3194-55-6 Usage
Uses
1. Used in Polymer and Plastic Industry:
1,2,5,6,9,10-Hexabromocyclododecane is used as a flame retardant for thermoplastic and thermosetting polymers that require fire resistance. It is particularly suitable for the extrusion of foaming polystyrene and is effective in smoldering applications for materials such as polystyrene foamed plastics, polypropylene, polyester, acrylic, and other fabrics.
2. Used in Textile Industry:
In the textile industry, HBCD serves as a flame retardant for various fabrics, enhancing their fire safety. It is used for the fire-retardant treatment of polystyrene of polypropylene plastics and fibers, as well as for the finishing and leather double-sided coat after the fire-retardancy of polyester fabric.
3. Used in Advanced Extraction Techniques:
1,2,5,6,9,10-Hexabromocyclododecane has been utilized in studies comparing the efficiency of different advanced extraction techniques for the recovery of brominated flame retardants from styrenic polymers. This application aids in understanding and improving the processes for removing such compounds from materials.
4. Used in Research and Development:
HBCD is also used in research to study the kinetics of thermal and photolytic segregation, employing techniques such as high-performance liquid chromatography (HPLC). This research contributes to the understanding of the compound's behavior under various conditions, which can be crucial for its application and safety.
5. Used in Electrochemical Reduction Studies:
The electrochemical reduction of HBCD at carbon and silver cathodes has been studied using cyclic voltammetry and controlled-potential electrolysis. This research provides insights into the compound's reactivity and potential applications in electrochemical processes.
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%.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 3194-55-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,1,9 and 4 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 3194-55:
(6*3)+(5*1)+(4*9)+(3*4)+(2*5)+(1*5)=86
86 % 10 = 6
So 3194-55-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H18Br6/c13-7-1-2-8(14)10(16)5-6-12(18)11(17)4-3-9(7)15/h7-12H,1-6H2/t7-,8-,9-,10+,11+,12+
3194-55-6Relevant articles and documents
Electrophilic bromination in flow: A safe and sustainable alternative to the use of molecular bromine in batch
Van Kerrebroeck, Reinout,Naert, Pieter,Heugebaert, Thomas S.A.,D’hooghe, Matthias,Stevens, Christian V.
, (2019/06/10)
Bromination reactions are crucial in today’s chemical industry since the versatility of the formed organobromides makes them suitable building blocks for numerous syntheses. However, the use of the toxic and highly reactive molecular bromine (Br2) makes these brominations very challenging and hazardous. We describe here a safe and straightforward protocol for bromination in continuous flow. The hazardous Br2 or KOBr is generated in situ by reacting an oxidant (NaOCl) with HBr or KBr, respectively, which is directly coupled to the bromination reaction and a quench of residual bromine. This protocol was demonstrated by polybrominating both alkenes and aromatic substrates in a wide variety of solvents, with yields ranging from 78% to 99%. The protocol can easily be adapted for the bromination of other substrates in an academic and industrial environment.
Method for preparing hexabromocyclododecane
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Paragraph 0023; 0024; 0025; 0026, (2018/09/08)
The invention discloses a method for preparing hexabromocyclododecane. A 1-methyl-3-propanesulfonic imidazole disulfate ion liquid catalyst is used. Compared with the hexabromocyclododecane prepared by a method in the prior art, the hexabromocyclododecane prepared by the method provided by the invention has the advantage that the melting point is improved and can reach 197 DEG C or higher. The method provided by the invention has the advantages that the cost is low; the operation is simple; safety and environment-friendly effects are achieved; the industrial application is easy.
New process for producing hexabromocyclododecane
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Paragraph 0024; 0025; 0027, (2018/09/13)
The invention discloses a new process for producing hexabromocyclododecane. 1-butyl-3-propanesulfonic acid imidazolium hexafluorophosphate ionic liquid catalyst is adopted. Compared with hexabromocyclododecane prepared with the method in the prior art, hexabromocyclododecane prepared with the new process has higher melting point up to 195 DEG C or higher. The method has the advantages of being lowin cost, easy to operate, safe and environmentally friendly and facilitates industrial application.
A preparation method of double-ring (by machine translation)
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Paragraph 0016; 0017, (2017/08/25)
The invention discloses a method for preparing-ring cyclododecane, including brominated, washing and separating, drying three steps. Bromide is the raw material ring dodecatrienoic and bromine are respectively drop adding isobutyl alcohol and dichloroethane in the mixed solvent, bromine and ring dodecatrienoic molar ratio of 3.05 - 3.08: 1. Dropping process is divided into three sections of heating up to 50 °C ± 2 °C, the total reaction time is 3 - 4 hours; washing and separating, in the bromination reaction compatibility of the separated solid phase into the dichloroethane with preparation of isobutyl alcohol mixed solvent, stirring and mixing and then separating the solid phase, then adding ethanol washing 2 times, filtered and the solid phase. The separation is washing the separated solid phase in 80 °C ± 2 °C drying, to obtain white solid powder product. The present invention provides a method for preparing cyclododecatriene, the method of washing of the solvent, the product is entrained will affect the melting point of the fully impurities not bromide, the product purity, make the product melting point rises. (by machine translation)
Preparation process for hexabromocyclododecane
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Paragraph 0015; 0016; 0023; 0024, (2018/02/04)
The invention discloses a preparation process for hexabromocyclododecane and belongs to the field of production of chemical products. The preparation process includes the steps of bromination, separation, drying and powder screening. According to the step of bromination, bromine and cyclododecatriene are added into a mixed solvent of isobutanol and chloroform dropwise for a reaction, the reaction dropwise-adding speed is controlled, and heat preservation curing is conducted after bromine and cyclododecatriene are added dropwise; the mass ratio of isobutanol to isobutanol in the mixed solvent is (0.8-1.0):1; the molar ratio of added bromine to added cyclododecatriene is (3.12-3.19):1, and the mass ratio of bromine to the solvent is 1:1.7. According to the step of separation, the material obtained after the reaction is subjected to suction filtration, the material obtained after suction filtration is poured into a centrifuge, and the material obtained after centrifugation is sequentially subjected to alkali washing and water washing. The material obtained after separation and water washing is dried and subjected to powder screening, and the product is obtained.
High content of isomers of hexabromocyclododecane γ process for the preparation of
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Paragraph 0028-0032, (2016/10/08)
The invention relates to a method for preparing hexabromocyclododecane. A water-containing mixed solvent is used as a reaction medium, wherein the mixed solvent comprises hydrochloric ether and low molecular fatty alcohol with carbon number smaller than 10; inorganic acid salt or organic acid salt is added to the water-containing mixed solvent, so that the water-containing mixed solvent achieves a dissolved saturation condition; the permissible moisture content in the mixed solvent can be increased to 10wt%. The selectivity and the product yield of the hexabromocyclododecane gamma isomer are improved by utilizing the preparation method disclosed by the invention; and moreover, the product grain size is small and the bulk density is low, so that the dispersion in the polymer is facilitated.
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