JPH10279546A - Production of n-long chain acyl acidic amino acid or its salt - Google Patents
Production of n-long chain acyl acidic amino acid or its saltInfo
- Publication number
- JPH10279546A JPH10279546A JP2304198A JP2304198A JPH10279546A JP H10279546 A JPH10279546 A JP H10279546A JP 2304198 A JP2304198 A JP 2304198A JP 2304198 A JP2304198 A JP 2304198A JP H10279546 A JPH10279546 A JP H10279546A
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- Prior art keywords
- amino acid
- acidic amino
- salt
- reaction
- acid
- Prior art date
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は、N−長鎖アシル酸
性アミノ酸又はその塩の製造方法に関し、更に詳しくは
グルタミン酸、アスパラギン酸等の酸性アミノ酸又はそ
れらの塩と長鎖脂肪酸ハライドとを反応させることによ
る、N−長鎖アシル酸性アミノ酸又はその塩の製造方法
に関する。TECHNICAL FIELD The present invention relates to a method for producing an N-long-chain acyl acidic amino acid or a salt thereof, and more particularly, to reacting an acidic amino acid such as glutamic acid or aspartic acid or a salt thereof with a long-chain fatty acid halide. And a method for producing an N-long-chain acyl acidic amino acid or a salt thereof.
【0002】[0002]
【従来の技術】N−長鎖アシル酸性アミノ酸、例えば、
N−長鎖アシルグルタミン酸、N−長鎖アシルアスパラ
ギン酸、又はそのナトリウム塩、カリウム塩、トリエタ
ノールアミン塩等のアルカノールアミン塩などは、界面
活性作用、殺菌作用などを有するため、洗浄剤、分散
剤、乳化剤、抗菌剤などとして各種用途に利用されてい
る。特に皮膚や毛髪に対する刺激が低いことから、毛髪
洗浄剤、身体洗浄剤等の洗浄剤組成物に広く用いられて
いる。2. Description of the Related Art N-long-chain acyl acidic amino acids, for example,
N-long-chain acylglutamic acid, N-long-chain acylaspartic acid, or alkanolamine salts such as sodium salt, potassium salt, and triethanolamine salt thereof have a surfactant activity, a bactericidal activity, and the like. It is used in various applications as an agent, an emulsifier, an antibacterial agent, and the like. Particularly, since it has low irritation to the skin and hair, it is widely used in cleaning compositions such as hair cleaning agents and body cleaning agents.
【0003】N−長鎖アシル酸性アミノ酸、例えば、N
−長鎖アシルグルタミン酸の合成方法としては、グルタ
ミン酸と長鎖脂肪酸ハライドとを水溶媒中、アルカリの
存在下に反応させる方法が知られている(例えば、特公
昭48−35058号公報第7欄冒頭の参考例)。しか
し、この方法では収率が低く、工業的に用いるのに十分
な方法とは言えない。[0003] N-long chain acyl acidic amino acids such as N
As a method for synthesizing long-chain acylglutamic acid, a method is known in which glutamic acid and a long-chain fatty acid halide are reacted in an aqueous solvent in the presence of an alkali (for example, JP-B-48-35058, column 7, beginning). Reference example). However, this method has a low yield and cannot be said to be a method sufficient for industrial use.
【0004】高収率でN−長鎖アシル酸性アミノ酸を製
造する方法としては、水溶媒に触媒として、第三級アミ
ンまたは第四級アンモニウム塩を触媒として使用する方
法が知られている(特公昭48−35058号公報)。
しかし、これら触媒は皮膚刺激性等の安全性の問題、ま
たは使用した触媒等の臭いの問題があるため、目的生成
物中に残留するこれらの触媒を除去するための工程及び
設備が必要となり、工業的に満足のいく方法とは言えな
かった。[0004] As a method for producing an N-long-chain acyl acidic amino acid in high yield, a method using a tertiary amine or a quaternary ammonium salt as a catalyst in an aqueous solvent as a catalyst is known. JP-B-48-35058).
However, since these catalysts have safety problems such as skin irritation or odor problems such as used catalysts, a process and equipment for removing these catalysts remaining in the target product are required, It was not an industrially satisfactory method.
【0005】収率を上げるための他の方法としては、反
応溶媒としてアセトン、メチルエチルケトン、ジオキサ
ン、テトラヒドロフランなどの有機溶媒と水との混合溶
媒を使用する方法が知られている(特公昭46−868
5号公報)。しかし、これらの有機溶媒を使用する場
合、作業環境への影響を考慮する必要性と共に、消防法
の規制を満足するために、特に安全面に配慮した設備の
対策、これに伴う設備投資の必要といった問題が伴う。
また、やはり皮膚刺激性等の安全性、溶媒の臭いの問題
といった面から、目的生成物中に残留するこれら溶媒を
除去するための工程及び設備が必要であった。As another method for increasing the yield, a method using a mixed solvent of water and an organic solvent such as acetone, methyl ethyl ketone, dioxane or tetrahydrofuran as a reaction solvent is known (JP-B-46-868).
No. 5). However, when these organic solvents are used, it is necessary to consider the impact on the work environment, and to meet the regulations of the Fire Service Law, it is necessary to take measures for equipment with special consideration for safety, and to make capital investment accordingly. Such a problem accompanies.
Also, from the viewpoints of safety such as skin irritation and the problem of solvent odor, a process and equipment for removing these solvents remaining in the target product were required.
【0006】また、同様に収率を上げる目的から反応溶
媒として含水低級アルコールを使用する方法が知られて
いる(特公昭51−38681号公報)。しかし、この
方法もまた、目的生成物中に残留する低級アルコール等
の臭いの問題が生じ、これらを除去する工程及び設備が
必要となる。A method of using a water-containing lower alcohol as a reaction solvent for the purpose of increasing the yield is also known (Japanese Patent Publication No. 51-38681). However, this method also has a problem of odor such as lower alcohol remaining in the target product, and requires a step and equipment for removing these.
【0007】[0007]
【発明が解決しようとする課題】本発明の目的は、酸性
アミノ酸と長鎖脂肪酸ハライドとからN−長鎖アシル酸
性アミノ酸を、前記種々の問題点を伴わずにしかも収率
よく製造することのできる方法を提供することである。SUMMARY OF THE INVENTION It is an object of the present invention to provide an N-long-chain acyl acidic amino acid from an acidic amino acid and a long-chain fatty acid halide without the above-mentioned various problems and at a high yield. To provide a way to do it.
【0008】[0008]
【課題を解決するための手段】本発明者らは、かかる実
状に鑑み、鋭意研究の結果、酸性アミノ酸又はその塩と
炭素原子数8〜22の長鎖脂肪酸ハライドとを水溶媒
中、アルカリの存在下に反応させてN−長鎖アシル酸性
アミノ酸を製造する方法において、多価アルコールの共
存下で反応を行うことにより前記目的を達成できること
を見出し、本発明を完成させた。Means for Solving the Problems In view of such circumstances, the present inventors have conducted intensive studies and found that an acidic amino acid or a salt thereof and a long-chain fatty acid halide having 8 to 22 carbon atoms were converted into an alkaline solution in an aqueous solvent. In the method of producing an N-long-chain acyl acidic amino acid by reacting in the presence, it has been found that the above object can be achieved by carrying out the reaction in the presence of a polyhydric alcohol, thereby completing the present invention.
【0009】すなわち本発明は、酸性アミノ酸又はその
塩と炭素原子数8〜22の長鎖脂肪酸ハライドとを水溶
媒中、アルカリの存在下に反応させる際に、多価アルコ
ールの共存下で反応を行うことを特徴とするN−長鎖ア
シル酸性アミノ酸又はその塩の製造方法に関するもので
ある。That is, the present invention provides a method for reacting an acidic amino acid or a salt thereof with a long-chain fatty acid halide having 8 to 22 carbon atoms in an aqueous solvent in the presence of an alkali in the presence of a polyhydric alcohol. The present invention relates to a method for producing an N-long-chain acyl acidic amino acid or a salt thereof.
【0010】[0010]
【発明の実施の形態】本発明の製造方法における出発原
料の一つである酸性アミノ酸又はその塩は、グルタミン
酸及びアスパラギン酸又はそれらの塩等が挙げられる。
これらは光学活性体でもラセミ体でもよい。また塩とし
てはナトリウム塩、カリウム塩などのアルカリ金属塩な
どを挙げることができる。BEST MODE FOR CARRYING OUT THE INVENTION Examples of an acidic amino acid or a salt thereof, which is one of the starting materials in the production method of the present invention, include glutamic acid and aspartic acid, and salts thereof.
These may be optically active or racemic. Examples of the salt include an alkali metal salt such as a sodium salt and a potassium salt.
【0011】酸性アミノ酸又はその塩に反応させる長鎖
脂肪酸ハライドは、炭素原子数8〜22の飽和又は不飽
和脂肪酸ハライドである。例えばノナノイルクロライ
ド、ウンデカノイルクロライド、ラウロイルクロライ
ド、トリデカノイルクロライド、ミリストイルクロライ
ド、パルミトイルクロライド、ステアロイルクロライ
ド、オレオイルクロライドなどの単一組成の飽和又は不
飽和の脂肪酸クロライドの他、椰子油脂肪酸クロライ
ド、牛脂脂肪酸クロライド、硬化牛脂脂肪酸クロライ
ド、大豆油脂肪酸クロライド、綿実油脂肪酸クロライド
などの混合物脂肪酸クロライドも同様に使用することが
できる。The long-chain fatty acid halide to be reacted with an acidic amino acid or a salt thereof is a saturated or unsaturated fatty acid halide having 8 to 22 carbon atoms. For example, other than saturated or unsaturated fatty acid chloride having a single composition such as nonanoyl chloride, undecanoyl chloride, lauroyl chloride, tridecanoyl chloride, myristoyl chloride, palmitoyl chloride, stearoyl chloride, and oleoyl chloride, and coconut oil fatty acid chloride Mixture fatty acid chlorides such as tallow fatty acid chloride, hardened tallow fatty acid chloride, soybean oil fatty acid chloride, and cottonseed oil fatty acid chloride can also be used.
【0012】本発明において反応溶媒の一成分として使
用される多価アルコールとしては、例えばグリセリン、
エチレングリコール、プロピレングリコール、ジプロピ
レングリコール、1, 3−ブチレングリコール、ソルビ
トール、マンニトール、エリスリトール、ペンタエリス
リトール等が挙げられる。またポリエチレングリコール
等、上記に述べたものの重合体でもよい。更に、トレハ
ロース、スクロース等、複数の水酸基を有する非還元性
二糖類も、本発明の多価アルコールに含めることができ
る。これらの多価アルコールはそれぞれ単独で用いて
も、2種以上を混合して用いてもよい。The polyhydric alcohol used as one component of the reaction solvent in the present invention includes, for example, glycerin,
Examples include ethylene glycol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, sorbitol, mannitol, erythritol, and pentaerythritol. Further, a polymer of the above-mentioned ones such as polyethylene glycol may be used. Furthermore, non-reducing disaccharides having a plurality of hydroxyl groups, such as trehalose and sucrose, can also be included in the polyhydric alcohol of the present invention. These polyhydric alcohols may be used alone or in combination of two or more.
【0013】これらの多価アルコールは目的生成物中に
残留しても、皮膚刺激性等の安全性の問題はない。また
これらの多価アルコールのほとんどは化粧料または界面
活性剤等への配合成分として通常使用されるものであ
る。従って、目的生成物中に僅かに残留するこれら多価
アルコールは通常除去の必要が生じない。更に目的生成
物の臭いの問題も大きく改善される。従って、残留溶媒
・触媒等を除去するための設備、製造工程の簡略化等、
大きな工業的メリットが生じる。Even if these polyhydric alcohols remain in the target product, there is no problem of safety such as skin irritation. Most of these polyhydric alcohols are usually used as ingredients in cosmetics or surfactants. Therefore, these polyhydric alcohols remaining in the target product in a small amount usually do not need to be removed. Furthermore, the problem of odor of the target product is greatly improved. Therefore, equipment for removing residual solvents and catalysts, simplification of the manufacturing process, etc.
Significant industrial benefits arise.
【0014】前記多価アルコールのうち、好ましいもの
としてグリセリン、エチレングリコール、プロピレング
リコール、ジプロピレングリコール、ポリエチレングリ
コールなどが上げられる。反応収率の観点及び安価に入
手可能である点等から、エチレングリコール、プロピレ
ングリコール、ジプロピレングリコールが工業的に実施
する上で特に好ましい。Among the above-mentioned polyhydric alcohols, preferred are glycerin, ethylene glycol, propylene glycol, dipropylene glycol, polyethylene glycol and the like. Ethylene glycol, propylene glycol, and dipropylene glycol are particularly preferable from the viewpoint of reaction yield and availability at a low cost in terms of industrial implementation.
【0015】本発明において反応はアルカリ存在下で行
う。実際には、酸性アミノ酸またはその塩を多価アルコ
ール水溶液中、アルカリ存在下で溶解し、それから脂肪
酸ハライドを添加するのがよい。反応収率を上げる観点
から反応溶媒のpHは、pH10〜13の範囲が好まし
い。また反応終了まで、このpHの範囲に維持して反応
を行う方がよい。使用するアルカリには特別の制限はな
く、例えば、水酸化ナトリウム、水酸化カリウム、炭酸
ナトリウム、アンモニアなどが挙げられるが、特に水酸
化ナトリウムが実用的である。In the present invention, the reaction is carried out in the presence of an alkali. In practice, it is preferable to dissolve an acidic amino acid or a salt thereof in a polyhydric alcohol aqueous solution in the presence of an alkali, and then add a fatty acid halide. From the viewpoint of increasing the reaction yield, the pH of the reaction solvent is preferably in the range of pH 10 to 13. Further, it is better to carry out the reaction while maintaining this pH range until the end of the reaction. The alkali used is not particularly limited, and includes, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, ammonia, and the like. Particularly, sodium hydroxide is practical.
【0016】本発明で用いる多価アルコールの反応溶媒
中の濃度は、比較的広範囲にわたって採用できるが、好
ましくは脂肪酸ハライド添加前の重量%濃度で5〜80
%、更に好ましくは5〜50%である。5%より低い場
合には反応収率を高める効果が小さくなり、80%越え
る場合には原料である酸性アミノ酸が反応溶媒に溶けに
くくなる。The concentration of the polyhydric alcohol in the reaction solvent used in the present invention can be adopted over a relatively wide range, but is preferably 5 to 80% by weight before addition of the fatty acid halide.
%, More preferably 5 to 50%. If it is lower than 5%, the effect of increasing the reaction yield will be small, and if it is higher than 80%, the acidic amino acid as a raw material will be less soluble in the reaction solvent.
【0017】本発明における反応温度は、特別の制限は
ないが、通常0℃〜50℃の範囲で行われる。高収率に
反応を進める上で、好ましくは0℃〜40℃である。更
に好ましくは5℃〜30℃である。The reaction temperature in the present invention is not particularly limited, but is usually in the range of 0 ° C to 50 ° C. In order to promote the reaction in a high yield, the temperature is preferably 0 ° C to 40 ° C. More preferably, it is 5 ° C to 30 ° C.
【0018】酸性アミノ酸またはその塩と長鎖脂肪酸ク
ロライドとの使用割合については、目的物質を高収率で
得る上で、前者を後者に対して同モル以上用いるのが好
ましい。この範囲内においても前者の使用割合が大きく
なるほど収率が向上するが、実用上好ましいのは、長鎖
脂肪酸クロライドに対する酸性アミノ酸またはその塩の
使用割合(モル比)が1. 0〜1. 5の範囲である。With respect to the ratio of the acidic amino acid or its salt and the long-chain fatty acid chloride, the former is preferably used in an amount equal to or more than that of the latter in order to obtain the target substance in high yield. Even within this range, the yield increases as the former ratio increases, but it is practically preferable that the ratio (molar ratio) of the acidic amino acid or the salt thereof to the long-chain fatty acid chloride is 1.0 to 1.5. Range.
【0019】酸性アミノ酸またはその塩の濃度は特に制
限はないが、反応収率を高める観点から脂肪酸ハライド
添加前の重量%濃度で10〜60%とするのが収率上好
ましく、15〜50%の範囲が特に好ましい。The concentration of the acidic amino acid or a salt thereof is not particularly limited, but from the viewpoint of increasing the reaction yield, the concentration is preferably from 10 to 60% by weight before addition of the fatty acid halide, and from 15 to 50%. Is particularly preferred.
【0020】反応行う際は反応収率を上げる観点から、
酸性アミノ酸又はその塩を溶媒に溶解した後、攪拌下、
脂肪酸ハライドを徐々に添加する方法が好ましい。反応
時間は各種条件によって異なるが、脂肪酸ハライドの添
加時間が通常1時間から6時間程度であり、添加後の反
応時間は通常10分から4時間程度である。When performing the reaction, from the viewpoint of increasing the reaction yield,
After dissolving the acidic amino acid or a salt thereof in a solvent, with stirring,
A method in which the fatty acid halide is gradually added is preferred. The reaction time varies depending on various conditions, but the addition time of the fatty acid halide is usually about 1 hour to 6 hours, and the reaction time after addition is usually about 10 minutes to 4 hours.
【0021】反応終了後、反応混合物を硫酸、塩酸など
の鉱酸で酸性にし、析出したN−長鎖アシル酸性アミノ
酸を濾別する。また濾別したN−長鎖アシル酸性アミノ
酸を水酸化ナトリウム溶液、水酸化カリウム溶液等で中
和し、その後水を減圧留去することでN−長鎖アシル酸
性アミノ酸塩が得られる。After completion of the reaction, the reaction mixture is acidified with a mineral acid such as sulfuric acid or hydrochloric acid, and the precipitated N-long-chain acyl acidic amino acid is filtered off. The N-long-chain acyl acidic amino acid salt is obtained by neutralizing the filtered N-long-chain acyl acidic amino acid with a sodium hydroxide solution, a potassium hydroxide solution or the like, and then distilling off water under reduced pressure.
【0022】[0022]
【実施例】以下、実施例により本発明を具体的に説明す
るが、本発明はこれらに限定されるものではない。EXAMPLES The present invention will now be described specifically with reference to examples, but the present invention is not limited to these examples.
【0023】実施例1 L−グルタミン酸ナトリウム1水和物175g(0.9
3mol)を13重量%ジプロピレングリコール水溶液
230mlに懸濁し、これに25重量%水酸化ナトリウ
ム水溶液145gを添加し、pH12の水溶液を調整し
た(ジプロピレングリコール濃度、9重量%)。これに
ラウリン酸クロライド158g(0.72mol)と2
5重量%水酸化ナトリウム水溶液を攪拌下、pH12、
10℃を維持しながら、2時間かけて同時に添加し、更
に2時間反応させた。反応終了後、15重量%硫酸でp
H1に調整し、冷水を加えN−ラウロイルグルタミン酸
の結晶を析出させた。その結晶を濾取し、24時間、2
5℃で乾燥させたところ220gであった。HPLCで
分析した結果、N−ラウロイルグルタミン酸の収率は、
89mol%(対ラウリン酸クロライド)であった。Example 1 175 g of sodium L-glutamate monohydrate (0.9 g)
(3 mol) was suspended in 230 ml of a 13% by weight aqueous solution of dipropylene glycol, and 145 g of a 25% by weight aqueous solution of sodium hydroxide was added thereto to prepare an aqueous solution having a pH of 12 (dipropylene glycol concentration, 9% by weight). To this, 158 g (0.72 mol) of lauric chloride and 2
A 5% by weight aqueous solution of sodium hydroxide was stirred at pH 12,
While maintaining the temperature at 10 ° C., the mixture was added simultaneously over 2 hours, and reacted for 2 hours. After completion of the reaction, p
The temperature was adjusted to H1, and cold water was added to precipitate N-lauroylglutamic acid crystals. The crystals were collected by filtration, and
It was 220 g when dried at 5 ° C. As a result of analysis by HPLC, the yield of N-lauroylglutamic acid was
89 mol% (relative to lauric acid chloride).
【0024】実施例2 L−グルタミン酸ナトリウム1水和物175g(0.9
3mol)を13重量%ポリエチレングリコール水溶液
230mlに懸濁し、これに25重量%水酸化ナトリウ
ム水溶液145gを添加し、pH12の水溶液を調整し
た(ポリエチレングリコール濃度、9重量%)。実施例
1と同様に反応を行い、結晶を析出させた。得られたN
−ラウロイルグルタミン酸の結晶を濾取し、24時間、
25℃で乾燥させたところ220gであった。HPLC
で分析した結果、N−ラウロイルグルタミン酸の収率
は、85mol%(対ラウリン酸クロライド)であっ
た。Example 2 175 g of sodium L-glutamate monohydrate (0.9 g)
(3 mol) was suspended in 230 ml of a 13% by weight aqueous solution of polyethylene glycol, and 145 g of a 25% by weight aqueous sodium hydroxide solution was added thereto to adjust the pH 12 aqueous solution (polyethylene glycol concentration, 9% by weight). The reaction was carried out in the same manner as in Example 1 to precipitate crystals. N obtained
-The crystals of lauroylglutamic acid are filtered off and
It was 220 g when dried at 25 ° C. HPLC
As a result, the yield of N-lauroylglutamic acid was 85 mol% (relative to lauric acid chloride).
【0025】実施例3 L−グルタミン酸ナトリウム1水和物175g(0.9
3mol)を20重量%エチレングリコール水溶液25
0mlに懸濁し、これに25重量%水酸化ナトリウム水
溶液145gを添加し、pH12の水溶液を調整した
(エチレングリコール濃度、14重量%)。実施例1と
同様に反応を行い、結晶を析出させた。得られたN−ラ
ウロイルグルタミン酸の結晶を濾取し、24時間、25
℃で乾燥させたところ223gであった。HPLCで分
析した結果、N−ラウロイルグルタミン酸の収率は、9
1mol%(対ラウリン酸クロライド)であった。Example 3 175 g of sodium L-glutamate monohydrate (0.9 g)
3 mol) in a 20% by weight aqueous ethylene glycol solution 25
The suspension was suspended in 0 ml, and 145 g of a 25% by weight aqueous sodium hydroxide solution was added thereto to adjust the pH 12 aqueous solution (ethylene glycol concentration, 14% by weight). The reaction was carried out in the same manner as in Example 1 to precipitate crystals. The obtained crystals of N-lauroylglutamic acid were collected by filtration and left for 25 hours for 25 hours.
It was 223 g when dried at ° C. As a result of analysis by HPLC, the yield of N-lauroylglutamic acid was 9%.
1 mol% (relative to lauric chloride).
【0026】実施例4 L−グルタミン酸ナトリウム1水和物175g(0.9
3mol)と7. 5重量%スクロース水溶液230ml
に懸濁し、これに25重量%水酸化ナトリウム水溶液1
45gを添加し、pH12の水溶液を調整した(スクロ
ース濃度、5重量%)。実施例1と同様に反応を行い、
結晶を析出させた。得られたN−ラウロイルグルタミン
酸の結晶を濾取し、24時間、25℃で乾燥させたとこ
ろ215gであった。HPLCで分析した結果、N−ラ
ウロイルグルタミン酸の収率は、82mol%(対ラウ
リン酸クロライド)であった。Example 4 175 g of sodium L-glutamate monohydrate (0.9 g)
3 mol) and 230 ml of 7.5% by weight sucrose aqueous solution
And a 25% by weight aqueous sodium hydroxide solution 1
45 g was added to adjust the pH 12 aqueous solution (sucrose concentration, 5% by weight). The reaction was carried out in the same manner as in Example 1,
Crystals were deposited. The obtained crystals of N-lauroylglutamic acid were collected by filtration and dried at 25 ° C. for 24 hours to obtain 215 g. As a result of analysis by HPLC, the yield of N-lauroylglutamic acid was 82 mol% (relative to lauric acid chloride).
【0027】実施例5 L−グルタミン酸ナトリウム1水和物175g(0.9
3mol)を15重量%プロピレングリコール水溶液2
40mlに懸濁し、これに25重量%水酸化ナトリウム
水溶液140gを添加し、pH11の水溶液を調整した
(プロピレングリコール濃度、10重量%)。pH1
1、20℃を維持しながら、ラウリン酸クロライド17
0g(0.78mol)を使用し、実施例1と同様の操
作を行った。得られたN−ラウロイルグルタミン酸の結
晶を濾取し、24時間、25℃で乾燥させたところ23
5gであった。HPLCで分析した結果、N−ラウロイ
ルグルタミン酸の収率は、90mol%(対ラウリン酸
クロライド)であった。Example 5 175 g of sodium L-glutamate monohydrate (0.9 g)
3 mol) in 15% by weight propylene glycol aqueous solution 2
The suspension was suspended in 40 ml, and 140 g of a 25% by weight aqueous sodium hydroxide solution was added thereto to adjust the pH 11 aqueous solution (propylene glycol concentration, 10% by weight). pH1
1. Maintaining lauric chloride 17
The same operation as in Example 1 was performed using 0 g (0.78 mol). The obtained crystals of N-lauroylglutamic acid were collected by filtration and dried at 25 ° C. for 24 hours.
It was 5 g. As a result of analysis by HPLC, the yield of N-lauroylglutamic acid was 90 mol% (relative to lauric acid chloride).
【0028】実施例6 L−グルタミン酸ナトリウム1水和物175g(0.9
3mol)を15重量%グリセリン240mlに懸濁
し、これに25重量%水酸化ナトリウム水溶液145g
を添加し、pH12の水溶液を調整した(グリセリン濃
度、10重量%)。実施例1と同様に反応を行い、結晶
を析出させた。得られたN−ラウロイルグルタミン酸の
結晶を濾取し、24時間、25℃で乾燥させたところ2
00gであった。HPLCで分析した結果、ラウロイル
グルタミン酸の収率は、81mol%(対ラウリン酸ク
ロライド)であった。Example 6 175 g of sodium L-glutamate monohydrate (0.9 g)
3 mol) was suspended in 240 ml of 15% by weight glycerin, and 145 g of a 25% by weight aqueous sodium hydroxide solution was added thereto.
Was added to adjust the pH 12 aqueous solution (glycerin concentration, 10% by weight). The reaction was carried out in the same manner as in Example 1 to precipitate crystals. The obtained crystals of N-lauroylglutamic acid were collected by filtration and dried at 25 ° C. for 24 hours.
00 g. As a result of analysis by HPLC, the yield of lauroylglutamic acid was 81 mol% (relative to lauric acid chloride).
【0029】実施例7 水200mlにプロピレングリコールを加え、プロピレ
ングリコール濃度の異なる反応溶媒を複数調製し、各々
にL−グルタミン酸ナトリウム1水和物175g(0.
93mol)を懸濁した後、これに25重量%水酸化ナ
トリウム水溶液145gを添加し、pH12の水溶液を
調整した。椰子油脂肪酸クロライド160.9g(0.
72mol)を用いて実施例1と同様の操作を行った。
椰子油脂肪酸クロライド添加前のプロピレングリコール
濃度とN−椰子油脂肪酸アシルグルタミン酸の収率との
関係を表1に示す。Example 7 Propylene glycol was added to 200 ml of water to prepare a plurality of reaction solvents having different propylene glycol concentrations, and 175 g (0.1 g) of sodium L-glutamate monohydrate was added to each of them.
After suspending 93 mol), 145 g of a 25% by weight aqueous sodium hydroxide solution was added to the suspension to prepare a pH 12 aqueous solution. 160.9 g of coconut oil fatty acid chloride (0.
72 mol), and the same operation as in Example 1 was performed.
Table 1 shows the relationship between the propylene glycol concentration before addition of the coconut oil fatty acid chloride and the yield of N-coconut oil fatty acylglutamic acid.
【0030】[0030]
【表1】 [Table 1]
【0031】試験例 臭いの官能評価 反応溶媒として13重量%エタノール水溶液を用い、実
施例1と同様に反応させ、同様の操作でN−ラウロイル
グルタミン酸の結晶を得、これを比較例として用いた。
実施例1、2、3、4、5、6及び上記比較例で得られ
たラウロイルグルタミン酸100gを25重量%水酸化
ナトリウム水溶液で溶解し、pH7.3の界面活性剤溶
液450gを調製した。この界面活性剤溶液につき、2
5℃において臭いの評価を行った。10人のパネラーに
より、以下の基準に従って評価点をつけ、その平均値を
表2に示した。 全く臭い無し 0点 僅かに臭い有り 1点 臭い有り 2点 強い臭い有り 3点Test Example Sensory evaluation of odor Using a 13% by weight aqueous ethanol solution as a reaction solvent, the reaction was carried out in the same manner as in Example 1. By the same operation, crystals of N-lauroylglutamic acid were obtained and used as a comparative example.
100 g of lauroylglutamic acid obtained in Examples 1, 2, 3, 4, 5, and 6 and the comparative example were dissolved in a 25% by weight aqueous sodium hydroxide solution to prepare 450 g of a surfactant solution having a pH of 7.3. 2 per this surfactant solution
The odor was evaluated at 5 ° C. An evaluation score was given by 10 panelists according to the following criteria, and the average value is shown in Table 2. No odor 0 point Slight odor 1 point Smell 2 points Strong odor 3 points
【0032】[0032]
【表2】 [Table 2]
【0033】[0033]
【発明の効果】本発明によれば、N−長鎖アシル酸性ア
ミノ酸又はその塩を高収率で製造でき、消防法上の安全
性等への配慮又は残留溶媒・触媒等の除去のために要す
る過大な設備及び製造工程を簡略化できる等、工業的に
有利に実施することができる。According to the present invention, an N-long-chain acyl acidic amino acid or a salt thereof can be produced in a high yield. It can be implemented industrially advantageously, for example, the required excessive equipment and manufacturing steps can be simplified.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 FI C11D 1/10 C11D 1/10 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification code FI C11D 1/10 C11D 1/10
Claims (2)
〜22の長鎖脂肪酸ハライドとを水溶媒中、アルカリの
存在下に反応させる際に、多価アルコールの共存下に反
応を行うことを特徴とするN−長鎖アシル酸性アミノ酸
又はその塩の製造方法。Claims: 1. An acidic amino acid or a salt thereof and 8 carbon atoms
Wherein the reaction is carried out in the presence of an alkali in a water solvent in the presence of an alkali, wherein the reaction is carried out in the presence of a polyhydric alcohol; Method.
グリコール、プロピレングリコール、ジプロピレングリ
コール、ポリエチレングリコールから選ばれる1種又は
2種以上である請求項1記載の製造方法。2. The method according to claim 1, wherein the polyhydric alcohol is one or more selected from glycerin, ethylene glycol, propylene glycol, dipropylene glycol, and polyethylene glycol.
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JP02304198A JP3948094B2 (en) | 1997-02-05 | 1998-02-04 | Method for producing N-long chain acyl acidic amino acid or salt thereof |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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JP2270897 | 1997-02-05 | ||
JP9-22708 | 1997-02-05 | ||
JP02304198A JP3948094B2 (en) | 1997-02-05 | 1998-02-04 | Method for producing N-long chain acyl acidic amino acid or salt thereof |
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JP2006193597A Division JP2006312643A (en) | 1997-02-05 | 2006-07-14 | Method for producing n-long-chain acyl acidic amino acid or its salt |
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Publication Number | Publication Date |
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JP3948094B2 JP3948094B2 (en) | 2007-07-25 |
Family
ID=26359975
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005200413A (en) * | 2003-12-19 | 2005-07-28 | Ajinomoto Co Inc | Crystal of n-long chain acyl glutamic acid and/or its salt |
JP2010513244A (en) * | 2006-12-13 | 2010-04-30 | センテニアル ヴェンチャーズ ビー.ブイ. | Less irritating composition for skin sterilization |
KR101086180B1 (en) * | 2003-12-19 | 2011-11-25 | 아지노모토 가부시키가이샤 | A process for producing crystal of n-long chain acyl glutamate or salt thereof |
JP2016539951A (en) * | 2013-08-21 | 2016-12-22 | 南京▲華▼▲獅▼新材料有限公司 | Method for producing N-acyl acidic amino acid or salt thereof and use thereof |
CN114380711A (en) * | 2021-12-30 | 2022-04-22 | 广州花语精细化工有限公司 | Preparation method of amino acid surfactant |
WO2023001267A1 (en) * | 2021-07-23 | 2023-01-26 | 苏州欧丽特生物医药有限公司 | Supramolecular amino acid or salt thereof, and preparation method therefor and application thereof |
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1998
- 1998-02-04 JP JP02304198A patent/JP3948094B2/en not_active Expired - Lifetime
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005200413A (en) * | 2003-12-19 | 2005-07-28 | Ajinomoto Co Inc | Crystal of n-long chain acyl glutamic acid and/or its salt |
JP4600030B2 (en) * | 2003-12-19 | 2010-12-15 | 味の素株式会社 | Crystal of N-long chain acyl glutamic acid and / or salt thereof |
KR101086180B1 (en) * | 2003-12-19 | 2011-11-25 | 아지노모토 가부시키가이샤 | A process for producing crystal of n-long chain acyl glutamate or salt thereof |
JP2010513244A (en) * | 2006-12-13 | 2010-04-30 | センテニアル ヴェンチャーズ ビー.ブイ. | Less irritating composition for skin sterilization |
JP2016539951A (en) * | 2013-08-21 | 2016-12-22 | 南京▲華▼▲獅▼新材料有限公司 | Method for producing N-acyl acidic amino acid or salt thereof and use thereof |
WO2023001267A1 (en) * | 2021-07-23 | 2023-01-26 | 苏州欧丽特生物医药有限公司 | Supramolecular amino acid or salt thereof, and preparation method therefor and application thereof |
CN114380711A (en) * | 2021-12-30 | 2022-04-22 | 广州花语精细化工有限公司 | Preparation method of amino acid surfactant |
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