CN108993509B - Catalyst for improving synthesis conversion rate of dioctyl phthalate plasticizer - Google Patents

Catalyst for improving synthesis conversion rate of dioctyl phthalate plasticizer Download PDF

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CN108993509B
CN108993509B CN201810919768.7A CN201810919768A CN108993509B CN 108993509 B CN108993509 B CN 108993509B CN 201810919768 A CN201810919768 A CN 201810919768A CN 108993509 B CN108993509 B CN 108993509B
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dioctyl phthalate
catalyst
conversion rate
phthalate plasticizer
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CN108993509A (en
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纪安全
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Guangdong Yuancheng Chemical Co ltd
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Suzhou Qingguo Intellectual Property Service Co Ltd
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—Iron group metals
    • B01J23/75—Cobalt
    • B01J35/40—
    • B01J35/61—
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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

Abstract

The invention relates to the technical field of novel functional materials, and discloses a catalyst for improving the synthetic conversion rate of dioctyl phthalate plasticizer, which takes cobalt chloride hexahydrate and ferroferric oxide magnetic powder as main raw materials, utilizes a cobalt oxide nano composite material obtained by coating magnetic iron oxide, has strong catalytic activation performance, rich pore channels, large specific surface area and less dosage, can catalyze more reaction groups, ensures that the conversion rate of dioctyl phthalate reaches more than 99.8 percent, has high plasticizing efficiency of the synthesized plasticizer, and obviously reduces the cost due to the magnetism and high recovery utilization rate of the plasticizer, solves the problem of low conversion rate of the existing dioctyl phthalate plasticizer in the synthetic reaction, can realize the reduction of the production cost of the dioctyl phthalate plasticizer and expand the practical significance of the application field of metal catalysts, is a technical scheme which is very worthy of popularization and application.

Description

Catalyst for improving synthesis conversion rate of dioctyl phthalate plasticizer
Technical Field
The invention belongs to the technical field of novel functional materials, and particularly relates to a catalyst for improving the synthesis conversion rate of dioctyl phthalate plasticizer.
Background
Plastics are high molecular compounds, commonly called plastics or resins, which are made from monomers by polyaddition or polycondensation, can freely change the components and shape and form, and are composed of synthetic resins and additives such as fillers, plasticizers, stabilizers, lubricants, pigments, etc. Among them, plasticizers are generally also called plasticizers. The plasticizer is a polymer material assistant widely used in industry, and the flexibility of the plasticizer can be enhanced by adding the plasticizer in plastic processing, the plasticizer is easy to process, and the plasticizer can be legally used for industrial application.
Plasticizers are classified into aliphatic dibasic acid esters, phthalic acid esters (including phthalic acid esters and terephthalic acid esters), benzene polycarboxylic acid esters, benzoic acid esters, polyol esters, chlorinated hydrocarbons, epoxies, citric acid esters, polyesters and the like. There are many more than one plasticizer product, but the most commonly used is a group of compounds known as phthalates (or phthalates, also known as phthalates).
Among phthalate esters, dioctyl phthalate is the most productive and comprehensive variety, and has good compatibility with most polymers, high plasticizing efficiency and low volatilization.
At present, phthalic anhydride and 2-ethylhexanol are adopted for synthesis production of dioctyl phthalate through two-step esterification reaction, wherein the monoester reaction is fast, the diester reaction synthesized from the monoester is very slow, acid is widely used as a catalyst at present, and the problems of high three-waste amount, side reaction, low conversion rate and poor product quality exist, and other non-acidic catalysts still have poor pertinence and low reaction conversion rate, so that the synthesis raw materials are expensive and waste is large.
Disclosure of Invention
The invention aims to provide a catalyst for improving the synthetic conversion rate of dioctyl phthalate plasticizer, aiming at the existing problems, so that the conversion rate of dioctyl phthalate reaches more than 99.8%, and the catalyst has high recovery rate and remarkably reduces the cost due to the magnetism.
The invention is realized by the following technical scheme:
a catalyst for improving the synthetic conversion rate of dioctyl phthalate plasticizer is prepared by the following steps:
(1) weighing 9.5-9.8 g of cobalt chloride hexahydrate and 0.5-0.6 g of ethylenediamine tetraacetic acid, adding the cobalt chloride hexahydrate and the ethylenediamine tetraacetic acid into a beaker, adding 70-80 ml of sodium hydroxide solution into the beaker, magnetically stirring for 15-20 minutes, then adding 1.8-2.0 g of ferroferric oxide magnetic powder and 1.0-1.2 g of sodium borate into the beaker, stirring and mixing for 25-35 minutes under the heating of a water bath at 55-60 ℃, then pouring the stirred mixture into a three-neck flask, introducing nitrogen, dropwise adding 4.0-4.5 ml of polyethylene glycol, heating to 75-85 ℃, adjusting the pH value of the system to be 9.4-9.7 by using a boric acid solution, and stirring and reacting for 50-60 minutes;
(2) after the reaction is finished, cooling to 35-40 ℃, sequentially using acetone and ethanol to respectively perform ultrasonic cleaning, heating and evaporating the obtained filtrate at the temperature of 100-105 ℃, separating a solid product, using deionized water and hexane to respectively clean for 2-3 times, then drying for 2-3 hours at the temperature of 55-60 ℃ in vacuum to obtain a dried product, dispersing the dried product in ethylenediamine and deionized water, and performing ultrasonic dispersion for 15-20 minutes to obtain a mixture;
(3) transferring the mixture into a polytetrafluoroethylene-lined high-pressure reaction kettle, carrying out heat preservation reaction at the temperature of 160-165 ℃ for 14-16 hours under the pressure of 1.1-1.2MPa, naturally cooling to room temperature after the reaction is finished, taking out the product, sequentially cleaning for 4-5 times by using deionized water and absolute ethyl alcohol, drying the product at the temperature of 100-110 ℃ for 4-5 hours, placing the product into a crucible, calcining for 3-4 hours in a muffle furnace at the temperature of 470-490 ℃, cooling and grinding into powder.
As a further description of the scheme, the mass concentration of the sodium hydroxide solution in the step (1) is 8-10%.
As a further description of the above scheme, the pH value of the boric acid solution in the step (1) is between 4.0 and 4.2.
As a further description of the above scheme, the ultrasonic cleaning process of acetone and ethanol in step (2) is as follows: uniformly dispersing the product and the solvent according to the mass ratio of 1:3.0-3.2, then carrying out ultrasonic oscillation for 5-6 minutes in an ultrasonic cleaner, and filtering.
As a further description of the scheme, in the step (2), the dried substance is dispersed in the ethylenediamine and the deionized water, and the mass ratio of the ethylenediamine to the deionized water is 1:5.0-5.5: 7.2-7.4.
As a further description of the above scheme, the catalyst prepared in step (3) has a particle size of 50-80 nm.
Compared with the prior art, the invention has the following advantages: in order to solve the problem of low conversion rate of the existing dioctyl phthalate plasticizer in the synthesis reaction, the invention provides a catalyst for improving the synthesis conversion rate of the dioctyl phthalate plasticizer, a cobalt oxide nano composite material obtained by coating magnetic iron oxide has strong catalytic activation performance, rich pore channels, large specific surface area and less consumption, can catalyze more reaction groups, enables the conversion rate of the dioctyl phthalate to reach more than 99.8 percent, has high plasticizing efficiency of the synthesized plasticizer, has high recovery utilization rate due to the magnetism, and obviously reduces the cost, the catalyst prepared by the invention solves the problem of low conversion rate of the existing dioctyl phthalate plasticizer in the synthesis reaction, has higher recovery usability, considers the promotion of the catalytic effect and the service life, and improves the development and utilization of metal catalysts, can realize the practical significance of reducing the production cost of the phthalate plasticizer and expanding the application field of the metal catalyst, and is a technical scheme which is very worthy of popularization and application.
Detailed Description
In order to make the objects, technical solutions and effects of the present invention clearer and clearer, the present invention is further described with reference to specific embodiments, and it should be understood that the specific embodiments described herein are only used for explaining the present invention and are not used for limiting the technical solutions provided by the present invention.
Example 1
A catalyst for improving the synthetic conversion rate of dioctyl phthalate plasticizer is prepared by the following steps:
(1) weighing 9.5 g of cobalt chloride hexahydrate and 0.5 g of ethylenediamine tetraacetic acid, adding the cobalt chloride hexahydrate and the ethylenediamine tetraacetic acid into a beaker, adding 70 ml of a sodium hydroxide solution into the beaker, magnetically stirring for 15 minutes, then adding 1.8 g of ferroferric oxide magnetic powder and 1.0 g of sodium borate into the beaker, stirring and mixing for 25 minutes under the heating of a water bath at 55 ℃, then pouring the stirred mixture into a three-neck flask, introducing nitrogen, dropwise adding 4.0 ml of polyethylene glycol, heating to 75 ℃, adjusting the pH value of the system to 9.4-9.7 by using a boric acid solution, and stirring and reacting for 50 minutes;
(2) after the reaction is finished, cooling to 35 ℃, sequentially using acetone and ethanol to respectively perform ultrasonic cleaning, heating and evaporating the obtained filtrate at 100 ℃, separating a solid product, using deionized water and hexane to respectively clean for 2 times, then drying for 2 hours at 55 ℃ in vacuum to obtain a dried product, dispersing the dried product in ethylenediamine and deionized water, and performing ultrasonic dispersion for 15 minutes to obtain a mixture;
(3) and transferring the mixture into a high-pressure reaction kettle with a polytetrafluoroethylene lining, carrying out heat preservation reaction at 160 ℃ for 14 hours under the pressure of 1.1MPa, naturally cooling to room temperature after the reaction is finished, taking out the product, sequentially washing for 4 times by using deionized water and absolute ethyl alcohol, drying the product at 100 ℃ for 4 hours, placing the product into a crucible, placing the crucible into a muffle furnace for calcining for 3 hours at the calcining temperature of 470 ℃, cooling and grinding into powder.
As a further description of the above scheme, the sodium hydroxide solution in step (1) has a mass concentration of 8%.
As a further description of the above scheme, the pH value of the boric acid solution in the step (1) is between 4.0 and 4.2.
As a further description of the above scheme, the ultrasonic cleaning process of acetone and ethanol in step (2) is as follows: uniformly dispersing the product and the solvent according to the mass ratio of 1:3.0, then carrying out ultrasonic oscillation for 5 minutes in an ultrasonic cleaner, and filtering.
As a further description of the above scheme, in the step (2), the dried substance is dispersed in the ethylenediamine and the deionized water in the mass ratio of 1:5.0: 7.2.
As a further description of the above scheme, the catalyst prepared in step (3) has a particle size of 50-80 nm.
Example 2
A catalyst for improving the synthetic conversion rate of dioctyl phthalate plasticizer is prepared by the following steps:
(1) weighing 9.6 g of cobalt chloride hexahydrate and 0.55 g of ethylenediamine tetraacetic acid, adding the cobalt chloride hexahydrate and the ethylenediamine tetraacetic acid into a beaker, adding 75 ml of a sodium hydroxide solution into the beaker, magnetically stirring for 18 minutes, then adding 1.9 g of ferroferric oxide magnetic powder and 1.1 g of sodium borate into the beaker, stirring and mixing for 30 minutes under the heating of a water bath at 58 ℃, then pouring the stirred mixture into a three-neck flask, introducing nitrogen, dropwise adding 4.2 ml of polyethylene glycol, heating to 80 ℃, adjusting the pH value of the system to 9.4-9.7 by using a boric acid solution, and stirring and reacting for 55 minutes;
(2) after the reaction is finished, cooling to 38 ℃, sequentially using acetone and ethanol to respectively perform ultrasonic cleaning, heating and evaporating the obtained filtrate at 103 ℃, separating a solid product, using deionized water and hexane to respectively clean for 2 times, then drying for 2.5 hours at 58 ℃ under vacuum to obtain a dried product, dispersing the dried product in ethylenediamine and deionized water, and performing ultrasonic dispersion for 18 minutes to obtain a mixture;
(3) transferring the mixture into a high-pressure reaction kettle with a polytetrafluoroethylene lining, carrying out heat preservation reaction at 162 ℃ for 15 hours under the pressure of 1.15MPa, naturally cooling to room temperature after the reaction is finished, taking out the product, sequentially washing for 4 times by using deionized water and absolute ethyl alcohol, drying the product at 105 ℃ for 4.5 hours, placing the product into a crucible, placing the crucible into a muffle furnace for calcining for 3.5 hours at 480 ℃, cooling and grinding into powder.
As a further description of the above scheme, the sodium hydroxide solution in step (1) has a mass concentration of 9%.
As a further description of the above scheme, the pH value of the boric acid solution in the step (1) is between 4.0 and 4.2.
As a further description of the above scheme, the ultrasonic cleaning process of acetone and ethanol in step (2) is as follows: uniformly dispersing the product and the solvent according to the mass ratio of 1:3.1, then carrying out ultrasonic oscillation for 5.5 minutes in an ultrasonic cleaner, and filtering.
As a further description of the scheme, in the step (2), the dried substance is dispersed in the ethylenediamine and the deionized water, and the mass ratio of the ethylenediamine to the deionized water is 1:5.3: 7.3.
As a further description of the above scheme, the catalyst prepared in step (3) has a particle size of 50-80 nm.
Example 3
A catalyst for improving the synthetic conversion rate of dioctyl phthalate plasticizer is prepared by the following steps:
(1) weighing 9.8 g of cobalt chloride hexahydrate and 0.6 g of ethylenediamine tetraacetic acid, adding the cobalt chloride hexahydrate and the ethylenediamine tetraacetic acid into a beaker, adding 80 ml of a sodium hydroxide solution into the beaker, magnetically stirring for 20 minutes, then adding 2.0 g of ferroferric oxide magnetic powder and 1.2 g of sodium borate into the beaker, stirring and mixing for 35 minutes under the heating of a water bath at 60 ℃, then pouring the stirred mixture into a three-neck flask, introducing nitrogen, dropwise adding 4.5 ml of polyethylene glycol, heating to 85 ℃, adjusting the pH value of the system to be 9.4-9.7 by using a boric acid solution, and stirring and reacting for 60 minutes;
(2) after the reaction is finished, cooling to 40 ℃, sequentially using acetone and ethanol to respectively perform ultrasonic cleaning, heating and evaporating the obtained filtrate at 105 ℃, separating a solid product, using deionized water and hexane to respectively clean for 3 times, then drying for 3 hours at 60 ℃ in vacuum to obtain a dried product, dispersing the dried product in ethylenediamine and deionized water, and performing ultrasonic dispersion for 20 minutes to obtain a mixture;
(3) transferring the mixture into a high-pressure reaction kettle with a polytetrafluoroethylene lining, carrying out heat preservation reaction at 165 ℃ for 16 hours under the pressure of 1.2MPa, naturally cooling to room temperature after the reaction is finished, taking out the product, sequentially washing for 5 times by using deionized water and absolute ethyl alcohol, drying the product at 110 ℃ for 5 hours, placing the product into a crucible, placing the crucible into a muffle furnace for calcination for 4 hours at the calcination temperature of 490 ℃, cooling and grinding into powder.
As a further description of the above scheme, the sodium hydroxide solution in step (1) has a mass concentration of 10%.
As a further description of the above scheme, the pH value of the boric acid solution in the step (1) is between 4.0 and 4.2.
As a further description of the above scheme, the ultrasonic cleaning process of acetone and ethanol in step (2) is as follows: uniformly dispersing the product and the solvent according to the mass ratio of 1:3.2, then carrying out ultrasonic oscillation in an ultrasonic cleaner for 6 minutes, and filtering.
As a further description of the scheme, in the step (2), the dried substance is dispersed in the ethylenediamine and the deionized water, and the mass ratio of the ethylenediamine to the deionized water is 1:5.5: 7.4.
As a further description of the above scheme, the catalyst prepared in step (3) has a particle size of 50-80 nm.
Comparative example 1
The only difference from example 1 is that in the preparation of the catalyst, the addition of ferroferric oxide magnetic powder and sodium borate in step (1) is omitted, and the rest is kept consistent.
Comparative example 2
The only difference from example 2 is that in the catalyst preparation, the reaction process of adding polyethylene glycol in step (1) is omitted and the rest is kept the same.
Comparative example 3
The only difference from example 3 is that in the preparation of the catalyst, the ultrasonic cleaning process using acetone and ethanol in sequence in step (2) was omitted, and the rest was kept the same.
Comparative example 4
The only difference from example 3 is that in the catalyst preparation, the reaction was maintained at 175 ℃ for 12 hours in step (3) at a pressure of 1.3MPa, the remainder being identical.
Comparative example 5
The only difference from example 3 is that in the catalyst preparation, the catalyst in step (3) was calcined in a muffle furnace for 5 hours at 440 ℃ and the rest was kept the same.
Comparative experiment
Catalysts for improving the synthetic conversion rate of dioctyl phthalate plasticizers are prepared by using the methods of examples 1-3 and comparative examples 1-5 respectively, a method for preparing dioctyl phthalate by using sulfuric acid with the mass concentration of 60% as a catalyst is used as a control group, raw materials of all the components are the same, dioctyl phthalate is processed and synthesized according to the methods of all the components, the conversion rate and the reaction speed of all the components are calculated, meanwhile, the performances of the synthesized plasticizers are compared, independent variables in the test are kept consistent, the performances of all the groups of prepared catalysts are evaluated, effective average values are counted, and the results are shown in the following table:
Figure 80074DEST_PATH_IMAGE002
the catalyst prepared by the invention solves the problem of low conversion rate of the existing dioctyl phthalate plasticizer in the synthesis reaction, has higher recycling performance, improves the catalytic effect and the service life, improves the development and utilization of the metal catalyst, can realize the practical significance of reducing the production cost of the phthalate plasticizer and expanding the application field of the metal catalyst, and is a technical scheme which is extremely worthy of popularization and application.

Claims (6)

1. The catalyst for improving the synthesis conversion rate of the dioctyl phthalate plasticizer is characterized in that the preparation method comprises the following steps:
(1) weighing 9.5-9.8 g of cobalt chloride hexahydrate and 0.5-0.6 g of ethylenediamine tetraacetic acid, adding the cobalt chloride hexahydrate and the ethylenediamine tetraacetic acid into a beaker, adding 70-80 ml of sodium hydroxide solution into the beaker, magnetically stirring for 15-20 minutes, then adding 1.8-2.0 g of ferroferric oxide magnetic powder and 1.0-1.2 g of sodium borate into the beaker, stirring and mixing for 25-35 minutes under the heating of a water bath at 55-60 ℃, then pouring the stirred mixture into a three-neck flask, introducing nitrogen, dropwise adding 4.0-4.5 ml of polyethylene glycol, heating to 75-85 ℃, adjusting the pH value of the system to be 9.4-9.7 by using a boric acid solution, and stirring and reacting for 50-60 minutes;
(2) after the reaction is finished, cooling to 35-40 ℃, sequentially using acetone and ethanol to respectively perform ultrasonic cleaning, heating and evaporating the obtained filtrate at the temperature of 100-105 ℃, separating a solid product, using deionized water and hexane to respectively clean for 2-3 times, then drying for 2-3 hours at the temperature of 55-60 ℃ in vacuum to obtain a dried product, dispersing the dried product in ethylenediamine and deionized water, and performing ultrasonic dispersion for 15-20 minutes to obtain a mixture;
(3) transferring the mixture into a polytetrafluoroethylene-lined high-pressure reaction kettle, carrying out heat preservation reaction at the temperature of 160-165 ℃ for 14-16 hours under the pressure of 1.1-1.2MPa, naturally cooling to room temperature after the reaction is finished, taking out the product, sequentially cleaning for 4-5 times by using deionized water and absolute ethyl alcohol, drying the product at the temperature of 100-110 ℃ for 4-5 hours, placing the product into a crucible, calcining for 3-4 hours in a muffle furnace at the temperature of 470-490 ℃, cooling and grinding into powder.
2. The catalyst for improving the synthesis conversion rate of dioctyl phthalate plasticizer according to claim 1, wherein the mass concentration of sodium hydroxide solution in step (1) is 8-10%.
3. The catalyst for increasing the synthesis conversion rate of dioctyl phthalate plasticizer according to claim 1, wherein the pH value of said boric acid solution in the step (1) is 4.0-4.2.
4. The catalyst for improving the synthesis conversion rate of dioctyl phthalate plasticizer according to claim 1, wherein the acetone and ethanol in the step (2) are respectively subjected to ultrasonic cleaning process: uniformly dispersing the product and the solvent according to the mass ratio of 1:3.0-3.2, then carrying out ultrasonic oscillation for 5-6 minutes in an ultrasonic cleaner, and filtering.
5. The catalyst for improving the synthesis conversion rate of dioctyl phthalate plasticizer according to claim 1, wherein the dry matter in the step (2) is dispersed in ethylenediamine and deionized water in the mass ratio of 1:5.0-5.5: 7.2-7.4.
6. The catalyst for improving the synthesis conversion rate of dioctyl phthalate plasticizer according to claim 1, wherein the catalyst prepared in step (3) has a particle size of 50-80 nm.
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DE4333324A1 (en) * 1993-09-30 1995-04-06 Hoechst Ag Decyl alcohol mixtures, phthalic acid esters obtainable therefrom and their use as plasticizers
CN101234355B (en) * 2008-03-06 2011-02-23 郭立耀 High-efficiency catalyst for synthesizing di(2-ethylhexyl) terephthalate
CN101786601B (en) * 2010-03-23 2013-01-09 济南大学 Preparation method of compound nano particle with Fe3O4/CoO core shell structure
CN104418748B (en) * 2013-08-22 2016-03-23 中国科学院大连化学物理研究所 A kind of o-Xylene Oxidation in Liquid Phase is coupled with esterification and prepares the method for Bisphthalate
CN104403090A (en) * 2014-11-20 2015-03-11 郑建东 Production method of environment-friendly polyester plasticizer
CN104592030B (en) * 2014-12-16 2017-01-18 南京化工职业技术学院 Method for synthesizing phthalate compounds
CN105417589A (en) * 2015-09-21 2016-03-23 华南师范大学 Preparation method for shuttle-shaped ferroferric oxide-cobaltosic oxide self-assembly structure compound

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