Halide flame retardants Chemical Properties Uses Production method
ChemicalBook > CAS DataBase List > 1,2,5,6,9,10-Hexabromocyclododecane

1,2,5,6,9,10-Hexabromocyclododecane

Halide flame retardants Chemical Properties Uses Production method
Product Name
1,2,5,6,9,10-Hexabromocyclododecane
CAS No.
3194-55-6
Chemical Name
1,2,5,6,9,10-Hexabromocyclododecane
Synonyms
HBCD;ALPHA-HEXABROMOCYCLODODECANE;SAYTEX HP-900;XPS master batch;HBCD-EPS FLAME RETARDENT;Hydroxybutyl-B-cyclodextrin;HBBCD;CD-75;HBCD HT;FR1206 )
CBNumber
CB7363333
Molecular Formula
C12H18Br6
Formula Weight
641.7
MOL File
3194-55-6.mol
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1,2,5,6,9,10-Hexabromocyclododecane Property

Melting point:
188-191 °C
Boiling point:
505.2±50.0 °C(Predicted)
Density 
2.145±0.06 g/cm3(Predicted)
solubility 
acetone: soluble25mg/mL, clear, colorless to light yellow
BRN 
1911324
InChIKey
DEIGXXQKDWULML-UHFFFAOYSA-N
CAS DataBase Reference
3194-55-6(CAS DataBase Reference)
EPA Substance Registry System
1,2,5,6,9,10-Hexabromocyclododecane (3194-55-6)
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Safety

Hazard Codes 
Xi,N,Xn
Risk Statements 
36/37/38-64-50/53-63
Safety Statements 
22-24/25-61-60-36/37-53
RIDADR 
3077
WGK Germany 
1
RTECS 
GU2302500
3-9
HS Code 
29038900
Hazardous Substances Data
3194-55-6(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H361Suspected of damaging fertility or the unborn child

H362May cause harm to breast-fed children

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P263Avoid contact during pregnancy/while nursing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
51691
Product name
1,2,5,6,9,10-Hexabromocyclododecane
Purity
analytical standard
Packaging
50mg
Price
$62.1
Updated
2022/05/15
Sigma-Aldrich
Product number
144762
Product name
1,2,5,6,9,10-Hexabromocyclododecane
Purity
95%
Packaging
25g
Price
$23.7
Updated
2022/05/15
TCI Chemical
Product number
H0544
Product name
1,2,5,6,9,10-Hexabromocyclododecane
Purity
>97.0%(T)
Packaging
25g
Price
$22
Updated
2022/04/27
TRC
Product number
H290740
Product name
1,2,5,6,9,10-Hexabromocyclododecane
Packaging
10g
Price
$105
Updated
2021/12/16
Matrix Scientific
Product number
099703
Product name
1,2,5,6,9,10-Hexabromocyclododecane
Purity
95+%
Packaging
100g
Price
$152
Updated
2021/12/16
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1,2,5,6,9,10-Hexabromocyclododecane Chemical Properties,Usage,Production

Halide flame retardants

Halide fire retardant is a kind of commonly-used organic fire retardants. The order of efficacy on fire retardancy for halogen element is I> Br> Cl> F. Because of that the C-F bond is very stable and is difficult to be broken down, so it has a poor fire-retardant effect. Moreover, owing to the poor thermal stability of the sulfonated, therefore, the industry usually applies chloride or bromide as the preferred fire retardant. The order of the fire-retardant effect of different kinds of organic compounds is that: aliphatic> cycloaliphatic> aromatic. However, the aliphatic compound has a poor thermal stability with the processing temperature should not exceed 205 ℃. In contrast, the thermal stability of the aromatic is relative good with the processing temperatures being up to 315 ℃. For the fire-retardant halide, they usually have relative high halogen content. Common halide fire retardants are as follows:
Chlorinated paraffin is made from the direct chlorination of wax. It has a good chemical stability with low cost and a relative wide application. It is often used in combination with antimony trioxide.
Full kelevan decane is generally produced by as following: first chloride the cyclopentadiene to yield hexachlorocyclopentadiene; then further go through dimerization under the catalysis of anhydrous aluminum chloride to obtain the final product.
Hexabromocyclododecane belongs cycloaliphatic class fire-retardant and is mainly applied to the fire retardancy in polypropylene, polystyrene and polypropylene fibers. It is made as following: first put butadiene for trimerization, to first make cyclododecyl-1, 5, 9-triene, and then further have addition reaction with bromine in the carbon tetrachloride solution to obtain the 1, 2, 5, 6, 9, 10-Hexabromocyclododecane.
Hexabromobenzene is produced from the bromination reaction of benzene with bromine in the tetrachloride solution with iron and sulfur as the catalyst. It is usually mixed with antimony trioxide.
The current applied brominates fire-retardants include mainly tetrabromoethane, tetrabromo phenol disulfide, decabromodiphenyl ether, decabromodiphenyl, isocyanate-tris (2,6-dibromopropyl) ester, 2, 2-[4-(2,3-dibromopropyl-3,5-dibromophenyl] propane, hexabromocyclododecane decane, hexabromobenzene, tetrabromobisphenol A, octabromodiphenyl ethers, tetrabromodiphenyl ether, poly-dibromo-phenylene oxide, bis (tribromophenoxy) ethane, tribromophenol, ethylene bis tetrabromophthalimide dicarboxamide, pentabromobenzyl polyacrylate and so on. They respectively can be applied to plate of integrated circuit, unsaturated polyester, epoxy resin, polystyrene resin, chloroprene rubber, styrene-butadiene rubber, natural rubber, polyester resins, polypropylene, polyethylene wires, polyurethane, fiber, ABS resin, nylon, polybutylene terephthalate and so on.
Put into the polystyrene (PS) (fire retardants), hexabromocyclododecane (fire retardants) and talc from the extruder into the feed section, and pump into the remaining foaming agent between the compression section and metering section to obtain a high compression-resistant foam sheet with a density of 34.7kg/m3 and water absorption of 0.09%.

Chemical Properties

It is white crystals and have two isomers with the melting point of low melting point type being 167-168 ℃ and high melting point type is 195-196 ℃. It has a good stability upon heat and ultraviolet light.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Uses

1. It can be used in smoldering, for polystyrene foamed plastics, polypropylene and polyester, acrylic, polypropylene and other fabrics as smoldering finishing agent.
2. It is mainly used for thermoplastic and thermosetting polymers which have fire retardant requirements. It is particularly suitable for extrusion of foaming polystyrene.
3. It is used for the fire-retardant polystyrene of polypropylene plastics and fibers. It can also be used for the fire retardancy of finishing and leather double-sided coat after the fire-retardancy of polyester fabric. When used as additive fire retardants, it is especially suitable for polystyrene, unsaturated polyester, polycarbonate, polypropylene, synthetic rubber or the like.

Production method

First synthesize trans, trans, cis-cyclododecene triene (see also 10850): add butyl titanate and diethyl aluminum chloride together into benzene; further add butadiene at a temperature below 55 ℃ and make trans, trans, cis-cyclododecene-1,5,9-triene (C12H18, [2765-79-9]) through Tri-polymerization reaction. Then further obtain hexabromocyclododecane through bromination. To a 2000 L enameled pot reactor equipped with a reflux cooler and exhaust processing apparatus 2000L, add 1300 L of ethanol and 278 kg of trans, cis-ring two two-1, 5, 9-triene and 872 kg of bromine with the feed temperature being 15-25 ℃. During the entire process of adding materials, upon maintaining the presence of free bromine ion, the reaction color was red. After the reaction, remove the excess amount of bromine needle and have generated hexabromocyclododecane be subject to filtration, refinement to obtain 1000 kg of products with the yield being 91%. Another approach is applying aluminum chloride as the catalyst. To 800 parts of the Cyclododecyl-1, 5, 9-triene and 1500 parts of ethanol, add 150 parts of aluminum trichloride at 15-25 ℃m, followed by the addition of 2400 parts of bromine at 25-30 ℃ within 2h; Stir and have the reaction for 5 hour at room temperature and then filter. The filtered cake was washed by 200 parts of ethanol and 2% sodium bicarbonate to obtain hexabromocyclododecane with the yield being 86%. Moreover, the supplement of halogenated hydrocarbons to the ethanol can further inhibit the formation of resinous substance.

Chemical Properties

off-white to beige crystalline powder and chunks

Uses

1,2,5,6,9,10-Hexabromocyclododecane(HBCD) was used to compare the efficiency of different advanced extraction techniques for the recovery of brominated flame retardants from styrenic polymers. It was used to study the kinetics of the thermal and photolytic segregation of HBCD using HPLC.

Definition

ChEBI: 1,2,5,6,9,10-hexabromocyclododecane is a bromoalkane consisting of cyclododecane bearing six bromo substituents at positions 1, 2, 5, 6, 9 and 10. It has a role as a neurotoxin, a persistent organic pollutant and a xenobiotic. It is a bromoalkane, a bromohydrocarbon and a brominated flame retardant.

General Description

1,2,5,6,9,10-Hexabromocyclododecane(HBCD) is a brominated flame retardant. It is used in the textile industry and polystyrene foam manufacturing. Electrochemical reduction of HBCD at carbon and silver cathodes has been studied using cyclic voltammetry and controlled-potential electrolysis.

Biochem/physiol Actions

1,2,5,6,9,10-Hexabromocyclododecane enhances the diet-induced body weight gain and metabolic dysfunction via disruption of lipid and glucose homeostasis in mice fed normal diet or high-fat diet.

1,2,5,6,9,10-Hexabromocyclododecane Preparation Products And Raw materials

Raw materials

Preparation Products

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1,2,5,6,9,10-Hexabromocyclododecane Suppliers

Tianjin Zhongxin Chemtech Co., Ltd.
Tel
022-66880623
Fax
86(0)22-66880086
Email
sales@tjzxchem.com
Country
China
ProdList
613
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60
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
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81
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
19172
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64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
XiaoGan ShenYuan ChemPharm co,ltd
Tel
15527768850
Email
1791901229@qq.com
Country
China
ProdList
8843
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52
Shandong Xiya Chemical Co., Ltd
Tel
4009903999 13355009207
Fax
0539-6365991
Email
3007715519@qq.com
Country
China
ProdList
18738
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57
Sichuan Kulinan Technology Co., Ltd
Tel
400-1166-196 18981987031
Fax
028-84555506 800101999
Email
cdhxsj@163.com
Country
China
ProdList
11707
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57
China Langchem Inc.
Tel
0086-21-58956006
Fax
0086-21-58956100
Country
China
ProdList
7811
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57
Tianjin heowns Biochemical Technology Co., Ltd.
Tel
400 638 7771
Email
sales@heowns.com
Country
China
ProdList
14435
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57
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
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View Lastest Price from 1,2,5,6,9,10-Hexabromocyclododecane manufacturers

Henan Fengda Chemical Co., Ltd
Product
1,2,5,6,9,10-Hexabromocyclododecane 3194-55-6
Price
US $100.00-1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2023-12-25
Henan Aochuang Chemical Co.,Ltd.
Product
1,2,5,6,9,10-Hexabromocyclododecane 3194-55-6
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1ton
Release date
2022-10-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
1,2,5,6,9,10-Hexabromocyclododecane 95% 3194-55-6
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27

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