JP3169433B2 - Method for purifying N-phenylglycine - Google Patents
Method for purifying N-phenylglycineInfo
- Publication number
- JP3169433B2 JP3169433B2 JP14712392A JP14712392A JP3169433B2 JP 3169433 B2 JP3169433 B2 JP 3169433B2 JP 14712392 A JP14712392 A JP 14712392A JP 14712392 A JP14712392 A JP 14712392A JP 3169433 B2 JP3169433 B2 JP 3169433B2
- Authority
- JP
- Japan
- Prior art keywords
- phenylglycine
- chelating agent
- acid
- activated carbon
- crude
- 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 - Fee Related
Links
Description
【０００１】[0001]
【産業上の利用分野】本発明は染料中間体や光硬化樹脂
開始組成物として重要なＮ−フェニルグリシンの精製方
法に関するものである。The present invention relates to a method for purifying N-phenylglycine which is important as a dye intermediate or a photocurable resin starting composition.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】Ｎ−フ
ェニルグリシンは通常、アニリンとモノクロル酢酸とを
反応して得られる。こうして得られる粗製のＮ−フェニ
ルグリシンは純度９５〜９７％であり、また、茶色に着
色している。さらに無機のイオン成分であるナトリウム
イオン、カリウムイオン、カルシウムシオン、鉄イオン
等を１００〜５００ｐｐｍ含んでいる。そのために、高
純度の染料製造や光硬化樹脂開始組成物を目的とした場
合には、精製する必要があった。そこで、水にて再結晶
方法を試みたが、着色成分とイオン成分の除去は十分で
はなく、改良しなければならないことを確認した。2. Description of the Related Art N-phenylglycine is usually obtained by reacting aniline with monochloroacetic acid. The crude N-phenylglycine thus obtained has a purity of 95-97% and is colored brown. Further, it contains 100 to 500 ppm of inorganic ion components such as sodium ion, potassium ion, calcium ion, and iron ion. Therefore, when a high-purity dye production or a photocurable resin starting composition was intended, purification was necessary. Therefore, a recrystallization method was tried with water, but it was confirmed that the removal of the coloring component and the ionic component was not sufficient, and that the solution had to be improved.
【０００３】[0003]
【発明を解決するための手段】本発明者らは、上記課題
を解決すべく、鋭意検討した結果、活性炭及びキレート
剤処理の２つの手法を組み合わせることにより、高純度
で無色であり、かつイオン成分の非常に少ないＮ−フェ
ニルグリシンを得ることに成功し、本発明を完成した。
すなわち、本発明は粗製のＮ−フェニルグリシンを水に
て再結晶する際に、活性炭及びキレート剤を添加するこ
とを特徴とするＮ−フェニルグリシンの精製方法であ
る。Means for Solving the Problems The present inventors have conducted intensive studies in order to solve the above-mentioned problems, and as a result, by combining the two methods of activated carbon and chelating agent treatment, they have high purity, colorlessness, The inventors have succeeded in obtaining N-phenylglycine having a very small amount of components, and have completed the present invention.
That is, the present invention is a method for purifying N-phenylglycine, which comprises adding activated carbon and a chelating agent when recrystallizing crude N-phenylglycine with water.
【０００４】以下、本発明を詳細に説明する。本発明に
おいて使用する粗製のＮ−フェニルグリシンは、通常、
アニリンとモノクロル酢酸の反応によって得られる。本
発明においては、こうして得られたＮ−フェニルグリシ
ンを、水により再結晶する。Hereinafter, the present invention will be described in detail. The crude N-phenylglycine used in the present invention is usually
Obtained by the reaction of aniline with monochloroacetic acid. In the present invention, the N-phenylglycine thus obtained is recrystallized with water.
【０００５】使用する水の量は粗製Ｎ−フェニルグリシ
ンの量の５〜２０重量倍でよく、溶解の際、昇温は任意
に行えるが、６０〜１００℃、好ましくは８０〜９５℃
で行うとよい。又、使用する水はイオン成分の少ない蒸
留水を用いるのが好ましい。The amount of water to be used may be 5 to 20 times by weight the amount of crude N-phenylglycine, and the temperature can be arbitrarily raised during dissolution, but is preferably 60 to 100 ° C, preferably 80 to 95 ° C.
It is good to do in. Further, it is preferable to use distilled water containing a small amount of ionic components.
【０００６】本発明において、水にて再結晶する際、活
性炭及びキレート剤を添加する。添加は粗製Ｎ−フェニ
ルグリシンを水に溶解の際か、溶解後のいずれでもよ
く、又、活性炭、キレート剤の添加の順序も特に限定さ
れないが、粗製Ｎ−フェニルグリシンを溶解したのち、
両者を添加する方が操作を円滑に行うことができる。In the present invention, when recrystallizing with water, activated carbon and a chelating agent are added. The addition may be carried out either when the crude N-phenylglycine is dissolved in water or after dissolving, and the order of addition of the activated carbon and the chelating agent is not particularly limited, but after dissolving the crude N-phenylglycine,
The operation can be performed more smoothly by adding both.
【０００７】本発明において活性炭は、市販されている
いずれの種類のものも使用できる。又、活性炭の量は粗
製Ｎ−フェニルグリシンに対して通常３〜３０重量％、
好ましくは５〜１５重量％が適量である。３０重量％を
超えると収率が低下し、３重量％未満では精製に十分で
ない場合がある。In the present invention, any type of commercially available activated carbon can be used. The amount of activated carbon is usually 3 to 30% by weight based on crude N-phenylglycine,
Preferably, an appropriate amount is 5 to 15% by weight. If it exceeds 30% by weight, the yield decreases, and if it is less than 3% by weight, purification may not be sufficient.
【０００８】キレート剤は金属封鎖剤として知られてい
る各種のものが使用できる。これらの例として、具体的
にはトリエチレングリコール等のポリエチレングリコー
ル系、１，２−ジアミノベンゼン等のジアミン系、サル
チル酸等のヒドロキシカルボン酸系、１８−クラウン−
６等のクラウンエーテル系、多酢酸系等が挙げられる
が、中でも工業的見地から多酢酸系のものが好ましく、
これらの例としてはエチレンジアミン−Ｎ，Ｎ，Ｎ’，
Ｎ’−テトラ酢酸、Ｎ−（ヒドロキシエチル）−エチレ
ンジアミン−Ｎ，Ｎ’，Ｎ’−トリ酢酸、ジエチレント
リアミン−Ｎ，Ｎ，Ｎ’，Ｎ”，Ｎ”−ペンタ酢酸、ニ
トリロトリ酢酸及びそれらのナトリウム塩等が挙げられ
る。Various chelating agents known as sequestering agents can be used. Specific examples thereof include polyethylene glycols such as triethylene glycol, diamines such as 1,2-diaminobenzene, hydroxycarboxylic acids such as salicylic acid, and 18-crown-.
6, such as crown ether type, polyacetic acid type and the like, among which polyacetic acid type is preferable from an industrial viewpoint,
Examples of these are ethylenediamine-N, N, N ',
N'-tetraacetic acid, N- (hydroxyethyl) -ethylenediamine-N, N ', N'-triacetic acid, diethylenetriamine-N, N, N', N ", N" -pentaacetic acid, nitrilotriacetic acid and their sodium And the like.
【０００９】キレート剤の使用量は粗製Ｎ−フェニルグ
リシンに対して３〜３０重量％、好ましくは５〜２０重
量％が適量である。The amount of the chelating agent used is 3 to 30% by weight, preferably 5 to 20% by weight, based on the crude N-phenylglycine.
【００１０】活性炭、キレート剤を添加後は攪拌し、熱
時ろ過後、常法に従い、冷却、ろ過し、精Ｎ−フェニル
グリシンを得る。After adding activated carbon and a chelating agent, the mixture is stirred, filtered while hot, and cooled and filtered according to a conventional method to obtain purified N-phenylglycine.
【００１１】[0011]
【実施例】以下に実施例によって本発明をさらに詳しく
説明する。なお、実施例中の「部」は重量部を示す。The present invention will be described in more detail with reference to the following examples. In addition, "part" in an Example shows a weight part.
【００１２】実施例１ 蒸留水７００部に粗製Ｎ−フェニルグリシン７０部を入
れ９５℃に昇温し完全に溶解させた後、活性炭７部、ニ
トリロトリ酢酸モノナトリウム塩１０部を加え、９５℃
にて１時間攪拌した後、同温度で熱時ろ過した。ろ液を
２０℃まで冷却して、析出した結晶をろ過し、１００部
の蒸留水で洗浄した後、乾燥して５０部の精製Ｎ−フェ
ニルグリシンを得た。粗製Ｎ−フェニルグリシンと上で
得た精製Ｎ−フェニルグリシンの分析結果を第１表（表
１）に示す。Example 1 70 parts of crude N-phenylglycine was placed in 700 parts of distilled water, heated to 95 ° C. and completely dissolved, and then 7 parts of activated carbon and 10 parts of nitrilotriacetic acid monosodium salt were added.
After stirring at for 1 hour, the mixture was filtered while hot at the same temperature. The filtrate was cooled to 20 ° C., and the precipitated crystals were filtered, washed with 100 parts of distilled water, and dried to obtain 50 parts of purified N-phenylglycine. The analysis results of the crude N-phenylglycine and the purified N-phenylglycine obtained above are shown in Table 1 (Table 1).
【００１３】[0013]
【表１】 [Table 1]
【００１４】実施例２〜８ 実施例１において、キレート剤を代えて全く同様にて行
った結果を第２表（表２）に示すが、実施例１同様、良
好な結果が得られた。Examples 2 to 8 Table 2 (Table 2) shows the results obtained in the same manner as in Example 1 except that the chelating agent was changed. As in Example 1, good results were obtained.
【００１５】[0015]
【表２】 [Table 2]
【００１６】比較例１ 実施例１において、活性炭及びキレート剤であるニトリ
ロトリ酢酸モノナトリウム塩を添加しないで全く同様に
して行った。収率は７１％であったが、結晶色が茶色
で、純度は９８．１％、イオン成分はＮａ+が２８ｐｐ
ｍ、Ｋ+が１２ｐｐｍ、Ｃａ2+が４５ｐｐｍ、Ｆｅ3+が
２９ｐｐｍと不良であった。Comparative Example 1 The procedure of Example 1 was repeated except that activated carbon and monosodium nitrilotriacetic acid as a chelating agent were not added. The yield was 71%, the crystal color brown, purity 98.1% ion component is Na + 28pp
m and K + were 12 ppm, Ca 2+ was 45 ppm, and Fe 3+ was 29 ppm, which was poor.
【００１７】比較例２ 実施例１において、キレート剤であるニトリロトリ酢酸
モノナトリウム塩を添加しないで全く同様にして行っ
た。収率は６９％、純度９９．２％、白色結晶が得られ
たが、イオン成分はＮａ+が３５ｐｐｍ、Ｋ+が１６ｐｐ
ｍ、Ｃａ2+が５４ｐｐｍ、Ｆｅ3+が４５ｐｐｍと不良で
あった。Comparative Example 2 The procedure of Example 1 was repeated, except that the monosodium salt of nitrilotriacetic acid as a chelating agent was not added. The yield was 69%, the purity was 99.2%, and white crystals were obtained. The ion components were 35 ppm of Na + and 16 pp of K +.
m, Ca 2+ was 54 ppm and Fe 3+ was 45 ppm, which was poor.
【００１８】比較例３ 実施例１において、活性炭を添加しないで、全く同様に
して行った。収率は７０％、イオン成分はＮａ+が１．
９ｐｐｍ、Ｋ+が０．３ｐｐｍ、Ｃａ2+が０．４ｐｐ
ｍ、Ｆｅ3+は１．９ｐｐｍであり、純度が９７．９％、
また結晶色が茶色と不良であった。Comparative Example 3 The procedure of Example 1 was repeated, except that no activated carbon was added. The yield is 70%, and the ionic component is Na + 1.
9 ppm, K + 0.3 ppm, Ca 2+ 0.4 pp
m, Fe 3+ is 1.9 ppm, purity is 97.9%,
The crystal color was brown and poor.
【００１９】[0019]
【発明の効果】本発明の方法により簡易にＮ−フェニル
グリシンの超高純度品を得ることができ、これは実用上
極めて価値のあるものである。According to the method of the present invention, it is possible to easily obtain an ultra-pure N-phenylglycine product, which is extremely valuable in practical use.
フロントページの続き (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 229/00 C07C 227/00 ＣＡ（ＳＴＮ)Continuation of the front page (58) Field surveyed (Int. Cl. 7 , DB name) C07C 229/00 C07C 227/00 CA (STN)
Claims (5)
結晶する際に、活性炭及びキレート剤を添加することを
特徴とするＮ−フェニルグリシンの精製方法。1. A method for purifying N-phenylglycine, comprising adding activated carbon and a chelating agent when recrystallizing crude N-phenylglycine with water.
Ｎ，Ｎ’，Ｎ’−テトラ酢酸またはその塩である請求項
１記載の方法。2. The chelating agent is ethylenediamine-N,
The method according to claim 1, which is N, N ', N'-tetraacetic acid or a salt thereof.
−エチレンジアミン−Ｎ，Ｎ’，Ｎ’−トリ酢酸または
その塩である請求項１記載の方法。3. The method according to claim 1, wherein the chelating agent is N- (hydroxyethyl).
The method according to claim 1, which is -ethylenediamine-N, N ', N'-triacetic acid or a salt thereof.
Ｎ，Ｎ，Ｎ’，Ｎ”，Ｎ”−ペンタ酢酸またはその塩で
ある請求項１記載の方法。4. The chelating agent is diethylenetriamine-
The method according to claim 1, which is N, N, N ', N ", N" -pentaacetic acid or a salt thereof.
の塩である請求項１記載の方法。5. The method according to claim 1, wherein the chelating agent is nitrilotriacetic acid or a salt thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14712392A JP3169433B2 (en) | 1992-06-08 | 1992-06-08 | Method for purifying N-phenylglycine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14712392A JP3169433B2 (en) | 1992-06-08 | 1992-06-08 | Method for purifying N-phenylglycine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05339217A JPH05339217A (en) | 1993-12-21 |
| JP3169433B2 true JP3169433B2 (en) | 2001-05-28 |
Family
ID=15423066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14712392A Expired - Fee Related JP3169433B2 (en) | 1992-06-08 | 1992-06-08 | Method for purifying N-phenylglycine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3169433B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101941033B (en) * | 2010-08-30 | 2012-05-23 | 张家港市明华机械制造有限公司 | Feeding apparatus |
| US8561449B2 (en) | 2009-06-05 | 2013-10-22 | Wafios Aktiengesellschaft | Bending apparatus for rod-shaped workpieces |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107930183B (en) * | 2017-12-20 | 2020-06-12 | 浙江云涛生物技术股份有限公司 | Phenylglycine strong base mother liquor resin decoloring device and decoloring process |
-
1992
- 1992-06-08 JP JP14712392A patent/JP3169433B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8561449B2 (en) | 2009-06-05 | 2013-10-22 | Wafios Aktiengesellschaft | Bending apparatus for rod-shaped workpieces |
| CN101941033B (en) * | 2010-08-30 | 2012-05-23 | 张家港市明华机械制造有限公司 | Feeding apparatus |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05339217A (en) | 1993-12-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |