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CN114315541B - Cyclohexanone composition and application thereof - Google Patents

Cyclohexanone composition and application thereof Download PDF

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Publication number
CN114315541B
CN114315541B CN202210048165.0A CN202210048165A CN114315541B CN 114315541 B CN114315541 B CN 114315541B CN 202210048165 A CN202210048165 A CN 202210048165A CN 114315541 B CN114315541 B CN 114315541B
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trimethyl
cyclohexen
cyclohexanone
reaction
dione
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CN114315541A (en
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郭劲资
张涛
刘英瑞
龚旭
姜天岳
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Wanhua Chemical Group Co Ltd
Wanhua Chemical Sichuan Co Ltd
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Wanhua Chemical Group Co Ltd
Wanhua Chemical Sichuan Co Ltd
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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Abstract

The invention provides a cyclohexanone composition and application thereof. The cyclohexanone composition is a composition containing 3, 5-trimethyl-3-cyclohexene-1-one, has a special composition and is prepared by taking 3, 5-trimethyl-2-cyclohexene-1-one as a raw material for reaction. The composition is useful for preparing 2, 6-trimethyl-2-cyclohexene-1, 4-dione. The method has the advantages of less catalyst consumption, low energy consumption, high product yield and easy industrialization.

Description

Cyclohexanone composition and application thereof
Technical Field
The invention belongs to the field of cyclohexanone synthesis, and particularly relates to a cyclohexanone composition and application thereof.
Background
Cyclohexanone has wide application, such as 3, 5-trimethyl-2-cyclohexen-1-one can be used as solvent for paint, ink, coating, gum, resin and nitrocellulose, and chemical synthesis intermediate, etc., and is especially suitable for vinyl resin. Is a high boiling point solvent for nitro paint and synthetic resin paint. As special paint diluents, resole phenolic resins and epoxy resins are used in combination with methyl isobutyl ketone.
The 3, 5-trimethyl cyclohexanone is used as an important high boiling point organic solvent and a medical synthesis intermediate, is mainly used in the fields of medicine, pesticide, fine chemical industry and the like, and downstream products thereof can be used as vulcanizing agents in rubber and other industries and polymer monomers in plastics industry.
3, 5-Trimethyl-3-cyclohexene-1-one is an important intermediate for synthesizing natural products such as vitamin E, carotenoid, astaxanthin and the like and spices, and particularly is a main raw material for preparing thea-ketone, wherein the thea-ketone is a precursor for preparing trimethyl hydrohydroquinone (VE main ring).
3, 5-Trimethyl-3-cyclohexene-1-one is an important raw material for preparing 2, 6-trimethyl-2-cyclohexene-1, 4-dione. However, the current methods of treating 3, 5-trimethyl-3-cyclohexen-1-one do not favor the high yield and high selectivity of 2, 6-trimethyl-2-cyclohexen-1, 4-dione products. In the U.S. Pat. No. 5,125A, triethanolamine is used as a catalyst for reaction and rectification, and the reaction solution is washed by tartaric acid and brine to obtain 3, 5-trimethyl-3-cyclohexene-1-one; the technical proposal has the defects that the purity of the obtained 3, 5-trimethyl-3-cyclohexene-1-ketone is lower and the post-treatment process is complex; the purity of the obtained 3, 5-trimethyl-3-cyclohexene-1-one can reach more than 97%, but the reaction byproducts are more, and the space-time yield is low by using oxides such as Co 3O4、CaO、Fe3O4 as a catalyst and adopting a vacuum rectification method to carry out the reaction in the U.S. patent No. 5907065A, US 6005147A. When 3, 5-trimethyl-3-cyclohexene-1-one treated by the two patents is used for preparing 2, 6-trimethyl-2-cyclohexene-1, 4-dione, ideal target products are difficult to obtain.
U.S. patent No. 4005145A discloses a method for preparing a crude product of beta-isophorone by using adipic acid as a catalyst through reactive distillation, and the purity of the obtained product can reach more than 91%. The method also has the problems of more byproducts, low space-time yield, serious equipment corrosion and the like.
In view of the above, there is a need for a cyclohexanone composition that can produce 2, 6-trimethyl-2-cyclohexene-1, 4-dione in high yield and selectivity.
Disclosure of Invention
The object of the present invention is to provide a cyclohexanone composition, which can obtain higher yield and selectivity when used for preparing 2, 6-trimethyl-2-cyclohexene-1, 4-dione.
In order to achieve the aim of the invention, the invention adopts the following technical scheme:
A cyclohexanone composition, the composition comprising the following components:
90-99.9 wt.% 3, 5-trimethyl-3-cyclohexen-1-one; and
0.01-5Wt% 3, 3-dimethyl-5-methylenecyclohex-1-one; and
0.0001-0.005Wt% 3-methyl-cyclohex-2-enone; and
0.001 To 1wt% 3, 5-trimethylcyclohexanone; and
0.001-2Wt% 3, 5-tetramethyl cyclohexanone; and
0.01-8Wt% 3, 5-trimethyl-2-cyclohexen-1-one; and
0.001-5Wt% of 2, 6-trimethyl-2-cyclohexene-1, 4-dione; and
Viii.0.0001 to 0.01wt% of 5, 5-dimethyl-3-oxocyclohex-1-eneformaldehyde; and
0.0001-0.005Wt% 2, 6-trimethylcyclohexyl-1, 4-dione; and
0.0001-0.01Wt% 2, 3-epoxy-3, 5-trimethyl-1-cyclohexanone;
preferably, the composition comprises the following components:
97-99.7wt% 3, 5-trimethyl-3-cyclohexen-1-one; and
0.1-2 Wt.% 3, 3-dimethyl-5-methylenecyclohex-1-one; and
0.001-0.002Wt% 3-methyl-cyclohex-2-enone; and
0.01 To 0.1wt% 3, 5-trimethylcyclohexanone; and
0.1-0.5Wt% 3, 5-tetramethyl cyclohexanone; and
0.01-2.7Wt% 3, 5-trimethyl-2-cyclohexen-1-one; and
0.01-0.1 Wt.% 2, 6-trimethyl-2-cyclohexene-1, 4-dione; and
Viii.0.001 to 0.004wt% of 5, 5-dimethyl-3-oxocyclohex-1-eneformaldehyde; and
0.001-0.005Wt% 2, 6-trimethylcyclohexyl-1, 4-dione; and
X.0.001-0.006wt% 2, 3-epoxy-3, 5-trimethyl-1-cyclohexanone.
In the invention, the composition is prepared by taking 3, 5-trimethyl-2-cyclohexen-1-one as a raw material for reaction.
It is another object of the present invention to provide a process for preparing a cyclohexanone composition.
A process for preparing a cyclohexanone composition, said composition being a cyclohexanone composition as described above, said process comprising: adding the catalyst, the auxiliary agent and the raw material 3, 5-trimethyl-2-cyclohexen-1-one composition into a reaction rectifying tower from a tower kettle, and heating the tower kettle to react. In the reaction, the raw material 3, 5-trimethyl-2-cyclohexen-1-one mainly undergoes isomerization reaction.
In the present invention, the reaction is carried out under the condition of a catalyst and an auxiliary agent. Preferably, the catalyst is a metal acetylacetonate and/or an inorganic base catalyst; the metal acetylacetonate may be cobalt acetylacetonate, iron acetylacetonate, copper acetylacetonate, nickel acetylacetonate, titanium acetylacetonate, etc. The inorganic base may be Na 2CO3、K2CO3, liOH, naOH, KOH, or the like. Preferably, the auxiliary agent is a nitrogen-containing compound, preferably one or more of phenazine, 2, 3-diaminophenazine, 3-indolecarboxaldehyde, 3-hydroxypyridine.
In the present invention, the catalyst is used in an amount of 0.1ppm to 10ppm, preferably 0.5ppm to 8ppm, based on the mass of the starting material 3, 5-trimethyl-2-cyclohexen-1-one.
In the present invention, the auxiliary is used in an amount of 0.1ppm to 100ppm, preferably 0.2ppm to 50ppm, based on the mass of the starting material 3, 5-trimethyl-2-cyclohexen-1-one.
In the present invention, the theoretical plate number of the reactive distillation column is 10 to 70, preferably 20 to 50; the reflux ratio is 200:1-2:1.
In the present invention, the reaction is carried out at room temperature.
In the present invention, the reaction is warmed to 120℃to 300℃and preferably 150℃to 270℃and at a pressure of 0.05 to 5barA and preferably 0.2 to 3.2barA.
It is a further object of the present invention to provide a process for preparing 2, 6-trimethyl-2-cyclohexene-1, 4-dione.
The method for preparing 2, 6-trimethyl-2-cyclohexene-1, 4-dione adopts the cyclohexanone composition as a raw material or adopts the cyclohexanone composition prepared by the preparation method of the composition as a raw material.
In the present invention, the cyclohexanone composition used in the process for preparing 2, 6-trimethyl-2-cyclohexene-1, 4-dione comprises the following components:
90-99.9 wt.% 3, 5-trimethyl-3-cyclohexen-1-one; and
0.01-5Wt% 3, 3-dimethyl-5-methylenecyclohex-1-one; and
0.0001-0.005Wt% 3-methyl-cyclohex-2-enone; and
0.001 To 1wt% 3, 5-trimethylcyclohexanone; and
0.001-2Wt% 3, 5-tetramethyl cyclohexanone; and
0.01-8Wt% 3, 5-trimethyl-2-cyclohexen-1-one; and
0.001-5Wt% of 2, 6-trimethyl-2-cyclohexene-1, 4-dione; and
Viii.0.0001 to 0.01wt% of 5, 5-dimethyl-3-oxocyclohex-1-eneformaldehyde; and
0.0001-0.005Wt% 2, 6-trimethylcyclohexyl-1, 4-dione; and
X.0.0001-0.01wt% of 2, 3-epoxy-3, 5-trimethyl-1-cyclohexanone.
In one embodiment, the method of preparing 2, 6-trimethyl-2-cyclohexene-1, 4-dione is: a reaction kettle provided with a six-blade turbine high-speed stirring paddle is used as a reactor, cyclohexanone composition, acetonitrile, a catalyst and hydroquinone are sequentially added into the reaction kettle, electric heating and mechanical stirring are started, the temperature of a reaction solution is increased, hydrogen peroxide solution is dropwise added, and the heat preservation reaction is continued. After the reaction was completed, gas chromatography was performed.
The composition prepared by the method has higher reaction activity when preparing the target product 2, 6-trimethyl-2-cyclohexene-1, 4-dione, and can obtain the target product 2, 6-trimethyl-2-cyclohexene-1, 4-dione under the conditions of less catalyst consumption and gentler conditions.
The introduction of the auxiliary agent can reduce the reaction of the raw materials and the products to generate heavy components at high temperature, thereby reducing the occurrence of side reactions and the loss of the raw materials and the products, and meanwhile, the auxiliary agent is used as a high-boiling-point nitrogen-containing compound, basically has no loss in the reaction process, can be reused after being recycled, and furthest reduces the cost of the raw materials. The introduction of the auxiliary agent enables the catalyst to achieve better reaction effect under the condition of less dosage.
Compared with the prior art, the scheme provided by the invention has the following positive effects:
1) The catalyst consumption is greatly reduced, the equipment corrosion is reduced, and the method is more beneficial to industrialized amplification and material selection.
2) The obtained cyclohexanone composition has better downstream application, and particularly has better conversion rate and selectivity when being used for preparing 2, 6-trimethyl-2-cyclohexene-1, 4-dione.
3) In the current process, the productivity is obviously increased compared with other processes, the energy consumption is reduced, and the volume of the reactive rectifying tower is reduced.
4) Compared with other processes, the reaction selectivity is better, and the byproducts are obviously reduced.
Detailed Description
The following examples will further illustrate the method provided by the present invention, but the invention is not limited to the examples listed and should include any other known modifications within the scope of the claimed invention.
The main raw material sources are shown in the following table:
The gas chromatograph is Agilent 7820A, and the gas chromatograph analysis conditions are: on-line measurement is carried out on the polysiloxane column HP-5 of Agilent gas chromatography, the temperature of a gasification chamber is 250 ℃, the temperature of a detector is 250 ℃, and the temperature of the column is programmed to rise: 50 ℃ for 1min;80 ℃ for 1min;10 ℃ per minute to 250 ℃ per minute, and the sample injection amount is 0.2 mu L.
Example 1
Adding a mixed solution of 20kg of raw materials of 3, 5-trimethyl-2-cyclohexen-1-one, 40.0mg of cobalt acetylacetonate and 900.0mg of phenazine into a stainless steel rectifying tower kettle with a theoretical plate number of 45 blocks at normal temperature, maintaining the tower top pressure of the reaction rectifying tower at 2.4barA, then slowly heating the tower kettle to boiling, maintaining the kettle temperature at 259 ℃, slowly raising the reflux amount of the tower top to 80kg/h after the reflux is established at the tower top, fully refluxing for about 1h, starting to extract materials at a rate of 5.0kg/h at the same time as fresh raw materials of 3, 5-trimethyl-2-cyclohexen-1-one at the tower bottom, maintaining the reaction liquid volume of the tower kettle constant in the whole rectifying process, maintaining the kettle temperature at 259-261 ℃ after the stable operation for 720h, slightly raising the temperature along with the time, and carrying out gas phase analysis on the materials extracted from the tower top, wherein the mass composition is as follows:
2, 6-trimethyl-2-cyclohexene-1, 4-dione was prepared using the cyclohexanone composition obtained above.
Preparing 2, 6-trimethyl-2-cyclohexene-1, 4-dione by using the cyclohexanone composition obtained above as a raw material: drying walnut shell at 120deg.C to constant weight, pulverizing, and sieving with 160 mesh sieve. The activator adopts H 3PO4 with the mass fraction of 40%, 300g of activator is added into 50g of walnut shell powder, and after mixing and standing for 20H, the mixture is dried at 120 ℃, and then is put into a tube furnace for pyrolysis at 550 ℃ for 1H (nitrogen protection). After cooling to room temperature, the activated carbon is taken out and washed to be neutral. And (3) drying the activated carbon, cooling, crushing, sieving with a 200-mesh sieve, and then placing into a dryer for storage for standby, wherein the prepared walnut shell activated carbon is marked as W-AC.
Weighing 4g of nano Y 2O3, 4g of nano ZrO 2 and 50g of carrier W-AC, grinding for 30min in an agate mortar, transferring into a beaker, adding 300g of pure water, and stirring for 1h to fully mix the active components and the carrier. And (3) carrying out ultrasonic oscillation on the mixed sample after stirring for 2 hours at the frequency of 100Hz and 25 ℃ to further fully mix the sample. And (5) placing the sample into a constant temperature box for drying. Taking out and grinding to obtain Y 2O3-ZrO2/W-AC.
Preparation of M mXn-Y2O3-ZrO2/W-AC: all Y 2O3-ZrO2/W-AC obtained was dispersed in 100g of water-dissolved 1.2g of magnesium chloride aqueous solution and sonicated for 1h. Followed by vigorous stirring at 60℃for 10h. Stopping stirring, standing, discarding supernatant, centrifuging, and drying the precipitate to obtain MgCl 2-Y2O3-ZrO2/W-AC catalyst (denoted as catalyst a). According to XPS test of Y, zr and Mg element contents, the catalyst a is obtained as a W-AC carrier: y 2O3：ZrO2：MgCl2 = 100.0:8.0:8.0:2.1 (mass ratio).
A reaction kettle provided with a six-blade turbine high-speed stirring paddle is used as a reactor. 1382g of cyclohexanone composition prepared by the method, 1658g of acetonitrile, 6.90g of catalyst a and 41.46g of hydroquinone are sequentially added into a reaction kettle; and (3) starting electric heating and mechanical stirring, heating the reaction solution to 30 ℃, dropwise adding 2429g of 35% hydrogen peroxide solution, dropwise adding for 5 hours, and continuing to perform heat preservation reaction for 2 hours. After the reaction, the conversion of the raw material 3, 5-trimethyl-2-cyclohexen-1-one was 99.81%, and the selectivity of 2, 6-trimethyl-2-cyclohexene-1, 4-dione was 96.24%, and the yield of 2, 6-trimethyl-2-cyclohexene-1, 4-dione was 96.0% by gas chromatography.
Compared with the prior art, the preparation process of the 2, 6-trimethyl-2-cyclohexene-1, 4-dione has the advantages that the dosage of the catalyst a is reduced by 80%, the reaction time is reduced by 30%, and the reaction yield is improved by about 1.5%.
Examples 2 to 7
The operating conditions were varied and the procedure was as described in example 1, with additional conditions and results as set forth in the following table:
Comparative example 1
Adding 20kg of mixed solution of 3, 5-trimethyl-2-cyclohexen-1-one and 4.0g of KOH into a stainless steel rectifying tower kettle with 45 theoretical plates at normal temperature, maintaining the top pressure of the reactive rectifying tower at 2.4barA, then slowly heating the tower kettle to boiling, maintaining the kettle temperature at 258 ℃, slowly increasing the reflux quantity of the tower top to 80kg/h after reflux is established at the tower top, starting to extract materials at the rate of 5kg/h after total reflux for about 1h, simultaneously feeding fresh raw materials 3, 5-trimethyl-2-cyclohexen-1-one into the tower kettle at the feed rate of 5.0kg/h, maintaining the reaction liquid volume of the tower kettle constant in the whole rectifying process, maintaining the kettle temperature at 258-271 ℃ with the lapse of time (the temperature is obviously increased), and performing gas phase analysis on the materials extracted from the tower top, wherein the components are as follows:
The procedure was exactly the same as in example 1, except that 3, 5-trimethyl-3-cyclohexene-1-one obtained above was used as a starting material to prepare 2, 6-trimethyl-2-cyclohexene-1, 4-dione, and after completion of the reaction, gas chromatography analysis was performed to determine that the starting material 3, 5-trimethyl-2-cyclohexene-1-one had a conversion of 82.12%, a selectivity of 2, 6-trimethyl-2-cyclohexene-1, 4-dione was 73.29% and a yield of 2, 6-trimethyl-2-cyclohexene-1, 4-dione was 60.1%.
Those skilled in the art will appreciate that certain modifications and adaptations of the invention are possible and can be made under the teaching of the present specification. Such modifications and adaptations are intended to be within the scope of the present invention as defined in the appended claims.

Claims (9)

1. A process for preparing a cyclohexanone composition, characterized in that the process comprises: adding a catalyst, an auxiliary agent and a raw material 3, 5-trimethyl-2-cyclohexen-1-one composition into a reaction rectifying tower from a tower kettle, and heating the tower kettle to react;
wherein the catalyst is acetylacetone metal and/or inorganic base catalyst;
Wherein the auxiliary agent is one or more of phenazine, 2, 3-diaminophenazine, 3-indolecarboxaldehyde and 3-hydroxypyridine.
2. The process according to claim 1, wherein the catalyst is used in an amount of 0.1ppm to 10ppm based on the mass of the starting 3, 5-trimethyl-2-cyclohexen-1-one.
3. The process according to claim 2, wherein the catalyst is used in an amount of 0.5ppm to 8ppm based on the mass of the starting 3, 5-trimethyl-2-cyclohexen-1-one.
4. The method according to claim 1, wherein the auxiliary is used in an amount of 0.1ppm to 100ppm based on the mass of the starting material 3, 5-trimethyl-2-cyclohexen-1-one.
5. The process according to claim 4, wherein the auxiliary is used in an amount of 0.2ppm to 50ppm based on the mass of the starting material 3, 5-trimethyl-2-cyclohexen-1-one.
6. The method according to claim 1, wherein the theoretical plate number of the reactive distillation column is 10 to 70; the reflux ratio is 200:1-2:1;
and/or, the reaction is carried out at normal temperature;
and/or, the reaction is warmed to 120 ℃ to 300 ℃ and the pressure is 0.05barA to 5barA.
7. The method according to claim 6, wherein the theoretical plate number of the reactive distillation column is 20 to 50;
And/or the reaction is warmed to 150 ℃ to 270 ℃ and the pressure is 0.2barA to 3.2barA.
8. A process according to claim 1, characterized in that the cyclohexanone composition prepared by the process comprises the following components:
90-99.9 wt.% 3, 5-trimethyl-3-cyclohexen-1-one; and
0.01-5Wt% 3, 3-dimethyl-5-methylenecyclohex-1-one; and
0.0001-0.005Wt% 3-methyl-cyclohex-2-enone; and
0.001 To 1wt% 3, 5-trimethylcyclohexanone; and
0.001-2Wt% 3, 5-tetramethyl cyclohexanone; and
0.01-8Wt% 3, 5-trimethyl-2-cyclohexen-1-one; and
0.001-5Wt% of 2, 6-trimethyl-2-cyclohexene-1, 4-dione; and
Viii.0.0001 to 0.01wt% of 5, 5-dimethyl-3-oxocyclohex-1-eneformaldehyde; and
0.0001-0.005Wt% 2, 6-trimethylcyclohexyl-1, 4-dione; and
X.0.0001-0.01wt% of 2, 3-epoxy-3, 5-trimethyl-1-cyclohexanone.
9. The method according to claim 8, wherein the cyclohexanone composition comprises the following components:
97-99.7wt% 3, 5-trimethyl-3-cyclohexen-1-one; and
0.1-2 Wt.% 3, 3-dimethyl-5-methylenecyclohex-1-one; and
0.001-0.002Wt% 3-methyl-cyclohex-2-enone; and
0.01 To 0.1wt% 3, 5-trimethylcyclohexanone; and
0.1-0.5Wt% 3, 5-tetramethyl cyclohexanone; and
0.01-2.7Wt% 3, 5-trimethyl-2-cyclohexen-1-one; and
0.01-0.1 Wt.% 2, 6-trimethyl-2-cyclohexene-1, 4-dione; and
Viii.0.001 to 0.004wt% of 5, 5-dimethyl-3-oxocyclohex-1-eneformaldehyde; and
0.001-0.005Wt% 2, 6-trimethylcyclohexyl-1, 4-dione; and
X.0.001-0.006wt% 2, 3-epoxy-3, 5-trimethyl-1-cyclohexanone.
CN202210048165.0A 2022-01-17 2022-01-17 Cyclohexanone composition and application thereof Active CN114315541B (en)

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