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Method for preparing 3-methylamino-4-nitrophenoxyethanol

A technology of nitrophenoxyethanol and methylamino group is applied in the field of preparation of 3-methylamino-4-nitrophenoxyethanol, can solve the problems of high solvent tetrahydrofuran price, difficult recovery, low yield and the like, and achieves a reduction in The effect of recovering operating costs, reducing solvent costs, and high yield

Active Publication Date: 2014-11-05
ZHEJIANG DINGLONG TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] This method has the problems of high solvent tetrahydrofuran price, difficult recovery, and low yield.

Method used

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  • Method for preparing 3-methylamino-4-nitrophenoxyethanol
  • Method for preparing 3-methylamino-4-nitrophenoxyethanol
  • Method for preparing 3-methylamino-4-nitrophenoxyethanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Preparation of 3-methylamino-4-nitrobenzene chloride

[0037]Add 50g (0.260mol) of 2,4-dichloronitrobenzene and 150g of methanol into a four-neck flask, stir and raise the temperature to reflux, add 47.6g (0.613mol) of 40w% methylamine aqueous solution dropwise, and the dropping time is controlled After 1h, after the dropwise addition, keep the reflux temperature and react for 15h, the reaction solution is orange transparent liquid, slowly cool down to 10°C by passing through ice-salt water, keep warm and crystallize for 30min, then filter and dry to obtain orange 3-methylamino-4- The crude product of nitrochlorobenzene was beaten with 60g of methanol, filtered and dried at 70°C to obtain 34.5g of orange intermediate 3-methylamino-4-nitrochlorobenzene, the HPLC purity was 99.65%, and the yield was 71.00 %.

[0038] (2) Preparation of crude 3-methylamino-4-nitrophenoxyethanol

[0039] Add 5.5g NaOH (the first batch of alkali) and 105g (1.692mol) ethylene glycol int...

Embodiment 2～4

[0043] The same operation as that in step (1) of Example 1 is adopted, except that different amounts of methanol, methylamine aqueous solution, different concentrations of methylamine aqueous solution and different reaction times are used. The data obtained in Examples 1 to 4 are shown in Table 1:

[0044] Table 1

[0045]

[0046] Can find out according to table 1, adopt the methyl alcohol of different consumption, methylamine aqueous solution, methylamine aqueous solution of different concentration and different reaction time, all can have obvious effect to the purity and the yield of 3-methylamino-4-nitrochlorobenzene Impact, thereby affecting the purity and yield of the final product 3-methylamino-4-nitrophenoxyethanol.

Embodiment 5～8

[0048] Adopt and embodiment 1 step (2) in same operation, difference is to select the ethylene glycol of different consumption, NaOH and different reaction time, the data obtained in embodiment 1 and embodiment 5~8 are as shown in table 2:

[0049] Table 2

[0050]

[0051] Wherein, NaOH is one-time addition among the embodiment 6, and other embodiments are to add in batches.

[0052] Can find out according to table 2, adopt the ethylene glycol of different consumption, NaOH and different reaction time, all can have obvious influence to the purity and the yield of 3-methylamino-4-nitrophenoxyethanol crude product, thereby influence final The purity and yield of the product 3-methylamino-4-nitrophenoxyethanol.

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Abstract

The invention relates to a method for preparing 3-methylamino-4-nitrophenoxyethanol. The method comprises the steps of performing methylamination reaction by using 2,4-dichloronitrobenzene as a raw material and using methanol as a solvent to obtain 3-methylamino-4-nitrochlorobenzene, performing nucleophilic substitution with a sodium hydroxide (or other alkaline matter) solution of ethylene glycol to substitute the remaining other chlorine group so as to obtain crude 3-methylamino-4-nitrophenoxyethanol, and performing re-crystallization to obtain high-purity 3-methylamino-4-nitrophenoxyethanol. The process of preparing the 3-methylamino-4-nitrochlorobenzene intermediate through a one-step method replaces a two-step method process of preparing the intermediate through high pressure ammonolysis of 2,4-dichloronitrobenzene and N-methylation reaction; in addition, methanol is adopted in the one-step method to replace a tetrahydrofuran solution, so that the purposes of reducing the recovery cost and reducing the cost of the solvent are achieved; the method has the characteristics of conventional equipment, simplicity in operation, cheap and readily available raw materials, low cost, high yield and the like.

Description

technical field [0001] The invention relates to a preparation method of nitro dyes, in particular to a preparation method of 3-methylamino-4-nitrophenoxyethanol. Background technique [0002] In recent years, with people's pursuit of fashionable life, the proportion of hair dyeing is increasing day by day. However, the direct color-forming component in traditional hair dyes is p-phenylenediamine, which is a carcinogen and is prone to allergies when in contact with the skin. It is not suitable for long-term frequent use. Therefore, it is urgent to develop a low-toxicity , Hypoallergenic hair colorant. [0003] 3-Methylamino-4-nitrophenoxyethanol, a nitro dye, CAS No.59820-63-2, it is a direct hair coloring agent, which can be used in 21 different color hair dyes, using Concentrations as high as 0.15%. When applied to the coloring of keratin fibers, which are contacted by the cuticle and the remaining color is attached to the hair, not to the normal skin. Therefore, there ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/84C07C213/06C07C211/52C07C209/10
Inventor 肖庆军汪小华胡晓峰刘俊芳于尚琴
Owner ZHEJIANG DINGLONG TECH
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