JPS6316378B2 - - Google Patents
Info
- Publication number
- JPS6316378B2 JPS6316378B2 JP4715784A JP4715784A JPS6316378B2 JP S6316378 B2 JPS6316378 B2 JP S6316378B2 JP 4715784 A JP4715784 A JP 4715784A JP 4715784 A JP4715784 A JP 4715784A JP S6316378 B2 JPS6316378 B2 JP S6316378B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- amino
- present
- aminoazobenzene
- activated carbon
- 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
Links
- -1 aminoazo compound Chemical class 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000004986 phenylenediamines Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- QPQKUYVSJWQSDY-CCEZHUSRSA-N 4-(phenylazo)aniline Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- KQZBSZUGKSCFBL-UHFFFAOYSA-N 2-phenyldiazenylaniline Chemical class NC1=CC=CC=C1N=NC1=CC=CC=C1 KQZBSZUGKSCFBL-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229960002089 ferrous chloride Drugs 0.000 description 3
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000565 sulfonamide group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BIHXHCRYYKTKQD-UHFFFAOYSA-N (benzyldiazenyl)-phenylmethanamine Chemical class NC(C1=CC=CC=C1)N=NCC1=CC=CC=C1 BIHXHCRYYKTKQD-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 description 1
- NUWUBARWSZYTKN-UHFFFAOYSA-N 2-[(2,3-dimethylphenyl)diazenyl]-3,4-dimethylaniline Chemical class CC1=CC=CC(N=NC=2C(=C(C)C=CC=2N)C)=C1C NUWUBARWSZYTKN-UHFFFAOYSA-N 0.000 description 1
- BBVUAJTZGSWJDD-UHFFFAOYSA-N 4-methyl-2-[(4-methylphenyl)diazenyl]aniline Chemical compound C1=CC(C)=CC=C1N=NC1=CC(C)=CC=C1N BBVUAJTZGSWJDD-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021575 Iron(II) bromide Inorganic materials 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940046149 ferrous bromide Drugs 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明はフエニレンジアミン類の製法に関す
る。更に詳しくは式(1)
（式(1)においてR1、R2は水素原子、アルキル基、
アルコキシ基又はハロゲン原子を表わす）
で表わされるアミノアゾ化合物をメタノール又は
エタノール中
ハロゲン化鉄及び
活性炭
の存在下ヒドラジンで還元することを特徴とする
式(2)
（式(2)においてR1、R2は前記と同じ意味を表わ
す）
で表わされるフエニレンジアミン類の製法に関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a process for producing phenylene diamines. For more details, use formula (1) (In formula (1), R 1 and R 2 are hydrogen atoms, alkyl groups,
Formula (2), which is characterized in that an aminoazo compound represented by (In formula (2), R 1 and R 2 have the same meanings as above.) The present invention relates to a method for producing phenylenediamines represented by the following formula.
アミノアゾベンゼン類をpd−ｃ、pt−ｃまた
はラネーニツケル触媒を用いて接触水素還元して
アミン類をえる事は公知である。しかし、接触還
元法では耐圧の反応装置（オートクレーブ）等を
必要とするため、経済的に有利な方法とは言い難
い。 It is known to obtain amines by catalytic hydrogen reduction of aminoazobenzenes using PD-C, PT-C or Raney Nickel catalysts. However, since the catalytic reduction method requires a pressure-resistant reaction device (autoclave), etc., it cannot be said to be an economically advantageous method.
また特公昭56−2062号ではアミノアゾ化合物を
水中または有機溶媒中アルカリ性において重金属
化合物を触媒としヒドラジンを作用させポリアミ
ノ化合物を得ているが、この方法はその実施例か
ら明らかなようにスルホン酸基、カルボン酸基ま
たはスルホンアミド基のように、アルカリ水溶液
またはアルコール類に溶け易くするような置換基
を持つアミノアゾ化合物に適用されるのみで有
り、後記の比較例からも明らかなように前記のよ
うな置換基を有していないアミノアゾ化合物の還
元にはこの方法の適用は困難である。 Furthermore, in Japanese Patent Publication No. 56-2062, a polyamino compound is obtained by reacting an aminoazo compound with hydrazine in water or an alkaline organic solvent using a heavy metal compound as a catalyst. It is only applied to aminoazo compounds that have a substituent such as a carboxylic acid group or a sulfonamide group that makes them easily soluble in aqueous alkaline solutions or alcohols, and as is clear from the comparative examples below, It is difficult to apply this method to the reduction of aminoazo compounds that do not have substituents.
本発明者らはスルホン酸基、カルボン酸基又は
スルホンアミド基を有さないアミノアゾ化合物類
の還元法について鋭意検討した結果、鉄化合物及
び活性炭の存在下ヒドラジンでアミノアゾ化合物
類を還元すると効率よくアゾ基が還元されジアミ
ン類が収率よくえられることを見出し本発明を完
成させた。本発明の方法は、従来の硫化物による
還元法や鉄粉還元法に見られるような廃棄物を副
生する事もなく、又水素による接触還元のような
耐圧反応容器を必要とせず工業的に有利な方法で
あり、又アルカリ水溶液又はアルコール類に十分
な溶解力を示さないアミノアゾ化合物頼の還元が
可能であり、前記した特公昭56−2062号の方法に
比べアルカリ剤を用いない点、又適用範囲が広い
点で全く相違する。 The present inventors have conducted intensive studies on methods for reducing aminoazo compounds that do not have a sulfonic acid group, a carboxylic acid group, or a sulfonamide group, and have found that reducing aminoazo compounds with hydrazine in the presence of an iron compound and activated carbon effectively reduces the azo The present invention was completed by discovering that diamines can be obtained in good yield by reducing the group. The method of the present invention does not produce waste as a by-product as seen in conventional reduction methods using sulfides or iron powder reduction methods, and does not require a pressure-resistant reaction vessel unlike catalytic reduction methods using hydrogen, making it industrially viable. It is an advantageous method for reducing aminoazo compounds that do not have sufficient dissolving power in alkaline aqueous solutions or alcohols, and does not use an alkaline agent compared to the method of Japanese Patent Publication No. 56-2062 mentioned above. They are also completely different in that they have a wide range of application.
本発明の方法を詳細に説明する。 The method of the present invention will be explained in detail.
本発明の方法においては塩化第１鉄、塩化第２
鉄、臭化第１鉄又は臭化第２鉄のようなハロゲン
化鉄が用いられ、その用いる量はアミノベンゼン
類１モルに対し0.01〜0.5モル、好ましくは0.02〜
0.1モルである。また用いられる活性炭は、アミ
ノアゾベンゼン類１モルに対し５〜100ｇ、好ま
しくは20〜100ｇである。また、アミノアゾベン
ゼン類の具体的な例としては４−アミノアゾベン
ゼン、２−アミノアゾベンゼン、アミノアゾトル
エン類、アミノアゾキシレン類、アミノ−ジエチ
ルアゾベンゼン類、アミノ−ヘキサメチルアゾベ
ンゼン類、アミノ−ジメトキシアゾベンゼン類、
アミノ−テトラメトキシアゾベンゼン類、アミノ
−ジエトキシアゾベンゼン類、アミノ−テトラエ
トキシアゾベンゼン類、アミノジクロロアゾベン
ゼン類、アミノジクロロアゾトルエン類、アミノ
ジメトキシアゾトルエン類等があげられる。これ
らのアミノアゾベンゼン類は例えば細田豊著「染
料化学」第655頁に記載のように大過剰のアニリ
ン類中、塩酸及び亜硝酸塩を作用させるか、又特
開昭54−66627に記載のようにメタノール中でア
ニリン類に塩酸及び亜硝酸塩を作用させることに
よつて得られる。 In the method of the present invention, ferrous chloride, ferric chloride,
Iron, iron halide such as ferrous bromide or ferric bromide is used, and the amount used is 0.01 to 0.5 mol, preferably 0.02 to 0.5 mol, per mol of aminobenzenes.
It is 0.1 mole. The amount of activated carbon used is 5 to 100 g, preferably 20 to 100 g, per mole of the aminoazobenzene. Specific examples of aminoazobenzenes include 4-aminoazobenzene, 2-aminoazobenzene, aminoazotoluenes, aminoazoxylenes, amino-diethylazobenzenes, amino-hexamethylazobenzenes, and amino-dimethoxyazobenzenes. ,
Examples include amino-tetramethoxyazobenzenes, amino-diethoxyazobenzenes, amino-tetraethoxyazobenzenes, aminodichloroazobenzenes, aminodichloroazotoluenes, aminodimethoxyazotoluenes, and the like. These aminoazobenzenes can be prepared, for example, by reacting hydrochloric acid and nitrite in a large excess of aniline, as described in Yutaka Hosoda's "Dye Chemistry," p. 655, or by reacting with hydrochloric acid and nitrite in a large excess of aniline, as described in JP-A No. 54-66627. Obtained by reacting anilines with hydrochloric acid and nitrite in methanol.
また本発明の方法における溶媒としてはメタノ
ール又はエタノールが用いられる。またそれらの
混合物であつても良い。 Furthermore, methanol or ethanol is used as the solvent in the method of the present invention. It may also be a mixture thereof.
反応温度は20〜200℃好ましくは50〜100℃で行
われる。 The reaction temperature is 20-200°C, preferably 50-100°C.
以下実施例をあげて説明するが、本発明はこれ
らのみに限定されるものではない。 The present invention will be described below with reference to Examples, but the present invention is not limited thereto.
実施例 １
メタノール500ｇ、４−アミノアゾベンゼン197
ｇ、活性炭30ｇ、塩化第一鉄５ｇ、60％ヒドラジ
ンヒドラート90ｇを加え、還流下５時間反応さ
せ、触媒を過分離後、溶媒を留去後蒸留しｐ−
フエニレンジアミン97ｇ（収率90％、GC純度
99.5％）を得た。なおアニリン88ｇを回収した。
（回収率95％）
実施例 ２
メタノール500ｇ、２−アミノ−５，4′−ジメ
チルアゾベンゼン225ｇ、活性炭30ｇ、塩化第二
鉄５ｇ、60％ヒドラジンヒドラート95ｇを加え、
以下実施例１と同様にして、４−メチル−ｏ−フ
エニレンジアミン111ｇ（収率91％）を得た。
（G.C純度99.7％）
実施例 ３
メタノール500ｇ、４−アミノ−２，５，2′，
5′−テトラメチルベンゼン253ｇ、活性炭30ｇ、
塩化第一鉄５ｇ、60％ヒドラジンヒドラート95ｇ
を加え、以下実施例１と同様にして２，５−ジメ
チル−ｐ−フエニレンジアミン129ｇ（収率95％）
を得た。（G.C純度99.6％）
実施例 ４
メタノール500ｇ、４−アミノアゾベンゼン197
ｇ、活性炭30ｇ、塩化第２鉄５ｇ、60％ヒドラジ
ンヒドラート90ｇを加え以下実施例１と同様にし
てｐ−フエニレンジアミン96ｇ（収率89％、G.C.
純度99.5％）を得た。Example 1 500 g of methanol, 197 g of 4-aminoazobenzene
g, activated carbon 30g, ferrous chloride 5g, and 60% hydrazine hydrate 90g were added and reacted under reflux for 5 hours. After over-separating the catalyst, the solvent was distilled off and then distilled to give p-
97g of phenylenediamine (yield 90%, GC purity
99.5%). Additionally, 88 g of aniline was recovered.
(Recovery rate 95%) Example 2 Add 500 g of methanol, 225 g of 2-amino-5,4'-dimethylazobenzene, 30 g of activated carbon, 5 g of ferric chloride, and 95 g of 60% hydrazine hydrate.
Thereafter, in the same manner as in Example 1, 111 g (yield: 91%) of 4-methyl-o-phenylenediamine was obtained.
(GC purity 99.7%) Example 3 500 g of methanol, 4-amino-2,5,2',
253g of 5'-tetramethylbenzene, 30g of activated carbon,
Ferrous chloride 5g, 60% hydrazine hydrate 95g
was added, and 129 g of 2,5-dimethyl-p-phenylenediamine (yield 95%) was prepared in the same manner as in Example 1.
I got it. (GC purity 99.6%) Example 4 500 g of methanol, 197 g of 4-aminoazobenzene
g, activated carbon 30g, ferric chloride 5g, and 60% hydrazine hydrate 90g were added and the following procedure was repeated in the same manner as in Example 1 to obtain 96g p-phenylenediamine (yield 89%, GC
Purity of 99.5%) was obtained.
比較例
特公昭56−2062の実施例１に従い４−アミノア
ゾベンゼン197ｇ、水1000ｇ及び苛性ソーダ60ｇ、
活性炭５ｇを加え60〜70℃に加熱した。次いで塩
化第二鉄８ｇを加えたのち10％ヒドラジン水溶液
320ｇを30分で加え同温度で２時間撹拌した。結
晶を過し乾燥して194ｇの４−アミノアゾベン
ゼンを回収した。Comparative Example According to Example 1 of Japanese Patent Publication No. 56-2062, 197 g of 4-aminoazobenzene, 1000 g of water and 60 g of caustic soda,
5 g of activated carbon was added and heated to 60-70°C. Next, 8g of ferric chloride was added, followed by a 10% hydrazine aqueous solution.
320 g was added over 30 minutes and stirred at the same temperature for 2 hours. The crystals were filtered and dried to recover 194 g of 4-aminoazobenzene.
Claims (1)
アルコキシ基又はハロゲン原子を表わす） で表わされるアミノアゾ化合物をメタノール又は
エタノール中 ハロゲン化鉄及び 活性炭 の存在下ヒドラジンで還元することを特徴とする
式(2) （式(2)においてR1、R2は前記と同じ意味を表わ
す） で表わされるフエニレンジアミン類の製法。[Claims] 1 Formula (1) (In formula (1), R 1 and R 2 are hydrogen atoms, alkyl groups,
Formula (2), which is characterized in that an aminoazo compound represented by (In formula (2), R 1 and R 2 have the same meanings as above.) A method for producing phenylenediamines represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4715784A JPS60193950A (en) | 1984-03-14 | 1984-03-14 | Production of phenylenediamine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4715784A JPS60193950A (en) | 1984-03-14 | 1984-03-14 | Production of phenylenediamine compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60193950A JPS60193950A (en) | 1985-10-02 |
| JPS6316378B2 true JPS6316378B2 (en) | 1988-04-08 |
Family
ID=12767248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4715784A Granted JPS60193950A (en) | 1984-03-14 | 1984-03-14 | Production of phenylenediamine compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60193950A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4206416A1 (en) * | 1992-02-29 | 1993-09-02 | Wella Ag | AGENTS FOR OXIDATIVE FAIRING OF HAIR AND NEW 5-HALOGEN-2,4-BIS (ALKYLAMINO) -1-ALKYL BENZOLE |
| DE4421397A1 (en) * | 1994-06-18 | 1995-12-21 | Wella Ag | Oxidative dye for hair and new 2-alkylamino-4-amino-1-alkylbenzenes |
-
1984
- 1984-03-14 JP JP4715784A patent/JPS60193950A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60193950A (en) | 1985-10-02 |
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