六溴环十二烷

1,2,5,6,9,10-Hexabromocyclododecane (HBCD)

化合物简介

Hexabromocyclododecane (HBCD or HBCDD) is a brominated flame retardant. It consists of twelve carbon, eighteen hydrogen, and six bromine atoms tied to the ring. Its primary application is in extruded (XPS) and expanded (EPS) polystyrene foam that is used as thermal insulation in the building industry. Other uses are upholstered furniture, automobile interior textiles, car cushions and insulation blocks in trucks, packaging material, video cassette recorder housing and electric and electronic equipment. According to UNEP, “HBCD is produced in China, Europe, Japan, and the USA. The known current annual production is approximately 28,000 tonnes per year. The main share of the market volume is used in Europe and China” (figures from 2009/2010).

基本信息

CAS：3194-55-6
中文别名：六溴环十二烷(HBCD);
英文别名：HBCD HT;1,2,5,6,9,10-hexabromo-cyclododecan;Hexabromocyclododecane SP-75C;1,2,5,6,9,10-Hexabromocyclododecane;CD-75;1,2,5,6,9,10-hexabromocyclodecane;1,2,5,6,9,10-HEXABROMOCYCLODODECANE;HEXABROMOCYCLODODECANE HT;1,2-trans-5,6-cis-9,10-cis-hexabromo-cyclododecane;HBCD;Cyclododecane,1,2,5,6,9,10-hexabromo;
分子式：C12H18Br6
分子量：641.695
精确质量：635.651
Psa：0.0
Logp：6.9216

编号系统

MDL号：MFCD00003716

物化性质

外观与性状：灰白色至米色结晶粉末和块
密度：2.145 g/cm3
沸点：505.2ºC at 760mmHg
熔点：188-191°C
闪点：249.5ºC
折射率：1.598
稳定性：Stable at room temperature in closed containers under normal storage and handling conditions.
储存条件：Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

安全信息

RTECS号：GU2302500
安全说明：S22-S24/25
危险类别码：R36/37/38
WGK Germany：1
危险品运输编码：3077
海关编码：2903890090
危险品标志：Xi

生产方法及用途

生产方法
先合成反,反,顺环十二-1,5,9-三烯(亦见10850) :将钛酸丁酯和二乙基氯化铝加入苯中,在低于55℃的温度下加入丁二烯,经三聚合反应生成反,反,顺环十二-1,5,9三烯(C12H18,[2765-79-9])。然后溴化得到六溴环十二烷。在配置有回流冷器和尾气乍理装置的2000L搪玻璃反应锅内,加入1300L乙醇;278kg反,顺-环二二-1,5,9-三烯和872kg溴。加料温度为15-25℃。在整个加料过程中,保持洲离溴存在,反应物呈红色,反应结束后,赶除过量的臭针生成的六溴环十二烷过滤,精制,可得产品1000kg,收率91%。另一种制法是采用三氯化铝作催化剂。在800份环十二-1,5,9-三烯和1500份乙醇中,于15-25℃加入150份三氯化铝,然后在25-30℃于2h内加入2400份溴,在室温下搅拌反应5h,然后过滤。滤饼用200份乙醇和2%碳酸氢钠洗涤,得到的六溴环十二烷收率为86%,若在乙醇溶剂中添加卤代烃,可以抑制树脂状物质的生成。
用途
氯吡嘧磺隆中间体。