Polyisobutenyl alcohol and fuel composition
A compound, aryl-based technology, applied in the field of substituted methylol polyisobutylene compounds, can solve problems such as expensive processing equipment
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Embodiment 1
[0108] Preparation of ω-Methylol Polyisobutene Using Dimethyl Aluminum Chloride
[0109]
[0110] Add 5 g of polyisobutylene (molecular weight 1,000, 80% methylvinylidene), 136.5 mg of paraformaldehyde, and 15 mL of anhydrous dichloromethane to a flask equipped with a magnetic stirrer and nitrogen inlet. Dimethylaluminum chloride (6.8 mL of a 1M solution in hexane) was added via syringe in one portion. The reaction solution was then stirred at room temperature for 16 hours. The reaction was cooled in an ice bath and 15 mL of 1% hydrochloric acid solution was added dropwise. The resulting biphasic solution was extracted with hexane (3 x 15 mL). The combined organic layers were dried over magnesium sulfate, filtered and the solvent was removed under vacuum to obtain the crude product. The crude reaction product was chromatographically purified on silica gel eluting with hexanes followed by 10% ethyl acetate in hexanes to afford 3.85 g of the desired product as a colorless ...
Embodiment 2
[0112] Preparation of ω-4-Nitrophenylhydroxymethyl Polyisobutene Using Dimethyl Aluminum Chloride
[0113]
[0114] To a flask equipped with a magnetic stirrer and nitrogen inlet, add 5.35 g of polyisobutene (molecular weight 1,000, 80% methylvinylidene), 0.74 g of 4-nitrobenzaldehyde, and 15 mL of anhydrous dichloromethane. Dimethylaluminum chloride (6.8 mL of a 1M solution in hexanes) was added via syringe in one portion. The reaction solution was then stirred at room temperature for 16 hours. The reaction was cooled in an ice bath and 15 mL of 1% hydrochloric acid solution was added dropwise. The resulting biphasic solution was extracted with hexane (3 x 15 mL). The combined organic layers were dried over magnesium sulfate, filtered and the solvent was removed under vacuum to obtain the crude product. The crude reaction product was chromatographically purified on silica gel eluting with hexanes followed by 10% ethyl acetate in hexanes to afford 4.3 g of the desired pr...
Embodiment 3
[0116] Preparation of ω-Methylol Polyisobutene Using Boron Trifluoride Ether Complex
[0117] Add 20 g of polyisobutylene (molecular weight 1,000, 80% methylvinylidene), 0.6 g of paraformaldehyde, and 60 mL of anhydrous dichloromethane to a flask equipped with a magnetic stirrer and nitrogen inlet. Boron trifluoride etherate (0.123 mL) was added via syringe in one portion. The reaction mixture was then stirred at room temperature for 16 hours. The mixture was diluted with 40 mL of dichloromethane followed by 2 mL of saturated aqueous ammonium hydroxide. The precipitate was filtered off. The solution was washed with saturated sodium bicarbonate followed by saturated sodium chloride solution. The dichloromethane layer was dried over anhydrous magnesium sulfate. The solvent was removed under vacuum to obtain the crude product. The crude reaction product was chromatographically purified on silica gel eluting with hexanes followed by 10% ethyl acetate in hexanes to afford 6....
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