JP2744648B2 - Method for producing amino acid granules - Google Patents
Method for producing amino acid granulesInfo
- Publication number
- JP2744648B2 JP2744648B2 JP1167214A JP16721489A JP2744648B2 JP 2744648 B2 JP2744648 B2 JP 2744648B2 JP 1167214 A JP1167214 A JP 1167214A JP 16721489 A JP16721489 A JP 16721489A JP 2744648 B2 JP2744648 B2 JP 2744648B2
- Authority
- JP
- Japan
- Prior art keywords
- amino acid
- solution
- crystals
- tryptophan
- fatty acid
- 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.)
- Expired - Lifetime
Links
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Seasonings (AREA)
- Medicinal Preparation (AREA)
- Indole Compounds (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、アミノ酸水溶液に油脂類および糖脂肪酸エ
ステル類の一種または二種以上を添加し濃縮して該アミ
ノ酸の結晶を顆粒として取得する方法に関する。Description: TECHNICAL FIELD The present invention relates to a method for adding one or more kinds of fats and oils and sugar fatty acid esters to an aqueous amino acid solution, concentrating the solution, and obtaining crystals of the amino acid as granules.
従来の技術 アミノ酸の顆粒化関連技術としては、トリプトファン
またはスレオニンを含む溶液を噴霧乾燥し、半乾燥状態
の噴霧顆粒としてマット状で熱風乾燥し顆粒化する方法
（特開昭63−102641号公報）、トリプトファンをエチル
セルロースによりマイクロカプセル化する方法（特開昭
61−152623号公報）などが知られている。2. Description of the Related Art As a technique related to granulation of amino acids, a method of spray-drying a solution containing tryptophan or threonine and hot-air drying in a mat form as a spray granule in a semi-dry state to granulate (Japanese Patent Laid-Open No. 63-102641) For microencapsulation of tryptophan with ethylcellulose
61-152623) and the like.
発明が解決しようとする問題点 従来の技術は、いずれも一旦結晶を取得した後に、ま
たは乾燥した後、マイクロカプセル化あるいは顆粒化す
るものであり、特殊な乾燥機や有機溶媒の除去などの顆
粒化設備を必要とし、工業化が難しい。Problems to be Solved by the Invention All of the conventional techniques involve microencapsulation or granulation after once obtaining crystals or after drying, and granulation such as removal of a special dryer or an organic solvent. It requires industrial equipment and is difficult to industrialize.
問題点を解決するための手段 本発明は、アミノ酸の水溶液に油脂類および糖脂肪酸
エステル類を添加して濃縮することにより、該アミノ酸
の結晶を顆粒として取得することができることを見出し
本発明を完成した。Means for Solving the Problems The present invention has been found that crystals of the amino acid can be obtained as granules by adding an oil or fat and a sugar fatty acid ester to an aqueous solution of the amino acid and concentrating the same, thereby completing the present invention. did.
以下本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明は、アミノ酸水溶液に油脂類および糖脂肪酸エ
ステル類から選ばれる一種または二種以上を添加し濃縮
して該アミノ酸の結晶を顆粒として取得することを特徴
とする。The present invention is characterized in that one or more selected from fats and oils and sugar fatty acid esters are added to an aqueous amino acid solution and concentrated to obtain crystals of the amino acid as granules.
本発明で使用するアミノ酸水溶液は、トリプトファ
ン、バリン、イソロイシン、スレオニン、フェニルアラ
ニン、ヒスチジン、リジンなどのアミノ酸のいずれか一
種類を溶液中の固形物当り10〜100％、好ましくは30〜1
00％含む水溶液であればよく、微生物の培養液、その除
菌液、イオン交換樹脂吸着溶離液、晶析母液、酵素反応
液などが含まれる。The aqueous amino acid solution used in the present invention may contain any one of amino acids such as tryptophan, valine, isoleucine, threonine, phenylalanine, histidine, and lysine in an amount of 10 to 100%, preferably 30 to 1%, per solid in the solution.
Any aqueous solution containing 00% may be used, and examples include a culture solution of a microorganism, a bacteria elimination solution thereof, an ion exchange resin adsorption / elution solution, a crystallization mother liquor, and an enzyme reaction solution.
油脂類としては動植物油脂、例えば、牛酪脂、ヤシ
油、パーム核油などが使用でき、糖脂肪酸エステル類と
しては、例えば、ショ糖ラウリン酸エステル、ショ糖ス
テアリン酸エステル、α−メチルグルコースラウリン酸
ジエステルなどが使用できる。これらは、一種または二
種以上の混合物として使用できる。Animal fats and oils such as beef butterfat, coconut oil and palm kernel oil can be used as the fats and oils, and sugar fatty acid esters such as sucrose laurate, sucrose stearate, α-methylglucose laurate Diesters and the like can be used. These can be used as one kind or as a mixture of two or more kinds.
油脂類および糖脂肪酸エステル類の添加量は、油脂類
がアミノ酸に対して0.5〜30％（w/w）、好ましくは２〜
７％（w/w）であり、糖脂肪酸エステル類がアミノ酸に
対して0.01〜1.0％（w/w）、好ましくは0.05〜0.5％（w
/w）である。これらの添加映は、そのままあるいは10〜
20％（w/w）となるようあらかじめ水に懸濁後アミノ酸
水溶液に加える。The amount of fats and oils and sugar fatty acid esters added is 0.5 to 30% (w / w), preferably
7% (w / w), and the amount of the sugar fatty acid ester relative to the amino acid is 0.01 to 1.0% (w / w), preferably 0.05 to 0.5% (w / w).
/ w). These additive films can be used as they are or
After suspending in water in advance so that the concentration becomes 20% (w / w), the suspension is added to the amino acid aqueous solution.
該添加物を含むアミノ酸水溶液を減圧下（700〜750mm
Hg）30〜50℃で濃縮することにより本発明の顆粒を得る
ことができる。The amino acid aqueous solution containing the additive is removed under reduced pressure (700 to 750 mm
Hg) The granules of the present invention can be obtained by concentration at 30 to 50 ° C.
以下、本発明を実施例および参考例によりさらに詳細
に説明する。Hereinafter, the present invention will be described in more detail with reference to Examples and Reference Examples.
実施例１ Ｌ−トリプトファン発酵液（特開昭60−176593号公報
実施例４の方法で製造したもの）２を強酸性イオン交
換樹脂 ダイヤイオンSK−1B（三菱化成社製）１に通して、Ｌ
−トリプトファンを吸着させた後、水で樹脂を充分洗浄
してから１規定アンモニア水溶液２でＬ−トリプトフ
ァンを溶離した。この溶離液を２倍濃縮してアンモニア
を除去し、濃塩酸でpH5.5に調整した。Example 1 An L-tryptophan fermented solution (produced by the method of Example 4 in JP-A-60-176593) 2 was passed through a strongly acidic ion-exchange resin Diaion SK-1B (manufactured by Mitsubishi Kasei) 1 L
After adsorbing tryptophan, the resin was sufficiently washed with water, and then L-tryptophan was eluted with 1N aqueous ammonia solution 2. The eluate was concentrated twice to remove ammonia, and adjusted to pH 5.5 with concentrated hydrochloric acid.
この濃縮液１〔トリプトファン含量3.0％（w/v）〕
のとり、精製ヤシ油（不二製油株式会社製）1.5gおよび
ショ糖ステアリン酸エステルＳ−570（三菱化成食品株
式会社製）0.015gを添加し、充分撹拌した。減圧下（70
0〜750mmHg）、30〜40℃で0.17まで濃縮し、20℃以下
まで冷却して結晶を熟成させた。これを遠心分離し、水
50mlを噴霧して洗浄した。得られた結晶（付着水分40
％）を60℃で水分が無くなるまで乾燥して、Ｌ−トリプ
トファン顆粒状結晶26.4g（収率85.6％、純度97.4％）
を得た。This concentrated solution 1 [tryptophan content 3.0% (w / v)]
1.5 g of refined coconut oil (Fuji Oil Co., Ltd.) and 0.015 g of sucrose stearic acid ester S-570 (Mitsubishi Kasei Food Co., Ltd.) were added, and the mixture was sufficiently stirred. Under reduced pressure (70
The solution was concentrated to 0.17 at 30 to 40 ° C and cooled to 20 ° C or lower to mature the crystals. This is centrifuged and the water
50 ml was sprayed and washed. Obtained crystal (attached water 40
%) Was dried at 60 ° C. until there was no more water, and 26.4 g of L-tryptophan granular crystals (yield 85.6%, purity 97.4%)
I got
実施例２ 実施例１と同様に濃縮液を得た後、この１〔トリプ
トファン含量3.0％（w/v）〕をとりα−メチルグリコー
スラウリン酸ジエステルを主成分とする糖脂肪酸エステ
ル＊（HODAG Chemical Corp.製CB−６）0.15gを添加
し、充分撹拌した。以下実施例１と同様に0.17まで濃
縮し、冷却して結晶を熟成し、これを遠心分離し、水50
mlを噴霧して洗浄した。得られた結晶（付着水分45％）
を60℃で水分が無くなるまで乾燥して、Ｌ−トリプトフ
ァン顆粒状結晶26.1g（収率85.9％，純度98.7％）を得
た。Example 2 After obtaining a concentrated solution in the same manner as in Example 1, 1 (tryptophan content: 3.0% (w / v)) was taken, and a sugar fatty acid ester containing α-methylglycose laurate diester as a main component * (HODAG Chemical 0.15 g of Corp. CB-6) was added, and the mixture was sufficiently stirred. Thereafter, the mixture was concentrated to 0.17 in the same manner as in Example 1 and cooled to mature the crystals.
ml was sprayed and washed. Obtained crystal (attached water 45%)
Was dried at 60 ° C. until there was no more water to obtain 26.1 g of L-tryptophan granular crystals (yield 85.9%, purity 98.7%).
＊HODAG CB−６は、α−メチルグルコースとラウリン酸
を主体とするヤシ油脂肪酸のジエステルであり、米国に
おいて砂糖の晶出時に粘度低下を目的に使用されている
（US.Patent ＃2871,148）。* HODAG CB-6 is a diester of coconut oil fatty acid mainly composed of α-methylglucose and lauric acid, and is used in the United States for the purpose of decreasing the viscosity during crystallization of sugar (US Patent # 2871,148). ).
実施例３ Ｌ−イソロイシン発酵液（特開昭62−195293号公報）
２を遠心分離により菌体分離し、イソロイシンの除菌
溶液を得た。この除菌溶液をイソロイシン含量3.0％（w
/v）まで濃縮した。Example 3 L-isoleucine fermentation broth (JP-A-62-195293)
2 was separated by centrifugation to obtain a sterilized solution of isoleucine. The sterilized solution was treated with an isoleucine content of 3.0% (w
/ v).
この濃縮液１に粉末活性炭3.0を添加し、60℃30分
間脱色後過して脱色液を得た。この脱色液に精製ヤシ
油1.2gおよびショ糖ステアリン酸エステル0.012gを添加
し、充分撹拌した。減圧下（700〜750mmHg）、30〜40℃
で0.12まで濃縮し、20℃以下まで冷却して結晶を熟成
させた。これを遠心分離し、水50mlを噴霧して洗浄し
た。得られた結晶（付着水分30％）を60℃で水分が無く
なるまで乾燥して、Ｌ−イソロイシン顆粒状結晶31.9g
（収率90.5％、純度85.1％）を得た。Activated carbon powder 3.0 was added to the concentrate 1, and the mixture was decolorized at 60 ° C. for 30 minutes to obtain a decolorized liquid. 1.2 g of purified coconut oil and 0.012 g of sucrose stearic acid ester were added to the decolorized solution, followed by sufficient stirring. Under reduced pressure (700 ~ 750mmHg), 30 ~ 40 ℃
To 0.12, and cooled to 20 ° C. or lower to mature the crystals. This was centrifuged and washed by spraying 50 ml of water. The obtained crystal (adhered water 30%) was dried at 60 ° C. until the water disappeared, and 31.9 g of L-isoleucine granular crystal was obtained.
(Yield 90.5%, purity 85.1%).
参考例１ 実施例１と同様に濃縮液を得た後、この１〔トリプ
トファン含量3.0％（w/v）〕をとり、減圧下（700〜750
mmHg）、30〜40℃で0.2まで濃縮し、20℃以下まで冷
却して結晶を熟成させた。これを遠心分離し、水50mlを
噴霧して洗浄した。得られた結晶（付着水分60％）を60
℃で水分が無くなるで乾燥して、Ｌ−トリプトファン粉
末状結晶24.9g（収率81.8％，純度98.6％）を得た。Reference Example 1 A concentrated solution was obtained in the same manner as in Example 1, and this 1 [tryptophan content: 3.0% (w / v)] was taken and subjected to reduced pressure (700 to 750).
mmHg), concentrated at 30-40 ° C to 0.2 and cooled to 20 ° C or less to mature the crystals. This was centrifuged and washed by spraying 50 ml of water. The obtained crystals (adhesion moisture 60%)
Drying was carried out at ℃ without moisture to obtain 24.9 g of L-tryptophan powdery crystals (yield 81.8%, purity 98.6%).
参考例２ 実施例３と同様に脱色液を得た後、この脱色液を減圧
下（700〜750mmHg）、30〜40℃で0.15まで濃縮し20℃
以下まで冷却して結晶を熟成させた。これを遠心分離し
たが、微細結晶が多く結晶を得ることはできなかった。Reference Example 2 After obtaining a decolorized solution in the same manner as in Example 3, the decolorized solution was concentrated under reduced pressure (700 to 750 mmHg) at 30 to 40 ° C. to 0.15, and concentrated at 20 ° C.
The crystals were cooled to the following to age the crystals. This was centrifuged, but many fine crystals could not be obtained.
以上実施例と参考例で得られる結晶の濃縮度、結晶化
率、晶出スラリー粘度の結果を第１表に示す。Table 1 shows the results of the crystal concentration, crystallization ratio, and crystallization slurry viscosity obtained in the above Examples and Reference Examples.
発明の効果 本発明によってアミノ酸を顆粒化することにより、晶
出スラリー粘度を低下させ、濃縮度、結晶化率を向上さ
せ、また分離結晶の含水率を低下させ、乾燥製の改善お
よび乾燥品の粉塵減少をはかることができ、アミノ酸の
顆粒を工業的に安価に製造することができる。 Effect of the Invention By granulating an amino acid according to the present invention, the viscosity of the crystallized slurry is reduced, the concentration, the crystallization rate is improved, and the water content of the separated crystals is reduced, and the dried product is improved and the dried product is reduced. Dust can be reduced, and granules of amino acids can be industrially manufactured at low cost.
第１図は、参考例１で得られたＬ−トリプトファン粉末
状結晶の写真である。 第２図は、実施例１で得られたＬ−トリプトファン顆粒
状結晶の写真である。 第３図は、実施例２で得られたＬ−トリプトファン顆粒
状結晶の写真である。 第４図は、実施例３で得られたＬ−イソロイシン顆粒状
結晶の写真である。 いずれも倍率50倍の写真である。FIG. 1 is a photograph of L-tryptophan powdery crystals obtained in Reference Example 1. FIG. 2 is a photograph of L-tryptophan granular crystals obtained in Example 1. FIG. 3 is a photograph of L-tryptophan granular crystals obtained in Example 2. FIG. 4 is a photograph of L-isoleucine granular crystals obtained in Example 3. Each is a photograph with a magnification of 50 times.
フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ａ６１Ｋ 9/16 Ａ６１Ｋ 9/16 Ｒ 31/195 31/195 47/26 47/26 Ａ 47/44 47/44 Ａ Continued on the front page (51) Int.Cl. 6 Identification code FI A61K 9/16 A61K 9/16 R 31/195 31/195 47/26 47/26 A 47/44 47/44 A
Claims (6)
ステル類から選ばれる一種または二種以上を添加し、濃
縮して該アミノ酸の結晶を顆粒として取得することを特
徴とするアミノ酸顆粒の製造法。1. A process for producing amino acid granules, comprising adding one or more selected from fats and oils and sugar fatty acid esters to an aqueous amino acid solution, and concentrating the resultant to obtain crystals of the amino acid as granules.
イソロイシン、スレオニン、フェニルアラニン、ヒスチ
ジンおよびリジンから選ばれる、請求項１記載の製造
法。2. The method according to claim 2, wherein the amino acid is tryptophan, valine,
The method according to claim 1, wherein the method is selected from isoleucine, threonine, phenylalanine, histidine and lysine.
脂から選ばれる請求項１記載の製造法。3. The method according to claim 1, wherein the fats and oils are selected from coconut oil, palm kernel oil and beef tallow.
エステル、ショ糖ステアリン酸エステルおよびα−メチ
ルグルコースラウリン酸ジエステルから選ばれる、請求
項１記載の製造法。4. The process according to claim 1, wherein the sugar fatty acid esters are selected from sucrose laurate, sucrose stearate and α-methylglucose laurate diester.
〜30％（w/w）である、請求項１記載の製造法。5. The method according to claim 1, wherein the amount of the fat or oil is 0.5 to the amino acid.
The method according to claim 1, wherein the amount is about 30% (w / w).
に対して0.01〜1.0％（w/w）である、請求項１記載の製
造法。6. The method according to claim 1, wherein the amount of the sugar fatty acid ester is 0.01 to 1.0% (w / w) based on the amino acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1167214A JP2744648B2 (en) | 1989-06-29 | 1989-06-29 | Method for producing amino acid granules |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1167214A JP2744648B2 (en) | 1989-06-29 | 1989-06-29 | Method for producing amino acid granules |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0347160A JPH0347160A (en) | 1991-02-28 |
| JP2744648B2 true JP2744648B2 (en) | 1998-04-28 |
Family
ID=15845544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1167214A Expired - Lifetime JP2744648B2 (en) | 1989-06-29 | 1989-06-29 | Method for producing amino acid granules |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2744648B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW394686B (en) * | 1991-10-07 | 2000-06-21 | Otsukapharmaceutical Co Ltd | An enteral feeding nutritional composition having anticancer effects |
| US9227916B2 (en) * | 2011-09-12 | 2016-01-05 | Kyowa Hakko Bio Co., Ltd. | Process for producing amino acid |
| WO2017159708A1 (en) * | 2016-03-16 | 2017-09-21 | 味の素株式会社 | Composition with reduced off-flavor and method for producing same |
-
1989
- 1989-06-29 JP JP1167214A patent/JP2744648B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0347160A (en) | 1991-02-28 |
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