so. Cyanocyclohexane obtained by catalytic hydrogenation of cyanocyclohexene under the above catalytic hydrogenation reaction conditions is converted into cyclohexanecarboguanamine as it is without going through a purification process such as distillation after removing the catalyst using a simple means such as filtration. It can be used as a raw material. Note that palladium metal used as a catalyst is generally palladium supported on carbon.

The organic solvent having a hydroxyl group in the molecule used when producing cyclohexanecarboguanamine by reacting cyanocyclohexane and dicyandiamide has the following formula (II) ROCH2CH20H(II) (wherein, R has 1 carbon number The ethylene glycol monoalkyl ether is preferably at least one selected from the group consisting of ethylene glycol monoalkyl ether and butanols represented by Examples include ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, and ethylene glycol monobutyl ether. Butanols include n-butanol, inbutanol, 5ec-butanol and t-butanol.

The reaction temperature is 90 to 200°C, especially 110 to 18°C.
0'C! A range of is preferred. That is, if the reaction temperature is too high, melamine is likely to be produced as a by-product due to self-condensation of dicyandiamide, whereas if the reaction temperature is too low, the reaction rate will be slow and productivity will be lowered, which is not preferable.

Furthermore, the base catalyst used in the reaction is not particularly limited, and examples thereof include alkali metal hydroxides such as potassium hydroxide, sodium hydroxide, and lithium hydroxide; potassium methylate, sodium ethylate, and sodium ethylate; Usually, the amount of the basic catalyst used is preferably about 0.5 to 20 mol % based on the cyanocyclohexane charged.

1. Cyanocyclohexene, which is the raw material for cyanocyclohexane used in the present invention, is not particularly limited, but 4-cyanocyclohexene obtained by the Diels-Alder reaction of butadiene and acrylonitrile is suitable in terms of raw material availability and production. However, it is easy and can be used industrially with advantage.

As described above, the method of the present invention makes it possible to produce highly pure white cyclohexanecarboguanamine with a low content of by-products such as melamine. A color-free and highly pure product can be obtained by simply performing a water washing process to remove melamine. The method according to the invention therefore comprises:
This is an industrially advantageous method for producing cyclohexanecarboguanamine.

〔Example〕

Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples in any way.

The analysis of each compound, the oxygen concentration in the gas in the reactor, and the evaluation of the degree of coloring of cyclohexanecarboguanamine were performed as follows.

(1) Cyanocyclohexane was determined by gas chromatography, and melamine, dicyandiamide, and cyclohexanecarboguanamine were determined by high performance liquid chromatography.

(2) Oxygen concentration in the reactor was measured using a gas chromatograph (
Detector: TCD).

(3) The degree of coloration of cyclohexanecarboguanamine was evaluated by its /\-zen color number using a methylolated resin as follows.

Cyclohexanecarboguanamine 10g, 37% by weight formalin aqueous solution 13g and 5% by weight sodium carbonate aqueous solution 0
．． 1 g was placed in a 2001 eggplant flask, attached to a rotary evaporator, and heated to 90° C. while rotating. When the cyclohexanecarboguanamine is dissolved and the reaction solution becomes homogeneous, the pressure is reduced to 50 mmHg and water and unreacted formaldehyde are distilled off. When the mixed solution of distilled water and unreacted formaldehyde reached approximately 8 g, the remaining methylolated resin was transferred to a test tube, and the color was compared with a Hazen color number standard solution in a molten state (50 to 70°C). Measure the number of colors.

Production Example 1 1200 g of 4-cyanocyclohexene and 1.20 g of palladium carbon supported with 5% by weight of palladium (5% by weight of palladium O, OO relative to 4-cyanocyclohexene) were placed in a two-piece stainless steel autoclave, and the inside of the autoclave was replaced with hydrogen. After that, 10 kg/cm2
Hydrogen was injected into the reactor and heated to 70° C. with stirring. During this time, when the pressure decreased, hydrogen was supplied to maintain the inside of the autoclave at 10 kg/cm2. Further 70°0, 1
After continuing the reaction at 0 kg/cm2 until hydrogen absorption disappeared, it was cooled to room temperature and the reaction solution was taken out. Palladium on carbon was filtered out using a membrane filter, and 1221 g of cyanocyclohexane (A) was extracted. Obtained.

Production Examples 2 to 7 The amount of palladium carbon used, hydrogen pressure and reaction temperature were
Cyanocyclohexane CB) to (G) were obtained by repeating the operation of Production Example 1 except as shown in the table.

Production Example 8 850 g of cyanocyclohexane (G) was distilled under reduced pressure to obtain a fraction of 700 with a boiling point of 110-112°C/90 mdg.
Cyanocyclohexane (H) was obtained as g.

Table 1 1) Weight percent of palladium metal relative to cyanocyclohexene Example 1 A thermometer, a stirrer, and a reflux condenser were attached to a two-piece four-bottle flask, and the remaining one was connected to a tube pump.
After purging the inside of the reactor with nitrogen, 300 g of ethylene glycol monomethyl ether cyanocyclohexane (A) 3
50 g (3.21 mol) and potassium hydroxide9. Og
(0.16 mol) was charged, and while stirring, the inside of the reactor was again purged with nitrogen several times. The oxygen concentration in the gas in the reactor is 2
．． After confirming that the concentration was 5% by volume or less, nitrogen was further passed through the reactor to maintain the oxygen concentration in the gas in the reactor at 2.5% by volume or less, and the mixture was heated to reflux conditions with stirring. When reflux starts, part of the condensate is distilled off, dicyandiamide is suspended in the distillate, and 243 g of dicyandiamide is added into the reactor using a tube pump.
89 mol: 0.9 based on the charged cyanocyclohexane
0 mole) was added over 4.5 hours at a constant rate (addition rate: 0.2 mole part per hour per mole part of cyanocyclohexane charged). After the addition was completed, the mixture was further stirred under reflux conditions for 1 hour, and then cooled to 100°C. After cooling, the reaction mixture was transferred to a Niguu with an internal volume of 2 IL and heated under reduced pressure (50 to 500 mmHg) to recover a mixture of 297 g of ethylene glycol monomethyl ether and 54 g of unreacted cyanocyclohexane. Water 6901 was added to the obtained slightly yellow solid, heated to 90°C, stirred, filtered, and dried. The obtained cyclohexanecarboguanamine was 519 g (2.69 mol) and had a purity of 99.9% by weight, and the yield and Hazen color number of the methylolated resin are shown in Table 2.

Example 2 Using the same reactor as in Example 1, the inside of the reactor was replaced with nitrogen, and then 83,350 g of cyanocyclohexane, 50 g of ethylene glycol monomethyl ether, and 9.0 g of potassium hydroxide were charged, and the inside of the reactor was replaced with stirring. The oxygen concentration in the gas in the 0 reactor, which was replaced with nitrogen several times, was 2.5% by volume.
After confirming that the following conditions were met, the reactor was heated to 130° C. with stirring while flowing nitrogen so as to maintain the oxygen concentration in the gas within the reactor at 2.5% by volume or less. After reaching 130°C, using a tube pump, a mixed slurry of 250 g of ethylene glycol methyl ether and 243 g of dicyandiamide (0.9 parts by mole per 1 part by mole of cyanocyclohexane charged) was added at a constant rate for 4.5 hours (the addition rate was 0.0% per hour per mole part of charged cyanocyclohexane.
2 mole parts). After the addition was completed, the mixture was further stirred at 130°C for 1 hour, and then cooled to 100°C. After cooling, the same operation as in Example 1 was carried out, and a mixture of 298 g of ethylene glycol monomethyl ether and 53 g of unreacted cyanocyclohexane was recovered, and the obtained cyclohexanecarboguanamine was 520 g (2.69 mol) with a purity of 9.
It was 9.9% by weight. The yield and Hazen color number of the methylolated resin are shown in Table 2.

Example 3 297 ethylene glycol monomethyl ether recovered in Example 1 instead of 300 g of ethylene glycol monomethyl ether and 350 g of cyanocyclohexane (A)
296 g of cyanocyclohexane (A) (a total of 297 g of ethylene glycol monomethyl ether and 350 g of cyanocyclohexane were charged) was used.
The same operation as in Example 1 was performed. The yield of the obtained cyclohexanecarboguanamine and the Hazen color number of the methylolated resin are shown in Table 2.

Example 4 Cyanocyclohexane (A) to cyanocyclohexane C
D), and 243 g of dicyandiamide was added to 216 g (2,
57 mol: 0.80 mol part per 1 mol part of charged cyanocyclohexane), and furthermore, dicyandiamide was added once every 4.0 hours (the addition rate was 0.80 mol part per 1 mol part of charged cyanocyclohexane). 0.2 mole part)
The same operation as in Example 1 was performed except for the following. The yield of the obtained cyclohexanecarboguanamine and the Hazen color number of the methylolated resin are shown in Table 2.

Example 5 216 g of cyanocyclohexane (A) to cyanocyclohexane
(2,577 mol: 0.80 mol part per 1 mol part of charged cyanocyclohexane), and then added dicyandiamide at a constant rate for 2.67 hours (the addition rate is 0.80 mol part per 1 mol part of charged cyanocyclohexane). 0.3 per hour
The same operation as in Example 1 was performed except that the molar parts were changed to The yield of the obtained cyclohexanecarboguanamine and the Hazen color number of the methylolated resin are shown in Table 2.

Example 6 Cyanocyclohexane (A) was converted into cyanocyclohexane (
H), and 243 g of dicyandiamide was added to 251 g (2,
99 mol: 0.93 mol part per 1 mol part of charged cyanocyclohexane), and then added dicyandiamide at a constant rate over 4.65 hours (the addition rate was 0.2 mol per hour per 1 mol part of charged cyanocyclohexane). The same operation as in Example 1 was performed except that the procedure was as follows. Table 2 shows the yield of the obtained cyclocarboguanamine and the Hazen color number of the methylolated resin.

Example 7 The same procedure as in Example 2 was performed except that argon was used instead of nitrogen. The yield of the obtained cyclohexanecarboguanamine and the Hazen color number of the methylolated resin are shown in Table 2.

Examples 8-10 Ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether and n-butanol were used instead of ethylene glycol monomethyl ether, and cyanocyclohexane CD), (E) was used instead of cyanocyclohexane (A), respectively. The same operation as in Example 2 was performed except that (H) and (H) were used. The yield of the obtained cyclohexanecarboguanamine and the Hazen color number of the methylolated resin are shown in Table 2.

Example 11 The same procedure was followed, except that nitrogen substitution during the reaction between cyanocyclohexane and dicyandiamide was performed so that the oxygen concentration in the gas in the reactor was 7.0% by volume, and nitrogen was not circulated during the reaction. The same operation as in Example 1 was performed. The yield of the obtained cyclohexanecarboguanamine and the Hazen color number of the methylolated resin are shown in Table 2.

Examples 12 to 14 The same operation as in Example 1 was performed except that cyanocyclohexane (C), (F), and (G) were used instead of cyanocyclohexane (A). The yield of the obtained cyclohexanecarboguanamine and the Hazen color number of the methylolated resin are shown in Table 2.

Comparative Example 1 The same operation as in Example 1 was performed, except that the reaction between cyanocyclohexane and dicyandiamide was carried out in an air atmosphere, and cyanocyclohexane (H) was used instead of cyanocyclohexane (A). The yield of the obtained cyclohexanecarboguanamine and the Hazen color number of the methylolated resin are shown in Table 2.

Comparative Example 2 300 g of methyl ether and 350 g of cyanocyclohexane (B) equipped with a thermometer, stirrer and reflux condenser
(3,21 mol) and dicyandiamide 270 g (3
, 21 mol: 1 mol part per 1 mol part of charged cyanocyclohexane) and 9.0 g (0.16 mol) of potassium hydroxide were charged, and the system was purged with nitrogen several times to eliminate oxygen in the gas in the reactor. After reducing the concentration to 2.5% by volume or less, under nitrogen flow and stirring for 152 hours.

It was heated to reflux conditions (145°C). Then 5 more
After stirring under reflux conditions for an hour, the mixture was cooled to lOO'0. The reaction solution was transferred to a Nigure with an internal volume of 2 cm and heated under reduced pressure to recover a mixture of 297 g of ethylene methyl ether and 235 g of unreacted cyanocyclohexane.

370 ml of water was added to the pale yellow solid thus obtained, heated to 90° C. with stirring, filtered, and dried. The resulting solid contained 182 g of cyclohexanecarboguanamine and 42 g of melamine.

The yield of cyclohexanecarboguanamine and the Hazen color number of the methylolated resin are shown in Table 2.

Claims (12)

[Claims] (1) Cyanocyclohexane and dicyandiamide are reacted at a temperature of 90 to 200°C in the presence of a basic catalyst in an organic solvent having a hydroxyl group in the molecule to produce the following formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the method for producing cyclohexanecarboguanamine shown in (I), 0 per mole of cyanocyclohexane
．． A method for producing cyclohexanecarboguanamine, which comprises using dicyandiamide in a proportion of 60 to 0.95 moles and carrying out the reaction in an atmosphere substantially free from the influence of oxygen. (2) The method according to claim (1), wherein the atmosphere substantially free from the influence of oxygen is at least one inert gas selected from the group consisting of nitrogen and argon. (3) The method according to claim (2), wherein the atmosphere substantially free from the influence of oxygen has an oxygen concentration of 5% by volume or less. (4) In a solvent containing cyanocyclohexane, 0.05 to 1 hour per mole of cyanocyclohexane
A process according to claim 1, which comprises adding dicyandiamide sequentially in a proportion of 0.35 mol. (5) 0.65 to 1 mole of cyanocyclohexane
4. A process as claimed in claim 4, characterized in that dicyandiamide is used in a proportion of 0.90 mol. (6) The method according to claim 4, wherein dicyandiamide is suspended and/or dissolved in an organic solvent and then added sequentially to the organic solvent solution of cyanocyclohexane as a mixture. (7) The organic solvent is a group consisting of ethylene glycol monoalkyl ether and butanols represented by the following formula (II) ROCH_2CH_2OH(II) (wherein R is an alkyl group having 1 to 4 carbon atoms) The method according to claim (1), wherein the method is at least one selected from the following. (8) Claim (7) wherein the reaction temperature is 110 to 180°C.
The method described in. (9) The method according to claim (7), wherein the base catalyst is an alkali metal hydroxide or an alkali metal alcoholate. (10) Cyanocyclohexane is prepared in the presence of a palladium metal catalyst in a range of 0.0005 to 0.05% by weight based on cyanocyclohexene at a temperature in a range of 0 to 100°C and a hydrogen pressure of 2 to 20 kg/cm^2. Claim (1) which is obtained by catalytic hydrogenation of cyanocyclohexene (
The method described in 1). (11) 0.0005 to cyanocyclohexene
in the presence of a palladium metal catalyst in the range of 0.05% by weight at a temperature in the range of 0 to 100 °C and 2 to 20 kg/cm^
2. A method for producing cyanocyclohexane comprising catalytic hydrogenation of cyanocyclohexene under hydrogen pressure. (12) The method according to item (11), wherein the reaction temperature is 20 to 80°C and the hydrogen pressure is 2 to 15 kg/cm^2.