JPS62184061A - Production of 3,3-bis-(4-dimethylaminophenyl)-6-dimethylaminophthalide - Google Patents
Production of 3,3-bis-(4-dimethylaminophenyl)-6-dimethylaminophthalideInfo
- Publication number
- JPS62184061A JPS62184061A JP61026615A JP2661586A JPS62184061A JP S62184061 A JPS62184061 A JP S62184061A JP 61026615 A JP61026615 A JP 61026615A JP 2661586 A JP2661586 A JP 2661586A JP S62184061 A JPS62184061 A JP S62184061A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- bis
- oxygen
- dimethylamino
- cobalt
- 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 9
- IPAJDLMMTVZVPP-UHFFFAOYSA-N Crystal violet lactone Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C=CC(=CC=2)N(C)C)C2=CC=C(N(C)C)C=C2C(=O)O1 IPAJDLMMTVZVPP-UHFFFAOYSA-N 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 7
- 239000011707 mineral Substances 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000010941 cobalt Substances 0.000 claims abstract description 4
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052802 copper Inorganic materials 0.000 claims abstract description 4
- 239000010949 copper Substances 0.000 claims abstract description 4
- 229910052742 iron Inorganic materials 0.000 claims abstract description 3
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 4
- 150000002697 manganese compounds Chemical class 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 230000001590 oxidative effect Effects 0.000 abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 2
- 239000002245 particle Substances 0.000 abstract description 2
- 239000004094 surface-active agent Substances 0.000 abstract description 2
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 abstract 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000011572 manganese Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 8
- 229910052720 vanadium Inorganic materials 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- -1 aromatic carboxylic acids Chemical class 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Furan Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
3.3−ビス−(4−ジメチルアミノフェニル)−6−
ジメチルアミノフタリドは、クリスタルノ(イオレット
ラクトン(以下c、v、TJと略称する)として公知で
ある。それ自体無色又はそれに近い色であるが電子受容
性物質、例えば有機酸酸性白土、フェノールホルマリン
樹脂、芳香族カルボン酸の金属塩、ビスフェノールA等
と緊密に接触させることによシ速やかに青紫色に発色す
る特性を有しておシ、感圧複写紙、感熱記録紙等の記録
材料用色素として最も広く使用されているものである。[Detailed description of the invention] [Industrial field of application] 3.3-bis-(4-dimethylaminophenyl)-6-
Dimethylaminophthalide is known as crystalno(iolet lactone (hereinafter abbreviated as c, v, TJ).It is colorless or nearly colorless in itself, but it contains electron-accepting substances such as organic acid clay, phenol. Recording materials such as pressure-sensitive copying paper, heat-sensitive recording paper, etc., which have the property of rapidly developing a blue-purple color when brought into close contact with formalin resin, metal salts of aromatic carboxylic acids, bisphenol A, etc. It is the most widely used coloring agent.
本発明はその改良された製造法に関するものである。The present invention relates to an improved method of manufacturing the same.
〔従来の技術と発明が解決しようとする問題点〕2−(
4,41−ビス−(ジメチルアミノ)−ベンゾヒドリル
〕−5−ジメチルアミノ安息香酸(以下LCと略称する
)を酸化してC,V、Lを合成する製造法としては数多
く知られているが、製造工程が煩雑であったシ、酸化に
よる分解副生成物が多く高収率で高品質のC!、V、L
を得ることは困難である。[Problems to be solved by conventional technology and invention] 2-(
There are many known production methods for synthesizing C, V, and L by oxidizing 4,41-bis-(dimethylamino)-benzohydryl]-5-dimethylaminobenzoic acid (hereinafter abbreviated as LC). The manufacturing process was complicated, and there were many decomposition byproducts due to oxidation, resulting in high yield and high quality C! ,V,L
is difficult to obtain.
例えば鉱酸水溶液中、過酸化鉛や過マンガン酸カリウム
で酸化する方法(米国特許第2417897号)、氷酢
酸、クロロホルム等の有機溶剤中、クロラニル、金属錯
体の存在下酸素酸化する方法(特開昭48−25750
号)及び酸触媒の存在下、非水溶性の炭化水素系溶剤と
水との混合液中過酸化水素で酸化する方法(%開開52
−78867号)等は、いずれもタール状副生成物が多
量生成し、O,V、Lの収率や品質が非常に悪く、又、
有機溶剤の回収など煩雑な工程が必要である。また、ア
ルカリ存在下に水溶液もしくは水溶性有機溶剤中過酸化
水素で酸化する方法(特開昭52−51584号)及び
アルカリ水溶液中コバルトや銅化合物の触媒存在下で過
酸化水素、酸素あるいは空気で酸化する方法(特公昭5
9−19548号)等は、いずれも反応生成物に未反応
物が多量包含されて塊状になるなど反応が進行しにくく
、C!、V、Lの収率や品質が悪い。For example, a method of oxidizing with lead peroxide or potassium permanganate in an aqueous mineral acid solution (US Pat. No. 2,417,897), a method of oxygen oxidation in the presence of chloranil or a metal complex in an organic solvent such as glacial acetic acid or chloroform (Japanese Patent Publication No. Showa 48-25750
No.) and a method of oxidizing with hydrogen peroxide in a mixture of a water-insoluble hydrocarbon solvent and water in the presence of an acid catalyst (% opening 52
-78867) etc., all of them produce a large amount of tar-like by-products, and the yield and quality of O, V, and L are very poor.
Complicated processes such as recovery of organic solvents are required. In addition, oxidation with hydrogen peroxide in an aqueous solution or water-soluble organic solvent in the presence of an alkali (Japanese Unexamined Patent Publication No. 52-51584) and hydrogen peroxide, oxygen or air in the presence of a cobalt or copper compound catalyst in an alkaline aqueous solution are also available. Method of oxidation (Tokuko Sho 5)
No. 9-19548), etc., the reaction is difficult to proceed as the reaction product contains a large amount of unreacted substances and becomes lumpy. , V, and L have poor yields and quality.
本発明は、上記の如く、C,V、L の合成に際し従
来の欠点を改良した新規な製造法を提供するものである
。As described above, the present invention provides a new manufacturing method that improves the conventional drawbacks in synthesizing C, V, and L.
本発明者等は、従来の酸化方法の欠点を改良すべく鋭意
研究した結果、本発明による改良された製造法によシ短
時間で高収率かつ高品質のc、v、Lが容易に得られる
ことを見い出し7た。すなわちLCを2.0−4.0の
Pl(価の鉱酸水溶液中、鉄、銅、コバルト及びマンガ
ン化合物から選ばれた1種以上の触媒存在下で空気、酸
素、又は酸素−空気混合物を用いて酸化することを特徴
とするC!、V、Lの製造法である。As a result of intensive research aimed at improving the shortcomings of conventional oxidation methods, the present inventors have found that c, v, and l can be easily produced in high yield and high quality in a short time using the improved production method of the present invention. I found 7 things that can be obtained. That is, the LC was prepared using air, oxygen, or an oxygen-air mixture in the presence of one or more catalysts selected from iron, copper, cobalt, and manganese compounds in an aqueous solution of a mineral acid with a valence of 2.0 to 4.0. This is a method for producing C!, V, and L, which is characterized by oxidizing using
本発明において触媒として使用する金属化合物の具体例
としては、塩化第二鉄、硫酸第1鉄、塩化第2銅、硫酸
鋼、酢酸銅、塩化コバルト、硫酸コバルト、酢酸コバル
ト、−化マンガン、硫酸マンガンなどがあげられ、鉱酸
としては塩酸、硫酸があげられる。本発明に用いられる
LCはできるだけ微細な状態、好ま・しくは10−20
ミクロン以下が有効でsb、酸化は40−100℃の
温度でおこなうのが有利で、空気、酸素又は酸素−空気
混合物は・微細な気泡として反応混合物中に導入するこ
とが望ましい。又反応混合物を均一に分散させるため活
面活性剤例えばポリオキシエチレン、アルキエーテル等
の添加が効果的である。Specific examples of metal compounds used as catalysts in the present invention include ferric chloride, ferrous sulfate, cupric chloride, steel sulfate, copper acetate, cobalt chloride, cobalt sulfate, cobalt acetate, manganese chloride, and sulfuric acid. Examples include manganese, and mineral acids include hydrochloric acid and sulfuric acid. The LC used in the present invention is as fine as possible, preferably 10-20
The oxidation is advantageously carried out at a temperature of 40 DEG -100 DEG C. and the air, oxygen or oxygen-air mixture is preferably introduced into the reaction mixture as fine bubbles. Further, in order to uniformly disperse the reaction mixture, it is effective to add an active surfactant such as polyoxyethylene or alkyether.
本発明の改良されたc、v、r、、の製造法が従来の酸
化法の欠点をなくし、短時間で高収率、高品質のC,v
、Lを合成する上において極めてすぐれていることを以
下に説明する。The improved method for producing c, v, r, , of the present invention eliminates the drawbacks of conventional oxidation methods, and produces high yield and high quality C, v in a short time.
, L will be explained below.
すなわち、本発明において、鉱酸水溶液好ましくは硫酸
水溶液はpH価2.0−4.0好ましくは2.0−3.
0においてc、v、Lをほとんど溶解せず、LC及びL
Cに含まれる不純物又は反応副生成物をよく溶解する。That is, in the present invention, the mineral acid aqueous solution, preferably the sulfuric acid aqueous solution, has a pH value of 2.0-4.0, preferably 2.0-3.
At 0, c, v, and L are hardly dissolved, and LC and L
Impurities or reaction by-products contained in C are well dissolved.
この結果酸化によシ生成したO、V、Lは反応系外にた
だち傾析出し、C,V、Lの生成が円滑におこなわれ高
い収率を得ることができる。As a result, O, V, and L produced by oxidation are immediately precipitated out of the reaction system, and C, V, and L are produced smoothly and a high yield can be obtained.
また、本発明の金属化合物からなる触媒、好ましくは銅
及びコバルト化合物は、高い触媒効果を示し、これら金
属化合物を用いない場合に比べ非常に反応を促進する。Further, the catalyst made of the metal compound of the present invention, preferably a copper and cobalt compound, exhibits a high catalytic effect and accelerates the reaction much more than when these metal compounds are not used.
これら金属化合物はいずれも水溶性で、1)、反応終了
後析出したC、V、Lを炉取、水洗するのみで、前述の
LC中の不純物や反応副生物とともにほとんど完全に除
去することができるため、高品質のC!、V、Lの製造
に極めて好都合である。All of these metal compounds are water-soluble, and 1) C, V, and L precipitated after the reaction can be removed almost completely by simply collecting them in a furnace and washing them with water, along with the impurities and reaction by-products in the LC mentioned above. High quality C! , V, and L.
次に実施例と比較例をあげて本発明を更に具体的に説明
する。Next, the present invention will be explained in more detail with reference to Examples and Comparative Examples.
実施例 1゜
工業用Lc 46.5 f (10〜20 ミクロン
以下の粒子径で純粋なLC41,79を含有する)に1
%硫酸水溶液250g、硫酸銅0.05り、スコアロー
ルφ100(花王アトラス社製)0.HFを加え、攪拌
下90′cに “て空気を1分間に100r:/の
割合で10時間で導入した。反応終了後、反応物を濾過
し、E過残渣を中性迄水洗して融点172−175℃の
乾燥粗生成物41.1 q (理論量の97%のC,V
、I、を含む)を得た。Example 1 1° Industrial Lc 46.5 f (contains pure LC41,79 with a particle size of 10 to 20 microns or less)
% sulfuric acid aqueous solution, 0.05 g of copper sulfate, score roll φ100 (manufactured by Kao Atlas Co., Ltd.) 0. HF was added, and air was introduced at a rate of 100 r/min for 10 hours at 90'C under stirring. After the reaction was completed, the reaction product was filtered, and the E filtered residue was washed with water until neutral, and the melting point was reduced. 41.1 q of dry crude product at 172-175°C (97% of theory C,V
, I) were obtained.
比較例
硫酸銅を加えない以外は、実施例1と全く同様に操作を
おこない、乾燥粗生成物37.5 F (理論量の12
%のC,v、Lを含む)を得た。Comparative Example The procedure was carried out in exactly the same manner as in Example 1, except that copper sulfate was not added.
% C, v, L) was obtained.
実施例 Z
実施例1における硫酸銅の代シに塩化コバルトの95.
6%のC0v、Lを含む)を得た。Example Z 95% of cobalt chloride was used instead of copper sulfate in Example 1.
6% C0v, containing L) was obtained.
実施例 3゜Example 3゜
Claims (1)
ベンゾヒドリル〕−5−ジメチルアミノ安息香酸を2.
0−4.0のPH価の鉱酸水溶液中、鉄、銅、コバルト
及びマンガン化合物から選ばれた1種以上の触媒存在下
で空気、酸素、又は酸素・空気混合物を用いて酸化する
ことを特徴とする3,3−ビス−(4−ジメチルアミノ
フェニル)−6−ジメチルアミノフタリドの製造法。(1) 2-[4,4^1-bis-(dimethylamino)-
Benzhydryl]-5-dimethylaminobenzoic acid 2.
Oxidation using air, oxygen, or an oxygen/air mixture in the presence of one or more catalysts selected from iron, copper, cobalt, and manganese compounds in an aqueous mineral acid solution with a pH value of 0 to 4.0. Characteristic method for producing 3,3-bis-(4-dimethylaminophenyl)-6-dimethylaminophthalide.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61026615A JPH0753828B2 (en) | 1986-02-07 | 1986-02-07 | Process for producing 3,3-bis- (4-dimethylaminophenyl) -6-dimethylaminophthalide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61026615A JPH0753828B2 (en) | 1986-02-07 | 1986-02-07 | Process for producing 3,3-bis- (4-dimethylaminophenyl) -6-dimethylaminophthalide |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62184061A true JPS62184061A (en) | 1987-08-12 |
JPH0753828B2 JPH0753828B2 (en) | 1995-06-07 |
Family
ID=12198388
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61026615A Expired - Fee Related JPH0753828B2 (en) | 1986-02-07 | 1986-02-07 | Process for producing 3,3-bis- (4-dimethylaminophenyl) -6-dimethylaminophthalide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0753828B2 (en) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50124931A (en) * | 1974-03-22 | 1975-10-01 | ||
JPS5277131A (en) * | 1975-12-20 | 1977-06-29 | Basf Ag | Process for producing lactone of triphenylmethane system |
JPS55120562A (en) * | 1979-02-14 | 1980-09-17 | Hodogaya Chem Co Ltd | Improved method of production of 3,3-bis-(4- dimethylaminophenyl)-6-dimethylaminophthalide |
-
1986
- 1986-02-07 JP JP61026615A patent/JPH0753828B2/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50124931A (en) * | 1974-03-22 | 1975-10-01 | ||
JPS5277131A (en) * | 1975-12-20 | 1977-06-29 | Basf Ag | Process for producing lactone of triphenylmethane system |
JPS55120562A (en) * | 1979-02-14 | 1980-09-17 | Hodogaya Chem Co Ltd | Improved method of production of 3,3-bis-(4- dimethylaminophenyl)-6-dimethylaminophthalide |
Also Published As
Publication number | Publication date |
---|---|
JPH0753828B2 (en) | 1995-06-07 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |