1163-19-5

Basic information

• Product Name: Decabromodiphenyl oxide
• Synonyms: 1,1’-oxybis(2,3,4,5,6-pentabromo-benzen;1,1’-oxybis[2,3,4,5,6-pentabromo-benzen;berkflamb10e;br55n;bromkal82-0de;bromkal82-ode;bromkal83-10de;dbdpo
• CAS NO: 1163-19-5
• Molecular Formula: C₁₂Br₁₀O
• Molecular Weight: 959.17
• EINECS: 214-604-9
• Product Categories: Organics;Biphenyl & Diphenyl ether;Diphenyl Ethers (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Flame retardant series
• Mol File: 1163-19-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 425°C
• Flash Point: -12 °C
• Appearance: off-white powder with a chemical odor
• Density: 3 g/cm3
• Vapor Pressure: 0Pa at 21℃
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: 2-8°C
• Solubility: <0.0001mg/l
• Water Solubility: <0.1 g/100 mL at 20℃
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 2188438
• CAS DataBase Reference: Decabromodiphenyl oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Decabromodiphenyl oxide(1163-19-5)
• EPA Substance Registry System: Decabromodiphenyl oxide(1163-19-5)

Safety Data

• Hazard Codes: Xn,Xi,N,F
• Statements: 20/21/22-67-65-63-50/53-48/20-38-11
• Safety Statements: 36/37-62-61-60-16
• RIDADR: 3152
• WGK Germany: 1
• RTECS: KN3525000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: II
• Hazardous Substances Data: 1163-19-5(Hazardous Substances Data)

Usage

Chemical Properties

Decabromodiphenyl Oxide (DBDPO) is a white to off-white or light yellow powder. Almost insoluble in all solvents. Good thermal stability. Heated to 354 ℃, weight loss 5%. It is a non-toxic and non-polluting flame retardant.

Uses

Decabromodiphenyl ether is a brominated flame retardant that is used in conjunction with antimony trioxide in high impact polystyrene. DecaBDE is used as an additive flame retardant, and has a variety of applications including in plastics/polymers/composites, textiles, adhesives, sealants, coatings and inks. DecaBDE containing plastics are used in housings of computers and TVs, wires and cables, pipes and carpets. Adverse effects are reported for soil organisms, birds, fish, frog, rat, mice and humans. One of the new POPs under the Stockholm Convention

Definition

ChEBI: Decabromodiphenyl ether is a polybromodiphenyl ether that is diphenyl ether in which all of the hydrogens have been replaced by bromines. It has a role as a neurotoxin.

Application

Decabromodiphenyl oxide is an unreactive, additive flame retardant widely used for its thermal stability and its low cost in thermoplastic resins, thermoset resins, textiles and adhesives. The major applications are in high impact polystyrene, glass reinforced thermoplastic polyester and moulding resins, low density polyethylene extrusion coatings, polypropylene (homo- and copolymers), acrylonitrile butadiene styrene rubber, nylon and polyvinyl chloride.

Preparation

Decabromodiphenyl ether can be synthesized by reacting diphenyl ether with bromine in the presence of halogenated catalyst (iron powder, etc.). The diphenyl ether is dissolved in the solvent, the catalyst is added, and then bromine is added to carry out the reaction. After the reaction, filter, wash and dry to obtain decabromodiphenyl ether. Commonly used solvents are dibromoethane, dichloroethane, dibromomethane, carbon tetrachloride, tetrachloroethane and the like.

General Description

White to off-white powder with a chemical odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Decabromodiphenyl oxide is incompatible with strong oxidizers .

Fire Hazard

Flash point data for Decabromodiphenyl oxide are not available; however, Decabromodiphenyl oxide is probably combustible.

Safety Profile

Questionable carcinogen with experimental neoplastigenic data. Experimental reproductive effects. Used as a flame retardant for thermoplastics. When heated to decomposition it emits toxic fumes of Br-. See also ETHERS and BROMIDES

Potential Exposure

It is used as a fire retardant for thermoplastics and man-made fibers.

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required. UN3152 Polyhalogenated biphenyls, solid or Polyhalogenated ter- phenyls, solid, Hazard class: 9; Labels: 9-Miscellaneous hazardous material.

Incompatibilities

Incompatible with strong oxidizers (chlo- rates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides. Ethers have a tendency to form unstable and explosive peroxides.

InChI:InChI:1S/C12Br10O/c13-1-3(15)7(19)11(8(20)4(1)16)23-12-9(21)5(17)2(14)6(18)10(12)22

Synthetic route

diphenylether (101-84-8) → 2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5)

Conditions	Yield
With aluminum tri-bromide; bromine for 3h; Heating;	98%
With aluminum tri-bromide; bromine
Stage #1: diphenylether With bromine at 25 - 58℃; for 1.66667 - 2.13333h; Stage #2: With bromine; aluminum (III) chloride at 55 - 60℃; for 6.38333 - 6.5h; Product distribution / selectivity;

diphenylether (101-84-8) + bromine (7726-95-6) + aluminium bromide (7727-15-3) → 2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5)

diphenylether (101-84-8) → 2,2',3,3',4,5,5',6,6'-nonabromodiphenyl ether (437701-78-5) + nonabromodiphenyl ether (63387-28-0) + BDE-207 (437701-79-6) + 2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5)

Conditions	Yield
With bromine; aluminum (III) chloride at 55 - 61℃; for 6.25h; Product distribution / selectivity;	A n/a B 0.24 %Chromat. C n/a D 99.54 %Chromat.
Stage #1: diphenylether With bromine for 0.416667 - 1.41667h; Heating / reflux; Stage #2: With bromine; aluminum (III) chloride at 56.1 - 59℃; for 7.13333 - 9.78333h; Product distribution / selectivity;	A n/a B 0.031 - 0.205 %Chromat. C n/a D 99.90 - 99.95 %Chromat.
Stage #1: diphenylether With bromine at 40℃; Stage #2: With bromine; aluminum (III) chloride at 56.9 - 60.4℃; for 1.83333 - 1.85h; Product distribution / selectivity;	A n/a B 0.181 - 0.220 %Chromat. C n/a D 99.634 - 99.696 %Chromat.

diphenylether (101-84-8) → nonabromodiphenyl ether (63387-28-0) + 2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5)

Conditions	Yield
Stage #1: diphenylether With bromine at 40℃; Stage #2: With bromine; aluminum (III) chloride at 56.5 - 78.4℃; under 1385.82 - 1458.22 Torr; for 3.65 - 4.36667h; Product distribution / selectivity;	A 0.233 - 0.526 %Chromat. B 99.44 - 99.70 %Chromat.

diphenylether (101-84-8) → 2,2',3,3',4,5,5',6,6'-nonabromodiphenyl ether (437701-78-5) + BDE-207 (437701-79-6) + C12Br9ClO (918947-03-2) + C12Br9ClO + C12Br9ClO + 2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5)

Conditions	Yield
With bromine; bromine chloride; aluminum (III) chloride at 55 - 57℃; for 2.23333h; Product distribution / selectivity; Heating / reflux;	A n/a B n/a C n/a D n/a E n/a F 97.2 %Chromat.

diphenylether (101-84-8) → 2,2',3,3',4,5,5',6,6'-nonabromodiphenyl ether (437701-78-5) + nonabromodiphenyl ether (63387-28-0) + BDE-207 (437701-79-6) + C12Br9ClO (918947-03-2) + C12Br9ClO + C12Br9ClO + 2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5)

Conditions	Yield
With bromine; bromine chloride; aluminum (III) chloride at 56℃; for 0.0666667h; Product distribution / selectivity; Heating / reflux;	A n/a B 0.14 %Chromat. C n/a D n/a E n/a F n/a G 99.29 %Chromat.

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → diphenylether (101-84-8)

Conditions	Yield
With sodium hydroxide; palladium diacetate; triphenylphosphine In isopropyl alcohol at 81.9℃; for 5h; Product distribution; Mechanism; other aromatic mono- and polyhalides, var. solvents, transition metal salt, ligands, temperature, and reaction time;	92%
With methanol; gold; hydrogen; caesium carbonate at 100℃; under 3800.26 Torr; for 96h;	89%
With cadmium selenide; triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; Irradiation; Sealed tube;	54%
With 2 wt.% Pd/TiO2 In tetrahydrofuran; methanol for 1h; Catalytic behavior; Kinetics; Reagent/catalyst; UV-irradiation; Inert atmosphere; Darkness;	15.7%
With borane-ammonia complex In water; isopropyl alcohol at 50℃; for 12h; Sealed tube;	97 %Chromat.

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → 1,1,2,2-tetrabromoethene (79-28-7) + pentabromobenzene (608-90-2) + hexabromobenzene (87-82-1) + hexabromobenzofuran (118647-51-1)

Conditions	Yield
thermolysis; Further byproducts given;	A n/a B 0.5% C 5% D 0.1%

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → hexabromo-1,3-butadiene (53978-00-0) + pentabromobenzene (608-90-2) + hexabromobenzene (87-82-1) + hexabromobenzofuran (118647-51-1)

Conditions	Yield
thermolysis; Further byproducts given;	A n/a B 0.5% C 5% D 0.1%

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → pentabromobenzene (608-90-2) + hexabromobenzene (87-82-1) + hexabromobenzofuran (118647-51-1) + octabromostyrene (118647-52-2)

Conditions	Yield
thermolysis; Further byproducts given;	A 0.5% B 5% C 0.1% D n/a

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → 1,1,2,2-tetrabromoethene (79-28-7) + hexabromo-1,3-butadiene (53978-00-0) + pentabromobenzene (608-90-2) + hexabromobenzene (87-82-1) + hexabromobenzofuran (118647-51-1) + octabromostyrene (118647-52-2) + pentabromobenzofuran, tribromophenol

Conditions	Yield
Product distribution; thermolysis;	A n/a B n/a C 0.5% D 5% E 0.1% F n/a G n/a

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → 2,3,7,8-Tetrabromodibenzofuran (67733-57-7) + 2,3,7,8-tetrabromodibenzodioxin (50585-41-6)

Conditions	Yield
at 400℃; thermolysis; Further byproducts given;	A 4.5 B 4.0 (unit not given)
at 400℃; thermolysis; Further byproducts given;	A 4.5 (unit not given) B 4.0
With antimony(III) trioxide; polybutylene terephtalate at 400℃; Product distribution; thermolysis; similar results with various plastics containing the title compound and other brominated aromatic compounds used as flame retardants(tetrabromobisphenol A, hexabromocyclododecane);	A 4.5 (unit not given) B 4.0 (unit not given)

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → 2,2',3,3',4,5,5',6,6'-nonabromodiphenyl ether (437701-78-5) + nonabromodiphenyl ether (63387-28-0) + BDE-207 (437701-79-6)

Conditions	Yield
In methanol; water for 1.66667h; Kinetics; Quantum yield; Further Variations:; Solvents; Reagents; UV-irradiation;
With 2-oxo-propionic acid; sodium hydroxide In tetrahydrofuran; methanol; water Kinetics; Reagent/catalyst; Photolysis; Inert atmosphere;
With 2 wt.% Pd/TiO2 In tetrahydrofuran; methanol Reagent/catalyst; UV-irradiation; Inert atmosphere; Darkness;

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → nonabromodiphenyl ether (63387-28-0) + BDE-207 (437701-79-6) + 2,2',4,4',5,5'-hexabromobiphenyl ether + 2,3,4,6-tetrabromophenyl 2,4,5-tribromophenyl ether (207122-16-5)

Conditions	Yield
With honey In acetone at 60℃; for 672h; Darkness;

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → 1,2,3,4,6,7,8-heptabromodibenzofuran + nonabromodiphenyl ether (63387-28-0)

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Pschor Arylation; Electrochemical reaction;

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) + bismuth(III) oxide (1304-76-3) → bismuth oxybromide

Conditions	Yield
With air for 2h; Milling; Green chemistry;

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → 2,2′,3,4,4′,5,6,6′-octabromodiphenylether + 2,3,3',4,4',5,5',6-octabromodiphenyl ether + 2,2',3,3',4,4',6,6'-octabromodiphenyl ether + 2,2',3,3',4,4',5,6'-octabromodiphenyl ether + 2,2',3,3',4,4',5,5'-octabromodiphenyl ether + 2,2',3,3',4,4',5,6-octabromodiphenyl ether + 2,2',3,3',4,5,5',6'-octabromodiphenyl ether + 2,2',3,3',5,5',6,6'-octabromodiphenyl ether + 2,2',3,3',4,5,5',6-octabromodiphenyl ether + 2,2′,3,3′,4,5′,6,6′-octabromodiphenyl ether + 2,2',3,4,4',5,5',6-octabromodiphenyl ether

Conditions	Yield
With 2 wt.% Pd/TiO2 In tetrahydrofuran; methanol for 0.0333333h; UV-irradiation; Inert atmosphere; Darkness;

...Expand

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → 2,2′,3,4,4′,5,6,6′-octabromodiphenylether + 2,2',3,3',4,4',6,6'-octabromodiphenyl ether + 2,2',3,3',4,4',5,6'-octabromodiphenyl ether + 2,2',3,3',4,4',5,5'-octabromodiphenyl ether + 2,2',3,3',4,4',5,6-octabromodiphenyl ether + 2,2',3,3',4,5,5',6'-octabromodiphenyl ether + 2,2',3,3',4,5,5',6-octabromodiphenyl ether + 2,2′,3,3′,4,5′,6,6′-octabromodiphenyl ether

Conditions	Yield
With titanium(IV) oxide In tetrahydrofuran; methanol for 0.166667h; UV-irradiation; Inert atmosphere; Darkness;

...Expand

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → 2,2′,3,4,4′,5,6,6′-octabromodiphenylether + 2,2',3,3',4,4',6,6'-octabromodiphenyl ether + 2,2',3,3',4,4',5,6'-octabromodiphenyl ether + 2,2',3,3',4,4',5,5'-octabromodiphenyl ether + 2,2′,3,3′,4,5′,6,6′-octabromodiphenyl ether

Conditions	Yield
With titanium(IV) oxide In tetrahydrofuran; methanol for 1h; UV-irradiation; Inert atmosphere; Darkness;

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → 2,4-dibromophenol (615-58-7)

Conditions	Yield
With 2 wt.% Pd/TiO2 In tetrahydrofuran; methanol for 0.666667h; Catalytic behavior; Kinetics; Reagent/catalyst; UV-irradiation; Inert atmosphere; Darkness;

2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether (1163-19-5) → Pentabromophenol (608-71-9)

Conditions	Yield
With 2 wt.% Pd/TiO2 In tetrahydrofuran; methanol for 0.166667h; Catalytic behavior; Kinetics; Reagent/catalyst; UV-irradiation; Inert atmosphere; Darkness;

Upstream product

• 101-84-8 diphenylether 
• 7726-95-6 bromine 
• 7727-15-3 aluminium bromide 

Downstream Products

• 63387-28-0 nonabromodiphenyl ether 
• 437701-79-6 BDE-207 
• 68631-49-2 2,2',4,4',5,5'-hexabromobiphenyl ether 
• 207122-16-5 2,3,4,6-tetrabromophenyl 2,4,5-tribromophenyl ether 
• 608-71-9 Pentabromophenol 
• 615-58-7 2,4-dibromophenol 
• 446255-54-5 2,2′,3,4,4′,5,6,6′-octabromodiphenylether 
• 85446-17-9 2,2',3,3',4,4',5,5'-octabromodiphenyl ether 
• 446255-38-5 2,2',3,3',4,4',5,6-octabromodiphenyl ether 
• 446255-56-7 2,3,3',4,4',5,5',6-octabromodiphenyl ether 
• 67797-09-5 2,2',3,3',5,5',6,6'-octabromodiphenyl ether 
• 337513-72-1 2,2',3,4,4',5,5',6-octabromodiphenyl ether 
• 79-28-7 1,1,2,2-tetrabromoethene 
• 53978-00-0 hexabromo-1,3-butadiene 

Relevant articles and documents

PREPARATION OF DECAHALODIPHENYL OXIDE

This invention provides a process of preparing reaction-derived decahalodiphenyl oxide of high purity. The process comprises cofeeding separate feeds of (a) diphenyl oxide and/or partially brominated diphenyl oxide and (b) bromine chloride, bromine chloride and bromine, or bromine chloride and chlorine to a refluxing reaction mixture comprising bromine and at least one Lewis acid bromination catalyst so that high purity decahalodiphenyl oxide is formed.

PREPARATION OF HIGH ASSAY DECABROMODIPHENYL OXIDE

A process is described for producing a reaction-derived decabromodiphenyl oxide product of high purity. In a continuous bromination process, partially brominated diphenyl oxide and coproduct hydrogen bromide are formed by bringing together elemental bromine and diphenyl oxide continuously in a first reaction zone. The partially brominated diphenyl oxide formed has an average of about 2-6 bromine atoms per molecule. The vapor phase and the partially brominated diphenyl oxide are removed continuously from the first reaction zone as separate entities. Then, or after storage, partially brominated diphenyl oxide is fed to a second reaction zone. This zone contains a refluxing reaction mixture comprising (i) an excess of bromine and (ii) a catalytic quantity of Lewis acid bromination catalyst. As the reaction in this zone is taking place, hydrogen bromide coproduct is removed therefrom in a sufficient amount to form a reaction-derived decabromodiphenyl oxide product of high purity.

PREPARATION OF HIGH ASSAY DECABROMODIPHENYL OXIDE

This invention provides a process of preparing reaction-derived decabromodiphenyl oxide product of high purity. The process comprises feeding a solution comprising a solvent and diphenyl oxide and/or partially brominated diphenyl oxide into a reaction zone containing a refluxing reaction mixture comprising an excess of bromine and a catalytic amount of Lewis acid bromination catalyst. Substantially concurrently with the feeding, a sufficient amount of hydrogen bromide coproduct is removed from the reaction zone so as to form a reaction-derived decabromodiphenyl oxide product of high purity.