Bicarbonate Ion → Teaalcohol

HRID 1199252Notes

Reaction equation

HRID 1199252 reaction equation
OO.[CH3:3][C:4]1[CH2:10][C:8](=[O:9])[CH2:7][C:6]([CH3:12])([CH3:11])[CH:5]=1.C(O)=[O:14].OO.C(=O)([O-])[O-].C(=O)(O)[O-].C(=O)(O)[O-].[Na+]>C(O)=O>[CH3:3][C:4]1[CH:5]([OH:14])[C:6]([CH3:12])([CH3:11])[CH2:7][C:8](=[O:9])[CH:10]=1

Participants

8

Reactant 6

HCID 769Bicarbonate IonHCID 784Hydrogen PeroxideHCID 10108Beta-Isophorone2×HCID 19660Carbonate IonHCID 516892Sodium BicarbonateHCID 86612481HCID 86612481, compound

Product 1

HCID 566734Teaalcohol

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The process of the present invention is relatively simple technically. Inexpensive commercial chemicals are used as reagents. For example, formic acid and 30% hydrogen peroxide solution are placed in a stirred apparatus in a molar ratio of from about 1:1 to about 5:1 in a temperature range between 0° C. and 100° C., and about 0.5 to 2.5 moles, preferably 1 mole of beta-isophorone is added slowly. The formic acid/hydrogen peroxide mixture may also be added to the beta-isophorone. Gentle cooling may be used to remove the heat of reaction, depending on the selected temperature conditions and batch size. After completing the reaction and allowing the reaction to stand, the batch, which has become homogeneous, is neutralized with a suitable base, such as for example an alkali or alkaline earth metal hydroxide, oxide, carbonate or bicarbonate. A preferred base is sodium bicarbonate. The upper phase that forms is separated, dried, and distilled under vacuum. After the separation of back-isomerized alpha-isophorone, 4-hydroxyisophorone is obtained as a distillate. The alpha-isophorone distilled off in the forerun can be recycled to the process after reisomerization according to DE-OS 37 35 211.

Workup

  1. additionis added slowly
  2. customto remove the
  3. temperatureheat of reaction
  4. customthe reaction
  5. customthe reaction
  6. customThe upper phase that forms is separated
  7. customdried
  8. distillationdistilled under vacuum
  9. customAfter the separation of back-isomerized alpha-isophorone

Sources & evidence

ORD record
ord-bba81c915fc34a2b87309839015bbff8
Source dataset
uspto-grants-1990_02
Patent number
US04898984

Reaction notes

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