JPH0439448B2 - - Google Patents
Info
- Publication number
- JPH0439448B2 JPH0439448B2 JP3125384A JP3125384A JPH0439448B2 JP H0439448 B2 JPH0439448 B2 JP H0439448B2 JP 3125384 A JP3125384 A JP 3125384A JP 3125384 A JP3125384 A JP 3125384A JP H0439448 B2 JPH0439448 B2 JP H0439448B2
- Authority
- JP
- Japan
- Prior art keywords
- inclusion complex
- dinaphthol
- organic compounds
- picoline
- mixture
- 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
Links
- 150000002894 organic compounds Chemical class 0.000 claims description 21
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 18
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 229940043279 diisopropylamine Drugs 0.000 claims description 5
- 150000003462 sulfoxides Chemical class 0.000 claims description 5
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000004292 cyclic ethers Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- JXTGICXCHWMCPM-UHFFFAOYSA-N (methylsulfinyl)benzene Chemical compound CS(=O)C1=CC=CC=C1 JXTGICXCHWMCPM-UHFFFAOYSA-N 0.000 claims description 2
- DVVGIUUJYPYENY-UHFFFAOYSA-N 1-methylpyridin-2-one Chemical compound CN1C=CC=CC1=O DVVGIUUJYPYENY-UHFFFAOYSA-N 0.000 claims description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims 2
- 239000000470 constituent Substances 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000013078 crystal Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 238000000746 purification Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- QGLBZNZGBLRJGS-UHFFFAOYSA-N Dihydro-3-methyl-2(3H)-furanone Chemical compound CC1CCOC1=O QGLBZNZGBLRJGS-UHFFFAOYSA-N 0.000 description 1
- -1 amino acid salts Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
【発明の詳細な説明】
本発明は包接錯体形成剤および有機化合物の分
離法、特にホスト化合物としてβ−ジナフトール
から成る包接錯体形成剤およびそれを用いて包接
錯体を形成せしめることによる有機化合物の分離
法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an inclusion complex forming agent and a method for separating organic compounds, particularly an inclusion complex forming agent consisting of β-dinaphthol as a host compound and an organic compound formed by forming an inclusion complex using the same. Concerning methods for separating compounds.
従来、有機化合物の分離精製は、一般にその沸
点や溶解度などの物理的性質を利用した蒸留や再
結晶などが採用されているが、これらの従来法で
は大量のエネルギーが必要であつたり、回収率が
悪かつたりして、分離精製のコストが高くつく場
合が多い。 Traditionally, organic compounds have been separated and purified by methods such as distillation and recrystallization that take advantage of their physical properties such as boiling point and solubility, but these conventional methods require large amounts of energy and have low recovery rates. In many cases, the cost of separation and purification is high due to poor performance.
本発明者らは有機化合物の化学的性質を利用し
た分離精製法を鋭意検討した結果、β−ジナフト
ールが種々の有機化合物を包接錯体化することが
でき、この事実を応用すれば工業的有利に有機化
合物の分離精製を達成出来ることを見出し、この
知見に基づいて本発明を完成するに至つた。有機
化合物の分離精製にβ−ジナフトールを使用した
例としては、クラムの研究が知られているが〔J.
Am Chem Soc.4555（1978）〕、これは光学活性ク
ラウンエーテルにβ−ジナフトールを組み込んだ
ものをホスト化合物として使用し、包接錯体化に
よりアミンやアミノ酸の塩の光学分割を達成する
ものであつて、β−ジナフトールを単独で使用し
て有機化合物と包接錯体を形成せしめた例はこれ
まで報告されていない。すなわち、β−ジナフト
ールそれ自体が種々の有機化合物と包接錯体を形
成し得る事実は本発明者らが初めて見出したもの
である。 The present inventors have intensively studied separation and purification methods that utilize the chemical properties of organic compounds, and have found that β-dinaphthol can form inclusion complexes with various organic compounds.If this fact is applied, it will be industrially advantageous. The inventors have discovered that separation and purification of organic compounds can be achieved using the method, and have completed the present invention based on this knowledge. A known example of the use of β-dinaphthol for the separation and purification of organic compounds is the work of Kram [J.
Am Chem Soc. 4555 (1978)], which uses an optically active crown ether in which β-dinaphthol is incorporated as a host compound, and achieves optical resolution of amine and amino acid salts through inclusion complexation. However, no example has been reported to date in which β-dinaphthol is used alone to form an inclusion complex with an organic compound. That is, the fact that β-dinaphthol itself can form inclusion complexes with various organic compounds was discovered for the first time by the present inventors.
本発明の要旨は、β−ジナフトールから成る包
接錯体形成剤および２種以上の有機化合物の混合
物とβ−ジナフトールを接触させて該混合物中の
１種の有機化合物とβ−ジナフトールの間で包接
錯体を形成せしめ、次いでこの包接錯体を分離す
ることを特徴とする有機化合物の分離法に存す
る。 The gist of the present invention is to contact β-dinaphthol with an inclusion complex forming agent consisting of β-dinaphthol and a mixture of two or more organic compounds to form an encapsulation complex between one organic compound in the mixture and β-dinaphthol. The present invention relates to a method for separating organic compounds, which is characterized by forming an inclusion complex and then separating the inclusion complex.
本発明において、ホスト化合物たるβ−ジナフ
トールと包接錯体を回転するゲスト化合物として
は、アミン類、環状エーテル類、エステル類、ケ
トン類、スルホキシド類、アミド類等が挙げられ
る。更に具体的には、アミン類としてモノメチル
アミン、ジメチルアミン、モノエチルアミン、ジ
イソプロピルアミン、sec−ブチルアミン、ピリ
ジン、α−ピコリン、γ−ピコリン、２，６−ル
チジン、２−ピリドン、１−メチル−２−ピリド
ン、キノリン、２−メチルキノリン、２−ピロリ
ドン、１−メチル−２−ピロリドンなど、環状エ
ーテルとしてテトラヒドロフラン、１，４−ジオ
キサンなど、エステル類としてγ−メチルブチロ
ラクトン、トリメチルリン酸エステルなど、ケト
ン類としてアセトフエノン、シクロペンタノンな
ど、スルホキシド類としてジメチルスルホキシ
ド、フエニルメチルスルホキシドなど、アミド類
としてジメチルホルムアミドなどを挙げることが
出来る。本発明方法を実施するには、たとえばゲ
スト化合物を含有する混合物にβ−ジナフトール
を添加し、必要に応じこれを加熱して包接錯体化
を完全に行わしめ、その後必要に応じて冷却し、
生じた結晶を分離、採取すればよい。得られる結
晶性包接錯体の組成は、通常、β−ジナフトー
ル：ゲスト化合物（モル比）0.5〜１：１である。 In the present invention, examples of the guest compound that rotates the inclusion complex with β-dinaphthol, which is the host compound, include amines, cyclic ethers, esters, ketones, sulfoxides, amides, and the like. More specifically, the amines include monomethylamine, dimethylamine, monoethylamine, diisopropylamine, sec-butylamine, pyridine, α-picoline, γ-picoline, 2,6-lutidine, 2-pyridone, 1-methyl-2 - Pyridone, quinoline, 2-methylquinoline, 2-pyrrolidone, 1-methyl-2-pyrrolidone, etc.; cyclic ethers such as tetrahydrofuran, 1,4-dioxane; esters such as γ-methylbutyrolactone, trimethyl phosphate, etc.; ketones; Examples of the sulfoxides include dimethyl sulfoxide and phenylmethyl sulfoxide, and amides include dimethylformamide. To carry out the method of the present invention, for example, β-dinaphthol is added to a mixture containing a guest compound, heated if necessary to completely form the inclusion complex, and then cooled if necessary.
The resulting crystals can be separated and collected. The composition of the crystalline inclusion complex obtained is usually β-dinaphthol:guest compound (molar ratio) of 0.5 to 1:1.
本発明方法を更に詳しく説明すれば、β−ジナ
フトールによつてゲスト化合物を包接錯体化させ
る場合、β−ジナフトールはゲスト化合物を含有
する混合物中のゲスト化合物に対し0.5〜１倍モ
ルの割合で用いるのが好ましい。包接錯体化に際
し反応温度は０〜50℃の範囲内で行うのが好まし
い。包接錯体化は概ね３〜24時間の反応時間で完
結する。 To explain the method of the present invention in more detail, when a guest compound is formed into an inclusion complex with β-dinaphthol, β-dinaphthol is used at a ratio of 0.5 to 1 times the mole of the guest compound in the mixture containing the guest compound. It is preferable to use The reaction temperature during inclusion complex formation is preferably within the range of 0 to 50°C. Inclusion complexation is generally completed in a reaction time of 3 to 24 hours.
ゲスト化合物含有混合物中にはβ−ジナフトー
ルとゲスト化合物の包接錯体化を阻害したり、β
−ジナフトールに対し分離しようとするゲスト化
合物よりも容易に包接錯体を形成するものが含ま
れていてはならない。又、ゲスト化合物含有混合
物中の他の成分としては、形成された包接錯体を
溶解しないものが好ましい。 In the guest compound-containing mixture, β-dinaphthol and the guest compound may be inhibited from forming an inclusion complex.
- It must not contain anything that forms an inclusion complex with dinaphthol more easily than the guest compound to be separated. Further, other components in the guest compound-containing mixture are preferably those that do not dissolve the formed inclusion complex.
かくして得られた包接錯体の分離は過等の固
液分離により達成される。分離された包接錯体は
必要に応じて再結晶により精製する。 Separation of the inclusion complex thus obtained is achieved by extensive solid-liquid separation. The separated inclusion complex is purified by recrystallization if necessary.
得られた包接錯体からゲスト化合物を分離回収
するには、この包接錯体を50〜200℃の範囲内で
加熱し、必要に応じて減圧し、ゲストを蒸発させ
回収する。 In order to separate and recover the guest compound from the obtained inclusion complex, the inclusion complex is heated within a range of 50 to 200°C, and if necessary, the pressure is reduced to evaporate and recover the guest.
また、当然のことながら、ゲスト化合物と非ゲ
スト化合物との混合物から、本発明の包接錯体形
成剤によりゲスト化合物を包接錯体とすることに
より、非ゲスト化合物を単離することもできる。 Naturally, the non-guest compound can also be isolated from a mixture of the guest compound and the non-guest compound by forming the guest compound into an inclusion complex using the inclusion complex forming agent of the present invention.
本発明方法に従えば、従来、沸点が接近してい
るため蒸留による分離が不可能としれてきた例え
ばβ−ジナフトール（b.p.144℃）とγ−ピコリ
ン（b.c.145℃）との混合物からγ−ピコリンの
分離が可能となり、高純度のγ−ピコリンが得ら
れる。同様に、種々化合物が低コスト・省エネル
ギーで分離精製される。 According to the method of the present invention, for example, γ-picoline can be separated from a mixture of β-dinaphthol (bp 144°C) and γ-picoline (bc 145°C), which has traditionally been impossible to separate by distillation due to their close boiling points. Separation becomes possible and highly pure γ-picoline can be obtained. Similarly, various compounds can be separated and purified at low cost and with energy savings.
以下、本発明の実施例を挙げて詳細に説明する
が、言うまでもなく、本発明はこれらに限定され
るものではない。 EXAMPLES The present invention will be described in detail below with reference to Examples, but it goes without saying that the present invention is not limited thereto.
実施例 １
β−ジナフトール4.0ｇ、β−ピコリン2.6ｇ及
びγ−ピコリン2.6ｇをメタノール５mlに溶解し、
５℃で12時間放置すると、無色プリズム状結晶が
析出する。この結晶を別し、メタノールで再結
晶すると、2.4ｇの無色プリズム状結晶が得られ
る。得られた結晶を30mmHgの減圧下、100℃に加
熱すると、γ−ピコリン0.8ｇが留出する。留出
したγ−ピコリンの純度は98.9％であつた。Example 1 4.0 g of β-dinaphthol, 2.6 g of β-picoline and 2.6 g of γ-picoline were dissolved in 5 ml of methanol,
When left at 5°C for 12 hours, colorless prismatic crystals precipitate. The crystals are separated and recrystallized with methanol to yield 2.4 g of colorless prismatic crystals. When the obtained crystals are heated to 100° C. under a reduced pressure of 30 mmHg, 0.8 g of γ-picoline is distilled out. The purity of the distilled γ-picoline was 98.9%.
実施例 ２
β−ジナフトール4.0ｇ、１，４−ジオキサン
10％水溶液20ｇ及びメタノール20mlを混合溶解
し、５℃で12時間撹拌すると、白色結晶が析出す
る。この結晶を別し、メタノール40mlで再結晶
すると、白色結晶4.5ｇが得られる。得られた結
晶を100mmHgの減圧下、100℃に加熱すると、１，
４−ジオキサン1.4ｇが留出する。留出した１，
４−ジオキサンの純度は99.6％であつた。Example 2 β-dinaphthol 4.0g, 1,4-dioxane
When 20 g of a 10% aqueous solution and 20 ml of methanol are mixed and dissolved and stirred at 5°C for 12 hours, white crystals are precipitated. Separate the crystals and recrystallize with 40 ml of methanol to obtain 4.5 g of white crystals. When the obtained crystals are heated to 100℃ under a reduced pressure of 100mmHg, 1,
1.4 g of 4-dioxane is distilled off. Distilled 1,
The purity of 4-dioxane was 99.6%.
実施例 ３
β−ジナフトール4.0ｇ、γ−メチルブチロラ
クトン10％水溶液20ｇ及びメタノール20mlを混合
溶解し、５℃で12時間撹拌すると、白色結晶が析
出する。この結晶を別し、メタノール40mlで再
結晶すると、白色結晶4.7ｇが得られる。得られ
た結晶を３mmHgの減圧下、100℃に加熱するとγ
−メチルブチロラクトン1.8ｇが留出する。留出
したγ−メチルブチロラクトンの純度は99.4％で
あつた。Example 3 4.0 g of β-dinaphthol, 20 g of a 10% aqueous solution of γ-methylbutyrolactone, and 20 ml of methanol were mixed and dissolved and stirred at 5° C. for 12 hours to precipitate white crystals. Separate the crystals and recrystallize with 40 ml of methanol to obtain 4.7 g of white crystals. When the obtained crystal is heated to 100℃ under a reduced pressure of 3 mmHg, γ
-1.8 g of methylbutyrolactone are distilled off. The purity of the distilled γ-methylbutyrolactone was 99.4%.
実施例 ４
β−ジナフトール4.0ｇ及びアセトフエノン2.5
ｇを水−メタノール（１：１）40mlに溶解し、５
℃で12時間撹拌すると、白色結晶が析出する。こ
の結晶を別し、メタノール40mlで再結晶する
と、白色結晶5.3ｇが得られる。得られた結晶を
３mmHgの減圧下、100℃に加熱するとアセトフエ
ノン2.1ｇが留出する。留出したアセトフエノン
の純度は99.4％であつた。Example 4 β-dinaphthol 4.0g and acetophenone 2.5g
Dissolve g in 40 ml of water-methanol (1:1) and add 5
After stirring at °C for 12 hours, white crystals precipitate out. Separate the crystals and recrystallize with 40 ml of methanol to obtain 5.3 g of white crystals. When the obtained crystals are heated to 100° C. under a reduced pressure of 3 mmHg, 2.1 g of acetophenone is distilled out. The purity of the distilled acetophenone was 99.4%.
実施例 ５
β−ジナフトール4.0ｇ、ジイソプロピルアミ
ン10％水溶液20ｇ及びメタノール20mlを混合溶解
し、５℃で12時間撹拌すると、白色結晶が析出す
る。この結晶を別し、メタノール40mlで再結晶
すると、白色結晶4.8ｇが得られる。得られた結
晶を300mmHgの減圧下、100℃に加熱するとジイ
ソプロピルアミンが1.6ｇが留出する。留出した
ジイソプロピルアミンの純度は99.6％であつた。Example 5 4.0 g of β-dinaphthol, 20 g of a 10% diisopropylamine aqueous solution and 20 ml of methanol were mixed and dissolved and stirred at 5° C. for 12 hours to precipitate white crystals. Separate the crystals and recrystallize with 40 ml of methanol to obtain 4.8 g of white crystals. When the obtained crystals are heated to 100° C. under a reduced pressure of 300 mmHg, 1.6 g of diisopropylamine is distilled out. The purity of the distilled diisopropylamine was 99.6%.
Claims (1)
種を分離するために使用される特許請求の範囲第
１項記載の包接錯体形成剤。 ３ 分離されるべき特定の有機化合物がアミン
類、環状エーテル類、エステル類、ケトン類、ス
ルホキシド類およびアミド類から選択されたもの
である特許請求の範囲第２項記載の包接錯体形成
剤。 ４ ２種以上の有機化合物の混合物とβ−ジナフ
トールを接触させて該混合物中の１種の有機化合
物とβ−ジナフトールの間で包接錯体を形成せし
め、次いでこの包接錯体を分離することを特徴と
する有機化合物の分離法。 ５ β−ジナフトールと包接錯体を形成する有機
化合物がアミン類、環状エーテル類、エステル
類、ケトン類、スルホキシド類及びアミド類から
選択されたものである特許請求の範囲第４項記載
の分離法。 ６ β−ジナフトールと包接錯体を形成する有機
化合物がモノメチルアミン、ジメチルアミン、モ
ノエチルアミン、ジイソプロピルアミン、sec−
ブチルアミン、ピリジン、α−ピコリン、γ−ピ
コリン、２，６−ルチジン、２−ピリドン、１−
メチル−２−ピリドン、キノリン、２−メチルキ
ノリン、２−ピロリドン、１−メチル−２−ピロ
リドン、テトラヒドロフラン、１，４−ジオキサ
ン、γ−メチルブチロラクトン、トリメチルリン
酸エステル、アセトフエノン、シクロペンタノ
ン、ジメチルスルホキシド、フエニルメチルスル
ホキシド及びメチルホルムアミドから選択された
ものである特許請求の範囲第４項記載の分離法。 ７ 有機化合物の混合物がγ−ピコリンとβ−ピ
コリンを含有する特許請求の範囲第４項記載の分
離法。 ８ 分離された包接錯体を加熱することにより該
包接錯体の構成成分である有機化合物を蒸発、回
収する特許請求の範囲第４項記載の分離法。[Claims] 1. An inclusion complex forming agent comprising β-dinaphthol. 2 A specific one from a mixture of two or more organic compounds
An inclusion complex forming agent according to claim 1, which is used for separating species. 3. The inclusion complex forming agent according to claim 2, wherein the specific organic compound to be separated is selected from amines, cyclic ethers, esters, ketones, sulfoxides and amides. 4 Contacting a mixture of two or more organic compounds with β-dinaphthol to form an inclusion complex between one organic compound in the mixture and β-dinaphthol, and then separating this inclusion complex. Featured methods for separating organic compounds. 5. The separation method according to claim 4, wherein the organic compound forming an inclusion complex with β-dinaphthol is selected from amines, cyclic ethers, esters, ketones, sulfoxides, and amides. . 6 Organic compounds that form inclusion complexes with β-dinaphthol include monomethylamine, dimethylamine, monoethylamine, diisopropylamine, sec-
Butylamine, pyridine, α-picoline, γ-picoline, 2,6-lutidine, 2-pyridone, 1-
Methyl-2-pyridone, quinoline, 2-methylquinoline, 2-pyrrolidone, 1-methyl-2-pyrrolidone, tetrahydrofuran, 1,4-dioxane, γ-methylbutyrolactone, trimethyl phosphate, acetophenone, cyclopentanone, dimethyl 5. The separation method according to claim 4, wherein the separation method is selected from sulfoxide, phenylmethyl sulfoxide and methylformamide. 7. The separation method according to claim 4, wherein the mixture of organic compounds contains γ-picoline and β-picoline. 8. The separation method according to claim 4, wherein the separated inclusion complex is heated to evaporate and recover organic compounds that are constituents of the inclusion complex.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3125384A JPS60174740A (en) | 1984-02-20 | 1984-02-20 | Method for separating organic compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3125384A JPS60174740A (en) | 1984-02-20 | 1984-02-20 | Method for separating organic compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60174740A JPS60174740A (en) | 1985-09-09 |
| JPH0439448B2 true JPH0439448B2 (en) | 1992-06-29 |
Family
ID=12326191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3125384A Granted JPS60174740A (en) | 1984-02-20 | 1984-02-20 | Method for separating organic compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60174740A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4666720B2 (en) * | 2000-06-14 | 2011-04-06 | スガイ化学工業株式会社 | Method for separating and purifying nitrogen-containing aromatic ring compounds |
| EP1342706B1 (en) * | 2000-12-11 | 2013-04-24 | Nippon Soda Co., Ltd. | Method for producing molecular compound |
| JP5367201B2 (en) * | 2001-04-18 | 2013-12-11 | 日本曹達株式会社 | Method for producing molecular compound |
-
1984
- 1984-02-20 JP JP3125384A patent/JPS60174740A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60174740A (en) | 1985-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |