公开(公告)号：US4349478A

公开(公告)日：1982-09-14

申请号：US310576

申请日：1981-10-09

申请人： Zdenek Seha

发明人： Zdenek Seha

IPC分类号： C09B5/26 ,  C09B5/28 ,  C07D209/86

CPC分类号： C09B5/28

摘要： There is described a process for producing vat dyes by carbazolation of anthrimides effected by reaction of a complex of titanium tetrahalide (chloride or bromide) with a sulfone in a medium of the sulfone as the solvent. Further subject matter of the invention is a single-vessel process, in which both the production of the anthrimide and the cyclisation thereof can be performed, without isolation of an intermediate, in a sulfone as the reaction medium.

摘要翻译： 描述了通过在砜的介质中作为溶剂的四卤化钛（氯化物或溴化物）与砜的配合物的反应而进行的通过咔咔咔咔咔咔啉的制造来生产瓮染料的方法。 本发明的另外的主题是一种单容器方法，其中可以在作为反应介质的砜中不进行中间体的分离，同时进行二氯甲烷的生成和其环化。

公开(公告)号：US4021456A

公开(公告)日：1977-05-03

申请号：US575565

申请日：1975-05-08

申请人： Zdenek Seha

发明人： Zdenek Seha

IPC分类号： C07C225/34 ,  C09B1/22 ,  C09B1/16

CPC分类号： C09B1/22

摘要： A process for the manufacture of 1-aminoanthraquinone and derivatives thereof and of diaminoanthraquinones by reduction of 1-nitroanthraquinone and the corresponding derivatives thereof and dinitroanthraquinone, which process comprises the use of a hydronaphthalene as reducing agent and solvent.

摘要翻译： 通过还原1-硝基蒽醌及其相应的衍生物和二硝基蒽醌制备1-氨基蒽醌及其衍生物和二氨基蒽醌的方法，该方法包括使用氢化萘作为还原剂和溶剂。

公开(公告)号：US4076735A

公开(公告)日：1978-02-28

申请号：US612811

申请日：1975-09-12

申请人： Zdenek Seha

发明人： Zdenek Seha

IPC分类号： C09B1/28 ,  C09B1/30 ,  C09B1/16

CPC分类号： C09B1/28 ,  C09B1/303

摘要： A process for the manufacture of aminoanthraquinones, wherein nitroanthraquinones are reacted in dipolar aprotic solvents which contain --SO.sub.2 -- or --SO-- groups and are inert to the reactants, with aliphatic, aliphatic-aromatic, cycloaliphatic, substituted or unsubstituted primary or secondary amines of the formulae R--NH.sub.2 or R--R'--NH, in which R and R' are radicals that are the same or different, such as alkyl, aralkyl, cycloalkyl, hydroxyalkyl radicals of 1 to 8 carbon atoms.

摘要翻译： 制备氨基蒽醌的方法，其中硝基蒽醌在含有-SO 2 - 或-SO-基团并对反应物惰性的偶极非质子溶剂中与脂族，脂族 - 芳族，脂环族，取代或未取代的伯或仲胺反应 式R-NH 2或R-R'-NH，其中R和R'是相同或不同的基团，例如具有1至8个碳原子的烷基，芳烷基，环烷基，羟基烷基。

公开(公告)号：US3998839A

公开(公告)日：1976-12-21

申请号：US426266

申请日：1973-12-19

申请人： Zdenek Seha

发明人： Zdenek Seha

IPC分类号： C09B47/067 ,  C09B47/30 ,  C09B47/08

CPC分类号： C09B47/30 ,  C09B47/067

摘要： Process for the preparation of metal-free phthalocyanine, wherein 4 moles of phthalonitrile are reacted with 0.05 to 0.3 mole of anhydrous alkali sulphide in an inert organic solvent having a boiling point higher than 130.degree. C, in the presence of 0.5 to 3 equivalents of an alcohol having a boiling point higher than 130.degree. C, at temperatures of between 100.degree. C and the boiling point of the solvent and alcohol, respectively.

公开(公告)号：US4065478A

公开(公告)日：1977-12-27

申请号：US640372

申请日：1975-12-15

申请人： Zdenek Seha

发明人： Zdenek Seha

IPC分类号： C09B1/22 ,  C07C20060101 ,  C07C67/00 ,  C07C205/47 ,  C07C225/34 ,  C07C227/04 ,  C07C229/74 ,  C07C313/00 ,  C09B51/00 ,  C07C97/24

CPC分类号： C07C225/34

摘要： A process for the manufacture of .alpha.,.alpha.'-aminonitroanthraquinones, from .alpha.,.alpha.'-dinitroanthraquinones, wherein the .alpha.,.alpha.'-dinitroanthraquinones are reacted with ammonia in dipolar aprotic solvents which are inert to ammonia, the reaction substrates and reaction products.

摘要翻译： 用于从α，α'-二硝基蒽醌生产α，α'-氨基三氟蒽醌的方法，其中所述α，α'-二硝基蒽醌与氨反应，其对氨惰性的偶极非质子溶剂，反应底物和反应产物。

公开(公告)号：US4044030A

公开(公告)日：1977-08-23

申请号：US688517

申请日：1976-05-20

申请人： Zdenek Seha

发明人： Zdenek Seha

IPC分类号： C09B1/28 ,  C09B1/30 ,  C09B1/515 ,  C09B1/16 ,  C09B1/20

CPC分类号： C09B1/28 ,  C09B1/30 ,  C09B1/515

摘要： 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.

摘要翻译： 一种从相应的硝基蒽醌制备N-烷基氨基 - 和N，N-二烷基氨基蒽醌的方法，其包括使取代或未取代的硝基蒽醌或二硝基蒽醌与至少两倍摩尔量的硝基蒽醌或二硝基蒽醌反应， 酸酰胺，在100℃和烷基酰胺的沸点之间。

公开(公告)号：US3933866A

公开(公告)日：1976-01-20

申请号：US400759

申请日：1973-09-26

申请人： Zdenek Seha

发明人： Zdenek Seha

IPC分类号： C07C225/34 ,  C07C20060101 ,  C09B1/22 ,  C07C87/64

CPC分类号： C09B1/28

摘要： A process for the manufacture of aminoanthraquinones from nitroanthraquinone, wherein the nitroanthraquinones are treated with ammonia in dipolar aprotic solvents that are inert towards ammonia and nitroanthraquinones.

摘要翻译： 用于从硝基蒽醌制造氨基蒽醌的方法，其中硝基蒽醌用氨在对氨和硝基蒽醌惰性的偶极非质子传递溶剂中处理。