DI-N-OCTADECYL PHOSPHATE synthesis
- Product Name:DI-N-OCTADECYL PHOSPHATE
- CAS Number:3037-89-6
- Molecular formula:C36H75O4P
- Molecular Weight:602.95
37032-33-0
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Yield:-
Reaction Conditions:
Stage #1: bis(hexadecyl) phosphonate;dioctadecyl hydrogen phosphonate;ethyl hexadecyl phosphite;ethyl octadecyl phosphite;hexadecyl octadecyl phosphitewith sodium hypochlorite;sodium hydroxide at 35 - 60; pH=9 - 11.5;
Stage #2: with sulfuric acid pH=2;
Steps:
23
EXAMPLE 2350 g of a 3:7 weight ratio of n-hexadecanol:n-octadecanol was premixed with 1.7 mL of a 2.2M Methanol solution of lithium methoxide. The mixture was rapidly added at room temperature to 26.4 g (0.19 mol) diethylphosphite. The resultant mixture was then distilled under vacuum of 1.00 mBar. At 23° C. ethanol was removed. At 43-48° C., unreacted diethylphosphite was distilled in greater than 99% purity, leaving behind 61.5 g of a mixture of ethylhexadecylphosphite, ethyloctadecylphosphite, dihexadecylphosphite, dioctadecylphosphite and hexadecyloctadecylphosphite as a white solid. The resulting phosphites were subsequently converted to the corresponding phosphates by reacting them with sodium hypochlorite. To accomplish this, 50 g of the above mixture was added to 104 g sodium hypochlorite solution (10-13% as active chlorine). The addition was performed in portions at temperatures between 35-40° C. while maintaining the pH between 9-11.5 with 25% NaOH. After all the phosphite was added the pH was raised to about 11-11.5 and the reaction mixture was stirred at 60° C. until the pH remained above 11. Afterwards the mixture was treated dropwise with 98% sulphuric acid until a pH of 2 was measured. The solid product was separated from the water phase by filtration. 51.3 g of a white solid was obtained consisting of ethylhexadecylphosphite, ethyloctadecylphosphate, dihexadecylphosphate, dioctadecylphosphate and hexadecyloctadecylphospate. The ratio between the asymmetric and symmetric phosphates was determined to be 1.9:1 as measured by 31P NMR.
References:
US2011/46408,2011,A1 Location in patent:Page/Page column 8
112-92-5
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