JPS6033095B2 - indane derivative - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides 1,1,3-trimethyl-3-(3,5-
(di-t-butyl-4-oxyphenyl)-6-t-butylindan-5-ol.

The compound of the present invention is effective as a stabilizer for vinyl chloride resin, polyethylene, polypropylene, polyurethane, polystyrene, rubber, and the like.

The compound of formula [1] of the present invention can be obtained by using, for example, a starting material containing p-isoprobenylphenol or a polymer thereof, converting this into a chain dimer, and then performing a cyclization reaction. 1,1,3-trimethyl-3-(4-oxyphenyl)
It can be produced by synthesizing -indan-5-ol and subsequently performing an alkylation reaction to introduce a t-butyl group.

Therefore, the chain dimer of p-isoprobenylphenol has the structure of It can be separated and easily isolated.

The catalyst used in the cyclization reaction of the chain doublet of p-isoprobenylphenol is a known acid catalyst used in the alkylation reaction of phenol, such as aluminum chloride, ferric chloride, Lewis acids such as stannic chloride and boron fluoride, protonic acids such as sulfuric acid, phosphoric acid, hydrochloric acid, perchloric acid, benzenesulfonic acid and toluenesulfonic acid, and solids such as silica alumina, activated clay, and cation exchange resins. Acid is used.

The amount of the above-mentioned catalyst used is usually in the range of 0.01 to 20% by weight, preferably 0.5 to 1% by weight, based on the total amount of raw materials.

During the reaction, aromatic hydrocarbons such as benzene, toluene/xylene, substituted aromatic hydrocarbons such as nitrobenzene, anisole, and chlorobenzene, methylene chloride, chloroform, carbon tetrachloride, ethylene dichloride,
Halogenated hydrocarbons such as tetrachloroethane are used.

The amount of these solvents used is usually 2 times the total amount of raw materials.
It is used in a range of 0 to 500% by weight, preferably 100 to 200% by weight. The reaction temperature in this reaction is usually in the range of 30 to 20 pi.

In the alkylation reaction of the cyclic dimer obtained by the cyclization reaction of the chain dimer of P-isoprobenylphenol, the cyclic dimer can be isolated even if the cyclic dimer is isolated from the cyclization reaction product. You can do it without it.

The catalyst and solvent used in the alkylation reaction can be the same as those used in the cyclization reaction, and the reaction temperature conditions are also the same. As the butylating agent used for t-butylation, halogenated butyl, secondary butyl alcohol, isobutylene, etc. can be used.
The reaction can be carried out under normal conditions or under pressure.

This will be further explained below with reference to Examples.

Example 1 Chain-like second base body of P-isoprobenylphenol with a purity of 90% by weight produced from P-isoprobenylphenol 10
(Hereinafter, "parts" indicate parts by weight), 5 parts of benzene, and 1 part of commercially available silica alumina were charged into a glass reactor, and heated under reflux for 3 hours at the boiling point.

After cooling, one portion of methanol was added, and the silica alumina catalyst was separated in the furnace. Methanol was distilled off from the furnace liquid, and the crystals precipitated by cooling were separated in the furnace and dried to obtain 8.2 parts of a cyclic dimer. 5 parts of the above cyclic dimer, 25 parts of benzene
and 1.5 parts of intestinal ion exchange resin Amberlyst-15 (trade name) were placed in a 200-ml flask and heated to 60°C.
While stirring in the afternoon, add isoptylene for 14 min.
The air was blown at a speed of 4 hours.

After the reaction is complete, the intestinal ion exchange resin is pierced in a furnace, the mother liquor is concentrated,
Subsequently, white crystals were precipitated by cooling. The dry weight of the crystals is 4. It was the $ section.

The melting point of this crystal was 179.5°C, and the results of nuclear magnetic resonance measurements were as follows. Nuclear magnetic resonance (6, skin) 1.05CH3 a 1.29CH3 b 1.38CH3 c 1.43CH3 d 1.62CH3 e 1.95CH3 f 2.17 〃 2.24 〃 2.45 〃 6.32 0-H g 6.91 〃 i 6.97 〃 j 4.450 days k 4. Team Figure 1 shows the nuclear bearish resonance spectrum, and Figure 2 shows the infrared absorption spectrum.

Example 2 P-isoprobenylphenol monomer 10.5%,
60.3% dimer, 15.6% trimer, 8.6% tetramer, 1.0% bentamer and more than 1 hexamer
．． A mixture of P-isoprobenylphenol and its polymer consisting of 5% (both weight %) 5. Anchorage, 10. Benzene and 1.0% cation exchange resin Amber Rinse.
5 (trade name) was placed in a 500ml flask, and the mixture was heated at a reaction temperature of 6-0 for 6 hours.

After cooling the reaction product, a mixture of white crystals and ion exchange resin was separated from the benzene layer.

The resulting mixture contained 28 parts of the cyclic dimer and 5 parts of the ion exchange resin.
The total amount of the mixture was 33 parts. 15 parts of this mixture and 5 parts of methylene chloride were charged into a flask, and while heating at a temperature of 40°C, isoptylene was secreted at a rate of 10 parts per minute. It was blown at a temperature of 50°C and allowed to react for 1 hour. After methylene chloride was removed from the reaction mixture, methanol was added to dissolve the product, and the mixture was filtered through an oven to separate the catalyst. Water was added to the furnace liquid and the resulting precipitate was separated from the furnace. This precipitate was recrystallized from benzene-methanol to give white crystals5. I got the $ part. The melting point of this crystal was 180 qo, and the measurement results of infrared absorption spectrum and nuclear magnetic resonance were the same as in Example 1.

[Brief explanation of the drawing]

FIG. 1 shows the 1,1,3-trimethyl-3-(3.
This figure shows a nuclear magnetic resonance spectrum of 5-di-t-butyl-4-oxyphenyl)-6-t-butylindan-5-ol, and FIG. 2 is an infrared absorption spectrum as well. Figure 2

Claims (1)

[Claims] 1 1.1.3-trimethyl-3-(3.5 −
di-t-butyl-4-oxyphenyl)-6-t-butylindan-5-ol.