Sebacic Acid → HCID 2858575, compound

HRID 917809Notes

Reaction equation

HRID 917809 reaction equation
[C:1]([OH:14])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].[CH2:15](O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C(C)=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:1]1(=[O:14])[O:13][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:12][C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 5192Sebacic Acid2×HCID 6101p-Toluenesulfonic acidHCID 7237O-XyleneHCID 123741,6-Hexanediol

Product 1

HCID 2858575HCID 2858575, compound

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

Crystalline poly (hexamethylene sebacate) was prepared using a kettle equipped with a stirrer, nitrogen gas inlet tube, thermometer and condenser by reacting sebacic acid with 1,6hexamethylene glycol in the presence of a p-toluenesulfonic acid catalyst as follows: sebacic acid and hexamethylene glycol were added to the reaction kettle in a respective 1.0 to 1.1 molar ratio along with 0.5 wt % p-toluenesulfonic acid. The 10 mole % excess of glycol was used to ensure the predominant presence of hydroxyl end groups in the reaction product. The mixture was heated to 165°C while stirring. At 165°C, an amount of xylene was added to assist refluxing and this temperature was maintained until water evolution ceased (4 hrs.). Afterwards, the condensers were removed and the excess glycol and catalyst were removed by sparging with nitrogen for 0.5 hours at 165°C. On cooling to room temperature, the poly (hexamethylene sebacate) crystallized into an off-white solid. Next, the poly (HMS) from above was purified by precipitation from a benzene solution into methanol using techniques well known in the art. The precipitated poly (HMS) was collected by filtration and dried in vacuo. Analytical data on this purified material indicate an acid number of 1.06, an hydroxyl number of 34.4, an Mn of 3165 g/mole, an MWD (Mw /Mn) of 1.41 by GPC in chloroform, a glass transition temperature of about -62°C and a crystalline melting point of about 65°C.

Workup

  1. customequipped with a stirrer, nitrogen gas inlet tube
  2. customthermometer and condenser by reacting
  3. temperatureto assist refluxing
  4. custom(4 hrs.)
  5. customAfterwards, the condensers were removed
  6. customthe excess glycol and catalyst were removed
  7. customby sparging with nitrogen for 0.5 hours at 165°C
  8. temperatureOn cooling to room temperature
  9. customthe poly (hexamethylene sebacate) crystallized into an off-white solid
  10. customNext, the poly (HMS) from above was purified by precipitation from a benzene solution into methanol using techniques
  11. customThe precipitated poly (HMS)
  12. filtrationwas collected by filtration
  13. customdried in vacuo

Sources & evidence

ORD record
ord-dc2b185bac274c958790bfe1951d421f
Source dataset
uspto-grants-1976_07
Patent number
US03967962

Reaction notes

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