Name | Stearolic acid |
Synonyms | STEAROLIC ACID Stearolic acid 9-stearolic acid 9-octadecynoic acid OCTADEC-9-YNOIC ACID 9-hydroxy-3-methyl-1H-benzo[g]quinoline-2,5,10-trione |
CAS | 506-24-1 |
EINECS | 208-030-8 |
Molecular Formula | C18H32O2 |
Molar Mass | 280.45 |
Density | 0.9365 (rough estimate) |
Melting Point | 46-47°C |
Boling Point | 189-190°C 2mm |
Flash Point | 189-190°C/2mm |
Water Solubility | Insoluble in water. |
pKa | 4.77±0.10(Predicted) |
Storage Condition | -20°C |
Refractive Index | 1.4283 (estimate) |
MDL | MFCD00014386 |
Physical and Chemical Properties | NIST Chemical Information 9-Octadecynoic acid(506-24-1) |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
BRN | 1786634 |
add 100g(0.35mol) of oleic acid (2) and 400mL of anhydrous ether to a reaction bottle equipped with a stirrer, thermometer and dropping funnel, cool to 0 ℃, add 53g(0.33mol) of bromine dropwise until the color of bromine does not fade, and add a few drops of oleic acid to fade the hydrochloric acid of bromine. Keep the internal temperature at 0~5 ℃ for standby. A reaction bottle equipped with a stirrer and a dropping funnel is used for ice-acetone cooling, 1900mL of liquid ammonia and 1.6g of anhydrous ferric chloride are added, stirred vigorously for 5-10min, 3g of metal sodium is added, and 43g(1.87mol) of metal sodium is added in batches when hydrogen is no longer released. After adding, stir and slowly add the above bromide solution dropwise. After adding, continue to stir for 6 hours. Then add 60g of solid sodium chloride to volatilize the ammonia. Add 1000mL of water, heat to 60~70 ℃ under nitrogen protection, and slowly add 50mL of concentrated hydrochloric acid to acidify. The water layer is separated, and the organic layer is washed four times with hot water at 60 ℃. Ice bath cooling, suction filtration, vacuum drying, crude products. Dissolve the crude product in 500mL of petroleum ether and filter. Concentrate to 300mL, cool to 0~5 ℃, filter by suction, and wash with a small amount of cold petroleum ether. Part of the product can be obtained by concentrating the mother liquor. The product obtained twice was recrystallized with 300mL petroleum ether and dried in vacuum to obtain 51.5-61.5g of stearic acid (1) with a yield of 51%-61%.