JPS63295568A - Separation of isothiazoline compound - Google Patents
Separation of isothiazoline compoundInfo
- Publication number
- JPS63295568A JPS63295568A JP63009947A JP994788A JPS63295568A JP S63295568 A JPS63295568 A JP S63295568A JP 63009947 A JP63009947 A JP 63009947A JP 994788 A JP994788 A JP 994788A JP S63295568 A JPS63295568 A JP S63295568A
- Authority
- JP
- Japan
- Prior art keywords
- cmi
- methyl
- isothiazoline
- compound
- dmp
- 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.)
- Granted
Links
- -1 isothiazoline compound Chemical class 0.000 title abstract description 3
- 238000000926 separation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 claims abstract description 4
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 14
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical class C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 6
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 claims description 2
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 7
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 6
- 239000006227 byproduct Substances 0.000 abstract description 2
- 230000026030 halogenation Effects 0.000 abstract description 2
- 238000005658 halogenation reaction Methods 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 238000011084 recovery Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000498 cooling water Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000013535 sea water Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000195493 Cryptophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- WXTPRAZNOXQAFY-UHFFFAOYSA-N 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C#CC#CC(O)(C=1C=CC=CC=1)C1=CC=CC=C1 WXTPRAZNOXQAFY-UHFFFAOYSA-N 0.000 description 1
- GLQWGVMBEKNKTP-UHFFFAOYSA-N 1,1-bis(2,4-dimethylphenyl)prop-2-yn-1-ol Chemical compound CC1=CC(C)=CC=C1C(O)(C#C)C1=CC=C(C)C=C1C GLQWGVMBEKNKTP-UHFFFAOYSA-N 0.000 description 1
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical compound O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000237536 Mytilus edulis Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- BFNOLLCLWHGGTO-UHFFFAOYSA-N O=C1N=[S+]CC1 Chemical compound O=C1N=[S+]CC1 BFNOLLCLWHGGTO-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 241000251555 Tunicata Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000003619 algicide Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 235000020638 mussel Nutrition 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明はイソチアゾリン系化合物の分離方法に係り、特
に優れた抗菌剤として有用な５−クロロ−２−メチル−
４−イソチアゾリン−３−オンを効率的に分離すること
ができるイソチアゾリン系化合物の分離方法に関する。Detailed Description of the Invention [Industrial Field of Application] The present invention relates to a method for separating isothiazoline compounds, particularly 5-chloro-2-methyl-, which is useful as an excellent antibacterial agent.
The present invention relates to a method for separating isothiazoline compounds that can efficiently separate 4-isothiazolin-3-one.
［従来の技術］
各種工場施設の冷却水系或は紙バルブ抄造系等の水系に
おいては、次のような様々な菌類又は動植物類のスライ
ムが付着し、様々な障害を引き起こしている。[Prior Art] In water systems such as cooling water systems of various factory facilities or paper valve manufacturing systems, slimes of various fungi or animals and plants such as those described below adhere, causing various problems.
冷却水系においては、ズーグレア状細菌、藻類、糸状菌
等のスライムが付着し、熱効率の低下、通水の悪化、金
属材賞等の腐食の誘発等の原因となっている。In the cooling water system, slime such as zooglare bacteria, algae, and filamentous fungi adheres to the cooling water system, causing a decrease in thermal efficiency, poor water flow, and induction of corrosion of metal materials.
紙バルブ抄造系においては、細菌、糸状菌、酵母等のス
ライムが主に抄紙工程で発生し、これはバルブスラリー
中に異物として混入・付着して、製品の品質を低下させ
るばかりでなく、紙切れを発生させ、生産効率を大幅に
低下さｉる等の様々な障害を引き起こす、特に、近年、
紙バルブ抄造系においては、循環水の使用量を高める傾
向にあり、スライムによる問題はより重要なものとなっ
ている。In the paper valve manufacturing system, slime from bacteria, filamentous fungi, yeast, etc. is mainly generated during the paper making process, and this slime gets mixed in and adheres to the valve slurry as foreign matter, not only reducing the quality of the product but also causing paper breakage. In particular, in recent years,
In paper valve manufacturing systems, there is a tendency to increase the amount of circulating water used, and the problem caused by slime is becoming more important.
海水を利用する火力発電所や製鉄所等の諸工場の冷却水
系の取水口や冷却管の内面には、海水性藻類、海水性バ
クテリアやムラサキイガイ、ホヤ等の生物が付着し、こ
れらの機能低下の原因となっている。また付着したこれ
らの生物は、水圧や流速等により剥ぎ取られ、熱交換器
のチューブやストレーナ等の他の部位の目詰りをも引き
起こし、海水の通水を妨げ装置全体の機能を低下させる
。Marine organisms such as seawater algae, seawater bacteria, mussels, and sea squirts adhere to the inside surfaces of the cooling water intakes and cooling pipes of thermal power plants, steel mills, and other factories that use seawater, resulting in a decline in their functionality. It is the cause of In addition, these attached organisms are peeled off by water pressure, flow velocity, etc., causing clogging in other parts of the heat exchanger, such as tubes and strainers, which obstructs the flow of seawater and reduces the functionality of the entire device.
従来、このようなスライムによる障害を防止するために
は、その処理法が比較的簡便なこと、安価であるとから
、抗菌剤（スライムコントロール剤）が一般に使用され
ている。しかして、特に汎用されている抗菌剤としては
１．ヒドラジン（Ｎ２Ｈ４）又はイソチアゾリン系化合
物等の水溶性殺菌剤が挙げられる。これらのうち、特に
下記（１）式で示される５−クロロ−２−メチル−４−
イソチアゾリン−３−オン（以下ｒＣＭ Ｉ Ｊと略称
する。）は抗菌力に優れており、冷却水系用、紙バルブ
用、水泳プール用等各種水系用スライムコントロール剤
、殺菌剤、殺藻剤、殺かび剤として広く使用されている
。Conventionally, in order to prevent such problems caused by slime, antibacterial agents (slime control agents) have generally been used because the treatment method is relatively simple and inexpensive. However, the most widely used antibacterial agents are 1. Examples include water-soluble fungicides such as hydrazine (N2H4) or isothiazoline compounds. Among these, in particular, 5-chloro-2-methyl-4- represented by the following formula (1)
Isothiazolin-3-one (hereinafter abbreviated as rCMIJ) has excellent antibacterial properties and is used as a slime control agent, bactericide, algaecide, and disinfectant for various water systems such as cooling water systems, paper valves, and swimming pools. Widely used as a fungicide.
このＣＭＩは、一般に、
■ β−チオケトアミドを酢酸エステル等の不活性有機
エステル溶剤中でハロゲン化する、■ β置換チオシア
ノアクリルアミド又はチオサルファードアクリルアミド
を酸で処理してイソチアゾロンを得、更にハロゲン化す
る、方法で製造されている。（１１公昭４６−Ｚ１２４
０ｇ欠和）［発明が解決しようとする課題］
しかしながら、上記■及び■の方法のいずれの場合にお
いても、ＣＭＩだけを選択的に得ることはできず、副生
成物として、下記（ＩＩ）式で示される、抗菌力がＣＭ
Ｉよりも１０倍も劣る、２−メチル−４−イソチアゾリ
ン−３−オン（以下、ｒＭＩＪと略称する。）が混入し
たものしか得られない。This CMI generally involves: ■ halogenating a β-thioketamide in an inert organic ester solvent such as an acetate; ■ treating a β-substituted thiocyanoacrylamide or thiosulfated acrylamide with an acid to obtain an isothiazolone; and further halogenation. Manufactured using a method that (11 Kosho 46-Z124
0g deficiency) [Problem to be solved by the invention] However, in both of the above methods ① and ②, it is not possible to selectively obtain only CMI, and as a by-product, the following formula (II) The antibacterial activity shown by CM
Only a product containing 2-methyl-4-isothiazolin-3-one (hereinafter abbreviated as rMIJ), which is 10 times inferior to I, can be obtained.
しかも従来の技術では、反応生成混合物からＣＭＩのみ
を選択的に取り出すことはできず、やむを得ず抗菌力が
劣るＭｌも混合したままの状態で使用しているのが実状
である。しかも、市販品としては、ＣＭＩの安定化剤と
して更に塩化マグネシウムや硝酸マグネシウムが配合さ
れている。Moreover, in the conventional technology, it is not possible to selectively extract only CMI from the reaction product mixture, and the reality is that Ml, which has poor antibacterial activity, is unavoidably used in a mixed state. Furthermore, commercially available products further contain magnesium chloride and magnesium nitrate as stabilizers for CMI.
このため、従来よりＣＭＩ及びＭｌ等を含む混合液から
、ＣＭＩのみを選択的に高収率で分離することができる
分離方法の出現が強く望まれていた。For this reason, there has been a strong desire for a separation method that can selectively separate only CMI in high yield from a mixed solution containing CMI, Ml, and the like.
本発明はこのような従来の実情に鑑みてなされたもので
あり、ＣＭＩ及びＭｌを含む混合液からＣＭＩを効率的
に選択分離する方法を提供することを目的とする。The present invention has been made in view of such conventional circumstances, and an object of the present invention is to provide a method for efficiently selectively separating CMI from a liquid mixture containing CMI and Ml.
［課題を解決するための手段］
本発明のイソチアゾリン系化合物の分離方法は、ＣＭＩ
及びＭｌを含む混合溶液にホスト化合物を加えて、ＣＭ
ＩをＣＭＩを含む包接化合物として分離することを特徴
とする。[Means for Solving the Problems] The method for separating isothiazoline compounds of the present invention uses CMI
A host compound is added to a mixed solution containing CM and Ml.
It is characterized by separating I as an inclusion compound containing CMI.
ホスト化合物としては特に１，１，６．６−テトラフェ
ニル−２，４−ヘキサジイン−１，６−ジオール（以下
ｒＴＰＨＪと略処する。）又は１．１−ジ（２，４−ジ
メチルフェニル）−２−プロピン−１−オール（以下ｒ
ＤＭＰＪと略称する。）を用いるのが好ましい。The host compound is particularly 1,1,6,6-tetraphenyl-2,4-hexadiyn-1,6-diol (hereinafter abbreviated as rTPHJ) or 1,1-di(2,4-dimethylphenyl)- 2-propyn-1-ol (r
It is abbreviated as DMPJ. ) is preferably used.
以下本発明の詳細な説明する。The present invention will be explained in detail below.
本発明において、ホスト化合物としては、ＣＭＩと包接
化合物を形成し得るものであれば良く、特に制限はない
が、好ましいホスト化合物としては、ＴＰＨ又はＤＭＰ
が挙げられる。In the present invention, the host compound is not particularly limited as long as it can form a clathrate compound with CMI, but preferred host compounds include TPH or DMP.
can be mentioned.
ＴＰＨ％ＤＭＰは各々下記（ｍ）及び（ｒＶ）式％式％
本発明においては、これらＴＰＨ又はＤＭＰ等のホスト
化合物をＣＭＩ及びＭＩを含む混合溶液に加える。具体
的には、メタノール、エタノール等の有機溶媒にＴＰＨ
又はＤＭＰを溶解させた溶液と、ＣＭＩ及びＭＩを含む
混合溶液とを混合して反応させる。これにより、ＣＭＩ
を含む包接化合物が白濁物として析出する。この白濁物
は常法により、濾通分離することにより容易に固体とし
て分離回収することができる。TPH%DMP is represented by the formulas (m) and (rV) below, respectively.In the present invention, a host compound such as TPH or DMP is added to a mixed solution containing CMI and MI. Specifically, TPH is added to an organic solvent such as methanol or ethanol.
Alternatively, a solution in which DMP is dissolved and a mixed solution containing CMI and MI are mixed and reacted. This allows CMI
A clathrate compound containing this precipitates out as a white turbidity. This white cloudy substance can be easily separated and recovered as a solid by filtering and separating by a conventional method.
即ち、ＣＭＩはゲスト分子として、選択的にＴＰＨ又は
ＤＭＰ等のホスト分子に包接され、包接化合物として析
出する。このようにして得られる包摂化合物は、製造条
件等により小異はあるものの、一般には、次の如き反応
により、各式の右辺に示される組成を有する包接化合物
として得られる。That is, CMI, as a guest molecule, is selectively included in host molecules such as TPH or DMP, and precipitated as an inclusion compound. The clathrate compounds obtained in this manner are generally obtained as clathrate compounds having the composition shown on the right side of each formula by the following reaction, although there are slight differences depending on the manufacturing conditions and the like.
ＴＰＨ＋２ＣＭＩ−４ＴＰＨ・ （ＣＭＩ）２２ＤＭＰ
＋ＣＭＩ → （ＤＭＰ）２ ・ ＣＭＩ分離された
ＣＭＩを包接する包接化合物からＣＭＩを回収するには
、該包接化合物を水中に浸漬して放置すれば良い、これ
により、ＣＭＩが水中に溶出し、極めて高純度の精製Ｃ
ＭＩが得られる。TPH+2CMI-4TPH・(CMI)22DMP
+CMI → (DMP)2 ・CMI To recover CMI from the clathrate compound that includes the separated CMI, it is sufficient to immerse the clathrate compound in water and leave it.This allows the CMI to elute into the water. , extremely high purity purified C
MI is obtained.
［作用］
ＣＭＩは適当なホスト化合物と接触すると極めて選択的
に包接され、ＣＭＩ−ホスト化合物の包摂化合物を生成
し、このものは反応液中に効率的に析出する。このため
、本発明の方法によれば、従来分離困難とされていたＣ
ＭＩ及びＭＩの混合物から、ＣＭＩのみを容易に分離す
ることができる。しかして、分離されたＣＭＩ包接化合
物からは、水中浸漬等の簡単な手段で、極めて容易にＣ
ＭＩを回収することができる。[Operation] When CMI comes into contact with a suitable host compound, it is very selectively included, producing a CMI-host compound inclusion compound, which is efficiently precipitated in the reaction solution. Therefore, according to the method of the present invention, C
Only CMI can be easily separated from a mixture of MI and MI. Therefore, it is extremely easy to remove CMI from the separated CMI clathrate compound by simple means such as immersion in water.
MI can be recovered.
特に、ＴＰＨ又はＤＭＰをホスト化合物として用いるこ
とにより、効率的な分離が行なえる。In particular, efficient separation can be achieved by using TPH or DMP as a host compound.
［実施例コ
以下に本発明を実施例を挙げて更に具体的に説明するが
、本発明はその要旨を超えない限り以下の実施例に限定
されるものではない。[Example] The present invention will be described in more detail with reference to Examples below, but the present invention is not limited to the following Examples unless the gist thereof is exceeded.
実施例Ｉ
ＴＰＨ５００ｍｇ （１，２１Ｘ１０−３モル）をメタ
ノール１０ｍＩＬに溶解したＴＰＨ溶液に、ＣＭＩ、Ｍ
ｌ混合物であるＫＡＴＨＯＮ８８８（ロームアンドハー
ス社製品）を４．２６ｇ（ＣＭＩとして３２６ｆｎｇ、
２．４２Ｘ１０−３モル）を添加して攪拌したところ、
白濁物が析出した。これを室温で３時間静置した後、濾
紙で濾通して析出物と溶液とを分離した。Example I CMI, M
4.26 g of KATHON 888 (Rohm and Haas product) (326 fng as CMI,
2.42 x 10-3 mol) was added and stirred,
A white cloudy substance was precipitated. After this was allowed to stand at room temperature for 3 hours, it was filtered through a filter paper to separate the precipitate and the solution.
析出物のＮＭＲ分析の結果、析出物はモル比でＴＰＨ：
ＣＭＩ”１：２、重量比で５８．１：４１．９であるか
らＴＰＨ・（ＣＭＩ）２の包接化合物であることが確認
された。なお、ＭＩ、塩化マグネシウム、硝酸マグネシ
ウムは含まれていないことが元素分析により確認された
。As a result of NMR analysis of the precipitate, the precipitate had a molar ratio of TPH:
CMI"1:2, and the weight ratio was 58.1:41.9, so it was confirmed that it was a clathrate compound of TPH/(CMI)2. Note that MI, magnesium chloride, and magnesium nitrate were not included. It was confirmed by elemental analysis that there was no such thing.
実施例２
ＤＭＰ５００ｍｇ （１，８９ｘｌＯ″′３モル）をメ
タノール１０ｍＪｌに溶解したＤＭＰ溶液に、前記にＡ
ＴＨＯＮ８８６を３．３２８ （ＣＭＩとして２８３ｍ
ｇ、１．８９Ｘ１０−３モル）を添加して攪拌したとこ
ろ、白濁物が析出した。この析出物を上記方法と同様に
して分離し、分析を行なったところ、析出物はモル比で
ＤＭＰ ： ＣＭＩ−２：１、重量比で７７．９：２２
．１であるから（ＤＭＰ）２・ＣＭＩの包接化合物であ
ることが確認された。なお、ＭＩ、塩化マグネシウム、
硝酸マグネシウムは含まれていないことが元素分析によ
り確認された。Example 2 A DMP solution prepared by dissolving 500 mg of DMP (1,89
THON886 3.328 (283m as CMI
g, 1.89×10 −3 mol) was added and stirred, and a white cloudy substance was precipitated. This precipitate was separated and analyzed in the same manner as above, and the molar ratio of the precipitate was DMP:CMI-2:1, and the weight ratio was 77.9:22.
．． 1, it was confirmed that it was an inclusion compound of (DMP)2.CMI. In addition, MI, magnesium chloride,
Elemental analysis confirmed that it did not contain magnesium nitrate.
実施例３．４
実施例１．２で得られたＴＰＨ・ （ＣＭＩ）２（実施
例３）及び（ＤＭＰ）２ ・ＣＭＩ（実施例４）を、Ｃ
ＭＩ換算で０．１ｇとなるように、０．８μメンブレン
フイルタ一袋に入れ、これを純水１ｆｌ中に浸漬し、ス
ターラー攪拌しながらＣＭＩの溶出を行なった。ＣＭＩ
濃度の経時変化を調べ、結果を第１表に示した。Example 3.4 TPH・ (CMI) 2 (Example 3) and (DMP) 2 ・CMI (Example 4) obtained in Example 1.2 were
An amount of 0.1 g in terms of MI was placed in a bag of 0.8μ membrane filter, which was immersed in 1 fl of pure water, and CMI was eluted with stirring using a stirrer. CMI
Changes in concentration over time were investigated, and the results are shown in Table 1.
第１表 ＣＭＩ濃度の経時変化
（単位ｐｐｍ）
第１表から明らかなように、水中浸漬により包接化合物
からＣＭＩは徐々に溶出するため、高純度ＣＭＩが容易
に回収できる。Table 1 Change in CMI concentration over time (unit: ppm) As is clear from Table 1, CMI is gradually eluted from the clathrate compound by immersion in water, so that high purity CMI can be easily recovered.
［発明の効果］
以上詳述した通り、本発明のイソチアゾリン系化合物の
分離方法によれば、ＣＭＩ及びＭｌの混合溶液から、Ｃ
ＭＩのみを選択的、かつ効率的に分離することができる
。特に、ＴＰＨ又はＤＭＰをホスト化合物として用いる
ことにより効率的な分離が行なえる。[Effects of the Invention] As detailed above, according to the method for separating isothiazoline compounds of the present invention, CMI and Ml can be separated from a mixed solution of CMI and Ml.
Only MI can be selectively and efficiently separated. In particular, efficient separation can be achieved by using TPH or DMP as a host compound.
本発明の方法はＣＭＩの分離、精製方法として、工業上
極めて有用である。The method of the present invention is industrially extremely useful as a method for separating and purifying CMI.
Claims (2)
３−オン及び２−メチル−４−イソチアゾリン−３−オ
ンを含む混合溶液にホスト化合物を加えて、５−クロロ
−２−メチル−４−イソチアゾリン−３−オンをこれを
含む包接化合物として分離することを特徴とするイソチ
アゾリン系化合物の分離方法。(1) 5-chloro-2-methyl-4-isothiazoline-
A host compound is added to a mixed solution containing 3-one and 2-methyl-4-isothiazolin-3-one, and 5-chloro-2-methyl-4-isothiazolin-3-one is separated as an inclusion compound containing it. A method for separating isothiazoline compounds.
ル−２，４−ヘキサジイン−１，６−ジオール又は１，
１−ジ（２，４−ジメチルフェニル）−２−プロピン−
１−オールであることを特徴とする特許請求の範囲第１
項に記載の方法。(2) The host compound is 1,1,6,6,-tetraphenyl-2,4-hexadiyn-1,6-diol or 1,
1-di(2,4-dimethylphenyl)-2-propyne-
Claim 1 characterized in that it is 1-all.
The method described in section.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63009947A JPS63295568A (en) | 1988-01-20 | 1988-01-20 | Separation of isothiazoline compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63009947A JPS63295568A (en) | 1988-01-20 | 1988-01-20 | Separation of isothiazoline compound |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59173771A Division JPS6153201A (en) | 1984-08-21 | 1984-08-21 | Gradually releasable antibiotic |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63295568A true JPS63295568A (en) | 1988-12-01 |
| JPH0349907B2 JPH0349907B2 (en) | 1991-07-31 |
Family
ID=11734180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63009947A Granted JPS63295568A (en) | 1988-01-20 | 1988-01-20 | Separation of isothiazoline compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63295568A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4996220A (en) * | 1988-01-25 | 1991-02-26 | Kurita Water Industries Ltd. | Method of producing a clathrate compound |
-
1988
- 1988-01-20 JP JP63009947A patent/JPS63295568A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4996220A (en) * | 1988-01-25 | 1991-02-26 | Kurita Water Industries Ltd. | Method of producing a clathrate compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0349907B2 (en) | 1991-07-31 |
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