1,8-二(甲基氨基)蒽醌 | 60316-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1,8-二(甲基氨基)蒽醌
• 英文名称: 1,8-bis-methylaminoanthraquinone
• 英文别名: 1,8-Dimethylamino-9,10-anthraquinone；1,8-dimethylaminoanthraquinone；1,8-bis-methylamino-anthraquinone；1,8-Bis-methylamino-anthrachinon；9,10-Anthracenedione, 1,8-bis(methylamino)-；1,8-bis(methylamino)anthracene-9,10-dione
• CAS: 60316-43-0
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: WBNXSOGPMIRTPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922399090

反应信息

• 作为反应物：
  描述：

  1,8-二(甲基氨基)蒽醌 在 溴 、 copper diacetate 、 sodium acetate 、 potassium carbonate 、 硝基苯 作用下， 生成 1,8-bis-methylamino-4,5-bis-(toluene-4-sulfonylamino)-anthraquinone
  参考文献：
  名称：

  145. 1：4：5：8-四氨基氨基蒽醌的甲基衍生物

  摘要：

  DOI：

  10.1039/jr9480000736
• 作为产物：
  描述：

  1,8-二硝基蒽醌 在 氢氧化钾 作用下， 生成 1,8-二(甲基氨基)蒽醌
  参考文献：
  名称：

  DE158531

  摘要：

  公开号：

文献信息

• Perfluoroalkylquinones. Synthesis Using Bis(perfluoroalkanoyl) Peroxides, Absorption Bands, and Solubility
  作者：Masaki Matsui、Shigeru Kondoh、Katsuyoshi Shibata、Hiroshige Muramatsu

  DOI：10.1246/bcsj.68.1042

  日期：1995.3

  The reactions of 1,4-benzo-, naphtho-, and 9,10-anthraquinones with bis(perfluoroalkanoyl) peroxides gave the corresponding perfluoroalkylated derivatives. Those of 2-methyl- and 2-[4-(chloroanilino)]-1,4-naphthoquinones with bis(oxaperfluoroalkanoyl) peroxides afforded the dichloromethyl and trifluoromethyl derivatives, respectively. Absorption bands of the perfluoroalkylated naphtho- and anthraquinone dyes showed a slight hypsochromic shift. The solubilities of the perfluoroalkylated anthraquinone dyes into hexane were much more higher than those of the non-perfluoroalkylated ones.

  1,4-苯并蒽醌、萘并蒽醌和 9,10-蒽醌与双（全氟烷酰基）过氧化物的反应生成了相应的全氟烷基化衍生物。2-甲基和 2-[4-(氯苯胺基)]-1,4-萘醌与双(氧代全氟烷酰基)过氧化物的反应分别产生了二氯甲基和三氟甲基衍生物。全氟烷基化萘醌和蒽醌染料的吸收带显示出轻微的低色移。全氟烷基化蒽醌染料在正己烷中的溶解度远高于非全氟烷基化蒽醌染料。
• Process for the manufacture of N-alkylamino- and
  申请人：Ciba-Geigy Corporation

  公开号：US04044030A1

  公开（公告）日：1977-08-23

  A process for the manufacture of N-alkylamino- and N,N-dialkylaminoanthraquinone from the corresponding nitroanthraquinones, which comprises reacting substituted or unsubstituted nitroanthraquinones or dinitroanthraquinones with at least twice the molar amount, referred to the nitro groups to be reacted, of an alkyl acid amide, at temperatures between 100.degree. C and the boiling point of the alkyl acid amide. The present invention provides a process for the manufacture of N-alkylamino- and N,N-dialkylaminoanthraquinones from the corresponding nitroanthraquinones, which process comprises reacting substituted or unsubstitued nitroanthraquinones or dinitroanthraquinones with at least twice the molar amount, referred to the nitro groups to be reacted, of an alkyl acid amide which is simultaneously reactant and reaction medium, at temperatures between 100.degree. C and the boiling point of the alkyl acid amide. The reaction takes place according to the general reaction equation ##STR1## wherein R and R', which are the same or different, represent alkyl, aralkyl, cycloalkyl or hydroxyalkyl radicals of 1 to 8 carbon atoms, n is 0 or 1, X represents a functional substituent, for example the carboxyl, sulpho, hydroxy, amino or halogen group, which can be attached direct or through a bridge member to the anthraquinone nucleus. The reaction can be carried out with mononitroanthraquinones and/or dinitroanthraquinones. The aminoanthraquinones obtained by the process of this invention are known and are useful dyes or dyestuff intermediates. The aminolysis of nitroanthraquinones is described in German Pat. Nos. 136.777, 136.778 and 144.634. However, polar solvents, such as water, alcohols or pyridine, are used as reaction media therein. The use of polar solvents as reaction media results in only very poor yields and lengthy reaction times are required. For example, the reaction of 1-nitroanthraquinone with a 300% excess of isopropylamine at 75.degree. C after 100 hours gives a yield of only 70% of 1-isopropylaminoanthraquinone. Swiss Pat. application No. 12793/74 describes the aminolysis by reacting nitroanthraquinones with organic amines using dipolar aprotic solvents which contain --SO.sub.2 or --SO groups as reaction media. This process is satisfactory up to the recovery of the solvents used as reaction medium, which may have to be separated by distillation from the amines used as reactants. By comparison, N-alkylamino- and N,N-dialkylamino-anthraquinones are obtained surprisingly in very high and often even quantitative yields by the process of this invention. The products are obtained in a high degree of purity, so that mostly they do not need to be purified any more. The reaction conditions are simple and the reaction course is easily kept under control. No problems regarding corrosion or of a technical nature arise in respect of the apparatus used and the recovery of the excess acid amide used as reaction medium presents no difficulties. The reaction course is uniform and virtually no residues occur, so that the process of this invention also marks a considerable advance especially from the ecological standpoint. The excess acid amide can be almost completely recovered after the reaction by simple distillation or by filtering it off from the product, and reused for a fresh batch. Examples of aminoanthraquinones which can be obtained by the process of this invention are: 1-isopropylaminoanthraquinone, 1-isobutylamino-2-methylanthraquinone, 1-methylaminoanthraquinone, 1-diethylaminoanthraquinone, 1-cyclohexylaminoanthraquinone, the sodium salt of 1-isopropylaminoanthraquinone-6/7-sulphonic acid, 1-isobutylaminoanthraquinone, 1-diisopropyl-, 1-diisobutyl- and 1-dicyclohexylaminoanthraquinone, 1-isopropylamino-2-methylanthraquinone 1-cyclohexylamino-2-methylanthraquinone, 1,5-bis-methylaminoanthraquinone and 1-dimethylaminoanthraquinone. The aminolysis is carried out in conventional reaction vessels or autoclaves. A suitable apparatus is the rotary evaporator or, for batches produced on an industrial scale, the paddle drier (Venulett). The reaction temperature will be at least 100.degree. C. The preferred reaction temperature is between 160.degree. and 200.degree. C. The aminolysis can be carried out both under pressure and without pressure. It is preferred to operate without pressure. The reaction time is from 0.5 to 15 hours, preferably 1 to 5 hours. The weight ratio of the acid amide as reactant and reaction medium to the nitroanthraquinone is advantageously between 4:1 to 10:1. Suitable acid amides are those of the formulae HCONHR, RCONHR, HCONRR', RCONNRR' or those of the formulae PO(--NRR').sub.3, SO.sub.2 (--NRR').sub.2 or SO(--NRR').sub.2, wherein R and R', which are the same or different, represent alkyl, aralkyl, cycloalkyl or hydroxyalkyl radicals of 1 to 8 carbon atoms. An alkyl group represented by each of R and R' can be the same or different, straight-chain or branched, and is in particular a low molecular alkyl group of 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl, tert.butyl, or a long-chain alkyl group, such as hexyl or octyl. A cycloalkyl group represented by each of R and R' is in particular the cyclohexyl group and an aralkyl group represented by R and R' is above all the benzyl or phenethyl group. Preferably each of R and R' represents a lower alkyl group. Examples of acid amides which can be used according to the invention are: N-methyl formamide, N-methyl acetamide, N,N-dimethyl formamide, N-ethyl formamide and hexamethylphosphoric triamide or tetramethyl thionyl diamide. The reaction is carried out, for example, in such a way that the reactants, nitroanthraquinone and acid amide, are charged into a reaction vessel and stirred for several hours at temperatures between 100.degree. and 200.degree. C. When the reaction is complete, the excess acid amide is distilled off and can be reused. In many cases the product crystallises out after the reaction mixture has cooled, so that it is separated by filtration, and the mother liquor (i.e., excess acid amide with a small amount of dissolved product) can be reused for further reactions. It will be readily understood that the products can also be isolated by diluting the reaction mixture with water or alcohols and subsequent filtration. The following Examples illustrate the process of the present invention without implying any restriction to what is described therein. The parts are by weight.

  一种从相应的硝基蒽醌制备N-烷基氨基蒽醌和N,N-二烷基氨基蒽醌的工艺，包括将取代或未取代的硝基蒽醌或二硝基蒽醌与至少是硝基反应物的摩尔量的烷基酸酰胺反应，在100°C至烷基酸酰胺的沸点之间的温度下进行。本发明提供了一种从相应的硝基蒽醌制备N-烷基氨基蒽醌和N,N-二烷基氨基蒽醌的工艺，该工艺包括将取代或未取代的硝基蒽醌或二硝基蒽醌与至少是硝基反应物的摩尔量的烷基酸酰胺反应，该烷基酸酰胺同时是反应物和反应介质，在100°C至烷基酸酰胺的沸点之间的温度下进行。反应按照以下一般反应方程式进行： 其中R和R'，相同或不同，代表1至8个碳原子的烷基、芳基、环烷基或羟基烷基基团，n为0或1，X代表功能性取代基，例如羧基、磺酰基、羟基、氨基或卤素基，可以直接或通过桥接成员连接到蒽醌核上。该反应可以用一硝基蒽醌和/或二硝基蒽醌进行。本发明的工艺得到的氨基蒽醌是已知的，可用作染料或染料中间体。硝基蒽醌的氨解作用在德国专利号136.777、136.778和144.634中有描述。但是，在其中使用极性溶剂，如水、醇或吡啶作为反应介质。使用极性溶剂作为反应介质导致产率非常低，需要较长的反应时间。例如，1-硝基蒽醌与异丙胺的300%过量在75°C反应100小时后，只能得到70%的1-异丙氨基蒽醌。瑞士专利申请号12793/74描述了通过将硝基蒽醌与含有--SO2或--SO基团的有机胺在二极非亲核溶剂中反应来进行氨解的方法。与之相比，通过本发明的工艺，N-烷基氨基蒽醌和N,N-二烷基氨基蒽醌以非常高甚至定量的产率出乎意料地得到。产品的纯度很高，因此大多数情况下不需要再纯化。反应条件简单，反应过程易于控制。在使用的设备方面不会出现腐蚀或技术性质的问题，过量烷基酸酰胺作为反应介质的回收也不困难。反应过程均匀，几乎没有残留物产生，因此从生态角度看，本发明的工艺也标志着相当大的进步。反应后，通过简单蒸馏或从产物中过滤就可以几乎完全回收过量烷基酸酰胺，并用于新一批次。可通过本发明的工艺获得的氨基蒽醌的示例包括：1-异丙氨基蒽醌、1-异丁氨基-2-甲基蒽醌、1-甲基氨基蒽醌、1-二乙基氨基蒽醌、1-环己基氨基蒽醌、1-异丙氨基蒽醌-6/7-磺酸钠盐、1-异丁氨基蒽醌、1-二异丙基、1-二异丁基和1-二环己基氨基蒽醌、1-异丙氨基-2-甲基蒽醌、1-环己基氨基-2-甲基蒽醌、1,5-双甲基氨基蒽醌和1-二甲基氨基蒽醌。氨解可在常规反应容器或高压釜中进行。适合的设备有旋转蒸发器或用于工业规模生产的搅拌干燥器（Venulett）。反应温度至少为100°C。首选的反应温度在160°C至200°C之间。氨解可以在压力下或无压力下进行。最好在无压力下操作。反应时间为0.5至15小时，首选为1至5小时。烷基酸酰胺作为反应物和反应介质与硝基蒽醌的重量比优选为4:1至10:1。适用的烷基酸酰胺是具有HCONHR、RCONHR、HCONRR'、RCONNRR'或PO(--NRR')3、SO2(--NRR')2或SO(--NRR')2式的化学式的烷基酸酰胺，其中R和R'，相同或不同，代表1至8个碳原子的烷基、芳基、环烷基或羟基烷基基团。R和R'各自代表的烷基组可以相同或不同，直链或支链，特别是1至4个碳原子的低分子烷基组，例如甲基、乙基、丙基、异丙基、叔丁基，或长链烷基组，例如己基或辛基。R和R'各自代表的环烷基组特别是环己基组，R和R'代表的芳基组主要是苄基或苯乙基。最好R和R'各自代表较低的烷基组。可根据本发明使用的酸酰胺的例子包括：N-甲基甲酰胺、N-甲基乙酰胺、N,N-二甲基甲酰胺、N-乙基甲酰胺和六甲基磷酸三胺或四甲基硫酰二胺。例如，可以这样进行反应：将反应物硝基蒽醌和酸酰胺加入反应容器中，在100°C至200°C的温度下搅拌数小时。当反应完成后，过量的酸酰胺被蒸馏掉，并且可以再次使用。在许多情况下，反应混合物冷却后产物结晶出来，因此通过过滤分离，母液（即过量酸酰胺与少量溶解的产物）可以用于进一步的反应。可以理解，也可以通过用水或醇稀释反应混合物并随后过滤来分离产物。以下示例说明了本发明的工艺，但不意味着对其中描述的内容有任何限制。单位为重量部分。
• Process for producing disperse dyes
  申请人：Ciba-Geigy Corporation

  公开号：US04304725A1

  公开（公告）日：1981-12-08

  A process for producing disperse dyes starting with anthraquinone compounds of the formula I ##STR1## in which one X is bromine and the other X is methylamine, or with mixtures thereof, which process comprises reacting these compounds with sulfuric acid, optionally containing SO.sub.3, in the presence of boric acid, at a temperature of between 100.degree. and 150.degree. C., to give compounds of the formula II ##STR2## in which one Y is hydroxyl and the other Y is methylamine, and n is 0.5 to 2.0, or mixtures thereof.

  一种生产分散染料的方法，起始物为公式I的蒽醌化合物##STR1## 其中一个X是溴，另一个X是甲胺，或其混合物，该方法包括在硼酸存在下，将这些化合物与含有SO.sub.3的硫酸反应，在100℃至150℃的温度下，得到公式II的化合物##STR2## 其中一个Y是羟基，另一个Y是甲胺，n为0.5至2.0，或其混合物。
• DE165728
  申请人：——

  公开号：——

  公开（公告）日：——
• Gorelik, M. V.; Shapet'ko, N. N.; Arinich, L. V., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 547 - 556
  作者：Gorelik, M. V.、Shapet'ko, N. N.、Arinich, L. V.、Tsurkan, A. I.、Kukushkina, M. L.

  DOI：——

  日期：——