CN113443983B - Production method of dimethyl sebacate - Google Patents
Production method of dimethyl sebacate Download PDFInfo
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- CN113443983B CN113443983B CN202110870322.1A CN202110870322A CN113443983B CN 113443983 B CN113443983 B CN 113443983B CN 202110870322 A CN202110870322 A CN 202110870322A CN 113443983 B CN113443983 B CN 113443983B
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
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- C07C67/00—Preparation of carboxylic acid esters
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Abstract
The invention discloses a method for producing dimethyl sebacate, which adopts a solid acid catalyst to catalyze esterification of sebacic acid and methanol to produce the dimethyl sebacate, and comprises the specific operation processes of melting of sebacic acid, primary esterification kettle reaction and fixed bed final stage reaction, wherein the primary esterification kettle reaction adopts a method of methanol fed-batch coupled vaporization dehydration, the reaction is carried out at a temperature slightly higher than the melting point of sebacic acid, more than 95 percent of sebacic acid is converted into methyl sebacate, the fixed bed final stage reaction is carried out at a temperature lower than the boiling point of methanol, a small amount of residual carboxylic acid in a primary reaction product is subjected to refined reaction, the esterification rate is improved, the acid value of the product is reduced, and the purity of the product is improved. The invention has the advantages of short reaction time, high esterification rate, high product purity, easy separation of the catalyst, long service life, less methanol consumption and low energy consumption.
Description
Technical Field
The invention belongs to an acid catalytic esterification method of fatty acid, and particularly relates to a production method of dimethyl sebacate.
Background
Dimethyl sebacate is an organic chemical product with wide application, and is often used for preparing surfactants, leather additives, textile auxiliaries and the like. The main method for preparing dimethyl sebacate at present is to esterify sebacic acid and methanol under the catalysis of acid. The acid catalyst mainly comprises homogeneous catalysts such as sulfuric acid, p-toluenesulfonic acid and the like and solid acid catalysts. CN1070395A discloses a production method of concentrated sulfuric acid as a catalyst. Adding sebacic acid and methanol into a stirring kettle according to a certain proportion, adding a certain amount of concentrated sulfuric acid, and separating out a water phase after the sebacic acid is completely dissolved and the temperature is reduced to a solution to form an interface; continuously adding methanol and sebacic acid, performing second-step esterification, dealcoholizing, and separating a water phase; and then methanol and sebacic acid are supplemented, and the third step of esterification is carried out. Then water washing, neutralization, water washing and reduced pressure distillation are carried out to remove water, and the dimethyl sebacate is prepared. The method has complex steps, and the concentrated sulfuric acid is used as a catalyst, so that equipment is easy to corrode, the concentrated sulfuric acid is difficult to recover, and a large amount of acidic wastewater is generated to pollute the environment. In the processes of washing deacidification and distillation dehydration, the product is easy to return acid and the color is deepened. CN102351692A discloses a production method using solid acid as catalyst. Adding sebacic acid, methanol and a solid acid catalyst into an esterification kettle according to a certain proportion, stirring and heating, carrying out two-stage esterification, wherein the first-stage esterification temperature is 70-85 ℃, the esterification time is 3-4 h, after the first-stage esterification is finished, removing alcohol and water in reactants by evaporation at 90 ℃, and then carrying out two-stage esterification at 110-140 ℃. And neutralizing and rectifying the crude product obtained after the secondary esterification by using a sodium carbonate solution to obtain a dimethyl sebacate product. The solid acid catalyst is adopted to solve the problem that sulfuric acid is used as the catalyst, but the reaction is carried out in a kettle type stirring reactor, the temperature of the first-stage esterification is between the boiling points of methanol and water, so that the added methanol is partially vaporized, the heat energy is consumed, the methanol concentration in a reaction system is reduced, and in addition, the water generated by esterification is not easy to evaporate, so that the method is limited by a reversible reaction, the esterification rate is slow, the esterification time is long, and the esterification rate is low. The second-stage esterification temperature is higher than the boiling point of water, which is beneficial to the removal of water, but can cause a large amount of methanol to be distilled off, the amount of methanol remained in a reaction system is little, which is not beneficial to the second-stage esterification reaction, and the product still has higher acid value and needs to be refined by rectification, thereby further increasing the energy consumption and the equipment investment.
Disclosure of Invention
In order to solve the problems, the invention aims to provide a method for producing dimethyl sebacate.
In order to achieve the purpose, the following technical scheme is provided:
a production method of dimethyl sebacate specifically comprises the following steps:
1) melting sebacic acid: adding solid sebacic acid into a melting kettle, and heating until the sebacic acid is completely melted;
2) primary esterification kettle reaction: pumping the molten liquid sebacic acid into a primary esterification kettle filled with a solid acid catalyst by using a sebacic acid feed pump, heating to a reaction temperature, adding liquid methanol flow into the primary esterification kettle by using a methanol feed pump, stirring for reacting for a period of time until the acid value of a primary reactant is less than 20mgKOH/g, pumping the primary reactant into a dosing tank by using a first infusion pump, and rectifying an alcohol-water mixture distilled from the top of the primary esterification kettle to recover methanol;
3) fixed bed final stage reaction: pumping liquid methanol into a dosing tank with a primary reactant according to a certain alcohol acid ratio by using a methanol feeding pump, stirring and mixing, pumping the mixed solution into a fixed bed reactor filled with a solid acid catalyst by using a second liquid conveying pump, so that the primary reaction product and the methanol are subjected to esterification reaction in the fixed bed reactor, controlling the retention time of materials in the fixed bed reactor by adjusting the flow rate of the mixed solution so as to ensure that the primary reaction product and the methanol are retained in the fixed bed reactor for enough time, so that the acid value of the product flowing out of the fixed bed reactor meets the product requirement, removing a small amount of methanol and water in the product flowing out of the fixed bed reactor by using an evaporation kettle to obtain a dimethyl sebacate product, and conveying the dimethyl sebacate product to a product storage tank.
Further, the temperature of the melting kettle in the step 1) is 130-150 ℃.
Further, the solid acid catalyst is strong acidic ion exchange resin or sulfonated carbon.
Further, the reaction temperature of the primary esterification kettle is 130-150 ℃, the dosage of the solid acid catalyst put into the primary esterification kettle is 1-15 wt% of the dosage of the raw materials, the flow acceleration rate of methanol is 0.005-0.02 mL/(g sebacic acid & min), and the reaction time is 60-120 min.
Further, the reaction conditions in step 3) are: the mass ratio of the alcohol acid to the alcohol acid is 0.05-0.2: 1, the reaction temperature is 50-70 ℃, and the retention time is 10-60 min.
Further, the methanol used is liquid methanol at normal temperature.
Further, the fixed bed reactor is a tubular reactor, the inner diameter of a tubular reactor is 19-25 mm, the length of the tubular reactor is 20-150 cm, and a reaction material passes through a tube pass.
The invention has the beneficial effects that:
(1) the solid acid catalyst is adopted, so that the problems of equipment corrosion, catalyst recovery, deep product oxidation color, large amount of waste water, product acid return and the like caused by removing the catalyst by water washing and the like caused by homogeneous catalysts such as sulfuric acid, p-toluenesulfonic acid and the like are avoided.
(2) In the primary esterification reaction step of the primary esterification kettle, the reaction temperature is controlled to be slightly higher than the melting point of sebacic acid, so that the sebacic acid exists in a liquid state in a reaction system, and the contact, mixing and reaction between the sebacic acid and methanol are facilitated; the melting point of the sebacic acid is higher than 130 ℃, and the water generated by esterification is vaporized and removed at the reaction temperature, so that the esterification reaction is favorably carried out in the direction of generating dimethyl sebacate; although the reaction temperature is higher than the boiling point of the methanol, because the acid value of the reaction system is higher and the carboxyl quantity is more in the primary esterification step, the methanol entering the reaction system can fully contact the carboxyl to generate esterification reaction before vaporization, and simultaneously, the vaporization quantity of the methanol is reduced and the utilization rate of the methanol is improved by feeding the methanol.
(3) The acid value of the material after primary esterification is reduced, the amount of carboxyl in the system is reduced, if high-temperature reaction is continuously adopted, the collision probability of methanol and the carboxyl before vaporization is reduced, and the utilization rate of the methanol is reduced. And a tubular reactor assembled by a plurality of small-inner-diameter reaction tubes in parallel is adopted, so that the temperature distribution, the concentration distribution and the residence time distribution of the materials in the reaction tubes are more uniform.
(4) The two-stage reaction of the stirred tank and the fixed bed connected in series is adopted, and most sebacic acid is esterified in the stirred tank, generated water is removed through vaporization, a primary product entering the fixed bed is low in acid value, and less water is generated in the fixed bed reactor, so that the water absorption capacity of solid acid is reduced, the service life of the solid acid catalyst in the fixed bed is prolonged, and the operation time of the fixed bed reactor is prolonged.
Drawings
FIG. 1 is a flow chart of the production process of the present invention;
in the figure: 1. a melting kettle; 2. a sebacic acid feed pump; 3. a primary esterification kettle; 4. a first infusion pump; 5. a dosing tank; 6. a fixed bed reactor; 7. a second infusion pump; 8. evaporating the kettle; 9. a product storage tank; 10. a methanol feed pump.
Detailed Description
The invention will be further illustrated with reference to specific examples, without restricting its scope.
Example 1
1) Firstly, putting solid sebacic acid into a melting kettle 1, introducing heating steam into a jacket of the melting kettle to heat, and heating to 140 ℃ to completely melt the solid sebacic acid; the melting time is 60min, and the acid value of the product is 554.5 mgKOH/g;
2) the melted sebacic acid is pumped into a primary esterification kettle 3 from the lower part of a melting kettle 1 through a sebacic acid feeding pump 2, strong acid ion exchange resin is added, the dosage of the strong acid ion exchange resin is 12.5wt% of the mass of the raw materials, a methanol feeding pump 10 is used for feeding liquid methanol into the primary esterification kettle 3, the sebacic acid and the methanol are subjected to primary esterification reaction, the feeding speed of the methanol is 0.007 mL/(g sebacic acid & min), the reaction is carried out for 120min at the temperature of 140 ℃, the acid value of the primary esterified product is 15.2g mgKOH/g, and the esterification rate is 97.3%;
3) pumping the primary esterified substance into a dosing tank 5 from a discharge pipe at the lower part of a primary esterification kettle 3 by using a first liquid conveying pump 4, wherein a filter screen is arranged at the end of the discharge pipe close to the primary esterification kettle 3 to filter strong-acid ion exchange resin, and part of methanol steam and water generated in the esterification reaction process are conveyed to a methanol recovery tower through a riser at the top of the primary esterification kettle 3 to carry out methanol recovery;
4) pumping normal-temperature liquid methanol into a batching tank 5 by using a methanol feed pump 10, wherein the using amount of the methanol is 0.07 g/g of primary esterified substance, starting stirring to uniformly mix the methanol and the primary esterified substance, pumping the mixture into a fixed bed reactor 6 by using a second infusion pump 7, wherein the fixed bed reactor 6 is a tubular reactor, the number of the tubular reactors is 1, the inner diameter of the tubular reactors is 19mm, the height of a strong-acid ion exchange resin bed is 50cm, the reaction temperature is 60 ℃, controlling the flow rate, so that the retention time of the material in the fixed bed reactor 6 is 18min, and the material coming out of the top end of the fixed bed reactor 6 is a crude product of dimethyl sebacate;
5) and overflowing the crude dimethyl sebacate product obtained after two-stage esterification into an evaporation kettle 8, removing methanol and a small amount of water in the evaporation kettle 8 to obtain a dimethyl sebacate product, and storing the dimethyl sebacate product in a product storage tank 9, wherein the acid value of the product is 3.08 mgKOH/g, and the product yield is 99.5%.
Example 2
1) Firstly, putting solid sebacic acid into a melting kettle 1, introducing heating steam into a jacket of the melting kettle to heat, and heating to 130 ℃ to completely melt the solid sebacic acid; the melting time is 70min, and the acid value of the product is 554.5 mgKOH/g;
2) pumping the melted sebacic acid into a primary esterification kettle 3 from the lower part of a melting kettle 1 through a sebacic acid feeding pump 2, adding sulfonated carbon, wherein the dosage of the sulfonated carbon is 3wt% of the mass of the raw materials, feeding liquid methanol into the primary esterification kettle 3 through a methanol feeding pump 10, and carrying out primary esterification reaction on the sebacic acid and the methanol, wherein the feeding speed of the methanol is 0.02 mL/(g sebacic acid & min), the reaction is carried out for 60min at the temperature of 150 ℃, and the acid value of the primary esterified substance is measured to be 18.1 mgKOH/g, and the esterification rate is 96.7%;
3) pumping the primary esterified substance into a dosing tank 5 from a discharge pipe at the lower part of a primary esterification kettle 3 by using a first liquid conveying pump 4, wherein a filter screen is arranged at the end of the discharge pipe close to the primary esterification kettle 3 to filter strong-acid ion exchange resin, and part of methanol steam and water generated in the esterification reaction process are conveyed to a methanol recovery tower through a riser at the top of the primary esterification kettle 3 to carry out methanol recovery;
4) pumping normal-temperature liquid methanol into a batching tank 5 by using a methanol feed pump 10, wherein the using amount of the methanol is 0.15 g/g of primary esterified substance, starting stirring to uniformly mix the methanol and the primary esterified substance, pumping the mixture into a fixed bed reactor 6 by using a second infusion pump 7, wherein the fixed bed reactor 6 is a tubular reactor, the number of the tubular reactors is 1, the inner diameter of the tubular reactors is 19mm, the height of a strong-acid ion exchange resin bed is 50cm, the reaction temperature is 55 ℃, controlling the flow rate, so that the retention time of the material in the fixed bed reactor 6 is 55min, and the material coming out of the top end of the fixed bed reactor 6 is a crude product of dimethyl sebacate;
5) and overflowing the crude dimethyl sebacate product obtained after two-stage esterification into an evaporation kettle 8, removing methanol and a small amount of water in the evaporation kettle 8 to obtain a dimethyl sebacate product, and storing the dimethyl sebacate product in a product storage tank 9, wherein the acid value of the product is 3.41mgKOH/g, and the product yield is 99.4%.
Example 3
1) Firstly, putting solid sebacic acid into a melting kettle 1, introducing heating steam into a jacket of the melting kettle to heat, and heating to 150 ℃ to completely melt the solid sebacic acid; the melting time is 50min, and the acid value of the product is 554.5 mgKOH/g;
2) the melted sebacic acid is pumped into a primary esterification kettle 3 from the lower part of a melting kettle 1 through a sebacic acid feeding pump 2, strong acid ion exchange resin is added, the dosage of the strong acid ion exchange resin is 6.25wt% of the mass of the raw materials, a methanol feeding pump 10 is used for feeding liquid methanol into the primary esterification kettle 3, so that the sebacic acid and the methanol are subjected to primary esterification reaction, the feeding speed of the methanol is 0.015 mL/(g sebacic acid. min), the reaction is carried out for 100min at the temperature of 130 ℃, the acid value of the primary esterified product is measured to be 17.4g mgKOH/g, and the esterification rate is 96.8%;
3) pumping the primary esterified substance into a dosing tank 5 from a discharge pipe at the lower part of a primary esterification kettle 3 by using a first liquid conveying pump 4, wherein a filter screen is arranged at the end of the discharge pipe close to the primary esterification kettle 3 to filter strong-acid ion exchange resin, and part of methanol steam and water generated in the esterification reaction process are conveyed to a methanol recovery tower through a riser at the top of the primary esterification kettle 3 to carry out methanol recovery;
4) pumping normal-temperature liquid methanol into a batching tank 5 by using a methanol feed pump 10, wherein the using amount of the methanol is 0.07 g/g of primary esterified substance, starting stirring to uniformly mix the methanol and the primary esterified substance, pumping the mixture into a fixed bed reactor 6 by using a second infusion pump 7, wherein the fixed bed reactor 6 is a tubular reactor, the number of the tubular reactors is 1, the inner diameter of the tubular reactors is 19mm, the height of a strong-acid ion exchange resin bed is 50cm, the reaction temperature is 65 ℃, controlling the flow rate, so that the retention time of the material in the fixed bed reactor 6 is 35min, and the material coming out of the top end of the fixed bed reactor 6 is a crude product of dimethyl sebacate;
5) and overflowing the crude dimethyl sebacate product obtained after two-stage esterification into an evaporation kettle 8, removing methanol and a small amount of water in the evaporation kettle 8 to obtain a dimethyl sebacate product, and storing the dimethyl sebacate product in a product storage tank 9, wherein the acid value of the product is 4.23 mgKOH/g, and the product yield is 99.3%.
Claims (5)
1. The production method of dimethyl sebacate is characterized by comprising the following steps:
1) melting sebacic acid: adding solid sebacic acid into a melting kettle (1), and heating until the sebacic acid is completely melted;
2) primary esterification kettle (3) reaction: pumping the molten liquid sebacic acid into a primary esterification kettle (3) filled with a solid acid catalyst by using a sebacic acid feed pump (2), heating to a reaction temperature, adding a liquid methanol flow into the primary esterification kettle (3) by using a methanol feed pump (10), stirring for reacting for a period of time until the acid value of a primary reactant is less than 20mgKOH/g, pumping the primary reactant into a dosing tank (5) by using a first infusion pump (4), and rectifying an alcohol-water mixture distilled from the top of the primary esterification kettle (3) to recover methanol;
3) fixed bed final stage reaction: pumping liquid methanol into a dosing tank (5) added with a primary reactant according to a certain alcohol acid ratio by using a methanol feeding pump (10), stirring and mixing, pumping a mixed solution into a fixed bed reactor (6) filled with a solid acid catalyst by using a second infusion pump (7), enabling a primary reaction product and the methanol to have an esterification reaction in the fixed bed reactor (6), controlling the retention time of the material in the fixed bed reactor (6) by adjusting the flow rate of the mixed solution, so as to ensure that the primary reaction product and the methanol are retained in the fixed bed reactor (6) for a sufficient time, enabling the acid value of a product flowing out of the fixed bed reactor (6) to meet the product requirement, removing a small amount of methanol and water in the product flowing out of the fixed bed reactor (6) through an evaporation kettle (8), obtaining a dimethyl sebacate product, and conveying the dimethyl sebacate product to a product storage tank (9);
the reaction temperature of the primary esterification kettle (3) is 130-150 ℃, the dosage of the solid acid catalyst put into the primary esterification kettle (3) is 1-15 wt% of the dosage of the raw materials, the flow acceleration rate of methanol is 0.005-0.02 mL/(g sebacic acid-min), and the reaction time is 60-120 min;
the reaction conditions in step 3) are as follows: the mass ratio of the alcohol acid to the alcohol acid is 0.05-0.2: 1, the reaction temperature is 50-70 ℃, and the retention time is 10-60 min.
2. The method for producing dimethyl sebacate according to claim 1, wherein the temperature of the melting kettle (1) in step 1) is 130-150 ℃.
3. The method of claim 1, wherein the solid acid catalyst is a strongly acidic ion exchange resin or sulfonated carbon.
4. The method of claim 1, wherein the methanol used is liquid methanol at ambient temperature.
5. The method for producing the dimethyl sebacate according to claim 1, wherein the fixed bed reactor (6) is a tubular reactor, the inner diameter of the tubular reactor is 19-25 mm, the length of the tubular reactor is 20-150 cm, and the reaction materials pass through the tubular reactor.
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2021
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| JPS552708A (en) * | 1978-06-19 | 1980-01-10 | Asahi Chem Ind Co Ltd | Preparation of sebacic acid diester |
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