JP3025725B2 - Method for separating and purifying N-long-chain acylamino acids - Google Patents
Method for separating and purifying N-long-chain acylamino acidsInfo
- Publication number
- JP3025725B2 JP3025725B2 JP4313047A JP31304792A JP3025725B2 JP 3025725 B2 JP3025725 B2 JP 3025725B2 JP 4313047 A JP4313047 A JP 4313047A JP 31304792 A JP31304792 A JP 31304792A JP 3025725 B2 JP3025725 B2 JP 3025725B2
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- long
- acid
- chain acylamino
- chain
- acylamino acid
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Description
【０００１】[0001]
【産業上の利用分野】本発明はＮ−長鎖アシルアミノ酸
の分離法及び精製法に関し、より詳細には、Ｎ−長鎖ア
シルアミノ酸の合成反応液からのＮ−長鎖アシルアミノ
酸の分離法、及び無機塩等の不純物を含有する不純Ｎ−
長鎖アシルアミノ酸の精製法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for separating and purifying N-long-chain acylamino acids, and more particularly to a method for separating N-long-chain acylamino acids from a reaction solution for synthesizing N-long-chain acylamino acids. , And impurity N- containing impurities such as inorganic salts.
The present invention relates to a method for purifying long-chain acylamino acids.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】Ｎ−長
鎖アシルアミノ酸塩は、優れた界面活性作用、抗菌作用
等を有し、低刺激性であることが知られており、様々な
分野において用いられている。従来、これらＮ−長鎖ア
シルアミノ酸塩の原料となるＮ−長鎖アシルアミノ酸
は、アミノ酸のアルカリ水溶液に脂肪酸ハライドを反応
させるショッテン−バウマン(Schotten-Baumann)法で製
造されており、その改良発明である特公昭４６−８６８
５号公報、特公昭５１−３８６８１号公報には親水性溶
媒を含むアミノ酸水溶液に、アルカリ物質の存在下で脂
肪酸ハライドを添加して反応させる方法が開示されてい
る。この合成反応液よりＮ−長鎖アシルアミノ酸を分離
するのに該溶液を鉱酸等でpHを１〜５に調整した後、晶
析分離する方法が知られている。しかし、結晶を濾過分
離する工程は特別の設備を必要とする上、結晶内に取り
込まれた不純物の洗浄にさらに多量の洗浄水が必要とな
る等の欠点がある。2. Description of the Related Art N-long-chain acylamino acid salts are known to have excellent surfactant activity, antibacterial activity, etc., and to be hypoallergenic. Used in Conventionally, N-long-chain acylamino acids, which are the raw materials for these N-long-chain acylamino acid salts, have been produced by the Schotten-Baumann method in which a fatty acid halide is reacted with an alkaline aqueous solution of an amino acid. Is Tokuboku Sho 46-868
No. 5, JP-B-51-38681 discloses a method in which a fatty acid halide is added to an aqueous solution of an amino acid containing a hydrophilic solvent in the presence of an alkaline substance to cause a reaction. In order to separate an N-long-chain acylamino acid from this synthesis reaction solution, a method is known in which the solution is adjusted to a pH of 1 to 5 with a mineral acid or the like and then separated by crystallization. However, the process of filtering and separating the crystals requires special equipment, and has the drawbacks that a larger amount of washing water is required for washing impurities taken into the crystals.
【０００３】この改良方法として、特公昭５７−４７９
０２号公報には、水と親水性溶媒との混合溶媒中で、シ
ョッテン−バウマン反応を行い、40℃から親水性溶媒の
沸点の温度においてpHを１〜６に調整し、有機層よりＮ
−長鎖アシルアミノ酸を分離取得する方法が開示されて
いる。しかし、親水性溶媒を含む廃液の処理が問題とな
り、工業的手法として有利とは言えない。従って、品質
が良く、高純度のＮ−長鎖アシルアミノ酸を工業的に有
利に分離する方法の開発が望まれていた。As an improvement method, Japanese Patent Publication No. 57-479 is disclosed.
No. 02 discloses that a Schotten-Baumann reaction is carried out in a mixed solvent of water and a hydrophilic solvent, the pH is adjusted to 1 to 6 at a temperature from 40 ° C. to the boiling point of the hydrophilic solvent, and N
-A method for separating and obtaining long-chain acyl amino acids is disclosed. However, treatment of waste liquid containing a hydrophilic solvent becomes a problem, and is not advantageous as an industrial method. Therefore, it has been desired to develop a method for industrially and advantageously separating high-quality, high-purity N-long-chain acylamino acids.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、Ｎ−長鎖
アシルアミノ酸の合成反応液から、Ｎ−長鎖アシルアミ
ノ酸を濾過等の晶析工程を用いることなく、また親水性
溶媒等の有機溶媒を使用することなく、工業的に有利に
分離する方法を鋭意検討した結果、融解したＮ−長鎖ア
シルアミノ酸は水と分層し、効率良くＮ−長鎖アシルア
ミノ酸を分離できることを見出した。しかも驚くべきこ
とに、水中でＮ−長鎖アシルアミノ酸は融点以下の温度
でも融解し、融点が水の沸点以上のＮ−長鎖アシルアミ
ノ酸も常圧下、水層と該Ｎ−長鎖アシルアミノ酸を含む
層とに分層することを見出した。しかもここで得たＮ−
長鎖アシルアミノ酸は、水洗工程を経る上記公知方法で
得られたものと同等かそれ以上の純度を有していること
も見出した。これらの知見に基づいて、本発明を完成し
た。Means for Solving the Problems The present inventors have prepared an N-long-chain acylamino acid synthesis reaction solution from an N-long-chain acylamino acid synthesis reaction without using a crystallization step such as filtration, and a hydrophilic solvent or the like. As a result of diligent studies on a method for industrially advantageous separation without using an organic solvent, it was found that the molten N-long-chain acylamino acid can be separated from water to efficiently separate the N-long-chain acylamino acid. I found it. Surprisingly, the N-long-chain acylamino acid melts in water even at a temperature lower than the melting point, and the N-long-chain acylamino acid having a melting point higher than the boiling point of water is also added to the aqueous layer under normal pressure. And a layer containing. And the N-
It has also been found that long-chain acylamino acids have a purity equal to or higher than that obtained by the above-mentioned known method through a washing step. The present invention has been completed based on these findings.
【０００５】即ち本発明は、アミノ酸水溶液へ、アルカ
リの存在下に炭素数６〜22の脂肪酸ハライドを添加して
反応させ、得られるＮ−長鎖アシルアミノ酸アルカリ塩
の合成反応液を鉱酸でpH１〜５に調整してＮ−長鎖アシ
ルアミノ酸に変換し、該Ｎ−長鎖アシルアミノ酸の融解
状態下で、水層とＮ−長鎖アシルアミノ酸を含む有機層
に分層し、次いで有機層より該Ｎ−長鎖アシルアミノ酸
を分離取得することを特徴とするＮ−長鎖アシルアミノ
酸の分離法を提供するものであり、また本発明は、無機
塩等の不純物を含むＮ−長鎖アシルアミノ酸を水と混合
し、該Ｎ−長鎖アシルアミノ酸の融解状態下で、水層と
Ｎ−長鎖アシルアミノ酸を含む有機層に分層し、次いで
有機層より、高純度のＮ−長鎖アシルアミノ酸を得るこ
とを特徴とするＮ−長鎖アシルアミノ酸の精製法を提供
するものである。That is, according to the present invention, a fatty acid halide having 6 to 22 carbon atoms is added to an aqueous amino acid solution in the presence of an alkali to cause a reaction. The solution is adjusted to pH 1 to 5 to convert it into N-long chain acyl amino acids, and under the molten state of the N-long chain acyl amino acids, is separated into an aqueous layer and an organic layer containing N-long chain acyl amino acids. A method for separating an N-long-chain acylamino acid, comprising separating and obtaining the N-long-chain acylamino acid from a layer. The present invention also provides an N-long-chain acylamino acid containing impurities such as inorganic salts. The acylamino acid is mixed with water, and the aqueous layer and the organic layer containing the N-long-chain acylamino acid are separated under the melting state of the N-long-chain acylamino acid. Obtaining N-chain acylamino acids It is intended to provide a method for purifying long-chain acylamino acids.
【０００６】本発明に適用できるＮ−長鎖アシルアミノ
酸は、各種アミノ酸のアミノ基にアシル基を導入したア
ミノ酸誘導体で、長鎖アシル基としては、炭素数６〜22
の飽和又は不飽和脂肪酸より誘導されるアシル基、例え
ばラウリン酸、パルミチン酸、ステアリン酸、オレイン
酸などの単一組成の脂肪酸によるアシル基のほかに、ヤ
シ油脂肪酸、牛脂脂肪酸等の混合脂肪酸のアシル基でも
良い。アミノ酸残基については、天然或いは合成により
得られるいずれのアミノ酸の残基でも良いが、例えばグ
リシン、β−アラニン、Ｎ−メチル−β−アラニン等の
残基が挙げられる。The N-long-chain acyl amino acids applicable to the present invention are amino acid derivatives in which an acyl group is introduced into the amino group of various amino acids, and the long-chain acyl group has 6 to 22 carbon atoms.
Acyl groups derived from saturated or unsaturated fatty acids of, for example, lauric acid, palmitic acid, stearic acid, in addition to acyl groups of fatty acids of a single composition such as oleic acid, coconut oil fatty acids, mixed fatty acids such as tallow fatty acids An acyl group may be used. The amino acid residue may be any amino acid residue obtained naturally or synthetically, and includes, for example, residues of glycine, β-alanine, N-methyl-β-alanine and the like.
【０００７】Ｎ−長鎖アシルアミノ酸アルカリ塩の調製
はいずれの方法でもよいが、例えばE. Jungermann らの
報文 (E. Jungermann et al., J. Am. Chem. Soc., 78,
172(1956)) に記載されているように、アミノ酸水溶液
へ、アルカリの存在下、炭素数６〜22の脂肪酸ハライド
を添加し、10〜35℃で１〜２時間反応させる方法が好ま
しく用いられる。また、特公昭４６−８６８５号公報、
特公昭５１−３８６８１号公報に記載されているよう
に、親水性有機溶媒を用いた場合は、廃水への該親水性
有機溶媒の混入を防ぐためＮ−長鎖アシルアミノ酸アル
カリ塩の調製後、該親水性有機溶媒をあらかじめ留去
し、分層する必要がある。The N-long-chain acylamino acid alkali salt can be prepared by any method. For example, a report by E. Jungermann et al. (E. Jungermann et al., J. Am. Chem. Soc., 78 ,
172 (1956)), a method in which a fatty acid halide having 6 to 22 carbon atoms is added to an aqueous amino acid solution in the presence of an alkali and reacted at 10 to 35 ° C for 1 to 2 hours is preferably used. . In addition, Japanese Patent Publication No. 46-8865,
As described in JP-B-51-38681, when a hydrophilic organic solvent is used, after the preparation of an N-long-chain acylamino acid alkali salt in order to prevent the hydrophilic organic solvent from being mixed into wastewater, It is necessary to previously distill off the hydrophilic organic solvent and separate layers.
【０００８】Ｎ−長鎖アシルアミノ酸アルカリ塩からＮ
−長鎖アシルアミノ酸への変換は特に困難はなく、硫
酸、塩酸等の鉱酸でpHを１〜５に調整すれば良い。即
ち、Ｎ−長鎖アシルアミノ酸アルカリ塩を含む水溶液
に、攪拌しながら鉱酸を加えpHを１〜５に調整するとよ
い。ここでの温度は特に規定されない。[0008] N-long chain acyl amino acid alkali salt to N
-Conversion to long-chain acylamino acids is not particularly difficult, and the pH may be adjusted to 1 to 5 with a mineral acid such as sulfuric acid or hydrochloric acid. That is, the pH is preferably adjusted to 1 to 5 by adding a mineral acid to the aqueous solution containing the alkali salt of N-long-chain acylamino acid while stirring. The temperature here is not particularly defined.
【０００９】水層とＮ−長鎖アシルアミノ酸を含む有機
層とを分層するための温度条件は、Ｎ−長鎖アシルアミ
ノ酸が融解している温度であれば良いが、通常、室温か
ら100 ℃の間で行われる。100 ℃を越えると、水の沸点
を越すため、加圧下での分層が必要となり多額の設備費
用が必要となり、不利である。なお、Ｎ−長鎖アシルア
ミノ酸が融解している状態とは、流動性を保ち液状化し
ている状態をいう。本発明を該Ｎ−長鎖アシルアミノ酸
の融点以上の温度で実施することはもちろん可能である
が、該Ｎ−長鎖アシルアミノ酸は含水すると融点以下の
温度でも融解するため、比較的低温でも本発明が実施で
きる利点がある。この融解物と水との混合物を静置すれ
ば通常容易に分層するが、分層性が悪い場合、例えば硫
酸ナトリウム、塩化ナトリウム等の無機塩を添加し、改
善することも可能である。分層したものより水層を分離
し、Ｎ−長鎖アシルアミノ酸が得られる。更に純度を上
げるために、本発明の処理を２回以上繰り返すこともで
きる。なお、本発明はバッチ式、連続式いずれを採用し
ても差し支えない。The temperature condition for separating the aqueous layer and the organic layer containing N-long-chain acylamino acids may be any temperature at which the N-long-chain acylamino acids are melted. Performed between ° C. If the temperature exceeds 100 ° C., the boiling point of water is exceeded, so that it is necessary to separate the layers under pressure, which requires a large amount of equipment cost and is disadvantageous. The state in which the N-long-chain acylamino acid is molten refers to a state in which the N-long-chain acylamino acid is liquefied while maintaining fluidity. It is of course possible to carry out the present invention at a temperature not lower than the melting point of the N-long-chain acylamino acid. There are advantages that the invention can be implemented. If the mixture of the melt and water is allowed to stand, the layers are usually easily separated. However, when the layer separation is poor, it is possible to improve the separation by adding an inorganic salt such as sodium sulfate and sodium chloride. The aqueous layer is separated from the separated layers to obtain an N-long-chain acylamino acid. To further increase the purity, the treatment of the present invention can be repeated two or more times. The present invention may employ either a batch type or a continuous type.
【００１０】本発明を実施して得られる有機層は、水分
を含んだＮ−長鎖アシルアミノ酸であるが、乾燥は特に
困難ではない。例えば、真空加熱により乾燥する方法、
空気、窒素等の気体で置換しながら乾燥する方法、冷却
固化後、粉砕して乾燥する方法、又は噴霧乾燥等であ
る。また、該Ｎ−長鎖アシルアミノ酸を、例えばナトリ
ウム、カリウム、トリエタノールアミン等のＮ−長鎖ア
シルアミノ酸塩水溶液として用いる場合のように、特に
乾燥したＮ−長鎖アシルアミノ酸が必要ない場合、本発
明を実施して得られる水分を含んだＮ−長鎖アシルアミ
ノ酸をそのまま使用できる。また、噴霧冷却、転動造粒
等を行うことにより、水分を持ったまま微粒化すること
も可能である。The organic layer obtained by carrying out the present invention is an N-long-chain acylamino acid containing water, but drying is not particularly difficult. For example, a method of drying by vacuum heating,
A method of drying while replacing with a gas such as air or nitrogen, a method of pulverizing and drying after cooling and solidifying, or a method of spray drying. Further, when the N-long-chain acylamino acid is used as an aqueous solution of an N-long-chain acylamino acid salt such as sodium, potassium, triethanolamine, etc., particularly when a dry N-long-chain acylamino acid is not required, The N-long-chain acyl amino acid containing water obtained by carrying out the present invention can be used as it is. Further, by performing spray cooling, tumbling granulation, and the like, it is possible to atomize the powder while retaining moisture.
【００１１】本発明は、Ｎ−長鎖アシルアミノ酸の合成
反応液より、Ｎ−長鎖アシルアミノ酸を分離する場合の
他、無機塩等の不純物の混入したＮ−長鎖アシルアミノ
酸の精製にも適用できる。この場合、該不純なＮ−長鎖
アシルアミノ酸を水と混合し、上記と同様にＮ−長鎖ア
シルアミノ酸の融解状態下で、水層と有機層に分層し、
次いで有機層より、高純度のＮ−長鎖アシルアミノ酸を
得ることができる。The present invention is applicable not only to the separation of N-long-chain acylamino acids from a reaction solution for the synthesis of N-long-chain acylamino acids, but also to the purification of N-long-chain acylamino acids contaminated with impurities such as inorganic salts. Applicable. In this case, the impure N-long-chain acylamino acid is mixed with water, and separated into an aqueous layer and an organic layer under the molten state of the N-long-chain acylamino acid as described above,
Next, high-purity N-long-chain acylamino acids can be obtained from the organic layer.
【００１２】[0012]
【実施例】以下、実施例により本発明を詳細に説明する
が、本発明はこれら実施例に限定されるものではない。
尚、例中の％及び部は特記しないかぎり重量基準であ
る。EXAMPLES The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples.
The percentages and parts in the examples are on a weight basis unless otherwise specified.
【００１３】実施例１Ｎ−ラウロイル−β−アラニンの製造 β−アラニン98ｇを水399mlに溶解させ、これに48％水
酸化カリウム水溶液129ｇを加えてβ−アラニンカリウ
ム液を得た（中和反応）。次いで、これを15〜20℃に保
ちつつラウリン酸クロライド219 ｇと30％水酸化カリウ
ム水溶液187 ｇを同時に約 1.5時間かけて添加した。添
加終了後、さらに同温度で１時間攪拌し、Ｎ−ラウロイ
ル−β−アラニンカリウム塩を28.5％含む水溶液1032ｇ
を得た（アシル化反応）。これに70℃で35％塩酸を加え
てpH１に調整し、Ｎ−ラウロイル−β−アラニンの結晶
を含むスラリーを得た（酸分解反応）。これを85℃に昇
温すると、Ｎ−ラウロイル−β−アラニンが融解した。
90℃で15分間静置すると、有機層と水層に分層した。有
機層を分離し、含水Ｎ−ラウロイル−β−アラニンを28
6 ｇ得た。これを真空加熱(120℃、200mmHg)により乾燥
し、 266ｇのＮ−ラウロイル−β−アラニンを得た。得
られたＮ−ラウロイル−β−アラニンの融点は 112℃、
塩化カリウム含量は0.7 ％であり、白色度98％であっ
た。ここで白色度とは、標準白板との色差であり、日本
電色工業（株）製ＳＺ−Σ８０を用いて測定した。な
お、酸分解後のスラリーをそのまま乾燥した場合36％の
塩化カリウムが含まれていた。Example 1 Production of N-lauroyl- β-alanine 98 g of β-alanine was dissolved in 399 ml of water, and 129 g of a 48% aqueous potassium hydroxide solution was added thereto to obtain a β-alanine potassium solution (neutralization reaction). ). Then, while maintaining the temperature at 15 to 20 ° C., 219 g of lauric chloride and 187 g of a 30% aqueous potassium hydroxide solution were added simultaneously over about 1.5 hours. After the addition was completed, the mixture was further stirred at the same temperature for 1 hour, and 1032 g of an aqueous solution containing 28.5% of N-lauroyl-β-alanine potassium salt was added.
Was obtained (acylation reaction). The pH was adjusted to 1 by adding 35% hydrochloric acid at 70 ° C. to obtain a slurry containing N-lauroyl-β-alanine crystals (acid decomposition reaction). When the temperature was raised to 85 ° C., N-lauroyl-β-alanine was melted.
After standing at 90 ° C. for 15 minutes, an organic layer and an aqueous layer were separated. The organic layer was separated and hydrated N-lauroyl-β-alanine was added to 28
6 g were obtained. This was dried by vacuum heating (120 ° C., 200 mmHg) to obtain 266 g of N-lauroyl-β-alanine. The melting point of the obtained N-lauroyl-β-alanine is 112 ° C.
The potassium chloride content was 0.7% and the whiteness was 98%. Here, the whiteness is a color difference from a standard white plate, and was measured using SZ- # 80 manufactured by Nippon Denshoku Industries Co., Ltd. When the slurry after acid decomposition was dried as it was, it contained 36% of potassium chloride.
【００１４】比較例１Ｎ−ラウロイル−β−アラニンの製造 実施例１の酸分解反応後のＮ−ラウロイル−β−アラニ
ンの結晶を含むスラリー1158ｇを50℃に冷却し、濾過し
た。結晶を減圧乾燥（50℃、50mmHg) し、282ｇのＮ−
ラウロイル−β−アラニンを得た。塩化カリウム含量は
6.2％であり、白色度96％であった。Comparative Example 1 Production of N-lauroyl-β-alanine 1158 g of a slurry containing crystals of N-lauroyl-β-alanine after the acid decomposition reaction of Example 1 was cooled to 50 ° C. and filtered. The crystals were dried under reduced pressure (50 ° C, 50 mmHg) and 282 g of N-
Lauroyl-β-alanine was obtained. Potassium chloride content
The whiteness was 96%.
【００１５】実施例２〜５ アミノ酸、脂肪酸ハライド及びアルカリの種類を種々変
えて、実施例１と同様の実験を行った。結果を表１に示
す。Examples 2 to 5 The same experiment as in Example 1 was carried out with various kinds of amino acids, fatty acid halides and alkalis. Table 1 shows the results.
【００１６】[0016]
【表１】 [Table 1]
【００１７】実施例１〜５及び比較例１の結果から明ら
かなように、本発明によれば、アミノ酸水溶液へ、アル
カリの存在下に炭素数６〜22の脂肪酸ハライドを供給
し、得られるＮ−長鎖アシルアミノ酸アルカリ塩の合成
反応液を、鉱酸でpH１〜５に調整したものを、該Ｎ−長
鎖アシルアミノ酸の融解状態下で、水層とＮ−長鎖アシ
ルアミノ酸を含む有機層に分層することにより、無機塩
等の不純物を殆ど含まないＮ−長鎖アシルアミノ酸を濾
過等の晶析工程を用いることなく、また親水性溶媒等の
有機溶媒を使用することなく、工業的に有利に分離する
ことができた。As is clear from the results of Examples 1 to 5 and Comparative Example 1, according to the present invention, a fatty acid halide having 6 to 22 carbon atoms is supplied to an aqueous amino acid solution in the presence of an alkali to obtain N -A reaction solution for the synthesis of an alkali salt of a long-chain acylamino acid, which is adjusted to pH 1 to 5 with a mineral acid, is dissolved in an N-long-chain acylamino acid, and an aqueous layer and an organic solution containing the N-long-chain acylamino acid. By separating the layers into layers, N-long-chain acylamino acids containing almost no impurities such as inorganic salts can be industrially used without using a crystallization step such as filtration or using an organic solvent such as a hydrophilic solvent. It could be separated advantageously.
【００１８】実施例６ 20％の塩化ナトリウムを含有するＮ−ラウロイル−β−
アラニン 125部、及び水 200部を含む混合液を90℃に昇
温し、Ｎ−ラウロイル−β−アラニンを融解させた。同
温度で15分間静置し、分層させた。有機層を分離し、８
％の水分を含むＮ−ラウロイル−β−アラニン 108部を
得た。これを真空加熱 (120℃、200mmHg) により乾燥
し、 100部のＮ−ラウロイル−β−アラニンを得た。本
品の塩化ナトリウム含量は 0.5％であり、水分は 0.1
％、また、白色度は98％であった。EXAMPLE 6 N-Lauroyl-β-containing 20% of sodium chloride
A mixture containing 125 parts of alanine and 200 parts of water was heated to 90 ° C. to melt N-lauroyl-β-alanine. The mixture was allowed to stand at the same temperature for 15 minutes to separate layers. Separate the organic layer and add 8
Thus, 108 parts of N-lauroyl-β-alanine containing 0.1% of water were obtained. This was dried by heating under vacuum (120 ° C., 200 mmHg) to obtain 100 parts of N-lauroyl-β-alanine. The product has a sodium chloride content of 0.5% and a water content of 0.1
%, And the whiteness was 98%.
Claims (3)
炭素数６〜22の脂肪酸ハライドを添加して反応させ、得
られるＮ−長鎖アシルアミノ酸アルカリ塩の合成反応液
を鉱酸でpH１〜５に調整してＮ−長鎖アシルアミノ酸に
変換し、該Ｎ−長鎖アシルアミノ酸の融解状態下で、水
層とＮ−長鎖アシルアミノ酸を含む有機層に分層し、次
いで有機層より該Ｎ−長鎖アシルアミノ酸を分離取得す
ることを特徴とするＮ−長鎖アシルアミノ酸の分離法。An aqueous solution of an amino acid is reacted with a fatty acid halide having 6 to 22 carbon atoms in the presence of an alkali, and the resulting reaction solution for the synthesis of an alkali N-long-chain acylamino acid is adjusted to pH 1 to 5 with a mineral acid. To an N-long-chain acylamino acid, and under the melting state of the N-long-chain acylamino acid, separate into an aqueous layer and an organic layer containing the N-long-chain acylamino acid. A method for separating N-long-chain acyl amino acids, comprising separating and obtaining N-long-chain acyl amino acids.
アミノ酸を水と混合し、該Ｎ−長鎖アシルアミノ酸の融
解状態下で、水層とＮ−長鎖アシルアミノ酸を含む有機
層に分層し、次いで有機層より、高純度のＮ−長鎖アシ
ルアミノ酸を得ることを特徴とするＮ−長鎖アシルアミ
ノ酸の精製法。2. An N-long-chain acylamino acid containing impurities such as an inorganic salt is mixed with water, and an aqueous layer and an organic layer containing the N-long-chain acylamino acid are mixed under the molten state of the N-long-chain acylamino acid. A method for purifying N-long-chain acylamino acids, which comprises obtaining a high-purity N-long-chain acylamino acid from the organic layer.
−メチル−β−アラニンである請求項１記載の分離法。3. The method according to claim 2, wherein the amino acid is glycine, β-alanine, N
The method according to claim 1, which is -methyl-β-alanine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4313047A JP3025725B2 (en) | 1992-11-24 | 1992-11-24 | Method for separating and purifying N-long-chain acylamino acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4313047A JP3025725B2 (en) | 1992-11-24 | 1992-11-24 | Method for separating and purifying N-long-chain acylamino acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06157440A JPH06157440A (en) | 1994-06-03 |
| JP3025725B2 true JP3025725B2 (en) | 2000-03-27 |
Family
ID=18036569
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4313047A Expired - Lifetime JP3025725B2 (en) | 1992-11-24 | 1992-11-24 | Method for separating and purifying N-long-chain acylamino acids |
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| Country | Link |
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| JP (1) | JP3025725B2 (en) |
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| DK1334962T3 (en) | 2000-10-18 | 2007-12-10 | Ajinomoto Kk | Methods for preparing acylphenylalanine |
| EP2830438B1 (en) | 2012-03-30 | 2019-09-04 | Givaudan SA | N-acyl derivatives of gamma amino-butyric acid as food flavouring compounds, powder compositions containing them |
| CN106220546B (en) | 2012-03-30 | 2018-11-30 | 奇华顿股份有限公司 | N- acyl-proline derivative as food fragrance compound |
| KR102045590B1 (en) | 2012-03-30 | 2019-11-15 | 지보당 에스아 | N-acylated 1-aminocycloalkyl carboxylic acids as food flavouring compounds |
| EP2830439B1 (en) | 2012-03-30 | 2020-11-04 | Givaudan SA | N-acyl-gaba derivatives for the improvement of the flavour profile of edible compositions |
| CN104254253B (en) | 2012-03-30 | 2017-12-29 | 奇华顿股份有限公司 | N as food fragrance compound is acylated methionine derivatives |
| US10836712B2 (en) | 2012-03-30 | 2020-11-17 | Givaudan S.A. | Organic compounds |
| BR112014023448B1 (en) * | 2012-03-30 | 2021-06-22 | Givaudan Sa | EDIBLE OR DRINK COMPOSITION INCLUDING N-ACYL DERIVATIVES RANGE AMINO-BUTYRIC ACID AND STANDARD SOLUTION |
| US11122826B2 (en) | 2013-10-02 | 2021-09-21 | Givaudan Sa | Organic compounds |
| WO2015050535A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan S.A. | Organic compounds |
| WO2015048991A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan Sa | Organic compounds having taste-modifying properties |
| EP3057445B1 (en) | 2013-10-02 | 2018-07-04 | Givaudan SA | Organic compounds having taste-modifying properties |
| EP3057448B1 (en) | 2013-10-02 | 2017-12-06 | Givaudan S.A. | Organic compounds having taste-modifying properties |
| EP3057446B1 (en) | 2013-10-02 | 2017-12-06 | Givaudan S.A. | Organic compounds having taste-modifying properties |
| GB201317424D0 (en) | 2013-10-02 | 2013-11-13 | Givaudan Sa | Improvements in or relating to organic compounds |
| US10834950B2 (en) | 2013-10-02 | 2020-11-17 | Givaudan S.A. | Organic compounds |
| JP6507832B2 (en) * | 2015-05-07 | 2019-05-08 | 日油株式会社 | Method for producing N-acyl amino acid |
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1992
- 1992-11-24 JP JP4313047A patent/JP3025725B2/en not_active Expired - Lifetime
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| Publication number | Publication date |
|---|---|
| JPH06157440A (en) | 1994-06-03 |
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