JPH02255658A - Method for concentrating and separating 2-methylquinoline - Google Patents
Method for concentrating and separating 2-methylquinolineInfo
- Publication number
- JPH02255658A JPH02255658A JP7385589A JP7385589A JPH02255658A JP H02255658 A JPH02255658 A JP H02255658A JP 7385589 A JP7385589 A JP 7385589A JP 7385589 A JP7385589 A JP 7385589A JP H02255658 A JPH02255658 A JP H02255658A
- Authority
- JP
- Japan
- Prior art keywords
- methylquinoline
- cyclodextrins
- cyclodextrin
- alpha
- clathrate
- 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
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 title claims abstract description 101
- 238000000034 method Methods 0.000 title claims abstract description 13
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 13
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 13
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 13
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- 229920000858 Cyclodextrin Polymers 0.000 claims description 4
- 229940097362 cyclodextrins Drugs 0.000 claims description 2
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical compound C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 abstract description 16
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 abstract description 16
- 229940043377 alpha-cyclodextrin Drugs 0.000 abstract description 16
- 238000000926 separation method Methods 0.000 abstract description 6
- 239000012535 impurity Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 150000002898 organic sulfur compounds Chemical class 0.000 abstract description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000011280 coal tar Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007385 chemical modification Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- -1 cyclic oligosaccharides Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- YLAUVUQZNJMLEC-UHFFFAOYSA-N 2-methylquinoline;quinoline Chemical compound N1=CC=CC2=CC=CC=C21.C1=CC=CC2=NC(C)=CC=C21 YLAUVUQZNJMLEC-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- FYGDTMLNYKFZSV-DZOUCCHMSA-N alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-D-Glcp Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-DZOUCCHMSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Landscapes
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、２−メチルキノリンを含有する炭化水素油中
の２−メチルキノリンを濃縮分離する方法に関する。詳
しくは２−メチルキノリンを含有する炭化水素油とα−
シクロデキストリン類を接触させ、２−メチルキノリン
含有炭化水素油中２−メチルキノリンとα−シクロデキ
ストリン類の包接化合物を形成させ、これを回収して２
−メチルキノリンを濃縮分離する方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for concentrating and separating 2-methylquinoline in hydrocarbon oil containing 2-methylquinoline. For details, hydrocarbon oil containing 2-methylquinoline and α-
Cyclodextrins are brought into contact to form an inclusion compound of 2-methylquinoline and α-cyclodextrin in a hydrocarbon oil containing 2-methylquinoline, and this is recovered.
- A method for concentrating and separating methylquinoline.
［従来の技術］
２−メチルキノリンは、絹、羊毛等の黄色の染料として
用いられるキノフタロンの原料として重要な化合物であ
る。[Prior Art] 2-Methylquinoline is an important compound as a raw material for quinophthalone, which is used as a yellow dye for silk, wool, etc.
しかし、これらの用途に供するためには、純度の高いこ
とが重要で、特に異性体の８−メチルキノリンや、有機
硫黄化合物等の混在は、極力排除しなければならない。However, in order to use it for these purposes, it is important to have high purity, and in particular, the presence of isomers such as 8-methylquinoline and organic sulfur compounds must be avoided as much as possible.
２−メチルキノリンは、コールタール系粗キノリン（２
３５〜２４０℃留分）中に少量存在し、キノリンを分離
した釜残油から回収されている。2-Methylquinoline is coal tar-based crude quinoline (2-methylquinoline).
It is present in small amounts in the 35-240°C fraction) and is recovered from the residual oil from which quinoline was separated.
しかし、キノリンを分離した釜残油中には、２−メチル
キノリンのほか、異性体である８−メチルキノリンやキ
ノリン、インキノリン、その他の不純物が多量含有され
ており、これを蒸留しても、得られる２−メチルキノリ
ンの純度は、８５％程度が限度である。これは、沸点の
極めて近接した８−メチルキノリンとの分離が不可能な
ためである。However, in addition to 2-methylquinoline, the residual oil from the kettle after separating quinoline contains large amounts of isomers such as 8-methylquinoline, quinoline, inquinoline, and other impurities, and even if this is distilled, The purity of the obtained 2-methylquinoline is limited to about 85%. This is because it is impossible to separate it from 8-methylquinoline, which has very close boiling points.
［発明が解決しようとする課題］
本発明は、従来分離困難と考えられていた２−メチルキ
ノリンを、公知の蒸留や晶析等の濃縮分離手段を用いる
ことなく濃縮分離する、新規な２−メチルキノリンの濃
縮分離方法を提供するものである。[Problems to be Solved by the Invention] The present invention is a novel method for concentrating and separating 2-methylquinoline, which was conventionally thought to be difficult to separate, without using known concentration separation means such as distillation or crystallization. The present invention provides a method for concentrating and separating methylquinoline.
［課題を解決するための手段］
本発明では、２−メチルキノリンを含有する炭化水素油
からの２−メチルキノリンの分離剤としてα−シクロデ
キストリン類を使用する。[Means for Solving the Problems] In the present invention, α-cyclodextrins are used as a separation agent for 2-methylquinoline from a hydrocarbon oil containing 2-methylquinoline.
α−シクロデキストリン類は、６個のグルコビラノース
基がα−１，４結合した環状オリゴ糖で、王冠状の構造
を有しており、その空洞に様々な有機化合物を取り込ん
で包接化合物を形成することができる。α-Cyclodextrins are cyclic oligosaccharides in which six glucobylanose groups are α-1,4-linked, and have a crown-like structure. Various organic compounds can be incorporated into the cavity to form clathrate compounds. can be formed.
その包接化合物形成能を分離に応用する試みは、従来、
Ｏ−＋ ｍ−＋ ｐ一体のようなベンゼン二置換異性体
や光学異性体の分離を中心に行われてきた。Attempts to apply its clathrate-forming ability to separation have been
It has mainly been carried out to separate benzene disubstituted isomers and optical isomers such as O-+ m-+ p monomers.
一方、コールタール留分や石油留分は、多種類の成分か
らなる複雑な混合物であり、これらの留分中の特定成分
の分離にシクロデキストリン類を適用する試みは、分析
目的の面では若干例があるが、特定成分の分離濃縮に用
いられた例は見当たらない。On the other hand, coal tar fractions and petroleum fractions are complex mixtures consisting of many types of components, and attempts to apply cyclodextrins to separate specific components in these fractions have been somewhat difficult for analytical purposes. Although there are examples, I have not found any examples of it being used to separate and concentrate specific components.
本発明者らは、２−メチルキノリン含有炭化水素油中の
２−メチルキノリンの濃縮分離について鋭意試験研究の
結果、α−シクロデキストリン類と２−メチルキノリン
含有炭化水素油中の２−メチルキノリンとの包接錯体の
生成定数が極めて大きく、特に８−メチルキノリンがほ
とんど包接錯体を形成しないのに対し、２−メチルキノ
リンは極めて包接錯体を形成し易く、選択的に包接され
ることを見い出し、この性質を利用して２−メチルキノ
リンの新規な濃縮分離法を完成した。The present inventors have conducted extensive research on the concentration and separation of 2-methylquinoline in hydrocarbon oil containing 2-methylquinoline, and found that α-cyclodextrins and 2-methylquinoline in hydrocarbon oil containing 2-methylquinoline The formation constant of inclusion complexes with We discovered this and completed a new method for concentrating and separating 2-methylquinoline by utilizing this property.
すなわち本発明は、２−メチルキノリンを含有する炭化
水素油とα−シクロデキストリン類を接触させて２−メ
チルキノリンとα−シクロデキストリン類の包接化合物
を形成させ、該包接化合物を回収することを特徴とする
２−メチルキノリンの濃縮分離法である。That is, the present invention brings a hydrocarbon oil containing 2-methylquinoline into contact with α-cyclodextrins to form an inclusion compound of 2-methylquinoline and α-cyclodextrins, and recovers the clathrate compound. This is a method for concentrating and separating 2-methylquinoline.
本発明において使用するα−シクロデキストリン類とし
ては、α−シクロデキストリンあるいはα−シクロデキ
ストリンを化学修飾、例えばα−シクロデキストリンの
少なくとも一つの水酸基の水素を、グルコース、マルト
ース、マルトオリゴ糖、ヒドロキシプロピル基、メチル
基、スルホン基、カルボキシアルキル基のうちの、少な
くとも一つで置換した置換型α−シクロデキストリンを
挙げることができる。このようにα−シクロデキストリ
ンを化学修飾することにより水に対する溶解度が向上す
るので、包接化および回収の際の水溶液濃度を高めるこ
とができ、濾過、回収の装置がコンパクトになり、精製
操作が合理化されるのみならず、製品および包接化剤の
ロスを少なくすることができる。 本発明においては、
α−シクロデキストリン類を水に溶解あるいは懸濁させ
、これを２−メチルキノリンを含有する炭化水素油と混
合し、激しく撹拌する。この場合のα−シクロデキスト
リン類の濃度は、例えば、α−シクロデキストリンの場
合であれば、５〜２０％、好ましくは１０〜１５％が適
当である。 また、α−シクロデキストリン類水溶液を
２−メチルキノリンを含有する炭化水素油との混合割合
は、２−メチルキノリン１モルに対し、α−シクロデキ
ストリン類１〜５モル、好ましくは１．５〜２．５モル
となるようにする。 撹拌はできるだけ激しく行なうこ
とが望ましく、数１０分から数時間行なう、なお、温度
は３０〜４５”Ｃ程度が望ましい。The α-cyclodextrins used in the present invention include chemical modification of α-cyclodextrin or α-cyclodextrin, for example, hydrogenation of at least one hydroxyl group of α-cyclodextrin to glucose, maltose, maltooligosaccharide, or hydroxypropyl group. , a methyl group, a sulfone group, and a carboxyalkyl group. Chemical modification of α-cyclodextrin improves its solubility in water, making it possible to increase the concentration of the aqueous solution during inclusion and recovery, making filtration and recovery equipment more compact, and simplifying purification operations. Not only is the process streamlined, but the loss of the product and clathrating agent can be reduced. In the present invention,
α-Cyclodextrins are dissolved or suspended in water, mixed with a hydrocarbon oil containing 2-methylquinoline, and stirred vigorously. In this case, the appropriate concentration of α-cyclodextrin is, for example, 5 to 20%, preferably 10 to 15% in the case of α-cyclodextrin. The mixing ratio of the aqueous solution of α-cyclodextrins with the hydrocarbon oil containing 2-methylquinoline is 1 to 5 mol, preferably 1.5 to 5 mol, of the α-cyclodextrin per 1 mol of 2-methylquinoline. The amount should be 2.5 mol. It is desirable to stir as vigorously as possible, ranging from several tens of minutes to several hours, and preferably at a temperature of about 30 to 45''C.
０合液は、α−シクロデキストリン類包接化合物の生成
により白濁する。撹拌終了後、反応生成物を分離する０
例えば、２，５００ｒｐｍで５〜１０分間遠心分離した
のち、これを孔径０．４μｍのメンブランフィルタ−で
濾過、水洗し、アセトン等の有機溶媒を用いて洗浄した
のち、乾燥することにより白色固体の包接化合物が得ら
れる。The mixture becomes cloudy due to the formation of α-cyclodextrin clathrate compounds. After stirring, separate the reaction product.
For example, after centrifuging at 2,500 rpm for 5 to 10 minutes, it is filtered through a membrane filter with a pore size of 0.4 μm, washed with water, washed with an organic solvent such as acetone, and dried to form a white solid. A clathrate is obtained.
この白色固体の包接化合物中には、２−メチルキノリン
以外の有機化合物も含有されているので、これらを−旦
６０〜７０℃以上熱水中で解離させたのち、再び包接化
を繰り返すことによつて、２−メチルキノリンの純度を
高めることができる。This white solid clathrate compound also contains organic compounds other than 2-methylquinoline, so these are first dissociated in hot water at 60 to 70°C or higher, and then clathration is repeated again. In particular, the purity of 2-methylquinoline can be increased.
なお、以上の全工程において、α−シクロデキストリン
類分子自体は、分解することがないので、回収し循環使
用することができる。In all of the above steps, the α-cyclodextrin molecules themselves do not decompose, so they can be recovered and recycled.
α−シクロデキストリン類と２−メチルキノリン等の包
接化合物からの２−メチルキノリン等の分離には、種々
の方法がある。例えば、包接化合物を熱水に溶解させ、
包接錯体を解離させたのち、解離した２−メチルキノリ
ン等をヘキサン、ヘプタン等の適当な有機溶媒を用いて
抽出する方法、あるいは、包接化合物を水に懸濁させ、
ジエチルエーテル等の適当な有機溶媒を添加して振とう
し、２−メチルキノリン等を有機層に抽出する方法等が
ある。There are various methods for separating 2-methylquinoline and the like from clathrate compounds such as α-cyclodextrins and 2-methylquinoline. For example, by dissolving the clathrate in hot water,
After the inclusion complex is dissociated, the dissociated 2-methylquinoline etc. are extracted using a suitable organic solvent such as hexane or heptane, or the clathrate is suspended in water,
There is a method of adding a suitable organic solvent such as diethyl ether and shaking to extract 2-methylquinoline and the like into the organic layer.
［実施例］
以下、実施例によって本発明をさらに具体的に説明する
。[Examples] Hereinafter, the present invention will be explained in more detail with reference to Examples.
本実施例における主な成分の分析は、ガスクロマトグラ
フ法を用いた。表中の数字は、各成分の面積百分率であ
る。Gas chromatography was used to analyze the main components in this example. The numbers in the table are the area percentages of each component.
夾施伝工
容量５０ｍβのガラスフラスコにα−シクロデキストリ
ンの１０％水溶液２５ｒｒｌと第１表に示す組成の２−
メチルキノリンと８−メチルキノリンとの混合原料０．
５ｇを仕込み、３０℃で激しく１時間撹拌した。In a glass flask with a construction capacity of 50 mβ, 25 rrl of a 10% aqueous solution of α-cyclodextrin and 2-
Mixed raw material of methylquinoline and 8-methylquinoline 0.
5 g was charged and stirred vigorously at 30°C for 1 hour.
撹拌終了後反応生成物を孔径０．４μｍのメンブランフ
ィルタ−を用いて濾過し、回収した包接化合物を水で洗
浄したのち、アセトンで洗浄し乾燥した。この包接化合
物を熱水に懸濁させて包接化合物を解離し、ついでジエ
チルエーテルで抽出し、２−メチルキノリン等を分離回
収し、α−シクロデキストリンと分離した。After the stirring was completed, the reaction product was filtered using a membrane filter with a pore size of 0.4 μm, and the recovered clathrate compound was washed with water, followed by acetone and dried. This clathrate compound was suspended in hot water to dissociate the clathrate compound, and then extracted with diethyl ether to separate and recover 2-methylquinoline and the like, which were then separated from α-cyclodextrin.
原料および包接化物中の組成を第１表に示す。Table 1 shows the composition of the raw materials and clathrates.
以下余白
第 １ 表
第１表に示すとおり、８−メチルキノリンはほとんど包
接化合物を形成しないが、２−メチルキノリンは、α−
シクロデキストリンと極めて特異的に包接化合物を形成
し、２−メチルキノリンが純度９９％以上と、高濃度に
濃縮された包接化物が得られる。As shown in Table 1, 8-methylquinoline hardly forms clathrate compounds, but 2-methylquinoline forms α-
It forms an inclusion compound very specifically with cyclodextrin, and a highly concentrated inclusion compound with a purity of 99% or more of 2-methylquinoline can be obtained.
夾施伝ｌ
コールタール系粗キノリン留分を蒸留してキノリンを回
収した釜残油を蒸留し、第２表に示す組成の粗２−メチ
ルキノリンを回収した。そして容量５０ｒｒｌのガラス
フラスコにα−シクロデキストリンの１０％水溶液２５
ｍ２と第２表に示す組成の粗２−メチルキノリン０．５
ｇを仕込み、３０℃で１時間激しく撹拌した。1. Coal tar-based crude quinoline fraction was distilled to recover quinoline. The residual oil was distilled to recover crude 2-methylquinoline having the composition shown in Table 2. Then, in a glass flask with a capacity of 50 rrl, 25% of a 10% aqueous solution of α-cyclodextrin was added.
m2 and 0.5 crude 2-methylquinoline with the composition shown in Table 2.
g and stirred vigorously at 30°C for 1 hour.
撹拌終了後反応生成物を孔径０．４μｍのメンブランフ
ィルタ−を用いて濾過し、回収した包接化合物を水で洗
浄したのち、アセトンで洗浄し乾燥した。この包接化合
物を熱水に懸濁させて包接化合物を解離し、ついでジエ
チルエーテルで抽出し、２−メチルキノリンを分離回収
してα−シクロデキストリンと分離した。After the stirring was completed, the reaction product was filtered using a membrane filter with a pore size of 0.4 μm, and the recovered clathrate compound was washed with water, followed by acetone and dried. This clathrate was suspended in hot water to dissociate the clathrate, and then extracted with diethyl ether to separate and collect 2-methylquinoline and separate it from α-cyclodextrin.
粗２−メチルキノリンおよび包接化物中の組成ケ第２表
に示す。The compositions of crude 2-methylquinoline and clathrates are shown in Table 2.
第 ２ 表
第２表に示すとおり、８−メチルキノリンはほとんど包
接化合物を形成しないが、２−メチルキノリンは、α−
シクロデキストリンと極めて特異的に包接化合物を形成
し、２−メチルキノリンが高濃度に濃縮された包接化合
物が得られる。Table 2 As shown in Table 2, 8-methylquinoline hardly forms clathrate compounds, but 2-methylquinoline forms α-
A clathrate is formed very specifically with cyclodextrin, and a clathrate in which 2-methylquinoline is highly concentrated is obtained.
［発明の効果］
以上述べたとおり本発明方法によれば、２−メチルキノ
リン含有炭化水素油から８−メチルキノリンや有機硫黄
化合物等の不純物を容易に分離除去し、２−メチルキノ
リンを濃縮分離することができる。[Effects of the Invention] As described above, according to the method of the present invention, impurities such as 8-methylquinoline and organic sulfur compounds can be easily separated and removed from 2-methylquinoline-containing hydrocarbon oil, and 2-methylquinoline can be concentrated and separated. can do.
Claims (1)
シクロデキストリン類水溶液を接触させて２−メチルキ
ノリンとα−シクロデキストリン類の包接化合物を形成
させ、該包接化合物を回収することを特徴とする２−メ
チルキノリンの濃縮分離法。(1) Hydrocarbon oil containing 2-methylquinoline and α-
1. A method for concentrating and separating 2-methylquinoline, which comprises bringing an aqueous solution of cyclodextrins into contact with each other to form a clathrate compound of 2-methylquinoline and α-cyclodextrins, and recovering the clathrate compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7385589A JP2634233B2 (en) | 1989-03-28 | 1989-03-28 | Concentration and separation of 2-methylquinoline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7385589A JP2634233B2 (en) | 1989-03-28 | 1989-03-28 | Concentration and separation of 2-methylquinoline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02255658A true JPH02255658A (en) | 1990-10-16 |
| JP2634233B2 JP2634233B2 (en) | 1997-07-23 |
Family
ID=13530188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7385589A Expired - Lifetime JP2634233B2 (en) | 1989-03-28 | 1989-03-28 | Concentration and separation of 2-methylquinoline |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2634233B2 (en) |
-
1989
- 1989-03-28 JP JP7385589A patent/JP2634233B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2634233B2 (en) | 1997-07-23 |
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