Hydrochloric Acid → 2-Methylidenebutanedioic acid--prop-2-enoic acid (1/1)

HRID 249224

Reaction equation

HRID 249224 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[C:6]([OH:14])(=[O:13])[C:7]([CH2:9][C:10]([OH:12])=[O:11])=[CH2:8].Cl>O>[CH2:3]=[CH:2][C:1]([OH:5])=[O:4].[CH2:8]=[C:7]([C:6]([OH:14])=[O:13])[CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811Itaconic acidHCID 6581Acrylic Acid

Product 1

HCID 1615092-Methylidenebutanedioic acid--prop-2-enoic acid (1/1)Yield 363.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Acrylic acid (25.000 g, 0.34693 mole), itaconic acid (5.0151 g, 0.038548 mole), Wako V-50 (0.1046 g, 0.3856 millimole), and 193 ml of water, which has been acidified to pH 2.0 with hydrochloric acid, are added to a 500 ml three-necked round-bottomed flask. The necks are fitted with a thermometer, a stopper, and a gas inlet/outlet adapter capable of bubbling gas through a liquid in the flask and venting it. The solution is deaerated by passage of nitrogen gas and is then placed under an atmosphere of argon. The solution is heated to 60° C. and is maintained at this temperature for 15 hours. The viscous solution of copolymer is cooled to ambient temperature and is dialzyed against distilled water overnight (Spectrapor 3 tubing with molecular weight cut-off at 3500) to remove any unreacted monomers. The dialyzed solution is freeze dried to give 28.31 g of poly(acrylic acid-itaconic acid) copolymer as a colorless solid. The mass average molecular weight, as determined by low angle laser light scattering in 0.2 Molar sodium chloride in water (refractive index=1.3344, dn /dc =0.1683), is 658,200.

Workup

  1. additionare added to a 500 ml three-necked round-bottomed flask
  2. customThe necks are fitted with a thermometer
  3. customa stopper, and a gas inlet/outlet adapter capable of bubbling gas through a liquid in the flask
  4. temperatureis maintained at this temperature for 15 hours
  5. temperatureThe viscous solution of copolymer is cooled to ambient temperature
  6. distillationagainst distilled water overnight (Spectrapor 3 tubing with molecular weight cut-off at 3500)
  7. customto remove any unreacted monomers
  8. customdried

Sources & evidence

ORD record
ord-1dc76a8f1fde4f24a9f131a2f8e3010c
Source dataset
uspto-grants-1993_05
Patent number
US05213789

Linked notes

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