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Study On The Synthesis Of Bis-(4-allyloxy-3, 5-dibromophenyl) Sulfone

Posted on:2007-07-09Degree:MasterType:Thesis
Country:ChinaCandidate:L Y YouFull Text:PDF
GTID:2121360212480409Subject:Applied Chemistry
Abstract/Summary:PDF Full Text Request
ATBS (bis-(4-allyloxy-3, 5-dibromophenyl) sulfone) is a very valuable flame retardant or an intermediate for the production of a flame retardant. The preparations of ATBS by etherifying TBS (bis-(4-hydroxy-3, 5-dibromophenyl)sulfone) with allyl chloride in the presence of alkali media under atmospheric pressure or low-pressure were investigated in the present study respectively. Several kinds of catalysts were chosen during the process of study, including NaBr, CTAB (cetyltrimethylammonium bromide) and several surface-active agents commonly used in industry, such as DBS (Sodium dodecylbenzenesulfonate), OP-10 (alkylphenol polyethoxylates), OS-15 (fatty alcoholpolyoxyethylene ether) and Tween-80 (Polyoxyethylene sorbitan monooleate). The catalyst amount, reaction time, allyl chloride amount, and other factors influencing the yield and purity of ATBS were particularly evaluated.ATBS with high yield and purity can be obtained through three methods by allyl-etherizing TBS with dropping allyl chloride under atmospheric pressure. The highest yields (corresponding purities) of ATBS gained through the methods using alkali metal bromide, quaternary ammonium salt and without organic solvents were 99.81%(97.42%), 97.55%(95.57%) and 99.79%(93.21%) , respectively.As for the process under low-pressure(0.3~0.4MPa, 8h, 80~90℃), when NaBr was chosen as the catalyst, the yields and purities of ATBS ranged respectively from 96.20% to 98.10% and 85.64% to 96.42% as the amount of NaBr ranged from 14 g/mol TBS to 106 g/mol TBS; 87.50% to 84.20% and 49.76% to 87.52% as the reaction time was from 2 to 10 h; 94.60% to 97.40% and 79.93% to 97.85% as the amount of allyl chloride varied from 8ml to 15ml. When CTAB was chosen as the catalyst, the yields and purities of ATBS ranged respectively from 95.80% to 97.40% and 97.57% to 98.48% as the amount of the catalyst ranged from 0.18 g/mol TBS to 36.4 g/mol TBS. The highest yield (purity) of ATBS gained were 98.10%(96.42%) (NaBr used), 97.40%(98.48%) (CTAB), 99.70%(94.73%) (DBS), 97.40%(93.96%) (OP-10), 97.80%(96.94%) (OS-15) and 91.37%(93.36%) (Tween-80), respectively.
Keywords/Search Tags:flame retardant, bis-(4-allyloxy-3, 5-dibromophenyl) sulfone, bis-(4-hydroxy-3, 5-dibromophenyl) sulfone, etherization, surface-active agents, allyl chloride
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