A method for preparing diacetone alcohol and mesityl oxide from each other

Abstract

The present invention relates to the technical field of organic synthesis, and in particular to a method for preparing diacetone alcohol and mesityl oxide from each other. A raw material liquid comprises acetone, mesityl oxide and diacetone alcohol. The preparation of mesityl oxide comprises the following specific steps: (1) preparing a raw material liquid, wherein the proportion of acetone and diacetone alcohol together is greater than the proportion of mesityl oxide; (2) adding a sulfonated resin catalyst and water into the raw material liquid, and catalyzing the raw material liquid by using the sulfonated resin, and the reaction temperature is 40-80°C. The present invention utilizes sulfuric acid, hydrochloric acid, p-toluenesulfonic acid and the sulfonated resin as catalysts, and can select diacetone alcohol to prepare mesityl oxide or select mesityl oxide to prepare diacetone alcohol according to market demand, thereby adjusting the product production structure and preventing product sedimentation.

Description

Technical Field

[0001] The present invention relates to the technical field of organic synthesis, and in particular to a method for preparing diacetone alcohol from mesityl oxide. Background Art

[0002] In common chemical plants, diacetone alcohol is usually prepared by catalytic condensation of acetone. In the preparation of mesityl oxide, diacetone alcohol is usually catalytically dehydrated under acidic conditions, often using phosphoric acid, sulfuric acid, etc. as catalysts, and is separated by reactive distillation to obtain mesityl oxide. The chemical formula of acetone is: CH3COCH3, the chemical formula of mesityl oxide is: (CH3)2CCHCOCH3, and the chemical formula of diacetone alcohol is: (CH3)2COHCH2COCH3.

[0003] If the preparation of diacetone alcohol requires catalytic condensation of acetone, and if the preparation of mesityl oxide requires catalytic dehydration of diacetone alcohol under acidic conditions, the two reaction systems are carried out separately, requiring two different sets of equipment. In addition, mesityl oxide is produced in the process of preparing diacetone alcohol from acetone, and diacetone alcohol is required for the preparation of mesityl oxide. Therefore, in chemical production, there will always be excess mesityl oxide, and mesityl oxide is easy to precipitate. Summary of the Invention

[0004] The object of the present invention is to provide a method for preparing diacetone alcohol and mesityl oxide from each other, so as to solve the problem that diacetone alcohol and mesityl oxide cannot be prepared from each other.

[0005] To achieve the above object, the present invention provides the following technical solutions:

[0006] A method for preparing diacetone alcohol and mesityl oxide from each other, wherein the raw material liquid comprises acetone, mesityl oxide and diacetone alcohol;

[0007] The preparation concrete steps of mesityl oxide are as follows:

[0008] (1) preparing a raw material solution, wherein the proportion of mesityl oxide is less than 39%;

[0009] (2) adding a sulfonated resin catalyst and water into the raw material liquid, and catalyzing the raw material liquid with the sulfonated resin at a reaction temperature of 40-80° C., wherein the reaction equation for converting diacetone alcohol to mesityl oxide is: (CH 3 ) 2COHCH 2 COCH 3 → (CH 3 ) 2CCHCOCH 3 + H 2 O;

[0010] (3) After the reaction is completed, the sulfonated resin is separated and then distilled to obtain mesityl oxide;

[0011] The specific steps for preparing diacetone alcohol are as follows:

[0012] (1) preparing a raw material solution, wherein the proportion of diacetone alcohol is less than 29%;

[0013] (2) adding a sulfonated resin catalyst and water into the raw material liquid, and catalyzing the raw material liquid with the sulfonated resin at a reaction temperature of 40-80° C., wherein the reaction equation for converting mesityl oxide to diacetone alcohol is: (CH 3 ) 2 CCHCOCH 3 + H 2 O → (CH 3 ) 2 COHCH 2 COCH 3 ;

[0014] (3) After the reaction is completed, the sulfonated resin is separated and then distilled to obtain diacetone alcohol.

[0015] Preferably, the specific steps for preparing diacetone alcohol are as follows:

[0016] (1) preparing a raw material solution, wherein the proportion of diacetone alcohol is less than 51%;

[0017] (2) adding a sulfonated resin catalyst and water into the raw material liquid, and using the sulfonated resin to catalyze the raw material liquid at a reaction temperature of 25-30° C.;

[0018] (3) After the reaction is completed, the sulfonated resin is separated and then distilled to obtain diacetone alcohol.

[0019] Preferably, the catalyst is hydrochloric acid and is in solid form.

[0020] Preferably, the catalyst is p-toluenesulfonic acid and is in solid form.

[0021] Preferably, the catalyst is sulfuric acid and is in solid form.

[0022] Compared with the prior art, the present invention has the following beneficial effects:

[0023] Sulfuric acid, hydrochloric acid, p-toluenesulfonic acid and sulfonated resin can be used as catalysts for preparing mesityl oxide from diacetone alcohol, or as catalysts for preparing diacetone alcohol from mesityl oxide. Diacetone alcohol can be used to prepare mesityl oxide, or mesityl oxide can be used to prepare diacetone alcohol. According to market demand, diacetone alcohol can be selected to prepare mesityl oxide, or mesityl oxide can be selected to prepare diacetone alcohol. Adjusting the product production structure is beneficial to preventing product sedimentation. DETAILED DESCRIPTION

[0024] The following is a clear and complete description of the technical solutions in the embodiments of the present invention. Obviously, the embodiments described are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making any creative efforts are within the scope of protection of the present invention.

[0025] The present invention provides a technical solution: a method for preparing diacetone alcohol and mesityl oxide from each other.

[0026] The raw material liquid includes acetone, mesityl oxide, and diacetone alcohol;

[0027] The preparation concrete steps of mesityl oxide are as follows:

[0028] (1) preparing a raw material solution, wherein the proportion of mesityl oxide is less than 39%;

[0029] (2) adding a sulfonated resin catalyst and water into the raw material liquid, catalyzing the raw material liquid with the sulfonated resin, the reaction temperature is 40-80°C, and the final ratio of mesityl oxide to diacetone alcohol is 2:1, wherein the reaction equation for converting diacetone alcohol to mesityl oxide is: (CH3)2COHCH2COCH3→(CH3)2CCHCOCH3+H2O;

[0030] (3) After the reaction is completed, the sulfonated resin is separated and then distilled to obtain mesityl oxide;

[0031] If diacetone alcohol is used to prepare mesityl oxide, acetone and diacetone alcohol are the main raw materials in the raw material liquid. To increase the amount of mesityl oxide produced, increase the amount of acetone and diacetone alcohol added to the reaction equipment. The reaction temperature is 40-80°C. The final ratio of mesityl oxide to diacetone alcohol is approximately 2:1. That is, mesityl oxide will be produced during the reaction. When the ratio of mesityl oxide to diacetone alcohol is approximately 2:1, the produced acetone and diacetone alcohol can be further added to the reaction equipment to produce mesityl oxide.

[0032] The specific steps for preparing diacetone alcohol are as follows:

[0033] (1) preparing a raw material solution, wherein the proportion of diacetone alcohol is less than 29%;

[0034] (2) adding a sulfonated resin catalyst and water into the raw material liquid, catalyzing the raw material liquid with the sulfonated resin, the reaction temperature is 40-80°C, and the final ratio of mesityl oxide to diacetone alcohol is 2:1, wherein the reaction equation for converting mesityl oxide to diacetone alcohol is: (CH3)2CCHCOCH3+H2O→(CH3)2COHCH2COCH3;

[0035] (3) After the reaction is completed, the sulfonated resin is separated and then distilled to obtain diacetone alcohol.

[0036] If diacetone alcohol is to be prepared from mesityl oxide, mesityl oxide is the main raw material in the raw material liquid. To increase the production of diacetone alcohol, increase the amount of mesityl oxide added to the reaction equipment. The reaction temperature is 40-80°C. The final ratio of mesityl oxide to diacetone alcohol is approximately 2:1. That is, diacetone alcohol will be produced during the reaction. When the ratio of mesityl oxide to diacetone alcohol is approximately 2:1, the produced mesityl oxide can be further added to the reaction equipment to produce diacetone alcohol.

[0037] Furthermore, the specific steps for preparing diacetone alcohol are as follows:

[0038] (1) preparing a raw material solution, wherein the proportion of diacetone alcohol is less than 51%;

[0039] (2) adding a sulfonated resin catalyst and water into the raw material liquid, catalyzing the raw material liquid with the sulfonated resin, the reaction temperature is 25-30° C., and the final ratio of mesityl oxide to diacetone alcohol is 4:5;

[0040] (3) After the reaction is completed, the sulfonated resin is separated and then distilled to obtain diacetone alcohol.

[0041] Through experiments, it was found that the reaction process of synthesizing diacetone alcohol from mesityl oxide is the same as that of synthesizing diacetone alcohol from diacetone alcohol. That is, when the reaction temperature is lowered, mesityl oxide is converted into diacetone alcohol, but the reaction is slower at low temperatures.

[0042] When preparing diacetone alcohol from mesityl oxide, when the reaction system is at room temperature, i.e., the reaction temperature is 25-30°C, and the reaction is carried out for a long time, the final ratio of mesityl oxide to diacetone alcohol is approximately 4:5, and the amount of diacetone alcohol converted into acetone is low, which can increase the amount of diacetone alcohol obtained after the final reaction.

[0043] Furthermore, the catalyst is hydrochloric acid and is in solid form.

[0044] Furthermore, the catalyst is p-toluenesulfonic acid and is in solid form.

[0045] Furthermore, the catalyst is sulfuric acid and is in solid form.

[0046] Sulfuric acid, hydrochloric acid, p-toluenesulfonic acid, and sulfonated resin can be used as catalysts for the preparation of mesityl oxide from diacetone alcohol, and vice versa. In the same reaction system, if one product is to be prepared, the proportion of the other product can be increased in the raw material liquid, which is conducive to adjusting the product production structure according to market needs.

[0047] Among them, catalysts in solid form are easy to separate and are more suitable as reaction catalysts. At the end of the reaction, separation and then distillation processes can be adopted to obtain the target product quickly and easily.

[0048] The specific plan is:

[0049] 1. Preparation of mesityl oxide:

[0050] The raw material liquid composition: acetone 35%, mesityl oxide 0.5%, diacetone alcohol 63%, others 1.5%; the reaction liquid composition: raw material liquid 100ml, sulfonated resin (wet product) about 30ml, water 20ml.

[0051] Reaction process: The raw materials react at 60-65℃ for 5 hours under the catalysis of sulfonated resin;

[0052] Sampling analysis: acetone 38%, mesityl oxide 39%, diacetone alcohol 21.5%, other impurities 1.5%.

[0053] 2. Preparation of diacetone alcohol:

[0054] The raw material liquid composition is: acetone 2.8%, mesityl oxide 91.5%, diacetone alcohol 2.2%, and other 3.5%. The reaction liquid composition is: raw material liquid 100ml, sulfonated resin (wet product) about 30ml, water 20ml.

[0055] Reaction process: The raw materials react at 60-65℃ for 5 hours under the catalysis of sulfonated resin;

[0056] Sampling analysis: acetone 8%, mesityl oxide 62.2%, diacetone alcohol 26.3%, other impurities 3.5%.

[0057] 3. Preparation of diacetone alcohol:

[0058] The raw material liquid composition is: acetone 2.8%, mesityl oxide 91.5%, diacetone alcohol 2.2%, and other 3.5%. The reaction liquid composition is: raw material liquid 240ml, sulfonated resin (wet product) about 100ml, water 50ml.

[0059] Reaction process: The raw materials react at 25-30℃ under the catalysis of sulfonated resin.

[0060] Sampling analysis after 72 hours: acetone 2.9%, mesityl oxide 71.5%, diacetone alcohol 22.6%, other impurities 3.1%.

[0061] Sampling analysis after 96 hours: acetone 3.1%, mesityl oxide 67.7%, diacetone alcohol 26.8%, other impurities 2.4%.

[0062] Sampling analysis after 120 hours: acetone 3.4%, mesityl oxide 64%, diacetone alcohol 30.5%, other impurities 2.1%.

[0063] Sampling analysis after 176 hours: acetone 4.5%, mesityl oxide 48.6%, diacetone alcohol 44.8%, other impurities 2.1%.

[0064] Sampling analysis after 216 hours: acetone 5.5%, mesityl oxide 41.5%, diacetone alcohol 51.6%, other impurities 1.4%.

[0065] 4. Preparation of diacetone alcohol:

[0066] The raw material liquid composition is: acetone 2.8%, mesityl oxide 91.5%, diacetone alcohol 2.2%, and other 3.5%. The reaction liquid composition is: raw material liquid 100ml, p-toluenesulfonic acid 2g, water 20ml.

[0067] Reaction process: The raw materials react at 25-30°C for 40 hours under the catalysis of p-toluenesulfonic acid;

[0068] Sampling analysis: acetone 3.5%, mesityl oxide 86.2%, diacetone alcohol 8.1%, others 2.2%;

[0069] Continue to heat to 55°C and react for 40 hours;

[0070] Sampling analysis: acetone 6.28%, mesityl oxide 64.6%, diacetone alcohol 27.2%.

[0071] 5. Preparation of diacetone alcohol:

[0072] The raw material liquid composition is: acetone 2.8%, mesityl oxide 91.5%, diacetone alcohol 2.2%, and other 3.5%. The reaction liquid composition is: raw material liquid 100ml, sulfuric acid 2g, water 20ml.

[0073] Reaction process: The raw materials react at 25-30℃ for 120 hours under the catalysis of sulfuric acid;

[0074] Sampling analysis: acetone 5.6%, mesityl oxide 66.5%, diacetone alcohol 25.9%, others 2%.

[0075] 6. Preparation of diacetone alcohol:

[0076] The raw material liquid composition is: acetone 2.8%, mesityl oxide 91.5%, diacetone alcohol 2.2%, and other 3.5%. The reaction liquid composition is: raw material liquid 100ml, hydrochloric acid 2g, water 20ml.

[0077] Reaction process: The raw materials react at 25-30℃ for 120 hours under the catalysis of hydrochloric acid;

[0078] Sampling analysis: acetone 5.4%, mesityl oxide 63.4%, diacetone alcohol 29.4%, others 1.8%.

[0079] While embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that various changes, modifications, substitutions, and variations may be made to these embodiments without departing from the principles and spirit of the invention, and that the scope of the invention is defined by the appended claims and their equivalents.

Claims

1. A method for preparing diacetone alcohol and mesityl oxide from each other, characterized in that: The raw material liquid includes acetone, mesityl oxide, and diacetone alcohol; The preparation concrete steps of mesityl oxide are as follows: (1) preparing a raw material solution in which mesityl oxide accounts for less than 39%; (2) Adding sulfonated resin catalyst and water into the raw material liquid, using the sulfonated resin to catalyze the raw material liquid, the reaction temperature is 40-80 ° C, wherein the reaction equation of diacetone alcohol to mesityl oxide is: (CH3)2COHCH2COCH3→(CH3)2CCHCOCH3+H2O; (3) After the reaction is completed, the sulfonated resin is separated and then distilled to obtain mesityl oxide; The specific steps for preparing diacetone alcohol are as follows: (1) preparing a raw material solution in which diacetone alcohol accounts for less than 29%; (2) Adding sulfonated resin catalyst and water into the raw material liquid, using the sulfonated resin to catalyze the raw material liquid, the reaction temperature is 40-80 ° C, wherein the reaction equation of isopropylamine oxide to diacetone alcohol is: (CH3)2CCHCOCH3+H2O→(CH3)2COHCH2COCH3; (3) After the reaction is completed, the sulfonated resin is first separated and then distilled to obtain diacetone alcohol.

2. The method for preparing diacetone alcohol and mesityl oxide according to claim 1, wherein: The specific steps for preparing diacetone alcohol are as follows: (1) preparing a raw material solution in which diacetone alcohol accounts for less than 51%; (2) Add sulfonated resin catalyst and water into the raw material liquid, and use the sulfonated resin to catalyze the raw material liquid. The reaction temperature is 25-30°C; (3) After the reaction is completed, the sulfonated resin is first separated and then distilled to obtain diacetone alcohol.