Application of sodium bisulfite in deodorization of crude 1,2-hexanediol and method for deodorization of crude 1,2-hexanediol

Abstract

The present invention belongs to the technical field of cosmetic raw materials, and specifically discloses the application of sodium bisulfite in the deodorization of 1,2-hexanediol crude products and a method for deodorizing 1,2-hexanediol crude products. The method for deodorizing 1,2-hexanediol crude products of the present invention is to first mix the 1,2-hexanediol crude product with a sodium bisulfite aqueous solution for reaction to obtain a reaction solution; then the reaction solution is sequentially extracted and distilled to achieve the deodorization of the 1,2-hexanediol crude product, and obtain cosmetic grade 1,2-hexanediol. The present invention reacts with impurities in the 1,2-hexanediol crude product by sodium bisulfite, obtains 1,2-hexanediol without plastic or Chinese medicine odor, and can also achieve the refining of 1,2-hexanediol, which is suitable for application in advanced cosmetics; the deodorization method has simple process and low cost, and is suitable for industrial production.

Description

Technical Field

[0001] The invention relates to the technical field of cosmetic raw materials, in particular to application of sodium bisulfite in deodorizing crude 1,2-hexanediol and a method for deodorizing crude 1,2-hexanediol. Background Art

[0002] 1,2-Hexanediol is a colorless and odorless liquid and is an important raw material for pesticides such as pyrethroids and cyclic musk. At the same time, due to its excellent moisturizing and antiseptic properties, it is also widely used in cosmetics. At present, the production of 1,2-hexanediol mainly uses 1-hexene as the raw material, which is oxidized with hydrogen peroxide to generate an epoxy intermediate, and then hydrolyzed to obtain a crude 1,2-hexanediol. This crude product has the smell of plastic or traditional Chinese medicine. Even after distillation and purification, the smell cannot be completely removed, resulting in its inability to be used in the cosmetics field.

[0003] Cosmetic grade 1,2-hexanediol has been successfully prepared, but the preparation method has not been disclosed. Currently, there is no public technology that can produce odorless 1,2-hexanediol, resulting in a high price for cosmetic grade 1,2-hexanediol. Therefore, the art urgently needs to develop a method for deodorizing crude 1,2-hexanediol that is simple in process, low in cost, and easy to industrialize. Summary of the invention

[0004] In view of this, the present invention provides an application of sodium bisulfite in deodorizing crude 1,2-hexanediol and a method for deodorizing crude 1,2-hexanediol, so as to solve the problem that it is difficult to prepare cosmetic-grade 1,2-hexanediol.

[0005] In order to achieve the above object, the present invention adopts the following technical solution:

[0006] Application of sodium bisulfite in deodorization of crude 1,2-hexanediol.

[0007] Another object of the present invention is to provide a method for deodorizing crude 1,2-hexanediol, comprising the steps of:

[0008] The crude 1,2-hexanediol product is mixed with an aqueous sodium bisulfite solution for reaction to obtain a reaction solution, and the reaction solution is sequentially extracted and distilled to achieve deodorization of the crude 1,2-hexanediol product;

[0009] The preparation method of the crude 1,2-hexanediol is as follows: 1-hexene is first subjected to epoxidation reaction and then hydrolyzed to obtain the crude 1,2-hexanediol.

[0010] Preferably, the sodium bisulfite aqueous solution is a saturated sodium bisulfite aqueous solution.

[0011] Preferably, the mass ratio of the sodium bisulfite aqueous solution to the crude 1,2-hexanediol is 0.5-5:100.

[0012] Preferably, the reaction temperature is 15 to 35° C., the reaction time is 2 to 6 hours, and the reaction is carried out under stirring.

[0013] Preferably, the extraction solvent of the extraction is a mixture of toluene and water;

[0014] The mass ratio of toluene to crude 1,2-hexanediol in the extraction solvent is 1-4:1, and the mass ratio of water to crude 1,2-hexanediol is 0.2-0.5:1.

[0015] It can be seen from the above technical solutions that, compared with the prior art, the present invention has the following beneficial effects:

[0016] 1. In order to make up for the shortcomings of the existing process, the present invention discloses a method of using sodium bisulfite to react with taste impurities, and then extracting and rectifying to obtain 1,2-hexanediol without the smell of plastic or traditional Chinese medicine. At the same time, the 1,2-hexanediol can be refined and is suitable for use in high-end cosmetics.

[0017] 2. The 1,2-hexanediol deodorization method provided by the present invention has simple process, low cost and is suitable for industrial production. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are only embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on the provided drawings without paying creative work.

[0019] Figure 1 This is the NMR spectrum of the deodorized product of Example 1 of the present invention. DETAILED DESCRIPTION

[0020] The invention provides application of sodium bisulfite in deodorizing crude 1,2-hexanediol.

[0021] The present invention also provides a method for deodorizing crude 1,2-hexanediol, comprising the following steps:

[0022] The crude 1,2-hexanediol product is mixed with a sodium bisulfite aqueous solution for reaction to obtain a reaction solution, and the reaction solution is sequentially extracted and distilled to achieve deodorization of the crude 1,2-hexanediol product.

[0023] In the present invention, the preparation method of the crude 1,2-hexanediol is to firstly epoxidize 1-hexene and then hydrolyze it to obtain the crude 1,2-hexanediol.

[0024] In the present invention, the sodium bisulfite aqueous solution is a saturated sodium bisulfite aqueous solution.

[0025] In the present invention, the mass ratio of the sodium bisulfite aqueous solution to the crude 1,2-hexanediol is 0.5-5:100, preferably 0.8-4:100, further preferably 1-3:100, and further preferably 2:100.

[0026] In the present invention, the reaction temperature is 15-35°C, specifically 18°C, 20°C, 22°C, 25°C, 28°C, 30°C, 32°C; the reaction time is 2-6h, specifically 2h, 3h, 4h, 5h, 6h; the reaction is carried out under stirring conditions, and the stirring rate is preferably 30-100rpm, specifically 30rpm, 40rpm, 50rpm, 60rpm, 70rpm, 80rpm, 90rpm, 100rpm.

[0027] In the present invention, the extraction solvent of the extraction is a mixture of toluene and water.

[0028] In the present invention, the mass ratio of toluene to crude 1,2-hexanediol in the extraction solvent is 1 to 4:1, preferably 1.5 to 3.5:1, more preferably 2 to 3:1, and further preferably 2.5:1; the mass ratio of water to crude 1,2-hexanediol is 0.2 to 0.5:1, preferably 0.25 to 0.45:1, more preferably 0.3 to 0.4:1, and further preferably 0.35:1. The crude 1,2-hexanediol refers to the amount of crude 1,2-hexanediol added to the reaction solution before the reaction.

[0029] In the present invention, an extraction phase and a raffinate phase are obtained after extraction, wherein the extraction phase is an organic phase, and the purpose of the rectification is to remove toluene in the extraction phase.

[0030] The technical solutions in the embodiments of the present invention are described clearly and completely below. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0031] The crude 1,2-hexanediol in the embodiments of the present invention is obtained by first epoxidizing 1-hexene and then hydrolyzing it. The manufacturer is Zhejiang Liansheng Chemical Co., Ltd.

[0032] Example 1

[0033] Add 100 g of crude 1,2-hexanediol to the reaction flask, add 1.5 g of saturated sodium bisulfite aqueous solution, and stir at 60 rpm for 4 h at 25 ° C. Add 250 g of toluene and 35 g of water, stir, stand and separate the liquids, and distill the upper organic phase to remove toluene and water (most of the water can be removed by extraction and separation, but some water still remains, and water and toluene need to be removed together during distillation) to obtain 92 g of 1,2-hexanediol.

[0034] The NMR spectrum of 1,2-hexanediol obtained is as follows Figure 1 As shown, through Figure 1 It can be seen that the product prepared by the present invention is still 1,2-hexanediol with high purity.

[0035] Example 2

[0036] Add 100 g of crude 1,2-hexanediol and 1.0 g of saturated sodium bisulfite aqueous solution to the reaction flask, stir at 30 rpm for 3 h at 30 °C. Add 300 g of toluene and 40 g of water, stir, stand for separation, and distill the upper organic phase to remove toluene and water to obtain 88 g of 1,2-hexanediol.

[0037] Example 3

[0038] Add 100 g of crude 1,2-hexanediol to the reaction flask, add 2.0 g of saturated sodium bisulfite aqueous solution, and stir at 100 rpm for 5 h at 20°C. Add 200 g of toluene and 30 g of water, stir, stand and separate, and distill the upper organic phase to remove toluene and water to obtain 93 g of 1,2-hexanediol.

[0039] Experimental Example 1

[0040] After multiple people evaluated the odor of the samples obtained in Examples 1 to 3 of the present invention, it was determined that the samples prepared by the method of the present invention had a lower odor than the commercially available products in South Korea.

[0041] Evaluation method of odor in products: Place a 50ml glass bottle containing 20ml of water in a water bath, heat to 50°C, add 2ml of 1,2-hexanediol sample (add Examples 1 to 3 and South Korea BAND B Co., Ltd respectively), shake well, open the bottle cap and smell the odor, compare with the commercial product (South Korea BAND B Co., Ltd), judge the odor level (with the above commercial product as the standard, set it to 5.0, the odor is less than the commercial product is divided into 1, 2, 3, 4 levels, the odor is greater than the commercial product is divided into 6, 7, 8, 9 levels, the smaller the level, the smaller the odor), by the method of multi-person evaluation, calculate the score by the average value, the lower the score, the better the odor removal effect. The specific test results of the products in each embodiment are shown in Table 1.

[0042] Table 1 Evaluation results

[0043]

[0044]

[0045] It can be seen from Table 1 that the odor of the samples obtained in Examples 1 to 3 of the present invention is lower than that of the commercial products in Korea.

[0046] The various embodiments in this specification are described in a progressive manner, and each embodiment focuses on the differences from other embodiments. The same or similar parts between the various embodiments can be referenced to each other.

[0047] The above description of the disclosed embodiments enables one skilled in the art to implement or use the present invention. Various modifications to these embodiments will be apparent to one skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the present invention. Therefore, the present invention will not be limited to the embodiments shown herein, but rather to the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. Application of sodium bisulfite in deodorization of crude 1,2-hexanediol.

2. A method for deodorizing crude 1,2-hexanediol, characterized in that: The steps include: The crude 1,2-hexanediol product is mixed with an aqueous sodium bisulfite solution for reaction to obtain a reaction solution, and the reaction solution is sequentially extracted and distilled to achieve deodorization of the crude 1,2-hexanediol product; The preparation method of the crude 1,2-hexanediol is as follows: 1-hexene is first subjected to epoxidation reaction and then hydrolyzed to obtain the crude 1,2-hexanediol.

3. A method for deodorizing crude 1,2-hexanediol according to claim 2, characterized in that: The sodium bisulfite aqueous solution is a saturated sodium bisulfite aqueous solution.

4. A method for deodorizing crude 1,2-hexanediol according to claim 3, characterized in that: The mass ratio of the sodium bisulfite aqueous solution to the crude 1,2-hexanediol is 0.5-5:

100.

5. A method for deodorizing crude 1,2-hexanediol according to claim 2 or 3, characterized in that: The reaction temperature is 15-35° C., the reaction time is 2-6 hours, and the reaction is carried out under stirring.

6. A method for deodorizing crude 1,2-hexanediol according to claim 5, characterized in that: The extraction solvent of the extraction is a mixture of toluene and water; The mass ratio of toluene to crude 1,2-hexanediol in the extraction solvent is 1-4:1, and the mass ratio of water to crude 1,2-hexanediol is 0.2-0.5:1.

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