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DESCRIPTION SU443019

The method of obtaining 2,6-diisopropylphenol

The invention relates to a method for the preparation of 2,6-diisoproiylphenol, used as an

antioxidant in the food industry and as a reagent in organic chemistry.,

Pure 2,6-diisopropylphenol is known to be prepared by alkylation of / g-chlorophenol with isopropyl

alcohol in concentrated sulfuric acid, followed by catalytic dehalogenation with hydrogen in the
presence of rhenium nickel.

With the known method, it is necessary to use high pressure (29 at) for the catalytic
dehalogenation of 2,6-diisoproiyl-4-chloro-phenol, which is associated with the construction of a
special autoclave. In addition, the method is characterized by a relatively low synthesis yield: 2,6-
diiso11rople-4-chloro-phenol is formed in 9.3% yield, and 2, (5-d11nzopropylphenol itself, in 85%
yield, so that the total yield of the final product only 8%.

To simplify the technology of production and increase the yield of the target product, / g-
hydroxybenzoic acid is subjected to alkylation at a temperature not exceeding 40 ° C, followed by
exposure of the reaction mass at a temperature not exceeding 70 ° C. The resulting 3,5-
diisopropyl-4-ox-sibenzoic acid is heated to 70-140 ° C in triethylamine. The process can be
conducted in the presence of water-releasing substances.

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Alkylation of not phenol itself, but of i-hydroxybisoyzoic acid in the presence of acidic and (or)
water-borne substances eliminates the possibility of formation of by-products during exhaustive
alkylation, for example, the isomer of its 2,4-Dipisopropylphenol, after decarboxylation in the final
product. As a result of decarboxylation of the alkylation of 3,5-diisoprople-4-hydroxybenzoic acid at
250-280 ° C or its salts at 120-150 ° C, 2,6-diisopropnlpheiol is formed; decarboxcleaning is easier
to perform than dehalogenation, since it does not require high pressure, and preliminary
manufacture of the catalyst and special equipment (such as hydrogenation reactors). The
synthesis of 2,6-diisopropylpheiol proceeds in 78% yield, which accounts for 85% yield of
alkylation of ga-hydroxybenzoic acid and a yield of 92% decarboxylation. Oxybenzoic acid is three
times cheaper / g-chlorophenol.

Example. A 3 L round bottom flask equipped with a mechanical stirrer, thermometer, dropping
funnel and reflux condenser was charged with 1 L (1.83 kg) of sulfuric acid, the stirrer was turned
on and 70 ml of water was added in one go, then 276 g (2 mole) p-hydroxybenzoic acid. The flask
was equipped with a water bath, the contents of the flask were cooled to 20-25 ° C, and 240 g (4
mol) of isopropyl alcohol were added with a thin stream from the dropping funnel. The temperature
of the reaction mixture should not exceed 5 ° C. After addition of the total amount of isopropyl
alcohol (1 h), the temperature of the mixture is raised to 70 ° C and held for 3 hours until the
reaction is complete. By the end of this period, a crystalline precipitate gives off; the mass is
cooled to room temperature and filtered from sulfuric acid (filter made of fiberglass). The
precipitate is well sucked off, removed from the filter and, with stirring, is added in small portions in
10 l of water, stirred for 0.5 h and filtered on a suction filter. The filter cake is washed with water (5
times 500 ml) until the washings are neutral, then they are removed from the filter and dried in 20
air.

380 g of technical 3,5-diisopropyl-4-hydroxybenzoic acid (85%) are obtained, with a melting point
of 138-143 ° C, which is loaded into a three-liter flask equipped with a mechanical stirrer, a reflux
condenser 25 and a thermometer, 420 ml (305 g, 3 praying) triethylamine. The flask is slowly
heated in a glycerin bath. At 70-80 ° C, the mass dissolves, turn on the stirrer and raise the
temperature to 120-140 ° C. Rapid evolution of carbon dioxide bubbles is observed. After about 1
hour, de30 carboxylation is complete, as evidenced by the cessation of the release of carbon
dioxide bubbles. The flask was equipped with a Liebig cooler and triethylamine was distilled off
(i.e. cue. 89.5 ° C). Then the flask is connected to a vacuum pump and, gradually heating in an oil
bath, vacuum distillation is carried out, collecting a fraction from the so-called bale. 110-113 C (7
mm), 280 g (92%) of a yellow clear liquid are obtained which, according to gas chromatography,
contains 99.6% of 2,6-diisopropylphepol and has "2 1.5134 and dl? 0.955.

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The subject of the invention 1. The method of producing 2,6-dg1isopropylphenol using alkylation
with isopropyl alcohol in the presence of acidic catalysts with the subsequent isolation of the target
product by known methods, which are based on the fact that, in order to simplify the process
technology and increase the yield of the target product, g-hydroxybenzoic acid is subjected to
alkylation at a temperature not exceeding 40 ° C, followed by exposure of the reaction mass to a
temperature not exceeding 70 ° C, and the resulting 3,5-dig13o11ropyl-4-hydroxybenzoic acid is
heated to 70-140 ° C in triethane lamina.

2.
The method according to claim 1, characterized in that the process is conducted in the presence
of water-taking substances.

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