Methyl Ethyl Ketone → Adipic Acid

HRID 1825027Notes

Reaction equation

HRID 1825027 reaction equation
C[C@H]1C[O:29][C@@:5]2([O:9][C@H:8]3C[C@H]4[C@@H]5CC=C6C[C@@H](O)CC[C@]6(C)[C@H]5CC[C@]4(C)[C@H]3[C@@H]2C)[CH2:4][CH2:3]1.[O:31]=[C:32]=NC1CC(C)(C)CC(C)(CN=C=O)C1.C[C:48](=[O:51])[CH2:49][CH3:50]>>[C:5]([OH:29])(=[O:9])[CH2:4][CH2:3][CH2:50][CH2:49][C:48]([OH:51])=[O:31].[OH:51][CH2:48][C:49]([CH3:32])([CH2:8][OH:9])[CH3:50]

Participants

5

Reactant 3

HCID 6569Methyl Ethyl Ketone2×HCID 99474DiosgeninHCID 169132Isophorone diisocyanate

Product 2

HCID 196Adipic AcidHCID 31344Neopentyl glycol

Procedure

A 4-neck flask was fitted with a variable speed stirrer, thermocouples in combination with a controller, a condenser, a nitrogen in- and outlet, an addition funnel, and a heating mantle. In the flask were placed 77.03 g isophorone diisocyanate and 70 g dry 2-butanone. A mixture of 36.8 g Tegomer D3403 (available from Tego Chemie Service), 80.22 g dry 2-butanone, 23.82 g of Rucoflex S-107-210 (a polyesterdiol resulting from the reaction of adipic acid and neopentyl glycol, available from Ruco Polymers), 59.9 g of acetal-functional intermediate E, described above, 0.22 g tin(II)octanoate, and 21.14 g of acetal functional intermediate D, described above, was added during 1 hour. The mixture was further heated to 85° C. and kept at this temperature for 19 hours. After this time, the isocyanate content of the mixture was below 0.1%. The mixture was cooled to 45° C. and transferred to a 2 I round-bottom flask with baffles and the above-mentioned equipment. The stirring speed was set to 350 RPM and 435 g water were added at a rate of 2.7 ml/min. When the addition of water was complete, the emulsion was transferred to a 2 I flask fifted with the above-mentioned equipment and a distillation head. The temperature was maintained at 45° C. A vacuum pump was connected to the flask and the pressure was gradually lowered until substantially all 2-butanone was distilled off.

Workup

  1. customA 4-neck flask was fitted with a variable speed stirrer
  2. additionA mixture of 36.8 g Tegomer

Sources & evidence

ORD record
ord-ba50c6bb46974584bf807627e055ef02
Source dataset
uspto-grants-2006_05
Patent number
US07045579B2

Reaction notes

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