JPH07196566A - Production of 2-chlorocyclohexanol - Google Patents

Abstract

PURPOSE:To produce 2-chlorocyclohexanol from cyclohexene in high yield by an industrially advantageous process. CONSTITUTION:2-Chlorocyclohexanol is produced by acting an aqueous solution of sodium hypochlorite and >=1.1 equivalent (based on sodium hypochlorite) of sulfuric acid on >=1 times mol (based on sodium hypochlorite) of cyclohexene.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a method for producing 2-chlorocyclohexanol which is useful as an intermediate for medicines, agricultural chemicals and fine chemicals.

[0002]

2. Description of the Related Art Various methods are known as methods for producing 2-chlorocyclohexanol from cyclohexene, but hydrogen peroxide and hydrochloric acid (US Pat. No. 3,733,313
No.), and a method using a hypochlorite and an acid (US Pat. No. 2,119,485).

[0003]

However, the method of reacting cyclohexene with hydrogen peroxide and hydrochloric acid has the problems that hydrogen peroxide is expensive and the reaction yield is not high. In addition, the method using cyclohexene hypochlorite and an acid, for example, an aqueous solution of sodium hypochlorite and sulfuric acid produces various by-products, and the desired yield of 2-chlorocyclohexanol is not sufficient.

Therefore, it is an object of the present invention to provide a means for industrially advantageous production of 2-chlorocyclohexanol from cyclohexene in high yield.

[0005]

The inventors of the present invention have conducted extensive studies to solve the above-mentioned drawbacks, and as a result, by reacting cyclohexene with hypochlorite and an acid under specific reaction conditions, the yield The inventors have found that 2-chlorocyclohexanol can be produced well and have reached the present invention.

That is, according to the present invention, cyclohexene is reacted with an aqueous solution of sodium hypochlorite and an acid to give 2-
In the method for producing chlorocyclohexanol, the production of 2-chlorocyclohexanol is characterized by using more than 1 mole of cyclohexene and 1.1 equivalents or more of sulfuric acid with respect to 1 mole of sodium hypochlorite. Provide the law. Furthermore, the present invention further provides that cyclohexene, an aqueous solution of sodium hypochlorite and sulfuric acid are continuously supplied to the reaction tank under the conditions, and a reaction liquid containing 2-chlorocyclohexanol is continuously taken out from the reaction tank. A continuous process for the production of the characterized 2-chlorocyclohexanol is provided.

The present invention will be described in detail below.

The cyclohexene used in the present invention may be one produced by various methods. Examples thereof include dehydrated cyclohexanol, dehydrochlorinated chlorocyclohexane, and partially hydrogenated benzene. In addition, there may be no problem even if the cyclohexene containing raw materials or by-products derived from production is used. That is, cyclohexanol, chlorocyclohexane, benzene, cyclohexane, methylcyclopentane, methylcyclopentene and the like can be used as they are, even if they exist in several to several equivalents, and in some cases several times as much as cyclohexene.

The sodium hypochlorite used in the present invention is
Usually, an aqueous solution is used. Generally, an aqueous solution of sodium hypochlorite is produced by reacting an aqueous solution of caustic soda with chlorine. In the present invention,
Prior to the reaction with cyclohexene, a product produced by reacting an aqueous solution of caustic soda with chlorine may be used,
A commercially available sodium hypochlorite aqueous solution may be used as it is. In addition, a small amount of caustic soda is contained as a stabilizer in commercially available sodium hypochlorite aqueous solution. Those containing such a stabilizer may be used as they are, or after performing a treatment for removing the stabilizer as necessary.
The concentration of the sodium hypochlorite aqueous solution is usually 2% by weight to 40% by weight, preferably 5% by weight to 30% by weight. If the concentration is too low, the concentration of 2-chlorocyclohexanol produced will be low and the production efficiency will be reduced. If the concentration is too high, by-products increase and the yield of 2-chlorocyclohexanol decreases, which is not preferable.

The concentration of sulfuric acid as an aqueous solution is usually 3% by weight to 70% by weight, preferably 5% by weight to 60% by weight.
It is better to use the one. If the concentration of sulfuric acid is too low, the concentration of 2-chlorocyclohexanol produced will be low and the production efficiency will be reduced. If the concentration is too high, by-products increase and the yield of 2-chlorocyclohexanol decreases.

In the present invention, it is important to keep the ratio of cyclohexene, sodium hypochlorite and sulfuric acid in a specific range. That is, with respect to 1 mol of sodium hypochlorite, a mol number exceeding 1 of cyclohexene is used,
Preferably 1.05 mol to 2 mol, 1.1 equivalent or more of sulfuric acid (0.55 mol or more in terms of number of moles), preferably 1.
15 equivalents to 1.5 equivalents (0.575 moles to 0.75 moles in moles) are used.

It is important to use a molar amount of cyclohexene that exceeds the molar number of sodium hypochlorite, and when it is 1 or less, the yield of 2-chlorocyclohexanol sharply decreases. Although the use of cyclohexene in a large excess does not adversely affect the reaction results, it will increase the labor of recovery and recycling and reduce the production efficiency.

It is important to use sulfuric acid in an amount of 1.1 equivalents or more of sodium hypochlorite, and if it is less than 1.1 equivalents, the yield of 2-chlorocyclohexanol sharply decreases. Further, when a large excess of sulfuric acid is used, the yield and the production efficiency decrease, which is not preferable.

The present invention can be implemented in various ways. For example, in batch reaction, cyclohexene, an aqueous solution of sodium hypochlorite, so as to satisfy the above-mentioned amount ratio in the reaction tank,
Sulfuric acid is sequentially added, a method for batch treatment after completion of the reaction, a method of adding a predetermined amount of cyclohexene to the reaction tank, and then sequentially adding a predetermined amount of aqueous sodium hypochlorite solution and sulfuric acid,
After adding a predetermined amount of cyclohexene and sodium hypochlorite aqueous solution to the reaction tank, adding only sulfuric acid, etc.
It can be appropriately selected. The reaction temperature is generally 0 ° C to 80 ° C, preferably 10 ° C to 60 ° C. If it is cooled too much, precipitation of an inorganic salt and solidification of water serving as a solvent will start, inhibiting the reaction. Further, when it is carried out at a temperature of 80 ° C. or higher, by-products increase and the yield of 2-chlorocyclohexanol decreases. Although the reaction time varies depending on the amount and temperature, it is usually 10 minutes to 100 hours, and after the necessary raw materials are sequentially added, the reaction may be further performed for 1 minute to 10 hours. The reaction is sufficiently fast even at a temperature of about 10 ° C., and it is not necessary to spend a particularly long time.

In the present invention, continuous reaction is one of the preferable modes. That is, cyclohexene, an aqueous solution of sodium hypochlorite, and sulfuric acid, which have the above quantitative ratios, are continuously supplied to the reaction tank, and the reaction liquid containing 2-chlorocyclohexanol is continuously taken out from the reaction tank. The reaction solution may be taken out in the overflow form from the upper part or from the outlet port attached to the lower part or the side surface of the reaction tank. Reaction temperature is usually 0 ℃
To 80 ° C, preferably 10 ° C to 60 ° C. Although the reaction time, that is, the residence time depends on the temperature,
It can be between 0 minutes and 10 hours.

In the reaction, a surfactant may be added to improve the contact between cyclohexene which is an "oil" and the aqueous layer containing sodium hypochlorite and sulfuric acid. From the reaction solution thus obtained, 2-chlorocyclohexanol can be isolated and purified by a known method such as extraction or distillation. The cyclohexene separated from the reaction solution can be reused in the reaction as it is or after purification treatment if necessary.

One of the important uses of 2-chlorocyclohexanol is a precursor of cyclohexene oxide, which is a raw material for pharmaceuticals, agricultural chemicals and other fine chemicals. When used for this purpose, it is possible to directly produce cyclohexene oxide without isolating 2-chlorocyclohexanol from the reaction solution obtained by the present invention. That is, cyclohexene oxide can be produced by directly adding 2-chlorocyclohexanol contained in the reaction solution of the present invention to an equimolar amount and an amount of alkali such as caustic soda or caustic potash corresponding to an excess amount of sulfuric acid and reacting. From the reaction solution, liquid separation, extraction,
High-purity cyclohexene oxide can be obtained by a known method such as distillation.

[0018]

EXAMPLES The present invention will be described more specifically below based on examples. However, the following examples do not limit the present invention in any way.

EXAMPLE 1 Cyclohexene was added to 1.2 parts sodium hypochlorite.
A continuous reaction was carried out at 20 ° C. for a residence time of 1 hour using 1.3 times the molar amount of sulfuric acid and 1.3 equivalents of sodium hypochlorite.

[Reactor] A mechanical stirrer and a thermometer were set in a 1000 ml five-necked flask. A silicone rubber tube was attached to each of the three dropping funnels for supplying raw materials, and the tip of the tube was introduced into the flask through a tube pump. On the other hand, for withdrawing the reaction liquid, a silicone rubber tube was introduced from a flask into a 1000 ml graduated cylinder through a tube pump.

[Preparation of Charged Reaction Liquid] 50.3 g of cyclohexene (purity 98%, 0.600 mol) and 21.0 g of water were charged into a flask. 278 g of sodium hypochlorite aqueous solution (concentration 1
3.4% by weight, 0.500 mol) and 159 g of sulfuric acid
(20% by weight, 0.325 mol) was simultaneously added dropwise over 1 hour. The reaction temperature was about 20 after cooling the flask in an ice-water bath.
The temperature was controlled at ° C.

After the dropping was completed, the oil layer and the water layer were separated, and each was analyzed by gas chromatography (hereinafter abbreviated as GC). The composition in 73.1 g of the oil layer was 8.55 g of cyclohexene and 51.2 g of 2-chlorocyclohexanol.
g, and the composition in 432 g of the aqueous layer was 2.55 g of 2-chlorocyclohexanol. The total amount of 2-chlorocyclohexanol was 53.8 g.

[Continuous Reaction] While the above reaction solution was sufficiently stirred, cyclohexene, an aqueous solution of sodium hypochlorite and sulfuric acid were simultaneously added dropwise, and the reaction solution was extracted, and a continuous reaction was carried out for 6 hours. Cyclohexene 5
0.3 g / h (purity 98%, 0.600 mol / h), sodium hypochlorite aqueous solution 278 g / h (concentration 13.4)
% By weight, 0.500 mol / h), sulfuric acid 159 g / h (2
(0 wt%, 0.325 mol / h), and the reaction liquid withdrawing rate was set to be constant. The reaction temperature was controlled at about 20 ° C. by cooling the flask with an ice water bath.

The reaction liquid after every 2 hours and the reaction liquid in the flask after completion of the reaction were separated into an oil layer and an aqueous layer, and G and
Analyzed in C. The composition in the total reaction liquid oil layer 524 g was 61.3 g of cyclohexene and 359 g of 2-chlorocyclohexanol, and the composition in the total reaction water layer 2899 g was 13.4 g of 2-chlorocyclohexanol. The total amount of 2-chlorocyclohexanol was 373 g.

The product of the continuous reaction portion was obtained by subtracting the composition of the charged reaction solution from the composition of the entire reaction solution, to obtain 52.8 g (0.642 mol) of cyclohexene, 319 g (2.36 mol) of 2-chlorocyclohexanol, and thus , 302 g of cyclohexene used in the continuous part (purity 98%,
Based on (3.60 mol), the average reaction results of the continuous portion were a cyclohexene conversion rate of 82% and a 2-chlorocyclohexanol selectivity of 80%.

Comparative Example 1 Cyclohexene was added to 0.9 against sodium hypochlorite.
A continuous reaction was carried out at 20 ° C. for a residence time of 1 hour using 5 moles of sulfuric acid and 1.3 equivalents of sodium hypochlorite.

[Reactor] The same reactor as in Example 1 was used.

[Preparation of Charged Reaction Liquid] 39.8 g of cyclohexene (purity: 98%, 0.475 mol) and 21.0 g of water were charged into a flask. 276 g of sodium hypochlorite aqueous solution (concentration 1
3.5% by weight, 0.500 mol) and sulfuric acid 159 g
(20% by weight, 0.325 mol) was simultaneously added dropwise over 1 hour. The reaction temperature was about 20 after cooling the flask in an ice-water bath.
The temperature was controlled at ° C.

After the dropping was completed, the oil layer and the water layer were separated, and each was analyzed by GC. The composition in the oil layer 62.8 g was 0.11 g of cyclohexene, 44.3 g of 2-chlorocyclohexanol, and the composition in the water layer 429 g was 5.23 g of 2-chlorocyclohexanol. The total 2-chlorocyclohexanol was 49.6 g.

[Continuous Reaction] While the above reaction solution was sufficiently stirred, cyclohexene, an aqueous solution of sodium hypochlorite and sulfuric acid were simultaneously added dropwise, and the reaction solution was taken out to carry out a continuous reaction for 6 hours. Cyclohexene 3
9.8 g / h (purity 98%, 0.475 mol / h), sodium hypochlorite aqueous solution 276 g / h (concentration 13.5
% By weight, 0.500 mol / h), sulfuric acid 159 g / h (2
(0 wt%, 0.325 mol / h), and the reaction liquid withdrawing rate was set to be constant. The reaction temperature was controlled at about 20 ° C. by cooling the flask with an ice water bath.

The reaction liquid after every 2 hours and the reaction liquid in the flask after completion of the reaction were separated into an oil layer and an aqueous layer, and G and
Analyzed in C. The composition in 446 g of the total reaction liquid oil layer was 16.0 g of cyclohexene and 228 g of 2-chlorocyclohexanol, and the composition of 2860 g of the total reaction water layer was 14.5 g of 2-chlorocyclohexanol. The total amount of 2-chlorocyclohexanol was 243 g.

By subtracting the composition of the charged reaction solution from the composition of the entire reaction solution, the product of the continuous reaction portion became 15.9 g (0.194 mol) of cyclohexene and 193 g (1.43 mol) of 2-chlorocyclohexanol. It was Therefore, based on 239 g of cyclohexene (purity 98%, 2.85 mol) used in the continuous part, the average reaction results of the continuous part were: cyclohexene conversion rate 93%, 2-chlorocyclohexanol selectivity 54%. .

Comparative Example 2 Cyclohexene was added to 1.2 parts of sodium hypochlorite.
A continuous reaction was carried out at 20 ° C. for a residence time of 1 hour using 1.05 equivalent of mol and sulfuric acid with respect to sodium hypochlorite.

[Reactor] The same reactor as in Example 1 was used.

[Preparation of Charged Reaction Solution] 50.3 g of cyclohexene (purity: 98%, 0.600 mol) and 21.0 g of water are charged into a flask. 276 g of sodium hypochlorite aqueous solution (concentration 1
3.5% by weight, 0.500 mol) and sulfuric acid 129 g
(20% by weight, 0.263 mol) was added dropwise at the same time in 1 hour. The reaction temperature was about 20 after cooling the flask in an ice-water bath.
The temperature was controlled at ° C.

After the dropping was completed, the oil layer and the water layer were separated and analyzed by GC. The composition in the oil layer 71.8 g was 12.4 g of cyclohexene and 45.7 g of 2-chlorocyclohexanol, and the composition in the water layer 403 g was 2.25 g of 2-chlorocyclohexanol. The total amount of 2-chlorocyclohexanol was 48.0 g.

[Continuous Reaction] While the above reaction solution was sufficiently stirred, cyclohexene, an aqueous solution of sodium hypochlorite and sulfuric acid were simultaneously added dropwise, and the reaction solution was taken out to carry out a continuous reaction for 6 hours. Cyclohexene 5
0.3 g / h (purity 98%, 0.600 mol / h), sodium hypochlorite aqueous solution 276 g / h (concentration 13.5
% By weight, 0.500 mol / h), sulfuric acid 129 g / h (2
0 wt%, 0.263 mol / h), and the reaction liquid withdrawing rate was set to be constant. The reaction temperature was controlled at about 20 ° C. by cooling the flask with an ice water bath.

The reaction liquid after every 2 hours and the reaction liquid in the flask after completion of the reaction were separated into an oil layer and an aqueous layer, and G and
Analyzed in C. The composition in 505 g of the total reaction liquid oil layer was 89.4 g of cyclohexene and 285 g of 2-chlorocyclohexanol, and the composition of 2690 g of the total reaction water layer was 9.6 g of 2-chlorocyclohexanol. The total amount of 2-chlorocyclohexanol was 295 g.

The product of the continuous reaction portion was 77.0 g (0.938 mol) of cyclohexene and 247 g (1.83 mol) of 2-chlorocyclohexanol by subtracting the composition of the charged reaction liquid from the total reaction liquid composition. It was Therefore, based on 302 g of cyclohexene (purity 98%, 3.60 mol) used in the continuous portion, the average reaction results of the continuous portion were cyclohexene conversion rate 74% and 2-chlorocyclohexanol selectivity 69%. .

Example 2 Cyclohexene was added to 1.2 parts sodium hypochlorite.
A continuous reaction was carried out at 50 ° C. for a residence time of 1 hour using twice the molar amount and 1.3 equivalents of sulfuric acid with respect to sodium hypochlorite.

[Reactor] The same reactor as in Example 1 was used.

[Preparation of Charged Reaction Solution] 50.3 g of cyclohexene (purity 98%, 0.600 mol) and 21.0 g of water were charged into a flask. 278 g of sodium hypochlorite aqueous solution (concentration 1
3.4% by weight, 0.500 mol) and 159 g of sulfuric acid
(20% by weight, 0.325 mol) was simultaneously added dropwise over 1 hour. The reaction temperature was controlled at about 50 ° C. by warming the flask with a warm bath.

After the completion of the dropping, the oil layer and the water layer were separated and each was analyzed by GC. The composition in 72.5 g of the oil layer was 7.53 g of cyclohexene and 49.5 g of 2-chlorocyclohexanol, and the composition of 431 g of the aqueous layer was 3.21 g of 2-chlorocyclohexanol. The total 2-chlorocyclohexanol was 52.7 g.

[Continuous Reaction] While the above reaction solution was sufficiently stirred, cyclohexene, an aqueous solution of sodium hypochlorite and sulfuric acid were simultaneously added dropwise, and the reaction solution was taken out to carry out a continuous reaction for 6 hours. Cyclohexene 5
0.3 g / h (purity 98%, 0.600 mol / h), sodium hypochlorite aqueous solution 278 g / h (concentration 13.4)
% By weight, 0.500 mol / h), sulfuric acid 159 g / h (2
(0 wt%, 0.325 mol / h), and the reaction liquid withdrawing rate was set to be constant. The reaction temperature was controlled at about 50 ° C. by warming the flask with a warm bath.

The reaction liquid after every 2 hours and the reaction liquid in the flask after the reaction were separated into an oil layer and an aqueous layer, and G and
Analyzed in C. The composition in the total reaction liquid oil layer 518 g was 57.8 g of cyclohexene and 349 g of 2-chlorocyclohexanol, and the composition in the total reaction water layer 2883 g was 17.8 g of 2-chlorocyclohexanol. The total amount of 2-chlorocyclohexanol was 367 g.

The product of the continuous reaction portion was obtained by subtracting the composition of the charged reaction solution from the composition of the entire reaction solution to obtain 50.3 g (0.612 mol) of cyclohexene and 314 g (2.33 mol) of 2-chlorocyclohexanol, and , 302 g of cyclohexene used in the continuous part (purity 98%,
Based on (3.60 mol), the average reaction results of the continuous portion were a cyclohexene conversion rate of 83% and a 2-chlorocyclohexanol selectivity of 78%.

Example 3 Cyclohexene at 1.5 against sodium hypochlorite
A continuous reaction was carried out using 20 mol of sulfuric acid and 1.2 equivalents of sodium hypochlorite at 20 ° C. for a residence time of 1 hour.

[Reactor] The same reactor as in Example 1 was used.

[Preparation of Charged Reaction Solution] 62.9 g of cyclohexene (purity: 98%, 0.750 mol) and 21.0 g of water were charged into a flask. 278 g of sodium hypochlorite aqueous solution (concentration 1
3.4% by weight, 0.500 mol) and 147 g of sulfuric acid
(20% by weight, 0.300 mol) was added dropwise at the same time in 1 hour. The reaction temperature was about 20 after cooling the flask in an ice-water bath.
The temperature was controlled at ° C.

After the dropping was completed, the oil layer and the water layer were separated, and each was analyzed by GC. The composition in the oil layer 74.7 g was 21.6 g of cyclohexene, 53.6 g of 2-chlorocyclohexanol, and the composition in the water layer 432 g was 3.65 g of 2-chlorocyclohexanol. The total amount of 2-chlorocyclohexanol was 57.2 g.

[Continuous Reaction] While the above reaction solution was sufficiently stirred, cyclohexene, an aqueous solution of sodium hypochlorite and sulfuric acid were simultaneously added dropwise, and the reaction solution was extracted, and a continuous reaction was carried out for 6 hours. The dropping rate is cyclohexene 6
2.9 g / h (purity 98%, 0.750 mol / h), sodium hypochlorite aqueous solution 278 g / h (concentration 13.4)
% By weight, 0.500 mol / h), sulfuric acid 147 g / h (2
(0 wt%, 0.300 mol / h), and the reaction liquid withdrawing rate was set to be constant. The reaction temperature was controlled at about 20 ° C. by cooling the flask with an ice water bath.

An oil layer and an aqueous layer were separated from the reaction solution every 2 hours and the reaction solution in the flask after completion of the reaction, and G and
Analyzed in C. The composition of 603 g of the total reaction liquid oil layer was 104 g of cyclohexene and 3 parts of 2-chlorocyclohexanol.
The composition in 65 g and 2823 g of the total reaction water layer was 20.1 g of 2-chlorocyclohexanol. The total amount of 2-chlorocyclohexanol was 385 g.

The product of the continuous reaction part was 126 g (1.53 mol) of cyclohexene and 328 g (2.44 mol) of 2-chlorocyclohexanol by subtracting the composition of the charged reaction liquid from the total reaction liquid composition. Therefore,
377 g of cyclohexene used in the continuous part (purity 98
%, 4.50 mol), the average reaction results of the continuous portion were a cyclohexene conversion of 66% and a 2-chlorocyclohexanol selectivity of 82%.

Example 4 Cyclohexene was added to 1.1 with respect to sodium hypochlorite.
A continuous reaction was carried out using 20 mol of sulfuric acid and 1.2 equivalents of sodium hypochlorite at 20 ° C. for a residence time of 1 hour.

[Reactor] The same reactor as in Example 1 was used.

[Preparation of Charged Reaction Solution] 46.1 g of cyclohexene (purity 98%, 0.550 mol) and 21.0 g of water were charged into a flask. 291 g of aqueous sodium hypochlorite solution (concentration 1
2.8% by weight, 0.500 mol) and 294 g of sulfuric acid
(10% by weight, 0.300 mol) was added dropwise at the same time in 1 hour. The reaction temperature was about 20 after cooling the flask in an ice-water bath.
The temperature was controlled at ° C.

After the completion of dropping, the oil layer and the water layer were separated and analyzed by GC. The composition in 68.9 g of the oil layer was 6.17 g of cyclohexene and 49.6 g of 2-chlorocyclohexanol, and the composition of 582 g of the water layer was 2.0 g of 2-chlorocyclohexanol. The total amount of 2-chlorocyclohexanol was 51.6 g.

[Continuous Reaction] While sufficiently stirring the above reaction solution, cyclohexene, an aqueous solution of sodium hypochlorite and sulfuric acid were simultaneously added dropwise, and the reaction solution was extracted, and a continuous reaction was carried out for 6 hours. Cyclohexene 4
6.1 g / h (purity 98%, 0.550 mol / h), aqueous sodium hypochlorite solution 291 g / h (concentration 12.8)
% By weight, 0.500 mol / h), sulfuric acid 294 g / h (2
(0 wt%, 0.300 mol / h), and the reaction liquid withdrawing rate was set to be constant. The reaction temperature was controlled at about 20 ° C. by cooling the flask with an ice water bath.

The reaction liquid after every 2 hours and the reaction liquid in the flask after completion of the reaction were separated into an oil layer and an aqueous layer, and G and
Analyzed in C. The composition in the total reaction liquid oil layer 494 g was 38.3 g of cyclohexene and 348 g of 2-chlorocyclohexanol, and the composition in the total reaction water layer 3924 g was 12.0 g of 2-chlorocyclohexanol. The total amount of 2-chlorocyclohexanol was 360 g.

The product of the continuous reaction part was 32.5 g (0.396 mol) of cyclohexene and 308 g (2.29 mol) of 2-chlorocyclohexanol by subtracting the composition of the charged reaction liquid from the total reaction liquid composition. It was Therefore, based on 277 g of cyclohexene (purity 98%, 3.30 mol) used in the continuous portion, the average reaction results of the continuous portion were cyclohexene conversion rate 88% and 2-chlorocyclohexanol selectivity 79%. .

[0061]

INDUSTRIAL APPLICABILITY According to the present invention, 2-chlorocyclohexanol, which is an important raw material for pharmaceuticals, agricultural chemicals and other fine chemicals, can be produced from cyclohexene in a good yield and by an industrially advantageous method.

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Kouki Kobayashi 161 Kambara, Kambara-cho, Anbara-gun, Shizuoka Japan Light Metal Co., Ltd.

Claims (4)

[Claims] 1. A method for producing 2-chlorocyclohexanol by reacting cyclohexene with an aqueous solution of sodium hypochlorite and an acid, wherein a molar number of cyclohexene exceeding 1 is added to 1 mole of sodium hypochlorite. , 1.1 equivalent or more of sulfuric acid is used 2
-Method for producing chlorocyclohexanol. 2. With respect to 1 mol of sodium hypochlorite,
A cyclohexene of 1.05 times mole or more is used.
A method for producing the 2-chlorocyclohexanol described. 3. The process according to claim 1, wherein the amount of cyclohexene used is 1.05 to 2 mol per mol of sodium hypochlorite, and the amount of sulfuric acid used is 1.15 to 1.5 equivalents. Law. 4. Cyclohexene, an aqueous solution of sodium hypochlorite, and sulfuric acid are continuously supplied to a reaction tank, and a reaction liquid containing 2-chlorocyclohexanol is continuously taken out from the reaction tank. Item 4. A method for producing 2-chlorocyclohexanol according to any one of Items 1 to 3.