CN115724740A - Treatment method of low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] - Google Patents
Treatment method of low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] Download PDFInfo
- Publication number
- CN115724740A CN115724740A CN202211470265.9A CN202211470265A CN115724740A CN 115724740 A CN115724740 A CN 115724740A CN 202211470265 A CN202211470265 A CN 202211470265A CN 115724740 A CN115724740 A CN 115724740A
- Authority
- CN
- China
- Prior art keywords
- tert
- hydroxyphenyl
- butyl
- beta
- propionate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Abstract
The invention discloses a method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], which comprises the following steps: (1) Dissolving a pentaerythritol tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] crude product in a mixed solvent, heating and refluxing, cooling for crystallization, and performing suction filtration to obtain a crystal; (2) Adding hot alkali solution into the crystal, introducing nitrogen gas for bubbling, rolling and stirring, performing suction filtration to remove liquid, repeating the steps once, adding pure water for washing, and performing suction filtration to obtain a filtrate; (3) The filtrate was stirred and treated with hot steam to obtain low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ]. The invention can reduce the smell of the product, is beneficial to the health of human bodies and is environment-friendly in the application field.
Description
Technical Field
The invention relates to a method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], belonging to the technical field of antioxidants.
Background
The antioxidant 1010 (tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester) is a high molecular weight hindered phenol antioxidant, can effectively prevent the oxidation aging reaction of the polymer caused by light and heat, and has good compatibility with most polymers.
In the production process of the antioxidant 1010, substances with large odor, such as raw materials, byproducts or solvents, such as methanol, DMF, ethyl acetate, phenol and the like, can be remained in the product, so that the product has large odor, is not environment-friendly and is not beneficial to human health.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], which can reduce the odor of products and is beneficial to human health and environmental protection in the application field.
In order to achieve the purpose, the invention adopts the following technical scheme: a method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] comprising the steps of:
(1) Dissolving a pentaerythritol tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] crude product in a mixed solvent, heating and refluxing for 3-4 h, cooling, crystallizing, and performing suction filtration to obtain a crystal;
(2) Adding hot alkali solution into the crystal, introducing nitrogen for bubbling, rolling and stirring for 1-1.5 h, then performing suction filtration to remove liquid, repeating the process once, adding pure water for washing for 2-3 times, and performing suction filtration to obtain a filtrate;
(3) Stirring the filtrate, and performing steam treatment for 9-11.5 h by adopting hot steam to obtain low-odor tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester;
the low-odor pentaerythritol tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] has an odor rating of 2 to 2.5 according to the VDA270 standard.
Wherein, in the step (3), the specific steps of the steam treatment are as follows: firstly, under 0.1Mpa, hot steam flows and is introduced for treatment for 1-1.5 h, then the pressure is increased to 0.15-0.2 Mpa, the heat preservation and pressure maintenance is carried out for 3.5-4 h after the hot steam is filled, then the pressure is reduced to 0.1Mpa, the hot steam flows and is introduced for treatment for 1-1.5 h, then the pressure is reduced to 0.08-0.09 Mpa, the heat preservation and pressure maintenance is carried out for 2.5-3 h after the hot steam is filled, then the pressure is increased to 0.1Mpa, and the hot steam flows and is introduced for treatment for 1-1.5 h.
Wherein the temperature of the hot steam is controlled at 100 deg.C under 0.1MPa.
Wherein the temperature of the hot steam is controlled between 125 and 135 ℃ under the pressure of 0.15 to 0.2 MPa.
Wherein the temperature of the hot steam is controlled between 80 and 90 ℃ under 0.08 to 0.09 Mpa.
Wherein, in the step (1), the mass of the crude product of the tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester and the volume of the mixed solvent are 1.
Wherein, in the step (1), the mixed solvent is formed by mixing ethyl acetate and methanol according to a volume ratio of 1.5-2.5 (v: v).
In the step (2), the alkali solution is one of sodium hydroxide and potassium hydroxide, and the mass fraction of the alkali solution is 0.25-0.45%.
Wherein, in the step (2), the temperature of the hot alkali solution is controlled to be 45-55 ℃.
Wherein, in the step (2), the volume of the hot alkali solution added each time and the mass of the antioxidant 1010 crude product are 1.5 (v: w).
Wherein, in the step (2), the pressure of the nitrogen bubbling is 0.1MPa.
The invention has the beneficial effects that: the treatment method of the invention not only reduces the odor of the product, but also further improves the purity of the product; the treatment method can treat the crude product of tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester obtained by different raw material production, and the obtained product has high purity, low smell and stronger stability; the treatment method adopts hot steam treatment, the treatment process is environment-friendly, the process is simple, the odor of the product can be further removed, and the aim of drying the product can be fulfilled; according to the invention, the technological processes of normal pressure treatment, pressurization and maintenance, normal pressure treatment, depressurization and maintenance and normal pressure treatment are sequentially carried out on the hot steam treatment, so that the odor removal effect of the product is better, and the quality of the product is also improved.
Detailed Description
In order to more clearly and completely illustrate the invention, the following examples are given by way of illustration and not by way of limitation.
Example 1
A method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] comprises the following steps:
(1) Putting 100g of a crude product of pentaerythritol tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] in a reactor, adding 600ml of a mixed solvent prepared by mixing ethyl acetate and methanol according to a volume ratio of 1.5 (v: v) for dissolving, heating and refluxing for 3h, cooling, crystallizing, and carrying out suction filtration to obtain a crystal;
(2) Putting the crystal into a reactor, adding 150ml of sodium hydroxide solution with the mass fraction of 0.25% and the temperature controlled between 45 ℃ and 55 ℃, introducing nitrogen bubbling at 0.1Mpa for rolling and stirring for 1h, then performing suction filtration to remove liquid, putting the crystal into the reactor, adding 150ml of sodium hydroxide solution with the mass fraction of 0.25% and the temperature controlled between 45 ℃ and 55 ℃, introducing nitrogen bubbling at 0.1Mpa for rolling and stirring for 1h, then performing suction filtration to remove liquid, adding 30ml of pure water for flushing, washing for 2 times, and performing suction filtration to obtain a filtrate;
(3) Putting the filtrate into a reactor, stirring the filtrate, firstly introducing hot steam with the temperature of 100 ℃ under the pressure of 0.1MPa for 1 hour, then pressurizing to 0.15MPa, filling the filtrate with the hot steam with the temperature of 125 ℃, keeping the temperature and pressure for 3.5 hours, then reducing the pressure to 0.1MPa, introducing the hot steam with the temperature of 100 ℃ for 1 hour, then reducing the pressure to 0.08MPa, filling the filtrate with the hot steam with the temperature of 80 ℃, keeping the temperature and pressure for 2.5 hours, then increasing the pressure to 0.1MPa, and introducing the hot steam with the temperature of 100 ℃ for 1 hour to obtain the tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; purity by HPLC assay, odor rating according to VDA270 standard, results as shown in table 1;
in this example, tetrakis [ β - (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] pentaerythritol was prepared using pentaerythritol and 3,5 methyl ester as raw materials and sodium methoxide as a catalyst, and was subjected to n-pentane extraction and water washing to obtain a crude product.
Example 2
A method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] comprises the following steps:
(1) Putting 100g of a crude product of tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester into a reactor, adding 700ml of a mixed solvent prepared by mixing ethyl acetate and methanol according to a volume ratio of 1;
(2) Putting the crystal into a reactor, adding 150ml of potassium hydroxide solution with the mass fraction of 0.3% and the temperature controlled between 45 and 55 ℃, introducing nitrogen bubbling at 0.1Mpa for rolling and stirring for 1.5h, then performing suction filtration to remove liquid, then putting the crystal into the reactor, adding 150ml of potassium hydroxide solution with the mass fraction of 0.3% and the temperature controlled between 45 and 55 ℃, introducing nitrogen bubbling at 0.1Mpa for rolling and stirring for 1.5h, then performing suction filtration to remove liquid, then adding 40ml of pure water for washing, washing for 3 times, and performing suction filtration to obtain a filtrate;
(3) Putting the filtrate into a reactor, stirring the filtrate, firstly introducing hot steam with the temperature of 100 ℃ under 0.1MPa for flowing and processing for 1.5h, then pressurizing to 0.175MPa, filling the hot steam with the temperature of 130 ℃, keeping the pressure and the temperature for 4h, then reducing the pressure to 0.1MPa, then introducing hot steam with the temperature of 100 ℃ for flowing and processing for 1.5h, then reducing the pressure to 0085MPa, filling the hot steam with the temperature of 85 ℃, keeping the pressure and the temperature for 3h, then increasing the pressure to 0.1MPa, and introducing the hot steam with the temperature of 100 ℃ for flowing and processing for 1.5h to obtain tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; purity by HPLC assay, odor rating according to VDA270 standard, results as shown in table 1;
in this example, pentaerythritol tetrakis [ β - (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] was prepared from pentaerythritol and 3, 5-methyl ester as raw materials and a basic ionic liquid as a catalyst, and the crude product was obtained by n-hexane extraction and water washing.
Example 3
A method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] comprises the following steps:
(1) Putting 100g of a crude product of tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester into a reactor, adding 800ml of a mixed solvent formed by mixing ethyl acetate and methanol according to a volume ratio of 1;
(2) Putting the crystal into a reactor, adding 150ml of potassium hydroxide solution with the mass fraction of 0.35% and the temperature controlled between 45 and 55 ℃, introducing nitrogen bubbling at 0.1Mpa for rolling and stirring for 1.25h, then performing suction filtration to remove liquid, then putting the crystal into the reactor, adding 150ml of potassium hydroxide solution with the mass fraction of 0.35% and the temperature controlled between 45 and 55 ℃, introducing nitrogen bubbling at 0.1Mpa for rolling and stirring for 1.25h, then performing suction filtration to remove liquid, then adding 35ml of pure water for washing, washing for 2 times, and performing suction filtration to obtain a filtrate;
(3) Putting the filtrate into a reactor, stirring the filtrate, firstly introducing hot steam with the temperature of 100 ℃ under 0.1MPa for flowing treatment for 1.2h, then pressurizing to 0.2MPa, filling the hot steam with the temperature of 135 ℃, keeping the pressure and preserving the heat for 3.75h, then reducing the pressure to 0.1MPa, introducing hot steam with the temperature of 100 ℃ for flowing treatment for 1h, then reducing the pressure to 0.09MPa, filling the hot steam with the temperature of 90 ℃, keeping the pressure and preserving the heat for 2.75h, then increasing the pressure to 0.1MPa, and introducing the hot steam with the temperature of 100 ℃ for flowing treatment for 1.5h to obtain tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; purity by HPLC assay, odor rating according to VDA270 standard, results as shown in table 1;
in this example, pentaerythritol tetrakis [ β - (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] is prepared from pentaerythritol and 3, 5-methyl ester as raw materials, potassium tert-butoxide as a catalyst, and DMF as a solvent, and the crude product is obtained by liquid paraffin extraction and washing with water.
Example 4
A method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] comprises the following steps:
(1) Placing 100g of a crude product of pentaerythritol tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] in a reactor, adding 650ml of a mixed solvent formed by mixing ethyl acetate and methanol according to a volume ratio of 1;
(2) Putting the crystal into a reactor, adding 150ml of sodium hydroxide solution with the mass fraction of 0.45% and the temperature controlled between 45 and 55 ℃, introducing nitrogen bubbling at 0.1Mpa for rolling and stirring for 1.5h, then performing suction filtration to remove liquid, then putting the crystal into the reactor, adding 150ml of sodium hydroxide solution with the mass fraction of 0.45 and the temperature controlled between 45 and 55 ℃, introducing nitrogen bubbling at 0.1Mpa for rolling and stirring for 1.5h, then performing suction filtration to remove liquid, then adding 25ml of pure water for washing, washing for 3 times, and performing suction filtration to obtain a filtrate;
(3) Putting the filtrate into a reactor, stirring the filtrate, firstly introducing hot steam with the temperature of 100 ℃ under 0.1MPa for flowing treatment for 1.2h, then pressurizing to 0.18MPa, filling the hot steam with the temperature of 132 ℃, keeping the temperature and pressure for 3.5h, then reducing the pressure to 0.1MPa, introducing hot steam with the temperature of 100 ℃ for flowing treatment for 1h, then reducing the pressure to 0.09MPa, filling the hot steam with the temperature of 90 ℃, keeping the temperature and pressure for 3h, then pressurizing to 0.1MPa, introducing hot steam with the temperature of 100 ℃ for flowing treatment for 1.5h to obtain tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; purity by HPLC assay and odor rating by VDA270 standard as shown in table 1;
in this example, tetrakis [ β - (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] pentaerythritol ester was prepared using 2, 6-di-tert-butylphenol, methyl acrylate, and pentaerythritol as raw materials, and sodium methoxide as a catalyst, and the crude product was obtained by petroleum ether extraction and water washing.
Comparative example 1
The treatment process of comparative example 1 is the same as that of example 2, except for step (3), and step (3) of comparative example 1 is specifically carried out by: placing the filtrate in a reactor, stirring the filtrate, and introducing hot steam at 100 deg.C under 0.1Mpa for treatment for 11.5h to obtain tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; purity was analyzed by HPLC assay and odor rating according to VDA270 standard as shown in table 1.
Comparative example 2
The treatment process of comparative example 2 is the same as that of example 3, except for step (3), and the specific process of step (3) of comparative example 2 is as follows: firstly, under 0.1Mpa, introducing hot steam with the temperature of 100 ℃ for flowing treatment for 1.2h, firstly pressurizing to 0.2Mpa, filling hot steam with the temperature of 135 ℃, keeping the pressure and preserving the heat for 3.75h, then reducing the pressure to 0.1Mpa, and introducing hot steam with the temperature of 100 ℃ for flowing treatment for 5.25h to obtain tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; the purity was analyzed by HPLC and the odor rating according to VDA270 standard was determined as shown in Table 1.
Comparative example 3
The treatment process of this comparative example 3 is the same as that of example 4, except for step (3), and step (3) of this comparative example 3 is specifically a process of: firstly, hot steam with the temperature of 100 ℃ under 0.1Mpa flows and is introduced for treatment for 3.7h, then the pressure is reduced to 0.09Mpa, the hot steam with the temperature of 90 ℃ is filled, the temperature and the pressure are kept for 3h, then the pressure is increased to 0.1Mpa, and hot steam with the temperature of 100 ℃ flows and is introduced into a filtrate for treatment for 1.5h, thus obtaining the tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; purity was analyzed by HPLC assay and odor rating according to VDA270 standard as shown in table 1.
Comparative example 4
The treatment process of this comparative example 4 is the same as that of example 4, except for step (3), and step (3) of this comparative example 4 is specifically a process of: firstly reducing the pressure to 0.09Mpa, filling hot steam with the temperature of 90 ℃, keeping the pressure and preserving the heat for 10 hours, then increasing the pressure to 0.1Mpa, and introducing the hot steam with the temperature of 100 ℃ for treatment for 1.5 hours to obtain tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; the purity was analyzed by HPLC and the odor rating according to VDA270 standard was determined as shown in Table 1.
Comparative example 5
The treatment process of this comparative example 5 is the same as that of example 4, except for step (3), and step (3) of this comparative example 5 is specifically a process of: pressurizing to 0.18MPa, filling hot steam with the temperature of 132 ℃, keeping the temperature and the pressure for 10 hours, then pressurizing to 0.1MPa, and introducing the hot steam with the temperature of 100 ℃ for treatment for 1.5 hours to obtain tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; the purity was analyzed by HPLC and the odor rating according to VDA270 standard was determined as shown in Table 1.
Comparative example 6
The treatment process of comparative example 6 is the same as that of example 4 except that in step (1), the mixed solvent in step (1) of comparative example 6 is prepared by mixing ethyl acetate and methanol in a volume ratio of 1; the obtained tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; the purity was analyzed by HPLC and the odor rating according to VDA270 standard was determined as shown in Table 1.
Comparative example 7
The treatment process of comparative example 7 is the same as that of example 4, except that in step (2), nitrogen gas is not introduced in step (2) of comparative example 7, and only continuous stirring and tumbling are adopted; the obtained tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; the purity was analyzed by HPLC and the odor rating according to VDA270 standard was determined as shown in Table 1.
Comparative example 8
The treatment process of comparative example 8 is the same as that of example 4 except that in step (2), in step (2) of comparative example 8, the temperature of the 0.45 mass% sodium hydroxide solution is normal temperature; the obtained tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; the purity was analyzed by HPLC and the odor rating according to VDA270 standard was determined as shown in Table 1.
Comparative example 9
The treatment process of comparative example 9 is the same as that of example 4, except that in step (2), the temperature of the sodium hydroxide solution with a mass fraction of 0.45% in step (2) of comparative example 8 is controlled to be 60 to 65 ℃; the obtained tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester; the purity was analyzed by HPLC and the odor rating according to VDA270 standard was determined as shown in Table 1.
Comparative example 10
This comparative example 10A procedure for working up a crude product of pentaerythritol tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] comprises the following steps:
100g of crude antioxidant 1010 are mixed with 1000ml of ethyl acetate and methanol according to the volume ratio of 5: dissolving the mixed solvent of 1 (v/v), heating to reflux temperature, keeping for 20 minutes, cooling at room temperature, separating out crystals, performing suction filtration to obtain crystals, repeating the steps to obtain a second recrystallization product, and drying to obtain the pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] pentaerythritol ester; purity was analyzed by HPLC assay and odor rating according to VDA270 standard as shown in table 1.
Comparative example 11
Comparative example 11 the procedure for working up crude pentaerythritol tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] comprises the following steps:
100g of the crude antioxidant 1010 were dissolved in 1000ml of absolute ethanol under heating and reflux, filtered while hot, crystallized by cooling, filtered to give a second recrystallized product, dried to give pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] which was analyzed for purity by HPLC, and analyzed for odor grade according to the VDA270 standard, the results are shown in Table 1.
In the invention, the odor is judged according to the VDA270 standard, and the specific method of the VDA270 standard is as follows: adding 50ml of deionized water into a container, placing 30g of the treated product into the container, covering the container with a container cover, sealing, placing the container in a constant temperature experiment box at 40 ℃ for 24h, taking the container out of an oven, selecting 5 persons for evaluation in one test, and reevaluating when the difference between scores given by each person is greater than 2, wherein the grades are 1-no perception, 2-perception, but not uncomfortable, 3-direct perception, but still not uncomfortable, 4-uncomfortable, 5-uncomfortable, 6-unacceptable and 6-unacceptable.
TABLE 1
In conclusion, the treatment method of low-odor pentaerythritol tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] ester can treat crude pentaerythritol tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] ester obtained by different raw material production, so that the product has low odor, the odor grade of 2-2.5, high purity of more than 99.1%, more excellent crystal form and stronger stability; the invention has better effect of removing the smell of the product by the hot steam treatment, and can achieve the aim of drying the product and improve the quality of the product.
Finally, it should be noted that the above embodiments are only used for illustrating and not limiting the technical solutions of the present invention, and although the present invention has been described in detail with reference to the above embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made to the present invention without departing from the spirit and scope of the present invention, and all modifications or partial substitutions should be covered by the scope of the claims of the present invention.
Claims (10)
1. A method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] comprises the following steps: (1) Dissolving a pentaerythritol tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] crude product in a mixed solvent, heating and refluxing for 3-4 h, cooling, crystallizing, and performing suction filtration to obtain a crystal;
(2) Adding hot alkali solution into the crystal, introducing nitrogen for bubbling, rolling and stirring for 1-1.5 h, then performing suction filtration to remove liquid, repeating the process once, adding pure water for washing for 2-3 times, and performing suction filtration to obtain a filtrate;
(3) Stirring the filtrate, and carrying out steam treatment for 9-11.5 h by adopting hot steam treatment to obtain low-odor tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester.
2. The method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] according to claim 1, wherein the steam treatment in step (3) comprises the following steps: firstly, under 0.1Mpa, leading in hot steam for 1-1.5 h, then increasing the pressure to 0.15-0.2 Mpa, keeping the temperature and pressure for 3.5-4 h after being filled with the hot steam, then reducing the pressure to 0.1Mpa, leading in the hot steam for 1-1.5 h, then reducing the pressure to 0.08-0.09 Mpa, keeping the temperature and pressure for 2.5-3 h after being filled with the hot steam, then increasing the pressure to 0.1Mpa, and leading in the hot steam for 1-1.5 h.
3. The method of treating pentaerythritol tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] with a low odor according to claim 2, wherein the temperature of the hot steam is controlled at 100 ℃ under 0.1Mpa.
4. The method for treating pentaerythritol tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] with low odor according to claim 2, wherein the temperature of the hot steam is controlled to be 125-135 ℃ at 0.15-0.2 MPa.
5. The method for treating pentaerythritol tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] with low odor according to claim 2, wherein the temperature of the hot steam is controlled to be 80 to 90 ℃ at 0.08 to 0.09 Mpa.
6. The method for processing the low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] according to claim 1, wherein in the step (1), the ratio of the mass of the crude product of the pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] to the volume of the mixed solvent is 1.
7. The method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] according to claim 1, wherein the mixed solvent is a mixture of ethyl acetate and methanol in a volume ratio of 1.5 to 2.5 (v: v).
8. The method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] according to claim 1, wherein the alkaline solution is one of sodium hydroxide and potassium hydroxide, and the mass fraction of the alkaline solution is 0.25-0.45%.
9. The method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] according to claim 1, wherein the temperature of said hot alkaline solution is controlled to 45-55 ℃.
10. The method for treating low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] according to claim 1, wherein the volume of the hot alkali solution added to the crude antioxidant 1010 per time is 1.5 (v: w).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211470265.9A CN115724740B (en) | 2022-11-23 | 2022-11-23 | Treatment method of low-odor tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211470265.9A CN115724740B (en) | 2022-11-23 | 2022-11-23 | Treatment method of low-odor tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115724740A true CN115724740A (en) | 2023-03-03 |
| CN115724740B CN115724740B (en) | 2023-07-07 |
Family
ID=85297751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211470265.9A Active CN115724740B (en) | 2022-11-23 | 2022-11-23 | Treatment method of low-odor tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115724740B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5055606A (en) * | 1989-08-16 | 1991-10-08 | Witco Corporation | Alkylthiopropionic pentaerythritol esters and solvent refining thereof |
| US20080146823A1 (en) * | 1995-01-27 | 2008-06-19 | Kulkarni Madhu V | Method of making purified odor free tocopherol acetate |
| US20100210872A1 (en) * | 2009-02-13 | 2010-08-19 | Nan Ya Plastics Corporation | Method for making hindered phenolic antioxidant |
| CN112876666A (en) * | 2021-01-14 | 2021-06-01 | 长华化学科技股份有限公司 | Low-aldehyde and low-odor polyether polyol and preparation method and application thereof |
-
2022
- 2022-11-23 CN CN202211470265.9A patent/CN115724740B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5055606A (en) * | 1989-08-16 | 1991-10-08 | Witco Corporation | Alkylthiopropionic pentaerythritol esters and solvent refining thereof |
| US20080146823A1 (en) * | 1995-01-27 | 2008-06-19 | Kulkarni Madhu V | Method of making purified odor free tocopherol acetate |
| US20100210872A1 (en) * | 2009-02-13 | 2010-08-19 | Nan Ya Plastics Corporation | Method for making hindered phenolic antioxidant |
| CN112876666A (en) * | 2021-01-14 | 2021-06-01 | 长华化学科技股份有限公司 | Low-aldehyde and low-odor polyether polyol and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115724740B (en) | 2023-07-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1772829A (en) | High stability color-less rosin pentaerythrite ester and its prepn | |
| JP4796695B2 (en) | Method for recovering plant sterols | |
| CN106946716B (en) | A kind of benzalkonium chloride monomer synthesis technology | |
| CN103772186B (en) | A kind of process for purification of fermentation organic acid | |
| CN107673985B (en) | Preparation process of high-yield N, N-dimethylacrylamide | |
| CN115724740A (en) | Treatment method of low-odor pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] | |
| CN113214078A (en) | Method for recycling and preparing dioctyl terephthalate by utilizing terephthalic acid production waste | |
| CN106831446B (en) | A kind of improved pharmaceutical grade benzalkonium chloride monomer production method | |
| CN113292467B (en) | Method for purifying vitamin A oil mother liquor by using alcohol-containing alkali liquor | |
| CN102382044A (en) | Purification method for 2,3-dimethylpyridine | |
| CN113121378B (en) | Synthesis method of acetamino diethyl malonate | |
| EP4335857A1 (en) | Method for purifying sucralose-6-ethyl ester | |
| JP7138853B2 (en) | Method for producing hydroxy-substituted aromatic compound | |
| CN110272391B (en) | Refining method of minoxidil | |
| CN101575262B (en) | Method for reducing content of 2-methylnaphthalene impurity | |
| CN103254102B (en) | A kind of method of purifying acrylamide alkyl sulfonic acid | |
| CN109053581B (en) | Preparation method of metronidazole benzoate | |
| CN110423222A (en) | A kind of preparation method of 4,5- diaminostilbene-(2- ethoxy) pyrazoles sulfate | |
| CN113024484B (en) | Method for purifying and preparing high-purity promoter CZ and application thereof | |
| CN116283554B (en) | Industrial separation and purification method of trans-2-butenoic acid | |
| CN114573744B (en) | Method for reducing residual styrene-acrylonitrile copolymer resin and application thereof | |
| KR102252883B1 (en) | Method for purifying organic acids | |
| CN102746148A (en) | Method for purifying dimethyl succinate | |
| CN107417533B (en) | Dimethyl isophthalate and process for producing the same | |
| KR100619115B1 (en) | Method To Separate Sterol That There Is No Smell Of Great Soya From Greate Soya Milk Deodorization Distillation Quantity |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |