cas 479-27-6, 1,8-Diaminonaphthalene | Articles data

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Preparation method of a plurality of (hetero) aromatic polyamines
The invention relates to the field of organic functional new material chemicals, and discloses a novel process technology for preparing a plurality of (hetero) aromatic polyamines through corresponding (hetero) aromatic polyfunctional hydroxamic acids (hydroxamic acid) before (re-arrangement). These (hetero) aromatic polyamines are well-known dyes and pigment and pharmaceutical pesticide-related fields of very wide range of critical fine chemical materials.
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Paragraph 0018-0021; 0051-0052; 0054

(2021/09/15)

Boronic, diboronic and boric acid esters of 1,8-naphthalenediol-synthesis, structure and formation of boronium salts
The 1,8-naphthalenediolate [1,8-O2C10H8] supported boronic and boric acid esters of general formula X-B(1,8-O2C10H8), where X = C6H5 (1a), C6F5 (2a), 3,4,5-F3-C6H2 (3a), 2,4,6-F3-C6H2 (4a), 2,6-F2-C6H3 (5a), 2,6-Cl2-C6H3 (6a), 2,4,6-Me3-C6H2 (7a), 2,6-(MeO)3-C6H3 (8a), Bun (9a), MeO (10a), OH (11a) and Cl (13a), were synthesized, NMR spectroscopically characterized, and the solid-state structures of 1a-5a, 8a and 10a determined by X-ray crystallography. The acceptor numbers of 1a-7a and 13a were determined and found to be similar to their catecholate analogues, R-Bcat, indicating similar Lewis acidities of these two classes of boronic acid esters. The reaction of B2(NMe2)4 with 1,8-naphthalenediol, followed by addition of HCl furnished the diboronic acid ester B2(1,8-O2C10H8)4 (16a) in ca. 70% yield. Cl-B(1,8-O2C10H8) (13a) was shown to react with OPEt3, DMAP, 1,10-phenanthroline and 2,2′-bipyridine, resp., to give the boronium salts [(Et3PO)2B(1,8-O2C10H8)]Cl (18a), [(DMAP)2B(1,8-O2C10H8)]Cl (22a), [(2,2′-bipyridine)B(1,8-O2C10H8)]Cl (23a) and [(1,10-phenanthroline)B(1,8-O2C10H8)]Cl (24a), which were characterized by NMR spectroscopy and X-ray crystallography.
Krempner, Clemens,Manankandayalage, Chamila P.,Unruh, Daniel K.
supporting information
p. 4834 - 4842
(2020/04/27)

Activated carbon supported bimetallic catalysts with combined catalytic effects for aromatic nitro compounds hydrogenation under mild conditions
Non-noble nickel catalysts have been widely studied and tried in hydrogenation, however the problem of nickel particle sintering is more and more common in high-loaded nickel catalysts. A series of highly dispersed bimetallic Ni-M/AC (M = Cu, Co, Fe or Zn) catalysts were prepared by incipient wetness impregnation methods and applied in 1-nitronaphthalene hydrogenation to 1-naphthylamine under mild reaction conditions. The prepared catalysts were characterized by XRD, BET, H2-TPR, TEM, HRTEM, HAADF-STEM, XPS, ICP, FT-IR and H2 chemisorption. The results show that the introduction of the metal promoter inhibits the sintering of the nickel and enhances the reducibility of the catalysts, leading to higher ratio of effective Ni° on the surface of the support, especially for Ni-Zn/AC sample. Moreover, the results of XPS indicate that the electron donating effect of Cu promoter increases surface electronic density of Ni, as a result, the electron-rich Ni might be produced because of the interfacial electronic effect, which favors the desorption and further impedes the hydrogenation of N-naphthylhydroxylamine. Ni-Zn/AC-350 with smaller nickel particles, better dispersion and larger content of effective Ni° presents the best catalytic performance in 1-nitronaphthalene hydrogenation to 1-naphthylamine under mild reaction conditions, it gives 100% conversion of 1-nitronaphthalene and 96.82% selectivity to 1-naphthylamine under 0.6 MPa and 90℃ for 5 h. Additionally, superior performances are also obtained in hydrogenation reactions of nitrobenzene, chloronitrobenzene, 1,5-dinitronaphthalene and 1,8-dinitronaphthalene over Ni-Zn/AC catalysts. With good hydrogenation activity the catalyst shows, the application prospect in industrial production of aromatic amine from aromatic nitro compounds has been becoming more and more extension.
Huang, Lei,Lv, Yang,Wu, Shengtao,Liu, Pingle,Xiong, Wei,Hao, Fang,Luo, He'an
p. 76 - 85
(2019/04/01)

N-doped graphitic carbon-improved Co-MoO3 catalysts on ordered mesoporous SBA-15 for chemoselective reduction of nitroarenes
Metallic Co-MoO3 catalysts supported on ordered mesoporous SBA-15 were first prepared through in situ reaction of SBA-15-supported Co-Mo oxides with 1,10-phenanthroline. The resulting Co-MoO3/NC@SBA-15 catalysts with N-doped carbon (NC) exhibited high catalytic activity and chemoselectivity for selective reduction of various functionalized nitroarenes to the corresponding arylamines in ethanol with hydrazine hydrate at near room temperature (30 °C). For reduction of all tested substrates (28 examples), the catalyst could afford a conversion of >99% and arylamine selectivity of >99%. The excellent catalytic performance of the Co-MoO3/NC@SBA-15 was attributed to the Co-Nχ(C)-Mo active sites generated through the interaction between the surface Co-Nχ(C) and MoO3 species, promoting the dissociation of hydrazine molecule into the active H* species for the reduction of nitro groups. After the seventh cycle for reduction of 4-methoxylnitrobenzene, the 2%Co-MoO3/NC@SBA-15 showed little change in catalytic performance, textural properties, size and dispersion of metal species and valence states of elements, indicating high stability and recyclability.
Huang, Haigen,Liang, Xiangcheng,Wang, Xueguang,Sheng, Yao,Chen, Chenju,Zou, Xiujing,Lu, Xionggang
p. 127 - 137
(2018/05/04)

A Co2B Mediated NaBH4 Reduction Protocol Applicable to a Selection of Functional Groups in Organic Synthesis
A high-yielding and high-rate reduction method that operates with alkenes, alkynes, azides, nitriles, and nitroarenes was developed and optimized. The method makes use of sodium borohydride reduction of CoSO4 under release of hydrogen along with the formation of Co2B as a nanoparticle material. The produced Co2B activates the various functional groups for hydride reduction. The protocol was proven to operate with an assortment of functional groups to provide good to excellent yields. Furthermore, the reduction method was successfully adapted, implemented, and developed for a continuous flow approach using the multi-jet oscillating disk (MJOD) flow reactor platform at atmospheric pressure.
Lundevall, Frida Johanne,Elumalai, Vijayaragavan,Drageset, Audun,Totland, Christian,Bj?rsvik, Hans-René
supporting information
p. 3416 - 3425
(2018/07/29)

Method for preparing diaminonaphthalene
The invention provides a method for preparing diaminonaphthalene. The method comprises the following steps: carrying out a nitration reaction by adopting sulfuric acid, fuming nitric acid and naphthalene so as to obtain mixed dinitronaphthalene; adding a second organic solvent, the mixed dinitronaphthalene, a catalyst and activated carbon into a reaction kettle, raising the temperature to 60-65 DEG C, adding hydrazine hydrate, and reacting and separating so as to obtain second filtrate and second filter cake; separating and purifying the second filtrate so as to obtain a solid, namely 1,8-diaminonaphthalene; and separating and purifying the second filter cake so as to obtain 1,5-diaminonaphthalene. According to the preparation of the mixed dinitronaphthalene, the nitratlon reaction is carried out by adopting an organic solvent free method, the waste acid can be recycled, and the yield and treatment cost of the three wastes can be reduced. The mixed dinitronaphthalene is directly reduced, the separation cost is reduced, and the market competitiveness is improved for industrial production. By utilizing different physical properties of the mixed dinitronaphthalene in different organic solvents, 1,8-diaminonaphthalene and 1,5-diaminonaphthalene with high purity are separated.
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Paragraph 0042; 0043; 0049-0054; 0056-0061

(2017/08/29)

1,8-diaminonaphthalene method for industrially preparing
The invention discloses an industrialized preparation method of 1,8-diaminonaphthalene, which comprises the following steps: sequentially adding a catalyst, dinitronaphthalene and a solvent into a reaction kettle, stirring and heating materials in the reaction kettle to a temperature of 65-75 DEG C, slowly dripping hydrazine hydrate, then continuously heating materials in the reaction kettle to the temperature of 75-90 DEG C and keeping the temperature for 3-8 hours until the end of the reaction; cooling the materials after the reaction to the temperature of 40-45 DEG C for pressure filtration, washing and recovering the catalyst obtained through pressure filtration, and mixing the washing liquid and the filtering liquid to obtain a feed liquid; conducting decompression and desolvation on the feed liquid to recover the solvent; adding hot water with the temperature of 50-80 DEG C into the desolventized feed liquid for water washing stratification, wherein the upper layer is water phase and the lower layer is feed liquid phase; feeding the feed liquid phase obtained through stratification into a rectifying tower for rectification, and obtaining 1,8-diaminonaphthalene, wherein the purity of 1,8-diaminonaphthalene at the top of the rectifying tower is equal to or larger than 99.5%. The dinitronaphthalene raw materials comprise water and an organic solvent, wherein the organic solvent comprises an organic solvent used by a naphthaline-nitrified product in refining.
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Paragraph 0024-0037

(2017/01/23)

Carbon nitride supported palladium nanoparticles: An active system for the reduction of aromatic nitro-compounds
Synthesis of carbon nitride supported highly dispersed ultrafine palladium nanoparticles has been reported for the reduction of aromatic nitro-compounds using hydrazine hydrate as a reducing agent. As a demonstration, the as-synthesized carbon nitride-palladium composite was shown to be a highly active and chemo-selective for the title reaction. Utilizing the optimized reaction conditions a set of aromatic nitro compounds have been converted to their corresponding amine derivatives with good to excellent yield ranging from 80% to 99%. The catalyst can be used for multiple times without affecting the catalytic performance and can also be stored for a long time at ambient condition maintaining the high catalytic efficiency.
Nandi, Debkumar,Siwal, Samarjeet,Choudhary, Meenakshi,Mallick, Kaushik
p. 31 - 38
(2016/06/09)

Preparation and characterization of Ni/mZSM-5 zeolite with a hierarchical pore structure by using KIT-6 as silica template: An efficient bi-functional catalyst for the reduction of nitro aromatic compounds
Ni/mZSM-5 and Ni/H-mZSM-5 were synthesized as hierarchical (micro/meso porous) ZSM-5 zeolites by an indirect template method for the first time. The resulting zeolite materials exhibited significantly enhanced diffusional properties in comparison to purely microporous zeolite materials. The structural and morphological characterization of the prepared catalysts was investigated using XRD, BET, atomic absorption spectroscopy, FT-IR, 27Al-MAS NMR, SEM, TEM, XPS and DRS-UV techniques. These hierarchical zeolites were used as acid-metal bi-functional heterogeneous catalysts for hydride transfer in the reduction of nitro aromatic compounds. In these reactions, NaBH4 was used as a reducing agent. Excellent yields at room temperature and very short reaction times in aqueous media conditions were obtained. Reusability experiments showed the excellent stability of Ni/mZSM-5 and Ni/H-mMZSM-5 and the catalysts could be reused 7 times without much loss of activity in reduction of nitro aromatic compounds. Surprisingly, the acid form of Ni/H-mZSM-5 showed much higher activity than that of Ni/mZSM-5. High yield, short reaction time, green solvent (water), room temperature, no by-product, the easy reusability of catalysts and the low amounts of catalyst required are some of the advantages of these catalysts.
Mazaheri, Omid,Kalbasi, Roozbeh Javad
p. 34398 - 34414
(2015/04/27)

peri-naphthalenediamines: XXXIV. 1,4,5,8-Tetrakis(dimethylamino)naphthalene: Alternative approaches to synthesis
New methods were proposed for synthesizing 1,4,5,8-tetrakis(dimethylamino)naphthalene with an overall yield of 4 to 12% to replace the known procedure ensuring an overall yield of 2%. Catalytic hydrogenation was shown to be inapplicable for preparation of polyaminonaphthalenes from nitro compounds having 3 or 4 nitro gruops in the α-positions. Nucleophilic amination of 1,5-dinitronaphthalene in the system NH2OH/NaOH/MeOH yields 1-amino-4-nitronaphthalene. The nitration of 1,5-bis(p-tolylsulfonylamino)-naphthalene leads to formation of 2,6-dinitro rather than 4,8-dinitro derivative, as it was believed formerly. This was confirmed by transformation of the latter into 1,2,5,6-tetrakis(dimethylamino)naphthalene. 3-Nitro, 2,6-dinitro, 2,6-diamino, and 2,4,6,8-tetranitro derivatives of 1,5-bis(dimethylamino)naphthalene, nitro and amino derivatives of 1,4,5-tris(dimethylamino)naphthalene, and 4,5-diamino-1,8-bis(methylamino)naphthalene were synthesized. By treatment with perchloric acid 1,4,5,8-tetrakis(dimethylamino)naphthalene was oxidized to 2,3-dihydroperimidinium salt.
Sorokin,Ozeryanskii,Pozharskii
p. 699 - 708
(2007/10/03)

Hydrogenation of isomeric dinitronaphthalenes on a palladium-containing anion exchanger
Liquid-phase hydrogenation of dinitronaphthalenes on the palladium-containing anion-exchange resin AV-17-8 (AV-17-8-Pd) and a Pd/C catalyst affords corresponding naphthylenediamines via the formation of nitronaphthylamines. The rate of the reaction depends on temperature, solvent nature, and the value of the effective charge on the oxygen atoms and the nitro group as a whole.
Voronin,Mazurova,Klyuev
p. 34 - 37
(2007/10/03)

peri-Naphthylenediamines 31.* Study of interconversions of 2,3-dihydroperimidines and 1,8-bis(dialkylamino)naphthaienes. Convenient synthesis of 1,2,2,3-tetramethyl-2,3-dihydroperimidine and a monoisopropyl analog of the "proton sponge"
Efficient procedures were developed for the two-step synthesis of 1,2,2,3-tetramethyl-2,3-dihydroperimidines and for the one-step synthesis of 1,3-dimethyl-2,3-dihydroperimidines starting from 1,8-diaminonaphthalenes. New possibilities of the use of 2,3-dihydroperimidinium salts in the synthesis of 1,8-bis(dialkylamino)naphthalenes ("proton sponges") containing the N-isopropyl group along with the N-methyl groups were demonstrated. The 1,1,2,2,3-pentamethyl-2,3-dihydroperimidinium cation exists in the acyclic iminium form responsible for its high reactivity.
Ozeryanskii,Filatova,Sorokin,Pozharskii
p. 846 - 853
(2007/10/03)

2-(Ethoxycarbonylmethyl)-1H-naphtho[1,8-de]-1,2,3-triazine anion: A new glycine enolate equivalent
The titled triazine can be alkylated with LDA and a variety of alkyl halides: Subsequent reduction with aluminium amalgam cleaves the naphthotriazine moiety to afford substituted α amino acids in excellent overall yields; the sequence defines a novel methodology that can be applied under non-acidic and largely non-aqueous conditions. (C) 2000 Elsevier Science Ltd.
Anilkumar,Chandrasekhar,Sridhar
p. 6665 - 6668
(2007/10/03)

Arylazo and poly(arylazo) dyes having at least one core radical selected from naphthyl or anthracyl and having at least one 2,3-dihydro-1,3-dialkyl perimidine substituent
Arylazo and poly(arylazo) dyes having at least one core radical selected from naphthyl or anthracyl and having at least one 2,3-dihydro-1,3-dialkyl perimidine substituent, a guest-host composition comprising a liquid crystal host solvent and the arylazo or poly(arylazo) dichroic dye, and a liquid crystal display comprising the guest-host composition, are disclosed.
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(2008/06/13)

Manufacture of aromatic amino compounds
A process for producing an aromatic amine comprises heating an aromatic sulfonate and a metal amide in liquid ammonia in a closed reactor at a temperature of at least 40° C to produce a metal arylamide and reacting the resultant metal arylamide with water or lower aliphatic alcohol to produce an aromatic amine.
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(2008/06/13)