溶剂红169 | 27354-18-3

• 物质功能分类: 染料及颜料 - 染料 - 溶剂染料
• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 溶剂红169
• 中文别名: 溶剂红 169；1-异丙基氨基-9,10-蒽二酮；1-异丙胺基蒽醌
• 英文名称: 1-isopropylamino-anthraquinone
• 英文别名: 1-(Isopropylamino)anthraquinone；1-(propan-2-ylamino)anthracene-9,10-dione
• CAS: 27354-18-3
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: ATIYVSUEHXWMKF-UHFFFAOYSA-N

物化性质

• 熔点：
  187-189 ºC
• 沸点：
  470.2±34.0 °C(Predicted)
• 密度：
  1.251

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溶剂红169 在 溴 、 溶剂黄146 作用下， 生成 4-Brom-1-isopropylaminoanthrachinon
  参考文献：
  名称：

  Dyestuffs of the anthraquinone series

  摘要：

  公开号：

  US02168947A1
• 作为产物：
  描述：

  苯酐 、 N-异丙基苯胺 在 硫酸 、 乌洛托品 作用下， 反应 12.08h， 以93.1%的产率得到溶剂红169
  参考文献：
  名称：

  一种溶剂红169的合成方法

  摘要：

  本发明属于染料技术领域，具体涉及一种溶剂红169的合成方法，包括如下步骤：溴苯和异丙胺以水为溶剂，以氯化亚铜为催化剂，在碱性条件下反应得到中间体N‑异丙基苯胺；N‑异丙基苯胺、苯酐在硫酸、乌洛托品的作用下反应得到1‑异丙基氨基蒽醌。本发明提供的溶剂红169的合成方法，以苯酐作为原料直接参与染料的合成，省却了传统工艺上蒽醌、硝基蒽醌以及1‑氯蒽醌的合成过程，大大缩短了工艺路线，从而大幅降低了废弃物的排放，削减了生产成本。

  公开号：

  CN111518409B

文献信息

• Process for the preparation of 1-alkylamino-anthraquinones
  申请人：Bayer Aktiengesellschaft

  公开号：US04163747A1

  公开（公告）日：1979-08-07

  Process for the preparation of 1-alkylamino-anthraquinones which comprises reacting 1-nitroanthraquinone with a monoalkylamine in the presence of an ether, a hydrocarbon or a mixture of an ether and a hydrocarbon. The 1-alkylamino-anthraquinones which are obtained can be employed directly as dyestuffs or used, without further purification, for the production of dyestuffs. Process of the invention results in the procurement of 1-alkylamine-anthraquinones of high purity and in high yield and avoids the formation of undesired by-products.

  制备1-烷基氨基蒽醌的过程包括在醚、烃或醚和烃混合物的存在下，将1-硝基蒽醌与单烷基胺反应。所得到的1-烷基氨基蒽醌可以直接用作染料或在不经过进一步纯化的情况下用于染料的生产。该发明的过程可以高产高纯度的1-烷基氨基蒽醌，并避免了不必要的副产物的形成。
• 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摩尔量的两倍的烷基酸酰胺反应，在100°C至烷基酸酰胺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摩尔量的两倍的烷基酸酰胺同时作为反应物和反应介质反应，在100°C至烷基酸酰胺沸点之间的温度下进行。反应按照一般的反应方程式进行，其中R和R'代表1至8个碳原子的烷基、芳基烷基、环烷基或羟基烷基基团，n为0或1，X代表一个官能基取代物，例如羧基、磺酸基、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。反应可以使用单硝基蒽醌和/或二硝基蒽醌进行。本发明所得到的氨基蒽醌是已知的，是有用的染料或染料中间体。本发明的氨解反应在德国专利号136.777、136.778和144.634中有所描述。然而，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会导致产率非常低，需要较长的反应时间。例如，在75°C下，1-硝基蒽醌与300%过量的异丙胺反应100小时后，仅得到70%的1-异丙基氨基蒽醌收率。瑞士专利申请号12793/74描述了通过使用含有--SO2或--SO基团的双极非质子溶剂作为反应介质，将硝基蒽醌与有机胺反应的氨解反应。该工艺在回收用作反应介质的溶剂方面是令人满意的，可能需要通过蒸馏从作为反应物的胺中分离出来。相比之下，本发明的工艺出乎意料地以非常高甚至定量的收率获得N-烷基氨基和N，N-二烷基氨基蒽醌。产品的纯度很高，因此大多数情况下它们不需要再经过纯化。反应条件简单，反应过程容易控制。在所使用的设备和回收过量的作为反应介质的酸酰胺方面没有腐蚀或技术性问题。反应过程是均匀的，几乎不会产生残留物，因此从生态角度来看，本发明的工艺也是一个重大的进步。反应后，可以通过简单的蒸馏或从产物中过滤掉过量的酸酰胺，几乎完全地回收过量的酸酰胺，并用于新的批次。可以在常规反应器或高压釜中进行氨解反应。适当的设备是旋转蒸发器或用于工业规模批次生产的搅拌干燥器（Venulett）。反应温度将至少为100°C。优选反应温度在160°C至200°C之间。氨解反应可以在有压力和无压力下进行。最好不使用压力。反应时间为0.5至15小时，优选为1至5小时。作为反应物和反应介质的酸酰胺与硝基蒽醌的重量比有利地为4:1至10:1。适用的酸酰胺是HCONHR，RCONHR，HCONRR'，RCONNRR'的公式，或PO（-NRR'）3，SO2（-NRR'）2或SO（-NRR'）2的公式，其中R和R'相同或不同，代表1至8个碳原子的烷基、芳基烷基、环烷基或羟基烷基基团。由每个R和R'代表的烷基组可以相同或不同，直链或支链，并且特别是1至4个碳原子的低分子烷基组，如甲基、乙基、丙基、异丙基、叔丁基，或长链烷基组，如己基或辛基。由每个R和R'代表的环烷基组特别是环己基组，由R和R'代表的芳基烷基组主要是苄基或苯乙基组。最好每个R和R'都代表较低的烷基组。可以使用的酸酰胺的例子是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酰胺或四甲基硫酰二胺。例如，反应可以这样进行，即将反应物硝基蒽醌和酸酰胺加入反应器中，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，并可以被再次使用。在许多情况下，产物在反应混合物冷却后结晶出来，因此通过过滤分离，母液（即带有少量溶解的产物的过量酸酰胺）可以再次用于进一步的反应。很容易理解，也可以通过将反应混合物稀释水或醇并随后过滤来分离产物。以下实例说明本发明的工艺，但不意味着对所描述的内容有任何限制。
• Verfahren zur Herstellung substituierter 1-Aminoanthrachinone
  申请人：BAYER AG

  公开号：EP0001249A1

  公开（公告）日：1979-04-04

  Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von substituierten 1-Aminoanthrachinonen durch Umsetzung von 1-Nitroanthrachinon mit Aminen in wässriger Suspension, wobei man 1-Nitroanthrachinon mit einer mittleren Partikelgröße von über 100 Mikron verwendet und das 1-Nitroanthrachinon und das Amin bei Reaktionstemperatur zusammengibt. Bei diesem Verfahren kann 1-Nitroanthrachinon so eingesetzt werden, wie es nach üblichen Herstellungs- und Reinigungsmethoden erhalten wird. Das Verfahren kann mit relativ geringen Aminmengen durchgeführt werden und die 1-Aminoanthrachinone werden in hohen Reinheiten und Ausbeuten erhalten.

  本发明涉及一种通过在水悬浮液中使 1-硝基蒽醌与胺反应来制备取代的 1-氨基蒽醌的工艺，其中使用平均粒径大于 100 微米的 1-硝基蒽醌，并在反应温度下将 1-硝基蒽醌与胺结合。 在该工艺中，可以使用通过常规制备和纯化方法获得的 1-硝基蒽醌。 该工艺可以使用相对少量的胺，并以高纯度和高产率获得 1-氨基蒽醌。
• Verfahren zur Herstellung von 1-Alkylaminoanthrachinonen
  申请人：BAYER AG

  公开号：EP0063298A1

  公开（公告）日：1982-10-27

  Verbessertes Verfahren zur Herstellung von 1-Alkylamino-anthrachinonen durch Aminolyse von 1-Nitroanthrachinonen mit Alkylaminen bei erhöhter Temperatur in Wasser und organischen, mit Wasser nicht mischbaren Lösungsmitteln in Gegenwart von Säurebindemitteln, gemäß dem als Säurebindemittel Calciumhydroxid verwendet wird.

  一种改进的制备 1-烷基氨基蒽醌的工艺，该工艺是在酸性粘合剂存在下，通过 1-硝基蒽醌与烷基胺在高温下于水和有机水不溶溶剂中进行氨解来制备 1-烷基氨基蒽醌，根据该工艺，氢氧化钙被用作酸性粘合剂。
• POLYMERIZABLE COMPOSITION FOR OPTICAL MATERIAL, AND MOLDED ARTICLE
  申请人：Mitsui Chemicals, Inc.

  公开号：EP3722840A1

  公开（公告）日：2020-10-14

  The polymerizable composition for an optical material of the present invention includes an allyl carbonate compound (A) including two or more allyloxycarbonyl groups which is represented by General Formula (1); a (meth)acrylate compound (B) including two or more (meth)acryl groups which is represented by General Formula (2); at least one kind of compound (C), selected from compounds represented by General Formulas (3) to (6) and dyes described below; and a polymerization initiator (D) including at least a radical polymerization initiator (D1) and a radical polymerization initiator (D2), in which, in 100% by weight in a total of the compound (A) and the compound (B), the compound (A) is included in an amount of more than 0% by weight and 30% by weight or less and the compound (B) is included in an amount of 70% by weight or more and less than 100% by weight, the radical polymerization initiator (D1) has a radical residual ratio after 5 hours at 50°C of 20% or more and less than 100% and a radical residual ratio after 5 hours at 70°C of 0% or more and less than 30%, and the radical polymerization initiator (D2) has a radical residual ratio after 5 hours at 70°C of 30% or more and less than 98%.

  本发明光学材料的可聚合组合物包括通式(1)表示的包括两个或两个以上烯丙氧羰基的碳酸烯丙酯化合物(A)；通式(2)表示的包括两个或两个以上(甲基)丙烯酰基的(甲基)丙烯酸酯化合物(B)；至少一种化合物(C)，选自通式(3)至(6)表示的化合物和下述染料；和聚合引发剂 (D)，至少包括自由基聚合引发剂 (D1) 和自由基聚合引发剂 (D2)，其中化合物 (A) 和化合物 (B) 的总重量为 100%，化合物 (A) 的含量大于 0%（以重量计）且小于 30%（以重量计），化合物 (B) 的含量大于 70%（以重量计）且小于 100%（以重量计）、自由基聚合引发剂（D1）在 50°C 下 5 小时后的自由基残留率为 20%或以上且小于 100%，在 70°C 下 5 小时后的自由基残留率为 0%或以上且小于 30%，自由基聚合引发剂（D2）在 70°C 下 5 小时后的自由基残留率为 30%或以上且小于 98%。