Adipic Acid → L-Ascorbic Acid

HRID 839778Notes

Reaction equation

HRID 839778 reaction equation
[CH2:1]([OH:5])[CH:2]([OH:4])[CH3:3].C([C:8]([CH2:13][OH:14])([CH2:11][OH:12])CC)O.C(O)(=O)CCCCC(O)=[O:21].C1(=O)OC(=O)C2=CC=CC=C12.[OH-:36].[K+]>C(O)CO>[CH2:1]([OH:5])[C@H:2]([OH:4])[C@H:3]1[O:12][C:11](=[O:36])[C:8]([OH:21])=[C:13]1[OH:14]

Participants

7

Reactant 5

HCID 196Adipic AcidHCID 1030Propylene GlycolHCID 6510TrimethylolpropaneHCID 6811Phthalic AnhydrideHCID 14797Potassium Hydroxide

Product 1

HCID 54670067L-Ascorbic Acid

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

310.4 Parts of ethylene glycol, 380.5 parts of 1,2 -propanediol, 670 parts of 1,1,1-trimethylolpropane, 1023 parts of adipic acid and 444.3 parts of phthalic anhydride are condensed respectively for 2 hours at 140° C., 160° C., 180° C., and then at 200° C., until the acid number is smaller than 5 mg. KOH/g., thus separating 306 parts of water. After adding 1629 parts of phthalic anhydride, the reaction is continued at 150° C. until the acid number of the polyester is 150 mg. KOH/g. The OH-number is about 48 mg. KOH/g.

Workup

  1. customcondensed respectively for 2 hours at 140° C.
  2. custom160° C., 180° C.
  3. customat 200° C.
  4. custom, thus separating 306 parts of water
  5. additionAfter adding 1629 parts of phthalic anhydride
  6. customis continued at 150° C. until the acid number of the polyester

Sources & evidence

ORD record
ord-b880e8d12fd94f5c8a646f4929d1075a
Source dataset
uspto-grants-1978_06
Patent number
US04097466

Reaction notes

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