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Theobromine production process

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

Inactive Publication Date: 2013-06-12
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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Effect test

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

A process for preparing theobromine by methylating 3-methyl xanthine disodium salt comprises reacting 3-methyl xanthine disodium salt with dimethyl sulfate by using acetone as solvent in the presence of sodium carbonate and acidifying. The present application also provides a process for refining theobromine which comprises dissolving coarse theobromine in liquid alkaline solution, decolorizing, filtering, adding reducing agent in filtrate, and acidifying at 60-80 °C until pH is 5-6, filtering, and drying to obtain theobromine.

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 Patents(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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