KR100855343B1 - Method for manufacture of monoglyceride sulfonate - Google Patents

Abstract

 The present invention relates to a method for producing a monoglyceride sulfonate, and more particularly, animal oil which is Uji or pork fat in a solvent; Or neutralizing fatty acids derived from vegetable oils selected from the group consisting of palm oil, lauric acid, palm oil and palm kernel oil with an alkali metal solution to prepare an alkali metal salt of a single or mixed fatty acid, and a compound represented by the following formula (2); It relates to a method for producing a monoglyceride sulfonate prepared by reacting.

[Formula 1] [Formula 2]

(Wherein R is a saturated and unsaturated aliphatic hydrocarbon radical having 7 to 19 carbon atoms; M is sodium or potassium)

The production method of the present invention is economical because it can produce a large amount of monoglyceride sulfonate, which is a substance useful as a base for washing human body, using a manufacturing facility that is easy to handle from cheap fatty acids.

Alkali metal salts of fatty acids, monoglyceride sulfonates, anionic surfactants

Description

Method for producing monoglyceride sulfonate {METHOD FOR MANUFACTURE OF MONOGLYCERIDE SULFONATE}

The present invention relates to a method for preparing monoglyceride sulfonate, and more particularly, to a method for preparing monoglyceride sulfonate which can be produced in an economical manner using cheap fatty acids.

Monoalkylglyceryl sulfonates are known as one component of anionic surfactants. US Patent No. 3,960,782 discloses a method of using monoalkylglyceryl sulfonate as a component in a shampoo composition, and the preparation method thereof is as follows. That is, in the above method, 2,3-epoxy-1-propane sulfonic acid is synthesized by reacting epichlorohydrin and sodium bisulfite, and neutralized with sodium hydroxide, and sodium 2,3-dihydroxy-1-propane sulfo The monoalkyl glyceryl sulfonate is prepared through the esterification reaction with a fatty acid after synthesis. However, the above method requires relatively high temperature reaction conditions and excessive use of fatty acids, and after the reaction, excess unreacted fatty acids are dispersed in an organic solvent to be removed by manure or distilled using a vacuum decompression device. There is. In addition, in order to suppress bubbles generated during the reaction, an excess of fatty acid should be added at the beginning of the reaction. Moreover, although the method is a good way to prepare the target compound by removing excess unreacted fatty acid, the handling and control of the facility is not simple, and the reaction is poor as a reaction between the fatty acid and a salt which is poorly soluble in the fatty acid, resulting in a high overall yield. There is a disadvantage of decreasing.

In addition, the monoglyceride sulfonate may be prepared by the following method. That is, after the reaction of fatty acids with epichlorohydrin to synthesize 3-chloro-2-hydroxypropyl alkyl ester, the chloride group using a Strecker reaction using sodium sulfite and sodium bisulfite There is a method of producing by replacing with sulfonate. However, this method has the disadvantage that the intramolecular ester bonds and chlorides are easily hydrolyzed and the yield is reduced.

The present invention, in consideration of the problems of the prior art as described above, minimizes problems such as conventional hydrolysis or yield reduction, and cleans the human body in an economical manner using cheap fatty acids obtained by manufacturing facilities and easy manufacturing processes. It is an object to provide a process for the preparation of monoglyceride sulfonates suitable for use as anionic surfactants useful as a base.

Another object of the present invention is to provide a human detergent comprising the monoglyceride sulfonate prepared by the above method.

In order to achieve the above object, the present invention provides a method for producing a monoglyceride sulfonate,

Animal oil which is tallow or lard in solvent; Or neutralizing fatty acids derived from vegetable oils selected from the group consisting of palm oil, lauric acid, palm oil and palm kernel oil with an alkali metal solution to prepare an alkali metal salt of a single or mixed fatty acid, and the compound represented by the following Chemical Formula 2 It provides a method for producing a monoglyceride sulfonate represented by the following formula (1) prepared by the reaction.

[Formula 1]

[Formula 2]

In which R is a saturated and unsaturated aliphatic hydrocarbon radical having 7 to 19 carbon atoms; M is sodium or potassium.

In addition, the present invention provides a human detergent comprising the monoglyceride sulfonate prepared by the above method.

Hereinafter, the present invention will be described in detail.

The present invention is to provide a method for producing monoglycerides that are economical by using inexpensive fatty acids such as animal oil and vegetable oil, are hypoallergenic to the human body, and have excellent usability and moisturizing ability.

Referring to the production method of the monoglyceride sulfonate of the formula (1) of the present invention in more detail.

The present invention performs the step of preparing a compound of formula 2 to prepare the monoglyceride sulfonate. To this end, the present invention is prepared by dissolving the reducing agent with water and then adding epichlorohydrin to prepare the compound of Formula 2, which is an intermediate material. Preferably, the compound of formula 2 is sodium chlorohydroxy sulfonate. The reducing agent is preferably sodium sulfite, sodium bisulfite or sodium metabisulfite. The content of epichlorohydrin and the reducing agent, and the reaction conditions are in accordance with conventional methods.

Then, the present invention prepares the monoglyceride sulfonate of Chemical Formula 1 by a substitution esterification reaction by adding a compound of Chemical Formula 2, which is the intermediate substance, to an alkali metal salt of a single or mixed fatty acid.

The alkali metal salt of the fatty acid can be obtained by neutralization of the fatty acid. The fatty acid may be animal oil such as tallow or larch of Chemical Formula 3; Or cheaper higher fatty acids derived from vegetable oils such as palm oil, palm oil and palm kernel oil, and these may be used alone or in combination.

[Formula 3]

RCOOM

Wherein R is a saturated and unsaturated aliphatic hydrocarbon radical having 7 to 19 carbon atoms; M is sodium or potassium.

The neutralization of the fatty acid may be used by neutralizing the equivalent ratio 100%, but the reaction can be carried out in the presence of the free fatty acid. When the product is applied, the content of fatty acid may be determined depending on the use, but when the content of the free fatty acid exceeds 10% by weight, since the reaction time is generally slowed, it is preferable to use the content of the fatty acid less than 10% by weight.

In addition, the substitution ester reaction is preferably carried out under water alone or a mixed solvent of water and lower alcohol. The lower alcohols include methanol, ethanol, propanol and the like, with ethanol being most preferred. The mixing ratio of the water and the alcohol is preferably 20 to 70% by weight, more preferably 40 to 60% by weight based on water.

The reaction equivalent ratio of the alkali metal salt of the fatty acid and the compound of Formula 2 is preferably 1: 0.05 to 1.2 equivalents.

The content of the reactant is preferably 50 to 95% by weight, more preferably 60 to 80% by weight based on the amount of the solvent.

The reaction temperature is preferably 80 to 135 ° C, more preferably 95 to 125 ° C. After the reaction is completed, the present invention is dried to obtain the final product, the drying method may be a general drying method such as spray drying, drum dryer, hot air oven.

The final product thus obtained is composed of monoglyceride sulfonate, fatty acid alkali metal salt, fatty acid, sodium dihydroxy sulfonate salt, salt, and the like produced as a result of reaction with sodium chlorohydroxy sulfonate of the formula (2). The composition ratio of the final product is monoglyceride sulfonate (A), fatty acid alkali salt (B), fatty acid (C), sodium chlorohydroxy sulfonate (D), sodium dihydroxy sulfonate (E), and salt ( It is preferable that the weight ratio of F) is A / B / C / D + E / F = 1 / 0.15 / 0.07 / 0.12 / 0.18 to 1/22 / 1.2 / 0.25 / 0.25.

At this time, the content of the monoglyceride sulfonate is determined according to the equivalent ratio of the compound of formula 2 (preferably sodium chlorohydroxy sulfonate salt) to be used as an alkalizing agent with respect to fatty acid alkali metal salt, the use of human cleansing products Depending on the content can be adjusted.

In addition, the present invention can provide a human detergent comprising the monoglyceride sulfonate prepared by the above method as an anionic surfactant.

The human body cleaner includes soap, body shampoo, and the like, but the present invention is not limited thereto. In the case of preparing the soap, the present invention can directly put the final product in the soap maker to obtain a soap showing the quality as a high-quality soap excellent in moisturizing and skin protection. In addition, when the final product is applied to a body shampoo, it may exhibit excellent foaming and skin moisturizing properties.

The content of each component of the final product used in the human body cleaner may provide a useful component ratio in the application of the product, and may be determined and provided according to the formulation, properties, pH, packaging, storage condition and prescription content of each product. .                     

Hereinafter, the present invention will be described with reference to the following Examples and Comparative Examples. However, these examples are only for illustrating the present invention, and the present invention is not limited thereto.

EXAMPLE

Preparation Example 1

After dissolving sodium sulfite in water, epichlorohydrin was added and reacted to prepare sodium chlorohydroxy sulfonate powder.

Example 1

220 g of palm kernel oil fatty acid and 90 g of ethanol were added to the autoclave reactor to dissolve well, and 80 g of a 50% sodium hydroxide solution was added dropwise to neutralize all fatty acids to prepare a palm kernel oil fatty acid sodium salt. The reaction mixture was stirred at a temperature of 75 ° C. for 30 minutes, and 196.6 g of sodium chlorohydroxy sulfonate powder obtained in Preparation Example 1 was added thereto. After the reactor was sealed and heated to a temperature of 120 ° C., the anion quantitative test was measured and the reaction proceeded for 1 hour and 30 minutes until the content of monoglyceride sulfonate was maximized. After the reaction was completed, the reaction mixture was discharged and dried in a hot air oven to obtain 440 g of anionic surfactant having 63% of monoglyceride sulfonate.

The content analysis method of the monoglycerides is as follows. The content of monoglyceride sulfonate was measured by the reverse titration method of the dispersion titration method of Equation 1 below, where methylene blue was used as an indicator and when the chloroform layer and the water layer had the same blue color by dispersion titration of the anionic surfactant. .

[Equation 1]

Where

A is the amount of standard solution of cationic surfactant consumed in the titration of the blank test (ml),

B is the amount of cationic surfactant standard solution (ml) consumed in the titration of the sample solution,

f is the factor of the cationic surfactant standard solution,

S is the sampling amount (g) of the sample,

MW is the molecular weight of monoglyceride sulfonate.

Example 2

200 g of palm kernel oil fatty acid and 56 g of ethanol were added to the autoclave reactor to dissolve well, and 80 g of 50% sodium hydroxide solution was added dropwise to neutralize all fatty acids to prepare a palm kernel oil fatty acid sodium salt. The reaction mixture was stirred at a temperature of 75 ° C. for 30 minutes, and 98.3 g of sodium chlorohydroxy sulfonate powder obtained in Preparation Example 1 was added thereto. After the reactor was sealed and heated to a temperature of 120 ° C., the anion quantitative test was measured and the reaction was performed for 1 hour until the content of monoglyceride sulfonate was maximized. After the reaction was completed, the reaction mixture was discharged and dried in a hot air oven to obtain 320 g of anionic surfactant composition having a monoglyceride sulfonate content of 35%.                     

Example 3

Into a 400 L Sus reactor, 22 Kg of palm kernel oil fatty acid, 20 Kg of lauric fatty acid, and 13.5 Kg of ethanol were added to dissolve well, and 16 Kg of a 50% sodium hydroxide solution was added dropwise to neutralize all fatty acids. Salts were prepared. The reaction mixture was stirred at a temperature of 75 ° C. for 30 minutes, and 27.5 Kg of sodium chlorohydroxy sulfonate powder obtained in Preparation Example 1 was added thereto. After the reactor was sealed and heated to a temperature of 120 ° C., the anion quantitative test was measured and the reaction was performed for 2 hours until the content of monoglyceride sulfonate was maximized. After the reaction was completed, the reaction mixture was discharged and dried in a hot air oven to obtain 72 Kg of anionic surfactant composition having a monoglyceride sulfonate content of 54%.

Example 4

Into a 400 L Sus reactor, 22 Kg of palm kernel oil fatty acid, 20 Kg of lauric fatty acid, and 13.5 Kg of ethanol were added to dissolve well, and 16 Kg of a 50% sodium hydroxide solution was added dropwise to neutralize all fatty acids. Salts were prepared. The reactor internal temperature was 75 ° C. and stirred for 30 minutes, and 3.9 Kg of sodium chlorohydroxy sulfonate powder was added thereto. After the reactor was sealed and heated to a temperature of 120 ° C., the anion quantitative test was measured and the reaction was performed for 2 hours until the content of monoglyceride sulfonate was maximized. After the reaction was completed, the reaction mixture was discharged and dried in a hot air oven to obtain 51 Kg of anionic surfactant composition having a monoglyceride sulfonate content of 10.5%.

As described above, the production method of the present invention is economical because it can be produced in a large amount of a monoglyceride sulfonate, a substance useful as a base for washing human body, using a manufacturing facility that is easy to handle from cheap fatty acids. In addition, the monoglyceride sulfonate prepared by the method of the present invention has excellent biodegradability, foaming power and rinsing properties compared to conventional anionic surfactants, hypoallergenic to human body and excellent in use and moisturizing power, so it is used in human cleaning products. Suitable for That is, since the aqueous solution is neutral, it is highly irritating to the skin, so it is highly applicable to cleaning products for humans, and it has low solubility in water and high stability against hard water, so it is very suitable for solid cleaning products including cosmetic soap. It can be applied to liquid products by emulsification and dispersion.

Claims (5)

In the manufacturing method of the monoglyceride sulfonate, Animal oil which is tallow or lard in solvent; Or neutralizing fatty acids derived from vegetable oils selected from the group consisting of palm oil, lauric acid, palm oil and palm kernel oil with an alkali metal solution to prepare alkali metal salts of single or mixed fatty acids, and a compound represented by the following Chemical Formula 2 Method of producing a monoglyceride sulfonate characterized in that to produce a monoglyceride sulfonate represented by the following formula (1) by a substitution esterification reaction: [Formula 1]

[Formula 2]

Wherein R is a saturated and unsaturated aliphatic hydrocarbon radical having 7 to 19 carbon atoms; M is sodium or potassium. The method of claim 1, wherein the compound of Formula 2 is prepared by reacting epichlorohydrin with sodium sulfite, sodium bisulfite or sodium metabisulfite. The method of claim 1, wherein the reaction equivalent ratio of the alkali metal salt of the fatty acid and the compound of Formula 2 is 1: 0.05 to 1.2 equivalents. The method of claim 1, wherein the solvent is water or any mixed solvent selected from the group consisting of water, methanol, ethanol and propanol. delete