Novel method for preparing 1,3-dihydroxy acetone from glycerol

A technology of dihydroxyacetone and glycerin, which is applied in the first field, can solve the problems of long reaction time and poor selectivity, and achieve the effects of large market competitiveness, simple process, high selectivity and yield

Active Publication Date: 2009-04-22
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen that the direct oxidation of glycerin is difficult to change the sho

Method used

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  • Novel method for preparing 1,3-dihydroxy acetone from glycerol
  • Novel method for preparing 1,3-dihydroxy acetone from glycerol
  • Novel method for preparing 1,3-dihydroxy acetone from glycerol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Step (1): Add 0.6 g of p-toluene sulfonic acid, 58.0 g of glycerin, 61.0 g of benzaldehyde, and 100 ml of benzene into a 250 ml round bottom flask equipped with a condenser and a water separator, heat and stir, and condense and reflux. The reaction temperature was controlled at 130°C, and the reaction time was 2 hours. The reaction solution was washed with water, dried with anhydrous potassium carbonate, and distilled under reduced pressure (to recover benzene), and then crystallized in a mixed solution of benzene and petroleum ether (volume ratio 1:1) at -10°C to obtain 12.4 g of glycerol benzaldehyde acetal ether. The yield was 12.3%. The recovered mother liquor of benzene and acetal crystallization is kept for use.

[0043] Step (2): Add 1 mol of chromium trioxide slowly to 2 mol of pyridine, and control the reaction temperature below 40°C. Under constant stirring, yellow pyridine chromium oxide precipitates will be produced. Continue to stir, and the yellow precipitate ...

Embodiment 2

[0046] Step (1): Add 1ml 98% sulfuric acid, 58g glycerin, 61g benzaldehyde (with an excess of 6% benzaldehyde) and 100ml acetal crystal mother liquor in a 250ml round bottom flask equipped with a condenser and a water separator, and heat and stir. , Condensate to reflux, reaction temperature 130°C, reaction time 6 hours. After the completion of the reaction, the reaction solution was washed with water, dried with anhydrous potassium carbonate, distilled under reduced pressure (recovered benzene) and crystallized in a mixed solution of benzene and petroleum ether (1:1) at -10°C to obtain glycerol benzaldehyde acetal ether 21.6 g, the yield was 21.4%. The recovered benzene and crystallization mother liquor are kept for use.

[0047] Step (2): Quickly add 100g of chromium trioxide to 6mol / L hydrochloric acid (containing 1.1molHCl) (adding while stirring), after 5 minutes, cool the homogeneous solution to 0°C to obtain a reddish brown liquid, which is filtered and removed under normal...

Embodiment 3

[0050] Step (1): In a 250ml round bottom flask equipped with a condenser and a water trap, add 6g of D072 strong acid cation exchange resin, 58.0g of glycerin, 61.0g of benzaldehyde (with an excess of 6% benzaldehyde), and 100ml of benzene. Heating and stirring, condensing and refluxing, the water produced by the reaction and the azeotroping agent benzene are azeotropically evaporated. The reaction temperature was controlled at 110°C, and the reaction time was 6 hours. After the completion of the reaction, the reaction solution was washed with water, dried with anhydrous potassium carbonate, and distilled under reduced pressure (to recover benzene). Then, 18.0 g of glycerol benzaldehyde acetal ether was obtained in a mixed solution of benzene and petroleum ether (1:1) at -10°C. The yield is 17.9%. The recovered mother liquor of benzene and acetal crystallization is kept for use.

[0051] Step (2): Add 50 g (0.5 mol) of chromium trioxide in a beaker containing 20 mL of water. After...

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Abstract

The invention discloses a new method for preparing 1, 3-dihydroxyacetone from glycerol, which comprises the following steps: (1) acetalation reaction, which is to perform acetalation reaction of the glycerol and benzaldehyde in the presence of a water-carrying agent and under the action of an acid catalyst A so as to obtain glycerol benzaldehyde acetal ester having a structure as shown in the formula (I); (2) oxidation reaction, which is to oxidize the glycerol benzaldehyde acetal ester in an organic solvent and under the action of an oxidizer so as to obtain 5-carbonyl-2-phenyl -1, 3-dioxane having a structure as shown in the formula (II); and (3) hydrolysis reaction, which is to hydrolyze the obtained 5-carbonyl-2-phenyl -1, 3-dioxane in the presence of an acid catalyst B so as to prepare a 1, 3-dihydroxyacetone dimer having a structure as shown in the formula (III). The synthetic route of the method uses the glycerin as a raw material, thus both the selectivity and the yield are higher than that by a method of direct oxidation, the target product is simple and convenient to separate, and the product purity can reach 99 percent; and compared with the prior art, the synthetic route of the method has stronger market competitiveness.

Description

(1) Technical field [0001] The invention relates to a preparation method of 1,3-dihydroxyacetone. (2) Background technology [0002] In recent years, the continuous expansion of oleochemicals, especially biodiesel, has caused a serious oversupply of its by-product glycerin, and its price has fallen sharply. The development of downstream products using glycerin as a raw material can not only solve the problem of excess glycerin, but also Can reduce the production cost of biodiesel. 1,3-Dihydroxyacetone (DHA, dihydroxyacetone) is an important pharmaceutical intermediate, chemical raw material, food additive, and cosmetic sunscreen ingredient. It can also be used as an antiviral agent. For example, it can kill 51%-100% of chicken plague virus in egg embryo culture; it can also be used for preservation and preservation of fruits and vegetables, aquatic products, and meat products; there are still many other uses in active Under research and development. [0003] At present, the relat...

Claims

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Application Information

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IPC IPC(8): C07D319/12B01J31/08
Inventor 王建黎余健儿计建炳
Owner ZHEJIANG UNIV OF TECH
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