KR20200056836A - Di-alkyl glycerol based nonionic surfactants and preparation method thereof - Google Patents

Abstract

The present invention relates to a dialkyl glycerol-based nonionic surfactant and a method for preparing the same. More particularly, the present invention relates to an eco-friendly nonionic surfactant that exhibits excellent properties even without a phenyl group and has a 1-O-alkyl-3-O-alkyl group based on a glycerol form; and to an efficient method for preparing the same.

Description

Dialkyl glycerol type nonionic surfactant and preparation method thereof {Di-alkyl glycerol based nonionic surfactants and preparation method thereof}

The present invention relates to a dialkyl glycerol type nonionic surfactant and a method for preparing the same, and specifically, a nonionic surfactant having a 1- O -alkyl-3- O -alkyl group based on a glycerol form and a method for manufacturing the same will be.

Nonionic surfactants have lower critical micelle concentrations and greater association numbers, higher solubility, lower foaming force, hardness and less sensitivity to electrolyte concentrations than ionic surfactants. Of the various applications of nonionic surfactants, the detergent industry accounts for over 50% of production. In the detergent industry, washing at a low temperature, which is energy-saving, is important, and development of a nonionic surfactant having excellent solubility even at a low temperature is required.

Alkylphenol Ethoxylate (APE) is a nonionic surfactant widely used in various industries in Korea and abroad due to its good cleaning power and low cost. Types of APE include octyl phenol ethoxylate (OPE) and nonyl phenol ethoxylate (NPE), and have been used in various industries ranging from detergents, paints, herbicides, pesticides and cosmetics. . However, APE also does not decompose in aquatic water, and its residue is released into rivers, which has strong toxicity to submarine organisms, and is also transferred to the food chain, resulting in accumulation in the human body.

Domestic patent 10-1675787 has developed and reported a non-ionic surfactant with reduced toxicity and environmental hormone activity as a substitute surfactant for conventional surfactants such as NPEs, and biodegradable natural as an alternative surfactant to solve the toxicity problem of alkylphenol. Research into surfactants is also ongoing. (B. K. Jung, Kor. J. Ori. Med. Physiol. Pathol., 24, 837 (2010); K. Shweta, J. Nat. Prod. Plant Resour., 1, 24 (2011))

Accordingly, the present invention invents a phenyl group in the structure to replace the alkylphenol ethoxylate, and has excellent performance and is competitive in terms of price, and is an environmentally friendly dialkyl glycerol type nonionic surfactant and a method for effectively manufacturing the same. I wanted to.

Korean Registered Patent No. 10-1675787 (2016.11.15.)

B. K. Jung, Kor. J. Ori. Med. Physiol. Pathol., 24, 837 (2010) K. Shweta, J. Nat. Prod. Plant Resour., 1, 24 (2011)

Since nonionic surfactants are electrically neutral, they are less susceptible to electrolytes and have a characteristic of being easy to use because they are less affected by pH and are used in various household goods and industrial fields. However, a typical nonionic surfactant, alkylphenol ethoxylate (APE), does not decompose well in aquatic life, and unreacted alkylphenol (AP) affects environmental hormones, resulting in fish and other aquatic products. It accumulates in the human body. As a material that can replace this, a higher alcohol ethoxylate compound in which ethylene oxide is added to higher alcohol was developed, but environmentally, it is superior to alkylphenol ethoxylate, but has no linear molecular structure and no phenyl group in the molecule. In the limit.

Accordingly, an object of the present invention is to provide an environmentally friendly nonionic surfactant that exhibits excellent physical properties even without a phenyl group, and an efficient method for manufacturing the same.

In order to achieve the above object, the present invention provides a dialkyl glycerol-type nonionic surfactant represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

R ₁ and R ₂ are each linear or branched alkyl or linear or branched alkenyl having at least one double bond, wherein the total number of carbons in the straight chain and the side chain is 2 to 18, preferably 2 to 12 , More preferably 2 to 8, and most preferably 6. Also R ₁ And R ₂ may be the same or different; n is a constant of 2 to 20, preferably a constant of 5 to 15, m is a constant of 0 to 15, preferably a constant of 0 to 10.

In addition, the present invention, as shown in Scheme 1, a one-step reaction to prepare a compound represented by the formula (4) by reacting the compound represented by the formula (2) with the compound represented by the formula (3); And a two-step reaction for preparing a compound represented by the following formula 6 by reacting the compound represented by the following formula 4 and the compound represented by the following formula 5 prepared in the first step reaction; And a three-step reaction for preparing a compound represented by the following formula 1 by reacting a compound represented by the following formula 6 and a compound represented by the following formula 7 prepared in the two-step reaction; Provides a method for preparing an active agent.

The dialkylglycerol-type nonionic surfactant can be prepared according to the following Reaction Scheme 1.

[Scheme 1]

In Reaction Scheme 1, R ₁ and R _2, n, m are as defined above.

In a preferred embodiment, in the first step reaction, the compound of Formula 3 is reacted at a ratio of 0.9 to 1.5 mol per mol of the compound of Formula 2, and potassium carbonate or sodium carbonate, or a mixture thereof is 0.9 per mol of the compound of the Formula 2 ~ 1.5 moles can be used.

In addition, in a preferred embodiment, in the two-step reaction, any one or more bases of potassium hydroxide, sodium hydroxide, lithium hydroxide, and calcium hydroxide may be used in an amount of 0.001 to 0.1 mol per mol of the compound represented by Chemical Formula 4.

In addition, in a preferred embodiment, in the three-step reaction, any one or more bases of potassium hydroxide, sodium hydroxide, lithium hydroxide, and calcium hydroxide may be used in an amount of 0.001 to 0.1 mol per mol of the compound represented by Chemical Formula 6.

In addition, in a preferred embodiment, the first step reaction is carried out for 90 to 125 ° C., 6 to 24 hours, and the second step reaction and third step reaction can be carried out for 100 to 150 ° C., 6 to 24 hours.

In addition, in a preferred embodiment, it may be characterized in that a reaction solvent is not used in the first to third step reactions.

In addition, in a preferred embodiment, in the one-step reaction, an amine-based compound or an ammonium salt-based phase transfer catalyst may be used.

However, the technical problem to be achieved by the present invention is not limited to the problems mentioned above, and other problems not mentioned will be clearly understood by those skilled in the art from the following description.

The dialkyl glycerol-type nonionic surfactant according to the present invention realizes low surface tension and low critical micelle concentration (CMC), and combines high solubility in water and has excellent performance as a surfactant.

In addition, the present invention, since the nonionic surfactant does not contain a phenyl group, which is difficult to decompose, is environmentally friendly and has excellent cleaning power, it can replace the existing nonionic surfactant, alkylphenol ethoxylate, which is harmful to the environment.

Advantages and features of the present invention, and a method of achieving them will become apparent with reference to embodiments described below. However, the present invention is not limited to the embodiments disclosed below, but will be implemented in various different forms, and only the present embodiments allow the disclosure of the present invention to be complete, and common knowledge in the art to which the present invention pertains. It is provided to fully inform the person having the scope of the invention, and the present invention is only defined by the items described in the claims. The same reference numerals refer to the same components throughout the specification.

Hereinafter, the present invention will be described in detail.

The present invention provides a dialkyl glycerol type nonionic surfactant represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1, R ₁ and R ₂ are linear or branched alkyl or linear or branched alkenyl having at least one double bond, and the total number of carbon atoms in the straight and branched chains is 2 to 18, and R ₁ and R ₂ may be the same or different; n is a constant from 2 to 20, m is a constant from 0 to 15.

More preferably, in Chemical Formula 1, R ₁ and R ₂ have 2 to 12 carbons in the straight or branched chain or 2 or 12 carbons in the straight or branched chain having at least one double bond or a linear or branched alkyl having 2 to 12 carbons. Linear or branched alkenyl, the two may be the same or different; n is a constant from 5 to 15, m is a constant from 0 to 10.

 In another embodiment of the present invention, the present invention also, as shown in Scheme 1 below, by reacting a compound represented by Formula 2 with a compound represented by Formula 3 to prepare an intermediate alcohol that is a compound represented by Formula 4 1 Step reaction; And

A two-step reaction to prepare a compound represented by formula (6) by reacting the compound represented by formula (4) prepared in step 1 with a compound represented by formula (5); And

It provides a method for producing the non-ionic surfactant comprising a; three-step reaction to prepare a compound represented by formula (1) by reacting the compound represented by formula (6) and the compound represented by formula (7) prepared in the two-step reaction .

[Scheme 1]

The numbers below each formula in the above scheme refer to the formula number, and R ₁ and R ₂ , n, m are as defined above.

In step 1, the reaction in step 1 is a step of generating an intermediate alcohol represented by formula 4 by reacting an alcohol represented by formula 2 with glycidyl ether represented by formula 3.

In the first step reaction, the ratio of the alcohol of Formula 2 and the glycidyl ether of Formula 3 is preferably in the range of 1: 0.9 to 1.5 moles.

In the one-step reaction, a base may be used. The base used is an alkali metal compound, preferably a metal carbonate, more preferably potassium carbonate, sodium carbonate, and more preferably potassium carbonate. The base may be a solid base, and the amount of the base used may be 0.9 to 1.5 mol compared to 1 mol of the alcohol of Formula 2. When used at less than 0.9 molar ratio, the reaction is insignificant and the yield is not good, and when used at more than 1.5 molar ratio, there is no economic problem since it does not exhibit an effect equal to or higher than that added in an amount of 1.5 molar ratio or less.

In addition, the reaction may be carried out in the presence of a general organic solvent such as hexane, toluene, xylene, chloroform, but more preferably, no solvent is used. In the case of using a solvent, an additional process and additional cost for removing the used solvent occur, and in the present invention, it is more preferable not to use a solvent because the reaction proceeds without using a solvent.

In addition, in the one-step reaction of Reaction Scheme 1, a phase change catalyst may be included, but the phase change catalyst is not limited thereto, and may be an amine compound or an ammonium salt system, and preferably tetrabutyl ammonium bromide (TBAB). .

In preparing the formula 4, the reaction temperature is 90 ~ 125 ℃, the reaction time is preferably 6 ~ 24 hours. When the reaction temperature is lower or the reaction time is less than this, the reaction is not properly performed, and when the reaction temperature is higher than this or the reaction time is longer, the production of side reactants increases and the yield is lowered.

The intermediate alcohol of Chemical Formula 4 thus prepared may be separated and recovered from the reaction mixture using an appropriate separation means. As the separation means, conventional separation means such as extraction or distillation using a solvent may be used.

The two-step reaction of Scheme 1 is a step of preparing a compound of Formula 6 by reacting an intermediate alcohol of Formula 4 with an ethylene oxide compound of Formula 5. At this time, the number of moles of ethylene oxide reacting with Formula 4 is determined according to the number of moles to be added.

In addition, a base may also be used in the two-step reaction, and the amount of the base used may be used in a ratio of 0.001 to 0.1 mol per 1 mol of the intermediate alcohol of Formula 4, and preferably 0.01 to 0.05 mol. The base is an alkali metal compound, preferably a metal hydroxide, more preferably potassium hydroxide, sodium hydroxide, lithium hydroxide, calcium hydroxide, and more preferably potassium hydroxide. The base can be a solid base.

The reaction of the two-step reaction may be carried out in the presence of a general organic solvent such as hexane, toluene, xylene, and chloroform, but the use of a solvent is more preferable because the yield can be increased.

In preparing the formula (6), the reaction temperature is 100 to 150 ° C, and the reaction time is preferably 6 to 24 hours. More preferably, the reaction temperature is 120 to 130 ° C and the reaction time is 10 to 15 hours. When the reaction temperature is less than 100 ° C, the reactivity decreases and the reaction time increases. When the temperature exceeds 150 ° C, the probability of discoloration of the reactant increases, and side reactions increase. If the reaction time is less than 6 hr, it is difficult to control the exotherm, and if it is more than 24 hr, the side reaction increases, resulting in a lower product yield.

The three-step reaction of Scheme 1 is a step of reacting the compound of Formula 6 with the compound of Formula 7 to produce the compound of Formula 1. The number of moles of the formula (7) is determined according to the number of moles to be added.

In addition, the amount of the base used in the three-step reaction is 0.001 to 0.1 mol per mol of the compound of Formula 6, preferably 0.01 to 0.05 mol.

The base is an alkali metal compound, preferably a metal hydroxide, more preferably potassium hydroxide, sodium hydroxide, lithium hydroxide, calcium hydroxide, and more preferably potassium hydroxide. The base can be a solid base.

The three-step reaction may also be carried out in the presence of a general organic solvent such as hexane, toluene, xylene, and chloroform, but it is preferable in terms of yield not to use a solvent.

In preparing Formula 1, the reaction temperature is 100 to 150 ° C, and the reaction time is preferably 6 to 24 hours. More preferably, the reaction temperature is 120 to 130 ° C and the reaction time is 10 to 18 hours. When the reaction temperature is less than 100 ° C, the reactivity decreases and the reaction time increases. When the temperature exceeds 150 ° C, the probability of discoloration of the target increases, and side reactions increase. If the reaction time is less than 6 hr, it is difficult to control the exotherm, and if it is more than 24 hr, the side reaction increases, resulting in a lower product yield.

The three-step reaction may not be reacted depending on the properties to be imparted to the surfactant.

The reaction of steps 1 to 3 may be performed under a pressure of 0.5 to 5.0 atma, preferably 1 to 1.5 atma.

According to Reaction Scheme 1, a dialkyl glycerol type nonionic surfactant represented by Chemical Formula 1 can be obtained.

Hereinafter, specific embodiments of the present invention are presented. However, the examples described below are only for specifically illustrating or explaining the present invention, and the present invention is not limited thereto.

<Example 1>

1) Preparation of intermediate alcohol (C2-C6-OH)

1 mol of hexanol and 0.0625 mol of tetrabutyl ammonium bromide (TBAB) were added to a reactor equipped with a stirrer, heater, cooler, and thermometer. While heating to 100 ° C. and stirring, 1 mol of potassium carbonate was slowly added and stirred for 30 minutes. Ethyl glycidyl ether (1.4 mol) was slowly added dropwise to maintain the reaction temperature at 100 ° C using a dropping funnel, and then reacted at 100 ° C for 12 hours. After completion of the reaction, the product was added to a separatory funnel, 100 ml of toluene was added, 200 ml of water was added, stirred, separated into a water layer and an organic layer, and then the water layer was removed, and then 200 ml of water was added / stirring / removal of the water layer After repeating the procedure two more times, the organic layer was removed residual moisture using 10 g of magnesium sulfate. After distillation under reduced pressure, toluene was removed to obtain pure intermediate alcohol (1-ethoxy-3- (hexyloxy) propan-2-ol).

2) Nonionic surfactant production ((C2-C6-10EO production)

1-ethoxy-3- (hexyloxy) propan-2-ol 1 mol and 0.025 mol KOH as intermediate alcohols are added to the reactor equipped with a stirrer, heater, cooler, and thermometer, and the inside of the reactor is adjusted to 125 ° C. 10 mol of ethylene oxide (Ethylene oxide) was introduced into the reactor and reacted at 100 to 125 ° C. for 12 hours to obtain 1-ethoxy-3- (hexyloxy) propan-2-ol 10mole ethoxylate, a nonionic surfactant.

<Example 2>

1) Preparation of intermediate alcohol (C4-C4-OH)

Prepared in the same manner as in Example 1 except that butanol instead of hexanol and ethyl glycidyl ether were used in the first step reaction of Example 1, but butyl glycidyl ether was used. 1 , 3-bis (butoxy) propan-2-ol.

2) Nonionic surfactant production (C4-C4-10EO (PO) 2 production)

1 mol of 1,3-bis (butoxy) propan-2-ol and 0.01 mol of KOH are added to a reactor equipped with a stirrer, heater, cooler, and thermometer, and the inside of the reactor is adjusted to 125 ° C. After 10 mol of ethylene oxide was introduced into the reactor, the reaction was performed at 100-125 ° C for 12 hours, soaking was performed for 3 hours, and vacuum was performed at 125 ° C for 30 minutes to remove unreacted ethylene oxide. 2 mol of Propylene oxide was reacted at 125 ° C. for 2 to 4 hr to obtain 1,3-bis (butoxy) propan-2-ol alkoxylate, a nonionic surfactant.

<Example 3>

1) Preparation of intermediate alcohol (C6-C6-OH)

Prepared in the same manner as in Example 1, except that hexyl glycidyl ether was used instead of ethyl glycidyl ether in the first step reaction of Example 1, 1,3-bis (hexyloxy ) propan-2-ol.

2) Nonionic surfactant production ((C6-C6-10EO production)

It was prepared in the same manner as in Example 1, except that the 1,3-bis (hexyloxy) propan-2-ol was used in the preparation of the nonionic surfactant of Example 1.

<Example 4>

1) Preparation of intermediate alcohol (C8-C8-OH)

Prepared in the same manner as in Example 1, except that octanol was used instead of hexanol and octyl glycidyl ether was used instead of ethyl glycidyl ether in the first step reaction of Example 1 1,3-bis (octyloxy) propan-2-ol was obtained.

2) Nonionic surfactant production ((C8-C8-8EO production)

The same method as in Example 1, except that 1,3-bis (octyloxy) propan-2-ol was used and 8 moles of ethylene oxide was used in the process of preparing the nonionic surfactant of Example 1 Was prepared.

<Comparative Example 1> polyoxyethylene lauryl ether 9

As a representative nonionic surfactant on the market, Polyoxyethylene lauryl ether 9 was purchased from Sigma Aldrich and used.

<Comparative Example 2> Oleyl dioleylamidoamine methosulfate

As a representative cationic surfactant on the market, Oleyl dioleylamidoamine methosulfate was purchased from Southeast Synthesis and used.

<Comparative Example 3> 96% dodecylbenzene sulfonic acid

As a representative commercially available anionic surfactant, Dodecylbenzene sulfonic acid 96% was purchased from Sigma Aldrich and used.

<Comparative Example 4> SH-8

SH-8, a typical silicone surfactant, was synthesized and used. The synthesis was carried out using Heptatrimethylsiloxane and Allyl Alcohol Ethoxylate in platinum catalyst, and Heptatrimethylsiloxane and allyl alcohol platinum catalyst were purchased from Sigma Aldrich.

<Comparative Example 5> Nonylphenol ethoxylate

Nonylphenol ethoxylate 10, a typical aryl-based nonionic surfactant on the market, was purchased and used at Hannong Chemical.

<Experimental Example 1>

The compounds obtained according to Examples and Comparative Examples 1 to 4 were evaluated in the following manner.

1. Surface tension measurement

The surface tension was measured by making a 1% aqueous solution using a platinum ring using KRUSS PROCESSOR Tensionmeter K100.

2. CMC measurement

CMC was determined by measuring the surface tension according to the molar concentration of each component using a platinum ring using KRUSS 'PROCESSOR Tensionmeter K100.

The surface tension and CMC are as shown in Table 1 below, and the lower the value, the better the performance.

Surface tension (mN / m) CMC (mmol / L) Example 1 30.45 4.87 Example 2 29.97 5.92 Example 3 26.07 0.45 Example 4 25.64 0.01 Comparative Example 1 31.13 0.21 Comparative Example 2 37.24 5.86 Comparative Example 3 32.25 6.20 Comparative Example 4 21.50 0.18 Comparative Example 5 32.01 0.06

As a result of <Table 1>, the nonionic surfactant according to the present invention exhibits a lower surface tension than typical nonionic, cationic, anionic, and nonylphenol surfactants currently on the market. In addition, the critical micelle concentration (CMC) is lower than that of commercially available cations or anionic surfactants in Examples 1 to 4, and in particular, in Example 4, it is lower than that of Comparative Examples 1 to 5.

<Experimental Example 2>

The compounds obtained according to the Examples and Comparative Examples 1 to 4 were tested for cleaning power in the following manner. The used device used a Terg-O-Tometer by imitating a vortex-type washing machine, and after introducing the pollutant measuring the reflectance into the used device, the cleaning agent of the same concentration (1.33 g / L) was added (30 ± 2) ℃. After washing the water for 10 minutes at a stirring speed of (120 ± 5) r / min, after washing for 2 minutes every 3 minutes, the reflectance was measured and the cleaning power was evaluated. The higher the value, the better the cleaning power.

exam
Item Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Washing power 8.0 6.4 52.9 24.8 44.4 3.5 37.5 37.4 51.3

The cleaning power of the compounds obtained according to Examples 1 to 4 varies depending on the number of carbon atoms of the hydrophobic groups to be added, but generally, the cleaning power is higher than the typical cationic surfactants currently on the market, especially in the case of Example 3. It was confirmed that it shows a very excellent cleaning power than the surfactant.

Therefore, the nonionic surfactant according to the present invention does not contain an alkylphenol ethoxylate (APE), and is environmentally friendly and has a cleaning power equal to or greater than that of a commercially available surfactant, and thus APE-based nonionic surfactant. Will be able to replace

One embodiment of the present invention described above should not be construed as limiting the technical spirit of the present invention. The scope of protection of the present invention is limited only by the items described in the claims, and a person having ordinary knowledge in the technical field of the present invention can improve and modify the technical spirit of the present invention in various forms. Therefore, such improvements and modifications will fall within the protection scope of the present invention as long as it is apparent to those skilled in the art.

Claims (11)

In the nonionic surfactant,
Dialkyl glycerol type nonionic surfactant, characterized in that it comprises a compound represented by the formula (1).
[Formula 1]

In Chemical Formula 1,
R ₁ and R ₂ are each linear or branched alkyl or linear or branched alkenyl having at least one double bond, wherein the total number of carbons in the straight chain and the side chain is 2 to 18, and the two are the same or different. Can; n is a constant from 2 to 20, m is a constant from 0 to 15. According to claim 1,
R ₁ and R ₂ in Formula 1 are linear or branched alkyl or linear or branched alkenyl having at least one double bond, respectively, having 2 to 12 carbons in straight and branched chains, and R ₁ and R ₂ may be the same or different; n is a constant of 5 to 15, m is a dialkylglycerol type nonionic surfactant, characterized in that a constant of 0 to 10. According to claim 1,
R ₁ and R ₂ in Formula 1 are linear or branched alkyl or linear or branched alkenyl having at least one double bond, and have 2 to 8 carbon atoms in straight and branched chains, and R ₁ and R ₂ may be the same or different; n is a constant of 5 to 15, m is a dialkylglycerol type nonionic surfactant, characterized in that a constant of 0 to 10. According to claim 1,
R ₁ and R ₂ of Formula 1 are linear or branched alkyl or linear or branched alkenyl having at least one double bond, respectively, having 6 carbons in straight and branched chains, and R ₁ and R ₂ are May be the same or different; n is a constant of 8 to 10, m is a dialkyl glycerol-type nonionic surfactant, characterized in that one. A one step reaction to prepare a compound represented by the following formula 4 by reacting a compound represented by the following formula 2 with a compound represented by the following formula 3; And
A two-step reaction to prepare a compound represented by the following formula 6 by reacting a compound represented by the following formula 4 and a compound represented by the following formula 5 prepared in the first step reaction; And
Dialkylglycerol-type nonionic surfactant comprising; a three-step reaction to prepare a compound represented by the formula (1) by reacting the compound represented by the formula (6) and the compound represented by the formula (7) prepared in the two-step reaction Method of manufacturing.

In Chemical Formulas 1 to 7,
R ₁ and R ₂ are each linear or branched alkyl or linear or branched alkenyl having at least one double bond, wherein the total number of carbons in the straight chain and the side chain is 2 to 18, and the two are the same or different. Can; n is a constant from 2 to 20, m is a constant from 0 to 15. The method of claim 5,
In the first step reaction, a compound of Formula 3 is reacted at a ratio of 0.9 to 1.5 moles per mole of the compound of Formula 2, and potassium carbonate or sodium carbonate or a mixture thereof is used at 0.9 to 1.5 moles per mole of the compound of Formula 2 Method for producing a dialkyl glycerol-type nonionic surfactant. The method of claim 5,
In the two-step reaction, a method for producing a dialkylglycerol-type nonionic surfactant, characterized in that 0.001 to 0.1 mol per mol of the compound represented by Formula 4 is used in any one or more bases of potassium hydroxide, sodium hydroxide, lithium hydroxide, and calcium hydroxide. The method of claim 5,
In the three-step reaction, a method for producing a dialkylglycerol-type nonionic surfactant, characterized in that 0.001 to 0.1 mol per mol of the compound represented by Formula 6 is used in any one or more bases of potassium hydroxide, sodium hydroxide, lithium hydroxide, and calcium hydroxide. The method of claim 5,
The first step reaction is carried out for 90 ~ 125 ℃, 6 ~ 24 hours, the second step reaction and the third step reaction is 100 ~ 150 ℃, dialkyl glycerol type nonionic, characterized in that carried out for 6 ~ 24 hours Method for the preparation of surfactants. The method of claim 5,
Method of producing a dialkyl glycerol-type nonionic surfactant, characterized in that a reaction solvent is not used in the first to third reactions. The method of claim 5,
In the one-step reaction, a method for producing a dialkylglycerol-type nonionic surfactant, characterized in that an amine-based compound or an ammonium salt-based phase transfer catalyst is used.