Vanillin ester condensed 1,3-butanediol and preparation method thereof

A technology of butanediol and vanillin, which is applied in the fields of essential oil/perfume, fat production, organic chemistry, etc., can solve the problems of blue purple, decomposition, etc., and achieve the effect of simple preparation method, easy operation, and high yield

Inactive Publication Date: 2013-07-10
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Vanillin and ethyl vanillin are widely used as raw materials for food and chemical flavors, but under the irradiation of ultraviolet rays, they will decompose in alcohol solution, showing the disadvantage of discoloration such as brown or blue purple

Method used

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  • Vanillin ester condensed 1,3-butanediol and preparation method thereof
  • Vanillin ester condensed 1,3-butanediol and preparation method thereof
  • Vanillin ester condensed 1,3-butanediol and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Using vanillin as raw material (0.30mol), toluene as solvent, the dosage is 100mL, add dropwise isobutyric anhydride (0.33mol) with a separatory funnel, dropwise for 1h, add Na 2 CO 3 Catalyst 0.02moL, react at 50°C for 2h. The reaction product was quenched with an equal volume of 15% NaOH solution, washed three times with saturated NaCl solution, the solvent was recovered by rotary evaporation, and fractions at 147-148°C (2.00kPa) were collected by vacuum distillation to obtain the product vanillin isobutyrate. The yield of vanillin isobutyrate is 95.9%, and after vacuum distillation, the total yield is 91.4%, and the purity is 98.5%. The reaction equation is:

[0030]

[0031] product of 1 H NMR data: 1.35~1.37 (d, J=6Hz, 6H, two methyl-CH 3 ), 2.79~2.93 (m, J=6Hz, 1H, -CH on methine), 3.91 (s, 3H, -CH on methoxy 3 ), 7.19~7.22 (dd, J=3Hz, 9Hz, 1H, H on the methoxy p-position benzene ring), 7.45~7.47 (d, J=9Hz, 1H, -OCOCH-o-position H on the benzene ring), 7....

Embodiment 2

[0040] Using vanillin as raw material (0.30mol), toluene as solvent, the dosage is 100mL, add acetic anhydride (0.33mol) dropwise with a separatory funnel, drop after 1h, add Na 2 CO 3 Catalyst 0.02moL, react at 50°C for 2h. The reaction equation is as follows:

[0041]

[0042] The reaction product was quenched with an equal volume of 15% NaOH solution, washed three times with hot saturated NaCl solution, the solvent was recovered by rotary evaporation, recrystallized from ethanol, and dried in vacuo to obtain the product acetylvanillin.

[0043] The resulting product is carried out infrared analysis (tablet method, v / cm -1 ): 3017.15, 2967.87, 2944.09, 2914.23 and 2847.03 (C-H stretching vibration peaks on methyl and benzene rings); 2754.13 (formaldehyde C-H stretching vibration peaks); 1755.50 (carbonyl C=O stretching vibration peaks); 1690.76 (aldehyde C = O stretching vibration peak); 1598.17, 1507.03 and 1470.94 (the stretching vibration peak of the C=C skeleton of...

Embodiment 3

[0050] Preparation of solid superacid catalyst: Weigh a certain amount of ZrOCl 2 wxya 2 O, add deionized water and keep stirring until completely dissolved. Continue to stir and slowly add concentrated ammonia water to precipitate the solution, adjust the pH to 8-9, stir for a while, and leave it for 24 hours to age. Repeated decantation, suction filtration, washing to no Cl - exists (with AgNO 3 solution testing). The precipitate was dried at 105 °C for 24 h, and ground to below 100 mesh. With 1mol / L H 2 SO 4 The solution was soaked for 24h, and the excess H was removed by filtration. 2 SO 4 solution. Dry at 105°C for 24h to obtain The solid superacid catalyst is placed in a desiccator after cooling. Roast at 450°C for 3h before use.

[0051] Preparation of solid superacid catalyst: Weigh a certain amount of ZrOCl 2 wxya 2 O and TiCl 4 , making n(Ti):n(Zr)=1:6, 1:3, 1:1, 3:1 and 6:1 in turn to obtain five kinds of composite solid superacid catalysts with ...

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Abstract

The invention discloses vanillin ester condensed 1,3-butanediol and a preparation method thereof. The preparation method comprises the following steps of: preparing vanillin ester; and preparing the vanillin ester condensed 1,3-butanediol. Compared with the conventional essences, the vanillin ester condensed 1,3-butanediol has the advantages that: the aroma of the vanillin ester condensed 1,3-butanediol is evaluated and analyzed by aroma evaluating experts, is pure powder aroma and thick, the aroma of 2-methoxy-4-(4-methyl-1,3-dioxane-2-yl)-phenylacetate and 2-methoxy-4-(4-methyl-1,3-dioxane-2-yl)-2-methyl phenylpropionate is the best, fresh, green, and durable, the aroma can be kept for 48-72 hours generally, and the 2-methoxy-4-(4-methyl-1,3-dioxane-2-yl)phenyl acetate and the 2-methoxy-4-(4-methyl-1,3-dioxane-2-yl)phenyl2-methylpropionate have development value and can be widely applied to various daily use chemical essences. In addition, the preparation method is simple, high in yield and easy to operate, has high practicability and can generate good economic benefit and social benefit.

Description

technical field [0001] The invention relates to a spice and a preparation method thereof, in particular to a vanillin ester 1,3-butanediol and a preparation method thereof. Background technique [0002] Perfume is a substance that can be smelled by the sense of smell or tasted by the sense of taste, and is the raw material for preparing essence. Perfume consists of two parts: natural perfume and synthetic perfume. Fragrances produced by chemical synthesis are called synthetic fragrances. At present, there are more than 5,000 kinds of synthetic fragrances in the world, and more than 3,000 kinds of commonly used products. Vanillin is a class of fragrances widely used, including vanillin, isovanillin, ethyl vanillin, vanillin ester and vanillin 1,2-propanediol acetal. These spices generally have a sweet, milky vanilla aroma and taste, and are widely used in food, beverage, cosmetic and tobacco industries. [0003] Vanillin (vanillin, 4-hydroxy-3-methoxybenzaldehyde, or p-hy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D319/06C11B9/00
Inventor 罗金岳刘飞
Owner NANJING FORESTRY UNIV
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