Synthetic method for aliphatic alpha-calcium picrolonate

A synthetic method and technology of calcium ketoacids, which are applied in the field of synthesis of aliphatic α-ketoacid calcium, and can solve problems such as unsynthesized aliphatic α-ketoacids

Inactive Publication Date: 2009-08-26
NANJING CHEM REAGENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1, the synthesis of calcium α-ketoisocaproate

[0061] (1) Synthesis of isobutylene hydantoin intermediate

[0062] Take 10g hydantoin (0.1mol) and 8g sodium bicarbonate (0.08mol) into a three-necked flask, add water to mix and stir, raise the temperature to 70-80°C, add 9.3g (0.13mol) of isobutyraldehyde, reflux for 8 hours, and cool After reaching room temperature, 50% sulfuric acid was added to adjust the pH value, a large amount of solid precipitated, filtered and washed with water, and the dried white solid isobutylidene hydantoin was 12.4g, the yield was 81%, and the melting point was 120-122°C. Elemental analysis is qualified.

[0063] (2) Synthesis of calcium α-ketoisocaproate

[0064] Put 15.4 g (0.1 mol) of isobutylene hydantoin and 100 ml of 20% sodium hydroxide solution in a three-necked flask, stir and reflux for 2 hours, adjust the pH value with 50% sulfuric acid, evaporate the water to dryness under reduced pressure, and add methanol Extract...

Embodiment 2

[0065] Embodiment 2, the synthesis of α-ketoisovalerate calcium

[0066] (1) Synthesis of isopropylidene hydantoin intermediate

[0067] Add 10g (0.1mol) of hydantoin, add 12ml of water, stir and heat to 60°C, add 7.54g (0.13mol) of acetone, add 4.8g (0.08mol) of ethanolamine dropwise in 30 minutes, and stir and react at 70°C for 6 hours after dropping, the reaction is completed After cooling, the pH was adjusted to 4 with concentrated HCl to precipitate a solid, which was filtered, washed and dried with 10 ml of water to obtain 13.3 g, with a yield of 95%. The melting point is 279°C, and the elemental analysis is qualified.

[0068] (2) Synthesis of α-ketoisovalerate calcium

[0069] Take 14 g (0.1 mol) of mesitylidene hydantoin intermediate and 100 g of 20% (mass ratio) NaOH solution, heat and reflux at 110 degrees Celsius for 2 hours, cool after the reaction and adjust the pH to 5 with concentrated HCl, cool and filter to remove the solid, and the filtrate Concentrate to...

Embodiment 3

[0070] Embodiment 3, the synthesis of α-keto-β-methylvalerate calcium

[0071] (1) Synthesis of isobutyl hydantoin intermediate

[0072] Add 10g (0.1mol) of hydantoin, add 12ml of water, stir and heat to 60°C, add 9.37g (0.13mol) of butanone, dropwise add 4.8g (0.08mol) of ethanolamine, and stir and react at 80°C for 4 hours. Concentrated HCl was adjusted to PH=4, and a solid precipitated out, which was filtered, washed with distilled water and dried to obtain 9.4 g with a yield of 61%, and the elemental analysis was qualified.

[0073] (2) Synthesis of α-keto-β-methylpentanoic acid calcium salt

[0074] Take 15.4g (0.1mol) of the intermediate and 100g of 20% (mass ratio) NaOH solution, heat to reflux for 2 hours, 110 degrees Celsius, adjust the pH to 5 with concentrated HCl after the reaction, cool and filter to remove the solid, and concentrate the filtrate to dryness under reduced pressure , add 150ml of anhydrous methanol and heat to reflux for 1 hour, filter while it is...

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Abstract

A synthetic method for aliphatic alpha-calcium picrolonate comprises the following steps: 1. adding carbonyl group reactant in glycolylurea in the presence of catalytic accessory and water and heating, wherein the mol ration of the glycolylurea and the carbonyl group reactant is 1:1.2-1.4; the carbonyl group reactant is aldehyde compound or ketone compound; when aldehyde compound is adopted the catalytic accessory is potassium bicarbonate, and when ketone compound is adopted the catalytic accessory is ethanolamine; 2. cooling to the room temperature, regulating the pH valve to 7 and separating out the intermediate product; 3. filtering and washing the intermediate product; 4. stirring and refluxing the intermediate product and sodium hydroxide solution, wherein the mol ratio of the intermediate product and sodium hydroxide is 1:3-5; 5. regulating the pH value to 4-5, antiregulating the pH value to 7 with the sodium hydroxide solution, and evaporating to remove the moisture; 6. adding absolute methyl alcohol to extract for several times and filtering; 7. distilling to remove the methyl alcohol; and 8. adding de-ionized water and aqueous calcium chloride solution of equivalent amount and separating out alpha-calcium picrolonate. As massive subsidiary products are removed in the method, the calcium content in the prepared product can achieve the standard.

Description

technical field [0001] The invention relates to a chemical synthesis method, in particular to a synthesis method of aliphatic alpha-ketoacid calcium. Background technique [0002] α-keto acids are a class of bifunctional compounds, and their general structural formula is as follows: [0003] RCOCOOH [0004] Wherein, the R group is an aromatic hydrocarbon group, which is an aromatic α-keto acid; [0005] or the R group is an alkane group, which is an aliphatic α-keto acid; [0006] α-ketoacids are important intermediates produced in the metabolism of amino acids, proteins and other compounds in vivo, and play a very important role in the life activity system. Recently, α-ketoacids are widely used in food industry, daily chemical industry It is widely used in industries such as medicine and medicine. In the adjuvant treatment of patients with hepatic and renal failure, α-keto acid salt can be used as an additive of low-nitrogen and high-protein food to replace the corresp...

Claims

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Application Information

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IPC IPC(8): C07C59/185C07C51/41
Inventor 邹建忠丁春玉张征林王浩
Owner NANJING CHEM REAGENT
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