CAS名：Benzamide, N-(5-amino-9,10-dihydro-9,10-dioxo-1-anthracenyl)-

用途：染料中间体。 LookChem网登录生产与经营单位20家。

BIOS 1484, 4.（=胶卷PB 86139）。 1-Amino-5-benzoylaminoanthraquinone. (Leverkusen).  英国人译自德文。

反应式：

Plant: 生产设备：

3000 litre enamelled vessel in oil bath with steam coil。  Pressure filter。   2 X 3 cub. meter tiled Venuleths.

Materials: 投料量：

110 kg. 1,5-diaminoanthraquinone。   1200 litres nitrobenzene。   88 kg. sodium carbonate。   255 litres benzoyl chloride + nitrobenzene mixture

(1 part benzoyl chloride + 2 parts nitrobenzene)。

Method: 操作步骤：

The 1,5-diaminoanthraquinone and 1200 litres benzene are heated to 150 – 155℃., 88 kg. Na2CO3 added, followed by the mixed benzoyl chloride and nitrobenzene.  Heat 2 – 3 hours (60% mono and 40% dibenzoyl are produced).  Blow at 120℃ to the pressure filter, previously well heated, and wash the cake with nitrobenzene at 120℃.  The filtrates and the washing are dried in one Venuleth.

Yield = 95 kg. of 1-amino-5-benzoylaminoanthraquinone.

Recovery: 二苯甲酰化合物的回收：

The dibenzoyl derivative in the filter is dried in the other Venuleth.  Yield = 175 kg. 45%.  It is hydrolysed to 1,5-diaminoanthraquinone for re-use.

FIAT 1313,2, 26-27.（=胶卷PB 85172）。  1-Amino-5-benzoyl amino anthraquinone.  美国人译自德文。

This product is manufactured at Leverkusen by partial benzoylation of 1,5-diamino anthraquinone with benzoyl chloride, in nitrobenzene as solvent.  The dibenzoyl compound is filtered off, leaving the 1-amino-5-b3nzoyl compound in solution in the filtrate, from which it is isolated or, in some cases, used as a standardized solution of the material in nitrobenzene.

The following is a brief description of the method of operation. 以下是操作步骤的简要方法：

110 kg. of 1,5-diamino anthraquinone (sublimed or recovered),  1200 liters of nitrobenzene (dry).

The above materials are placed in an enamelled, jacketed, agitated kettle of 3 cubic meters capacity, equipped with a high pressure heating coil in the jacket which is filled with oil, and the charge heated to 150 – 1600 with 30 atmospheres steam pressure in the coil to expel all moisture.  With the temperature at 150 – 155℃, are then added 88 kg. of dry sodium carbonate after which, at the same temperature, a mixture, of 255 liters of benzoyl chloride with 510 liters of nitrobenzene, is run in slowly over 2 – 3 hours.  The amount of benzoyl chloride used is calculated to convert approximately 40% of the 1,5-diamino anthraquione into the dibenzoyl compound, leaving 60% as 1-amino-5-benzoylamino anthraquinone, with no unchanged diamino anthraquinone in the mixture.

Toward the end of the addition of the benzoyl chloride nitrobenzene mixture a sample of the charge is withdrawn and tested for freedom from unreacted 1,5-amino anthraquinone.  This test is carried out as follows: A portion of the sample is dissolved in a mixture of half and half pyridine and ethyl alcohol, in which the unchanged diamino anthraquinone dissolves with a red color, whereas over-benzoylation produces a yellow shade.  The desired shade is an orange which is compared with standard, made from satisfactory material.

When a proper test has been obtained, the charge is blown to a pressure nutsch and filtered and the nutsch layer is then well washed with three 200 liter washes of hot nitrobenzene at 1200, through the kettle and the pressure nutsch.  The filtrates and wash liquors are run to a 3 cubic meter Venuleth, from which the nitrobenzene is removed by steam distillation and the product dried.  In some cases where the product is to be utilized in a subsequent reaction, to be carried out in nitrobenzene, the solution is analyzed by steam distillation of a sample in the laboratory and the calculation amount of the solution is utilized directly.

The yield, after isolation, is 95 kg. of 1-amino-5-benzoylamino anthraquinone.

The washed nutsch layer is slurried with 500 liters of clean nitrobenzene and blown to a second Venuleth where the solvent is removed by steam distillation and the product dried and discharged.

The yield of 1,5-dibenzoyl diamino anthraquinone = 80 kg. 97% theory.

Since it is always necessary to manufacture considerable amount of the dibenzoyl diamino compound by this process, a method has been worked out to regenerate 1,5-diamino anthraquinone from the dibenzoyl compound when desired, which is carried out as follows:

The dibenzoyl diamino anthraquinone from about 50 charges, equals 4000 kg., (ground but not washed) is added to 4000 liter of water in a 13 cubic meter autoclave, to which is than added 1000 kg. of caustic soda solution (50%).  The autoclave is then made up to a total volume of 6000 liters with water.  The autoclave is closed and heated with 40 atmospheres of steam in the coil to an inner temperature of 210℃. and this temperature is held under agitation for 10 hours, after which a sample is withdrawn and examined for freedom from the dibenzoyl compound under the microscope.  The crystals of the dibenzoyl compound are yellow whereas those of the 1,5-diamino anthraquinone are red.  When the charge is satisfactory, the pressure is released and the contents filtered off on a nutsch at about 90℃., the nutsch layer is washed alkali free with hot water and the product dried.

Yield = 2050 kg., 96% of theory from the dibenzoyl used.

The quality of the recovere 1,5-diamino anthraquinone, obtained as above described, is said to be fully equal and in most cases superior in quality to the best sublimed product and can be reused repeatedly for the manufacture of 1-amino-5-benzoylamino anthraquinone, by the above described process.

The filtrate from the autoclave charge contains sodium benzoate, in solution, which can be recovered by acidification of the filtrate.

张澍声《精细化工中间体工业生产技术》。《染料工业》编辑部 出版。1996年。P. 229. 1-氨基-5-苯甲酰氨基蒽醌，译自FIAT。

在3000 L搪瓷锅中加入110 kg 1,5-二氨基蒽醌和1200 L干硝基苯，加热到150 – 155℃，再加入88 kg干碳酸钠，以及225 L苯甲酰氯和硝基苯混合物（1份苯甲酰氯加2份硝基苯）。加热2 – 3小时，生产60% 单苯甲酰基和40% 二苯甲酰基产品，在120℃进行减压，需预先很好加热，并用3 X 200 L 120℃的硝基苯洗涤3次。滤液和洗水进行干燥，得到95 kg 1-氨基-5-苯甲酰氨基蒽醌。二苯甲酰蒽醌从过滤机中取出，干燥，得到175 kg 1,5-二苯甲酰氨基蒽醌（45%）。它经水解得1,5-二氨基蒽醌，供复用，其质量等于甚至超过升华产品。

将50批，约4000 kg 1,5-二苯甲酰氨基蒽醌和4000 L水加到13 m3高压釜中，再加入1000 kg 50% 氢氧化钠溶液，加水至总体积为6000 L，加热至210℃，在此温度搅拌10小时，在显微镜下检验，应不含二苯甲酰基化合物结晶，二苯甲酰化合物为黄色，而1,5-二氨基蒽醌为红色。检验满意后，释去压力，反应物在90℃抽滤，滤饼用热水洗至不含碱，得到2050 kg 1,5-二氨基蒽醌，以二苯甲酰氨基蒽醌计，收率96%。滤液中含苯甲酸钠，将滤液酸化，可回收苯甲酸。

FIAT 1016, 51.（=胶卷PB 67569）。 Vorschrift zur Fabrikation von 1-Amino-5-benzoylamino-anthrachinon. 美国人抄自德文。

Arbeitsweise:  操作步骤：

110 kg 1,5-Diaminoanthrachinone und 1200 l. trockenes Nitrobenzol werden im Rührwerskessel (1) trockengeheizt.  Anschliessend trägt man bei 150 - 1550  88 kg trockene Soda ein und benzoyliert bei dieser Temperatur mit 225 l. Benzoylchlorid-Nitrobenlmischung 1:2, so dass 40% d. Th. in 1,5-dibenzoyl aminoanthrachinone übergeführt werden.

Die fertige Schmelze wird bei 1200 auf einer gut vorgewärmten Drucknutsche (2) abfilriert und der aus 1,5-Dibenoyl-aminoanthrachinon bestehende Nutschkuchen mit 1200 warmen Nitrobenzol ausgewaschen.  Die Mutterlauge und das Wasch-Nitrobenzol werden im Venuleth (3) zur Trockne eingedampft.  Das anfallende 1,5-Dibenzoylaminoanthrachinon wird im Venuleth (4) getrocknet.

Ausbeute: 收率：95 kg Amino-5-benzoylaminoanthrachinon.

Nebenausbeute: 副产品收率：175 kg 1,5-Dibenzoylaminoanthrachinon 45% ig.

Apparatur: 设备：

1)  3 cbm Rührwerkskessel, Eisen emailliert, im Ölbad mit Dampfschlange für 30 atü. 3立方米搪瓷锅，具油浴，用30巴蒸汽加热。

2)  7 qm Rührdrucknutsche, Eisen säurefest ausgemauert.  7平方米，具耐酸衬里的抽滤机。

3)  Eiserner 3 cbm Venuleth mit Kühler und Destilliervorlagen.  3立方米，具冷却和蒸馏设备的耙式干燥机。

4)  Eiserner 3 cbm Venuleth mit Kühler und Destilliervorlagen.  同上。

PB 25627, 2358-2362. “Goldamid”1934年2月德文生产工艺原件，1美元，未抄录。美国人介绍如下。

This substance is 1-amino-5-benzoylaminoanthraquinone.  Its production from“Fünfamid”and benzoylchloride in nitrobenzene is described.  An attached document contains a discussion of G. A. W. ‘s apparatus, referring to drawings which are not included.  In German.

赵维绳  陈 彬  汪维凤 编著《还原染料》。化学工业出版社 出版。1993年。P. 93. 蒽醌还原染料。

    第一节 酰胺系和亚胺系。

1,5-二氨基蒽醌与1.6 mol苯甲酰氯在硝基苯中，以碳酸钠微缚酸剂，在150 – 155℃下加热3 h，制得1-氨基-5-苯甲酰氨基蒽醌和1,5-二苯甲酰氨基蒽醌，其生成率之比为3 ：2，待物料冷却至120℃时，滤出不溶解的二酰氨基蒽醌后，从母液中回收溶解度较大的单酰化物。

【抄注】全书未提到PB报告德文原件！

何岩彬 主编《染料品种大全》。沈阳出版社 出版。2018年。P. 2030.  中文名称：1-氨基-5-苯甲酰氨基蒽醌

【可合成的染料】C.I. 还原黄10；C.I. 还原黄12；C.I. 还原黄13；C.I. 还原黄17；C.I. 还原黄23；C.I. 还原橙13；C.I. 还原橙15；C.I. 还原橙17； C.I. 还原棕9；C.I. 还原棕26；C.I. 还原棕55。

陈忠源 2020年。/ 2021年6月10日星期四。



文章标签：CAS号 [117-06-6] 生产工艺。 1-氨基-5-苯甲酰氨基蒽醌  
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