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Method for catalytic synthesis of 3,5-ditertbutyl-4-hydroxybenzoic acid n-hexadecyl ester by acidic ionic liquid

An acidic ionic liquid, hydroxybenzoic acid technology, applied in the chemical industry, can solve the problems of complex process flow, strong corrosiveness of raw materials, easy generation of by-products, etc., and achieve the effects of simplified process, high catalytic efficiency and low production cost

Active Publication Date: 2018-06-29
兰州精细化工有限责任公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a kind of acidic ionic liquid catalytic synthesis method of 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl, to solve the complex technical process of the existing method, the raw material is very corrosive, easy to By-products are produced, and post-processing is troublesome, causing pollution to the environment

Method used

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  • Method for catalytic synthesis of 3,5-ditertbutyl-4-hydroxybenzoic acid n-hexadecyl ester by acidic ionic liquid
  • Method for catalytic synthesis of 3,5-ditertbutyl-4-hydroxybenzoic acid n-hexadecyl ester by acidic ionic liquid

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Experimental program
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Effect test

Embodiment 1

[0019] Weigh 3,5-di-tert-butyl-4-hydroxybenzoic acid 31.25g (0.125mol), n-hexadecanol 30.25g (0.125mol), ionic liquid [HS0 3 -pmim] + [HS0 4 ] - 0.01mo1; first add the weighed n-hexadecanol into a three-necked flask equipped with a stirrer, a thermometer, and a reflux condenser, raise the temperature until the n-hexadecyl alcohol is completely dissolved, and then add the weighed 3,5-di-tert-butyl Base-4-hydroxybenzoic acid and ionic liquid catalyst were stirred, continued to heat up to 120° C., utilized vacuum dehydration (vacuum degree was -0.05 MPa), and kept the temperature for 5 hours. Use phase chromatography (HPLC method) to monitor when the reaction reaches the end point, cool the reaction system to 70°C, let it stand for stratification, the lower layer is an ionic liquid, and repeat the application after separation; the upper layer is cooled to 70°C, a large amount of crystallization appears after adding methanol solution, filter The obtained filter cake is the targ...

Embodiment 2

[0021] Weigh 3,5-di-tert-butyl-4-hydroxybenzoic acid 31.25g (0.125mol), n-hexadecanol 30.25g (0.125mol), ionic liquid [HS0 3 -pmim] + [pTSA] - 0.01mo1; first add the weighed cetyl alcohol into a three-necked flask equipped with a stirrer, a thermometer, and a reflux condenser, raise the temperature until the cetyl alcohol is completely dissolved, and then add 3,5-di-tert-butyl-4 -Hydroxybenzoic acid and ionic liquid catalyst are stirred, continue to heat up to 160 ℃, utilize vacuum dehydration (vacuum degree is-0.02MPa), heat preservation reaction 3 hours; Monitor reaction with phase chromatography (HPLC method) when reaching end point, cool down to Stand at 70°C for stratification, the lower layer is the ionic liquid, which can be used repeatedly after separation; the upper layer is added with methanol solution, a large number of crystals appear, and the filter cake obtained by filtration is the target product. The esterification rate was 98.6%, and the yield was 90.0%.

Embodiment 3

[0023] Weigh 3,5-di-tert-butyl-4-hydroxybenzoic acid 31.25g (0.125mol), n-hexadecanol 30.25g (0.125mol), ionic liquid [HS0 3 -pPy] + [HS0 4 ] - 0.019mol; First add the weighed n-hexadecanol into a three-necked flask equipped with a stirrer, a thermometer and a reflux condenser, raise the temperature until the n-hexadecanol is completely dissolved, then add 3,5-di-tert-butyl-4 -Hydroxybenzoic acid and ionic liquid catalyst, continue to stir and heat up to 100 ℃, utilize vacuum dehydration (vacuum degree is-0.08MPa), heat preservation reaction 8 hours; Stand at 70°C for stratification, the lower layer is the ionic liquid, which can be used repeatedly after separation; the upper layer is added with methanol solution, a large number of crystals appear, and the filter cake obtained by filtration is the target product. The esterification rate was 98.0%, and the yield was 90.5%.

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Abstract

The invention discloses a method for catalytic synthesis of 3,5-ditertbutyl-4-hydroxybenzoic acid n-hexadecyl ester by acidic ionic liquid, and belongs to the field of chemical industry. By adoption of the method, the problems of complex process flow, troublesome aftertreatment and pollution to the environment of the existing method are solved. The method comprises the following steps: by utilizing acidic dual-core functional ionic liquid as a catalyst, and adopting 3,5-ditertbutyl-4-hydroxybenzoic acid and n-hexadecyl alcohol as raw materials, utilizing vacuumization for dewatering, controlling reaction temperature to be 100-160 DEG C and reacting for 3-8 hours, after reaction is ended, cooling, and standing for layering, separating out a lower layer namely ionic liquid to repeatedly usethe same; pouring an upper layer into methanol solution to generate a large amount of crystals, and filtering to obtain filter cakes, namely a target product. The method disclosed by the invention adopts the ionic liquid as a pollution-free catalyst and shows the advantages of high efficiency, high selectivity, mild reaction condition, simple and controllable effects, environment friendliness, high catalytic efficiency, simple aftertreatment and the like in various acid catalytic reactions.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a method for catalyzing and synthesizing n-hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate by ionic liquid. Background technique [0002] 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl ester (trade name: UV-2908) is an excellent hindered phenolic ultraviolet absorber with low volatility, small coloring and good chemical stability , acid and alkali resistance, can absorb ultraviolet light with a wavelength in the range of 290-400nm, convert the absorbed energy into harmless light or heat and release it, inhibit the early initiation stage in the polymer degradation process, and achieve the effect of photostability , suitable for polyolefin plastics such as PP and PE. During the esterification reaction of 3,5-di-tert-butyl-4-hydroxybenzoic acid and n-hexadecanol, the selectivity of the reaction varies greatly with different catalysts, and the by-product is formed aft...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/84B01J31/02
CPCB01J31/0285B01J2231/49C07C67/08C07C69/84
Inventor 霍利春何开宇解平和刘云利李清芳巨雪霞王开鑫董成伟
Owner 兰州精细化工有限责任公司
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