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Theobromine production process

A technology of theobromine and solvent, applied in the field of preparation and refining of theobromine, which can solve problems such as toxicity, flammability, and difficulty in removal

Inactive Publication Date: 2010-11-24
PERRIGO TRADING (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, because methyl chloride is extremely flammable and toxic, the use of reagents such as methyl chloride is disadvantageous
Sulfolane, for example, has a very high boiling point of 284°C, so it is difficult to remove residual traces of this solvent from the final product
[0026] The people such as Niegel described in the patent DD 222026 (East Germany) by 3-methylxanthine and dimethyl sulfate in the mixture of water and methanol for example, react synthesis theobromine (embodiment 1) under the presence of potassium carbonate, with Obtain 73% yield of theobromine, but the patent has no record about the purity of the obtained theobromine

Method used

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Examples

Experimental program
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example 2

[0086] This example demonstrates the preparation of theobromine in a mixture of acetone and water in the presence of sodium bicarbonate.

[0087] 16.6 g of 3-methylxanthine (0.1 mol) and 100 ml of acetone were mixed in a 500 ml four-necked reaction vessel equipped with a mechanical stirrer, and 20 ml of water were added. 36 g of sodium bicarbonate were added with stirring and heated to a temperature of 55-60°C. 20 g of dimethyl sulfate were added dropwise over 3.5 hours and kept stirring at 55-60° C. for half an hour. Then, acetone is distilled off and recovered. 50 ml of water were added and the reaction vessel was heated to 80°C. Then, 32% hydrochloric acid was slowly added to the mixture, and the measured pH was in the range of 5-6. The mixture was cooled to 25°C, whereby the solid formed was obtained by precipitation, washed with water and dried at 70°C; 15.7 g of theobromine were obtained in 87% yield with a purity of 99.9% by HPLC.

example 3

[0089] This example demonstrates the preparation of theobromine in the presence of sodium carbonate in acetone.

[0090] In a 500ml four-necked reaction vessel equipped with a stirrer, 3-methylxanthine disodium salt (63g), acetone (304ml) and sodium carbonate (19.1g) were added with continuous stirring. The mixture was slowly heated to about 55°C. Dimethyl sulfate (60 g) was added dropwise over 4 hours. Then, the reaction was kept at 55°C for half an hour. Acetone was distilled off at normal pressure and water (50ml) was added. The product solution was neutralized to a pH of around 5 using 32% hydrochloric acid at 30°C. Then, the solution was filtered, washed with warm water (15 ml) at 40°C, filtered under reduced pressure to remove water, and dried at 70°C to obtain crude theobromine in 86.7% yield.

example 4

[0092] This example demonstrates the preparation of theobromine in acetone in the presence of sodium carbonate.

[0093] In a 500ml four-necked reaction vessel equipped with a stirrer, 3-methylxanthine disodium salt (63g), acetone (304ml) and sodium carbonate (19.1g) were added under stirring. The mixture was heated to 55°C and dimethyl sulfate (60 g) was added dropwise over 3.5 hours. Then, the reaction was maintained at 55°C for another half hour. Acetone was evaporated at atmospheric pressure. Water (50ml) was added. The resulting product solution was neutralized to a pH of around 6 using 32% industrial hydrochloric acid at 30°C. Then, the solution was filtered, washed with warm water (10 ml) at 40°C, filtered under reduced pressure to remove water, and dried at 70°C to obtain theobromine in 84.3% yield.

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Abstract

The invention provides a new method for preparing a theobromine by a 3-methyl xanthine disodium salt methylation with more production value. The theobromine is prepared by using acetone as a solvent to react with a dimethyl sulfate under the existence of a sodium carbonate and then acidified. The invention uses the acetone as the solvent and decreases the hydrolysis loss of the dimethyl sulfate; the sodium carbonate provides an alkaline condition for the methylation reaction and the Ph value is intermediate. The dimethyl sulfate is dropped to carry out the methylation reaction with the advantages of good selectivity and a yield higher than other methylation technique by more than 10 percent. The acetone is recycled and reused, the reaction is relatively complete and has little caffeine by-product, and the acquired analysis content of theobromine crude product HPLC is larger than 90 percent. The invention is extremely applicable to industrial production.The invention relates to a refining method of santheose, which is characterized in that dissolves liquid alkali into crude santheose solution, decolourizes, fitlers, and adds reduction agent into filter liquor, acidifies at 60-80 DEG C until pH=5-6, filters and dries to obtain santheose final product. The inventive method has refining yield of 90%, standard product color, high product quality, low cost and industrialization suitability.

Description

technical field [0001] The invention relates to the field of synthetic chemistry, in particular to a new method for preparing and refining theobromine. Background technique [0002] Theobromine, also known as 3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione, is represented by the following structural formula: [0003] [0004] Theobromine is the main alkaloid in cocoa beans, which contain 1.5-3% of theobromine, so it can be found in chocolate. The base is also found in kola nuts and tea. Theobromine belongs to the class of xanthines, which also includes caffeine and theophylline. Although the compound's name is "theobromine," it does not contain bromine because the name is actually derived from Theobroma, the genus name of the cocoa tree. [0005] Theobromine is a compound with the molecular formula C 7 h 8 N 4 o 2 of crystals. It is slightly soluble in water (0.5g / l), partially soluble in boiling water (1g / 150ml), almost insoluble in ether and chloroform. However, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/04
CPCC07D473/10
Inventor 李兴泰舒瑞友丰宇胜杨爱荣赵丽尼森·比尔曼
Owner PERRIGO TRADING (SHANGHAI) CO LTD
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