WO2003055832A1 - Method and apparatus for producing decabromodiphenyl alkanes - Google Patents
Method and apparatus for producing decabromodiphenyl alkanes Download PDFInfo
- Publication number
- WO2003055832A1 WO2003055832A1 PCT/US2002/040568 US0240568W WO03055832A1 WO 2003055832 A1 WO2003055832 A1 WO 2003055832A1 US 0240568 W US0240568 W US 0240568W WO 03055832 A1 WO03055832 A1 WO 03055832A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- tube
- reaction vessel
- bromine
- diphenyl alkane
- alkane
- Prior art date
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/26—Nozzle-type reactors, i.e. the distribution of the initial reactants within the reactor is effected by their introduction or injection through nozzles
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/008—Details of the reactor or of the particulate material; Processes to increase or to retard the rate of reaction
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/0278—Feeding reactive fluids
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/16—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with particles being subjected to vibrations or pulsations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00265—Part of all of the reactants being heated or cooled outside the reactor while recycling
- B01J2208/00292—Part of all of the reactants being heated or cooled outside the reactor while recycling involving reactant solids
- B01J2208/003—Part of all of the reactants being heated or cooled outside the reactor while recycling involving reactant solids involving reactant slurries
Definitions
- This invention relates to methods and an apparatus for producing decabromodiphenyl alkanes. More specifically, the field of the invention is that of producing decabromodiphenyl ethane.
- Halogenated aromatic compounds are often employed as flame retardant agents.
- Flame retardants are substances applied to or incorporated into a combustible material to reduce or eliminate its tendency to ignite when exposed to a low-energy flame, e.g., a match or a cigarette.
- a low-energy flame e.g., a match or a cigarette.
- the incorporation of flame retardants into the manufacture of electronic equipment, upholstered furniture, construction materials, textiles and numerous other products is well known.
- Brominated aromatic compounds are often utilized as flame retardant agents in polymer compositions such as the outer housing of computers, television sets, and other electronic appliances.
- One group of halogenated flame retardants are decabromodiphenyl alkanes.
- the manufacture of decabromodiphenyl alkanes is known.
- decabromodiphenyl alkanes are prepared by reacting a diphenyl alkane with bromine in the presence of a bromination catalyst, such as A1C1 3 or FeCl 3 .
- U.S. Patent No. 5,030,778 to Ransford discloses a process for producing decabromodiphenyl alkanes in which bromine and a bromination catalyst are charged to a reaction vessel. Liquid diphenyl alkane is fed by a dip tube into the reaction vessel at a point which is beneath the level of the charged liquid bromine and catalyst.
- One disadvantage to adding the diphenyl alkane to the vessel at a location below the surface of the charged bromine and catalyst is that the dip tubes used for adding the diphenyl alkane to the vessel are prone to plugging. It is believed that the sub-surface addition dip tubes become plugged when a small amount of diphenyl alkane remains at the tip of the tube and reacts in place, thereby forming insoluble, high melting point material. It is believed that this is more likely to occur at the end of the addition or if the diphenyl alkane addition is interrupted. This susceptibility to plugging prevents the manufacturer from being able to stop and start the diphenyl alkane addition, which is sometimes desirable for controlling the evolution HBr gas.
- the agitation of the reaction mass may create a vortex within the tip of the sub-surface addition dip tube. This vortex may pull solids from the reaction mass into the tube, thereby creating a blockage.
- some diphenyl alkanes such diphenylethane (“DPE")
- DPE diphenylethane
- the agitation of the reaction mass may create a vortex within the tip of the sub-surface addition dip tube. This vortex may pull solids from the reaction mass into the tube, thereby creating a blockage.
- DPE diphenylethane
- DPE diphenylethane
- the diphenyl alkane feed must be stopped and the tube must be pulled out of the reactor in order to remove the blockage. It is desirable to avoid the need to remove the dip tube, as the vapor space of the reaction vessel is filled with toxic and corrosive bromine vapors which may escape during removal.
- the above-surface diphenyl alkane addition technique of the present invention reduces dip tube plugging, thereby providing a more efficient method of adding diphenyl alkane to a reactor charged with bromine and catalyst.
- the present invention is directed to a method and apparatus for producing decabromodiphenyl alkanes, particularly decabromodiphenylethane.
- a diphenyl alkane such as diphenylethane
- the DPE may be fed to the reaction vessel under pressure and at a relatively high velocity from a point above the level of the bromine and catalyst in the reaction vessel.
- Another method for preparing decabromodiphenyl alkanes includes the steps of charging a reaction vessel with bromine and a bromination catalyst, providing a dip tube apparatus having a first end and a second end located in the reaction vessel above the surface level of the bromine and the bromination catalyst, introducing diphenyl alkane through the dip tube apparatus such that the diphenyl alkane flows from the first end, to the second end and enters the reaction vessel at a point above the surface level of the bromine and bromination catalyst in the reaction vessel, reacting the diphenyl alkane with the bromine and the bromination catalyst thereby forming a reaction mass, and recirculating the reaction mass through the dip tube apparatus so as to form a curtain of recirculated reaction mass around the diphenyl alkane being introduced into the reaction vessel.
- the crude decabromodiphenyl alkane, such as decabromodiphenylethane, obtained by the aforementioned process is isolated and purified. Any one of numerous known isolation and purification methods may be utilized.
- the solid may be isolated through direct removal from the slurry by filtration or centrifugation.
- the solid decabromodiphenyl alkane could as be removed by combining the reaction mass with water and striping the bromine through the use of heat and/or a vacuum.
- the crude decabromodiphenyl alkane is first made into a water slurry, and is transferred to a another reactor.
- the slurry is washed with an alkaline solution and the solid decabromodiphenyl alkane is separated and washed with water.
- the solid decabromodiphenyl alkane is then in the form of a filter cake.
- the filter cake may be treated in any one of a number of known ways.
- the cake may first be dried and then fractured and/or heat treated in a number of ways.
- the wet decabromodiphenyl alkane product may also be treated without first drying, as disclosed in U.S. Patent No. 4,659,021 to Bark, et al.
- the filter cake is dried and then ground twice in an air mill using air which is heated to an inlet temperature of approximately 260° C.
- the ground decabromodiphenyl alkane is then heat-treated at approximately 240° C for three to four hours in order to release any free bromine which may be present in the product.
- the release of free bromine improves the purity and the color of the end product.
- Other known isolation and purification methods may also be utilized, such as those disclosed in U.S. Patent No. 4,327,227 to Ayres, et al. and U.S. Patent No. 5,030,778 to Ransford.
- An apparatus for preparing decabromodiphenyl alkanes includes a dip tube apparatus disposed above the surface level of the charged liquid bromine in the reaction vessel and includes an inner tube and an outer tube.
- the inner tube has a first end and a second end. The first end is adapted to receive a flow of diphenyl alkane.
- the second end of the inner tube is adapted to receive a plug.
- the plug includes a hollow portion and an opening. When the inner tube and the plug are engaged, the plug and the inner tube are in fluid communication with one another. The diphenyl alkane flows through the inner tube, through an opening in the plug, and into the reaction vessel at a location which is above the surface level of the charged liquid bromine and the bromination catalyst.
- Plugs having a variety of opening sizes and configurations may be chosen in order to achieve the desired flow rate diphenyl alkane.
- the plug can be eliminated and the opening through which the diphenyl alkane flows can be formed in one end of the inner tube.
- the outer tube of the dip tube apparatus extends around the inner tube.
- the reaction mass within the reaction vessel is pumped out of the reaction vessel, through the outer tube, and then back into the reaction vessel.
- the outer tube is spaced from the inner tube, such that the recirculated reaction mass re-enters the reaction vessel in the form of a curtain surrounding the diphenyl alkane stream.
- the curtain of recirculated reaction mass does not come into contact with the stream of diphenyl alkane being simultaneously added to the reaction vessel through the inner tube.
- Figure 1 is a sectional view illustrating the dip tube apparatus according to one embodiment of the present invention disposed in a reaction vessel;
- Figure 2 is a perspective views of a plug that is a component of the dip tube apparatus of Figure 1;
- Figure 3 is an end view of the dip tube apparatus taken along line 3-3 of Figure 1.
- dip tube apparatus 10 is disposed in reaction vessel 11.
- Reaction vessel 11 may be any size desired, but for commercial applications, a reactor of at least 3,000 gallons is typically preferred.
- Dip tube apparatus 10 includes inner tube 12 and outer tube 14.
- Inner tube 12 may be manufactured out of Teflon or any other suitable material having similar properties, and outer tube 14 may be manufactured of Kynar or any other suitable material having similar properties.
- Inner tube 12 includes first end 13 ⁇ and second end 13b.
- First end 13a is adapted for receiving a flow of a diphenyl alkane, such as, for example, DPE, as indicated by arrow A.
- Second end 13b is adapted for receiving plug 18, as described below.
- Outer tube 14 extends along and surrounds inner tube 12 as shown. Outer tube 14 includes first end 15a and second end 15b.
- Figure 3 illustrates an end view of dip tube apparatus 10 taken along line 3-3 of Figure 1. As shown in Figure 3, spacers 25 serve to separate inner tube 12 from outer tube 14. Spacers 25 are may be manufactured from a 15% glass Teflon material or any other suitable material.
- plug 18, in the embodiment shown, includes a hollow portion 20 and a generally disc-shaped portion 24.
- Disc-shaped portion 24 includes a first surface 26 ⁇ having an opening 26b therein. Note that in the embodiment shown, the side of disc-shaped portion 24 is flared.
- Hollow portion 20 and opening 26b are in fluid communication such that DPE flowing through hollow portion 20 will exit plug 18 through opening 26b.
- the size and shape of opening 26b may be varied depending upon the desired flow rate of DPE into reaction vessel 11. Typically, opening 26b will have a diameter of between about 0.0625" and about 0.0937".
- second end 13b of inner tube 12 includes a threaded portion 16 which is adapted to receive corresponding threads 16 of plug 18 such that plug 18 is secured within second end 13b of inner tube 12.
- This arrangement allows the size and shape of opening 26b to be changed by changing plug 18.
- Other mechanisms for securing plug 18 to inner tube 12 may also be utilized.
- plug 18 When plug 18 is secured within second end 13b of inner tube 12, inner tube 12 and plug 18 are in fluid communication such DPE flowing through inner tube 12 will flow into hollow portion 20 and out opening 26b.
- Plug 18 may be manufactured from Teflon or any other suitable material.
- plug 18 can be completely eliminated by constructing second end 13b of inner tube 12 with an appropriately sized and shaped opening for introducing DPE into reaction vessel 11. Of course, this would mean that the entire inner tube 12 would have to be changed to change the size and shape of the opening.
- dip tube apparatus 10 is disposed in reaction vessel 11 such that second end 15b of outer tube 14 is located at the same level as second end 13 of inner tube 12. Both second end 15b of outer tube 14 and second end 13b of inner tube 12 are located a distance D above surface 26 ⁇ of plug 18. In the embodiment shown, distance D corresponds to the thickness of portion 24 of plug 18. In one embodiment of the invention, distance D is about 0.5 inches. Note also that it is not necessary that surface 26a of plug 18 be located below second end 15b of outer tube 14. That is, inner tube 12 and plug 18 may be positioned such that surface 26a is recessed within outer tube 14 and is located further from level L than is second end 15b of outer tube 14.
- surface 26 ⁇ of plug 18 is located a distance X above surface level L of the charged bromine and catalyst.
- distance X is about 4 inches.
- distance X will be between about 1 inch and about 12 inches. If an inner tube 12 is utilized without a plug 18, as described above, inner tube 12 and outer tube 14 would be positioned such that second end 13b of inner tube 12 is located a distance D below second end 15b of outer tube 14. Similarly, inner tube 12 would be positioned such that second end 13b is located a distance X above level L.
- DPE is fed, under pressure, through inner tube 12 and emitted as a stream 36 via opening 26a into reaction vessel 11.
- the DPE preferably has a purity level of about 99.7% or greater, however, DPE of different purity levels can be used depending on the desired characteristics of the final product.
- the pressure at which the DPE is fed is preferably at least about 20 psig and preferably between about 20 psig and about 60 psig.
- the DPE stream 36 preferably has a velocity within the range of about 9 meters per second to about 25 meters per second. In one embodiment of the invention, the DPE is fed at about 17.5 meters per second under a pressure of about 30 psig.
- An agitator (not shown) operating at approximately 47-88 rpm and disposed within reaction vessel 11 mixes the DPE and the bromine reaction medium, thereby facilitating the reaction.
- reaction mass 38 is recirculated to first end 15a of outer tube 14 and allowed to flow through outer tube 14 (shown in Figure 1 by arrows B), along inner tube 12 and back into reaction vessel 11.
- reaction mass 38 is recirculated at a rate of between about 45 gallons per minute to 250 gallons per minute.
- a curtain 34 of reaction mass 38 is formed around DPE stream 36.
- the distance Y between curtain 34 and DPE stream 26 is preferably at least about 0.5 inches. In one embodiment of the invention, distance Y is about 0.867". Note that DPE stream 26 does not come into contact with curtain 34.
- the flared sides of portion 24 of plug 18 assists in keeping the DPE stream 26 and the curtain 34 separated.
- Decabromodiphenylethane may be obtained according to the present invention by reacting DPE in the presence of an excess of bromine and a bromination catalyst.
- the molar ratio of bromine to DPE is between about 18:1 and about 50:1. Preferably, the ratio is between about 18:1 to about 39:1.
- Appropriate bromination catalysts include aluminum halides, such as aluminum chloride and aluminum bromide, as well as iron powder. Other catalysts may also be used.
- the temperature of the reaction mass is preferably in the range of about 50° C to about 60° C.
- the temperature of the reaction mass is maintained at 55° C until the DPE feed is complete.
- the temperature is then increased to approximately 60° C and held constant for the duration of the reaction time.
- the reaction time will vary depending upon the amount of DPE being added, and upon the rate at which the DPE is added. For commercial production, reaction times will likely be between three and six hours.
- the decabromodiphenylethane slurry is placed in a pressurized vessel charged with water which has been heated to approximately 70° C. Once the slurry addition is complete, the temperature within the vessel is increased to approximately 100° C to facilitate the removal of any remaining free bromine. The water slurry is transferred to a tank which is charged with a solution which is 25% alkaline. The resulting slurry is then fed to a centrifuge where the solid decabromodiphenylethane product is separated and washed with water. The solid is in the form of a filter cake.
- the filter cake of decabromodiphenylethane is then dried and ground twice in an air mill using air heated to an inlet temperature of approximately 260° C.
- the resulting material is heat-treated at approximately 240° C for 3-4 hours.
- the final product preferably has a yellowness index of below about 10, and more preferably below about 9.
- EXAMPLE A 3000 gallon glass lined Pfaudler reactor was equipped with a vertical H-type baffle, condenser system, 41" Pfaudler Cryo-lock reverse curve agitator, temperature sensor, and the dip tube apparatus described above. 21,210 kg (132,278.41 moles) of liquid bromine and 63.5 kg (476.26 moles) of aluminum chloride were charged to the reaction vessel. The agitator was then turned on and ranged in speed from 47 to 88 rpm. The reactor was heated to 55° C. 618 kg (3395.6 moles) of DPE was then charged through the dip tube, as described above, at a rate of 4-8.5 lbs./min. The DPE addition ranged from 3.5 to 5 hours. Once the feed was completed, the reaction temperature was increase to 60° C and held at that temperature for thirty minutes.
- a 4000 gallon glass lined Pfaudler reactor was equipped with a vertical H-type baffle, condenser system, 41" Pfaudler Cryo-lock reverse curve agitator, and temperature sensor.
- the vessel was charged with 1850 gallons of water. The water was then heated to 70° C.
- the bromine slurry from the reactor was fed into the vessel over a 2.5 to 3 hour period, while maintaining 5 to 5.5 lbs. of pressure within the vessel. Once the slurry addition was complete, the temperature within the vessel was raised to 100° C to complete the bromine removal.
- the water slurry was transferred to a 5000 gallon tank equipped with an agitator.
- the tank was charged with 475 gallons of a 25% caustic (alkaline) solution.
- the resulting slurry was then fed to a centrifuge where the solid was separated and washed with water.
- the filter cake was then dried.
- the resulting material was then ground twice by passing it through a Fluid Energy Aljet air mill using air heated to 260° C.
- the product was then heat treated in a Wyssmont drier at 240° C for 3 to 4 hours.
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE60235833T DE60235833D1 (en) | 2001-12-21 | 2002-12-18 | METHOD AND DEVICE FOR PREPARING DECABROM DIPHENYL ALKANES |
IL16092902A IL160929A0 (en) | 2001-12-21 | 2002-12-18 | Method and apparatus for producing decabromodiphenyl alkanes |
EP02797416A EP1456156B1 (en) | 2001-12-21 | 2002-12-18 | Method and apparatus for producing decabromodiphenyl alkanes |
AT02797416T ATE462681T1 (en) | 2001-12-21 | 2002-12-18 | METHOD AND DEVICE FOR PRODUCING DECABROMODIPHENYLALKANES |
AU2002361780A AU2002361780A1 (en) | 2001-12-21 | 2002-12-18 | Method and apparatus for producing decabromodiphenyl alkanes |
IL160929A IL160929A (en) | 2001-12-21 | 2004-03-18 | Method and apparatus for producing decabromodiphenyl alkanes |
IL196048A IL196048A (en) | 2001-12-21 | 2008-12-18 | Apparatus for producing decabromodiphenyl alkanes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US34506301P | 2001-12-21 | 2001-12-21 | |
US60/345,063 | 2001-12-21 |
Publications (1)
Publication Number | Publication Date |
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WO2003055832A1 true WO2003055832A1 (en) | 2003-07-10 |
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ID=23353325
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US2002/040568 WO2003055832A1 (en) | 2001-12-21 | 2002-12-18 | Method and apparatus for producing decabromodiphenyl alkanes |
Country Status (8)
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US (2) | US6841707B2 (en) |
EP (1) | EP1456156B1 (en) |
CN (1) | CN100448821C (en) |
AT (1) | ATE462681T1 (en) |
AU (1) | AU2002361780A1 (en) |
DE (1) | DE60235833D1 (en) |
IL (3) | IL160929A0 (en) |
WO (1) | WO2003055832A1 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2008057645A1 (en) * | 2006-11-08 | 2008-05-15 | Albemarle Corporation | Preparation of high assay decabromodiphenylalkane |
WO2008066980A1 (en) * | 2006-12-01 | 2008-06-05 | Albemarle Corporation | Production of high purity decabromodiphenylalkanes |
US7408088B1 (en) | 2007-02-08 | 2008-08-05 | Albemarle Corporation | Process for separation of bromine from gaseous hydrogen bromide and use of such process in production of decabromodiphenylethane |
US7851662B2 (en) | 2007-03-16 | 2010-12-14 | Albemarle Corporation | Preparation and provision of high assay decabromodiphenylethane |
US7994373B2 (en) | 2007-03-16 | 2011-08-09 | Albemarie Corporation | Preparation and provision of high assay decabromodiphenylethane |
US8034986B2 (en) | 2006-11-09 | 2011-10-11 | Albemarle Corporation | Processing of solid brominated aromatic organic compounds containing occluded bromine |
US8680347B2 (en) | 2009-07-27 | 2014-03-25 | Albemarle Corporation | Preparation of high assay decabromodiphenylalkane product with low occluded free bromine content |
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CA2661809A1 (en) * | 2006-08-29 | 2008-03-06 | Albemarle Corporation | Preparation of decahalodiphenyl ethane |
WO2008026215A2 (en) * | 2006-08-31 | 2008-03-06 | Bromine Compounds Ltd. | A process for preparing polybrominated compounds |
KR101221815B1 (en) * | 2009-12-24 | 2013-01-14 | 제일모직주식회사 | Method for Preparing Mixtures of Brominated Diphenyl Ethanes |
CN110142010B (en) * | 2019-05-27 | 2021-09-17 | 河北鸿新源化工有限公司 | Method and apparatus for producing polychlorinated aromatic compounds by chlorination of aromatic compounds |
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-
2002
- 2002-12-18 EP EP02797416A patent/EP1456156B1/en not_active Expired - Lifetime
- 2002-12-18 AT AT02797416T patent/ATE462681T1/en not_active IP Right Cessation
- 2002-12-18 WO PCT/US2002/040568 patent/WO2003055832A1/en active Application Filing
- 2002-12-18 CN CNB028245075A patent/CN100448821C/en not_active Expired - Fee Related
- 2002-12-18 AU AU2002361780A patent/AU2002361780A1/en not_active Abandoned
- 2002-12-18 US US10/323,012 patent/US6841707B2/en not_active Expired - Lifetime
- 2002-12-18 DE DE60235833T patent/DE60235833D1/en not_active Expired - Lifetime
- 2002-12-18 IL IL16092902A patent/IL160929A0/en unknown
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2004
- 2004-03-18 IL IL160929A patent/IL160929A/en active IP Right Grant
- 2004-12-30 US US11/026,624 patent/US7776289B2/en active Active
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2008057645A1 (en) * | 2006-11-08 | 2008-05-15 | Albemarle Corporation | Preparation of high assay decabromodiphenylalkane |
US8034986B2 (en) | 2006-11-09 | 2011-10-11 | Albemarle Corporation | Processing of solid brominated aromatic organic compounds containing occluded bromine |
WO2008066980A1 (en) * | 2006-12-01 | 2008-06-05 | Albemarle Corporation | Production of high purity decabromodiphenylalkanes |
US7408088B1 (en) | 2007-02-08 | 2008-08-05 | Albemarle Corporation | Process for separation of bromine from gaseous hydrogen bromide and use of such process in production of decabromodiphenylethane |
US7851662B2 (en) | 2007-03-16 | 2010-12-14 | Albemarle Corporation | Preparation and provision of high assay decabromodiphenylethane |
US7994373B2 (en) | 2007-03-16 | 2011-08-09 | Albemarie Corporation | Preparation and provision of high assay decabromodiphenylethane |
US8217207B2 (en) | 2007-03-16 | 2012-07-10 | Albemarle Corporation | Preparation and provision of high assay decabromodiphenylethane |
US8680347B2 (en) | 2009-07-27 | 2014-03-25 | Albemarle Corporation | Preparation of high assay decabromodiphenylalkane product with low occluded free bromine content |
Also Published As
Publication number | Publication date |
---|---|
CN100448821C (en) | 2009-01-07 |
IL160929A (en) | 2010-05-17 |
AU2002361780A1 (en) | 2003-07-15 |
CN1602287A (en) | 2005-03-30 |
ATE462681T1 (en) | 2010-04-15 |
US20030144563A1 (en) | 2003-07-31 |
IL196048A (en) | 2011-06-30 |
US6841707B2 (en) | 2005-01-11 |
IL196048A0 (en) | 2009-02-11 |
DE60235833D1 (en) | 2010-05-12 |
IL160929A0 (en) | 2004-08-31 |
EP1456156B1 (en) | 2010-03-31 |
EP1456156A1 (en) | 2004-09-15 |
US20050118080A1 (en) | 2005-06-02 |
US7776289B2 (en) | 2010-08-17 |
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