KR102412089B1 - A method for refining DMTS - Google Patents

Abstract

The present invention relates to a method for purifying DMTS, and more particularly, (a) preparing a first mixture by stirring DMTS and a first solvent; (b) cooling the first mixture; (c) adding a second solvent to the cooled first mixture and then stirring to prepare a second mixture; (d) adding a third solvent to the second mixture and then stirring to prepare a third mixture; (e) cooling the third mixture to crystallize; (f) separating the crystallized third mixture into a filtrate and a first solid by filtration; And (g) relates to a method for purifying DMTS comprising the step of drying the first solid.
The present invention can provide a method for purifying DMTS for producing high-purity DMTS through simple processes of dissolution, recrystallization, filtration and drying.

Description

Refining method of DMTS {A method for refining DMTS}

The present invention relates to a method for purifying DMTS, and more particularly, to a method for preparing high-purity DMTS through simple processes of dissolution, recrystallization, filtration and drying.

One of the most important processes when synthesizing a compound is purification, which refers to the process of selectively separating and obtaining a desired compound from a mixture of various compounds.

Recrystallization is the most widely used method for purifying solid compounds.

Recrystallization is a method for purifying a compound, and refers to a process of dissolving a solid material having a large solubility difference according to temperature at a high temperature to make a saturated solution, and then slowly cooling it to obtain a pure solid.

On the other hand, DMTS (Drometrizole trisiloxane) is known under the trade name Mexoryl XL or Silatrizole, and is widely used as a sunscreen.

In relation to recrystallization of the compound, various studies have been conducted to effectively remove moisture and impurities to prepare a compound of high purity.

However, the prior art cannot be stably used as a raw material for cosmetics, pharmaceuticals, electronic devices, etc. due to a high content of impurities in the compound.

Korean Patent Registration 10-0636953 B1

The present invention is to solve the problems of the prior art, and an object of the present invention is to provide a method for preparing high-purity DMTS through simple processes of dissolution, recrystallization, filtration and drying.

In order to achieve the above object, the present invention comprises the steps of (a) preparing a first mixture by stirring DMTS and a first solvent;

(b) cooling the first mixture;

(c) adding a second solvent to the cooled first mixture and then stirring to prepare a second mixture;

(d) adding a third solvent to the second mixture and then stirring to prepare a third mixture;

(e) cooling the third mixture to crystallize;

(f) separating the crystallized third mixture into a filtrate and a first solid by filtration; and

(g) provides a method for purifying DMTS comprising the step of drying the first solid.

In one embodiment of the present invention, in step (a), 100 parts by weight of DMTS and 100 to 1,000 parts by weight of the first solvent are mixed and stirred.

In an embodiment of the present invention, in step (a), methanol and acetone are mixed and used as the first solvent.

In one embodiment of the present invention, step (c) is characterized in that methanol is used as the second solvent.

In one embodiment of the present invention, step (d) is characterized in that methanol is used as the third solvent.

The present invention can provide a method for purifying DMTS for producing high-purity DMTS through simple processes of dissolution, recrystallization, filtration and drying.

Hereinafter, the present invention will be described in detail based on Examples. Terms, examples, etc. used in the present invention are merely exemplified to explain the present invention in more detail and help those of ordinary skill in the art to understand, and the scope of the present invention should not be construed as being limited thereto.

Technical terms and scientific terms used in the present invention represent meanings commonly understood by those of ordinary skill in the art to which this invention belongs, unless otherwise defined.

The present invention comprises the steps of (a) preparing a first mixture by stirring DMTS and a first solvent;

(b) cooling the first mixture;

(c) adding a second solvent to the cooled first mixture and then stirring to prepare a second mixture;

(d) adding a third solvent to the second mixture and then stirring to prepare a third mixture;

(e) cooling the third mixture to crystallize;

(f) separating the crystallized third mixture into a filtrate and a first solid by filtration; and

(g) relates to a method for purifying DMTS comprising the step of drying the first solid.

According to the present invention, DMTS having uniform particle size and greatly improved purity compared to conventional DMTS can be manufactured through simple processes of dissolution, recrystallization, filtration and drying.

Since the DMTS has a low melting point, if a solvent with a high boiling point is used, the drying time may be prolonged, and crystals may be dissolved during the drying process.

In the present invention, by using the first solvent, the second solvent and the third solvent, the drying time is short and the crystal dissolution phenomenon during drying can be prevented.

In addition, if the crystals generated during recrystallization are large, the filtration is good, the purity is improved, and drying can be performed quickly at a low temperature. By using the first solvent, the second solvent and the third solvent, the The crystals can be large and the purity can be increased.

Step (a) is a step of preparing a first mixture by stirring drometrizole trisiloxane (DMTS) and a first solvent.

The first solvent may be acetone, methanol, ethanol, isopropyl alcohol, ethylene glycol, distilled water, or the like.

In the present invention, methanol and acetone may be mixed and used as the first solvent, and the weight ratio of methanol and acetone is preferably 40 to 70:30 to 60. When the weight ratio satisfies the numerical range, yield and purity can be maximized.

In the present invention, methanol, acetone and isopropyl alcohol may be mixed and used as the first solvent, and in this case, the weight ratio of methanol, acetone and isopropyl alcohol is preferably 100:30 to 60:5 to 20. When the weight ratio satisfies the numerical range, yield and purity can be maximized.

The first mixture may be mixed with 100 parts by weight of DMTS and 100 to 1,000 parts by weight of the first solvent and stirred at 40 to 60° C. for 1 to 10 hours.

Step (b) is a step of cooling the first mixture, the first mixture may be cooled to 20 ~ 30 ℃.

Also, in the present invention, after step (b), the cooled first mixture may be heated again to 40 to 60° C. and stirred for 1 to 10 hours. In this case, a fourth solvent may be added, and 10 to 30 parts by weight of the added fourth solvent may be used based on 100 parts by weight of the first solvent.

In the present invention, as the fourth solvent, methanol, acetone and isopropyl alcohol may be mixed and used, and in this case, the weight ratio of methanol, acetone and isopropyl alcohol is preferably 100:30-60:5-20. When the weight ratio satisfies the numerical range, yield and purity can be maximized.

The stirred mixture may be cooled to 20-30 °C again.

Step (c) is a step of preparing a second mixture by adding a second solvent to the cooled first mixture and stirring for 1 to 5 hours.

The second solvent may be acetone, methanol, ethanol, isopropyl alcohol, ethylene glycol, distilled water, or the like.

In this case, 30 to 70 parts by weight of the second solvent may be used based on 100 parts by weight of the first solvent.

In the present invention, it is preferable to use methanol as the second solvent.

In the present invention, methanol and acetone may be mixed and used as the second solvent, and the weight ratio of methanol and acetone is preferably 40 to 70:30 to 60. When the weight ratio satisfies the numerical range, yield and purity can be maximized.

In the present invention, methanol, acetone and isopropyl alcohol may be mixed and used as the second solvent, and in this case, the weight ratio of methanol, acetone and isopropyl alcohol is preferably 100:30-60:5-20. When the weight ratio satisfies the numerical range, yield and purity can be maximized.

Step (d) is a step of preparing a third mixture by adding a third solvent to the second mixture and stirring for 1 to 5 hours.

The third solvent may be acetone, methanol, ethanol, isopropyl alcohol, ethylene glycol, distilled water, or the like.

In this case, 30 to 70 parts by weight of the third solvent may be used based on 100 parts by weight of the first solvent.

In the present invention, it is preferable to use methanol as the third solvent.

In the present invention, methanol and acetone may be mixed and used as the third solvent, and in this case, the weight ratio of methanol and acetone is preferably 40 to 70:30 to 60. When the weight ratio satisfies the numerical range, yield and purity can be maximized.

In the present invention, methanol, acetone and isopropyl alcohol may be mixed and used as the third solvent, and in this case, the weight ratio of methanol, acetone and isopropyl alcohol is preferably 100:30-60:5-20. When the weight ratio satisfies the numerical range, yield and purity can be maximized.

The step (e) is a step of cooling the third mixture to crystallize, and the third mixture may be cooled to 5-20° C. to crystallize DMTS.

The step (f) is a step of separating the crystallized third mixture into a filtrate and a first solid by filtration, and may be separated by a screen method, a centrifugal separation method, a press method, a vacuum filtration method, or the like.

The step (g) is a step of drying the first solid, preferably drying at 30 to 45° C. for 1 to 20 hours.

The present invention can prepare high-purity DMTS through simple processes of dissolution, recrystallization, filtration and drying.

DMTS of the present invention has a low content of impurities in the compound and very high purity, so it can be stably used as a raw material for sunscreen, cosmetics, pharmaceuticals, electronic devices, and the like.

Hereinafter, the present invention will be described in detail through Examples and Comparative Examples. The following examples are only exemplified for the practice of the present invention, and the content of the present invention is not limited by the following examples.

(Example 1)

A first mixture was prepared by stirring 100 parts by weight of DMTS, 60 parts by weight of methanol, and 60 parts by weight of acetone at 50° C. for 2 hours.

The first mixture was cooled to room temperature.

After adding 60 parts by weight of methanol to the cooled first mixture, the mixture was stirred for 2 hours to prepare a second mixture.

After adding 60 parts by weight of methanol to the second mixture, the mixture was stirred for 2 hours to prepare a third mixture.

The third mixture was cooled to 10° C. and crystallized.

The crystallized third mixture was filtered and separated into a filtrate and a first solid.

DMTS was obtained by drying the first solid.

(Example 2)

DMTS was obtained in the same manner as in Example 1, except that 24 parts by weight of methanol was added to the second mixture.

(Example 3)

DMTS was obtained in the same manner as in Example 1, except that 96 parts by weight of methanol was added to the second mixture.

(Comparative Example 1)

A first mixture was prepared by stirring 100 parts by weight of DMTS, 180 parts by weight of methanol, and 60 parts by weight of acetone at 50° C. for 2 hours.

The first mixture was cooled to 10° C. and crystallized.

The crystallized first mixture was filtered and separated into a filtrate and a first solid.

The first solid was vacuum dried to obtain DMTS.

(Comparative Example 2)

100 parts by weight of DMTS, 160 parts by weight of isopropyl alcohol, 70 parts by weight of methanol and 10 parts by weight of distilled water were stirred at 50° C. for 2 hours to prepare a first mixture.

The first mixture was cooled to 10° C. and crystallized.

The crystallized first mixture was filtered and separated into a filtrate and a first solid.

The first solid was vacuum dried to obtain DMTS.

The purity of DMTS prepared in Examples and Comparative Examples was measured and shown in Table 1.

division water(%) Example 1 99.9 Example 2 95.8 Example 3 96.1 Comparative Example 1 94.8 Comparative Example 2 94.2

From the results of Table 1, it can be confirmed that Examples 1 to 3 have excellent purity, and in particular, Example 1 has the highest purity.

On the other hand, it can be seen that Comparative Examples 1 and 2 are inferior in purity to Examples.

Claims (5)

(a) preparing a first mixture by stirring DMTS and a first solvent;
(b) cooling the first mixture;
(c) adding a second solvent to the cooled first mixture and then stirring to prepare a second mixture;
(d) adding a third solvent to the second mixture and then stirring to prepare a third mixture;
(e) cooling the third mixture to crystallize;
(f) separating the crystallized third mixture into a filtrate and a first solid by filtration; and
(g) in the purification method of DMTS comprising the step of drying the first solid,
Step (a) prepares a first mixture by stirring DMTS and the first solvent at 40 to 60 ℃,
Step (a) uses a mixture of methanol and acetone as a first solvent,
The weight ratio of methanol and acetone is 40-70:30-60,
The step (b) is to cool the first mixture to 20 ~ 30 ℃,
30 to 70 parts by weight of the second solvent in step (c) is used based on 100 parts by weight of the first solvent,
The second solvent is methanol,
30 to 70 parts by weight of the third solvent in step (d) is used based on 100 parts by weight of the first solvent,
The third solvent is methanol,
The step (e) is crystallized by cooling the third mixture to 5 ~ 20 ℃,
After step (b), the temperature of the cooled first mixture is raised to 40-60 ° C., and a fourth solvent is added thereto and stirred, and further comprising the step of cooling the stirred mixture to 20-30 ° C.,
The fourth solvent is used in an amount of 10 to 30 parts by weight based on 100 parts by weight of the first solvent,
The fourth solvent is used by mixing methanol, acetone and isopropyl alcohol,
The method for purifying DMTS, characterized in that the weight ratio of the methanol, acetone and isopropyl alcohol is 100:30-60:5-20.
The method of claim 1,
In step (a), 100 parts by weight of DMTS and 100 to 1,000 parts by weight of the first solvent are mixed and stirred.
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