Methacrylic Acid → 6-Hydroxyhexyl Methacrylate (stabilized with MEHQ)

Temperature

90 °C

1,6-Hexanediol (1000.00 g, 8.46 mol, Sigma-Aldrich) was placed in a 1-liter 3-neck flask equipped with a mechanical stirrer and a narrow tube blowing dry air into the flask. The solid diol was heated to 90° C., at which temperature all the solid melted. With continuous stirring, p-toluenesulfonic acid crystals (18.95 g, 0.11 mol) followed by BHT (2.42 g, 0.011 mol) and methacrylic acid (728.49.02 g, 8.46 mol). Heating at 90° C. with stirring was continued for 5 hours during which time vacuum was applied using tap water aspirator for 5-10 minutes after each half-hour reaction time. The heat was turned off and the reaction mixture was cooled to room temperature. The viscous liquid obtained was washed with 10% aqueous sodium carbonate twice (2×240 ml), followed by washing with water (2×240 ml), and finally with 100 ml of saturated NaCl aqueous solution. The obtained oil was dried using anhydrous Na2SO4 then isolated by vacuum filtration to give 1067 g (67.70%) of 6-hydroxyhexyl methacrylate, a yellow oil. This desired product was formed along with 15-18% of 1,6-bis(methacryloyloxyhexane). Chemical characterization was by NMR analysis.

1. customequipped with a mechanical stirrer and a narrow tube
2. customblowing dry air into the flask
3. temperatureHeating at 90° C.
4. waitaspirator for 5-10 minutes after each half-hour
5. customreaction time
6. temperaturethe reaction mixture was cooled to room temperature
7. customThe viscous liquid obtained
8. washwas washed with 10% aqueous sodium carbonate twice (2×240 ml)
9. washby washing with water (2×240 ml)
10. customThe obtained oil was dried
11. customthen isolated by vacuum filtration

ORD record

ord-94a8d83118074af88426316a15adadf3

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09414995B2