JPS63275565A - Production of 2,3,5-trichloropyridine - Google Patents
Production of 2,3,5-trichloropyridineInfo
- Publication number
- JPS63275565A JPS63275565A JP62108564A JP10856487A JPS63275565A JP S63275565 A JPS63275565 A JP S63275565A JP 62108564 A JP62108564 A JP 62108564A JP 10856487 A JP10856487 A JP 10856487A JP S63275565 A JPS63275565 A JP S63275565A
- Authority
- JP
- Japan
- Prior art keywords
- tetrachloropyridine
- catalyst
- reacting
- raw material
- produced
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- CNLIIAKAAMFCJG-UHFFFAOYSA-N 2,3,5-trichloropyridine Chemical compound ClC1=CN=C(Cl)C(Cl)=C1 CNLIIAKAAMFCJG-UHFFFAOYSA-N 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- FATBKZJZAHWCSL-UHFFFAOYSA-N 2,3,5,6-tetrachloropyridine Chemical compound ClC1=CC(Cl)=C(Cl)N=C1Cl FATBKZJZAHWCSL-UHFFFAOYSA-N 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- VMHZXXPDUOVTHD-UHFFFAOYSA-N 2,3,4-trichloropyridine Chemical compound ClC1=CC=NC(Cl)=C1Cl VMHZXXPDUOVTHD-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 14
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 4
- 229910052697 platinum Inorganic materials 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 3
- 229910052763 palladium Inorganic materials 0.000 abstract description 3
- 238000010531 catalytic reduction reaction Methods 0.000 abstract description 2
- 238000004821 distillation Methods 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract description 2
- 239000002351 wastewater Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 239000003905 agrochemical Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 235000017550 sodium carbonate Nutrition 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- MAKFMOSBBNKPMS-UHFFFAOYSA-N 2,3-dichloropyridine Chemical compound ClC1=CC=CN=C1Cl MAKFMOSBBNKPMS-UHFFFAOYSA-N 0.000 description 5
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical group NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- -1 lithium aluminum hydride Chemical compound 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNDPLEAVNVOOQZ-UHFFFAOYSA-N 2,3,4,5,6-pentachloropyridine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=C1Cl DNDPLEAVNVOOQZ-UHFFFAOYSA-N 0.000 description 1
- DLOOKZXVYJHDIY-UHFFFAOYSA-N 2,3,4,5-tetrachloropyridine Chemical compound ClC1=CN=C(Cl)C(Cl)=C1Cl DLOOKZXVYJHDIY-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (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２，３゜５−
トリクロロピリシンを製造する方法に関する。Detailed Description of the Invention (Industrial Application Field) The present invention provides 2,3°5-
The present invention relates to a method for producing trichloropyricin.
（従来技術）
２．３．５− ）リクロロビリノンの製造法はいくつか
知られている。しかし、収率が良く、プロセスも効率が
良いという例は少なく、実際に工業化が困難と考えられ
る例が多い。比較的、効率の良い例としては、２−ピリ
ドン又は２−アミノピリジンの３位、５位を塩素化した
後、２位の水酸基（カルボニル基）、アミン基を塩素化
する方法がある。（英国特許１，２１５，３８７．特開
昭５３−６８７８３、特開昭５４−５９２８３、米国特
許４２８７３４７）又、２．３，５．６−チトラクロロ
ピリゾンのα位を還元する方法もある。還元剤としては
、亜鉛（Ｊ、 Ｈｅｔｅｒｏ−ｃｙｃｌＣｈｅｍ １７
．４９３．米国特許４２５９４９５．４２５８１９４．
４１１１９３８）、電解法（Ｅｕｒ、 Ｐａｔ。(Prior Art) 2.3.5-) Several methods for producing lichlorovirinone are known. However, there are few examples in which the yield is good and the process is efficient, and there are many cases in which industrialization is considered difficult. A relatively efficient example is a method of chlorinating the 3-position and 5-position of 2-pyridone or 2-aminopyridine, and then chlorinating the hydroxyl group (carbonyl group) and amine group at the 2-position. (British Patent No. 1,215,387, JP-A-53-68783, JP-A-54-59283, US Pat. No. 4,287,347) There is also a method of reducing the α-position of 2,3,5,6-titrachloropyridone. . As a reducing agent, zinc (J, Hetero-cycleChem 17
．． 493. U.S. Patent 4259495.4258194.
4111938), electrolytic method (Eur, Pat.
１８０６９ ）、水素化リチウムアルミニウム（Ｊ、Ｃ
，Ｓ。18069), lithium aluminum hydride (J, C
,S.
Ｄ（２０） １２１１ ）などが用いられている。D(20) 1211) etc. are used.
（発明が解決しようとする問題点）
前記の２−ピリドン、２−アミノピリジンの塩素化法は
、原料が高価であり、かつ反応工程が長いためコスト面
で不利である。２．３．５．６−チトラクロロビリジン
は比較的安価に入手可能であるが、これまで知られてい
る還元法は、大量の溶媒を用いる必要があり、いわゆる
空時収率が悪い。又、還元剤として亜鉛を用いる場合、
当量必要であり、多量に生成する亜鉛塩の毒性のため、
排水により河川が汚染されるため、工業的に実施する場
合は亜鉛を回収することが必要となる。(Problems to be Solved by the Invention) The above-mentioned method for chlorinating 2-pyridone and 2-aminopyridine is disadvantageous in terms of cost because the raw materials are expensive and the reaction process is long. 2.3.5.6-Titrachloropyridine is available at a relatively low cost, but the reduction methods known so far require the use of a large amount of solvent and have poor space-time yields. Also, when using zinc as a reducing agent,
Because of the toxicity of zinc salts, which require equivalent amounts and are produced in large quantities,
Since rivers are polluted by wastewater, it is necessary to recover zinc if it is to be implemented industrially.
（問題を解決するための手段）
発明者らは２．３，５．６−チトラクロロビリジンを用
いて、効率が良く、かつ排水等の公害問題の生ずること
のない、２，３．５− ）ジクロロビリジンの製造法を
鋭意検討した結果、本発明に至った。即ち、２．３，５
．６−テトラクロロピリジンをパラジウム、白金などの
白金属、又はラネーニッケルなどの触媒存在下、水素と
接触させることを特徴とする方法である。２．３，５．
６−テトラクロロピリジンの水素接触還元法については
従来１例がなく、本発明が初めての例である。(Means for Solving the Problem) The inventors used 2,3,5,6-titrachloropyridine to develop a 2,3,5- ) As a result of intensive studies on the method for producing dichloropyridine, the present invention was achieved. That is, 2.3,5
．． This method is characterized by contacting 6-tetrachloropyridine with hydrogen in the presence of a platinum metal such as palladium or platinum, or a catalyst such as Raney nickel. 2.3,5.
There has been no prior example of hydrogen catalytic reduction of 6-tetrachloropyridine, and the present invention is the first such method.
触媒としては、先に述べたように、ノクラ・ゾウム、白
金、ルテニウム、ロジウムなどの白金属、又はラネーニ
ッケル、ラネー銅等のラネー系触媒が用いられる。As the catalyst, as mentioned above, platinum metals such as Noclazoum, platinum, ruthenium, and rhodium, or Raney catalysts such as Raney nickel and Raney copper are used.
溶媒としては、ヘキサン、ヘプタンのような炭化水素類
、メタノール、エタノール、イソプロピルアルコールの
ようなアルコール類、ギ酸、酢酸のような有機酸、酢酸
エチルのようなエステルなどを使用できる。その量は２
，３，５．６−テトラクロロピリジンを溶解させるに足
る量で良く、通常、２．３．５．６−テトラクロロピリ
ジンに対して、０．５〜３重量倍用いられる。なお、酢
酸す） ＩＪウム、トリエチルアミン、炭酸ナトリウム
などの塩基の添加によって反応はさらに促進される。反
応温度は、実質的に反応が進行する最低温度以上、及び
、ある程度の選択性を保ちかつ工業的に容易に実施でき
る温度範囲として、通常０℃〜１５０℃の間で行なわれ
る。圧力は常圧、加圧どちらにおいても実施できる。長
時間の反応では、目的物の２，３゜５−トリクロロピリ
ノンがさらに還元される恐れがあるため、進行度をＧＣ
クロマトグラフィー等でチェックし、最も経済的な組成
で反応を停止するべきである。通常、２，６−ジクロロ
ビリジン。As the solvent, hydrocarbons such as hexane and heptane, alcohols such as methanol, ethanol and isopropyl alcohol, organic acids such as formic acid and acetic acid, and esters such as ethyl acetate can be used. The amount is 2
, 3,5,6-tetrachloropyridine, and is usually used in an amount of 0.5 to 3 times the weight of 2,3,5,6-tetrachloropyridine. The reaction is further promoted by the addition of a base such as acetic acid, triethylamine, or sodium carbonate. The reaction temperature is generally between 0° C. and 150° C., which is the minimum temperature at which the reaction substantially proceeds, and a temperature range that can be easily carried out industrially while maintaining a certain degree of selectivity. The pressure can be either normal pressure or increased pressure. In long-term reactions, there is a risk that the target product, 2,3°5-trichloropyrinone, may be further reduced, so the progress is monitored by GC.
The reaction should be stopped using the most economical composition after checking with chromatography. Usually 2,6-dichloroviridine.
２．３．６− ）ジクロロビリジン等が若干副生ずるが
、これらは蒸留により目的物である２、３．５− ）ジ
クロロビリジンと分離でき、さらに塩素を作用させるこ
とにより、出発物である２、３，５．６−テトラクロロ
ぎリジンとして回収可能である。2.3.6-) Dichloropyridine and the like are slightly produced as by-products, but these can be separated from the target product 2,3.5-) dichloropyridine by distillation, and by further action with chlorine, the starting material 2 , 3,5.6-tetrachlorogylysine.
反応後の後処理法としては、触媒を口過、又はデカンテ
ーションで除去（これは再使用できる）した後、溶媒を
留去し、水洗浄により塩基物を分り除去した後、分留又
は再結晶により精製する方法が効率的である。After the reaction, the post-treatment method is to remove the catalyst by filtration or decantation (this can be reused), distill off the solvent, separate and remove the base by washing with water, and then perform fractional distillation or re-treatment. The method of purification by crystallization is efficient.
（発明の効果）
本発明の方法によれば、安価な原料である２、３゜５．
６−テトラクロロピリジンを用いて反応、後処理が簡便
であυ、副生物を原料として回収することができる効率
的なプロセスにより２，３．５− ）ジクロロビリジン
をつくることができる。又、亜鉛使用の場合のような排
水等の公害問題もない。(Effects of the Invention) According to the method of the present invention, 2.3°5.
Using 6-tetrachloropyridine, 2,3.5-) dichloropyridine can be produced through an efficient process in which the reaction and post-treatment are simple and by-products can be recovered as raw materials. Also, there is no pollution problem such as drainage, which is the case when zinc is used.
（実施例）
次に本発明を実施例に基すきさらに詳細に説明する。反
応は３００＋＋ＪＳＵＳ製のオートクレーブを用い、２
，３，５．６−チトラクロロピリソ／（純度９６．８％
、その他不純物として、２，３．６− ）ジクロロビリ
ジン１．５ ％ 、ペンタクロロビリジン１．フチを含
む）を２６．２＆（１，２モル）、溶媒をテトラクロロ
ピリノンに対して３重量倍、触媒として湿５ ％ Ｐｄ
／Ｃ（含水率５０％）１．３＆仕込んだ。又各種塩基の
添加量は、テトラクロロピリジンに対して等モルを用い
た。水素圧は室温で、初圧１５に９／ｙｎ２とし、５０
℃まで昇温しその温度で圧力がＯになるか又は圧力降下
が止まるまで反応させた。(Examples) Next, the present invention will be explained in more detail based on Examples. The reaction was carried out using a 300++ JSUS autoclave.
,3,5.6-titrachloropyriso/(purity 96.8%
, other impurities include 1.5% of 2,3.6-) dichloropyridine, 1.5% of pentachloropyridine. (including edges) is 26.2 & (1.2 mol), the solvent is 3 times the weight of tetrachloropyrinone, and the catalyst is 5% Pd.
/C (water content 50%) 1.3& was charged. Further, the amount of each base added was equimolar to tetrachloropyridine. The hydrogen pressure is at room temperature, the initial pressure is 15 and 9/yn2, and the hydrogen pressure is 50
The temperature was raised to 0.degree. C., and the reaction was carried out at that temperature until the pressure reached 0 or the pressure drop stopped.
結果を次表にまとめる。The results are summarized in the table below.
Claims (1)
、水素と反応せしめることを特徴とする、２，３，５−
トリクロロピリジンの製造法2,3,5-, characterized by reacting 2,3,5,6-tetrachloropyridine with hydrogen in the presence of a catalyst.
Production method of trichloropyridine
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62108564A JPH0791270B2 (en) | 1987-05-01 | 1987-05-01 | Method for producing 2,3,5-trichloropyridine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62108564A JPH0791270B2 (en) | 1987-05-01 | 1987-05-01 | Method for producing 2,3,5-trichloropyridine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63275565A true JPS63275565A (en) | 1988-11-14 |
| JPH0791270B2 JPH0791270B2 (en) | 1995-10-04 |
Family
ID=14488023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62108564A Expired - Lifetime JPH0791270B2 (en) | 1987-05-01 | 1987-05-01 | Method for producing 2,3,5-trichloropyridine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0791270B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6051714A (en) * | 1998-03-12 | 2000-04-18 | Reilly Industries, Inc. | Processes for dechlorinating pyridines |
| CN103664755A (en) * | 2013-12-31 | 2014-03-26 | 沈阳化工研究院有限公司 | Preparation method of dichloromethyl substituted pyridine |
| CN106866647A (en) * | 2017-03-31 | 2017-06-20 | 九江善水科技股份有限公司 | The synthetic method of Yi Zhong Evil grass ethers and its trichloropyridine of intermediate 2,3,5 |
| CN108341767A (en) * | 2017-01-24 | 2018-07-31 | 盐城恒盛化工有限公司 | A method of preparing 2,3,5- trichloropyridines |
| CN110551062A (en) * | 2019-09-16 | 2019-12-10 | 西安凯立新材料股份有限公司 | Method for preparing 2,3, 5-trichloropyridine by adopting 2,3,5, 6-tetrachloropyridine |
-
1987
- 1987-05-01 JP JP62108564A patent/JPH0791270B2/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6051714A (en) * | 1998-03-12 | 2000-04-18 | Reilly Industries, Inc. | Processes for dechlorinating pyridines |
| CN103664755A (en) * | 2013-12-31 | 2014-03-26 | 沈阳化工研究院有限公司 | Preparation method of dichloromethyl substituted pyridine |
| CN108341767A (en) * | 2017-01-24 | 2018-07-31 | 盐城恒盛化工有限公司 | A method of preparing 2,3,5- trichloropyridines |
| CN106866647A (en) * | 2017-03-31 | 2017-06-20 | 九江善水科技股份有限公司 | The synthetic method of Yi Zhong Evil grass ethers and its trichloropyridine of intermediate 2,3,5 |
| CN110551062A (en) * | 2019-09-16 | 2019-12-10 | 西安凯立新材料股份有限公司 | Method for preparing 2,3, 5-trichloropyridine by adopting 2,3,5, 6-tetrachloropyridine |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0791270B2 (en) | 1995-10-04 |
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