CN105016969B - Method for separating cyclohexanol and cyclohexanone from KA oil - Google Patents
Method for separating cyclohexanol and cyclohexanone from KA oil Download PDFInfo
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- CN105016969B CN105016969B CN201510427752.0A CN201510427752A CN105016969B CN 105016969 B CN105016969 B CN 105016969B CN 201510427752 A CN201510427752 A CN 201510427752A CN 105016969 B CN105016969 B CN 105016969B
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- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention discloses a method for separating cyclohexanol and cyclohexanone from KA oil, which utilizes the characteristic that hydrogen peroxide and cyclohexanone react at low temperature to generate cyclohexanone peroxide precipitate, and cyclohexanone peroxide is easy to hydrolyze and reduce at higher temperature to generate cyclohexanone, and the cyclohexanone and cyclohexanol in the KA oil are separated; the method is simple to operate, low in energy consumption and capable of effectively realizing KA oil separation. The method can further utilize a reaction separation synchronous reactor to separate the KA oil, the reaction separation synchronous reactor comprises a stirring reaction tower and a settling tower communicated with the bottom of the stirring reaction tower, cyclohexanone in the KA oil reacts with hydrogen peroxide in the stirring reaction tower to generate cyclohexanone peroxide, and the cyclohexanone peroxide settles to the settling tower through self gravity, so that the timely separation of the cyclohexanone peroxide and a reaction liquid is realized, the hydrolysis side reaction of the cyclohexanone peroxide is prevented, the separation efficiency of the cyclohexanone and the cyclohexanol is further improved, and the purity of the obtained cyclohexanol and cyclohexanone is further improved.
Description
Technical Field
The invention relates to a method for separating cyclohexanol and cyclohexanone from KA oil, belonging to the technical field of petrochemical industry.
Background
The KA oil is a mixture of cyclohexanol and cyclohexanone, and is a basic chemical raw material for producing Nilun 6 and Nilun 66. Currently, in industry, cyclohexane liquid phase air oxidation is the main method for preparing KA oil, such as the non-catalytic oxidation method of hollandamami cabo company, and is mainly prepared by cyclohexane liquid phase air oxidation under the conditions of high temperature and high pressure. The current industrial optimum conversion rate of cyclohexane is 4%, and the yield of KA oil is 82%. The patent (publication No. CN 1191218A) discloses a method for preparing KA oil by cyclohexane air oxidation under the catalysis of metalloporphyrin, according to the method, a mesopetro-chemical catalyst is originally introduced into a large industrial device with 45kt KA oil and 70kt KA oil, 2ppm of tetraphenylporphyrin iron mu-dimer (CAS No. 12582-61-5) and tetraphenylporphyrin cobalt (CAS No. 14172-90-8) are respectively adopted as catalysts, and the cyclohexane conversion rate of 7-8% and the KA oil yield of 85-88% are obtained under the conditions of 145 ℃ and 8 atmospheres, so that the production benefit is obviously improved.
In the prior art, the KA oil prepared by a cyclohexane oxidation method is a mixture of cyclohexanol and cyclohexanone, and generally, the KA oil is directly used as a raw material, adipic acid is further prepared by oxidation, and if cyclohexanone or cyclohexanol is to be obtained, the KA oil needs to be separated. However, cyclohexanone and cyclohexanol are mutually soluble and have similar boiling points, and separation by a conventional rectification separation method is difficult to realize. There are few reports on KA oil separation, and the methods mainly include three types: 1. the vacuum rectification separation needs high vacuum degree in the separation process, a high-efficiency rectification tower needs to be adopted for carrying out vacuum rectification under the pressure of about 4kPa to ensure that the content of cyclohexanone in a rectification product reaches 98-99 percent, the number of required theoretical plates is 15, and the method has high energy consumption, complex operation and high cost. 2. The membrane pervaporation method is to perform pervaporation on different intermolecular forces of cyclohexanol and cyclohexanone through a polymer membrane. It is possible to achieve selective separation of cyclohexanone and cyclohexanol mainly by incorporating into the polymer a group having some specific role, such as inter-hydrogen bonding. In the prior art, a grafted nylon-6 polyoxyethylene membrane is prepared by reacting nylon-6 with ethylene oxide, and the separation of cyclohexanol and cyclohexanone is realized because the hydrogen bond acting force between the hydroxyl group of cyclohexanol and the hydroxyl group on a polyoxyethylene grafted chain is relatively strong. Although this membrane pervaporation method is widely concerned because of its energy saving, it is still in the laboratory stage and cannot be applied industrially because of its high cost. 3. Extractive distillation separation processes vary the relative volatility of the desired separation components within the column by continuously adding a substance (extractant) of lower relative volatility than the separation components near the top of the column. The literature ("research on the binary system extraction, rectification and separation of cyclohexanol and cyclohexanone", great treatise, 5.14.2006) discloses that diethylene glycol is used as a solvent, the theoretical number of pedals is 39, and the number of pedals required for subsequent separation is 11. The method can realize the separation of cyclohexanone and cyclohexanol, but has the disadvantages of complex operation, high energy consumption and high separation cost.
Disclosure of Invention
Aiming at the defects of complex operation, high energy consumption and high cost of KA separation in the prior art, the invention aims to provide the method which is simple to operate, has low energy consumption, can effectively realize the separation of cyclohexanol and cyclohexanone in KA oil, has low cost and meets the requirement of industrial production.
In order to realize the technical purpose of the invention, the invention provides a method for separating cyclohexanol and cyclohexanone from KA oil, which comprises the steps of slowly adding hydrogen peroxide into the KA oil at the temperature of 15-40 ℃ for stirring reaction, separating out precipitate, stopping the reaction until no precipitate is separated out after the reaction is carried out, and carrying out solid-liquid separation; cooling the liquid mixture obtained by solid-liquid separation at the temperature below 10 ℃, and collecting the upper-layer solid to obtain cyclohexanol; and (3) putting the solid obtained by solid-liquid separation into water, heating to 60-80 ℃ for hydrolysis reaction, and collecting upper-layer oily liquid after the hydrolysis reaction is finished to obtain the cyclohexanone.
In the technical scheme of the invention, cyclohexanone and hydrogen peroxide are firstly utilized to generate stable cyclohexanone peroxide precipitate at about 30 ℃, so that the cyclohexanone peroxide and cyclohexanol are effectively separated; on the basis, cyclohexanone is reduced by the hydrolysis of cyclohexanone peroxide in water, and high-purity cyclohexanone is obtained. Therefore, the technical scheme of the invention realizes the separation of the cyclohexanone and the cyclohexanol by a simple and low-energy-consumption method, and solves the defects of high energy consumption and complex operation of membrane distillation separation, extraction rectification separation and other methods in the prior art.
According to the technical scheme, a relatively pure cyclohexanone peroxide product can be obtained, can be directly used as an organic peroxide, and can solve the problems of poor solubility of hydrogen peroxide in most of organic substances and low oxidation efficiency in the oxidation process of hydrogen peroxide in the conventional organic synthesis.
The method for separating cyclohexanol and cyclohexanone from KA oil can be used for separating cyclohexanol and cyclohexanone from KA oil or can be used for separating cyclohexanol and cyclohexanone from KA oil by utilizing a reaction separation synchronous reactor, wherein the reaction separation synchronous reactor comprises a stirring reaction tower and a settling tower, the settling tower is arranged at the bottom of the stirring reaction tower, and the communication and the partition of the settling tower and the stirring reaction tower are controlled by a valve; a stirrer is arranged in the stirring reaction tower, and a KA oil feeding port and a hydrogen peroxide feeding port are formed in the top of the stirring reaction tower; a liquid discharge branch pipe is arranged at the top of the settling tower; when the reaction is carried out, a valve between the settling tower and the stirring reaction tower is opened to communicate the settling tower and the stirring reaction tower, KA oil is injected from a KA oil inlet, hydrogen peroxide is added from the hydrogen peroxide inlet until the KA oil covers a stirrer at the bottom of the stirrer, the temperature in the stirring reaction tower is controlled within the range of 15-40 ℃, under the stirring condition, the hydrogen peroxide is in full contact with cyclohexanone in the KA oil in the stirring reaction tower and reacts, cyclohexanone peroxide generated by the reaction is separated out in a solid form and simultaneously descends into the settling tower under the action of self gravity, the KA oil in the settling tower is extruded and ascended by the settled cyclohexanone peroxide to enter the stirring reaction tower, the reaction is continuously carried out, the valve between the settling tower and the stirring reaction tower is closed until the settling tower is filled with the cyclohexanone peroxide, a liquid drainage branch pipe is opened to recover reaction liquid, and then the settling tower is taken down, carrying out hydrolysis treatment on the obtained cyclohexanone peroxide to obtain cyclohexanone; and when no precipitate is separated out from the stirring reaction tower, stopping the reaction, closing the valve, collecting the reaction liquid in the stirring reaction tower, cooling to realize solid-liquid separation, and collecting the upper-layer solid to obtain the cyclohexanol.
The technical scheme of the invention further adopts a reaction separation synchronous reactor to separate cyclohexanol and cyclohexanone in KA oil, and mainly solves the technical problems that in the process of continuously reacting cyclohexanone and hydrogen peroxide to generate cyclohexanone peroxide, along with the continuous reaction, the concentration of water entering along with hydrogen peroxide in reaction liquid is higher and higher, so that the hydrolysis reaction probability of cyclohexanone peroxide is increased, and the cyclohexanone peroxide is difficult to completely generate cyclohexanone peroxide for precipitation. According to the technical scheme, the reaction separation synchronous reactor is used for synchronously generating the cyclohexanone peroxide and precipitating and separating the cyclohexanone peroxide, so that the hydrolysis of the cyclohexanone peroxide is effectively prevented, and the separation efficiency is greatly increased.
The method for separating cyclohexanol and cyclohexanone from KA oil further comprises the following preferable scheme:
in the preferred scheme, cyclohexanone in the KA oil and hydrogen peroxide generate cyclohexanone peroxide precipitate at the temperature of 15-40 ℃, and the cyclohexanone peroxide is subjected to hydrolysis reaction in water at the temperature of 60-80 ℃ to be reduced into hydrogen peroxide and cyclohexanone. According to the preferable technical scheme, the peroxide generated by cyclohexanone and hydrogen peroxide at low temperature can stably exist at normal temperature, and the existing solid-liquid separation means is mature, so that high-purity cyclohexanone peroxide can be obtained. The hydrolysis reaction of the cyclohexanone peroxide is thorough, and the cyclohexanone is easy to separate from water, so that the yield and the purity of the cyclohexanone are improved.
In a preferred scheme, the concentration of the hydrogen peroxide is preferably between 30 and 60 percent by mass.
In a preferred embodiment, the hydrolysis reaction is carried out until all of the solids in the solution have been decomposed.
In a preferred embodiment, the method for separating cyclohexanone peroxide from the reaction solution can be performed by a solid-liquid separation method which is relatively conventional in the prior art. Including filtration, centrifugation, and the like.
In a preferable scheme, in the process of separating cyclohexanol and cyclohexanone in KA oil by using the reaction separation synchronous reactor, when no precipitate is separated out in the stirring reaction tower, the reaction liquid in the stirring reaction tower is collected, kept stand and cooled to be below 10 ℃, so that solid-liquid layering is realized, and the upper layer of solid is cyclohexanol.
In the preferred scheme, the cyclohexanone peroxide is subjected to hydrolysis reaction at the temperature of 60-80 ℃, and after the hydrolysis reaction is finished, the upper-layer oily liquid is collected to obtain the cyclohexanone.
In a preferred scheme, a heating jacket is arranged outside the stirring reaction tower so as to maintain the temperature of the stirring reaction tower stable.
In the preferred scheme, the dropping rate of the hydrogen peroxide is controlled by a constant-pressure dropping funnel.
Compared with the prior art, the technical scheme of the invention has the beneficial technical effects that: the chemical reaction characteristics of hydrogen peroxide and cyclohexanone are ingeniously utilized for separating cyclohexanone and cyclohexanol for the first time, the separation efficiency is high, high-purity cyclohexanone and cyclohexanol can be obtained, the process steps are greatly simplified, and the energy consumption and the production cost are greatly reduced compared with a rectification separation process. The optimized process for separating cyclohexanol and cyclohexanone in KA oil by using the reaction separation synchronous reactor effectively realizes the synchronous generation and separation of cyclohexanone peroxide, and further improves the separation effect of cyclohexanone and cyclohexanol.
Drawings
FIG. 1 is a schematic view of a reaction separation synchronous reactor apparatus according to the present invention; 1 is a stirring reaction tower, 2 is a settling tower, 3 is a stirrer, 4 is a KA oil feeding port, 5 is a hydrogen peroxide feeding port, 6 is a heating sleeve, 7 is a stirrer, 8 is a valve, 9 is a liquid discharge branch pipe, and 10 is a constant-pressure dropping funnel.
Detailed Description
The following examples are intended to further illustrate the present disclosure, but not to limit the scope of the invention as claimed.
The reaction separation synchronous reactor device of the present invention will be described with reference to FIG. 1. The main body of the reaction separation synchronous reactor device comprises a stirring reaction tower 1 and a settling tower 2. The settling tower 2 is arranged at the bottom of the stirring reaction tower 1, and the communication and the partition of the settling tower and the stirring reaction tower are controlled by a valve 8. A cyclohexanone feeding port 4 and a hydrogen peroxide feeding port 5 are arranged at the top of the stirring reaction tower 1; the hydrogen peroxide feeding port 5 is connected with a constant pressure dropping funnel 10, and the dropping speed of the hydrogen peroxide is controlled by the constant pressure dropping funnel 10. The stirrer 3 is arranged in the stirring reaction tower 1, and the stirrer 7 is arranged at the bottom of the stirrer 3. The heating jacket 6 is arranged outside the stirring reaction tower 1, and the temperature of the heating jacket 6 is set through a computer program so as to maintain the reaction temperature in the stirring reaction kettle 1. The upper part of the settling tower 2 is provided with a liquid discharge branch pipe 9 which is mainly used for recovering a small amount of reaction liquid in the settling tower 2.
Example 1
Slowly adding 55% hydrogen peroxide into a stirring reaction kettle filled with KA oil for stirring reaction, keeping the temperature of the stirring reaction kettle at 15 ℃, continuously separating out cyclohexanone peroxide precipitate by reaction, stopping the reaction until no precipitate is separated out by the reaction, filtering and separating to obtain cyclohexanone peroxide, standing and cooling filtrate obtained by filtering and separating in a cold water bath at 5 ℃, and collecting upper-layer solid to obtain cyclohexanol; and (3) putting the separated cyclohexanone peroxide into a large amount of water, heating to 60 ℃ for hydrolysis reaction, cooling after the hydrolysis reaction is finished, and collecting upper-layer oily liquid to obtain the cyclohexanone. Carrying out chromatographic analysis on the collected cyclohexanone and cyclohexanol products, wherein the purity of the cyclohexanol is 97.5 percent, and the purity of the cyclohexanone is 98 percent; and according to the raw material components, the recovery rate of cyclohexanol is 95.2%, and the recovery rate of cyclohexanone is 97.1%.
Example 2
Slowly adding 35% hydrogen peroxide into a stirring reaction kettle filled with KA oil for stirring reaction, keeping the temperature of the stirring reaction kettle at 30 ℃, continuously separating out cyclohexanone peroxide precipitate by reaction, stopping the reaction until no precipitate is separated out by the reaction, filtering and separating to obtain cyclohexanone peroxide, standing and cooling filtrate obtained by filtering and separating in an ice water bath, and collecting upper-layer solid to obtain cyclohexanol; and (3) putting the separated cyclohexanone peroxide into a large amount of water, heating to 70 ℃ for hydrolysis reaction, cooling after the hydrolysis reaction is finished, and collecting upper-layer oily liquid to obtain the cyclohexanone. Carrying out chromatographic analysis on the collected cyclohexanone and cyclohexanol products, wherein the purity of the cyclohexanol is 96.1 percent, and the purity of the cyclohexanone is 97 percent; and the recovery rate of cyclohexanol and cyclohexanone was 95.0% and 96.4%, respectively, based on the raw material components.
Example 3
The separation of KA oil is achieved with the apparatus of fig. 1. Opening a valve between a settling tower and a stirring reaction tower to communicate the settling tower and the stirring reaction tower, injecting KA oil from a KA oil inlet, adding 45% hydrogen peroxide from the hydrogen peroxide inlet when the KA oil covers a stirrer at the bottom of a stirrer, controlling the temperature in the stirring reaction tower to be 40 ℃, under the stirring condition, fully contacting the hydrogen peroxide with cyclohexanone in the KA oil in the stirring reaction tower and reacting, separating out the cyclohexanone peroxide generated by the reaction in a solid form, simultaneously descending into the settling tower under the action of self gravity, extruding and lifting the KA oil in the settling tower by the settled cyclohexanone peroxide into the stirring reaction tower, reacting continuously, closing the valve between the settling tower and the stirring reaction tower until the settling tower is filled with the cyclohexanone peroxide, opening a liquid discharge branch pipe to recover a small amount of reaction liquid, taking off the settling tower, placing the cyclohexanone peroxide into a large amount of water, heating to 75 ℃ for hydrolysis reaction, and after the hydrolysis reaction is finished, cooling, and collecting upper oily liquid to obtain the cyclohexanone. When the settling tower is filled with cyclohexanone peroxide and cyclohexanone in the stirring reaction tower is not completely reacted, taking down the cyclohexanone peroxide in the settling tower for treatment, connecting a new settling tower to the bottom of the stirring reaction tower, opening a valve, continuing the precipitation reaction, alternately performing the steps until no precipitate is generated in the reaction kettle, closing the valve, collecting reaction liquid in the reaction kettle, standing and cooling in a cold water bath at 5 ℃, collecting upper-layer solid, and obtaining cyclohexanol. Carrying out chromatographic analysis on the collected cyclohexanone and cyclohexanol products, wherein the purity of the cyclohexanol is 99.5 percent, and the purity of the cyclohexanone is 99.8 percent; and according to the raw material components, the recovery rate of cyclohexanol is 98.5%, and the recovery rate of cyclohexanone is 98.6%.
Example 4
The separation of KA oil is achieved with the apparatus of fig. 1. Opening a valve between a settling tower and a stirring reaction tower to communicate the settling tower and the stirring reaction tower, injecting KA oil from a KA oil inlet, adding 30% hydrogen peroxide from the hydrogen peroxide inlet when the KA oil covers a stirrer at the bottom of a stirrer, controlling the temperature in the stirring reaction tower to be 25 ℃, under the stirring condition, fully contacting the hydrogen peroxide with cyclohexanone in the KA oil in the stirring reaction tower and reacting, separating out the cyclohexanone peroxide generated by the reaction in a solid form, simultaneously descending into the settling tower under the action of self gravity, extruding and lifting the KA oil in the settling tower into the stirring reaction tower by the settled cyclohexanone peroxide, reacting continuously, closing the valve between the settling tower and the stirring reaction tower until the settling tower is filled with the cyclohexanone peroxide, opening a liquid discharge branch pipe to recover a small amount of reaction liquid, taking off the settling tower, placing the cyclohexanone peroxide into a large amount of water, heating to 65 ℃ for hydrolysis reaction, and after the hydrolysis reaction is finished, cooling, and collecting upper oily liquid to obtain the cyclohexanone. When the settling tower is filled with cyclohexanone peroxide and cyclohexanone in the stirring reaction tower is not completely reacted, taking down the cyclohexanone peroxide in the settling tower for treatment, connecting a new settling tower to the bottom of the stirring reaction tower, opening a valve, continuing the precipitation reaction, alternately performing the steps until no precipitate is generated in the reaction kettle, closing the valve, collecting reaction liquid in the reaction kettle, standing and cooling in a 7 ℃ cold water bath, and collecting upper-layer solid to obtain cyclohexanol. Carrying out chromatographic analysis on the collected cyclohexanone and cyclohexanol products, wherein the purity of the cyclohexanol is 99.7 percent, and the purity of the cyclohexanone is 99.8 percent; and according to the calculation of the components of the raw materials, the recovery rate of cyclohexanol is 98.9%, and the recovery rate of cyclohexanone is 99.1%.
Claims (6)
1. The method for separating cyclohexanol and cyclohexanone from KA oil is characterized in that a reaction separation synchronous reactor is used for separating cyclohexanol and cyclohexanone in the KA oil, the reaction separation synchronous reactor comprises a stirring reaction tower and a settling tower, the settling tower is arranged at the bottom of the stirring reaction tower, and the communication and the partition of the settling tower and the stirring reaction tower are controlled through a valve; a stirrer is arranged in the stirring reaction tower, and a KA oil feeding port and a hydrogen peroxide feeding port are formed in the top of the stirring reaction tower; a liquid discharge branch pipe is arranged at the top of the settling tower; when the reaction is carried out, a valve between the settling tower and the stirring reaction tower is opened to communicate the settling tower and the stirring reaction tower, KA oil is injected from a KA oil inlet, hydrogen peroxide is added from the hydrogen peroxide inlet until the KA oil covers a stirrer at the bottom of the stirrer, the temperature in the stirring reaction tower is controlled within the range of 15-40 ℃, under the stirring condition, the hydrogen peroxide is in full contact with cyclohexanone in the KA oil in the stirring reaction tower and reacts, cyclohexanone peroxide generated by the reaction is separated out in a solid form and simultaneously descends into the settling tower under the action of self gravity, the KA oil in the settling tower is extruded and ascended by the settled cyclohexanone peroxide to enter the stirring reaction tower, the reaction is continuously carried out, the valve between the settling tower and the stirring reaction tower is closed until the settling tower is filled with the cyclohexanone peroxide, a liquid drainage branch pipe is opened to recover reaction liquid, and then the settling tower is taken down, carrying out hydrolysis treatment on the obtained cyclohexanone peroxide to obtain cyclohexanone; and when no precipitate is separated out from the stirring reaction tower, stopping the reaction, closing the valve, collecting the reaction liquid in the stirring reaction tower, cooling to realize solid-liquid separation, and collecting the upper-layer solid to obtain the cyclohexanol.
2. The method according to claim 1, wherein the concentration of hydrogen peroxide is 30-60% by mass.
3. The method as claimed in claim 1, wherein when no precipitate is precipitated in the stirred reaction column, the reaction solution in the stirred reaction column is collected, kept stand and cooled to below 10 ℃ to realize solid-liquid separation, and the upper solid is cyclohexanol.
4. The method according to claim 1, wherein the cyclohexanone peroxide is subjected to hydrolysis reaction at a temperature of 60-80 ℃, and after the hydrolysis reaction is completed, the upper oily liquid is collected to obtain cyclohexanone.
5. The method as claimed in claim 1, wherein the stirring reaction tower is externally provided with a heating jacket to maintain the temperature of the stirring reaction tower stable.
6. The method as claimed in claim 1, wherein the dropping rate of the hydrogen peroxide solution is controlled by a constant pressure dropping funnel.
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| CN104177218A (en) * | 2013-05-24 | 2014-12-03 | 中国石油化工股份有限公司 | Method for recovering main compositions from cyclohexanone by-product X oil |
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| CN104177218A (en) * | 2013-05-24 | 2014-12-03 | 中国石油化工股份有限公司 | Method for recovering main compositions from cyclohexanone by-product X oil |
Non-Patent Citations (1)
| Title |
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| Structure of Peroxides Derived from Cyclohexanone and Hydrogen Peroxide;M. S. KHARASCH等;《Journal of Organic Chemistry》;19581231;第23卷(第9期);第1324页右栏第2段、第1322页化学反应式1-2、第1323页第4段及化学式反应4-7 * |
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