JPS62169752A - Production of lower alkoxyacylaminoaniline - Google Patents
Production of lower alkoxyacylaminoanilineInfo
- Publication number
- JPS62169752A JPS62169752A JP1078086A JP1078086A JPS62169752A JP S62169752 A JPS62169752 A JP S62169752A JP 1078086 A JP1078086 A JP 1078086A JP 1078086 A JP1078086 A JP 1078086A JP S62169752 A JPS62169752 A JP S62169752A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- lower alkoxy
- inorganic acid
- acid salt
- acylaminoaniline
- 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 10
- 235000002639 sodium chloride Nutrition 0.000 claims abstract description 29
- -1 inorganic acid salt Chemical class 0.000 claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims abstract description 5
- 235000019341 magnesium sulphate Nutrition 0.000 claims abstract description 5
- 239000011780 sodium chloride Substances 0.000 claims abstract description 5
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 3
- 239000003125 aqueous solvent Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000010446 mirabilite Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 9
- 239000006227 byproduct Substances 0.000 abstract description 8
- 239000013078 crystal Substances 0.000 abstract description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 5
- 238000005917 acylation reaction Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 230000008878 coupling Effects 0.000 abstract description 2
- 238000010168 coupling process Methods 0.000 abstract description 2
- 238000005859 coupling reaction Methods 0.000 abstract description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 abstract description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract description 2
- 235000011152 sodium sulphate Nutrition 0.000 abstract description 2
- 230000010933 acylation Effects 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 abstract 1
- SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical group COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 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
- 239000002244 precipitate Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は低級アルコキシアシルアミノアニリンの製法に
関するものであり、詳しくは、／−低級アルコキシーコ
、タージアミノベンゼンをアシル化剤でモノアシル化す
ることにょリコー低級アルコキシーｊ−アシルアミノア
ニリンを製造する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 method for producing lower alkoxyacylaminoaniline, and more specifically, involves monoacylating /-lower alkoxyco-terdiaminobenzene with an acylating agent. This invention relates to a method for producing Ricoh lower alkoxy j-acylaminoaniline.
（従来の技術）
低級アルコキシアシルアミノアニリン例えば、−一メト
キシー！−アシルアミノアニリンはそれ自体又はこれを
Ｎ−アルキル化したものは通常、モノアゾ染料のカップ
リング成分として広く用いられている。(Prior Art) Lower alkoxyacylaminoaniline, for example -1methoxy! -Acylaminoaniline itself or its N-alkylated product is generally widely used as a coupling component for monoazo dyes.
２−メトキシ−！−アシルアミノアニリンの製法として
は、いくつかの方法が知られており。2-Methoxy-! - Several methods are known for producing acylaminoaniline.
その一つとして例えば、 ２，４ｔ−ジアミノアニソー
ルをアシル化剤でモノアシル化する方法が知られている
。この反応は、通常、水溶媒中で簡単に実施することが
できる。For example, a method is known in which 2,4t-diaminoanisole is monoacylated with an acylating agent. This reaction can usually be easily carried out in an aqueous solvent.
しかしながら、この方法においては、目的とスルコーメ
トキシーｊ−アシルアミノアニリン以外に１例えば、ジ
アシル体などの副生物の生成が多く、そのため、目的生
成物の収率が低くなり経済的に好ましい方法とは言えな
がっ九。However, in this method, in addition to the desired product and sulcomethoxyj-acylaminoaniline, many by-products such as diacyls are produced, resulting in a low yield of the desired product, making it an economically preferable method. However, I can't say that.
（発明が解決しようとする問題点）
本発明は／−低級アルコキシ−２，クージアミノベンゼ
ンをアシル化剤によりモノアシル化してλ−低級アルコ
キシー！−アシルアミノアニリンを創造する際こと、ジ
アシル体などの副生物の生成を抑制し、高収率で２−低
級アルコキシ−オーフシルアミノアニリンを得る方法の
提供を目的とするものである。(Problems to be Solved by the Invention) The present invention monoacylates /-lower alkoxy-2,cudiaminobenzene with an acylating agent to form λ-lower alkoxy! The object of the present invention is to provide a method for obtaining 2-lower alkoxy-ofsylaminoaniline in high yield by suppressing the production of by-products such as diacyl compounds when creating -acylaminoaniline.
（問題点を解決するための手段）
すなわち１本発明は、／−低級アルコキシ−２、クージ
アミノベンゼンを水溶媒中でアシル化剤と反応させ一一
低級アルコキシー！−アシルアミノアニリンを製造する
方法において、無機酸塩を３〜２ｊ重量％（対全水分量
）溶解した反応溶媒中で実施することを特徴とする低級
アルコキシアシルアミノアニリンの製法を要旨とするも
のである。(Means for Solving the Problems) That is, 1. the present invention is to react 11-lower alkoxy-2, kudiaminobenzene with an acylating agent in an aqueous solvent. - A method for producing acylaminoaniline, the gist of which is a method for producing lower alkoxyacylaminoaniline, characterized in that the method is carried out in a reaction solvent in which 3 to 2J% by weight (relative to total water content) of an inorganic acid salt is dissolved. It is.
上記／−低低級アルコキシ−コグタージアミノベンゼン
しては、例えばコ、タージアミノアニソール、２．ター
ジアミノフエネトール等を挙げることができる。The above-mentioned /-lower alkoxy-cogterdiaminobenzenes include, for example, co-tertiary aminoanisole, 2. Terdiaminophenetol and the like can be mentioned.
上記アシル化剤としては１例えば、無水酢酸、無水プロ
ピオン酸などの酸無水物又は塩化ベンゾイルが挙げられ
る。そして、アシル化剤の使用量としては、通常、／−
低級アルコキシーコ。Examples of the above-mentioned acylating agent include acid anhydrides such as acetic anhydride and propionic anhydride, and benzoyl chloride. The amount of acylating agent used is usually /-
Lower alkoxyco.
グージアミノベンゼンに対して、７〜７．０！モル倍の
範囲が挙げられる。7 to 7.0 for goo diaminobenzene! A range of mole times is included.
上記水溶媒の使用量としては１通常、／−低級アルコキ
シ−２，クージアミノベンゼンに対してに〜２０重量倍
の範囲が挙げられる。The amount of the water solvent to be used is usually 1 to 20 times the weight of /-lower alkoxy-2,cudiaminobenzene.
本発明の反応は１通常、ＰＨ７〜りの範囲に調節して行
なうのが望ましく、ｐＨがあまり低い場合には、ジアシ
ル体の生成率が増加し、逆に、ｐＨがあまり高い場合に
はアシル化剤が分解し。The reaction of the present invention is usually carried out at a pH of 7 to 7. If the pH is too low, the production rate of diacyl forms will increase, whereas if the pH is too high, the acyl form will increase. The chemical agent decomposes.
好ましくない。Undesirable.
上記無機酸塩と【２ては食塩、芒硝、硫酸マグネシウム
、塩化カリウム、塩化カルシウム、硫酸カリウム、臭化
カリウム等が挙げられ、好ましくは食塩、芒硝及び硫酸
マグネシウムから選ばれた少なくとも一種の塩が挙げら
れる。そして、水溶媒中の無機酸塩の濃度としては％３
〜２５重量−の範囲が挙げられ、好ましくは！〜２０重
量係の範囲が挙げられる。また、水溶媒中の無機酸塩の
濃度が前記範囲よりも低い場合には、ジアシル体などの
副生物の生成を十分に抑制することができず、逆に、前
記範囲よりも高い場合には、原料の／−低級アルコキシ
−２゜クージアミノベンゼンが溶解し難くなり、アシル
化反応自体が良好に進行しないので好ましく表い。Examples of the above inorganic acid salts include common salt, mirabilite, magnesium sulfate, potassium chloride, calcium chloride, potassium sulfate, potassium bromide, etc., and preferably at least one salt selected from common salt, mirabilite and magnesium sulfate. Can be mentioned. And the concentration of inorganic acid salt in the water solvent is %3
~25wt-, preferably! -20 weight ratio is mentioned. Furthermore, if the concentration of the inorganic acid salt in the aqueous solvent is lower than the above range, the formation of by-products such as diacyls may not be sufficiently suppressed, and conversely, if it is higher than the above range, is preferable since the raw material /-lower alkoxy-2°cudiaminobenzene becomes difficult to dissolve and the acylation reaction itself does not proceed well.
本発明では水溶媒中の無機酸塩の濃度を上記の特定範囲
に調節しているため、反応開始時から終了時までの間１
反応で生成したコー低級プルコキシー！−アシルアミノ
アニリンが反応系内で塩析され、結晶として析出し、水
溶媒中に溶解しているコー低級アルコキシー！−アシル
アミノアニリンの量は極めて少ないため、一旦、生成し
た一一低級アルコキシー！−アシルアミノアニリンが更
にアシル化されてジアシル体となる可能性はφさいので
ある。In the present invention, since the concentration of the inorganic acid salt in the aqueous solvent is adjusted to the above-mentioned specific range, the period from the start to the end of the reaction is 1
Co-lower pulukoxy produced by reaction! -Acylaminoaniline is salted out in the reaction system, precipitated as crystals, and dissolved in the water solvent - lower alkoxy! -Since the amount of acylaminoaniline is extremely small, once it is formed, the lower alkoxy! -The possibility that acylaminoaniline is further acylated to form a diacyl is small.
なお、従来法においても、反応系内のｐＨを一定に保持
するために酸結合剤を供給しながら反応を実施する場合
には、無機酸塩が生成するが、この場合には反応前期に
おける無機酸塩の濃度が特に低いので、ジアシル体など
の副生物の生成を十分に抑制することができなかった。In addition, even in the conventional method, when the reaction is carried out while supplying an acid binder to keep the pH within the reaction system constant, inorganic acid salts are produced, but in this case, inorganic acid salts are produced in the early stage of the reaction. Since the concentration of the acid salt was particularly low, it was not possible to sufficiently suppress the production of by-products such as diacyls.
本発明の反応温度としては一／θ〜−２０℃の範囲を挙
げることができ、好ましくは−！〜！℃の範囲を誉げる
ことかできる。また、反応時、間としては７〜５時間の
範囲を挙げることができる。The reaction temperature of the present invention can be in the range of 1/θ to -20°C, preferably -! ~! You can admire the range of °C. Further, the reaction time can be in the range of 7 to 5 hours.
本発明の反応を実施するには、通常、上記無機酸塩を溶
解した水溶媒に原料／−−級アルコキシーＪ＜ｔ−ジア
ミノベンゼンを仕込み、攪拌下、これにアシル化剤を滴
下することにより行なわれる。To carry out the reaction of the present invention, the raw material/--class alkoxy J<t-diaminobenzene is usually added to an aqueous solvent in which the above-mentioned inorganic acid salt is dissolved, and the acylating agent is added dropwise thereto under stirring. It is done.
この反応においてはアシル化剤がカルボン酸を生成する
ため反応系内の−が低下するので、これを防止するため
に酸結合剤を用いて…を一定に保つ方法を採用すること
ができる。In this reaction, the acylating agent produces carboxylic acid, which lowers the - in the reaction system. To prevent this, an acid binding agent can be used to keep the - constant.
ここで用いる酸結合剤としては通常、苛性ソーダ又は炭
酸ソーダが挙げられる。The acid binder used here typically includes caustic soda or soda carbonate.
なお、この処理により無機酸塩を生成するので１通常、
反応援期はど無機酸塩の濃度は高くなる。Note that this treatment produces inorganic acid salts, so 1.
During the anti-support phase, the concentration of inorganic acid salts increases.
反応終了後の混合物中、生成物の殆んどが結晶として析
出しているが、必要に応じて溶解している目的生成物を
完全に塩析させるために。Most of the products are precipitated as crystals in the mixture after the reaction is completed, but if necessary, the dissolved target product may be completely salted out.
無機酸塩を更に添加する方法が採用される。なお１反応
終了時における混合物中の無機酸塩の濃度が例えば、７
０重量％以上、好ましくは７３重量％以上の場合には、
その必要性は少ない。この無機酸塩としては上述のもの
と同様に、例えば、食塩、芒硝、硫酸マグネシウムなど
が春
挙げらゲる。そして、この混合物を一過することにより
、λ−低級アルコキシー！−７シルアミノアニリンの結
晶を回収することができる。A method of further adding an inorganic acid salt is adopted. Note that the concentration of the inorganic acid salt in the mixture at the end of one reaction is, for example, 7
When it is 0% by weight or more, preferably 73% by weight or more,
There is little need for that. Examples of this inorganic acid salt include, as mentioned above, common salt, sodium sulfate, magnesium sulfate, and the like. By passing this mixture through, λ-lower alkoxy! -7 Cylaminoaniline crystals can be recovered.
（作用及び効果）
本発明によれば、特定濃度の無機酸塩を溶解する水溶媒
中で反応を実施するため、反応開始時から終了時までの
間に生成した２−低級アルコキシ−オーアシルアミノア
ニリンの大部分が結晶として析出するので％コー低級ア
ルコキシー！−アシルアミノアニリンが更にアシル化剤
と反応してジアシル体を副生ずる確率は少ない。(Functions and Effects) According to the present invention, since the reaction is carried out in an aqueous solvent in which a specific concentration of the inorganic acid salt is dissolved, the 2-lower alkoxy-oacylamino produced between the start of the reaction and the end of the reaction Since most of the aniline precipitates as crystals, % co-lower alkoxy! -The probability that the acylaminoaniline further reacts with the acylating agent to produce a diacyl by-product is low.
そのため、本発明ではジアシル体の副生が著しく少なく
、高収率で目的とする一一低級アルコキシー！−アシル
アミノアニリンを得ることができる。Therefore, in the present invention, the by-product of diacyl forms is significantly reduced, and the desired 1-1-lower alkoxy compound is produced in high yield! -Acylaminoaniline can be obtained.
（実施例）
次に１本発明を実施例により更に詳細に説明するが、本
発明は以下の実施例に限定されるものではない。(Example) Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to the following Examples.
実施例／〜！及び比較例／〜３
攪拌機及び温度調節器を有する。２／＝ガラス判反応器
に、２．タージアミノアニソール／θｏｆ（０，７２ｊ
モル）及び水≦／４ｔｆを仕込み、更に第１表に示す無
機酸塩を溶解した後、攪拌下。Example/~! and Comparative Examples/~3 Equipped with a stirrer and a temperature regulator. 2/=into the glass reactor, 2. Terdiaminoanisole/θof(0,72j
After dissolving the inorganic acid salts shown in Table 1, the mixture was stirred.
約θ℃にて無水酢酸２２．ｇｒ（０，７６１モル）と２
５チカ性ソーダ水浴液／ ２２ ｔ （０，７６１モル
）とを、各々グ時間かけて均等に滴下することにより反
応を行った。なお１反応開始時の系内の声は約ｔであり
、その後の−は７〜ワの範囲であり虎。Acetic anhydride at about θ°C22. gr (0,761 mol) and 2
The reaction was carried out by evenly dropping 22 t (0,761 mol) of a 5-potent soda water bath solution over a period of time. Note that the voice within the system at the beginning of one reaction is approximately t, and the subsequent - ranges from 7 to wa, which is a tiger.
反応終了後の生成物は殆んどが結晶として析出している
が、更に無機酸塩を力０えて水溶媒中の塩濃度をコＯ重
量係とじ九後、この混合物を炉別することにより、生成
物の結晶を回収した。After the reaction, most of the products are precipitated as crystals, but after removing the inorganic acid salt and adjusting the salt concentration in the water solvent by weight, the mixture is separated by furnace. , product crystals were collected.
このようにして回収した結晶を分析し、 ２，４を一ジ
アミノアニンールに対する！−アセテルアミノーコーメ
トキシアニリンの収率及び２，９ｔ−ジアセチルアミノ
アニソールの副生量を求め、第１表
出 願 人 三菱化成工業株式会社
代 理 人 弁理士 長谷用 −
（ほか１名）The crystals thus recovered were analyzed and 2,4 was compared to monodiaminoanyl! - Determine the yield of acetelaminoco-methoxyaniline and the amount of by-product of 2,9t-diacetylaminoanisole, and submit the results in Table 1. Applicant: Mitsubishi Chemical Industries, Ltd. Representative Patent Attorney Hase - (1 other person)
Claims (2)
を水溶媒中でアシル化剤と反応させ、２−低級アルコキ
シ−５−アシルアミノアニリンを製造する方法において
、無機酸塩を３〜２５重量％（対全水分量）溶解した反
応溶媒中で実施することを特徴とする低級アルコキシア
シルアミノアニリンの製法。(1) In a method for producing 2-lower alkoxy-5-acylaminoaniline by reacting 1-lower alkoxy-2,4-diaminobenzene with an acylating agent in an aqueous solvent, 3 to 25% by weight of an inorganic acid salt is % (relative to total water content) in a reaction solvent in which lower alkoxyacylaminoaniline is dissolved.
選ばれた少なくとも一種の塩であることを特徴とする特
許請求の範囲第１項記載の低級アルコキシアシルアミノ
アニリンの製法。(2) The method for producing lower alkoxyacylaminoaniline according to claim 1, wherein the inorganic acid salt is at least one salt selected from common salt, mirabilite, and magnesium sulfate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1078086A JPH0623147B2 (en) | 1986-01-21 | 1986-01-21 | Method for producing lower alkoxyacylaminoaniline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1078086A JPH0623147B2 (en) | 1986-01-21 | 1986-01-21 | Method for producing lower alkoxyacylaminoaniline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62169752A true JPS62169752A (en) | 1987-07-25 |
| JPH0623147B2 JPH0623147B2 (en) | 1994-03-30 |
Family
ID=11759847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1078086A Expired - Lifetime JPH0623147B2 (en) | 1986-01-21 | 1986-01-21 | Method for producing lower alkoxyacylaminoaniline |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0623147B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104003898A (en) * | 2014-06-05 | 2014-08-27 | 浙江洪翔化学工业有限公司 | Method for synthesizing o-methoxy-m-acetyl amino-N,N-diallyl phenylamine by utilizing 2,4-dinitrobenzene methyl ether |
-
1986
- 1986-01-21 JP JP1078086A patent/JPH0623147B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104003898A (en) * | 2014-06-05 | 2014-08-27 | 浙江洪翔化学工业有限公司 | Method for synthesizing o-methoxy-m-acetyl amino-N,N-diallyl phenylamine by utilizing 2,4-dinitrobenzene methyl ether |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0623147B2 (en) | 1994-03-30 |
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