JPH0713042B2 - 2,6-Dichloro-3,4-dinitroethylbenzene and process for producing the same - Google Patents
2,6-Dichloro-3,4-dinitroethylbenzene and process for producing the sameInfo
- Publication number
- JPH0713042B2 JPH0713042B2 JP61186836A JP18683686A JPH0713042B2 JP H0713042 B2 JPH0713042 B2 JP H0713042B2 JP 61186836 A JP61186836 A JP 61186836A JP 18683686 A JP18683686 A JP 18683686A JP H0713042 B2 JPH0713042 B2 JP H0713042B2
- Authority
- JP
- Japan
- Prior art keywords
- dichloro
- dinitroethylbenzene
- nitrophenol
- ethyl
- producing
- 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.)
- Expired - Fee Related
Links
- OAVYDLPOFVZNSK-UHFFFAOYSA-N 1-chloro-2-(2-chloroethyl)-4,5-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(CCCl)C=C1[N+]([O-])=O OAVYDLPOFVZNSK-UHFFFAOYSA-N 0.000 title claims description 13
- 238000000034 method Methods 0.000 title description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims description 5
- LBBUKWZHMPUPIF-UHFFFAOYSA-N 1,3-dichloro-5-(2-nitroethyl)benzene Chemical compound [O-][N+](=O)CCC1=CC(Cl)=CC(Cl)=C1 LBBUKWZHMPUPIF-UHFFFAOYSA-N 0.000 claims description 4
- 229910002651 NO3 Inorganic materials 0.000 claims description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 238000006396 nitration reaction Methods 0.000 claims description 3
- YTVCECQSAPGJBB-UHFFFAOYSA-N 2,4-dichloro-3-ethyl-6-nitrophenol Chemical compound CCC1=C(Cl)C=C([N+]([O-])=O)C(O)=C1Cl YTVCECQSAPGJBB-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RESTWAHJFMZUIZ-UHFFFAOYSA-N 1-ethyl-4-nitrobenzene Chemical compound CCC1=CC=C([N+]([O-])=O)C=C1 RESTWAHJFMZUIZ-UHFFFAOYSA-N 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- XAWCLWKTUKMCMO-UHFFFAOYSA-N 2-nitroethylbenzene Chemical compound [O-][N+](=O)CCC1=CC=CC=C1 XAWCLWKTUKMCMO-UHFFFAOYSA-N 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- PQSWCVYWEGIBPY-UHFFFAOYSA-N 2,2-dinitroethylbenzene Chemical compound [O-][N+](=O)C([N+]([O-])=O)CC1=CC=CC=C1 PQSWCVYWEGIBPY-UHFFFAOYSA-N 0.000 description 1
- -1 2,4-dichloro-3,4-dinitroethylbenzene Chemical compound 0.000 description 1
- SHTOXWILRLZXBP-UHFFFAOYSA-N 4-ethyl-1,2-dinitrobenzene Chemical compound CCC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1 SHTOXWILRLZXBP-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013076 target substance Substances 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は化成品及びその製法に関する。更に詳しくは2,
6−ジクロロ−3,4−ジニトロエチルベンゼン及びその製
法に関する。TECHNICAL FIELD The present invention relates to a chemical product and a method for producing the same. More details 2,
The present invention relates to 6-dichloro-3,4-dinitroethylbenzene and a method for producing the same.
従来の技術 2,6−ジクロロ−3,4−ジニトロエチルベンゼンは、新規
な化合物でありその製法あるいは2,6−ジクロロ−3,4−
ジニトロエチルベンゼンよりカラー写真用シアン発色剤
の中間体として有用な2,4−ジクロロ−３−エチル−６
−ニトロフエノールが得られる事も知られていない。2. Description of the Related Art 2,6-Dichloro-3,4-dinitroethylbenzene is a novel compound and its production method or 2,6-dichloro-3,4-
2,4-Dichloro-3-ethyl-6, which is more useful than dinitroethylbenzene as an intermediate for cyan color forming agents for color photography
-It is not known that nitrophenol can be obtained.
ところで2,4−ジクロロ−３−エチル−６−ニトロフエ
ノールの製法としては特開昭61−57536において次の方
法が提案されている。By the way, as a method for producing 2,4-dichloro-3-ethyl-6-nitrophenol, the following method has been proposed in JP-A-61-57536.
しかしながらこの方法ではｍ−エチルフエノールから誘
導される化合物（３）が高価である事、化合物（３）か
ら化合物（６）まで３段階の工程を要する事、さらには
化合物（３）から化合物（６）までの収率が71〜75％と
低い事等により2,4−ジクロロ−３−エチル−６−ニト
ロフエノールを安価に得る事が困難である。 However, in this method, the compound (3) derived from m-ethylphenol is expensive, three steps from compound (3) to compound (6) are required, and further, compound (3) to compound (6) It is difficult to obtain 2,4-dichloro-3-ethyl-6-nitrophenol at low cost because the yield up to () is as low as 71 to 75%.
発明が解決しようとする問題点 カラー写真用シアン発色剤の中間体として重要な2,4−
ジクロロ−３−エチル−６−ニトロフエノールを製造す
るために好都合な化合物が求められている。Problems to be Solved by the Invention 2,4- which is important as an intermediate for a cyan color former for color photography
There is a need for convenient compounds to prepare dichloro-3-ethyl-6-nitrophenol.
問題点を解決するための手段 本発明者らは、前記したような問題点を解決すべく鋭意
研究を重ねた結果、本発明に至ったものである。Means for Solving the Problems The inventors of the present invention have achieved the present invention as a result of earnest studies to solve the above problems.
即ち本発明は 式（１） で表される2,6−ジクロロ−3,4−ジニトロエチルベンゼ
ン及び、式（２） で表わされる2,6−ジクロロ−４−ニトロエチルベンゼ
ンを硫酸又はリン酸の存在下、硝酸又は硝酸塩を用いて
ニトロ化する事を特徴とする前記式（１）で表される2,
6−ジクロロ−3,4−ジニトロエチルベンゼンの製法を提
供する。That is, the present invention uses the formula (1) And 2,6-dichloro-3,4-dinitroethylbenzene represented by the formula (2) 2,6-dichloro-4-nitroethylbenzene represented by the formula (1) is nitrated with nitric acid or a nitrate in the presence of sulfuric acid or phosphoric acid.
A method for producing 6-dichloro-3,4-dinitroethylbenzene is provided.
本発明により得られる2,6−ジクロロ−3,4−ジニトロエ
チルベンゼンは、水溶液中または、水とメタノール、エ
タノール等の有機溶媒との混合液中、水酸化ナトリウム
または水酸化カリウム等のアルカリ金属で処理する事に
よってカラー写真用シアン発色剤の中間体として有用な
2,4−ジクロロ−３−エチル−６−ニトロフエノールを
高収率で得る事が出来る。The 2,6-dichloro-3,4-dinitroethylbenzene obtained by the present invention is an alkali metal such as sodium hydroxide or potassium hydroxide in an aqueous solution or a mixed solution of water and an organic solvent such as methanol or ethanol. By processing, it is useful as an intermediate of a cyan color developer for color photography.
2,4-Dichloro-3-ethyl-6-nitrophenol can be obtained in high yield.
本発明において原料として用いられる2,6−ジクロロ−
４−ニトロエチルベンゼンは、安価なｐ−ニトロエチル
ベンゼンのクロル化により容易に得られる。2,6-dichloro-used as a raw material in the present invention
4-Nitroethylbenzene is easily obtained by chlorination of inexpensive p-nitroethylbenzene.
本発明に従えば、安価な原料を用いて、簡略な工程でし
かも高収率で、2,4−ジクロロ−3,4−ジニトロエチルベ
ンゼンがえられるのでこれから容易に誘導される2,4−
ジクロロ−３−エチル−６−ニトロフエノールの入手が
極めて容易になる。According to the present invention, 2,4-dichloro-3,4-dinitroethylbenzene can be obtained with a simple process and a high yield by using an inexpensive raw material, so that it is easily derived from 2,4-
The availability of dichloro-3-ethyl-6-nitrophenol becomes extremely easy.
本発明の製法において、用いられる硫酸またはリン酸の
濃度は、50〜100％であり好ましくは70〜100％であり、
これらは三酸化イオウまたは無水リン酸を含んでいても
よい。又は前記したような濃度の硫酸とリン酸の混合物
であってもよい。またその使用量は2,6−ジクロロ−４
−ニトロエチルベンゼン１重量部に対し、好ましくは１
〜10重量部である。又用いられる硝酸または硝酸塩は1.
0〜1.1倍モルで充分で有り、過剰に用いても何の益もな
い。なおこのニトロ化の反応においてジクロルエタン、
ジクロルメタンのような不活性な有機溶媒を加えてもよ
い。硝酸塩の例としては硝酸ナトリウム、硝酸カリウム
等があげられる。反応温度は０〜150℃好ましくは50〜1
00℃であり、硝酸または硝酸塩は徐々に添加するのが好
ましく、ニトロ化の反応時間はこの添加に要する時間を
含め0.5〜10時間で充分である。In the production method of the present invention, the concentration of sulfuric acid or phosphoric acid used is 50 to 100%, preferably 70 to 100%,
These may include sulfur trioxide or phosphoric anhydride. Alternatively, it may be a mixture of sulfuric acid and phosphoric acid having the concentrations described above. The amount used is 2,6-dichloro-4.
-Per part by weight of nitroethylbenzene, preferably 1
~ 10 parts by weight. The nitric acid or nitrate used is 1.
A 0 to 1.1 times molar amount is sufficient, and there is no benefit in using it in excess. In this nitration reaction, dichloroethane,
An inert organic solvent such as dichloromethane may be added. Examples of nitrates include sodium nitrate and potassium nitrate. The reaction temperature is 0 to 150 ° C, preferably 50 to 1
The temperature is 00 ° C., and nitric acid or nitrate is preferably added gradually, and the reaction time for nitration is 0.5 to 10 hours including the time required for this addition.
反応が終ったなら反応液を常温まで冷却し例えば氷水あ
けして結晶をとり出してもよいし、70〜80℃より高い温
度で反応を行った場合は目的物がオイル状になるので液
−液分離をしてオイル層をとり出し、冷却して結晶化し
てもよい。After the reaction is completed, the reaction solution may be cooled to room temperature and then crystallized by, for example, pouring ice water, and if the reaction is carried out at a temperature higher than 70 to 80 ° C, the target product becomes an oily liquid. The liquid may be separated to take out the oil layer, and may be cooled for crystallization.
本発明の方法でえられた2,6−ジクロロ−3,4−ジニトロ
エチルベンゼンは十分に純度がたかいが所望ならメタノ
ール等の有機溶媒によって再結晶を行って更に純度をた
かめることもできる。なお目的物の純度はガスクロマト
グラフイーで容易に測定される。The 2,6-dichloro-3,4-dinitroethylbenzene obtained by the method of the present invention has a sufficiently high purity, but if desired, it can be recrystallized with an organic solvent such as methanol to further raise the purity. The purity of the target substance can be easily measured by gas chromatography.
本発明によって得られた2,6−ジクロロ−3,4−ジニトロ
エチルベンゼンから2,4−ジクロロ−３−エチル−６−
ニトロフエノールを合成するには次のような方法で行う
のが好都合である。加水分解において用いられるアルカ
リ剤の例としては水酸化ナトリウム、水酸化カリウム、
水酸化リチウム等があげられこれらは2,6−ジクロロ−
3,4−ジニトロエチルベンゼン１モルに対し２〜５モル
用いられる。溶媒としては水を用いるのが好都合である
がメタノール、エタノール、イソプロピルアルコール等
の有機溶媒と水との混合物を用いてもよい。反応温度は
通常50〜150℃であり反応時間は0.5〜10時間である。反
応が終了したなら反応液を硫酸、塩酸等によって中和し
2,4−ジクロロ−３−エチル−６−ニトロフエノールを
得る。2,4-Dichloro-3-ethyl-6-from 2,6-dichloro-3,4-dinitroethylbenzene obtained according to the present invention
To synthesize nitrophenol, the following method is convenient. Examples of alkaline agents used in hydrolysis include sodium hydroxide, potassium hydroxide,
Lithium hydroxide and the like are mentioned, and these are 2,6-dichloro-
It is used in an amount of 2 to 5 mol per mol of 3,4-dinitroethylbenzene. It is convenient to use water as the solvent, but a mixture of water with an organic solvent such as methanol, ethanol, or isopropyl alcohol may be used. The reaction temperature is usually 50 to 150 ° C., and the reaction time is 0.5 to 10 hours. When the reaction is complete, neutralize the reaction solution with sulfuric acid, hydrochloric acid, etc.
2,4-Dichloro-3-ethyl-6-nitrophenol is obtained.
2,4−ジクロロ−３−エチル−６−ニトロフエノールの
純度もガスクロマトグラフイーによって容易に測定され
本発明の2,6−ジクロロ−3,4−ジニトロエチルベンゼン
を使用して前記のように加水分解を行ってえた2,4−ジ
クロロ−３−エチル−６−ニトロフエノールの純度は写
真薬の原料として用いるに十分な純度を有している。The purity of 2,4-dichloro-3-ethyl-6-nitrophenol was also easily determined by gas chromatography and was hydrolyzed as described above using 2,6-dichloro-3,4-dinitroethylbenzene of the present invention. The purity of the 2,4-dichloro-3-ethyl-6-nitrophenol obtained by the above-mentioned procedure is sufficiently high to be used as a raw material for a photographic agent.
実施例 次に実施例をあげて本発明を更に詳しく説明するが、本
発明は以下の実施例に限定されるものではない。EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples.
実施例１ ｐ−ニトロエチルベンゼンをクロル化して得た2,6−ジ
クロロ−４−ニトロエチルベンゼン（b.p.139〜141℃/1
0mmHg）220gに濃硫酸600gを加え撹拌下70〜75℃で１時
間を要して98％硝酸68gを滴下した。更に30分、70〜75
℃で撹拌したあと10℃まで外冷し1kgの氷水にあけ
過、水洗、乾燥し、260gの淡黄色結晶を得た。この結晶
の元素分析値は次の通りで 元素分析 結 果 理論値 Ｃ 36.59％ 36.36％ Ｈ 2.17 2.27 Ｎ 10.61 10.61 Cl 26.25 26.52 2,6−ジクロロ−3,4−ジニトロエチルベンゼンである事
を確認した。このものはm.p.87−88℃を示し収率は98％
であった。（ガスクロ純度99.5％） 実施例２ 2,6−ジクロロ−４−ニトロエチルベンゼン220gに濃硫
酸800gを加え撹拌下60−70℃、２時間で硫酸カリウム11
5gを添加しさらに１時間、60−70℃にて撹拌した。反応
液を２の水へ滴下し析出した結晶を過・水洗・乾燥
し、258gの2,6−ジクロロ−3,4−ジニトロエチルベンゼ
ンを得た。Example 1 2,6-Dichloro-4-nitroethylbenzene obtained by chlorinating p-nitroethylbenzene (bp 139 to 141 ° C./1
600 g of concentrated sulfuric acid was added to 220 g of 0 mmHg) and 68 g of 98% nitric acid was added dropwise over 1 hour at 70 to 75 ° C. with stirring. 30 minutes, 70-75
After stirring at 0 ° C, the mixture was externally cooled to 10 ° C, poured into 1 kg of ice water, washed with water and dried to obtain 260 g of pale yellow crystals. The elemental analysis value of this crystal was as follows: Elemental analysis result Theoretical value C 36.59 % 36.36 % H 2.17 2.27 N 10.61 10.61 Cl 26.25 26.52 2,6-dichloro-3,4-dinitroethylbenzene was confirmed. This product shows mp87-88 ℃ and the yield is 98%.
Met. (Gas chromatographic purity 99.5%) Example 2 800 g of concentrated sulfuric acid was added to 220 g of 2,6-dichloro-4-nitroethylbenzene, and potassium sulfate was added at 60-70 ° C. for 2 hours with stirring.
5 g was added and the mixture was further stirred for 1 hour at 60-70 ° C. The reaction solution was added dropwise to 2 of water, and the precipitated crystals were washed with water, dried and dried to obtain 258 g of 2,6-dichloro-3,4-dinitroethylbenzene.
m.p.87−88℃ 収率 97％（ガスクロ純度99.6％） 参考例 実施例１で得られた、2,6−ジクロロ−3,4−ジニトロエ
チルベンゼン26.5gを28％水酸化ナトリウム水溶液50gに
加え還流下４時間反応させた。次いで室温まで冷却し希
塩酸で反応液を中和し、析出した結晶を過、水洗、乾
燥し、2,4−ジクロロ−３−エチル−６−ニトロフエノ
ール22.0gを得た。（収率93％） m.p. 46−47℃（文献値46.3−47.3℃） 元素分析 結果 理論値 Ｃ 41.07％ 40.85％ Ｈ 2.90 2.98 Ｎ 5.90 5.96 Cl 29.37 29.79 発明の効果 新規な化合物2,6−ジクロロ−3,4−ジニトロエチルベン
ゼン及びその製法が見出された。このものは容易に2,4
−ジクロロ−３−エチル−６−ニトロフエノールに導か
れるので2,4−ジクロロ−３−エチル−６−ニトロフエ
ノールの入手が容易になった。mp87-88 ° C Yield 97% (gas chromatographic purity 99.6%) Reference Example 26.5 g of 2,6-dichloro-3,4-dinitroethylbenzene obtained in Example 1 was added to 50 g of 28% sodium hydroxide aqueous solution under reflux. The reaction was carried out for 4 hours. Then, the mixture was cooled to room temperature and the reaction solution was neutralized with dilute hydrochloric acid, and the precipitated crystals were washed with water and dried to obtain 22.0 g of 2,4-dichloro-3-ethyl-6-nitrophenol. (Yield 93%) mp 46-47 ° C (literature value 46.3-47.3 ° C) Elemental analysis results Theoretical value C 41.07 % 40.85 % H 2.90 2.98 N 5.90 5.96 Cl 29.37 29.79 Effect of the invention Novel compound 2,6-dichloro- 3,4-Dinitroethylbenzene and its preparation have been found. This one is easily 2,4
Since it was led to -dichloro-3-ethyl-6-nitrophenol, 2,4-dichloro-3-ethyl-6-nitrophenol became easy to obtain.
Claims (2)
ン。1. A formula (1) 2,6-dichloro-3,4-dinitroethylbenzene represented by:
ンを硫酸又はリン酸の存在下，硝酸又は硝酸塩を用いて
ニトロ化する事を特徴とする 式（１） で表される2,6−ジクロロ−3,4−ジニトロエチルベンゼ
ンの製法。2. Formula (2) 2,6-dichloro-4-nitroethylbenzene represented by the formula (1) is characterized by nitration with nitric acid or a nitrate in the presence of sulfuric acid or phosphoric acid. A method for producing 2,6-dichloro-3,4-dinitroethylbenzene represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61186836A JPH0713042B2 (en) | 1986-08-11 | 1986-08-11 | 2,6-Dichloro-3,4-dinitroethylbenzene and process for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61186836A JPH0713042B2 (en) | 1986-08-11 | 1986-08-11 | 2,6-Dichloro-3,4-dinitroethylbenzene and process for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6344552A JPS6344552A (en) | 1988-02-25 |
| JPH0713042B2 true JPH0713042B2 (en) | 1995-02-15 |
Family
ID=16195478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61186836A Expired - Fee Related JPH0713042B2 (en) | 1986-08-11 | 1986-08-11 | 2,6-Dichloro-3,4-dinitroethylbenzene and process for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0713042B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5012015A (en) * | 1988-03-09 | 1991-04-30 | Daiei Chemical Co., Ltd. | Process for producing 2,4-dichloro-3-alkyl-6-nitrophenol |
| JPH02209055A (en) * | 1989-02-09 | 1990-08-20 | Toshiba Corp | Telephone set |
| US5136109A (en) * | 1990-08-28 | 1992-08-04 | Taoka Chemical Company, Ltd. | Process for preparing 2,4-dichloro-3-alkyl-6-nitrophenols |
-
1986
- 1986-08-11 JP JP61186836A patent/JPH0713042B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6344552A (en) | 1988-02-25 |
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