Ethylene carbonate → HCID 14950291, compound
Reaction equation
[CH2:1]([NH2:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:8]1(=[O:13])[O:12][CH2:11][CH2:10][O:9]1>>[CH2:1]([NH:7][C:8](=[O:13])[O:9][CH2:10][CH2:11][OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
Conditions
- Temperature
- 70 °C
Procedure
N-hexylamine (8.8 g, 100 mmole) and ethylene carbonate (10.12 g, 100 mmole) was mixed into a solution, and the solution is then further heated to 70° C. After reacting for 5 hours, the product was purified by vacuum distillation (128-130° C./0.05 mmHg) to form 2-hydroxyethyl N-hexyl-carbamate (compound I), 15.1 g (yield: 80%), which is an achromatic oily liquid. 2-hydroxyethyl N-hexyl-carbamate (compound I, 4.73 g, 25 mmole), benzaldehyde dimethylacetal (3.79 g, 25 mmole), and a catalyst of p-toulenesulfonic acid (0.05g) are mixed. Thus, the mixed solution was gradually heated to 160° C. and then reacted for 2 hours. Methanol formed in the period is then removed. Thereafter, the mixed solution was processed by vacuum distillation (0.01 mmHg) and heated to 200° C. A thermally decomposable polymer (A) (poly(N,O)acetal, PA) 5.5 g (yield: 65%) was obtained after 2 hours, which is a highly viscous oily constituent with orange-red color. Referring to the reaction formula below, the synthesis procedure of the thermally decomposable polymer (A) is shown below:
Workup
- distillationthe product was purified by vacuum distillation (128-130° C./0.05 mmHg)
Sources & evidence
- ORD record
- ord-dd81705283544d1d8e35e4839144655a
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07806974B2
Reaction notes
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