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Naphthyl ammonium salt compound as well as preparation method and application thereof

A naphthylammonium salt and compound technology, which is applied in the field of purification of organic compounds, can solve the problem that the addition reaction product affects the quality of downstream products and the quality of 6-nitro-1,2-diazooxy-4-naphthalenesulfonic acid Can not meet the market demand and other problems, to achieve the effect of improving environmental compatibility, reducing process costs, and simple operation

Inactive Publication Date: 2018-07-13
JIUJIANG SHANSHUI TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Because the purity of addition reaction product can directly affect the quality of downstream product, even can cause the quality of final product 6-nitro-1,2-diazooxy-4-naphthalenesulfonic acid can not satisfy market demand, therefore, increase 1 -The quality of nitroso-2-naphthol is particularly important

Method used

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  • Naphthyl ammonium salt compound as well as preparation method and application thereof
  • Naphthyl ammonium salt compound as well as preparation method and application thereof
  • Naphthyl ammonium salt compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The naphthyl compound crude product shown in 2.55 kilograms of structural formula (I) is mixed with 12.75 kilograms of acetone, 1.9 kilograms of dicyclohexylamines, is stirred until reaction finishes, suction filtration, obtains 4.22 kilograms (yield 98.4%, HPLC purity 99.5%) structural formula The naphthyl ammonium salt compound shown in (III), the NMR data of the naphthyl ammonium salt compound shown in gained structural formula (III): 1 HNMR (500MHz, DMSO-d 6 ): δ8.08(d,1H), 8.01(d,1H), 7.77(t,1H), 7.56(t,1H), 7.43(d,1H), 7.05(d,1H), 6.89(br, 2H), 5.44 (br, 1H), 3.55 (m, 2H), 2.02-2.27 (m, 8H), 1.92 (br, 1H), 1.43-1.54 (m, 12H).

[0035] 4.22 kilograms (yield 98.4%, HPLC purity 99.5%) of naphthyl ammonium salt compound shown in structural formula (III) obtained through the above-mentioned process are mixed with 12.87 kilograms of water, add sodium hydroxide to adjust to system pH to 13, reclaim organic alkali to obtain an alkaline aqueous solution; the resulting al...

Embodiment 2

[0037] The naphthyl compound crude product shown in 2.55 kilograms of structural formula (I) is mixed with 12.75 kilograms of acetone, 1.01 kilograms of triethylamine, is stirred to the end of reaction, and suction filtration obtains 3.4 kilograms (yield 96.6%, HPLC purity 98.7%) structural formula ( III) shown in the naphthyl ammonium salt compound, the nuclear magnetic resonance spectrum data of the naphthyl ammonium salt compound shown in the gained structural formula (III): 1 HNMR (500MHz, DMSO-d 6 ): δ8.01~8.03(t,2H), 7.31~7.55(t,2H), 7.27(d,1H), 7.05(d,1H), 7.01(d,1H), 5.34(br,1H), 3.25(q,4H), 1.57(t,6H).

[0038] 3.4 kg (yield 96.6%, HPLC purity 98.7%) obtained through the above-mentioned process are mixed with 17 kg of water with the naphthyl ammonium salt compound shown in structural formula (III), and the system uses sulfuric acid to adjust the system pH=3 to obtain 2.43 kg ( Yield 94.2%, HPLC purity 99.1%) the naphthyl compound refined product shown in structural ...

Embodiment 3

[0040] The naphthyl compound crude product shown in 2.55 kilograms of structural formulas (I) is mixed with 7.65 kilograms of water, 1.01 kilograms of triethylamine, is stirred to the end of reaction, and suction filtration obtains 3.4 kilograms (yield 96.6%, HPLC purity 98.7%) structural formula ( III) shown in the naphthyl ammonium salt compound, the nuclear magnetic resonance spectrum data of the naphthyl ammonium salt compound shown in the gained structural formula (III): 1 HNMR (500MHz, DMSO-d 6 ): δ7.97~8.01(d,2H), 7.38~7.45(t,2H), 7.28(d,1H), 7.03(d,1H), 7.01(d,1H), 5.30(br,1H), 4.01(q,2H), 1.60(t,12H).

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Abstract

The invention discloses a naphthyl ammonium salt compound as well as a preparation method and application thereof. According to the preparation method disclosed by the invention, the characteristic that organic ammonium salt with a special structure is soluble in water while is insoluble or slightly soluble in an organic solvent is utilized; meanwhile, the organic ammonium salt is combined with inorganic acid or inorganic alkali to carry out acid-base exchange reaction; a compound shown as a structural formula I is purified at high yield and a time and is added with a reaction product so as toprovide powerful guarantee for industrially producing 6-nitro-1,2-diazoxy-4-naphthalene sulfonic acid with excellent quality. The preparation method of the naphthyl ammonium salt disclosed by the invention has the advantages of simple operation, no need of special production equipment, no special reaction process of potential safety hazards and extremely-high industrialization; meanwhile, all organic alkali can be recycled effectively so as to reduce the process cost and improve environmental compatibility of the method.

Description

technical field [0001] The invention relates to the technical field of purification methods of organic compounds, in particular to a class of naphthyl ammonium salt compounds and their preparation methods and applications. Background technique [0002] 6-nitro-1,2-diazooxy-4-naphthalenesulfonic acid, Abbreviated as "nitrate, 6-nitrate", it is an acid dye intermediate, widely used in the synthesis of medium black T, acid black 172, 194, etc. [0003] At present, 2-naphthol is used as the main starting material to obtain 1-nitroso-2-naphthol through nitrosation reaction; the obtained 1-nitroso-2-naphthol is obtained through addition-reduction-transposition reaction 1-nitroso-2-naphthol-4-sulfonic acid; 1-nitroso-2-naphthol-4-sulfonic acid is prepared by diazotization reaction to prepare 1,2-diazooxynaphthalene-4- Sulfonic acid; Finally, 1,2-diazooxynaphthalene-4-sulfonic acid was nitrated to produce 6-nitro-1,2-diazooxy-4-naphthalenesulfonic acid. [0004] Expressed in equ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/34C07C307/02C07C209/02C07C211/35C07C211/05
CPCC07C209/02C07C211/05C07C211/35C07C303/34C07C307/02
Inventor 邵玉田何亚奇付居标
Owner JIUJIANG SHANSHUI TECH
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