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六溴环十二烷

英文名称: 1,2,5,6,9,10-Hexabromocyclododecane (HBCD)

CAS号:3194-55-6 分子式:C12H18Br6 分子量:641.69500

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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).
HBCD's toxicity and its harm to the environment are currently discussed. HBCD can be found in environmental samples such as birds, mammals, fish and other aquatic organisms as well as soil and sediment. On this basis, on 28 October 2008 the European Chemicals Agency decided to include HBCD in the SVHC list, Substances of Very High Concern, within the Registration, Evaluation, Authorisation and Restriction of Chemicals framework. On 18 February 2011, HBCD was listed in the Annex XIV of REACH and hence is subject to Authorisation. HBCD can be used until the so-called “sunset date” (21 August 2015). After that date, only authorised applications will be allowed in the EU. HBCD has been found widely present in biological samples from remote areas and supporting evidences for its classification as Persistent, Bioaccumulative and Toxic (PBT) and undergoes long-range environmental transportation. In July 2012, an EU harmonised classification and labelling for HBCD entered into force. HBCD has been classified as a category 2 for reproductive toxicity. Since August 2010 hexabromocyclododecanes are included in the EPA's List of Chemicals of Concern. On May 2013 the Stockholm Convention on Persistent Organic Pollutants (POPs) decided to include HBCD in the Convention’s Annex A for elimination, with specific exemptions for expanded and extruded polystyrene in buildings needed to give countries time to phase-in safer substitutes. HBCD is listed for elimination, but with a specific exemption for expanded polystyrene (EPS) and extruded polystyrene (XPS) in buildings. Countries may choose to use this exemption for up to five years after the request for exemption is submitted. Japan was the first country to implement a ban on the import and production of HBCD effective in May 2014.
Because HBCD has 16 possible stereo-isomers with different biological activities, the substance poses a difficult problem for manufacture and regulation. The HBCD commercial mixture is composed of three main diastereomers denoted as alpha (α-HBCD), beta (β-HBCD) and gamma (γ-HBCD) with traces of others. A series of four published in vivo mice studies were conducted between several federal and academic institutions to characterize the toxicokinetic profiles of individual HBCD stereoisomers. The predominant diastereomer in the HBCD mixture, γ-HBCD, undergoes rapid hepatic metabolism, fecal and urinary elimination, and biological conversion to other diastereomers with a short biological half-life of 1–4 days. After oral exposure to the γ-HBCD diastereomer, β-HBCD was detected in the liver and brain, and α-HBCD and β-HBCD was detected in the fat and feces with multiple novel metabolites identified - monohydroxy-pentabromocyclododecane, monohydroxy-pentabromocyclododecene, dihydroxy-pentabromocyclododecene, and dihydroxy-pentabromocyclododecadiene. In contrast, α-HBCD is more biologically persistent, resistant to metabolism, bioaccumulates in lipid-rich tissues after a 10-day repeated exposure study, and has a longer biological half-life of up to 21 days; only α-HBCD was detected in the liver, brain, fat and feces with no stereoisomerization to γ-HBCD or β-HBCD and low trace levels of four different hydroxylated metabolites were identified. Developing mice had higher HBCD tissue levels than adult mice after exposure to either α-HBCD or γ-HBCD indicating the potential for increased susceptibility of the developing young to HBCD effects. The reported toxicokinetic differences of individual HBCD diastereoisomers have important implications for the extrapolation of toxicological studies of the commercial HBCD mixture to the assessment of human risk.
Structures of the six (out of 16 possible) hexabromocyclododecane isomers that are present in the technical product at > 1%

基本信息

中文名称 六溴环十二烷 英文名称 1,2,5,6,9,10-Hexabromocyclododecane (HBCD)
中文别名

六溴环十二烷(HBCD);

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英文别名

1,2,5,6,9,10-hexabromo-cyclododecan; CD-75; 1,2,5,6,9,10-HEXABROMOCYCLODODECANE; Cyclododecane,1,2,5,6,9,10-hexabromo; HBCD HT; 1,2-trans-5,6-cis-9,10-cis-hexabromo-cyclododecane; HEXABROMOCYCLODODECANE HT; Hexabromocyclododecane SP-75C; 1,2,5,6,9,10-hexabromocyclodecane; HBCD;

查看更多英文别名
CAS号 3194-55-6 分子式 C12H18Br6
分子量 641.69500 精确质量 635.65100
PSA 0.00000 LOGP 6.92160

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
海关编码:
2903890090
危险品运输编码:
3077
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。

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国家名称 海关编码 海关数据更新时间 操作
中国 2903890090 2019-03 申报要素
美国 2903897000 2019-03 概述
印度 29038900 2019-03 概述
欧盟 29038990 2019-03 概述
英国 2903899090 2019-03 概述
日本 290389099 2019-03 概述
韩国 2903590000 2019-03 概述
加拿大 2903890000 2019-03 概述

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六溴环十二烷

CAS号:3194-55-6 分子式:C12H18Br6 分子量:641.69500

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