JPH0761957A - Production of n-mixed saturated fatty acid acyl neutral amino acid - Google Patents
Production of n-mixed saturated fatty acid acyl neutral amino acidInfo
- Publication number
- JPH0761957A JPH0761957A JP21027293A JP21027293A JPH0761957A JP H0761957 A JPH0761957 A JP H0761957A JP 21027293 A JP21027293 A JP 21027293A JP 21027293 A JP21027293 A JP 21027293A JP H0761957 A JPH0761957 A JP H0761957A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- saturated fatty
- mixed saturated
- amino acid
- neutral amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、Ｎ−混合飽和脂肪酸ア
シル中性アミノ酸（グリシン、アラニン及びβ−アラニ
ン）の製造法に関し、さらに詳しくは、界面活性剤等と
して有用な高純度のＮ−混合飽和脂肪酸アシル中性アミ
ノ酸を高収率かつ製造経済的に有利な製造法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing N-mixed saturated fatty acid acyl neutral amino acids (glycine, alanine and β-alanine), and more specifically, a high-purity N-useful useful as a surfactant or the like. The present invention relates to a method for producing a mixed saturated fatty acid acyl neutral amino acid in high yield and economically advantageous.
【０００２】[0002]
【従来の技術及び本発明が解決しようとする課題】Ｎ−
アシルアミノ酸はそのアルカリ塩が優れた界面活性能と
静菌作用を有し、低刺激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。また、Ｎ−アシルア
ミノ酸は他の界面活性剤と併用すると優れた相乗効果を
示すことが知られている。一般に、これらＮ−アシルア
ミノ酸を製造するには、アミノ酸及びアルカリ物質を含
有する水溶液と脂肪酸ハライドとをショッテン・バウマ
ン反応により反応させた後、強酸を用いて中和、析出す
るＮ−アシルアミノ酸を濾別、洗浄する方法がとられて
いる。PRIOR ART AND PROBLEMS TO BE SOLVED BY THE INVENTION N-
Acyl amino acids are known to have low surface irritation, in which their alkali salts have excellent surfactant activity and bacteriostatic activity, and are used in various fields. Further, N-acyl amino acids are known to exhibit an excellent synergistic effect when used in combination with other surfactants. Generally, in order to produce these N-acyl amino acids, an aqueous solution containing an amino acid and an alkaline substance is reacted with a fatty acid halide by the Schotten-Baumann reaction, and then the N-acyl amino acid which is neutralized and precipitated with a strong acid is added. The method of filtering and washing is adopted.
【０００３】しかし、この方法では濾別された結晶に無
機塩が残存しやすく、無機塩を除去するために大量の洗
浄水を必要とし、洗浄に長時間を要するために製造経済
性が悪化するという問題があった。また、結晶の洗浄を
全くしないか、比較的少量の洗浄水を用いて洗浄した場
合、無機塩が大量に残存するため上記方法を用いて製造
したＮ−アシルアミノ酸を洗浄剤に配合すると、にごり
が生じやすくなったり、低温の安定性が悪くなるなどの
問題点が生じる。However, according to this method, the inorganic salt is likely to remain in the crystals separated by filtration, a large amount of washing water is required to remove the inorganic salt, and the washing requires a long time, which deteriorates the manufacturing economy. There was a problem. In addition, when the crystals are not washed at all or washed with a relatively small amount of washing water, a large amount of inorganic salt remains, and therefore N-acyl amino acid produced by the above method is blended in the detergent, resulting in turbidity. And the stability at low temperature becomes poor.
【０００４】アシルアミノ酸の中でも特に、グリシン、
アラニン、β−アラニンは濾過性の良い粒径で結晶を取
り上げることが困難で、従来のように結晶として一度取
り上げるといった操作自体が、大量の工業スケールでの
製造には不利となる。Among the acylamino acids, glycine,
It is difficult to pick up crystals of alanine and β-alanine with a particle size having good filterability, and the operation itself, such as once picking up as crystals, is disadvantageous for large-scale industrial scale production.
【０００５】特開平５−７０４１８号公報には、グリシ
ンおよびβ−アラニンを単一鎖長の脂肪酸ハライドと反
応させる場合、反応中和剤として水酸化ナトリウムを用
いると、反応液のゲル化等が起こり攪拌が困難となるた
め、水酸化カリウムを用いるとよいとの記載がある。ま
た、特開平４−３２１６５６号公報には、反応液の増粘
を抑制するため、脂肪酸クロライド中の低沸点物を留去
する方法が開示されている。しかしながら、これらの方
法においても上記の問題点は解決されておらず、高純
度、高収率、製造経済的に有利な製造法の開発が望まれ
ていた。JP-A-5-70418 discloses that when glycine and β-alanine are reacted with a fatty acid halide having a single chain length, if sodium hydroxide is used as a reaction neutralizing agent, gelation of the reaction solution may occur. It is described that potassium hydroxide should be used because it occurs and stirring becomes difficult. Further, JP-A-4-321656 discloses a method of distilling off a low boiling point substance in a fatty acid chloride in order to suppress thickening of a reaction liquid. However, the above problems have not been solved even by these methods, and development of a manufacturing method having high purity, high yield, and manufacturing economical advantage has been desired.
【０００６】[0006]
【問題を解決するための手段】このような実情におい
て、本発明者らは鋭意検討した結果、ショッテン・バウ
マン反応において、用いる脂肪酸ハライドを混合飽和脂
肪酸ハライドとすることによって、水酸化ナトリウム存
在下でもゲル化することなく容易に反応でき、更に強酸
により中和した後、６０℃以上に加熱することによって
有機層と水層とに分層し、有機層よりＮ−混合飽和脂肪
酸アシル中性アミノ酸を回収することにより、容易に高
純度のＮ−混合飽和脂肪酸アシル中性アミノ酸を製造で
きることを見出し本発明を完成した。[Means for Solving the Problems] Under such circumstances, as a result of intensive investigations by the present inventors, the fatty acid halide used in the Schotten-Baumann reaction was changed to a mixed saturated fatty acid halide, so that even in the presence of sodium hydroxide. It can be easily reacted without gelation, and after being neutralized with a strong acid, the organic layer and the aqueous layer are separated by heating at 60 ° C. or higher, and the N-mixed saturated fatty acid acyl neutral amino acid is separated from the organic layer. The present invention has been completed by finding that a highly pure N-mixed saturated fatty acid acyl neutral amino acid can be easily produced by recovering.
【０００７】すなわち、本発明は、グリシン、アラニン
またはβ−アラニンの水溶液に、炭素原子数６〜１８の
混合飽和脂肪酸ハライドを添加し、アルカリ存在下、反
応させてＮ−混合飽和脂肪酸アシル中性アミノ酸塩水溶
液を得（工程（１））、次いで、得られたＮ−混合飽和
脂肪酸アシル中性アミノ酸塩水溶液に強酸を添加し、６
０℃以上で有機層と水層とに分層し、有機層よりＮ−混
合飽和脂肪酸アシル中性アミノ酸を回収する（工程
（２））ことを特徴とするＮ−混合飽和脂肪酸アシル中
性アミノ酸の製造法に関するものである。That is, according to the present invention, a mixed saturated fatty acid halide having 6 to 18 carbon atoms is added to an aqueous solution of glycine, alanine or β-alanine, and the mixture is reacted in the presence of an alkali to give an N-mixed saturated fatty acid acyl neutral. An amino acid salt aqueous solution is obtained (step (1)), and then a strong acid is added to the obtained N-mixed saturated fatty acid acyl neutral amino acid salt aqueous solution,
An N-mixed saturated fatty acid acyl neutral amino acid characterized by being separated into an organic layer and an aqueous layer at 0 ° C. or higher, and recovering the N-mixed saturated fatty acid acyl neutral amino acid from the organic layer (step (2)). Of the manufacturing method of.
【０００８】以下、本発明について詳細に説明する。本
発明の工程（１）において使用される混合飽和脂肪酸ハ
ライドは、炭素原子数６〜１８である単一の飽和脂肪酸
を混合して得られる脂肪酸、またはやし油脂肪酸などの
天然の混合飽和脂肪酸もしくは混合不飽和脂肪酸の水素
添加物のハライドであって、その脂肪酸組成比は重量比
で（炭素原子数１２以下の飽和脂肪酸ハライド）／（炭
素原子数１３以上の飽和脂肪酸ハライド）＝１００／０
〜１０／９０、好ましくは９５／５〜２０／８０、特に
好ましくは８０／２０〜５０／５０である。脂肪酸の組
成比は、工程（２）において有機層と水層とに分層が可
能な範囲内でその組成を変化させることができる。炭素
原子数１２以下の飽和脂肪酸ハライドのみを用いる場合
には、ラウロイルハライドは９５％以下であることが必
須である。また混合脂肪酸ハライドには、本発明の目的
・効果を損なわない範囲で不飽和脂肪酸ハライドを含有
していてもよい。The present invention will be described in detail below. The mixed saturated fatty acid halide used in the step (1) of the present invention is a fatty acid obtained by mixing a single saturated fatty acid having 6 to 18 carbon atoms, or a natural mixed saturated fatty acid such as coconut oil fatty acid. Alternatively, it is a halide of a mixed unsaturated fatty acid hydrogenated product, and the fatty acid composition ratio thereof is (weighted saturated fatty acid halide having 12 or less carbon atoms) / (saturated fatty acid halide having 13 or more carbon atoms) = 100/0 by weight ratio.
10/90, preferably 95/5 to 20/80, and particularly preferably 80/20 to 50/50. The composition ratio of the fatty acid can be changed within the range in which the organic layer and the aqueous layer can be separated in the step (2). When only a saturated fatty acid halide having 12 or less carbon atoms is used, it is essential that the content of lauroyl halide is 95% or less. Further, the mixed fatty acid halide may contain an unsaturated fatty acid halide within a range that does not impair the objects and effects of the present invention.
【０００９】反応に用いられる中性アミノ酸はグリシ
ン、アラニン、β−アラニンから選ばれ、アラニンの場
合、光学活性体でもＤＬ体でもどちらでもよい。またア
シル化の反応比率は混合飽和脂肪酸ハライドに対して、
中性アミノ酸が１〜１．２当量であれば十分である。反
応は中性アミノ酸に水酸化ナトリウム、水酸化カリウム
等のアルカリを加え、ｐＨ９．５〜１２．５の水溶液と
し、ｐＨをアルカリ性に維持しつつ、脂肪酸ハライドと
水酸化ナトリウム等のアルカリを添加して行う。この
時、反応温度は４５℃以下としたほうが、脂肪酸ハライ
ドの分解が抑えられ好ましい。脂肪酸ハライドの滴加
後、０．１〜５時間攪拌して、反応を完結させる。The neutral amino acid used in the reaction is selected from glycine, alanine and β-alanine. In the case of alanine, either an optically active substance or a DL form may be used. The reaction ratio of acylation is based on the mixed saturated fatty acid halide,
It is sufficient if the neutral amino acid is 1 to 1.2 equivalents. The reaction is carried out by adding an alkali such as sodium hydroxide or potassium hydroxide to the neutral amino acid to prepare an aqueous solution having a pH of 9.5 to 12.5, and adding a fatty acid halide and an alkali such as sodium hydroxide while keeping the pH alkaline. Do it. At this time, it is preferable that the reaction temperature is 45 ° C. or lower because decomposition of the fatty acid halide is suppressed. After the fatty acid halide is added dropwise, the mixture is stirred for 0.1 to 5 hours to complete the reaction.
【００１０】次に塩酸、硫酸などの強酸を加えｐＨ４以
下とし中和した後、反応液を６０℃以上、好ましくは７
０〜９０℃に加熱することにより、Ｎ−混合飽和脂肪酸
アシル中性アミノ酸よりなる有機層と水層に分層させ
る。この時６０℃未満では分層しない。また、一度の分
層では塩などの不純物の淘汰が不十分で、有機層を繰り
返し洗浄する場合、その洗液のｐＨを５以下にすること
により洗浄が効率よく行える。ｐＨ５以上の水で洗浄を
行おうとすると、Ｎ−混合飽和脂肪酸アシル中性アミノ
酸が、その脂肪酸組成によっては水に溶解したり、乳化
してしまい、分層が効率よく行えない。洗液のｐＨ調整
剤としては、硫酸、塩酸、リン酸等の無機酸、及びクエ
ン酸等の有機酸で行うことができる。Next, a strong acid such as hydrochloric acid or sulfuric acid is added to neutralize the solution to pH 4 or lower, and then the reaction solution is heated to 60 ° C. or higher, preferably 7
By heating to 0 to 90 ° C., the organic layer and the aqueous layer composed of the N-mixed saturated fatty acid acyl neutral amino acid are separated. At this time, if the temperature is lower than 60 ° C, the layer is not separated. In addition, once the layers are separated, impurities such as salts are not sufficiently selected, and when the organic layer is repeatedly washed, the washing can be efficiently performed by setting the pH of the washing liquid to 5 or less. When washing is performed with water having a pH of 5 or more, the N-mixed saturated fatty acid acyl neutral amino acid may be dissolved or emulsified in water depending on its fatty acid composition, and the layer separation cannot be performed efficiently. As the pH adjuster for the washing liquid, inorganic acids such as sulfuric acid, hydrochloric acid and phosphoric acid, and organic acids such as citric acid can be used.
【００１１】本発明の製造法によって得られたＮ−混合
飽和脂肪酸アシル中性アミノ酸は、冷却固化させた後、
粉砕することによりフリー体として取り上げることもで
きるが、必要に応じて常法により無機塩または有機塩へ
と変換することにより、界面活性剤として利用すること
ができる。The N-mixed saturated fatty acid acyl neutral amino acid obtained by the production method of the present invention is cooled and solidified,
Although it can be taken up as a free form by crushing, it can be used as a surfactant by converting it into an inorganic salt or an organic salt by a conventional method, if necessary.
【００１２】[0012]
【実施例】以下に実施例を挙げて本発明を具体的に説明
するが、本発明はこれによって限定されるものではな
い。The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto.
【００１３】実施例１ Ｎ−混合飽和脂肪酸アシル−ＤＬ−アラニン・トリエタ
ノールアミン塩の製造 工程（１）：ＤＬ−アラニン９４ｇを水４５１ｍｌに溶
解させ、これに２７％水酸化ナトリウムを加えｐＨ１
１．３の水溶液とし、これに脂肪酸組成；Ｃ10：１０
％、Ｃ12：４０％、Ｃ14：４０％、Ｃ16：１０％の脂肪
酸クロライド２３４ｇを、２７％水酸化ナトリウム水溶
液を用いてｐＨを１１．３に調整しながら添加した。反
応温度は３０〜３５℃に保ち１時間かけて添加した。添
加終了後、温度を４５℃とし１時間攪拌した。 工程（２）（１）で得られた反応液を６０℃に加熱し、
硫酸６９ｇを徐々に滴下し、温度を８０℃とした。Ｎ−
混合飽和脂肪酸アシル−ＤＬ−アラニンの溶解後、下部
から分層した水層を抜き、活性剤濃度が３０％になるよ
うにトリエタノールアミン水溶液を加えて水溶液として
取り上げた。製品の純度は９２％、塩濃度（ｗｔ％）は
Ｃｌ：０．１％以下、ＳＯ4：０．１％以下であった。Example 1 Production of N-mixed saturated fatty acid acyl-DL-alanine triethanolamine salt Step (1): 94 g of DL-alanine was dissolved in 451 ml of water, and 27% sodium hydroxide was added thereto to adjust pH to 1.
1.3 aqueous solution with fatty acid composition; C 10 : 10
%, C 12 : 40%, C 14 : 40%, C 16 : 10% fatty acid chloride 234 g was added while adjusting the pH to 11.3 using a 27% aqueous sodium hydroxide solution. The reaction temperature was maintained at 30 to 35 ° C. and the addition was performed over 1 hour. After the addition was completed, the temperature was raised to 45 ° C. and the mixture was stirred for 1 hour. Heating the reaction solution obtained in step (2) (1) to 60 ° C.,
69 g of sulfuric acid was gradually added dropwise to bring the temperature to 80 ° C. N-
After the mixed saturated fatty acid acyl-DL-alanine was dissolved, the aqueous layer separated from the bottom was extracted, and an aqueous triethanolamine solution was added so that the concentration of the active agent was 30%, and the solution was taken as an aqueous solution. The purity of the product was 92%, and the salt concentration (wt%) was Cl: 0.1% or less and SO 4 : 0.1% or less.
【００１４】実施例２ Ｎ−混合飽和脂肪酸アシルグリシン・トリエタノールア
ミン塩の製造 工程（１）：グリシン７９ｇを水４６６ｍｌに溶解さ
せ、これに２７％水酸化ナトリウム１５５ｇを加えてグ
リシンナトリウム塩水溶液とし、これに脂肪酸組成；Ｃ
8：５％、Ｃ10：１０％、Ｃ12：６０％、Ｃ14：２０
％、Ｃ16：５％の酸クロライド２２１ｇを、２７％水酸
化ナトリウム水溶液を用いてｐＨを１１．２に調整しな
がら添加した。反応温度は２５℃に保ち０．５時間かけ
て添加した。添加終了後、温度を３０℃とし１時間攪拌
した。 工程（２）：反応液を５０℃に加熱し、硫酸６９ｇを徐
々に滴下し、温度を８５℃に上げた。Ｎ−混合飽和脂肪
酸アシルグリシンを溶解後、下部から分層した水層を抜
いた。さらに、抜いた水層と同量のｐＨ２．５に調整し
た硫酸水溶液を加え、再び８５℃として、同様に分層し
た水を抜いた。その後、活性剤濃度が３０％になるよう
にトリエタノールアミン及び水を加えて、水溶液として
取り上げた。製品の純度は９４％、塩濃度（ｗｔ％）は
Ｃｌ：０．１％、ＳＯ4：０．２％であった。Example 2 Production of N-mixed saturated fatty acid acylglycine / triethanolamine salt Step (1): 79 g of glycine was dissolved in 466 ml of water, and 155 g of 27% sodium hydroxide was added thereto to give a glycine sodium salt aqueous solution. , Fatty acid composition of this; C
8: 5%, C 10: 10%, C 12: 60%, C 14: 20
%, C 16 : 5% acid chloride (221 g) was added while adjusting the pH to 11.2 using a 27% aqueous sodium hydroxide solution. The reaction temperature was kept at 25 ° C., and the reaction was added over 0.5 hours. After the addition was completed, the temperature was raised to 30 ° C. and the mixture was stirred for 1 hour. Step (2): The reaction solution was heated to 50 ° C., 69 g of sulfuric acid was gradually added dropwise, and the temperature was raised to 85 ° C. After the N-mixed saturated fatty acid acylglycine was dissolved, the aqueous layer separated from the bottom was removed. Further, the same amount of sulfuric acid aqueous solution adjusted to pH 2.5 as that of the removed water layer was added, the temperature was again adjusted to 85 ° C., and the water similarly separated was removed. Then, triethanolamine and water were added so that the concentration of the activator was 30%, and the solution was taken up as an aqueous solution. The purity of the product is 94%, the salt concentration (wt%) is Cl: 0.1%, SO 4: was 0.2%.
【００１５】比較例１ 実施例２で用いた混合飽和脂肪酸クロライドの代わり
に、単一組成の脂肪酸であるラウロイルクロライドを用
い、水酸化ナトリウムの代わりに水酸化カリウムを用い
たところ、工程（２）で有機層と水層に分層できなかっ
た。Comparative Example 1 When the mixed saturated fatty acid chloride used in Example 2 was replaced with lauroyl chloride, which is a fatty acid having a single composition, and potassium hydroxide was used instead of sodium hydroxide, the step (2) Therefore, the organic layer and the aqueous layer could not be separated.
【００１６】実施例３ 実施例２と同様に工程（１）及び（２）を行った後、２
度目の洗浄の洗液をクエン酸を用いてｐＨ２．３とした
以外は同様に行った。製品の純度は９４％、塩濃度（ｗ
ｔ％）はＣｌ：０．１％、ＳＯ4：０．１％以下であっ
た。Example 3 After performing steps (1) and (2) in the same manner as in Example 2, 2
The same procedure was performed except that the washing solution for the second washing was adjusted to pH 2.3 with citric acid. Product purity is 94%, salt concentration (w
t) was Cl: 0.1% and SO 4 : 0.1% or less.
【００１７】比較例２ 実施例２と同様に反応させ、工程（１）及び（２）を行
った後、２度目の洗浄の洗液を水（ｐＨ６．０）とした
以外は同様に行ったが、有機層と水層の分層性が悪く、
分離不可能であった。Comparative Example 2 Reaction was carried out in the same manner as in Example 2, and after carrying out steps (1) and (2), the same procedure was carried out except that the washing liquid for the second washing was water (pH 6.0). However, the separation between the organic layer and the water layer is poor,
It was inseparable.
【００１８】比較例３ 実施例２と同様に工程（１）を行い、工程（２）のと
き、硫酸中和後、温度を５５℃としたところ、全く分層
せずクリーム状になった。Comparative Example 3 When the step (1) was carried out in the same manner as in Example 2 and the temperature was 55 ° C. after neutralization with sulfuric acid in the step (2), the layer was not separated at all and became a cream.
【００１９】実施例４ Ｎ−混合飽和脂肪酸アシルβ−アラニン・カリウム塩の
製造 工程（１）：β−アラニン９４ｇを水４５１ｍｌに溶解
させ、これに２７％水酸化ナトリウムを加えｐＨ１１．
３の水溶液とし、これに実施例２と同様の混合飽和脂肪
酸クロライド２２１ｇを、２７％水酸化ナトリウム水溶
液を用いてｐＨを１１．３に調整しながら添加した。反
応温度は３０〜３５℃に保ち１時間かけて添加した。添
加終了後、温度を４５℃とし１時間攪拌した。 工程（２）：工程（１）で得られた反応液を６０℃に加
熱し、硫酸６９ｇを徐々に滴下し、温度を７５℃とし
た。Ｎ−混合飽和脂肪酸アシルβ−アラニンの溶解後、
下部から分層した水層を抜き、抜いた水層と同量のｐＨ
２．０に調整した硫酸水溶液を加え、再び７５℃として
同様に分層した水層を抜いた。その後、活性剤濃度が３
０％になるように水酸化カリウム水溶液を加えて、水溶
液として取り上げた。製品の純度は９３％、塩濃度（ｗ
ｔ％）はＣｌ：０．１％以下、ＳＯ4：０．１％以下で
あった。Example 4 Production of N-mixed saturated fatty acid acyl β-alanine potassium salt Step (1): 94 g of β-alanine was dissolved in 451 ml of water, and 27% sodium hydroxide was added thereto to adjust the pH to 11.
221 g of the same mixed saturated fatty acid chloride as in Example 2 was added thereto while adjusting the pH to 11.3. The reaction temperature was maintained at 30 to 35 ° C. and the addition was performed over 1 hour. After the addition was completed, the temperature was raised to 45 ° C. and the mixture was stirred for 1 hour. Step (2): The reaction liquid obtained in the step (1) was heated to 60 ° C., 69 g of sulfuric acid was gradually added dropwise to bring the temperature to 75 ° C. After dissolution of the N-mixed saturated fatty acid acyl β-alanine,
Remove the separated water layer from the bottom and adjust the pH to the same level as the removed water layer.
A sulfuric acid aqueous solution adjusted to 2.0 was added, the temperature was again raised to 75 ° C., and the aqueous layer similarly separated was extracted. After that, the activator concentration is 3
An aqueous solution of potassium hydroxide was added to 0%, and the solution was taken as an aqueous solution. Product purity is 93%, salt concentration (w
t) was Cl: 0.1% or less and SO 4 : 0.1% or less.
【００２０】実施例５ Ｎ−混合飽和脂肪酸アシルグリシン・カリウム塩の製造 工程（１）：グリシン７９ｇを水４６６ｍｌに溶解さ
せ、これに２７％水酸化ナトリウムを加えｐＨ１１．０
の水溶液とし、これに脂肪酸組成；Ｃ10：２０％、
Ｃ12：７０％、Ｃ14：１０％の酸クロライド２１６ｇ
を、２７％水酸化ナトリウムを用いてｐＨ１１．０に調
整しながら添加した。反応温度は３０℃に保ち０．５時
間かけて添加した。添加終了後、温度を５０℃とし１時
間攪拌した。 工程（２）：工程（１）で得られた反応液を６０℃に加
熱し、硫酸６９ｇを徐々に添加し、温度を８５℃とし
た。Ｎ−混合飽和脂肪酸アシルグリシンの溶解後、下部
から分層した水層を抜いた。その後、活性剤濃度が３０
％になるように水酸化カリウム水溶液を加えて水溶液と
して取り上げた。製品の純度は９４％、塩濃度（ｗｔ
％）はＣｌ：０．２％、ＳＯ4：０．２％であった。Example 5 Production of N-mixed saturated fatty acid acylglycine / potassium salt Step (1): 79 g of glycine was dissolved in 466 ml of water, and 27% sodium hydroxide was added thereto to adjust pH to 11.0.
And a fatty acid composition; C 10 : 20%,
216 g of acid chloride having C 12 : 70% and C 14 : 10%
Was added while adjusting the pH to 11.0 with 27% sodium hydroxide. The reaction temperature was kept at 30 ° C. and the addition was continued for 0.5 hours. After the addition was completed, the temperature was raised to 50 ° C. and the mixture was stirred for 1 hour. Step (2): The reaction liquid obtained in the step (1) was heated to 60 ° C., 69 g of sulfuric acid was gradually added to bring the temperature to 85 ° C. After the N-mixed saturated fatty acid acylglycine was dissolved, the aqueous layer separated from the bottom was removed. After that, the activator concentration is 30
Aqueous potassium hydroxide solution was added so that the amount became 100%, and the solution was taken up as an aqueous solution. Product purity is 94%, salt concentration (wt
%) Was Cl: 0.2% and SO 4 : 0.2%.
【００２１】実施例６ Ｎ−混合飽和脂肪酸アシルβ−アラニン・トリエタノー
ルアミン塩の製造 工程（１）：β−アラニン９４ｇを水４５１ｍｌに溶解
させ、これに２７％水酸化ナトリウムを加え、ｐＨ１
１．３とし、これに混合脂肪酸（ＮＡＡ−４１５、日本
油脂（株）製、脂肪酸組成；Ｃ8：４％、Ｃ10：８％、
Ｃ12：６０％、Ｃ14：２５％、Ｃ16：３％）の酸クロラ
イド２２２ｇを２７％水酸化ナトリウム水溶液を用いて
ｐＨ１１．３に調整しながら添加した。反応温度は２５
〜３０℃に保ち、１．５時間で添加した。添加終了後、
温度を４０℃とし２時間攪拌した。 工程（２）：工程（１）で得られた反応液を６０℃に加
熱し、硫酸６９ｇを徐々に添加し、温度を８０℃とし
た。Ｎ−混合飽和脂肪酸アシルβ−アラニンの溶解後、
下部から分層した水層を抜き、それと同量のｐＨ２．６
に調整した塩酸水溶液を加え、再び８０℃として同様に
分層した水層を抜いた。その後、活性剤濃度が３０％に
なるようにトリエタノールアミン水溶液を加えて水溶液
として取り上げた。製品の純度は９２％、塩濃度（ｗｔ
％）はＣｌ：０．１％、ＳＯ4：０．１％以下であっ
た。Example 6 Production of N-mixed saturated fatty acid acyl β-alanine triethanolamine salt Step (1): 94 g of β-alanine was dissolved in 451 ml of water, and 27% sodium hydroxide was added thereto to adjust pH to 1.
1.3, and mixed fatty acid (NAA-415, manufactured by NOF CORPORATION), fatty acid composition; C 8 : 4%, C 10 : 8%,
222 g of acid chloride (C 12 : 60%, C 14 : 25%, C 16 : 3%) was added while adjusting the pH to 11.3 using 27% aqueous sodium hydroxide solution. Reaction temperature is 25
Keep at ~ 30 ° C and add in 1.5 hours. After the addition is complete
The temperature was raised to 40 ° C. and the mixture was stirred for 2 hours. Step (2): The reaction liquid obtained in the step (1) was heated to 60 ° C., 69 g of sulfuric acid was gradually added to bring the temperature to 80 ° C. After dissolution of the N-mixed saturated fatty acid acyl β-alanine,
The aqueous layer separated from the bottom is extracted, and the same amount of pH is 2.6.
The hydrochloric acid aqueous solution adjusted to was added, the temperature was again adjusted to 80 ° C., and the aqueous layer similarly separated was extracted. Then, an aqueous solution of triethanolamine was added so that the concentration of the activator was 30%, and the aqueous solution was taken up. Product purity is 92%, salt concentration (wt
%) Was Cl: 0.1% and SO 4 : 0.1% or less.
Claims (3)
特徴とするＮ−混合飽和脂肪酸アシル中性アミノ酸の製
造法。 工程（１）：グリシン、アラニンまたはβ−アラニンの
水溶液に、炭素原子数６〜１８の混合飽和脂肪酸ハライ
ドを添加し、アルカリ存在下、反応させてＮ−混合飽和
脂肪酸アシル中性アミノ酸塩水溶液を得る工程 工程（２）：得られたＮ−混合飽和脂肪酸アシル中性ア
ミノ酸塩水溶液に強酸を添加し、６０℃以上で有機層と
水層とに分層し、有機層よりＮ−混合飽和脂肪酸アシル
中性アミノ酸を回収する工程1. A method for producing an N-mixed saturated fatty acid acyl neutral amino acid, which comprises performing the following steps (1) and (2). Step (1): A mixed saturated fatty acid halide having 6 to 18 carbon atoms is added to an aqueous solution of glycine, alanine or β-alanine, and the mixture is reacted in the presence of an alkali to give an aqueous solution of an N-mixed saturated fatty acid acyl neutral amino acid salt. Step of Obtaining Step (2): A strong acid is added to the obtained aqueous solution of N-mixed saturated fatty acid acyl neutral amino acid salt, and the mixture is separated into an organic layer and an aqueous layer at 60 ° C. or higher. Step to recover acyl neutral amino acid
酸ハライドの組成が（炭素原子数１２以下の飽和脂肪酸
ハライド）／（炭素原子数１３以上の飽和脂肪酸ハライ
ド）＝１００／０〜１０／９０である請求項１記載の製
造法。2. The composition of the mixed saturated fatty acid halide used in the step (1) is (saturated fatty acid halide having 12 or less carbon atoms) / (saturated fatty acid halide having 13 or more carbon atoms) = 100/0 to 10/90. The method according to claim 1, wherein
さらにｐＨ５以下の水で水洗するＮ−混合飽和脂肪酸ア
シル中性アミノ酸の製造法。3. A method for producing an N-mixed saturated fatty acid acyl neutral amino acid, wherein the organic layer obtained by the production method according to claim 1 is further washed with water having a pH of 5 or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21027293A JP3362468B2 (en) | 1993-08-25 | 1993-08-25 | Process for producing N-mixed saturated fatty acyl neutral amino acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21027293A JP3362468B2 (en) | 1993-08-25 | 1993-08-25 | Process for producing N-mixed saturated fatty acyl neutral amino acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0761957A true JPH0761957A (en) | 1995-03-07 |
| JP3362468B2 JP3362468B2 (en) | 2003-01-07 |
Family
ID=16586650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21027293A Expired - Lifetime JP3362468B2 (en) | 1993-08-25 | 1993-08-25 | Process for producing N-mixed saturated fatty acyl neutral amino acids |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3362468B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006009320A1 (en) * | 2004-07-23 | 2006-01-26 | Ajinomoto Co., Inc. | Process for production of powdery n-(long-chain acyl)- amino acids or salts thereof, powdery n-(long-chain acyl)amino acids or salts thereof, and facial cleansing powders |
| EP2212278A2 (en) | 2007-11-20 | 2010-08-04 | Clariant Finance (BVI) Limited | Method for producing acylglycinates |
| CN114369036A (en) * | 2021-12-30 | 2022-04-19 | 广州花语精细化工有限公司 | Method for reducing amine byproducts in glycine surfactant |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2624026C2 (en) | 2012-08-23 | 2017-06-30 | Гэлакси Сёфэктентс Лтд. | Method of obtaining surface-active substances based on n-acylamine acid with the use of surface-active substances based on n-acylamine acid or the relevant anhydride as catalysts |
-
1993
- 1993-08-25 JP JP21027293A patent/JP3362468B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006009320A1 (en) * | 2004-07-23 | 2006-01-26 | Ajinomoto Co., Inc. | Process for production of powdery n-(long-chain acyl)- amino acids or salts thereof, powdery n-(long-chain acyl)amino acids or salts thereof, and facial cleansing powders |
| EP2212278A2 (en) | 2007-11-20 | 2010-08-04 | Clariant Finance (BVI) Limited | Method for producing acylglycinates |
| EP2248512A2 (en) * | 2007-11-20 | 2010-11-10 | Clariant Finance (BVI) Limited | Compounds containing acylglycinate |
| EP2212278B1 (en) * | 2007-11-20 | 2015-01-07 | Clariant Finance (BVI) Limited | Method for producing acylglycinates |
| CN114369036A (en) * | 2021-12-30 | 2022-04-19 | 广州花语精细化工有限公司 | Method for reducing amine byproducts in glycine surfactant |
| CN114369036B (en) * | 2021-12-30 | 2024-04-19 | 广州花语精细化工有限公司 | Method for reducing amine byproducts in glycine surfactant |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3362468B2 (en) | 2003-01-07 |
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