Adipic Acid → HCID 4428274, compound

HRID 1591403Notes

Reaction equation

HRID 1591403 reaction equation
C(O)(=O)CCCCC(O)=O.[CH2:11]([NH2:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH2:21]([N:30](CCCCCCCCC)[C:31](=[O:39])[CH2:32][CH2:33][CH2:34][CH2:35][C:36](N)=[O:37])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[OH-].[Na+]>O>[CH2:11]([NH:20][C:36](=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32][C:31]([NH:30][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:39])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 196Adipic Acid3×HCID 14798Sodium HydroxideHCID 16215NonylamineHCID 54083699HCID 54083699, compound

Product 1

HCID 4428274HCID 4428274, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
160 °C

Procedure

Into a 1 L flask equipped as described as above in Example 1 were added 350.9 grams (2.4 moles) of adipic acid. This acid was heated to 160° C. with agitation until melted. After all of the adipic acid was melted, there were added 28.6 g (0.2 mole) of nonylamine over a period of about 15 minutes. The reaction mixture was held at 170° C. with agitation for an additional 3 hours under nitrogen. The reaction mixture was then gradually poured into 2 L of hot (70° C.) water, with agitation to dissolve the unreacted adipic acid. The mixture was filtered and the wetcake was washed with hot water to obtain a mixture of monoamido adipic acid and N,N1 -dinonyl adipamide. The wetcake was reslurried in a caustic solution (16 g of 50% sodium hydroxide and 200 g of water) whereby the acid dissolved leaving the insoluble N,N'-dinonyl adipamide as an insoluble which was removed by filtration. After drying overnight at 70° C., the amount of dinonyl amido adipamide was found to be 1.78 g (0.0045 mole). This amount of diamide represents a molar selectivity of 4.5% based upon the amine reactant. The alkaline solution was then acidified with an equivalent of sulfuric acid to precipitate the desired monoamido adipic acid which precipitated and was collected by filtration. After drying in an oven overnight at 70° C., the amount of monoamido adipic acid obtained was found to be 49 g (0.1808 mole) having a purity of 99.9% by HPLC. This amount of monoamido adipic acid represents a molar selectivity of 90% based upon the amine reactant. A sample of the acid was subjected to melting point determination which was found to be in the range of 108° C.-110° C. The filtrate containing dissolved adipic acid was cooled to room temperature, whereupon the adipic acid precipitated and was recovered by filtration. The solid collected from this filtration contained mostly adipic acid and a small amount of monoamido adipic acid. After removal of residual water, the adipic acid, containing small amounts of monoamido adipic acid, was ready to be used as starting material for further reaction with an amine. The filtrate obtained from the recovery of the adipic acid contained about 2% adipic acid and was used as the water source to dissolve further unreacted adipic acid from the next batch in the further production of monoamido adipic acid by the reaction of nonylamine with adipic acid.

Workup

  1. customInto a 1 L flask equipped
  2. filtrationThe mixture was filtered
  3. washthe wetcake was washed with hot water
  4. customto obtain
  5. dissolutiondissolved

Sources & evidence

ORD record
ord-56b76d757a72421f822849c5a07cca54
Source dataset
uspto-grants-1993_04
Patent number
US05206432

Reaction notes

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