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A kind of preparation method of high-purity 2-methyl-4-heptafluoroisopropylaniline

A technology of heptafluoroisopropylaniline and methylaniline, which is applied in the field of preparation of high-purity 2-methyl-4-heptafluoroisopropylaniline, can solve the problems of zinc powder pollution, inability to promote industrialization, and high production costs. To achieve the effects of increased selectivity, great implementation value and social and economic benefits

Active Publication Date: 2019-03-05
QUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Patent US2002 / 198399 and Indian Pat.2010DE00753 report the synthesis of 2-methyl-4-heptafluoroisopropylaniline through zinc powder promotion or the reaction of 2-methylaniline and heptafluoroiodopropane through light radiation, and the cost of heptafluoroiodopropane High, and zinc powder will cause greater pollution
However, preparation by photoradiation requires special equipment.
CN1257861A has reported the synthesis of 2-methyl-4-heptafluoroisopropylaniline by the reaction of 2-methylaniline and heptafluoroiodopropane promoted by hydrosulfite, but the high cost of heptafluoroiodopropane makes the production cost higher, so that it cannot Industrialization promotion
When repeating the process, consistent with the patented process, we found that the above process produces by-products 2-methyl-6-heptafluoroisopropylaniline (>1%) and 2-methyl-4-hexafluoroisopropylaniline (>3%)

Method used

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  • A kind of preparation method of high-purity 2-methyl-4-heptafluoroisopropylaniline
  • A kind of preparation method of high-purity 2-methyl-4-heptafluoroisopropylaniline
  • A kind of preparation method of high-purity 2-methyl-4-heptafluoroisopropylaniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]Three-necked flask was added 10 grams o-toluidine (93mmol) and 200ml water, stirred. Add 11.8 g of sodium carbonate (111 mmol, 1.2 eq), 3.15 g of tetrabutylammonium bisulfate (9.3 mmol, 0.1 eq), 0.5 g of nitromethane (9.3 mmol, 0.1 eq) and heptafluoroisopropylbromomethyl tert-butyl ether solution [containing 25.4 g of heptafluoroisopropyl bromide (102 mmol, 1.1 equivalents) and 200 ml of methyl tert-butyl ether, stored at 0°C in advance], after stirring for 2 minutes, add 17.5 g of hydrosulfite (111 mmol, 1.2 equivalent). React overnight. The organic phase was separated, the aqueous layer was extracted with 20 ml of methyl tert-butyl ether, and the organic layers were combined. Washing with water and 5% sodium carbonate successively. The organic phase was dried with anhydrous sodium sulfate, filtered, and the organic solvent was distilled off to obtain 30 g of crude product, with a crude yield of >100%. Carry out gas phase analysis to crude product, the result is as ...

Embodiment 2

[0037] Three-necked flask was added 10 grams o-toluidine (93mmol) and 200ml water, stirred. Add 11.8 g of sodium carbonate (111 mmol, 1.2 eq), 3.15 g of tetrabutylammonium bisulfate (9.3 mmol, 0.1 eq), 2.5 g of p-nitrotoluene (18.6 mmol, 0.2 eq) and heptafluoroisopropyl bromide Methyl tert-butyl ether solution [containing 25.4 grams of heptafluoroisopropyl bromide (102 mmol, 1.1 equivalents) and 200 ml of methyl tert-butyl ether, stored at 0 ° C in advance], after stirring for 2 minutes, add 17.5 grams of hydrosulfite (111 mmol, 1.2 equivalent). React overnight. The organic phase was separated, the aqueous layer was extracted with 20 ml of methyl tert-butyl ether, and the organic layers were combined. Washing with water and 5% sodium carbonate successively. The organic phase was dried with anhydrous sodium sulfate, filtered, and the organic solvent was distilled off to obtain 30 g of crude product, with a crude yield of >100%. Distillation under reduced pressure yielded 25...

Embodiment 3

[0039] The basic operation is the same as in Example 2, except that the reaction catalyst is 2.5 grams of p-nitroaniline (18.6 mmol, 0.2 equivalents). Distillation under reduced pressure yielded 24.3 g of product with a yield of 95%. Carry out gas phase analysis to the product, the result is as follows: o-methylaniline 0.8%; 2-methyl-4-heptafluoroisopropylaniline 98%; 2-methyl-6-heptafluoroisopropylaniline 0.9%; 2- Methyl-4-hexafluoroisopropylaniline 0.08%.

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Abstract

The invention relates to a preparation method for high-purity 2-methyl-4-heptafluoroisopropylaniline. A catalyst is added into a reaction system for stabilizing perfluoro free radicals in the reaction system and controlling the production of an ortho-position and a defluorinated isomer, wherein the catalyst is a fatty or aromatic nitro compound; the structural formula of the catalyst is as shown in the specification, wherein R1, R2, R3, R4, R5 and R6 are hydrogen atoms, C1-20 alkyls, C3 to 6 naphthene groups, halogenated C1-20 alkyls, C1-20 alkoxy groups, halogenated C1-20 alkoxy groups, C1-20 alkyl sulphanyls, alkoxyl groups C1-20, hydroxyls, hydroxyl C1-20 alkyls, amino C1-20 alkyls, phenyls, phenyls with one to five substituent groups, phenoxyls, phenoxyls with one to five substituent groups, benzyls, benzyls with one to five substituent groups or C2-20 perfluoroalkyl groups; the substituent groups R2 to R6 are the same or different on a benzene ring. Compared with the prior art, after the catalyst is added into the reaction system; the selectivity of a reaction is effectively improved; impurities are effectively controlled. The preparation method has a great implementation value and social and economic benefits.

Description

technical field [0001] The invention relates to a preparation method of high-purity 2-methyl-4-heptafluoroisopropylaniline. Background technique [0002] 2-Alkyl-4-heptafluoroisopropylaniline has a wide range of applications in the fields of pesticides, medicines, coatings, rubber and materials. Among them, 2-methyl-4-heptafluoroisopropylaniline is the key intermediate of flubendiamide. However, the main by-products in the production process are 2-methyl-6-heptafluoroisopropylaniline and 2-methyl-4-hexafluoroisopropylaniline. Wherein 2-methyl-4-hexafluoroisopropylaniline and 2-methyl-4-heptafluoroisopropylaniline have similar physical and chemical properties and are difficult to remove by simple distillation or recrystallization. For the safety of subsequent products, commercial products require its content <0.2%. Therefore, it is of great economic value to develop a safe and low-cost method for preparing high-purity 2-alkyl-4-heptafluoroisopropylaniline. [0003] Pat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/68C07C209/86C07C211/52B01J31/02
CPCB01J31/0235B01J31/0238B01J2231/4205C07C209/68C07C209/86C07C211/52
Inventor 葛承胜翁将森周强王树华
Owner QUZHOU UNIV