JPH09286791A - Production of basic amino acid salt of branched dimerized alkyl phosphate - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce the subject high-quality compound useful as cosmetics, medicines, etc., by phosphorylating a branched dimerized alcohol, providing a branched dimerized alkyl phosphate, then neutralizing the resultant compound with a basic amino acid and depositing a crystal at a specific temperature in a ketonic solvent. SOLUTION: A branched dimerized alcohol (e.g. 2-hexyldecanol) is phosphorylated with polyphosphoric acid, etc., to provide a branched dimerized alkyl phosphate (e.g. 2-hexyldecyl phosphate), which is then dissolved in ethanol. A powder of a basic amino acid such as argninine, histidine or lysine is then added to neutralize the branched dimerized alkyl phosphate. The neutralized compound is subsequently added to a ketonic solvent such as acetone or methyl ethyl ketone to deposit and separate a crystal of a basic amino acid salt of the branched dimerized alkyl phosphate at 0-20 deg.C temperature. The resultant high-quality basic amino acid salt of the branched dimerized alkyl phosphate can be used for fragrant cosmetics, cosmetics, medicines, etc., and is good in odor and hue.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a method for producing a basic amino acid salt of a phosphoric acid ester of a branched dimerized alcohol (hereinafter referred to as “branched dimerized alkyl phosphoric acid”). More specifically, it relates to a method for producing a branched dimerized alkyl phosphate basic amino acid salt which is excellent in quality such as color and odor and has good crystallinity.

[0002]

BACKGROUND OF THE INVENTION It has been known since the 19th century that phosphoric acid esters of organic hydroxy compounds can be obtained by reacting hydroxyl compounds with phosphorylating agents such as phosphorus pentoxide and phosphoryl trichloride. Salts such as alkali metal salts and alkanolamine salts are used in a wide range of fields as detergents, fiber treatment agents, emulsifiers, rust preventives, liquid ion exchangers, pharmaceuticals and the like. Among them, the phosphoric acid ester of a branched dimerized alcohol obtained by the Guerbet reaction has a melting point lower than that of a phosphoric acid ester of a linear alcohol, and has a large hydrophobic property, so that an electrophotographic developer (DE2224563, Gevaert
-Agfa NV (1972)), a precursor of biomembrane analogues (Deroo,
Pool. W., Chem. Phys. Lipids., 16 (1), 60-70 (197
6)), hair rinse agents (Japanese Patent Laid-Open No. 56-77218), and other uses are known.

Further, basic amino acid salts of alkyl phosphoric acid, particularly basic amino acid salts such as arginine salt of branched dimerized alkyl phosphoric acid, form a stable gel regardless of the type of oil, and are therefore used as cosmetic bases. A wide range of applications are expected (JP-A-58-180496 and JP-A-63-122775).
Issue).

As described above, alkyl phosphate salts, especially branched dimerized alkyl phosphates, are important as base components for cosmetics, detergents, etc., and therefore need not be colored or odorous. Therefore, various methods for purifying alkyl phosphates or salts thereof have been conventionally known.

Conventionally, as a method for purifying an alkyl phosphoric acid ester or a salt thereof, (1) a method of deodorizing an acidic phosphoric acid ester and then adding polyphosphoric acid (Japanese Patent Publication No. 60-41673).
(2) A method of removing arsenic and the like by adding an adsorbent to an alkyl phosphate ester (Japanese Patent Publication No. 62-45874).
(3) A method of precipitating and separating an alkyl phosphate sodium salt or potassium salt from an organic solvent (Japanese Patent Publication No.
-41674), (4) Unreacted orthophosphoric acid is extracted and removed from the alkyl phosphate ester into the aqueous layer using hydrocarbon and lower alcohol-water (JP-B-63-47715), or further carbonization is carried out. Method of removing lower alcohol and water mixed in hydrogen layer by azeotropic distillation (Japanese Patent Publication No. 2-46040) and recrystallizing or topping, (5) alkyl phosphate using hydrocarbon and lower alcohol-water Method for extracting and removing nonionic compounds from ester salts (Japanese Patent Publication No. 3-27558), (6) Method for removing excess phosphoric acid from alkylphosphoric acid by electrodialysis (Japanese Patent Laid-Open No. 61-129189), (7)
A method has been proposed in which an alkyl phosphonate arginine salt is precipitated from methanol and separated (JP-A-58-180496).

However, in the branched dimerized alkyl phosphates, unreacted branched dimerized alcohols, impurities in the branched dimerized alcohols, coloring components, and non-ionic substances such as hydrocarbons by-produced during phosphorylation. Since it contains a volatile substance, especially by-product hydrocarbons have an adverse effect on quality such as color and odor, it is a problem when used as a base component of cosmetics. This nonionic substance cannot be removed by any method other than 5). Although method (5) is a method for removing nonionic substances, it cannot be applied to this because basic amino acid salts such as branched dimerized alkylphosphoric acid arginine salts cannot be subjected to solution extraction. There is a problem that you cannot do it. Therefore, a method of precipitating a branched dimerized alkyl phosphate basic amino acid salt from a solvent as in method (7) may be considered, but method (7) could not remove nonionic substances. .

Therefore, the inventors of the present invention added the crude branched dimerized alkylphosphoric acid basic amino acid salt after phosphorylation and neutralization to the ketone-based solvent to prepare crystals of the branched dimerized alkylphosphoric acid basic amino acid salt. It was found that non-ionic substances such as hydrocarbons can be efficiently removed by precipitating and separating, and the content of non-ionic substances can be suppressed to 1% by weight or less. Wishhei 7-
No. 118218). However, in this method, the aldol condensation of the ketone solvent occurs due to the interaction between the used ketone solvent and the branched dimerized alkylphosphoric acid basic amino acid salt. For example, when acetone is used, mesityl oxide, methyl ethyl ketone When used, dimers such as 5-methyl-4-hepten-3-one are by-produced, and these dimers serve as odor-causing substances, and the odor is reduced to a level that is still sufficiently satisfactory. Didn't.

Therefore, the object of the present invention is to reduce the dimer of the ketone solvent which causes the odor, and cosmetics, cosmetics,
An object of the present invention is to provide a method for producing a high-quality branched dimerized alkyl phosphate basic amino acid salt that can be used in medicines and the like.

[0009]

Under the circumstances, as a result of intensive studies, the present inventors have found that crystal precipitation with a ketone solvent is carried out within a specific temperature range, thereby sufficiently satisfying in terms of color, odor, etc. It was found that a high-quality branched dimerized alkylphosphoric acid basic amino acid salt having good crystallinity can be obtained, and the present invention has been completed.

That is, the present invention comprises the following steps (a) to
The present invention provides a method for producing a branched dimerized alkyl phosphate basic amino acid salt, which comprises performing (c). Step (a): Step of phosphorylating branched dimerized alcohol to obtain branched dimerized alkyl phosphoric acid Step (b): Neutralization of crude branched dimerized alkyl phosphoric acid obtained in step (a) with basic amino acid Step (c): The neutralized product obtained in step (b) is added to a ketone solvent, and crystals of a branched dimerized alkyl phosphate basic amino acid salt are precipitated at a temperature of 0 to 20 ° C. for separation. Process

[0011]

Embodiments of the present invention will be described below in detail.

Step (a): This step is a step of phosphorylating a branched dimerized alcohol to obtain a branched dimerized alkylphosphoric acid. The branched dimerized alcohol used in this step is
Obtained by the Guerbet reaction, but with 4 to 1 carbon atoms
Those obtained from an alcohol having 8 or 6 to 12 carbon atoms are preferable. Specific examples include 2-butyloctanol, 2-hexyldecanol, 2-heptylundecanol, 2-octyldodecanol, 2-decyltetradecanol, and 2-dodecylhexadecanol. Among them, 2-hexyldecanol, 2-heptyl undecanol and 2-octyl dodecanol are preferred. These branched dimerized alcohols can be used alone or in combination of two or more kinds.

As the phosphorylation method in this step, for example, a method of hydrolyzing monophosphorodichloridate obtained by reacting a branched dimerized alcohol with phosphorus oxychloride (K. Sasse: Methoden der Ofganischen) C
hemie, Vol. 12/2, pp. 163-164, and JP-A-50-64226), a method in which a certain amount of water is added to a branched dimer alcohol in advance, and then phosphorus pentoxide is reacted (Japanese Patent Publication No.
41-14416), a method of reacting a branched dimerized alcohol with orthophosphoric acid and phosphorus pentoxide (Japanese Patent Publication No. 42-6730), a method of reacting a branched dimerized alcohol with condensed phosphoric acid (polyphosphoric acid) (AK Nelson et al., Inorg.
Chem., 2, 775 (1963), FB Clarke et al., J. Amer.
Chem. Soc., 88, 4401 (1966), and JP-B-43-26492) and the like, and any method may be used.

For example, when the phosphorylation reaction is carried out using polyphosphoric acid, the polyphosphoric acid used has a concentration of 110 to 120%, particularly 112 to 116% in terms of orthophosphoric acid, and the reaction rate, operability and alkyl It is preferable in terms of suppressing the decomposition of phosphoric acid. The amount used is 1 for branched dimerized alcohol.
-10 equivalents, especially 2-3 equivalents are preferred.

The phosphorylation reaction with polyphosphoric acid may be carried out without using a solvent, but in order to improve operability, a straight chain or branched saturated hydrocarbon or saturated cyclic hydrocarbon having 4 to 8 carbon atoms, For example, n-pentane, n-hexane, cyclohexane or the like may be used as a solvent. The phosphorylation reaction is carried out at 60 to 100 ° C for 1 to 16 hours, and then 1 to 30% by weight of water is added to the reaction mixture to give 1 to 20 at 60 to 100 ° C.
The hydrolysis reaction is performed for a time. The reaction mixture is allowed to stand to separate the layers in a short time, and the solvent is distilled off from the light liquid layer under normal pressure or reduced pressure to obtain an acidic crude branched dimerized alkylphosphoric acid.

Step (b): This step is a step of neutralizing the crude branched dimerized alkyl phosphate obtained in step (a) with a basic amino acid. Examples of the basic amino acid used as the neutralizing agent include lysine, arginine, histidine and the like, and arginine is particularly preferable from the viewpoint of easy handling and cost. These basic amino acids can be used as a powder as they are or as an aqueous solution, but it is preferable to use them as a powder because of the ease of purification.

Neutralization with a basic amino acid is carried out, for example, by using the acidic crude branched dimerized alkyl phosphate 1 obtained in step (a).
It is carried out by adding 50 to 500 parts by weight of an appropriate solvent to 00 parts by weight, and then adding 0.5 to 3 equivalents of the basic amino acid to the acid value of the crude branched dimerized alkylphosphoric acid. As the solvent, in addition to alcohol solvents such as methanol, ethanol and propanol, ether solvents such as tetrahydrofuran and halogenated hydrocarbon solvents such as dichloromethane may be used as long as they contain a few% of water. it can. The reaction temperature of the neutralization reaction is preferably 70 to 80 ° C, and the reaction time is preferably 5 to 10 hours.

Step (c): In this step, the neutralized product obtained in step (b) is added to a ketone solvent to form crystals of a branched dimerized alkylphosphoric acid basic amino acid salt at a temperature of 0 to 20 ° C. It is a step of depositing and separating.

The temperature at which crystals of the branched dimerized alkylphosphoric acid basic amino acid salt are precipitated by adding the neutralized product to the ketone solvent is 0 to 20 ° C, preferably 0 to 10 ° C. If this temperature is lower than 0 ° C, the elution efficiency of impurities into the ketone solvent is poor, and if it is higher than 20 ° C, the ketone solvent causes aldol condensation due to the interaction with the branched dimerized alkyl phosphate basic amino acid salt. As a result, dimers such as mesityl oxide and 5-methyl-4-hepten-3-one are likely to be formed, and the target product having a sufficiently good odor cannot be obtained.

As the ketone solvent used here,
Acetone, methyl ethyl ketone, etc. may be mentioned, but acetone is particularly preferable because of its good crystallinity and ease of drying.
The amount of the ketone-based solvent is preferably 1 to 10 times, and more preferably 2 to 5 times the amount of the crude branched dimerized alkyl phosphate basic amino acid salt.

Crystals precipitated in the ketone solvent are taken out by a method such as filtration and dried under normal pressure or reduced pressure to obtain a purified branched dimerized alkyl phosphate basic amino acid salt. It is desirable to repeatedly perform washing and separation with a ketone solvent at 20 ° C. to reduce the dimer content of the ketone solvent to 500 ppm or less, preferably 200 ppm or less, and particularly preferably 150 ppm or less.

The thus-obtained branched dimerized alkylphosphoric acid basic amino acid salt is excellent in quality such as color and odor and can be suitably used for applications such as cosmetics.

[0023]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the invention is limited thereto.

Example 1 Commercially available 2-hexyldecanol (Nene Ecole 160BRA manufactured by Shin Nippon Rika Co., Ltd.) 380 g (1.52 mol) and 270 g (3.20 mol) of 116% polyphosphoric acid were reacted in 380 g of hexane at 70 ° C. for 3 hours. It was To this reaction solution was added 168g of water and the mixture was heated at
A hydrolysis reaction was performed for a period of time to decompose excess pyrophosphoric acid. In order to remove excess phosphoric acid, this reaction solution was allowed to stand still for layer separation, and the solvent component was distilled off from the light extraction liquid to obtain acidic crude 2-hexyldecyl phosphoric acid. The content of mesityl oxide in this crude 2-hexyldecylphosphoric acid was 0 ppm. The hue of this material was Klett 32.

An equal amount of ethanol was added to this acidic crude 2-hexyldecylphosphoric acid to dissolve it at 60 ° C., 265 g of arginine powder was added, and the mixture was neutralized at 70 ° C. for 6 hours. The reaction solution became transparent. The neutralized reaction product was added to acetone in an amount three times that of crude 2-hexyldecylphosphoric acid, and the mixture was stirred at 10 ° C. for 1 hour to produce white crystals. The content of mesityl oxide in the crystal was 1100 ppm. The crystals were taken out by filtration, further washed with 3 volumes of acetone at 10 ° C. three times, and dried under reduced pressure for 16 hours to obtain a purified product. Obtained 2-
The content of mesityl oxide in the arginine hexyldecylphosphate salt was 75 ppm. The hue of this substance was Klett 10, and the odor sensory evaluation was good.

Example 2 Using the same 2-hexyldecanol as in Example 1, phosphorylation and neutralization were carried out in the same manner as in Example 1 to obtain a neutralized reaction product. The obtained neutralization reaction product was added to acetone in an amount 3 times that of crude 2-hexyldecylphosphoric acid, and the mixture was stirred at 20 ° C. for 1 hour to produce white crystals. The content of mesityl oxide in the crystal was 2000 ppm. The crystals were taken out by filtration, washed with 3 times amount of acetone at 20 ° C. three times, and dried under reduced pressure for 16 hours to obtain a purified product. The content of mesityl oxide in the obtained arginine salt of 2-hexyldecylphosphate was 110 ppm. The hue of this substance was Klett 15, and the odor sensory evaluation was good.

Example 3 Using the same 2-hexyldecanol as in Example 1, phosphorylation and neutralization were carried out in the same manner as in Example 1 to obtain a neutralized reaction product. The obtained neutralization reaction product was added to acetone in an amount 3 times that of crude 2-hexyldecylphosphoric acid, and the mixture was stirred at 0 ° C. for 1 hour to produce white crystals. The content of mesityl oxide in the crystals was 800 ppm. The crystals were taken out by filtration, further washed with 3 times amount of acetone at 0 ° C. three times, and dried under reduced pressure for 16 hours to obtain a purified product. 2 obtained
-The content of mesityl oxide in arginine hexyldecylphosphate was 65 ppm. Further, the hue of this substance was Klett 9, and the odor sensory evaluation was good.

Example 4 380 g (1.40 mol) of commercially available 2-heptyl undecanol (Diadol 18GT manufactured by Mitsubishi Chemical Corporation) and 116% polyphosphoric acid
265 g (3.16 mol) was reacted in 380 g of hexane at 70 ° C for 3 hours. Water (156 g) was added to this reaction solution, and a hydrolysis reaction was carried out at 70 ° C. for 16 hours to decompose excess pyrophosphoric acid. In order to remove excess phosphoric acid, the reaction solution was allowed to stand still and separated into layers,
The solvent was distilled off from the light extraction liquid to obtain acidic crude 2-heptylundecylphosphoric acid. The content of mesityl oxide in this crude 2-heptylundecylphosphoric acid was 0 ppm. The hue of this material was Klett 30.

An equal amount of ethanol was added to the crude acidic 2-heptylundecylphosphoric acid to dissolve it at 60 ° C., 244 g of arginine powder was added, and the mixture was neutralized at 70 ° C. for 6 hours. The reaction solution became transparent. This neutralized reaction product was added to acetone in an amount 3 times that of crude 2-heptylundecylphosphoric acid, and the mixture was stirred at 10 ° C. for 1 hour to produce white crystals. The content of mesityl oxide in the crystal was 1000 ppm. The crystals were filtered out and further washed with 3 volumes of acetone at 10 ° C.
After washing twice, it was dried under reduced pressure for 16 hours to obtain a purified product. The content of mesityl oxide in the obtained 2-heptylundecylphosphoric acid arginine salt was 80 ppm. The hue of this substance was Klett 11, and the sensory evaluation of odor was good.

Example 5 380 g (1.27 mol) of commercially available 2-octyldodecanol (Kalcoal 200GD manufactured by Kao Corporation) and 241 g (2.8 g of 116% polyphosphoric acid)
6 mol) was reacted in 380 g of hexane at 70 ° C. for 3 hours.
142 g of water was added to this reaction solution, and a hydrolysis reaction was performed at 70 ° C. for 16 hours to decompose excess pyrophosphoric acid. In order to remove excess phosphoric acid, this reaction solution was allowed to stand still for layer separation, and the solvent was distilled off from the light extraction liquid to obtain acidic crude 2-octyldodecylphosphoric acid. The content of mesityl oxide in this crude 2-octyldodecylphosphoric acid was 0 ppm. The hue of this material was Klett 28.

An equal amount of ethanol was added to the acidic crude 2-octyldodecylphosphoric acid to dissolve it at 60 ° C., 243 g of arginine powder was added, and the mixture was neutralized at 70 ° C. for 6 hours. The reaction solution became transparent. This neutralized reaction product was added to acetone in an amount 3 times that of crude 2-octyldodecylphosphoric acid, and the mixture was stirred at 10 ° C. for 1 hour to produce white crystals. The content of mesityl oxide in the crystal was 1050 ppm. The crystals were taken out by filtration, further washed with 3 volumes of acetone at 10 ° C. three times, and dried under reduced pressure for 16 hours to obtain a purified product. The content of mesityl oxide in the obtained 2-octyldodecylphosphoric acid arginine salt was 70 ppm. Further, the hue of this substance was Klett 9, and the odor sensory evaluation was good.

Example 6 Using the same 2-hexyldecanol as in Example 1, phosphorylation was carried out in the same manner as in Example 1 to obtain acidic crude 2-hexyldecylphosphoric acid. The content of mesityl oxide in this crude 2-hexyldecylphosphoric acid was 0 ppm. The hue of this material was Klett 32.

An equal amount of ethanol was added to this acidic crude 2-hexyldecylphosphoric acid to dissolve it at 60 ° C., 236 g of histidine powder was added, and the mixture was neutralized at 70 ° C. for 6 hours. The reaction solution became transparent. The neutralized reaction product was added to acetone in an amount three times that of crude 2-hexyldecylphosphoric acid, and the mixture was stirred at 10 ° C. for 1 hour to produce white crystals. The content of mesityl oxide in the crystals was 1200 ppm. The crystals were taken out by filtration, further washed with 3 volumes of acetone at 10 ° C. three times, and dried under reduced pressure for 16 hours to obtain a purified product. Obtained 2-
The content of mesityl oxide in the histidine salt of hexyldecyl phosphate was 80 ppm. The hue of this substance was Klett 10, and the odor sensory evaluation was good.

Example 7 Using the same 2-hexyldecanol as in Example 1, phosphorylation was carried out in the same manner as in Example 1 to obtain acidic crude 2-hexyldecylphosphoric acid. The content of 5-methyl-4-hepten-3-one in this crude 2-hexyldecylphosphate was 0 pp.
m. The hue of this material was Klett 32.

An equal amount of ethanol was added to this acidic crude 2-hexyldecylphosphoric acid to dissolve it at 60 ° C., 265 g of arginine powder was added, and the mixture was neutralized at 70 ° C. for 6 hours. The reaction solution became transparent. When this neutralized reaction product was added to methyl ethyl ketone in an amount 3 times that of crude 2-hexyldecylphosphoric acid and stirred at 10 ° C. for 1 hour, white crystals were formed. The content of 5-methyl-4-hepten-3-one in the crystal was 860 ppm. The crystals were taken out by filtration, washed with 3 times the amount of methyl ethyl ketone at 10 ° C. three times, and dried under reduced pressure for 16 hours to obtain a purified product. 5-Methyl-4-heptene-3-in the obtained arginine salt of 2-hexyldecylphosphate
The content of on was 40 ppm. The hue of this substance was Klett 10, and the odor sensory evaluation was good.

Comparative Example 1 Using the same 2-hexyldecanol as in Example 1, phosphorylation and neutralization were carried out in the same manner as in Example 1 to obtain a neutralized reaction product. The resulting neutralized reaction product was added to acetone in an amount 3 times that of crude 2-hexyldecylphosphoric acid, and the mixture was stirred at 25 ° C. for 1 hour to produce white crystals. The content of mesityl oxide in the crystal was 5000 ppm. The crystals were taken out by filtration, further washed with 3 times amount of acetone at 25 ° C. three times, and dried under reduced pressure for 16 hours to obtain a purified product. The content of mesityl oxide in the obtained 2-hexyldecylphosphoric acid arginine salt was 600 ppm. In addition, the hue of this substance was Klett 25, and an offensive odor was recognized by sensory evaluation of odor.

Comparative Example 2 Using the same 2-hexyldecanol as in Example 1, phosphorylation was carried out in the same manner as in Example 1 to obtain acidic crude 2-hexyldecylphosphoric acid. The content of mesityl oxide in this crude 2-hexyldecylphosphoric acid was 0 ppm. The hue of this material was Klett 32.

An equal amount of ethanol was added to this acidic crude 2-hexyldecylphosphoric acid to dissolve it at 60 ° C., 236 g of histidine powder was added, and the mixture was neutralized at 70 ° C. for 6 hours. The reaction solution became transparent. This neutralized reaction product was added to acetone in an amount three times that of crude 2-hexyldecylphosphoric acid, and the mixture was stirred at 25 ° C. for 1 hour to produce white crystals. The content of mesityl oxide in the crystal was 7,000 ppm. The crystals were taken out by filtration, further washed with 3 times amount of acetone at 25 ° C. three times, and dried under reduced pressure for 16 hours to obtain a purified product. Obtained 2-
The content of mesityl oxide in the hexyldecylphosphate histidine salt was 680 ppm. In addition, the hue of this substance was Klett 26, and a sensory evaluation of odor showed offensive odor.

Comparative Example 3 Using the same 2-hexyldecanol as in Example 1, phosphorylation was carried out in the same manner as in Example 1 to obtain acidic crude 2-hexyldecylphosphoric acid. The content of mesityl oxide in this crude 2-hexyldecylphosphoric acid was 0 ppm. The hue of this material was Klett 32.

An equal amount of ethanol was added to the acidic crude 2-hexyldecylphosphoric acid to dissolve it at 60 ° C., 276 g of triethanolamine was added, and the mixture was neutralized at 70 ° C. for 6 hours. The reaction solution became transparent. The neutralized reaction product was added to acetone in an amount three times that of crude 2-hexyldecylphosphoric acid, and the mixture was stirred at 10 ° C. for 1 hour to give a cloudy liquid. The content of mesityl oxide in this substance was 800 ppm. It could not be purified with acetone because it did not crystallize. The hue of this material was Klett 16.

Comparative Example 4 Using the same 2-hexyldecanol as in Example 1, phosphorylation was carried out in the same manner as in Example 1 to obtain acidic crude 2-hexyldecylphosphoric acid. The content of mesityl oxide in this crude 2-hexyldecylphosphoric acid was 0 ppm. The hue of this material was Klett 32.

An equal amount of ethanol was added to this acidic crude 2-hexyldecylphosphoric acid to dissolve it at 60 ° C., 276 g of triethanolamine was added, and the mixture was neutralized at 70 ° C. for 6 hours. The reaction solution became transparent. The neutralized reaction product was added to acetone in an amount 3 times that of crude 2-hexyldecylphosphoric acid, and the mixture was stirred at 25 ° C. for 1 hour to give a cloudy liquid. The content of mesityl oxide in this substance was 5400 ppm. It could not be purified with acetone because it did not crystallize. The hue of this material was Klett 27.

Comparative Example 5 Using the same 2-hexyldecanol as in Example 1, phosphorylation was carried out in the same manner as in Example 1 to obtain acidic crude 2-hexyldecylphosphoric acid. The content of mesityl oxide in this crude 2-hexyldecylphosphoric acid was 0 ppm. The hue of this material was Klett 32.

An equal amount of ethanol was added to this acidic crude 2-hexyldecylphosphoric acid to dissolve it at 60 ° C., and 92.9 g of monoethanolamine was added to neutralize at 70 ° C. for 6 hours. The reaction solution became transparent. The neutralized reaction product was added to acetone in an amount three times that of crude 2-hexyldecylphosphoric acid, and the mixture was stirred at 10 ° C. for 1 hour to give a cloudy liquid. The content of mesityl oxide in this substance was 1500 ppm. It could not be purified with acetone because it did not crystallize.
The hue of this material was Klett 10.

Comparative Example 6 Using the same 2-hexyldecanol as in Example 1, phosphorylation was carried out in the same manner as in Example 1 to obtain acidic crude 2-hexyldecylphosphoric acid. The content of mesityl oxide in this crude 2-hexyldecylphosphoric acid was 0 ppm. The hue of this material was Klett 32.

An equal amount of ethanol was added to this acidic crude 2-hexyldecylphosphoric acid to dissolve it at 60 ° C., and 92.9 g of monoethanolamine was added and neutralized at 70 ° C. for 6 hours. The reaction solution became transparent. The neutralized reaction product was added to acetone in an amount 3 times that of crude 2-hexyldecylphosphoric acid, and the mixture was stirred at 25 ° C. for 1 hour to give a cloudy liquid. The content of mesityl oxide in this substance was 6500 ppm. It could not be purified with acetone because it did not crystallize. The hue of this material was Klett 24.

Comparative Example 7 Using the same 2-hexyldecanol as in Example 1, phosphorylation was carried out in the same manner as in Example 1 to obtain acidic crude 2-hexyldecylphosphoric acid. The content of 5-methyl-4-hepten-3-one in this crude 2-hexyldecylphosphate was 0 pp.
m. The hue of this material was Klett 32.

An equal amount of ethanol was added to this acidic crude 2-hexyldecylphosphoric acid to dissolve it at 60 ° C., 265 g of arginine powder was added, and the mixture was neutralized at 70 ° C. for 6 hours. The reaction solution became transparent. The neutralized reaction product was added to methyl ethyl ketone in an amount 3 times that of crude 2-hexyldecylphosphoric acid, and the mixture was stirred at 25 ° C. for 1 hour to produce white crystals. The content of 5-methyl-4-hepten-3-one in the crystals was 4500 ppm. These crystals were taken out by filtration, washed with three times the amount of methyl ethyl ketone at 25 ° C. three times, and then dried under reduced pressure for 16 hours to obtain a purified product. 5-Methyl-4-heptene-3 in the obtained arginine salt of 2-hexyldecylphosphate
-The content of on was 890 ppm. In addition, the hue of this substance was Klett 11, and an offensive odor was observed in the sensory evaluation of odor.

Reference Example Using the same 2-hexyldecanol as in Example 1, phosphorylation was carried out in the same manner as in Example 1 to obtain acidic crude 2-hexyldecylphosphoric acid. The content of 5-methyl-4-hepten-3-one in this crude 2-hexyldecylphosphate was 0 pp.
m. The hue of this material was Klett 32.

To this acidic crude 2-hexyldecylphosphoric acid, an equal amount of ethanol was added and dissolved at 60 ° C., and the mixture was added to 3 times the amount of acetone of crude 2-hexyldecylphosphoric acid and added at 25 ° C. for 1 hour.
Upon stirring for 2 hours, the content of mesityl oxide in 2-hexyldecylphosphoric acid was 0 ppm. The hue was Klett 25.

From these results, it can be seen that the acetone dimerization did not occur even if the 2-hexyldecylphosphoric acid was not neutralized but was in the acid form and was treated with acetone at 25 ° C.

Claims (6)

[Claims] 1. A process for producing a branched dimerized alkyl phosphate basic amino acid salt, which comprises carrying out the following steps (a) to (c). Step (a): Step of phosphorylating branched dimerized alcohol to obtain branched dimerized alkyl phosphoric acid Step (b): Neutralization of crude branched dimerized alkyl phosphoric acid obtained in step (a) with basic amino acid Step (c): The neutralized product obtained in step (b) is added to a ketone solvent, and crystals of a branched dimerized alkyl phosphate basic amino acid salt are precipitated at a temperature of 0 to 20 ° C. for separation. Process 2. The washing and separation of the crystals obtained in step (c) with a ketone solvent is repeated at a temperature of 0 to 20 ° C. to reduce the content of the ketone solvent dimer to 500 ppm or less. The manufacturing method according to claim 1, which is characterized in that. 3. The method according to claim 1, wherein the ketone solvent is acetone or methyl ethyl ketone. 4. The production method according to claim 1, wherein the crystal precipitation and the washing with a ketone solvent are carried out at a temperature of 0 to 10 ° C. 5. The branched dimerized alcohol has 4 to 18 carbon atoms.
The method according to any one of claims 1 to 4, which is an alcohol obtained by dimerizing the alcohol of (1) by a Guerbet reaction. 6. The production method according to claim 1, wherein the basic amino acid is arginine, histidine or lysine.