Abstract: The present invention provides a method of converting a brominated hydrocarbon to a chlorinated hydrocarbon that involves contacting together the brominated hydrocarbon and a chlorinated ion exchange resin that has a water content of less than or equal to 30 percent by weight, based on the total weight of the chlorinated ion exchange resin and the water. The brominated hydrocarbon includes at least one replaceable bromo group, where each replaceable bromo group is independently covalently bonded to an sp3 hybridized carbon. Contact between the brominated hydrocarbon and the chlorinated ion exchange resin results in replacement of at least one replaceable bromo group of the brominated hydrocarbon with a chloro group, and correspondingly conversion of at least a portion of the brominated hydrocarbon to the chlorinated hydrocarbon.

Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride, ethylene, and chlorine.

Abstract: A method and apparatus for method of continuously producing 1,1,1,2,3-pentafluoropropane with high yield is provided. The method includes (a) bringing a CoF3-containing cobalt fluoride in a reactor into contact with 3,3,3-trifluoropropene to produce a CoF2-containing cobalt fluoride and 1,1,1,2,3-pentafluoropropane, (b) transferring the CoF2-containing cobalt fluoride in the reactor to a regenerator and bringing the transferred CoF2-containing cobalt fluoride into contact with fluorine gas to regenerate a CoF3-containing cobalt fluoride, and (c) transferring the CoF3-containing cobalt fluoride in the regenerator to the reactor and employing the transferred CoF3-containing cobalt fluoride in Operation (a). Accordingly, the 1,1,1,2,3-pentafluoropropane can be continuously produced with high yield from the 3,3,3-trifluoropropene using a cobalt fluoride (CoF2/CoF3) as a fluid catalyst, thereby improving the reaction stability and readily adjusting the optimum conversion rate and selectivity.

Abstract: Processes for the production of chlorinated propanes and propenes are provided. The present processes comprise catalyzing at least one chlorination step with one or more regios elective catalysts that provide a regioselectivity to one chloropropane of at least 5:1 relative to other chloropropanes.

Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride, ethylene, and chlorine.

Abstract: A method of producing a chlorinated hydrocarbon having 3 carbon atoms, comprising a conversion step for converting a chloropropane represented by the following formula (1) into a chloropropane represented by the following formula (2) by reacting it with chlorine in the presence of anhydrous aluminum chloride. CCl3—CCl(2-m)Hm—CCl(3-n)Hn??(1) (In the above formula (1), m is 1 or 2, and n is an integer of 0 to 3.) CCl3—CCl(3-m)H(m-1)—CCl(3-n)Hn??(2) (In the above formula (2), m and n are the same integers as in the formula (1), respectively.

Abstract: A process and system for recovering hydrogen bromide, methane, ethane and propane from butane and higher hydrocarbon products by means of condensation, cryogenic liquefaction and distillation, and for oxidation of the hydrogen bromide to bromine for re-use within a gas-conversion process for producing higher-molecular weight hydrocarbons.

Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride, ethylene, and chlorine.

Abstract: This invention relates to novel and useful toluene and styrene derived telomer distributions, such distributions being desirable substrates for the preparation of brominated flame retardants.

Abstract: A method of producing a chlorinated hydrocarbon having 3 carbon atoms, comprising a conversion step for converting a chloropropane represented by the following formula (1) into a chloropropane represented by the following formula (2) by reacting it with chlorine in the presence of anhydrous aluminum chloride. CCl3—CCl(2-m)Hm—CCl(3-n)Hn??(1) (In the above formula (1), m is 1 or 2, and n is an integer of 0 to 3.) CCl3—CCl(3-m)H(m-1)—CCl(3-n)Hn??(2) (In the above formula (2), m and n are the same integers as in the formula (1), respectively.

Abstract: Improvements in previously disclosed methods of and apparatuses for converting alkanes, alkenes, and aromatics to olefins, alcohols, ethers, and aldehydes includes: safety improvements, use of alternative feedstocks, process simplification, improvements to the halogenation step, improvements to the reproportionation step, improvements to the solid oxide reaction, improvements to solid oxide regeneration, improvements in separations, maintenance, start-up, shut-down, and materials of construction.

Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride, ethylene, and chlorine.

Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride, ethylene, and chlorine.

Abstract: High assay, reaction-derived decabromodiphenylethane product is prepared by feeding (i) diphenylethane or (ii) partially brominated diphenylethane having an average bromine number less than about two, or (iii) both of (i) and (ii), into the liquid confines of a reaction mixture. Such reaction mixture is (a) formed from components comprised of excess liquid bromine and aluminum-based Lewis acid bromination catalyst, and (b) maintained at one or more elevated reaction temperatures of from about 45°-90° C., and at least when elevated pressure is needed to keep a liquid state in the reaction mixture at the temperature(s) used, the reaction mixture is at such an elevated pressure, whereby ar-bromination occurs. The feeding is conducted at a rate slow enough to form high assay reaction-derived decabromodiphenylethane product, which is an effective flame retardant.

Abstract: A process for selectively producing 4,9-dibromodiamantane includes a step of reacting diamantane with bromine in the presence of a Lewis acid and a solvent, wherein the solvent comprises a substituted or unsubstituted, straight-chain, branched-chain or cyclic saturated hydrocarbon containing from 3 to 10 carbon atoms, and a reaction solution after the step satisfies Formula (1): A/(A+B+C+D+E)>0.80 ??Formula (1) wherein A represents an area ratio (%) of 4,9-dibromodiamantane obtained by gas chromatography of the reaction solution, B represents an area ratio of diamantane, C represents a sum of an area ratio of 1-bromodiamantane and an area ratio of 4-bromodiamantane, D represents an area ratio of tribromodiamantane, and E represents a sum of an area ratio of 1,6-dibromodiamantane and an area ratio of 1,4-dibromodiamantane.

Abstract: Polybrominated bisaryl compounds containing bromomethyl or bromomethylene groups are provided, as well as flameproof polymeric formulations comprising the compounds. The novel compounds exhibit a good thermal stability, and are particularly suitable for flame-retarding polystyrene thermoplastic foams. A process for making the polybrominated bisaryl compounds is also provided.

Abstract: The present invention discloses a process for the preparation of highly pure pentabromobenzyl bromide, PBB-Br, wherein the benzylic bromination reaction is carried out in a suitable organic solvent in the presence of water and wherein the reaction temperature is such that it is sufficient to activate the initiator but not high enough to consume a substantial amount thereof.

Abstract: A process for converting gaseous alkanes to olefins, higher molecular weight hydrocarbons or mixtures thereof wherein a gaseous feed containing alkanes is thermally reacted with a dry bromine vapor to form alkyl bromides and hydrogen bromide. Poly-brominated alkanes present in the alkyl bromides are further reacted with methane over a suitable catalyst to form mono-brominated species. The mixture of alkyl bromides and hydrogen bromide is then reacted over a suitable catalyst at a temperature sufficient to form olefins, higher molecular weight hydrocarbons or mixtures thereof and hydrogen bromide. Various methods are disclosed to remove the hydrogen bromide from the higher molecular weight hydrocarbons, to generate bromine from the hydrogen bromide for use in the process, and to selectively form mono-brominated alkanes in the bromination step.

Abstract: A process for converting gaseous alkanes to olefins, higher molecular weight hydrocarbons or mixtures thereof wherein a gaseous feed containing alkanes is reacted with a dry bromine vapor to form alkyl bromides and hydrobromic acid vapor. The mixture of alkyl bromides and hydrobromic acid is then reacted over a suitable catalyst at a temperature sufficient to form olefins, higher molecular weight hydrocarbons or mixtures thereof and hydrobromic acid vapor. Various methods are disclosed to remove the hydrobromic acid vapor from the higher molecular weight hydrocarbons, to generate bromine from the hydrobromic acid for use in the process, and to selectively form monobrominated alkanes in the bromination step.

Abstract: A catalytic one-step process for the production of CF3I by reacting, preferably in the presence of a source of oxygen, a source of iodine with a reactant of the formula: CF3R where R is —SH, —S—S—CF3, —S-phenyl, or —S—Si—(CH3)3. The catalyst may be a metal salt such as salts of Cu, Hg, Pt, Pd, Co, Mn, Rh, Ni, V, TI, Ba, Cs, Ca, K and Ge and mixtures thereof, preferably on a support such as MgO, BaO and CaO, BaCO3, CsNO3, Ba (NO3)2, activated carbon, basic alumina, and ZrO2.

Abstract: With a method or a device for producing 1,2-dichloroethane or ethylene (di)chloride (EDC) with the use of a circulating reaction medium and a catalyst, whereby ethylene and chlorine are supplied to the reaction medium, the goal is to permit the catalytic chlorination of ethylene in a manner that is particularly gentle to the product. This is achieved in terms of the method and by other means in that the ethylene or chlorine gas are introduced into the reaction medium by means of microporous gas diffuser elements for producing gas bubbles with a diameter of 0.3 to 3 mm.

Abstract: Aromatic compounds such as toluene and o-xylene are chlorinated in the presence of a catalyst combination prepared by combining (A) at least one salt comprising a metal selected from the group consisting of a Group 4-12 metal, a lanthanide and an actinide; and a counterion; and (B) at least one organic sulfur compound, preferably phenothiazine-N-carbonyl chloride. The catalyst combination may include reaction products of (A) and (B). Under these conditions, production of the p-chloro isomer is optimized. In some embodiments said counterion is an organic counterion derived from at least one acidic organic compound selected from the group consisting of those with an approximate pKa value relative to water of at least about 3.

Abstract: An oxidative halogenation process involving contacting a reactant hydrocarbon selected from methane, a halogenated C1 hydrocarbon, or a mixture thereof with a source of halogen and, preferably, a source of oxygen in the presence of a rare earth halide or rare earth oxyhalide catalyst, so as to form a halogenated C1 hydrocarbon having a greater number of halogen substituents as compared with the reactant hydrocarbon. Preferably, the product is a monohalogenated methane, more preferably, methyl chloride. The oxidative halogenation process to form methyl halide can be integrated with downstream processes to produce valuable commodity chemicals, for example, methyl alcohol and/or dimethyl ether; light olefins, including ethylene, propylene, and butenes; higher hydrocarbons, including gasolines; vinyl halide monomer, and acetic acid. Hydrogen halide, which is a co-product of these downstream processes, can be recycled to the oxidative halogenation process.

Abstract: The invention relates to a process for selectively producing alkyl halides from alkanes, such as methane and ethane at low temperatures and low pressures. Optional hydrolysis to the corresponding alcohols may follow. The process involves adding an alkane and an added halogen source to an aqueous solution in a homogeneous system in the presence of a transition metal halide containing complex, for a time, under conditions and in effective amounts that will permit the formation of alkyl monohalides.

Abstract: The use of hitherto known supported catalysts in chlorination processes and oxychlorination processes leads to high pressure drops and to the formation of hot spot temperatures in the reactor. When honeycomb monolithic catalyst supports provided with a multiplicity of channels open at both ends and parallel to the longitudinal axis are used, both the heat dissipation is improved and the pressure drops across the reactor are lowered drastically. This leads ultimately to an increase in the selectivity of the reaction and to a minimization of the combustion rate.

Abstract: The novel compound 5,6,7,8-tetrabromo-1,2,3,4-tetrahydro-naphthalene (tetrabromotetralin) of the formula: ##STR1## was prepared using 1,2,3,4-tetrahydro-naphthalene as the starting compound. Tetrabromotetralin was employed to prepare flame-retardant plastic compositions.

Abstract: A process for the preparation of dibromomethane is described, in which gaseous methyl bromide and bromide are reacted as temperatures of 300.degree. C. or higher. The reaction is highly selective to DBM and almost quantitative Br.sub.2 conversion is obtained in the absence of catalysts.

Abstract: A method of producing 3-bromobenzaldehyde is disclosed, wherein, upon producing 3-bromobenzaldehyde by allowing benzaldehyde to react with bromine in the presence of brominating catalyst in 1,2-dichloroethane being a reaction solvent, 1,2-dichloroethane having been used for aforesaid reaction as a reaction solvent is recovered and, after the recovered solvent is allowed first to react with chlorine in the presence of above brominating catalyst, the reaction is performed by the addition of benzaldehyde and bromine. Foregoing 1,2-dichloroethane recovered may be brought to the reaction with chlorine with or without adding fresh 1,2-dichloroethane and above brominating catalyst is preferably aluminum chloride.

Abstract: A catalyst, such as FeCl.sub.3, useful in the production of chlorinated hydrocarbons such as 1,1-dichloroethane is removed from the effluent of a process reactor and recycled. Hydrochloric acid is removed from the process stream resulting in the catalyst present in the process stream in solution precipitating out of solution. Then it can be removed from the process stream by conventional separation techniques. Alternatively, the catalyst present in the process stream as a solid, without the removal of HCl, is separated from the liquid present by means of a cyclone and recycled. In both cases, the catalyst retains its catalytic activity.

Abstract: A method is disclosed for the preparation of 1,2-dichloroethane in a reactor by the reaction of gaseous ethylene with chlorine dissolved in a hot, catalyst-containing, liquid circulating stream that is under elevated pressure and consists of chlorinated hydrocarbons. All of the chlorine is absorbed outside of the reactor, at a temperature above 90.degree. C., a pressure of more than 4 bar, and an average residence time of less than 120 seconds. The reaction takes place at the phase boundary surface of a dispersion produced from gaseous ethylene and the chlorine-containing, liquid, circulating stream, at an energy dissipation density of 0.05 to 1000 kilowatts per cubic meter, a temperature of 90.degree. to 200.degree. C., and a pressure of 7 to 20 bar. Iron(III) chloride is used preferably as catalyst. Oxygen is used preferably as inhibitor for preventing the formation of byproducts.

Abstract: The disclosure relates to a process for making 1,2-dichloroethane by reacting ethylene with chlorine in a solvent in the presence of a catalyst, at a temperature of about 20.degree. to 200.degree. C. at atmospheric or elevated pressure, and distillatively separating the 1,2-dichloroethane from the chlorination mixture. The disclosure provides more particularly for the catalyst used to be an anhydrous tetrachloroferrate(1-) or a substance capable of forming a tetrachloroferrate(1-) in the reaction mixture.

Abstract: In a process for producing 1,2-dichloroethane or ethylene dichloride ("EDC") in a high temperature direct chlorination ("HTDC") reactor in which ethylene is reacted with wet chlorine having a water content more than 100 ppm but no more than 1% by wt of the chlorine, the water leaves the reactor with the EDC product draw-off, either in the vapor overhead (if the HTDC is a boiling reactor), or, as a liquid sidestream (if the HTDC is a non-boiling reactor). In a subsequent step, the EDC draw-off is distilled in a product distillation column in which the water leaves in the overhead which is condensed to remove condensables in a first stage, and vent a non-condensable vent streams. The vent stream is corrosive due to the presence of minor amounts of chlorine, HCl and water, along with oxygen which is injected into the HTDC to improve selectivity of the reaction. The vent gases from the first stage are further cooled to a temperature in the range from about -30.degree. C. to about 0.degree. C.

Abstract: The disclosure relates to a process for making 1,2-dichloroethane by reacting ethylene and chlorine in a reaction zone having a liquid medium containing chlorinated C.sub.2 -hydrocarbons circulated therein. To this end, the disclosure provides:(a) for approximately equimolar proportions of ethylene and chlorine to be introduced into the circulated liquid medium; for the whole to be reacted in a reaction zone at a temperature of about 75.degree. up to 200.degree. C.

Abstract: Olefins containing at least 7 carbon atoms are used to remove molecular chlorine form compositions comprising 1,2-dichloroethane and a contaminating amount of molecular chlorine.

Abstract: A process is disclosed for the economical operation of a commercial ethylene dichloride (EDC) cracking furnace which typically is prone to coking of the tubes through which the EDC is flowed. The EDC cracking furnace is found to be critically sensitive to the presence of trace amounts, 30 ppm or more of FeCl.sub.3 and/or 20 ppm or more of free chlorine, which cause coking of the tubes of the furnace. The coking of the tubes is minimized by maintaining less than 30 ppm by weight of FeCl.sub.3 or less than 20 ppm of free chlorine in the EDC feed to the EDC furnace. In the particular instance where EDC is produced at least in part in a high temperature direct chlorination ("boiling") reactor constructed from mild steel, this goal requires that the chlorine content of the effluent from the boiling reactor be controlled so as not to exceed 20 ppm. But this is to be done without using more than a 2% by weight excess of ethylene over the stoichiometric amount required to produce the EDC in the boiling reactor.

Abstract: In this method of producing 1,2-dichloroethane from ethylene and chlorine gas in an approximately equimolar ratio at reaction pressures between 2 and 20 bar, at ethylene dichloride boiling temperatures between 105.degree. and 225.degree. C., in the presence of catalysts acting as Lewis acids, the catalyst-free ethylene dichloride vapors produced in the evaporative cooling are withdrawn and then condensed and cooled, and liquid catalyst-containing ethylene dichloride is also withdrawn separately.All of the gaseous chlorine input, having a purity of about 90 to 100% by volume, is introduced into a condensed and cooled circulating stream of ethylene dichloride. The ethylene dichloride stream containing chlorine is brought to the reaction pressure, and then catalyst-containing ethylene dichloride withdrawn from the reactor is admixed.

Abstract: A trace amount of free chlorine, present along with comparable amounts of ethylene, oxygen and water vapor in the ethylene dichloride (EDC) effluent from a direct chlorination reactor, may be effectively scavenged by exposing the effluent to ultraviolet ("u-v") light having a wavelength less than about 4000.ANG. which is absorbed by the chlorine, but to which both ethylene and EDC are essentially transparent. In this process, contaminant chlorine in substantially pure (99..sup.+ %) EDC is catalytically activated and reacts with EDC to form an unwanted byproduct, namely 1,1,2-trichloroethane ("triane"). The process is effective in either the gaseous phase or the liquid phase.

Abstract: A method for preparing hydrogen chloride resulting from chlorination reactions for use in the ethyleneoxichlorination process by reacting the chlorine contained in the hydrogen chloride with ethylene in the gaseous phase in the presence of carrier catalysts based on an iron-free transition metal chloride having an activity profile which increases in the flow direction, while maintaining the space-flow rates relatively high and the residence time of the gas in the reactor short. After discharge of the reaction product from the reactor the product is subjected to partial condensation advantageously performed in several steps.

Abstract: This invention relates to solid acidic or metal catalyst-promoted halogenation of methane to produce methyl monohalides in high selectivity. Concurrent or simultaneous hydrolysis provides methyl alcohol and/or dimethyl ether in good yields.

Abstract: A process for consecutive-competitive gas phase halogenation of organic compounds, i.e. alkanes, alkenes and benzene, alkyl benzenes and alkenyl benzenes containing labile hydrogens and having no more than 12 and 9 carbon atoms, respectively, in a thin reaction film on the surface of a porous barrier for production of highly halogenated products by substantial suppression of diffusion of partially halogenated intermediates away from the reaction film is disclosed.

Abstract: The invention relates to the production of anhydrous alkyl iodides. To this end, carboxylic acid alkyl esters of the formula R.sup.1 COOR.sup.2, in which R.sup.1 stands for hydrogen or an alkyl or aryl radical having from 1 to 8 carbon atoms and R.sup.2 stands for an alkyl group having from 1 to 4 carbon atoms, are reacted with iodine and hydrogen and optionally with carbon monoxide in the presence of compounds of noble metals comprised of rhodium, iridium, palladium or ruthenium as catalyst, and of a heterocyclic aromatic compound, in which at least one hetero atom is a quaternary nitrogen atom, or of a quaternary organophosphorus compound as a promoter, and optionally also in the presence of a carboxylic acid having from 1 to 8 carbon atoms and/or its anhydrides. The reaction is effected under practically anhydrous conditions at temperatures of from 350 to 420 K. and under a total pressure of up to 30 bars.

Abstract: Method of producing ethylene dichloride characterized by reaction of ethylene and chlorine in a reaction zone containing a circulating medium and maintained below the vaporization point of the medium, and utilization of the heat from the reaction to vaporize and rectify a portion of the circulating medium in another zone to recover the product.

Abstract: A process for removing ethylene and vinyl chloride from a gas stream containing them by passing a mixed gas containing ethylene, vinyl chloride and a necessary amount of chlorine through a fixed-bed reactor charged with as a catalyst an activated alumina supporting at least 4% by weight of ferric chloride in terms of iron, said catalyst having an outer surface area per unit packed catalyst volume of not less than 7.8 cm..sup.2 /ml. Ethylene and vinyl chloride are converted into and removed as 1,2-dichloroethane and 1,1,2-trichloroethane. The concentrations of ethylene and vinyl chloride can be decreased to not more than 10 p.p.m. and not more than 20 p.p.m., respectively.