Oxalic Acid → 4-Ethynylphenol
Reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)=[CH2:2].C(C1C=CC(O)=CC=1)C.C1(O)C=CC=CC=1.C1C(O)=CC=C(C)C=1.C(O)(=O)C(O)=O>O>[CH:2]#[C:1][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 180 °C
Procedure
409.8 g of a mixture consisting of 21.4% of p-vinylphenol, 59.8% of p-ethylphenol, 1.5% of phenol, 7.7% of p-cresol and 9.6% of water was introduced, over 30 minutes, into a rotary evaporator heated at 180° C. under a vacuum of 6 mmHg, and vacuum flash distillation was conducted. 364.2 g of a distillate was obtained and its composition was 21.3% of p-vinylphenol, 61.6% of p-ethylphenol, 1.5% of phenol, 7.8% of p-cresol and 7.8% of water. 132.4 g of this p-vinylphenol fraction was mixed, without being dehydrated, with 0.12 ml of a 0.5 M aqueous oxalic acid solution. The -resulting mixture was polymerized at 45° C. for 6 hours. The reaction mixture was treated in the same manner as in Example 1 to obtain 26.2 of a poly(p-vinylphenol). The polymer had a Mw of 10,470, Mn of 7,180, a light transmittance at 248 nm, of 70.5% and glass transition temperature of 173° C.
Workup
- additionwas introduced, over 30 minutes, into a rotary evaporator
- custom364.2 g of a distillate was obtained
- customThe -resulting mixture was polymerized at 45° C. for 6 hours
- additionThe reaction mixture was treated in the same manner as in Example 1
Sources & evidence
- ORD record
- ord-a450cbadf5be416a83a4cceda65e125d
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06258901B1
Reaction notes
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