JPS62175444A - Production of 2,2'-dinitrodibenzyl - Google Patents
Production of 2,2'-dinitrodibenzylInfo
- Publication number
- JPS62175444A JPS62175444A JP61013769A JP1376986A JPS62175444A JP S62175444 A JPS62175444 A JP S62175444A JP 61013769 A JP61013769 A JP 61013769A JP 1376986 A JP1376986 A JP 1376986A JP S62175444 A JPS62175444 A JP S62175444A
- Authority
- JP
- Japan
- Prior art keywords
- nitrotoluene
- dinitrodibenzyl
- ethylate
- solvent
- reaction
- 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 7
- YBOZRPPSBVIHGJ-UHFFFAOYSA-N 1-nitro-2-[2-(2-nitrophenyl)ethyl]benzene Chemical group [O-][N+](=O)C1=CC=CC=C1CCC1=CC=CC=C1[N+]([O-])=O YBOZRPPSBVIHGJ-UHFFFAOYSA-N 0.000 title description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 9
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 claims abstract description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- -1 alkali metal ethylate Chemical class 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 11
- 239000007788 liquid Substances 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 2
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 235000012054 meals Nutrition 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 16
- 238000004817 gas chromatography Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 5
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- XKYICAQFSCFURC-UHFFFAOYSA-N isoamyl formate Chemical compound CC(C)CCOC=O XKYICAQFSCFURC-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- Catalysts (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２．２−ジニトロジベンジルの製造法に関する
。更に詳しくは０−ニトロトルエンを酸化する事による
２、２−ジニトロジベンジルの製造法に関する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a process for the production of 2,2-dinitrodibenzyl. More specifically, the present invention relates to a method for producing 2,2-dinitrodibenzyl by oxidizing 0-nitrotoluene.
従来の技術
２．２−ジニトロジベンジルは、医薬品、樹脂の中間体
として重要な化合物で、とりわけ中枢神経系に作用する
医薬品の中間体として重要度が高い。Prior Art 2.2-Dinitrodibenzyl is an important compound as an intermediate for pharmaceuticals and resins, and is particularly important as an intermediate for pharmaceuticals that act on the central nervous system.
２．２−ジニトロジベンジルの合成法としては従来より
種々の方法が提案されている。即ち
（］） シクロヘキサノン溶媒中、ｏ−ニトロトルエ
ンにギ酸イソアミル及びナトリウムエチラートを作用さ
せる方法〔ボーランド特許、１０５２３３］
（２） テトラヒドロフラン溶媒中、ｏ−ニトロトル
エンにカリウム了マイト及びアンモニアを作用させる方
法（Ｊ、 Ｏｒｇ−Ｃｈｅｍ、（４４）（３） エー
テル（溶媒） 中ｏ−ニトロトルエンにカリウム−１−
ブトキサイドと空気を作用させる方法（Ａｎｎ−Ｃｈｉ
ｍ−、（８） ｐ ３９１−５発明が解決しようとする
問題点
２．２−ジニトロジベンジルの製法として公知の前記し
たよ５な方法はそれぞれ欠点を有している。即ち
（１）の方法はギ酸イソアミルの様な高価な薬剤を多量
に消費する。０〜５℃といった低温下で２１時間もの長
時間反応することを要する、収率が約６０％と低い等の
欠点がある。Various methods have been proposed for the synthesis of 2.2-dinitrodibenzyl. That is, (]) A method in which o-nitrotoluene is reacted with isoamyl formate and sodium ethylate in a cyclohexanone solvent [Boland Patent, 105233] (2) A method in which potassium nitrite and ammonia are reacted with o-nitrotoluene in a tetrahydrofuran solvent (J , Org-Chem, (44) (3) Potassium-1- in o-nitrotoluene in ether (solvent)
Method of reacting butoxide with air (Ann-Chi
m-, (8) p 391-5 Problems to be Solved by the Invention 2. The above-mentioned five known methods for producing 2-dinitrodibenzyl each have drawbacks. That is, method (1) consumes a large amount of expensive chemicals such as isoamyl formate. It has drawbacks such as requiring a long reaction time of 21 hours at a low temperature of 0 to 5°C and a low yield of about 60%.
（２）の方法は取扱いの厄介なカリウムアマイドを使用
する上、０−ニトロトルエンを極めて低い濃度で反応し
なければならず、著しく設備生産性が悪く、工業的に有
利な製法とは云えない。Method (2) uses potassium amide, which is difficult to handle, and requires reacting 0-nitrotoluene at an extremely low concentration, resulting in extremely poor equipment productivity and cannot be said to be an industrially advantageous production method.
（３）の方法は、用いる溶媒の引火点が低（、その上通
気攪拌を行っていることから安全上の問題が大きい。又
カリウム−ｔ−ブトキサイドが高価な上、収率が（１）
法同様６０％と低（工業的に有利な製法とはいえない。Method (3) has a low flash point of the solvent used (in addition, it requires aeration and stirring, which poses a major safety problem. Also, potassium-t-butoxide is expensive, and the yield is low (1).
As with the method, it is low at 60% (it cannot be said to be an industrially advantageous manufacturing method).
このような理由から、安価な原料を用いて容易に、収率
よ＜２，２−ジニトロジベンジルを製造する方法の開発
が望まれている。For these reasons, it is desired to develop a method for easily producing 2,2-dinitrodibenzyl using inexpensive raw materials and with a lower yield.
問題点を解決する為の手段
本発明者は前記したような問題点を解決丁べ（鋭意研究
を重ねた結果、本発明を完成するに至った。即ち本発明
は、脂肪族炭化水素中アルカリ金属エチラートの存在下
に０−ニトロトルエンに分子状酸素及び／又は空気を作
用させる事を特徴とする２、２′−ジニトロジベンジル
の製造法を提供する。本発明の方法を詳細に説明する。Means for Solving the Problems The present inventor has completed the present invention as a result of intensive research to solve the above-mentioned problems. A method for producing 2,2'-dinitrodibenzyl is provided, which is characterized in that 0-nitrotoluene is reacted with molecular oxygen and/or air in the presence of a metal ethylate.The method of the present invention will be explained in detail.
本発明の方法においては脂肪族炭化水素が溶媒として用
いられる。脂肪族炭化水素としては一］Ｏ〜５０℃にお
いて液体であるものが好ましく殊に好ましいものは炭素
数７乃至】４の脂肪族炭化水素である。その使用量は０
−ニトロトルエンの２〜１５倍量好ましくは３〜１０倍
量（重量比）である。In the method of the invention aliphatic hydrocarbons are used as solvents. Preferred aliphatic hydrocarbons are those which are liquid at 10 to 50°C, and particularly preferred are aliphatic hydrocarbons having 7 to 4 carbon atoms. Its usage is 0
- 2 to 15 times the amount of nitrotoluene, preferably 3 to 10 times (weight ratio).
又アルカリ金属エチラートの具体例としてはナトリウム
エチラート、カリウムエチラート、リチウムエチラート
が挙げられその使用量は０−ニトロトルエンに対し５０
〜３００モル％、好ましくは１００〜２００モル％であ
る。Further, specific examples of alkali metal ethylate include sodium ethylate, potassium ethylate, and lithium ethylate, and the amount used is 50% per 0-nitrotoluene.
~300 mol%, preferably 100-200 mol%.
本発明においては分子状酸素又は空気が酸化剤として用
いられこれらは混合して用いることも出来る。工業的有
利性からは空気の使用が最も好ましい。これらの酸化剤
は通常の手段によって乾燥して使用するのが好ましい。In the present invention, molecular oxygen or air is used as an oxidizing agent, and these can also be used as a mixture. The use of air is most preferred from an industrial advantage. These oxidizing agents are preferably used after being dried by conventional means.
湿った酸化剤は反応液に存在するアルカリ金属エチラー
トを分解するばかりでな（反応速度の低下、収率の低下
を招（おそれがあるので好ましくない。分子状酸素又は
／及び空気の使用量は酸素換算で０−ニトロトルエンに
対し５０〜８００モル％、好ましくは１００〜５００モ
ル％であるが、反応液中の原料、生成物の量をガスクロ
マトグラフィーでチェックしながら所要量が決定される
。A wet oxidizing agent is undesirable because it not only decomposes the alkali metal ethylates present in the reaction solution, but also reduces the reaction rate and yield.The amount of molecular oxygen and/or air used is The amount is 50 to 800 mol %, preferably 100 to 500 mol %, based on 0-nitrotoluene in terms of oxygen, and the required amount is determined while checking the amounts of raw materials and products in the reaction solution by gas chromatography.
反応温度は通常−１０〜５０℃好ましくは０〜３０℃で
ある。反応温度が一１０℃より低くなると反応速度の低
下を来し又反応温度が５０℃を越すと副反応を伴い収率
の低下を米丁。The reaction temperature is usually -10 to 50°C, preferably 0 to 30°C. When the reaction temperature is lower than 110°C, the reaction rate decreases, and when the reaction temperature exceeds 50°C, side reactions occur and the yield decreases.
反応時間は反応温度、酸素及び／又は空気の導入速度に
よって変わり、ガスクロマトグラフィーによって反応液
中の原料の残量及びブー
目的物の生成物をチェックすることによって決められる
が通常は３〜１４時間である。The reaction time varies depending on the reaction temperature and the introduction rate of oxygen and/or air, and is determined by checking the remaining amount of raw materials in the reaction solution and the desired product by gas chromatography, but is usually 3 to 14 hours. It is.
反応が実質的に終了したなら反応液に水を加えアルカリ
金属エチラートを分解すると同時に反応を停止させ生成
した結晶を炉別して２゜２′−ジニトロジベンジルヲ得
ル。When the reaction is substantially completed, water is added to the reaction solution to decompose the alkali metal ethylate, the reaction is stopped at the same time, and the formed crystals are separated in a furnace to obtain 2.sup.2'-dinitrodibenzyl.
なお、ここで得られるろ液は未反応の０−二トロトルエ
ン以外副生物等をほとんど含有しない脂肪族炭化水素（
溶媒）である有機層とアルカリ金属水酸化物、エタノー
ル、着色性副生物等を含有する水層との二層から構成さ
れるものであるが、そのろ液を分液し、得られた有機層
を循環再使用する事が望ましい。The filtrate obtained here is an aliphatic hydrocarbon containing almost no byproducts other than unreacted 0-nitrotoluene.
It consists of two layers: an organic layer (solvent) and an aqueous layer containing alkali metal hydroxide, ethanol, coloring byproducts, etc. The filtrate is separated, and the resulting organic It is desirable to reuse the layers cyclically.
このような方法によって未反応の０−ニトロトルエンを
有効利用すると同時に、溶媒の回収等が省略できユーテ
ィリティー、用役費の節約がはかられ本発明の方法を工
業的に一層有利な方法とすることができる。By such a method, unreacted 0-nitrotoluene can be effectively utilized, and at the same time, recovery of the solvent can be omitted, saving utility and service costs, thereby making the method of the present invention even more industrially advantageous. I can do it.
なお、この際、得られる有機層は分液性が良好である為
はとんど脱水操作は必要ないが必要に応じて物理的、化
学的な方法で脱水（乾燥）処理を施してもよい。又分液
・脱水の各操作の際、損失した僅かの脂肪族炭化水素（
溶媒）を必要に応じ補充してもよい。At this time, since the organic layer obtained has good liquid separation properties, dehydration is not necessary at all, but dehydration (drying) may be performed by physical or chemical methods if necessary. . In addition, a small amount of aliphatic hydrocarbons (
(solvent) may be replenished as necessary.
こうして得られた２、２−ジニトロジベンジルは特に精
製手段を施す事なく医薬品、樹脂の原料として用いられ
るが必要なら再結晶等の精製手段で精製することもでき
る。The 2,2-dinitrodibenzyl thus obtained can be used as a raw material for pharmaceuticals and resins without any particular purification process, but if necessary, it can be purified by a purification process such as recrystallization.
実施例 本発明を実施例によって更に詳細に説明する。Example The present invention will be explained in more detail by way of examples.
実施例１゜
ｍ】、ナトリウムエチラート４５ｇを仕込み、氷水浴中
にて１０℃に冷却する。続いて０−二トロトルエン５５
．２ｇを加え、脱湿空気を２３０ ｍｌ ／ ｍｉｎ
の割合で導入しながら気−液が充分接触する様攪拌する
。この間反応温度は１０〜１５℃を保持する様水冷を行
う。空気を導入し始めてから約１時間程で結晶の析出が
始まり、反応は７時間で実質的に終了する。反応が終了
したら水２００ｍ１を加え、約３０分攪拌の後、炉別、
水洗すると淡褐色２゜２−ジニトロジベンジルが３９．
５ｇ得られた。Example 1 〖 followed by 0-nitrotoluene 55
．． Add 2g and dehumidify air at 230ml/min
While introducing the liquid at a ratio of 1, stir to ensure sufficient contact between gas and liquid. During this time, water cooling is performed to maintain the reaction temperature at 10 to 15°C. Precipitation of crystals begins about 1 hour after the introduction of air, and the reaction is substantially completed in 7 hours. When the reaction is complete, add 200ml of water, stir for about 30 minutes, and then separate the
When washed with water, 2°2-dinitrodibenzyl turns light brown.
5g was obtained.
これは理論収率の７２％に相当し、ガスクロマド・グラ
フィーによる純度は９８．０％であり融点は１２３〜１
２５℃であった。得られた炉液を静置後、分液すると２
４５ｍ１の有機層が得られ約１０ｇ相当の０−ニトロト
ルエンを含有していた。This corresponds to 72% of the theoretical yield, the purity by gas chromatography is 98.0%, and the melting point is 123-1.
The temperature was 25°C. After allowing the obtained furnace liquid to stand still, when the liquid is separated, 2
A 45 ml organic layer was obtained containing the equivalent of about 10 g of 0-nitrotoluene.
実施例２゜
実施例１において溶媒として実施例１でえられた反応液
のろ液を分液して見られたデカ１２２〜１２５℃）淡褐
色の２，２′−ジニトロジベンジルを得た。Example 2゜In Example 1, the filtrate of the reaction solution obtained in Example 1 was separated to give a light brown color of 2,2'-dinitrodibenzyl (122-125°C). .
これは理論収率の７３．５％に相当し、ガスクロマトグ
ラフィーによる純度は９７．８％であった。This corresponds to 73.5% of the theoretical yield, and the purity by gas chromatography was 97.8%.
実施例３゜
実施例１においてナトリウムエチラート４５ｇの代りに
カリウムエチラート４５ｇを用いる以外は実施例１と同
様な方法で反応をこれは理論収率の７４．８％に相当し
、ガスクロマトグラフィーによる純度は９８．３％であ
った。Example 3 The reaction was carried out in the same manner as in Example 1 except that 45 g of potassium ethylate was used instead of 45 g of sodium ethylate in Example 1. This corresponded to 74.8% of the theoretical yield, and gas chromatography The purity was 98.3%.
実施例４゜
て反応を実施したところ、４０．８ｇ（融点ニ相当し、
ガスクロマトグラフィーによる純度は９８．１％であっ
た。Example 4 When the reaction was carried out, 40.8 g (corresponding to the melting point)
Purity by gas chromatography was 98.1%.
実施例５゜
実施例１において脱湿空気の代りに乾燥した酸素ガスを
５０ ｍｌ ／ ｍｉｎの割合で導入する外は実施例１
と同様に反応を行うと、融点１２３．５〜１２５．５℃
ガスクロマトグラフィーＭ度９８．２％の２．２′−ジ
ニトロジペ７ シ／ｌ／ ｆ）：４０．６ｇ得られた。Example 5゜Example 1 except that dry oxygen gas was introduced at a rate of 50 ml/min instead of dehumidified air in Example 1.
When the reaction is carried out in the same manner as above, the melting point is 123.5-125.5℃.
Gas chromatography yielded 40.6 g of 2.2'-dinitrodipe (7c/l/f) with an M degree of 98.2%.
これは理論収率の７４％に相当する。This corresponds to 74% of the theoretical yield.
実施例６゜
実施例１において溶媒としてデカンの代りにｎ−オクタ
ン３５０ｍ１を用いる他は実施例１と同様に反応を実施
したところ、融点１２３．５〜１２６℃、ガスクロマト
グラフィー純度９８．５％の２．２′−ジニトロジベン
ジル３９．０ｇが得られた。これは理論収率７１．１％
に相当する。Example 6゜The reaction was carried out in the same manner as in Example 1 except that 350 ml of n-octane was used instead of decane as the solvent in Example 1. The melting point was 123.5-126°C, and the gas chromatography purity was 98.5%. 39.0 g of 2,2'-dinitrodibenzyl was obtained. This is a theoretical yield of 71.1%.
corresponds to
実施例７゜
実施例】において溶媒としてデカン２４０ｍ１の代りに
ドデカン３５０ ｍｌを用いる他は実施例１と同様に反
応を実施したところ、融点１２３〜１２５℃、ガスクロ
マトグラフィー純度９８．１％（７）２．２’−シニト
ロジペンジル３９．７ｇがえられた。これは理論収率７
２．４−％に相当する。Example 7 The reaction was carried out in the same manner as in Example 1 except that 350 ml of dodecane was used instead of 240 ml of decane as the solvent. ) 39.7 g of 2.2'-cinitrogipendyl was obtained. This is a theoretical yield of 7
It corresponds to 2.4-%.
発明の効果
０−ニトロトルエンヲｅ 化Ｌ テ、２．２−ジニトロ
ジベンジルを製造するにあたって安価な原料によって収
率よ（２，２’−ジニトロジベンジルを得ることができ
るようになった。Effects of the Invention In producing 0-nitrotoluene and 2,2-dinitrodibenzyl, it has become possible to obtain 2,2'-dinitrodibenzyl in a higher yield using inexpensive raw materials.
Claims (1)
下にｏ−ニトロトルエンに分子状酸素及び／又は空気を
作用させる事を特徴とする２，２−ジニトロジベンジル
の製造法(1) A method for producing 2,2-dinitrodibenzyl, which comprises reacting o-nitrotoluene with molecular oxygen and/or air in the presence of an alkali metal ethylate in an aliphatic hydrocarbon.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61013769A JPH0723346B2 (en) | 1986-01-27 | 1986-01-27 | Process for producing 2,2'-dinitrodibenzyl |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61013769A JPH0723346B2 (en) | 1986-01-27 | 1986-01-27 | Process for producing 2,2'-dinitrodibenzyl |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62175444A true JPS62175444A (en) | 1987-08-01 |
| JPH0723346B2 JPH0723346B2 (en) | 1995-03-15 |
Family
ID=11842456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61013769A Expired - Fee Related JPH0723346B2 (en) | 1986-01-27 | 1986-01-27 | Process for producing 2,2'-dinitrodibenzyl |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0723346B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105753709A (en) * | 2016-04-20 | 2016-07-13 | 安徽金鼎医药有限公司 | 2,2'-dinitrodibenzyl preparation method |
-
1986
- 1986-01-27 JP JP61013769A patent/JPH0723346B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105753709A (en) * | 2016-04-20 | 2016-07-13 | 安徽金鼎医药有限公司 | 2,2'-dinitrodibenzyl preparation method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0723346B2 (en) | 1995-03-15 |
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