JPH03200769A - Preparation of pyridine chloride - Google Patents
Preparation of pyridine chlorideInfo
- Publication number
- JPH03200769A JPH03200769A JP34467989A JP34467989A JPH03200769A JP H03200769 A JPH03200769 A JP H03200769A JP 34467989 A JP34467989 A JP 34467989A JP 34467989 A JP34467989 A JP 34467989A JP H03200769 A JPH03200769 A JP H03200769A
- Authority
- JP
- Japan
- Prior art keywords
- hydrazinopyridine
- pyridine
- pyridine chloride
- solvent
- hydrogen peroxide
- 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
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 title claims abstract description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 18
- NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical compound NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 230000001590 oxidative effect Effects 0.000 claims abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 15
- 238000000034 method Methods 0.000 abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 11
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000005708 Sodium hypochlorite Substances 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- GIGYTKNSVMLPBE-UHFFFAOYSA-N (3,6-dichloropyridin-2-yl)hydrazine Chemical compound NNC1=NC(Cl)=CC=C1Cl GIGYTKNSVMLPBE-UHFFFAOYSA-N 0.000 description 2
- OCWBGKZFOYMCCN-UHFFFAOYSA-N 3,5-dichloropyridin-2-amine Chemical compound NC1=NC=C(Cl)C=C1Cl OCWBGKZFOYMCCN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- ZHHZCBPODAZZOL-UHFFFAOYSA-N (3,5-dichloropyridin-2-yl)hydrazine Chemical compound NNC1=NC=C(Cl)C=C1Cl ZHHZCBPODAZZOL-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GCTFDMFLLBCLPF-UHFFFAOYSA-N 2,5-dichloropyridine Chemical compound ClC1=CC=C(Cl)N=C1 GCTFDMFLLBCLPF-UHFFFAOYSA-N 0.000 description 1
- FNRMMDCDHWCQTH-UHFFFAOYSA-N 2-chloropyridine;3-chloropyridine;4-chloropyridine Chemical compound ClC1=CC=NC=C1.ClC1=CC=CN=C1.ClC1=CC=CC=N1 FNRMMDCDHWCQTH-UHFFFAOYSA-N 0.000 description 1
- WPGHPGAUFIJVJF-UHFFFAOYSA-N 3,5-dichloropyridine Chemical compound ClC1=CN=CC(Cl)=C1 WPGHPGAUFIJVJF-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は農・医薬中間体として有用なピリジン塩素化物
を製造する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 producing pyridine chloride useful as an agricultural or pharmaceutical intermediate.
これまで、ピリジン塩素化物を得る方法としては、特開
昭６１−２４９９６５号公報に示されるピリジンもしく
はピリジン塩酸塩の液相塩素化や特開昭５８−２０６５
６４号公報に示されるピリジン塩素化物の気相塩素化な
どがある。Up to now, methods for obtaining chlorinated pyridine include liquid phase chlorination of pyridine or pyridine hydrochloride as shown in JP-A No. 61-249965,
Examples include gas phase chlorination of pyridine chlorides as shown in Japanese Patent No. 64.
特に、２．３．５− ）リクロロピリジンの製造法とし
ては種々の方法がある０例えば、２．３．５．６−チト
ラクロロピリジンを亜鉛により還元する方法（ＵＳＰ
４２５９４９５号、同４２５８１９４号、同４１１１９
３８号）や、２−アミノ−３，５−ジクロロピリジンを
出発物質とする方法（Ｂｒｉｔ ＰＡ １２１５３８７
号）がある、他の方法として、２．３．５− トリクロ
ロ−６−ヒドラジノピリジン及び２．３．５−トリクロ
ロ−４−ヒドラジノピリジンを溶媒中で次亜塩素酸ソー
ダにより酸化する方法がある（ＵＳＰ４１２７５７５号
）。この方法の出発物質であるヒドラジノピリジンはク
ロロピリジンと抱水ヒドラジンとの反応により容易に得
られる（Ｊ、 Ｃｈｅａ＋。In particular, there are various methods for producing 2.3.5-)lichloropyridine. For example, the method of reducing 2.3.5.6-titrachloropyridine with zinc (USP
No. 4259495, No. 4258194, No. 41119
38) and the method using 2-amino-3,5-dichloropyridine as a starting material (Brit PA 1215387
Another method is to oxidize 2.3.5-trichloro-6-hydrazinopyridine and 2.3.5-trichloro-4-hydrazinopyridine with sodium hypochlorite in a solvent. There is (USP No. 4127575). The starting material for this process, hydrazinopyridine, is easily obtained by reaction of chloropyridine with hydrazine hydrate (J, Chea+.
Ｓｏｃ、、（Ｃ）＋ １９７Ｌ １６７）。Soc,, (C) + 197L 167).
しかしながら、ピリジン及びピリジン塩酸塩の液相塩素
化とピリジン塩素化物の気相塩素化による方法は、ピリ
ジン塩素化物が多種に渡って生成したり、もしくは気相
反応であるがゆえに工程や反応装置が複雑であった。２
．３．５．６−テトラクロロピリジンを亜鉛により還元
する方法は生成する亜鉛塩の毒性のために、排水処理等
の問題がある。また２−アミノ−３，５−ジクロロピリ
ジンを塩素化する方法では原料が高価であり、コスト面
で不利である。ヒドラジノピリジンを次亜塩素酸ソーダ
で酸化する方法は、目的物への選択率の点においては非
常によいが、反応器等の材質は安価なステンレス製では
腐食の問題より使用できない。またトルエンなど大量の
溶媒を用い、かつ次亜塩素酸ソーダは１５％水溶液であ
るために、いわゆる空時収率が悪い。However, the liquid-phase chlorination of pyridine and pyridine hydrochloride and the gas-phase chlorination of pyridine chloride produce a wide variety of pyridine chlorides, or the process and reaction equipment are complicated because the reaction is a gas-phase reaction. It was complicated. 2
．． The method of reducing 3.5.6-tetrachloropyridine with zinc has problems such as wastewater treatment due to the toxicity of the zinc salt produced. Furthermore, the method of chlorinating 2-amino-3,5-dichloropyridine requires expensive raw materials, which is disadvantageous in terms of cost. The method of oxidizing hydrazinopyridine with sodium hypochlorite is very good in terms of selectivity to the target product, but if the reactor is made of inexpensive stainless steel, it cannot be used due to corrosion problems. Furthermore, since a large amount of solvent such as toluene is used and sodium hypochlorite is a 15% aqueous solution, the so-called space-time yield is poor.
さらに次亜塩素酸ソーダは過酸化水素よりも高価であり
、また使用率も高いためにコスト面でも不利である。Furthermore, sodium hypochlorite is more expensive than hydrogen peroxide and has a higher usage rate, so it is disadvantageous in terms of cost.
本発明者らは下記−形式（Ｉ）で表されるヒドラジノピ
リジンを用いてピリジン塩素化物の工業的製造法を鋭意
検討した結果、本発明を完成するに至った。The present inventors have completed the present invention as a result of intensive studies on an industrial method for producing chlorinated pyridine using hydrazinopyridine represented by the following formula (I).
Ｘ。X.
〔ここでＸ１〜Ｘ、は同−又は異なるものであって、塩
素原子、水素原子又はヒドラジノ基（−ＮＨＮＨ，）を
表わす。但し記号ｘ１〜Ｘ、のうちの少なくとも１つは
ヒドラジノ基（ＮＨＮＨｚ）を表わすものとし、またに
１〜ｘ５のうち少なくとも１つは塩素原子を表わすもの
とする。〕
すなわち、本発明は上記−形式（Ｉ）で表されるヒドラ
ジノピリジンを溶媒中、過酸化水素で酸化することを特
徴とするピリジン塩素化物の製造法を提供するものであ
る。[Here, X1 to X are the same or different and represent a chlorine atom, a hydrogen atom, or a hydrazino group (-NHNH,). However, at least one of the symbols x1 to X represents a hydrazino group (NHNHz), and at least one of the symbols 1 to x5 represents a chlorine atom. That is, the present invention provides a method for producing a pyridine chloride, which comprises oxidizing hydrazinopyridine represented by the above-mentioned formula (I) with hydrogen peroxide in a solvent.
本発明で用いられる溶媒としては、原料であるヒドラジ
ノピリジンを溶解及び分散させるものであれば、いずれ
も使用できるが、好ましくは、水、四塩化炭素、クロロ
ホルム、塩化メチレン、ジクロロエタン、トルエン、ジ
オキサン等が用いられ、特に安全性及び収率の点で水が
より好ましい。As the solvent used in the present invention, any solvent that can dissolve and disperse the raw material hydrazinopyridine can be used, but water, carbon tetrachloride, chloroform, methylene chloride, dichloroethane, toluene, and dioxane are preferably used. Water is particularly preferred in terms of safety and yield.
本発明の方法において、反応は通常０〜２００°Ｃ１好
ましくは５０〜１２０°Ｃの温度範囲で行われる。In the method of the present invention, the reaction is generally carried out at a temperature range of 0 to 200°C, preferably 50 to 120°C.
本発明の方法において、溶媒の使用量は通常ヒドラジノ
ピリジンに対して２〜２０重量倍、望ましくは２〜１０
重量倍である。また、過酸化水素の使用量は、通常ヒド
ラジノピリジンに対しテ１．０〜２．５モル倍、望まし
くは等モルであって、普通１−１５時間で滴下する。In the method of the present invention, the amount of the solvent used is usually 2 to 20 times the weight of hydrazinopyridine, preferably 2 to 10 times the weight of hydrazinopyridine.
It is twice the weight. The amount of hydrogen peroxide to be used is usually 1.0 to 2.5 moles, preferably equimolar, to hydrazinopyridine, and the hydrogen peroxide is added dropwise usually over a period of 1 to 15 hours.
本発明の反応を行うのに、水酸化ナトリウムや炭酸ナト
リウムなどの塩基性物質の添加は必ずしも必要ではない
が、添加することにより反応は促進される。Although the addition of a basic substance such as sodium hydroxide or sodium carbonate is not necessarily necessary to carry out the reaction of the present invention, the reaction is accelerated by the addition.
過酸化水素の滴下終了後、反応液に抽出溶媒を加えて、
抽出・蒸留などの通常行われる分離操作を行うことによ
り、純度９９％以上の目的物であるピリジン塩素化物を
９８％以上の高収率で得ることができる。After dropping the hydrogen peroxide, add the extraction solvent to the reaction solution,
By performing commonly performed separation operations such as extraction and distillation, a chlorinated pyridine product having a purity of 99% or more and a target product can be obtained at a high yield of 98% or more.
本発明の方法によれば、安価な材質を用いた簡便なプロ
セスにより、反応・後処理が実施でき、また極めて高い
選択性及び空時収率でかつ安価に目的とするピリジン塩
素化物を製造することができる。According to the method of the present invention, the reaction and post-treatment can be carried out through a simple process using inexpensive materials, and the desired pyridine chloride can be produced at low cost with extremely high selectivity and space-time yield. be able to.
以下、実施例により本発明を更に詳細に説明するが、本
発明はこれらの実施例に限定されるものではない。EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.
実施例１
還流管、滴下ロート、温度計及び撹拌機を備えた３００
−の４つ目フラスコに、２．３．５− ）リクロロー６
−ヒドラジノビリジン４２．５ｇ（０，２モル）、水１
２８．０ｇ、水酸化ナトリウム８．０ ｇ （０，２モ
ル）及び四塩化炭素６．０ｇを仕込み加熱還流させた。Example 1 300 equipped with reflux tube, dropping funnel, thermometer and stirrer
- into the fourth flask, 2.3.5-) Rechloro 6
- hydrazinoviridine 42.5 g (0.2 mol), water 1
28.0 g of sodium hydroxide, 8.0 g (0.2 mol) of sodium hydroxide, and 6.0 g of carbon tetrachloride were charged and heated to reflux.
そこに３５％過酸化水素水溶液２３．３ｇを５時間かけ
て滴下した。反応終了後、四塩化炭素３０ｇを加えて抽
出後、濃縮・分留することにより、２，３．５− ）リ
クロロピリジン３５．９ｇ （収率９８％、純度９９．
５％）が得られた。23.3 g of a 35% aqueous hydrogen peroxide solution was added dropwise thereto over 5 hours. After the reaction was completed, 30 g of carbon tetrachloride was added and extracted, followed by concentration and fractional distillation to obtain 35.9 g of 2,3.5-)lichloropyridine (yield 98%, purity 99.
5%) was obtained.
実施例２
還流管、滴下ロート、温度計及び撹拌機を備えた３００
−の４つロフラスコに、３．６−ジクロロ−２−ヒドラ
ジノピリジン３５．６ ｇ （０，２モル）、水１２８
．０ ｇ、水酸化ナトリウム８．０ ｇ （０，２モル
）及び四塩化炭素６．０ｇを仕込み加熱還流させた。Example 2 300 equipped with reflux tube, dropping funnel, thermometer and stirrer
35.6 g (0.2 mol) of 3,6-dichloro-2-hydrazinopyridine, 128 g of water
．． 0 g, 8.0 g (0.2 mol) of sodium hydroxide, and 6.0 g of carbon tetrachloride were charged and heated to reflux.
そこに３５％過酸化水素水溶液２３．３ ｇを５時間か
けて滴下した。23.3 g of a 35% aqueous hydrogen peroxide solution was added dropwise thereto over 5 hours.
反応終了後、四塩化炭素３０ｇを加えて抽出後、濃縮・
分留することにより、２．５−ジクロロピリジン２９．
３ｇ （収率９８％、純度９９．０％）が得られた。After the reaction is complete, add 30g of carbon tetrachloride, extract, and concentrate.
By fractional distillation, 2,5-dichloropyridine 29.
3 g (yield 98%, purity 99.0%) was obtained.
実施例３
前記実施例２において３．６−ジクロロ−２ヒドラジノ
ピリジンの代わりに３．５−ジクロロ２−ヒドラジノピ
リジンを使用することを除いては実施例２の場合と同様
に反応処理した。Example 3 A reaction treatment was carried out in the same manner as in Example 2 except that 3,5-dichloro-2-hydrazinopyridine was used instead of 3,6-dichloro-2hydrazinopyridine in Example 2. .
その結果３．５−ジクロロピリジン２８．５ｇ （収率
９５．１％、純度９８．８％）が得られた。As a result, 28.5 g of 3,5-dichloropyridine (yield 95.1%, purity 98.8%) was obtained.
Claims (1)
、塩素原子、水素原子又はヒドラジノ基（−ＮＨＮＨ＿
２）を表わす、但し記号Ｘ＿１〜Ｘ＿５のうちの少なく
とも１つはヒドラジノ基（−ＮＨＮＨ＿２）を表わすも
のとし、またＸ＿１〜Ｘ＿５のうち少なくとも１つは塩
素原子を表わすものとする。〕 で表されるヒドラジノピリジンを、溶媒中、過酸化水素
で酸化することを特徴とするピリジン塩素化物の製造法
。[Claims] General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [Here, X_1 to X_5 are the same or different, and are chlorine atoms, hydrogen atoms, or hydrazino groups (-NHNH_
2), provided that at least one of the symbols X_1 to X_5 represents a hydrazino group (-NHNH_2), and at least one of the symbols X_1 to X_5 represents a chlorine atom. ] A method for producing a pyridine chloride, which comprises oxidizing hydrazinopyridine represented by the following with hydrogen peroxide in a solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34467989A JP2716826B2 (en) | 1989-12-27 | 1989-12-27 | Method for producing chlorinated pyridine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34467989A JP2716826B2 (en) | 1989-12-27 | 1989-12-27 | Method for producing chlorinated pyridine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03200769A true JPH03200769A (en) | 1991-09-02 |
| JP2716826B2 JP2716826B2 (en) | 1998-02-18 |
Family
ID=18371142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP34467989A Expired - Fee Related JP2716826B2 (en) | 1989-12-27 | 1989-12-27 | Method for producing chlorinated pyridine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2716826B2 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0930300A1 (en) * | 1997-12-16 | 1999-07-21 | DAICEL CHEMICAL INDUSTRIES, Ltd. | Process for preparing (poly)chloropyridines |
| US6184384B1 (en) | 1998-07-15 | 2001-02-06 | Reilly Industries, Inc. | Dechlorination of pyridines in acidic, zinc-containing mediums |
| CN104115042A (en) * | 2012-03-19 | 2014-10-22 | 日本化药株式会社 | Dye-Based Polarizers and Polarizers |
| CN107778225A (en) * | 2016-08-26 | 2018-03-09 | 上海雅本化学有限公司 | A kind of preparation method of the chloropyridine of 2 diazanyl 3 |
| CN108358835A (en) * | 2018-02-24 | 2018-08-03 | 利尔化学股份有限公司 | A kind of preparation method of 2,3,5- trichloropyridines |
| CN108912043A (en) * | 2018-08-31 | 2018-11-30 | 江苏富鼎化学有限公司 | A kind of synthetic method of 2,3,5- trichloropyridine |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4127575A (en) | 1976-10-20 | 1978-11-28 | The Dow Chemical Company | Preparation of chloro substituted pyridines |
-
1989
- 1989-12-27 JP JP34467989A patent/JP2716826B2/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0930300A1 (en) * | 1997-12-16 | 1999-07-21 | DAICEL CHEMICAL INDUSTRIES, Ltd. | Process for preparing (poly)chloropyridines |
| US5977370A (en) * | 1997-12-16 | 1999-11-02 | Daicel Chemical Industries, Ltd. | Process for preparing pyridine chloride |
| US6184384B1 (en) | 1998-07-15 | 2001-02-06 | Reilly Industries, Inc. | Dechlorination of pyridines in acidic, zinc-containing mediums |
| CN104115042A (en) * | 2012-03-19 | 2014-10-22 | 日本化药株式会社 | Dye-Based Polarizers and Polarizers |
| CN107778225A (en) * | 2016-08-26 | 2018-03-09 | 上海雅本化学有限公司 | A kind of preparation method of the chloropyridine of 2 diazanyl 3 |
| CN108358835A (en) * | 2018-02-24 | 2018-08-03 | 利尔化学股份有限公司 | A kind of preparation method of 2,3,5- trichloropyridines |
| CN108912043A (en) * | 2018-08-31 | 2018-11-30 | 江苏富鼎化学有限公司 | A kind of synthetic method of 2,3,5- trichloropyridine |
| CN108912043B (en) * | 2018-08-31 | 2021-11-30 | 江苏富鼎化学有限公司 | Synthetic method of 2,3, 5-trichloropyridine |
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| Publication number | Publication date |
|---|---|
| JP2716826B2 (en) | 1998-02-18 |
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