JP3045803B2 - Process for producing anthraquinone dicarboxylic anhydride - Google Patents
Process for producing anthraquinone dicarboxylic anhydrideInfo
- Publication number
- JP3045803B2 JP3045803B2 JP3096580A JP9658091A JP3045803B2 JP 3045803 B2 JP3045803 B2 JP 3045803B2 JP 3096580 A JP3096580 A JP 3096580A JP 9658091 A JP9658091 A JP 9658091A JP 3045803 B2 JP3045803 B2 JP 3045803B2
- Authority
- JP
- Japan
- Prior art keywords
- sulfuric acid
- dinitrile
- dicarboxylic anhydride
- formula
- anthraquinone
- 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
- 238000000034 method Methods 0.000 title claims description 12
- HTXWSYPMOXEWQV-UHFFFAOYSA-N naphtho[3,2-e][2]benzofuran-1,3,6,11-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C(C=C2)=C1C1=C2C(=O)OC1=O HTXWSYPMOXEWQV-UHFFFAOYSA-N 0.000 title description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 32
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- WONPUYDAAHCRKZ-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-dicarbonitrile Chemical compound C1=CC(C#N)=C(C#N)C2=C1C(=O)C1=CC=CC=C1C2=O WONPUYDAAHCRKZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 13
- -1 1-amino-4,5-dihydroxyanthraquinone-2,3-dinitrile Chemical compound 0.000 description 10
- 239000005457 ice water Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- MFVRNTLOEGHWAF-UHFFFAOYSA-N 1-amino-4-hydroxy-9,10-dioxoanthracene-2,3-dicarbonitrile Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(C#N)C(C#N)=C2N MFVRNTLOEGHWAF-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XZPHNGYVABZCEK-UHFFFAOYSA-N 1,4-dihydroxy-9,10-dioxoanthracene-2,3-dicarbonitrile Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(C#N)C(C#N)=C2O XZPHNGYVABZCEK-UHFFFAOYSA-N 0.000 description 2
- FUZYYLWVPAGQHG-UHFFFAOYSA-N 11-amino-4-hydroxynaphtho[2,3-f][2]benzofuran-1,3,5,10-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C1C(=O)OC(=O)C1=C2O FUZYYLWVPAGQHG-UHFFFAOYSA-N 0.000 description 2
- KHSQVAWUVKIOOT-UHFFFAOYSA-N O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1C(=O)OC(=O)C1=C2O Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1C(=O)OC(=O)C1=C2O KHSQVAWUVKIOOT-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- QUZJFTXRXJQLBH-UHFFFAOYSA-N 1,4-diamino-9,10-dioxoanthracene-2,3-dicarbonitrile Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(C#N)C(C#N)=C2N QUZJFTXRXJQLBH-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Landscapes
- Furan Compounds (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、色素の中間体であるア
ントラキノンジカルボン酸無水物の製造法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a process for producing an anthraquinone dicarboxylic anhydride which is an intermediate of a dye.
【０００２】[0002]
【従来の技術】アントラキノンジカルボン酸無水物は分
散染料、近赤外線吸収剤、カラー液晶用２色性色素、偏
光板用色素等に用いられるアントラキノン系色素の製造
に用いられる中間体として重要な化合物である。2. Description of the Related Art Anthraquinone dicarboxylic anhydride is an important compound as an intermediate used in the production of anthraquinone dyes used in disperse dyes, near-infrared absorbers, dichroic dyes for color liquid crystals, dyes for polarizing plates, and the like. is there.
【０００３】従来、アントラキノンジカルボン酸無水物
の製造方法として、１，４−ジアミノ−２，３−ジシア
ノアントラキノンを加水分解する下記式（Ａ）（化３）
の方法が「ザ ケミストリー オブ シンセティク ダ
イズ（Ｔｈｅ Ｃｈｅｍｉｓｔｒｙ ｏｆ Ｓｙｎｔｈ
ｅｔｉｃ Ｄｙｅｓ．）Ｖｏｌｕｍｅ III」Ｋ．Ｖｅｎ
ｋａｔａｒａｍａｎ著；Ａｃａｄｅｍｉｃ Ｐｒｅｓｓ
刊の４１４項に記載されている。Heretofore, as a method for producing anthraquinone dicarboxylic anhydride, there has been proposed the following formula (A) wherein 1,4-diamino-2,3-dicyanoanthraquinone is hydrolyzed.
Method of "The Chemistry of Synthic Soybean (The Chemistry of Synth
etic Dyes. ) Volume III "K. Ven
by Kataraman; Academic Press
It is described in section 414 of the book.
【０００４】[0004]
【化３】 しかしながら、式（Ａ）の方法は多工程数を要し、又副
反応として下記式（Ｂ）（化４）の反応が起こり、Embedded image However, the method of the formula (A) requires a large number of steps, and the reaction of the following formula (B) (Formula 4) occurs as a side reaction,
【０００５】[0005]
【化４】 酸無水物（ａ）中に、イミド（ｂ）が必ず共存し純度が
低いという欠点があった。又、上記のイミド（ｂ）を除
く方法として特開平２−３６８３号にカルボン酸無水物
の精製法が開示されているが、工程数が多伎にわたり、
工業的に利用する一般的合成法としては問題があった。
そのため高收率で簡便な新しい製造法を検討する必要が
あった。Embedded image There is a disadvantage that the imide (b) always coexists in the acid anhydride (a) and the purity is low. As a method for removing the imide (b), a method for purifying a carboxylic anhydride is disclosed in JP-A-2-3683, but the number of steps is large.
There is a problem as a general synthetic method used industrially.
Therefore, it was necessary to consider a new and simple production method with high yield.
【０００６】[0006]
【発明が解決しようとする課題】本発明の目的は、アン
トラキノンジカルボン酸無水物をより簡便な方法で、し
かも高収率、高純度で製造する方法を提供することであ
る。SUMMARY OF THE INVENTION An object of the present invention is to provide a method for producing anthraquinone dicarboxylic anhydride in a simpler method, with a high yield and high purity.
【０００７】[0007]
【課題を解決するための手段】本発明者らは前記課題を
解決するために鋭意検討した結果、本発明を達成したも
のである。即ち、本発明の方法は、下記一般式（Ｉ）
（化５）Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, have achieved the present invention. That is, the method of the present invention comprises the following general formula (I)
(Formula 5)
【０００８】[0008]
【化５】 （式中、Ｒ1 は水素原子、アミノ基および水酸基を表わ
し、Ｒ2は水素原子、アミノ基、水酸基、およびハロゲ
ン原子を表わし、但し、ｎが２以上の場合はＲ2 は互い
に等しくても異なっていても良い。ｎは１〜４の整数を
表わす。）で示されるアントラキノンジニトリルを、濃
度６０〜１００％の硫酸中、５０〜２００℃で処理する
ことを特徴とする下記一般式（ＩＩ）（化６）Embedded image (In the formula, R 1 represents a hydrogen atom, an amino group and a hydroxyl group, R 2 represents a hydrogen atom, an amino group, a hydroxyl group, and a halogen atom, provided that when n is 2 or more even R 2 are equal to each other An anthraquinone dinitrile represented by the following general formula (n) is treated at 50 to 200 ° C. in sulfuric acid having a concentration of 60 to 100%, wherein n is an integer of 1 to 4. II) (Chemical formula 6)
【０００９】[0009]
【化６】 （式中、Ｒ1 は水素原子、アミノ基および水酸基を表わ
し、Ｒ2は水素原子、アミノ基、水酸基、およびハロゲ
ン原子を表わし、但し、ｎが２以上の場合はＲ2 は互い
に等しくても異なっていても良い。ｎは１〜４の整数を
表わす。）で示されるアントラキノンジカルボン酸無水
物を高收率、高純度で得られる事を見出した。Embedded image (In the formula, R 1 represents a hydrogen atom, an amino group and a hydroxyl group, R 2 represents a hydrogen atom, an amino group, a hydroxyl group and a halogen atom, provided that when n is 2 or more, R 2 may be equal to each other. May be different. N represents an integer of 1 to 4.) Anthraquinone dicarboxylic anhydride represented by the formula (1) is obtained with high yield and high purity.
【００１０】本発明の製造方法で用いられる一般式
（Ｉ）で示されるアントラキノンジニトリルとしは、具
体的には、１，４−ジヒドロキシアントラキノン−２，
３−ジニトリル、１−アミノ−４−ヒドロキシアントラ
キノン−２，３−ジニトリル、１−アミノ−４，５−ジ
ヒドロキシアントラキノン−２，３−ジニトリル、１−
アミノ−４，５，８−トリヒドロキシアントラキノン−
２，３−ジニトリル、４−ヒドロキシ−１，５，８−ト
リアミノアントラキノン−２，３−ジニトリル、１−ア
ミノ−４，８−ジヒドロキシアントラキノン−２，３−
ジニトリル、１，５−ジアミノ−４，８−ジヒドロキシ
アントラキノン−２，３−ジニトリル、１，８−ジアミ
ノ−４，５−ジヒドロキシアントラキノン−２，３−ジ
ニトリル等が挙げられる。The anthraquinone dinitrile represented by the general formula (I) used in the production method of the present invention is, specifically, 1,4-dihydroxyanthraquinone-2,
3-dinitrile, 1-amino-4-hydroxyanthraquinone-2,3-dinitrile, 1-amino-4,5-dihydroxyanthraquinone-2,3-dinitrile, 1-
Amino-4,5,8-trihydroxyanthraquinone-
2,3-dinitrile, 4-hydroxy-1,5,8-triaminoanthraquinone-2,3-dinitrile, 1-amino-4,8-dihydroxyanthraquinone-2,3-
Examples thereof include dinitrile, 1,5-diamino-4,8-dihydroxyanthraquinone-2,3-dinitrile, and 1,8-diamino-4,5-dihydroxyanthraquinone-2,3-dinitrile.
【００１１】本発明で使用する硫酸の濃度は６０〜１０
０％の範囲であり、好ましくは８０〜９５％が良い。６
０％以下の硫酸濃度では、一般式（Ｉ）の化合物の硫酸
に対する溶解度が不足し反応が進行しない。The concentration of sulfuric acid used in the present invention is 60 to 10
It is in the range of 0%, preferably 80 to 95%. 6
At a sulfuric acid concentration of 0% or less, the solubility of the compound of the general formula (I) in sulfuric acid is insufficient and the reaction does not proceed.
【００１２】硫酸の使用量は、原料である一般式（Ｉ）
の化合物の３〜５０倍重量であり、好ましくは５〜２０
倍重量が良い。３倍未満の場合では反応が完結せず、低
純度の一般式（ＩＩ）の化合物が得られるのみである。
尚、５０倍を超える硫酸を使用しても特に問題はない
が、無闇に多量を使用することは反応器の容積効率を低
下させるのみであり、３〜５０倍重量の硫酸を使用した
場合と比較して特に効果は見られない。The amount of sulfuric acid used is determined by the general formula (I)
3 to 50 times the weight of the compound of the present invention, preferably 5 to 20 times.
Double weight is good. If the amount is less than 3 times, the reaction is not completed and only the compound of the general formula (II) having low purity is obtained.
In addition, although there is no particular problem even if sulfuric acid more than 50 times is used, the use of a large amount in the dark only lowers the volumetric efficiency of the reactor, and the case where sulfuric acid of 3 to 50 times weight is used. No particular effect is seen in comparison.
【００１３】反応温度は５０〜２００℃の範囲であり、
好ましくは１１０〜１４０℃の範囲が良い。５０℃未満
の温度では反応が進行せず、一方、２００℃を超える温
度では不純物が生成し純度が低下する。又、反応時間は
１〜２０時間の範囲であり、好ましくは３〜１０時間程
度である。The reaction temperature ranges from 50 to 200 ° C.,
Preferably, the range of 110 to 140 ° C. is good. At a temperature lower than 50 ° C., the reaction does not proceed, while at a temperature higher than 200 ° C., impurities are generated and the purity is lowered. The reaction time is in the range of 1 to 20 hours, preferably about 3 to 10 hours.
【００１４】以上のように反応させた後、反応液を室温
まで冷却した後、氷水に排出し、濾過洗浄、乾燥するこ
とにより高収率、高純度で一般式（ＩＩ）で表わされる
アントラキノンジカルボン酸無水物を得ることができ
る。After the reaction as described above, the reaction solution is cooled to room temperature, discharged into ice water, filtered, washed and dried to obtain a high yield, high purity anthraquinone dicarbonate represented by the general formula (II). An acid anhydride can be obtained.
【００１５】[0015]
【実施例】以下、本発明を実施例により更に詳細に説明
する。 実施例１ ６０％の硫酸１００ｇに１，４−ジヒドロキシアントラ
キノン−２，３−ジニトリル１０ｇを室温で装入し、１
００℃で５時間加熱攪拌した。反応液を室温まで冷却し
た後、氷水２００ｇに排出し、濾過、水洗した後、乾燥
し、１，４−ジヒドロキシアントラキノン−２，３−ジ
カルボン酸無水物１０．１ｇを得た。収率９４．４％、
液体クロマトグラフにより純度は９２％であった。The present invention will be described in more detail with reference to the following examples. Example 1 100 g of 60% sulfuric acid was charged with 10 g of 1,4-dihydroxyanthraquinone-2,3-dinitrile at room temperature.
The mixture was heated and stirred at 00 ° C for 5 hours. After the reaction solution was cooled to room temperature, it was discharged into 200 g of ice water, filtered, washed with water, and dried to obtain 10.1 g of 1,4-dihydroxyanthraquinone-2,3-dicarboxylic anhydride. 94.4% yield,
The purity by liquid chromatography was 92%.
【００１６】実施例２ ８０％の硫酸１００ｇに１−アミノ−４−ヒドロキシア
ントラキノン−２，３−ジニトリル１０ｇを室温で装入
し、１２０℃で５時間加熱攪拌した。反応液を室温まで
冷却した後、氷水３００ｇに排出し、濾過、水洗した
後、乾燥し、１−アミノ−４−ヒドロキシアントラキノ
ン−２，３−ジカルボン酸無水物１０.0ｇを得た。収率
９３．５％、純度９５％であった。Example 2 10 g of 1-amino-4-hydroxyanthraquinone-2,3-dinitrile was added to 100 g of 80% sulfuric acid at room temperature, and the mixture was heated and stirred at 120 ° C. for 5 hours. After the reaction solution was cooled to room temperature, it was discharged into 300 g of ice water, filtered, washed with water, and dried to obtain 10.0 g of 1-amino-4-hydroxyanthraquinone-2,3-dicarboxylic anhydride. The yield was 93.5% and the purity was 95%.
【００１７】実施例３ ９０％の硫酸１００ｇに１−アミノ−４−ヒドロキシア
ントラキノン−２，３−ジニトリル１０ｇを室温で装入
し、１３０℃で３時間加熱攪拌した。反応液を室温まで
冷却した後、氷水３５０ｇに排出し、濾過、水洗した
後、乾燥し、１−アミノ−４−ヒドロキシアントラキノ
ン−２，３−ジカルボン酸無水物１０．１ｇを得た。收
率９４．５％、純度９８％であった。Example 3 10 g of 1-amino-4-hydroxyanthraquinone-2,3-dinitrile was charged into 100 g of 90% sulfuric acid at room temperature, and the mixture was heated and stirred at 130 ° C. for 3 hours. After the reaction solution was cooled to room temperature, it was discharged into 350 g of ice water, filtered, washed with water, and dried to obtain 10.1 g of 1-amino-4-hydroxyanthraquinone-2,3-dicarboxylic anhydride. The yield was 94.5% and the purity was 98%.
【００１８】実施例４ ９５％の硫酸１００ｇに１，５−ジアミノ−４，８−ジ
ヒドロキシアントラキノン−２，３−ジニトリル１０ｇ
を室温で装入し、１５０℃で２時間加熱攪拌した。反応
液を室温まで冷却した後、氷水３７５ｇに排出し、濾
過、水洗した後、乾燥し、１，５−ジアミノ−４，８−
ジヒドロキシアントラキノン−２，３−ジカルボン酸無
水物９．８ｇを得た。収率９２．５％、純度９３％であ
った。Example 4 10 g of 1,5-diamino-4,8-dihydroxyanthraquinone-2,3-dinitrile in 100 g of 95% sulfuric acid
Was added at room temperature, and heated and stirred at 150 ° C. for 2 hours. After the reaction solution was cooled to room temperature, it was discharged into 375 g of ice water, filtered, washed with water, dried, and 1,5-diamino-4,8-.
9.8 g of dihydroxyanthraquinone-2,3-dicarboxylic anhydride were obtained. The yield was 92.5% and the purity was 93%.
【００１９】実施例５ １００％の硫酸１００ｇに１−アミノ−４，５，８−ト
リヒドロキシアントラキノン−２，３−ジニトリルを室
温で装入し、６０℃で８時間加熱攪拌した。反応液を室
温まで冷却した後、氷水４００ｇに排出し、濾過、水洗
した後、乾燥し、１−アミノ−４，５，８−トリヒドロ
キシアントラキノン−２，３−ジカルボン酸無水物１
０．１ｇを得た。収率９５．３％、純度９１％であっ
た。Example 5 1-Amino-4,5,8-trihydroxyanthraquinone-2,3-dinitrile was charged to 100 g of 100% sulfuric acid at room temperature, and heated and stirred at 60 ° C. for 8 hours. After the reaction solution was cooled to room temperature, it was discharged into 400 g of ice water, filtered, washed with water, dried, and dried with 1-amino-4,5,8-trihydroxyanthraquinone-2,3-dicarboxylic anhydride 1
0.1 g was obtained. The yield was 95.3% and the purity was 91%.
【００２０】実施例６ ９８％の硫酸１００ｇに４−ヒドロキシ−１，５，８−
トリアミノアントラキノン−２，３−ジニトリル１０ｇ
を室温で装入し、２００℃で３時間加熱攪拌した。反応
液を室温まで冷却した後、氷水３９０ｇに排出し、濾
過、水洗した後、乾燥し、４−ヒドロキシ−１，５，８
−トリアミノアントラキノン−２，３−ジカルボン酸無
水物１０．３ｇを得た。収率９７．２％、純度９６％で
あった。Example 6 100 g of 98% sulfuric acid was added to 4-hydroxy-1,5,8-
Triaminoanthraquinone-2,3-dinitrile 10 g
Was charged at room temperature, and heated and stirred at 200 ° C. for 3 hours. After the reaction solution was cooled to room temperature, it was discharged into 390 g of ice water, filtered, washed with water, dried, and dried with 4-hydroxy-1,5,8.
10.3 g of triaminoanthraquinone-2,3-dicarboxylic anhydride were obtained. The yield was 97.2% and the purity was 96%.
【００２１】[0021]
【発明の効果】本発明の方法は、簡易な操作によって、
高収率、高純度でアントラキノンジカルボン酸無水物を
得ることができ、工業的にも容易に実施しうる方法であ
る。According to the method of the present invention, a simple operation
Anthraquinone dicarboxylic anhydride can be obtained in high yield and high purity, and this method can be easily carried out industrially.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭63−17854（ＪＰ，Ａ) 特開 昭61−260050（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C07D 307/77 C07D 255/49 - 255/60 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-63-17854 (JP, A) JP-A-61-260050 (JP, A) (58) Fields investigated (Int. Cl. 7 , DB name) C07D 307/77 C07D 255/49-255/60 CA (STN) REGISTRY (STN)
Claims (3)
し、Ｒ2は水素原子、アミノ基、水酸基、およびハロゲ
ン原子を表わし、但し、ｎが２以上の場合はＲ2 は互い
に等しくても異なっていても良い。ｎは１〜４の整数を
表わす。）で示されるアントラキノンジニトリルを、濃
度６０〜１００％の硫酸中、５０〜２００℃で処理する
ことを特徴とする下記一般式（ＩＩ）（化２） 【化２】 （式中、Ｒ1 は水素原子、アミノ基および水酸基を表わ
し、Ｒ2は水素原子、アミノ基、水酸基、およびハロゲ
ン原子を表わし、但し、ｎが２以上の場合はＲ2 は互い
に等しくても異なっていても良い。ｎは１〜４の整数を
表わす。）で示されるアントラキノンジカルボン酸無水
物の製造方法。1. A compound represented by the following general formula (I): (In the formula, R 1 represents a hydrogen atom, an amino group and a hydroxyl group, R 2 represents a hydrogen atom, an amino group, a hydroxyl group and a halogen atom, provided that when n is 2 or more, R 2 may be equal to each other. An anthraquinone dinitrile represented by the following general formula (n) is treated at 50 to 200 ° C. in sulfuric acid having a concentration of 60 to 100%, wherein n is an integer of 1 to 4. II) (Chemical formula 2) (In the formula, R 1 represents a hydrogen atom, an amino group and a hydroxyl group, R 2 represents a hydrogen atom, an amino group, a hydroxyl group, and a halogen atom, provided that when n is 2 or more even R 2 are equal to each other And n represents an integer of from 1 to 4.).
使用量が一般式（I)で表わされるアントラキノンジニト
リルの３〜５０倍重量である請求項１記載の製造方法。2. The process according to claim 1, wherein the sulfuric acid concentration is 80 to 95% and the amount of sulfuric acid used is 3 to 50 times the weight of the anthraquinone dinitrile represented by the general formula (I).
項２記載の製造方法。3. The method according to claim 2, wherein the treatment temperature is 110 to 140 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3096580A JP3045803B2 (en) | 1991-04-26 | 1991-04-26 | Process for producing anthraquinone dicarboxylic anhydride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3096580A JP3045803B2 (en) | 1991-04-26 | 1991-04-26 | Process for producing anthraquinone dicarboxylic anhydride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04327584A JPH04327584A (en) | 1992-11-17 |
| JP3045803B2 true JP3045803B2 (en) | 2000-05-29 |
Family
ID=14168899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3096580A Expired - Fee Related JP3045803B2 (en) | 1991-04-26 | 1991-04-26 | Process for producing anthraquinone dicarboxylic anhydride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3045803B2 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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1991
- 1991-04-26 JP JP3096580A patent/JP3045803B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04327584A (en) | 1992-11-17 |
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