JPH01157922A - Production of nitrile compound - Google Patents
Production of nitrile compoundInfo
- Publication number
- JPH01157922A JPH01157922A JP31682687A JP31682687A JPH01157922A JP H01157922 A JPH01157922 A JP H01157922A JP 31682687 A JP31682687 A JP 31682687A JP 31682687 A JP31682687 A JP 31682687A JP H01157922 A JPH01157922 A JP H01157922A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- nitrile
- hydrazone
- thermal decomposition
- aldehyde
- 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.)
- Pending
Links
- -1 nitrile compound Chemical class 0.000 title claims abstract description 65
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000005979 thermal decomposition reaction Methods 0.000 claims abstract description 7
- 230000002378 acidificating effect Effects 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 4
- 150000003335 secondary amines Chemical class 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- CGTWOOPTAAXMLM-UHFFFAOYSA-N carbazol-9-amine Chemical compound C1=CC=C2N(N)C3=CC=CC=C3C2=C1 CGTWOOPTAAXMLM-UHFFFAOYSA-N 0.000 abstract description 2
- 239000012159 carrier gas Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 10
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 4
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- LLSYZMNMWXDYMT-UHFFFAOYSA-N pyrene-1-carbonitrile Chemical compound C1=C2C(C#N)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 LLSYZMNMWXDYMT-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- YBQZXXMEJHZYMB-UHFFFAOYSA-N 1,2-diphenylhydrazine Chemical compound C=1C=CC=CC=1NNC1=CC=CC=C1 YBQZXXMEJHZYMB-UHFFFAOYSA-N 0.000 description 1
- XFVZSRRZZNLWBW-UHFFFAOYSA-N 4-(Diethylamino)salicylaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C(O)=C1 XFVZSRRZZNLWBW-UHFFFAOYSA-N 0.000 description 1
- GDAGABLETWOYOK-UHFFFAOYSA-N 4-(diethylamino)-2-hydroxybenzonitrile Chemical compound CCN(CC)C1=CC=C(C#N)C(O)=C1 GDAGABLETWOYOK-UHFFFAOYSA-N 0.000 description 1
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 description 1
- KMLGFOAKCYHXCQ-UHFFFAOYSA-N 4-(diethylamino)benzonitrile Chemical compound CCN(CC)C1=CC=C(C#N)C=C1 KMLGFOAKCYHXCQ-UHFFFAOYSA-N 0.000 description 1
- QGJXVBICNCIWEL-UHFFFAOYSA-N 9-ethylcarbazole-3-carbaldehyde Chemical compound O=CC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 QGJXVBICNCIWEL-UHFFFAOYSA-N 0.000 description 1
- WMRDSAJESGGFHQ-UHFFFAOYSA-N 9-ethylcarbazole-3-carbonitrile Chemical compound N#CC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 WMRDSAJESGGFHQ-UHFFFAOYSA-N 0.000 description 1
- GWTCYEKJBUXRTD-UHFFFAOYSA-N 9h-carbazole-1-carbonitrile Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C#N GWTCYEKJBUXRTD-UHFFFAOYSA-N 0.000 description 1
- DFRVZIVYWKYYEV-UHFFFAOYSA-N OC1=CC(N(CC)CC)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound OC1=CC(N(CC)CC)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 DFRVZIVYWKYYEV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XFJPUTGGRPTSHI-UHFFFAOYSA-N n-phenyl-n-(pyren-1-ylmethylideneamino)aniline Chemical compound C=1C=C(C2=C34)C=CC3=CC=CC4=CC=C2C=1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 XFJPUTGGRPTSHI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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〕
本発明はアルデヒド化合物より二ｌ−ＩＪル化合物を合
成する製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a manufacturing method for synthesizing a di-IJ compound from an aldehyde compound.
ニトリル化合物は還元するとアミンに、また加水分解す
るとアミドに化学変化する。ニトリル化合物を始めアミ
ンやアミドは農薬や唄薬の製造工程で反応物の中間体と
して多く用いられている。Nitrile compounds chemically change to amines when reduced and to amides when hydrolyzed. Nitrile compounds, amines, and amides are often used as intermediates for reactants in the manufacturing process of agricultural chemicals and potions.
このようにニトリル化合物は中間体として重要な物質で
ある。In this way, nitrile compounds are important substances as intermediates.
ニトリル化合物の製造方法としては不飽和結合に青酸塩
を付加する方法（１）
Ｈ−ＣミＣＨ＋ＨＣＮ ＋ＣＨ２＝ＣＨＣＮ ・
・・け）△
有機ハロゲン化物あるいは有機ジアゾニウム塩に青酸塩
を反応させて置換する方法（２）更には有機オキシムの
脱水反応により生成する方法（３）がある。A method for producing a nitrile compound is a method of adding cyanide to an unsaturated bond (1) H-CmiCH+HCN +CH2=CHCN ・
There is a method (2) in which an organic halide or an organic diazonium salt is reacted with cyanide to replace it, and a method (3) in which the organic oxime is produced by a dehydration reaction.
Ｒ−ＣＨ＝ＮＯＨ＋（ＣＨ３Ｃｏ）２０ −＋ＲＣＮ
・・・（３）前記（１）、（２）の製造方法におい
て青酸塩は大変毒性が高いのでこれを反応に用いること
は危険である。また、前記（３）のオキシムの脱水反応
において、反応系に無水物が存在するため、生成物はニ
トリル化合物と酸無水物の混合物となり、ニトリル化合
物のみな単離するのは困難である。R-CH=NOH+(CH3Co)20-+RCN
(3) In the production methods of (1) and (2) above, cyanide is highly toxic, so it is dangerous to use it in the reaction. Further, in the dehydration reaction of oxime (3), since an anhydride is present in the reaction system, the product is a mixture of a nitrile compound and an acid anhydride, and it is difficult to isolate all the nitrile compound.
また、有機ハロゲン化物あるいは有機ジアゾニウム塩か
らニトリル化合物を合成する場合において、生成物に塩
が混ってしまうといった欠点があった。Furthermore, when a nitrile compound is synthesized from an organic halide or an organic diazonium salt, there is a drawback that salt is mixed into the product.
本発明は従来の問題点を解消させ、毒性の低いアルデヒ
ド化合物からニトリル化合物を合成するニトリル化合物
の製造方法の提供を目的とする。The present invention aims to solve the conventional problems and provide a method for producing a nitrile compound by synthesizing a nitrile compound from an aldehyde compound with low toxicity.
本発明はアルデヒド化合物にヒドラジン化合物を酸性触
媒下で反応させてヒドラゾン化合物を合成し、このヒド
ラゾン化合物を熱分解しニトリル化合物と２級アミンを
合成した後、ニトリル化合物と２級アミンを分離し、ニ
トリル化合物のみを／Ｒ’
→Ｒ−Ｃ＝Ｎ＋Ｈ−Ｎ → Ｒ−ＣミＮΔ
ゝＷ
Ｒ％Ｒ′、Ｋ：アルキル基、置換基を含んでも良いフェ
ニル基
〔実施例〕
（実施例１）
以下、本発明の実施例を反応式を用いて説明する。アル
デヒド化合物としてｐ−ジエチルアミノベンズアルデヒ
ド（Ａ）１０．０．９（５，６５Ｘ１０ ｍｏｌ ）
−と、ヒドラジン化合物としてＮ−アミノカルバゾール
［Ｂｌ １０．３ 、！ｉ’ （５，６５Ｘ １０
ｍｏｌ ）と、酸性触媒トしてｐ−トルエンスルホン酸
触媒量をベンゼンａｏｍｚ と共に加え、９５〜１０
５℃で生じる水を共沸除去しながら５時間反応させ、ヒ
ドラゾン化合物であるｐ−ジエチルアミノベンズアルデ
ヒドカルバゾールヒドラゾン（Ｑを合成する。The present invention synthesizes a hydrazone compound by reacting an aldehyde compound with a hydrazine compound under an acidic catalyst, thermally decomposes this hydrazone compound to synthesize a nitrile compound and a secondary amine, and then separates the nitrile compound and the secondary amine. Nitrile compound only/R' → R−C=N+H−N → R−CmiNΔ
W R% R', K: Alkyl group, phenyl group which may contain a substituent [Example] (Example 1) Examples of the present invention will be described below using reaction formulas. p-diethylaminobenzaldehyde (A) 10.0.9 (5,65X10 mol) as an aldehyde compound
- and N-aminocarbazole [Bl 10.3,! as a hydrazine compound. i' (5,65X 10
mol) and an acidic catalyst, a catalytic amount of p-toluenesulfonic acid was added together with benzene aomz, and 95 to 10
The reaction is carried out for 5 hours while water generated at 5° C. is azeotropically removed to synthesize p-diethylaminobenzaldehyde carbazole hydrazone (Q), which is a hydrazone compound.
このときの収量は１１．５ｇ（収率５９．７％）であっ
た。シリコン０ｖ−１を充填したカラム中を窒素をキャ
リヤガスとして、・ｐ−ジエチルアミノベンズアルデヒ
ドカルバゾールヒドラゾン（ｑを温度２５０℃で通過さ
せながら熱分解を行う。The yield at this time was 11.5 g (yield 59.7%). Thermal decomposition is carried out while passing p-diethylaminobenzaldehyde carbazole hydrazone (q) through a column filled with silicon 0v-1 using nitrogen as a carrier gas at a temperature of 250°C.
熱分解で生成するｐ−ジエチルアミノベンゾニトリル（
至）とカルバゾール（ト）は、カラム通過により、それ
ぞれを単離することができる。このｇきの収率は、ｐ−
ジエチルアミノベンゾニトリル銭が５５％、カルバゾー
ル［Ｆ］が５５％であった。このようにアルデヒド化合
物とヒドラジン化合物から（実施例２）
アルデヒド化合物として９−エチル−３−カルバゾール
カルボキシアルデヒド（Ｆを用いた他は実施例１と同様
の反応を行い、９−エチル−３−カルバゾールカルボキ
シアルデヒドカルバゾールヒドラゾン（Ｇを合成する。p-diethylaminobenzonitrile produced by thermal decomposition (
) and carbazole (t) can be isolated by passing through a column. The yield of this g-
Diethylaminobenzonitrile was 55%, and carbazole [F] was 55%. In this way, from an aldehyde compound and a hydrazine compound (Example 2), the same reaction as in Example 1 was carried out except that 9-ethyl-3-carbazolecarboxaldehyde (F was used as the aldehyde compound), and 9-ethyl-3-carbazole Synthesize carboxaldehyde carbazole hydrazone (G).
実施領１と同様に２５０℃で９−エチル−３−カルバソ
ールカルボキシアルデヒドカルバゾールヒドラゾン（Ｇ
を、９−エチル−３−カルバゾールニトリル■とカルバ
ゾール正に熱分解し、カラム通過により９−エチル−３
−カルバソールニトリル■のみを単離する。このとき９
−エチル−３−（実施例３）
アルデヒド化合物としてペンズアルデヒ）’ （Ｉ）
ヲ用いた他は実施例、１と同様の反応を行い、ベンズア
ルデヒドカルバゾールヒドラゾン（Ｊ）を合成する。9-Ethyl-3-carbasolcarboxaldehydecarbazolehydrazone (G
is thermally decomposed with 9-ethyl-3-carbazole nitrile ■, and 9-ethyl-3 is produced by passing through a column.
- Isolate only carbazol nitrile ■. At this time 9
-Ethyl-3- (Example 3) Penzaldehy)' (I) as an aldehyde compound
Benzaldehyde carbazole hydrazone (J) was synthesized by carrying out the same reaction as in Example 1, except that 1 was used.
実施例１と同様に２５０℃でベンズアルデヒドカルバソ
ールヒドラゾン（Ｊ）ヲペンゾニトリル■とカルバゾー
ル（ト）に熱分解した後、ベンゾニトリル■のみを単離
する。このときベンゾニトリル■の収率は５５％である
。As in Example 1, benzaldehyde carbazole hydrazone (J) is thermally decomposed into penzonitrile (1) and carbazole (2) at 250°C, and then only benzonitrile (2) is isolated. At this time, the yield of benzonitrile ① was 55%.
σΩ 囚
（実施例４）
アルデヒド化合物としてｎ−ブチルアルデヒド（０を用
いた他は実施例１と同様の反応を行い、ｎ−ブチルアル
デヒドカルバゾールヒドラゾンＭを合成する。ｎ−ブチ
ルアルデヒドカルバゾールヒドラゾンＭを、実施例１と
同様に２５０℃で、ｎ−プチルニｌ−’ＪルＮとカルバ
ゾール（Ｅ）に熱分解した後、ｎ−ブチルニ） ＩＪル
ペのみを単離する。σΩ Prisoner (Example 4) The same reaction as in Example 1 was carried out except that n-butyraldehyde (0) was used as the aldehyde compound to synthesize n-butyraldehyde carbazole hydrazone M. After thermal decomposition at 250°C in the same manner as in Example 1 into n-butyl(N) and carbazole (E), only n-butyl(N)IJ(E) is isolated.
このときのｎ−ブチルニトリルＮの収率は５５％である
。The yield of n-butylnitrile N at this time was 55%.
（実施例５）
アルデヒド化合物としてｔｃｒｔ−ブチルアルデヒドΩ
を用いた他は実施例、１と同様の反応を行いｔｅｒｔ−
ブチルアルデヒドカルバゾールヒドラゾン（Ｐ）を合成
する。ｔｅｒｔ−ブチルアルデヒドカルバゾールヒドラ
ゾン（Ｐ）を実施例１と同様に２５０℃で熱分解し、ｔ
ｅｒｔ−ブチルニトリルｆＱ）とカルバゾール閃にした
後、ｔｅｒｔ−ブチルニトリル（Ｑのみを単離する。こ
のときのｔｅｒｔ−ブチルニ） ＩＪグリルＱの収率は
５０％である。(Example 5) tcrt-butyraldehyde Ω as an aldehyde compound
The reaction was carried out in the same manner as in Example 1 except that tert-
Synthesize butyraldehyde carbazole hydrazone (P). Tert-butyraldehyde carbazole hydrazone (P) was thermally decomposed at 250°C in the same manner as in Example 1, and t
After merging with tert-butylnitrile (fQ) and carbazole, only tert-butylnitrile (Q) is isolated.The yield of tert-butylnitrile (IJ grill Q) is 50%.
（実施例６）
アルデヒド化合物として１−ピレンアルデヒド（Ｒ１，
ヒドラジン化合物としてジフェニルヒドラジノ（Ｓｌを
用いた他は実施例Ｉと同様の反応を行い、ヒドラゾン化
合物として１−ピレンアルデヒドジフェニルヒドラゾン
ｍを合成する。■−ピレンアルデヒドジフェニルヒドラ
ゾン（′１１を３００°Ｃで実施例１と同様に熱分解し
、１−ピレンニトリル（財）とジフェニルアミン凹にし
た後、１−ピレンニトリルυのみを単離する。このとき
の１−ピレンニトリル（財）の収率は５３％である。(Example 6) 1-pyrenaldehyde (R1,
The same reaction as in Example I is carried out except that diphenylhydrazino (Sl) is used as the hydrazine compound, and 1-pyrenaldehyde diphenylhydrazone m is synthesized as a hydrazone compound. After thermal decomposition in the same manner as in Example 1 to form 1-pyrenenitrile (goods) and diphenylamine, only 1-pyrenenitrile υ is isolated.The yield of 1-pyrenenitrile (goods) at this time is It is 53%.
（実施例７）
アルデヒド化合物にｐ−ジエチルアミノサリチルアルデ
ヒドＷ、ヒドラジン化合物としてジフェニルヒドラジン
（Ｓ）を用いた他は実施例１と同様の反応を行い、ｐ−
ジエチルアミノサリチルアルデヒドジフェニルヒドラゾ
ン（３）を合成する。(Example 7) The same reaction as in Example 1 was carried out except that p-diethylaminosalicylaldehyde W was used as the aldehyde compound and diphenylhydrazine (S) was used as the hydrazine compound.
Diethylaminosalicylaldehyde diphenylhydrazone (3) is synthesized.
ｐ−ジエチルアミノサリチルアルデヒドジフェニルヒド
ラゾン閃を３００℃で実施例１と同様に熱分解し、４−
ジエチルアミノ−２−ヒドロキシベンゾニトリル閏とジ
フェニルアミン（ト）にした後、４−ジエチルアミノ−
２−ヒドロキシベンゾニトリル（１）のみを単離する。p-diethylaminosalicylaldehyde diphenylhydrazone was thermally decomposed at 300°C in the same manner as in Example 1, and 4-
After converting diethylamino-2-hydroxybenzonitrile to diphenylamine (2), 4-diethylamino-
Only 2-hydroxybenzonitrile (1) is isolated.
このときの４−ジエチルアミノ−２−ヒドロキシベンゾ
ニトリル（至）の収率〔発明の効果〕
本発明の実施により毒性の高い青酸塩を用いることなく
、毒性の低いアルデヒド化合物よりニトリル化合物を製
造することができる。Yield of 4-diethylamino-2-hydroxybenzonitrile (maximum) at this time [Effect of the invention] By carrying out the present invention, a nitrile compound can be produced from a less toxic aldehyde compound without using a highly toxic cyanide. Can be done.
また、加熱したカラムにヒドラゾン化合物を通過させる
だけでニトリル化合物の生成および単離ができ、容易に
ニトリル化合物を製造することができる。更にアルデヒ
ド化合物を選択することにより、種々のニトリル化合物
を製造することができる。Furthermore, a nitrile compound can be generated and isolated simply by passing a hydrazone compound through a heated column, making it possible to easily produce a nitrile compound. Furthermore, various nitrile compounds can be produced by selecting an aldehyde compound.
Claims (1)
反応せしめヒドラゾン化合物を合成した後、該ヒドラゾ
ン化合物を熱分解し、該熱分解により生成したニトリル
化合物と２級アミンを分離し、ニトリル化合物を単離す
ることを特徴とするニトリル化合物の製造方法。Synthesizing a hydrazone compound by reacting an aldehyde compound and a hydrazine compound in an acidic catalyst, then thermally decomposing the hydrazone compound, separating a nitrile compound and a secondary amine produced by the thermal decomposition, and isolating the nitrile compound. A method for producing a nitrile compound characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31682687A JPH01157922A (en) | 1987-12-15 | 1987-12-15 | Production of nitrile compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31682687A JPH01157922A (en) | 1987-12-15 | 1987-12-15 | Production of nitrile compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01157922A true JPH01157922A (en) | 1989-06-21 |
Family
ID=18081351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31682687A Pending JPH01157922A (en) | 1987-12-15 | 1987-12-15 | Production of nitrile compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01157922A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005035496A1 (en) * | 2003-10-03 | 2005-04-21 | Aventis Pharmaceuticals Inc. | Process for the preparation of n-amino substituted heterocyclic compounds |
-
1987
- 1987-12-15 JP JP31682687A patent/JPH01157922A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005035496A1 (en) * | 2003-10-03 | 2005-04-21 | Aventis Pharmaceuticals Inc. | Process for the preparation of n-amino substituted heterocyclic compounds |
| US7112682B2 (en) | 2003-10-03 | 2006-09-26 | Aventis Pharmaceuticals Inc. | Process for the preparation of N-amino substituted heterocyclic compounds |
| AU2004279808B2 (en) * | 2003-10-03 | 2010-04-22 | Aventis Pharmaceuticals Inc. | Process for the preparation of N-amino substituted heterocyclic compounds |
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