Methanol → HCID 18616065, compound

HRID 1414157Notes

Reaction equation

HRID 1414157 reaction equation
[C:1]([O:13]C)(=[O:12])[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][CH:3]=1.CO.[C:17]([O-:26])(=[O:25])[CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O-:24])=[O:23]>C(O)CO>[C:1]([O-:13])(=[O:12])[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O-:8])=[O:7])=[CH:4][CH:3]=1.[C:17]([O-:26])(=[O:25])[CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 8441Dimethyl terephthalateHCID 200164Adipate(2-)

Product 1

HCID 18616065HCID 18616065, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent2×

Procedure

In a stainless steel distilling pot having a drain valve in the bottom is placed 11 lbs. (5.0 kilograms) of dimethyl terephthalate, 7 lbs. 6 oz. (3.35 kilograms) of ethylene glycol and 120 milliliters glycol solution of 2.45 grams Mn(C2H3O2)2 . 4H2O and 1.69 grams of Sb2O3. The mixture is heated to 240°C. over a 3 hour period during which time 1,650 grams of methyl alcohol and 750 grams of ethylene glycol are removed sequentially. The resulting monomer is drained to a stainless steel autoclave fitted with stirrer, charging port, vacuum distillation system, and extrusion valve. To the autoclave is added 285 grams of a glycol solution of di(2-hydroxyethyl) adipate (equal to 163.6 grams of adipic acid), 24 milliliters of an ethylene glycol solution of phosphoric acid containing 1.79 grams of phosphoric acid (as 100% H3PO4), and 27 milliliters of 20% TiO2 in ethylene glycol. The pressure is reduced slowly over a period of about 2.5 hours to about 5 torr, then the autoclave is pressurized with inert gas (Kemp gas) and 317 grams of PHP-20EO diluted with 200 milliliters of ethylene glycol is added. The pressure is gradually reduced over a period of 0.5-hour and polymerization is then continued for about 2 hours at 225°C. at 1.3 torr. The melt is extruded, cooled, and cut to 0.25-inch (0.64-centimeter) flake. The flake has a relative viscosity of 11.1 and contains 0.077% nitrogen and 4.5 mole % adipate units.

Workup

  1. customare removed sequentially
  2. customfitted with stirrer
  3. distillationport, vacuum distillation system, and extrusion valve
  4. additionTo the autoclave is added 285 grams of a glycol solution of di(2-hydroxyethyl) adipate (equal to 163.6 grams of adipic acid), 24 milliliters of an ethylene glycol solution of phosphoric acid containing 1.79 grams of phosphoric acid (as 100% H3PO4), and 27 milliliters of 20% TiO2 in ethylene glycol
  5. waitThe pressure is reduced slowly over a period of about 2.5 hours to about 5 torr
  6. additiondiluted with 200 milliliters of ethylene glycol
  7. additionis added
  8. waitThe pressure is gradually reduced over a period of 0.5-hour
  9. custompolymerization
  10. temperaturecooled

Sources & evidence

ORD record
ord-1645983211504127953536067f8b1bd1
Source dataset
uspto-grants-1977_01
Patent number
US04001189

Reaction notes

Loading…