SU461498A3 - The method of obtaining acylhydrazones or their salts - Google Patents

Description

A method is proposed for producing new compounds that may find use as stabilizers for polymers.

The use of the reaction of the hydrazides of acids with ketones known in organic chemistry as applied to 2,2,6,6-tetramethylpiperidone-4 made it possible to obtain new acyl hydrazones, as well as their salts.

The proposed method of producing acylhydrazones of the general formula

,

 w

ABOUT

R.

where A is methylene, ethylene or isopropylene;

R and R2 are the same or different and denote a linear or branched alkyl group with carbon atoms;

n is O or 1,

or their salts is that the compound of the general formula

but (A, G C-№1-W ,.

one:

where A, RI, R2 and tt have the indicated meanings, are reacted with 2,2,6,6-tetramethylniperidone-4, followed by isolation of the desired product as a base or

transferring it to salt in a known manner. The reaction is carried out by heating both components of the reaction together, preferably in an inert solvent under the reaction conditions, and in an aliphatic

an alcohol, such as ethanol, in an aromatic hydrocarbon (toluene) or dialkyl ether (diethyl ether). The reaction is carried out at the boiling point of the mixture, using approximately equivalent amounts of each

component. Upon completion of the reaction, the product can be cleaned by conventional methods.

Examples of salts of acyl hydrazones are salts of inorganic acids such as phosphates, carbonates, sulfates, acid chlorides, and

organic acid salts such as citrates, acetates, stearates, maleates, oxalates and benzoates.

Example 1. A mixture of 68.4 parts of hydrazine P- (3,5-di-g 1g-butyl-4-hydroxyphenyl) peronic acid and 31 parts of triacetonamine in 150 parts of methanol is heated at the boiling point for 12 hours. After removal of methanol by distillation under reduced pressure, a solid remains, which is recrystallized from petroleum ether,

48 I. 2.2, b, 6-tetraethylpiperndi1Shl-4- (3 (3,5-di-greg-butyl-4-hydroxyphenyl) -propioiylhydrazone, mp 127 ° C.

Found,%: C 72,12; H 10.02; N 9.60.

SgN.DZO, Calculated,%: C 72.80; H 10.01; N 9.79.

Example 2 A mixture of 13.2 parts of hydrazine | 3 (3,5-diisopropyl-4-hydroxyphenyl) propionic acid and 15.50 parts of triacetonamine in 150 parts of methanol is heated at boiling point for 12 hours. After removal of methanol by distillation under reduced pressure, a solid remains, which is recrystallized from petroleum ether to give 5.30 parts of 2,2,6,6-tetramethylpiperidinyl4- | 3- (3,5-diisopropyl-4-hydroxyphenyl) propionyl hydrazone in the form of white needles, so pl. 25127 ° С

Found,%: C 71.96; H 9.96; N 10.28.

С24Нз9МзО2.

Calculated, o / o: C 71.78; H 9.79; N 10.46.

Example 3. A mixture of 7.30 parts of hydrazide (3- (3,5-di-bluoro-butyl-4-hydroxyphenyl) propionic acid and 7.75 parts of triacetonamine in 120 ml of methanol is heated at boiling point for 12 hours. After removal of methanol by distillation under reduced pressure, a solid remains, which is recrystallized from petroleum ether to give 2.0 parts of 2,2,6,6-tetramethylpiperidinyl-4-p (3,5-di-sec-butyl-4- hydroxyphenyl) perionylhydrazone as a white solid, mp 142-143 ° C.

Found,%: C 72.86; H 10.03; N 9.87.

С2бН4зНзО2.

Calculated,%: C, 72.68; H 10.09; N 9.78.

Example 4. A mixture of 12.50 parts of P- (3-greg-butyl-4-hydroxy-5-methylphenyl) propionic acid hydrazide and 15.50 parts of triacetonamine in 150 parts of methanol is heated at a kinenium temperature for 12 hours. After removal of methanol by distillation under reduced pressure, a solid remains, which is recrystallized from methyl alcohol to obtain 10.50 parts of 2,2,6,6-tetramethylpiperidinyl-4-p- (3-g / e-butyl-4-oxime -5-methylphenyl) propionyl hydrazone in the form of a white solid, so pl. 187-188 ° C.

Found,%: C 71.10; H 9.66; N 10.56.

С2зНз7НзО2.

Calculated,%: C 71.28; H 9.62; N 10.84.

Example 5. A mixture of 3.96 parts of α-hydrazide 3,5di-greg-butyl-4-hydroxybenzoic acid and 3.10 parts of triacetonamine is heated at boiling point in 60 parts of ethyl alcohol for 17 hours. Removal of ethyl alcohol (solvent) by distillation under reduced pressure yields a white solid, which is washed with ether to remove excess triacetonamine and crystallized from ethyl alcohol, yielding 1.80 parts of 2,2,6,6-tetramethylcyperidyl-4- (3 , 5di-t / 7g-butyl-4-hydroxybenzoyl) hydrazone, m.p. 174-175 ° C.

Example 6. Analogous to Example 7, the method B was added using a reaction of 4.90 parts of 3,5-dimethyl-4-hydroxybenzoic acid hydrazide and 9.30 parts of triacetonamine in 150 parts of methyl alcohol, to give 6.90 parts of 2.2 , 6,6-tetramethylpiperidinyl4- (3,5-dimethyl-4-hydroxybenzoyl) hydrazone, m.p. 128-129 ° C.

Subject invention

The method of producing acylhydrazones of the general formula

-y--

I0 - (-NH-N - (NH

Z d

where A is methylene, ethylene or isopropylene;

RI and R2 are the same or different and denote a linear or branched alkyl group with 1-6 carbon atoms;

is O or 1,

or salts thereof, characterized in that the compound of the general formula

(A) „- CNH-NHv

where A, RI, R2 and p have the indicated meanings, are reacted with 2,2,6,6-tetramethylpiperidone-4, followed by isolation of the desired product as a base or by salting it in a known manner.