JPH01261368A - Method for purifying pyridine - Google Patents
Method for purifying pyridineInfo
- Publication number
- JPH01261368A JPH01261368A JP9101988A JP9101988A JPH01261368A JP H01261368 A JPH01261368 A JP H01261368A JP 9101988 A JP9101988 A JP 9101988A JP 9101988 A JP9101988 A JP 9101988A JP H01261368 A JPH01261368 A JP H01261368A
- Authority
- JP
- Japan
- Prior art keywords
- pyridine
- reducing agent
- purity
- contact
- sodium borohydride
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 74
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 9
- 238000004821 distillation Methods 0.000 abstract description 7
- 239000000843 powder Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 239000007864 aqueous solution Substances 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 235000011121 sodium hydroxide Nutrition 0.000 abstract description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 229910052708 sodium Inorganic materials 0.000 abstract description 2
- 239000011734 sodium Substances 0.000 abstract description 2
- XLKNMWIXNFVJRR-UHFFFAOYSA-N boron potassium Chemical compound [B].[K] XLKNMWIXNFVJRR-UHFFFAOYSA-N 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 description 18
- 229910000033 sodium borohydride Inorganic materials 0.000 description 18
- 239000012535 impurity Substances 0.000 description 12
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 9
- 241000122205 Chamaeleonidae Species 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 235000014102 seafood Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野コ
本発明はピリジンの精製方法、さらに詳しくは純度９９
％程度のピリジンを還元剤に接触させることによりさら
に高品質の製品を得ることを特徴とするピリジンの精製
方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for purifying pyridine, more specifically, a method for purifying pyridine to a purity of 99%.
% of pyridine is brought into contact with a reducing agent to obtain a product of even higher quality.
ピリジンは、産業界において医薬や農薬物質の原料とし
て、また各種有機合成中間体として、巾広い用途を持っ
ている。Pyridine has a wide range of uses in industry, as a raw material for pharmaceuticals and agricultural chemicals, and as an intermediate for various organic synthesis.
ピリジンにはアミン類、アルコール類、アルデヒド類等
の種々の横道不明の不純物が含まれており、これら不純
物の存在は製品であるピリジンの品質を低下させるだけ
でなく、さらに医薬品など誘導体を合成するための原料
として用いられた場合、得られる誘導体の品質に悪影響
を与える。Pyridine contains various unidentified impurities such as amines, alcohols, and aldehydes, and the presence of these impurities not only reduces the quality of the product pyridine, but also makes it difficult to synthesize derivatives such as pharmaceuticals. When used as a raw material for the production of derivatives, the quality of the resulting derivatives is adversely affected.
特に、これ等の不純物のうち、目的とするピリジンと沸
点が近似している不１４’ｔｋは、単に精留操作のみで
は除去し難い。In particular, among these impurities, impurity 14'tk, which has a boiling point similar to that of the target pyridine, is difficult to remove simply by rectification.
一方、これら不純物のない高品質、高純度のピリジンが
近年医薬の原料として用いられるようになったため関係
業界で高純度ピリジンの供給が望まれている。On the other hand, in recent years, high quality, high purity pyridine free from these impurities has come to be used as a raw material for pharmaceuticals, and therefore the supply of high purity pyridine is desired in related industries.
［従来技術］
ピリジン、ピコリン、ルチジンなどのピリジン塩基類は
２例えば、アンモニアとアルデヒド、オレフィン等との
反応による合成法によって製造されている他、コークス
炉ガスまたは、タール油からの回収法によっても製造さ
れている。[Prior Art] Pyridine bases such as pyridine, picoline, and lutidine are produced by a synthetic method involving the reaction of ammonia with aldehydes, olefins, etc., and also by recovery methods from coke oven gas or tar oil. Manufactured.
これら合成法あるいは１回収法のいずれの方法であって
も製造されたピリジンには微量の不純物が存在し、その
品質を低下させている。Regardless of the synthesis method or single recovery method, the pyridine produced contains trace amounts of impurities, degrading its quality.
これら微量不純物は明確に定量または定性分析されてい
る訳ではないが、上記アミン類、アルコ−ル類、アルデ
ヒド類等のような化合物であると考えられている。Although these trace impurities have not been clearly quantitatively or qualitatively analyzed, they are thought to be compounds such as the above-mentioned amines, alcohols, aldehydes, and the like.
例えば、アルデヒド類などが混入している場合にはこれ
が縮合して生じた縮合物などもその一例である。For example, when aldehydes are mixed, condensates formed by condensation of these are also examples.
これらの微量不純物を除去し、高品質のピリジンを製造
するためにこれまで種々の物理的処理法か考案されてい
る。Various physical treatment methods have been devised to remove these trace impurities and produce high quality pyridine.
たとえば、特公昭４２−２４４２１号公報には。For example, in Japanese Patent Publication No. 42-24421.
１放量の不純物を含んだピリジン塩基類に水を添加して
精留を行なう方法が開示されているが、多量の水を加え
２共沸処理を行なうため単にピリジン塩基類を蒸留する
以上に多量の加熱蒸気を必要とし、有利な工業的製造法
とはいい難い。A method has been disclosed in which water is added to pyridine bases containing a small amount of impurities for rectification, but since a large amount of water is added and azeotropic treatment is performed, a larger amount than simply distilling pyridine bases is required. It is difficult to say that it is an advantageous industrial manufacturing method because it requires heating steam of
また、これらの不純物を除去するための化学的処理法と
して、米国特許２４５４０１９号公報に粗ピリジンとＮ
ａＯＨ水溶液とを加え、加熱還流した後、脱水蒸留する
方法が開示されているが。In addition, as a chemical treatment method for removing these impurities, US Pat. No. 2,454,019 discloses crude pyridine and N
However, a method is disclosed in which an aOH aqueous solution is added, heated to reflux, and then dehydrated and distilled.
前記と同じ理由により、工業的に不利である。For the same reason as above, it is industrially disadvantageous.
［発明が解決しようとする課題〕
以上のような状況下高純度ピリジンを得るための簡単で
しかも、エネルギーを多量に使用しない高純度ピリジン
の製造方法の確立が望まれていた。[Problems to be Solved by the Invention] Under the above circumstances, it has been desired to establish a method for producing high-purity pyridine that is simple and does not use a large amount of energy.
本発明者は、鋭意検討した結果１本発明を完成させた。The inventor of the present invention has completed the present invention as a result of intensive studies.
［課題を解決するための手段］
すなわち、本発明は
「高純度のピリジンに還元剤を接触させることを特徴と
するピリジンの精製方法」
である。[Means for Solving the Problems] That is, the present invention is "a method for purifying pyridine characterized by bringing a reducing agent into contact with highly purified pyridine."
本発明は、煩雑な手段を用いずに、ピリジンの精製を行
なわんとするものである。The present invention aims to purify pyridine without using complicated means.
本発明のポイントは例えば蒸留等の操作によって得た純
度９９％程度の、従来は通常の用途においてはそのまま
製品として用いられていたいわゆる高純度ピリジンに水
素化ホウ素金属などの還元剤を接触させることにより、
その製品ピリジンの品質試験の一つであるカメレオン変
色テストの赤紫色状態の保持時間を延ばし、医薬関係の
業界で望まれているさらに高品質、高純度のピリジンを
製造することにある。 用い得る還元剤としては水素化
ホウ素アルカリ金属またはアルカリ土類金属、具体的に
は水素化ホウ素ナトリウムＮａＢＨ４の曲に水素化ホウ
素アルミニウムＡｊＢＨ４などがある。The key point of the present invention is to bring a reducing agent such as metal borohydride into contact with so-called high-purity pyridine, which has a purity of about 99% obtained through operations such as distillation, and which has conventionally been used as a product in normal applications. According to
The goal is to extend the retention time of the reddish-purple state in the chameleon discoloration test, which is one of the quality tests for the pyridine product, and to produce pyridine of even higher quality and purity, which is desired by the pharmaceutical industry. Examples of reducing agents that can be used include alkali metal borohydride or alkaline earth metal borohydride, specifically sodium borohydride NaBH4 and aluminum borohydride AjBH4.
本発明の方法によれば、煩雑な操作を行うことなく、従
来品に比べて最高級の精製品を得ることが出来るので工
業的に極めて価値かある。According to the method of the present invention, it is possible to obtain a purified product of the highest quality compared to conventional products without performing complicated operations, so it is extremely valuable industrially.
カメレオン変色テストとはサンプル１０ｍ１に１／１０
０Ｎの過マンガン酸カリ水溶液１ ｍｌを加え、よく混
合し、２０°Ｃに保持したときの赤紫色状態が退色する
までの保持時間を測定することをいう。What is the chameleon discoloration test? 1/10 sample per 10m1
1 ml of 0N potassium permanganate aqueous solution is added, mixed well, and held at 20°C. The retention time until the reddish-purple state fades is measured.
この退色するまでの保持時間か短い程不純物が多いこと
を示す。The shorter the holding time until the color fades, the more impurities there are.
本発明において処理の対象となる高純度ピリジンは通常
の精製手段１例えば、蒸留等によって一旦精製され、９
９．０％程度の純度を有する。いわゆる、製品として一
般には使用されているグレードのものである。The high-purity pyridine to be treated in the present invention is once purified by ordinary purification means 1, such as distillation, and then
It has a purity of about 9.0%. This is a so-called grade that is generally used as a product.
もちろん上記のものよりグレードの低いものに対しても
処理効果はあるが、水素化ホウ素ナトリウムなどの還元
剤の使用量が著しく多くなることとさらに池の処理法を
組み合わせて処理度合いを高める必要があるからである
。Of course, the treatment is effective for substances of a lower grade than those mentioned above, but the amount of reducing agent such as sodium borohydride used is significantly increased, and it is necessary to combine the pond treatment method to increase the degree of treatment. Because there is.
本発明に使用される還元剤の代表的なものは水素化ホウ
素金属、具体的には水素化ホウ素ナトリウム、同カリウ
ムなどであるが、それらは粉末。Typical reducing agents used in the present invention are metal borohydride, specifically sodium borohydride, potassium borohydride, etc., which are powders.
錠剤または顆粒状か、または、苛性ソーダ水溶ン夜でも
よく１また担体等に担持されていてもコーティングされ
ていてもよく、その形状については詩に制限されない。It may be in the form of tablets, granules, or aqueous sodium hydroxide solution, or may be supported on a carrier or coated, and its shape is not limited to the above.
具体的な処理方法としては還元剤の錠剤を充填した塔ま
たは適当な容器に処理の対象になるピリジンを通液する
か、還元剤の粉末１錠剤または顆粒状のものをピリジン
に添加することによりＲｔ＝、ｌｉ的に接触させて行な
う。The specific treatment method is to pass the pyridine to be treated through a tower or suitable container filled with reducing agent tablets, or to add a powdered tablet or granules of the reducing agent to the pyridine. This is carried out by contacting Rt=, li.
水素化ホウ素ナトリウムなどの還元剤の形態が粉末また
は顆粒状の場合には一定時間接触させた後、濾過または
蒸溜により分離する。When the reducing agent, such as sodium borohydride, is in the form of powder or granules, it is separated by filtration or distillation after being in contact with it for a certain period of time.
水素化ホウ素ナトリウムなどの還元剤の形態が苛性ソー
ダ水溶液の場合には分液操作または蒸溜により分離され
る。When the reducing agent such as sodium borohydride is in the form of an aqueous solution of caustic soda, it is separated by liquid separation or distillation.
被処理ピリジンの量に対して使用される水素化ホウ素ナ
トリウムなどの還元剤の量はカメレオン変色テストの保
持時間の長短、すなわち、不純物の含有量によって異な
るので、−該にはいえない。The amount of reducing agent such as sodium borohydride used relative to the amount of pyridine to be treated varies depending on the retention time of the chameleon discoloration test, that is, the content of impurities, and therefore cannot be said to be a general rule.
−船釣には以下のような使用量を基準とするのが良い。- For boat fishing, it is best to use the following amount as a standard.
一例としてアルデヒドの濃度がたとえば、１０ＤｐＩ〜
１００１）ｌ）ＩＩＩの場合には還元剤の使用は５０〜
５００ ｐｐｌ′１程度にするのが一つの目安である。As an example, the concentration of aldehyde is, for example, 10DpI~
1001) l) In the case of III, the use of a reducing agent is 50~
One guideline is to keep it at around 500 ppl'1.
還元剤の添加量が５０１）ｌ）ｌより少ないとカメレオ
ン物質の除去効果が低く、逆に５００ ｐｔ１１１以上
添加しても無駄になるからである。This is because if the amount of reducing agent added is less than 501) liters, the effect of removing chameleon substances will be low, and conversely, even if 500 pt111 or more is added, it will be wasteful.
還元剤の錠剤を充填した塔などを通過させて処理する場
合は、上記の使用濃度は現実的には対応せず、かなり過
剰のものを使用することとなる。When processing by passing through a tower filled with reducing agent tablets, the above-mentioned concentration is not practical, and a considerably excessive amount is used.
水素化ホウ素ナトリウム、水素化ホウ素アルミニウムが
好適な理由は常温、常圧で還元可能であり、かつ、アル
デヒドなどを選択的に還元するからである。Sodium borohydride and aluminum borohydride are preferable because they can be reduced at normal temperature and pressure, and selectively reduce aldehydes and the like.
水素化ホウ素ナトリウムなどの還元剤による処理速度は
また。接触時間にも依存する。Processing speed with reducing agents such as sodium borohydride is also significant. It also depends on the contact time.
本発明の方法において、還元剤として水素（ヒホウ素ナ
トリウムＮ ａ Ｂ Ｈ４を用いた場合でまた。In the method of the present invention, hydrogen (sodium boroboronate N a B H4) is also used as the reducing agent.
カメレオン物質がアルデヒドの場合には以下のような反
応式により反応が進行する。When the chameleon substance is an aldehyde, the reaction proceeds according to the following reaction formula.
４ ＲＣ＋ Ｎ ａ Ｂ Ｈ４＋ ２ Ｈ２０一４ＲＨ
２−ＯＨ＋ＮａＢＯ３
（Ｒは水素またはアルキル基である）
上記のような反応式により反応が進行するとすれば、水
素化ホウ素ナトリウムＮ ａ Ｂ Ｈ４の還元能力は以
下の通りである。4 RC+ N a B H4+ 2 H20-4RH
2-OH+NaBO3 (R is hydrogen or an alkyl group) If the reaction proceeds according to the above reaction formula, the reducing ability of sodium borohydride NaBH4 is as follows.
すなわち、１モルの水素化ホウ素ナトリウムＮａＢＨ４
は４モルのアルデヒドを還元することになる。That is, 1 mole of sodium borohydride NaBH4
will reduce 4 moles of aldehyde.
水素化ホウ素ナトリウムＮ ａ Ｂ Ｈ４の分子量は３
７．８４であるので、１ｇの水素化ホウ素ナトリウムＮ
ａ Ｂ Ｈ４は２ｊの水素ガスの還元能力、すなわち
、アルデヒド４．６ｇを相当するアルコールに還元する
。The molecular weight of sodium borohydride N a B H4 is 3
7.84, so 1g of sodium borohydride N
a B H4 has the hydrogen gas reducing ability of 2j, ie, reduces 4.6 g of aldehyde to the corresponding alcohol.
以下実施例及び比較例を挙げて本発明の方法を具体的に
説明する。The method of the present invention will be specifically explained below with reference to Examples and Comparative Examples.
「実施例−１」
純度９９．０％のピリジンを１０１００Ｏ，回分式蒸留
塔（目皿１０段）を付備した１」の缶に仕込み、水素化
ホウ素ナトリウム粉末０．Ｉｇｒを添加した。"Example-1" Pyridine with a purity of 99.0% was charged into a 10100O can with a batch distillation column (10 perforations), and sodium borohydride powder with 0.0% purity was charged. Igr was added.
蒸留塔は７６０ｍ＋ｎＨｇの常圧に保たれ、還流比５に
て精留を行なった。The distillation column was maintained at normal pressure of 760 m+nHg, and rectification was performed at a reflux ratio of 5.
初めに、低沸魚介を含んだ留分として１５０ｇｒとり、
さらに製品留分として８０４ｇｒが得られた。First, take 150g as a distillate containing low-boiling seafood,
Furthermore, 804 gr was obtained as a product fraction.
この製品のカメレオン変色テストの保持時間は４０００
秒であった。The retention time of this product in the chameleon color change test is 4000
It was seconds.
「比較例−１」
水素化ホウ素ナトリウムを添加しないで、「実施例−１
」と同様に蒸留した時の留出ピリジンのカメレオン変色
テストの保持時間は０秒であった。"Comparative Example-1""Example-1" without adding sodium borohydride
The retention time of distilled pyridine in the chameleon color change test was 0 seconds when distilled in the same manner as ``.
「比較例−２」
水素化ホウ素ナトリウムを添加せず水を５０ｇｒ添加し
て、「実施例−１」と同じく蒸留をした時の留出ピリジ
ンのカメレオン変色テストの保持時間は０秒であった。"Comparative Example-2" When 50g of water was added without adding sodium borohydride and distillation was carried out in the same manner as in "Example-1", the retention time of the chameleon color change test of distilled pyridine was 0 seconds. .
Claims (1)
ピリジンの精製方法。A method for purifying pyridine, which comprises contacting high-purity pyridine with a reducing agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63091019A JP2565738B2 (en) | 1988-04-13 | 1988-04-13 | Pyridine purification method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63091019A JP2565738B2 (en) | 1988-04-13 | 1988-04-13 | Pyridine purification method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01261368A true JPH01261368A (en) | 1989-10-18 |
| JP2565738B2 JP2565738B2 (en) | 1996-12-18 |
Family
ID=14014848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63091019A Expired - Lifetime JP2565738B2 (en) | 1988-04-13 | 1988-04-13 | Pyridine purification method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2565738B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010134193A1 (en) * | 2009-05-22 | 2010-11-25 | エア・ウォーター株式会社 | Method for producing pyridine compound and pyridine compound |
| CN102382043A (en) * | 2011-09-23 | 2012-03-21 | 安徽工业大学 | Purification method for yellowed pyridine |
| CN103951609A (en) * | 2009-05-22 | 2014-07-30 | 爱沃特株式会社 | Preparation method of pyridine compound |
| WO2014119292A1 (en) * | 2013-01-31 | 2014-08-07 | 広栄化学工業株式会社 | Method for purifying pyridine compound |
| CN113698341A (en) * | 2021-11-01 | 2021-11-26 | 潍坊新绿化工有限公司 | Pyridine purification method |
-
1988
- 1988-04-13 JP JP63091019A patent/JP2565738B2/en not_active Expired - Lifetime
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010134193A1 (en) * | 2009-05-22 | 2010-11-25 | エア・ウォーター株式会社 | Method for producing pyridine compound and pyridine compound |
| EP2433930A1 (en) * | 2009-05-22 | 2012-03-28 | Air Water Inc. | Method for producing pyridine compound and pyridine compound |
| CN102448935A (en) * | 2009-05-22 | 2012-05-09 | 爱沃特株式会社 | Method for producing pyridine compound and pyridine compound |
| JP5142345B2 (en) * | 2009-05-22 | 2013-02-13 | エア・ウォーター株式会社 | Method for producing pyridine compound |
| EP2433930A4 (en) * | 2009-05-22 | 2013-08-21 | Air Water Inc | Method for producing pyridine compound and pyridine compound |
| US8742128B2 (en) | 2009-05-22 | 2014-06-03 | Air Water Inc. | Process for producing pyridine compound, and pyridine compound |
| CN103951609A (en) * | 2009-05-22 | 2014-07-30 | 爱沃特株式会社 | Preparation method of pyridine compound |
| CN102382043A (en) * | 2011-09-23 | 2012-03-21 | 安徽工业大学 | Purification method for yellowed pyridine |
| WO2014119292A1 (en) * | 2013-01-31 | 2014-08-07 | 広栄化学工業株式会社 | Method for purifying pyridine compound |
| CN113698341A (en) * | 2021-11-01 | 2021-11-26 | 潍坊新绿化工有限公司 | Pyridine purification method |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2565738B2 (en) | 1996-12-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW301649B (en) | ||
| JPH01261368A (en) | Method for purifying pyridine | |
| CA1056383A (en) | Process for producing nicotinic amide | |
| CN107778141B (en) | Purification method of 1, 4-butanediol | |
| JPS584750A (en) | Preparation of high purity aniline | |
| JP2002212153A (en) | Method for amino group introduction and method for amino acid synthesis | |
| Russell et al. | Facile reduction of unsaturated compounds containing nitrogen | |
| JPH053455B2 (en) | ||
| JPS61251662A (en) | Purification of pyridine | |
| SU472497A3 (en) | The method of obtaining anthracene or its derivatives | |
| JP2001199960A (en) | Method for purifying pyridine | |
| JPS6172727A (en) | Production of styrene | |
| JP2007534614A (en) | Method for producing ethanolamine with improved color | |
| JPS58157751A (en) | Recovery of monomethylhydrazine | |
| JPH03120240A (en) | Method for purifying dialkyl carbonate | |
| US3164535A (en) | Recovery of high purity nitrosodimethylamine by distillation and phase separation both with caustic | |
| SU649702A1 (en) | Method of obtaining methylisobutylketone | |
| US2796421A (en) | Process of making alkyl pyridines | |
| JP3685511B2 (en) | Purification method of aqueous oxyacetic acid solution | |
| JPS63112562A (en) | Production of 5,6,7,8-tetrahydroquinolines | |
| JPH0495090A (en) | Purification of trioxane | |
| US3441569A (en) | Method for preparing polycyclic heterocyclic compounds | |
| JPH02121946A (en) | Continuous production of succinic acid | |
| US2806070A (en) | Process of producing polychloro benzenes from hexachloro cyclohexanes | |
| RU1824393C (en) | Process for producing n-aminobenzoyl-cyanoacetoethyl ester |