New polymers derived from renewably resourced lysinol
a technology of lysinol and polymer, which is applied in the field salt compositions of lysinol and dicarboxylic acids, and lysinol derived polymers, can solve the problems of increasing the cost of obtaining, placing a high burden on petroleum feedstock, and non-renewable resources
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example 1
Preparation of Lysinol from Lysine Hydrogenation
[0123]The examples below illustrate the preparation of lysinol from the hydrogenation of lysine in the presence of a catalyst, hydrogen, and aqueous acid.
example 1.1
Preparation of Lysinol (Lysinol-1.1) by Lysine Hydrogenation Using Phosphoric Acid
[0124]A high pressure reactor was charged with 3.03 g lysine (20.7 mmol), 0.255 g (0.13 mmol Ru) Ru / C catalyst, and 17 mL of 2.53 M H3PO4 (43.0 mmol). After purging with hydrogen the reactor was brought to 6.9 MPa initial pressure at 120° C. and gas uptake was monitored. The vessel was repressurized to 6.9 MPa after 5.5 h and 20.5 h. Gas uptake ceased after ca. 24 h. After cooling and venting the reactor, a sample taken from the reactor showed complete lysine conversion by liquid chromatography. The slurry from the reactor was filtered and washed with water. NaOH (5.2 g, 130 mmol) dissolved in a minimal amount of water was added to the filtrate to get a solution with pH >12. Water was then removed from the solution on a rotary evaporator to provide a mixture of lysinol and sodium phosphate. This colorless residue was extracted with ethanol to separate the ethanol-soluble lysinol from the salt. The etha...
example 1.2
Preparation of Lysinol (Lysinol-1.2) by Lysine Hydrogenation Using Sulfuric Acid
[0125]A 1 gallon plastic jug, cooled with a wet ice / acetone bath was charged with (S)-lysine (97%, 420.0 g, 2.79 mol) and 2.2 L of deionized water. Concentrated sulfuric acid (160 mL, 2.94 mol) was slowly added to the chilled slurry of (S)-lysine and water with stirring, maintaining the temperature below 30° C. The mixture was stirred until all of the lysine had dissolved and the temperature had returned to 20-25° C. The solution along with catalyst, 100.0 g of 5% ruthenium on carbon were then transferred to a one gallon autoclave reactor. The reactor was then pressurized with hydrogen to 6.9 MPa and heated to 120° C. Hydrogen was added as needed to the reactor to maintain 6.9 MPa pressure until the hydrogen uptake was ceased. After 22.5 hours, the reactor was cooled to room temperature and depressurized. LC analysis showed quantitative conversion of lysine. The catalyst was removed by filtration, washed...
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