2-METHYL-ACRYLIC ACID BIPHENYL-4-YL ESTER synthesis
- Product Name:2-METHYL-ACRYLIC ACID BIPHENYL-4-YL ESTER
- CAS Number:46904-74-9
- Molecular formula:C16H14O2
- Molecular Weight:238.28
Yield:46904-74-9 100%
Reaction Conditions:
with dmap;2,6-di-tert-butyl-4-methyl-phenol in toluene at 80; for 40 h;
Steps:
5
Example 5 (Compound C-9)[0058] The starting material 4-methacyloxybiphenyl was prepared by charging a 250 rnL, 1-neck flask with 34.04 g (0.2 mole) 4-phenylphenol, 30.3 g (0.21 mole) methacrylic anhydride, 100 mL toluene, 0.2 g DMAP, and 0.025 g BHT. This mixture was stirred at 80° C for 40 hours. The solution was then passed over 20 g of silica gel and the solvent was removed to yield 47.8 g (100 % of theory) of a white solid that had a melting point of 111 - 112.6° C. The FTIR spectrum of this compound showed all of the phenolic -OH had disappeared. It also revealed prominent absorptions at 1731, 1637, 1484, 1320, 1207, 1127, 761, and 696 wave numbers.[0059] A 125 mL single-neck flask was charged with 23.83 g (0.100 mole) of the above compound, 13.7 g (0.120 mole) allylglycidyl ether, 0.2 g DMAP, 0.07 g BHT, and 130 mL toluene. This mixture was stirred at 100° C for 46 hours. The mix was originally two phases, but became a hazy single phase within the first hour of mixing at temperature. The solution was cooled and then passed over 30 g of silica gel. The solvent was removed to yield 26.1 g (74.0% of theory) of a clear, red, fairly mobile liquid. An FTIR revealed prominent absorptions at 1719, 1637, 1609, 1519, 1485, 1291, 1249, 1154, 1108, 1045, 937, 832, 762, and 696 wave numbers. A DSC was run on this compound in the presence of 2% dicumyl peroxide (10° C per minute ramp, air purge). A cure was observed to occur at 155.6° C with an onset temperature of 141.0° C. The cure energy was 150.8 J/g. A TGA was run on the monomer with and without 2% added dicumyl peroxide (10° C per minute ramp, air purge). The weight loss at 300° C was 16.9% in the presence of the catalyst and 31.3% without it.
References:
WO2008/77140,2008,A2 Location in patent:Page/Page column 27
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