Preparation of riboflavin 5'-phosphate (FMN) and its sodium salt in a lactone
AssigneeBASF SE
InventorsJohannes Grimmer, Hans Kiefer
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Abstract
An improved process for preparing riboflavin 5'-phosphate (FMN) or its monosodium salt by reacting riboflavin with excess phosphorus oxychloride in a solvent, hydrolyzing of the resulting reaction mixture and, if desired, partially neutralizing with aqueous sodium hydroxide solution, comprises reacting the riboflavin with from 1.2 to 3 moles of phosphorus oxychloride per mole of riboflavin in a suitable lactone, especially .gamma.-butyrolactone, as solvent. The process is particularly advantageous when the reaction mixture is hydrolyzed at from 80.degree. to 90.degree. C. continuously or batchwise.
Claims8
A process for preparing riboflavin 5'-phosphate or its monosodium salt by reacting riboflavin with excess phosphorus oxychloride in a solvent, hydrolyzing the resulting reaction mixture by treatment with water and, for preparing the monosodium salt, partially neutralizing with aqueous sodium hydroxide solution, which comprises reacting the riboflavin with 1.2 to 3 moles of phosphorus oxychloride per mole of riboflavin in a suitable lactone selected from the group consisting of .gamma.-butyrolactone, .gamma.-decalactone, and .gamma.-valerolactone.
A process for preparing pure riboflavin 5'-phosphate or its monosodium salt, which comprises
- A:
- reacting riboflavin with 1.2 to 3 moles of phosphorus oxychloride per mole of riboflavin in .gamma.-butyrolactone at from 20.degree. to 50.degree. C.,
- B:
- treating the resulting reaction mixture which contains the novel cyclic riboflavin 4',5'-phosphochloridate of the formula III ##STR3## with about 30 to 50 moles of water per mole of phosphochloridate at 70.degree. to 90.degree. C.
- C:
- maintaining the reaction mixture at 80.degree. to 95.degree. C, for 1 to 15 minutes,
- D:
- then adding 65 to 100 moles of water per mole of riboflavin to the reaction mixture and isolating the riboflavin 5'-phosphate which has crystallized out or, for preparing the monosodium salt,
- E:
- adjusting the reaction mixture obtained from D to a pH of 5.5 to 6 at from 20.degree. to 40.degree. C. with aqueous NaOH, and isolating the monosodium salt of riboflavin 5'-phosphate which has crystallized out.
Dependencies are inferred from the claim text.