p-Toluenesulfonic acid monohydrate → Chdmdve

HRID 2273369Notes

Reaction equation

HRID 2273369 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:13]([O:15][CH2:16][C:17]1([CH2:23][O:24][CH:25]=[CH2:26])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[CH2:14].C(Cl)(Cl)Cl>>[CH:25]([O:24][CH2:23][C:17]1([CH2:16][O:15][CH:13]=[CH2:14])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[CH2:26]

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 131733385HCID 131733385, compound

Product 1

HCID 21867826ChdmdveYield 261.5%

Procedure

PLA Based Polyacetal Containing Diamino Ester/Caprolactone Adduct Polyacetal(PLA/CHDM/CHDMDVE/phenylalanine ester-caprolactone adduct) was produced using the following procedure: Poly-I-lactic acid diol (4 g, Mn=5200/Mw=10800) and diphenylalanine ester/caprolactone (3.0 g) adducts were placed into a 125 ml glass vial. p-Toluene sulfonic acid monohydrate(16 mg) was added to the vial and the contents dried in a vacuum oven (100 C/4 hr). The vial was then stoppered (silicon stopper/aluminium crimp lid) and 30 ml of anhydrous chloroform was added. This was stirred using a magnetic stirrer at room temperature. The PLA diol was polymerised with (cis/trans) cyclohexane dimethanol divinyl ether (CHDMDVE). A CHDMDVE/anhydrous chloroform solution (2 g/10 ml) was prepared and added in small aliquots. The resulting solution was noted to become cloudy. The solution was then filtered, via a syringe fitted with a 0.45 um nylon filter, into a separated sealed Wheaton vial (125 ml) containing CHDM (1.0 g), magnetic stirrer and p-TSA (10 mg). This formed a clear straw yellow solution. 9 ml of a CHDMDVE/chloroform solution (1.23 g/10 ml chloroform) was added over a 2 hr period. The resulting viscous solution was purified by passing the solution through an Al2O3/glasswool column, precipitating into methanol and dried to remove residual solvent. The polymer structure was confirmed using FTIR and NMR. Polymer rods (approx. 6.0 mm diameter) were produced by packing a PTFE block, containing a 6.2 mm hole, with polymer. The resulting mould was heated at 180 for 10 mins until the polymer had become molten. The molten polymer was then compressed and cooled to form a soft rod which crystallised on cooling.

Workup

  1. customwas produced
  2. customdried in a vacuum oven (100 C/4 hr)
  3. additionwas added
  4. customat room temperature
  5. additionadded in small aliquots
  6. filtrationThe solution was then filtered, via a syringe
  7. customfitted with a 0.45 um nylon
  8. filtrationfilter, into a separated
  9. customsealed Wheaton vial (125 ml)
  10. additioncontaining CHDM (1.0 g), magnetic stirrer and p-TSA (10 mg)
  11. customThis formed a clear straw yellow solution
  12. customThe resulting viscous solution was purified
  13. customprecipitating into methanol
  14. customdried
  15. customto remove residual solvent
  16. customPolymer rods (approx. 6.0 mm diameter) were produced
  17. additioncontaining a 6.2 mm hole
  18. temperatureThe resulting mould was heated at 180 for 10 mins until the polymer
  19. temperaturecooled
  20. customto form a soft rod which
  21. customcrystallised
  22. temperatureon cooling

Sources & evidence

ORD record
ord-66fcc1329fdc4690833fc53c270b4b1c
Source dataset
uspto-grants-2015_09
Patent number
US09120919B2

Reaction notes

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