Abstract: A process for producing a chlorinated alkane in which an alkene or an alkane feedstock is contacted with chlorine in a chlorination zone to produce a reaction mixture containing the chlorinated alkane, wherein the chlorine supplied into the chlorination zone has an oxygen content of less than about 2000 ppmv and wherein: the chlorination zone is closed to the atmosphere, and/or the chlorination zone is operated under atmospheric or superatmospheric pressure, and/or the chlorination zone is operated under an inert atmosphere, and/or the content of dissolved oxygen in the alkene or alkane feedstock is less than 2000 ppm.

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: for Processes for converting a methane or a methane containing natural gas to a monohalogenated methane and other downstream basic commodity chemicals going through methanesulfonyl halide as a key intermediate, whereby following its formation, the methanesulfonyl halide is allowed to decompose under a substantially anhydrous condition, preferably in the presence of a catalyst complex, and whereby in addition to the monohalogenated halide, a hydrogen halide and a sulfur dioxide are also formed in the overall conversion, both of which may be recycled back to the beginning of the processes. Additionally, compositions utilizing such a key intermediate for the same purposes are also disclosed.

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: Processes for the production of chlorinated propenes are provided. The present processes make use of a feedstream comprising 1,2-dichloropropane, a by-product in the production of chlorohydrin, as a low cost starting material, alone or in combination with 1,2,3-trichloropropane. Selectivity of the process is enhanced over conventional processes employing successive chlorinations and/or dehydrochlorinations, by conducting at least one chlorination in the presence of an ionic chlorination catalyst. The present processes may also generate anhydrous HCl as a byproduct that can be removed from the process and used as a feedstock for other processes, providing further time and cost savings.

Abstract: Processes for the production of chlorinated propenes are provided. The present processes make use of a feedstock comprising 1,2,3-trichloropropane and chlorinates the 1,1,2,3-tetrachloropropane generated by the process prior to a dehydrochlorination step. Production of the less desirable pentachloropropane isomer, 1,1,2,3,3-pentachloropropane, is thus minimized. The present processes provide better reaction yield as compared to conventional processes that require dehydrochlorination of 1,1,2,3-tetrachloropropane prior to chlorinating the same. The present process can also generate anhydrous HCl as a byproduct that can be removed from the process and used as a feedstock for other processes, while limiting the production of waste water, thus providing further time and cost savings.

Abstract: Processes for the production of tetrachloromethane are provided. The present processes involve catalyzing the chlorination of a feedstream comprising partially chlorinated methanes with a free radical initiator. Cost savings are thus provided relative to conventional processes that require the use of high temperatures and/or pressures, and safety concerns are alleviated or eliminated.

Abstract: Methods of halogenating a carbon containing compound having an sp3 C—H bond are provided. Methods of fluorinating a carbon containing compound comprising halogenation with Cl or Br followed by nucleophilic substitution with F are provided. Methods of direct oxidative C—H fluorination of a carbon containing compound having an sp3 C—H bond are provided. The halogenated products of the methods are provided.

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: Processes for converting a methane or a methane containing natural gas to a monohalogenated methane and other downstream basic commodity chemicals going through methanesulfonyl halide as a key intermediate, whereby following its formation, the methanesulfonyl halide is allowed to decompose under a substantially anhydrous condition, preferably in the presence of a catalyst complex, and whereby in addition to the monohalogenated halide, a hydrogen halide and a sulfur dioxide are also formed in the overall conversion, both of which may be recycled back to the beginning of the processes. Additionally, compositions utilizing such a key intermediate for the same purposes are also disclosed.

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 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: Process for preparing 2-bromo-4,4?-dialkylbiphenyl, wherein 4,4?-dialkylbiphenyl is, in the presence of catalytic amounts of iodine and, if appropriate, in a halogenated hydrocarbon as solvent, reacted with bromine.

Abstract: A method for preparing a composition of the formula in a yield greater than 50% where R1 is C 1-20 comprising the steps of combining fluorene or dibromo flourene, an excess of alkali metal hydroxide and a halogenated alkyl in the presence of a phase transfer catalyst but in the absence of a polar aprotic solvent; heating the combination; and separating the dialkylated fluorene or dialylated dibromo fluorene. If the flourene is not brominated prior to alkylation, the dialkylated fluorene is then brominated.

Abstract: The invention relates to a process and a device for the dissolution of salt that is hardly soluble, especially sodium chloride and other poorly soluble salts in 1,2 dichloroethane, which primarily are to be used in direct chlorination plants for the production of 1,2 dichloroethane. This aim is achieved by mounting an ultrasonic transducer (sonotrode) in the dissolution chamber which is filled with a suspension of salt crystals and 1,2 dichloroethane. The suspension is sent through a filter upon dissolution of the salt.

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: This invention relates to a novel process which comprises feeding a mixture formed from diphenylethane and bromine to a stirrable reaction mass comprised of bromine and a bromination catalyst to yield a decabromodiphenylethane wet cake which can be most economically treated to provide a high quality decabromodiphenylethane product.

Abstract: This invention relates to a novel process which comprises feeding a mixture formed from diphenylethane and bromine to a stirrable reaction mass comprised of bromine and a bromination catalyst to yield a decabromodiphenylethane wet cake which can be most economically treated to provide a high quality decabromodiphenylethane product.

Abstract: There is disclosed a catalyst support for selective gas phase reactions in a tubular fixed bed reactor comprising a metallic monolith having channels the walls of which are adapted to receive a catalytically active phase or an intermediate layer acting as a carrier for a catalytically active phase. The monoliths are coated with catalytically active material and loaded lengthwise into tubular reactors, the channels being parallel to the length of the reactors. The catalysts are particularly useful in the chlorination/oxychlorination of alkenes and alkanes, and the oxidation of alkenes. Compared with the use of conventional catalysts in pellet form or in the form of ceramic monoliths the catalysts of the invention offer greater yields and selectivity, the avoidance of hot spots, greater catalyst life and flexibility in use.

Abstract: The invention relates to a process for the preparation of halogenomethylcyclopropanes.

Abstract: A process for the preparation of a selectively fluorinated organic compound, which process includes reaction of a precursor of said organic compound, the precursor containing at least one Group VI element selected from sulfur, selenium and tellurium, with a fluorinating agent and another halogenating agent and characterized in that the fluorinating agent is elemental fluorine.

Abstract: The present invention concerns a novel process for the selective trihalogenation of ketones employing organic halogen salts.

Abstract: Process for preparing the (E)-isomer of a compound (II) by contacting the (E) or (Z) isomer of the 2-methylphenyl precursor, or a mixture of both, with bromine in an organic solvent, in the presence of a polymeric base and light.

Abstract: 1,1,1-Trichloroethane (viz., methylchloroform) and 1,1,2-trichloroethane are produced in the same reactor by feeding molecular chlorine and chloroethene (viz., vinyl chloride) as well as 1,1-dichloroethane to the reactor. The ratios at which the two trichloroethanes are produced can be easily controlled by controlling the relative ratios of 1,1-dichloroethane and chloroethene introduced to the reactor. The reactions are conducted in the liquid phase in the presence of free radical initiator.

Abstract: 1,1,1-Trichloroethane (viz., methylchloroform) and 1,1,2-trichloroethane are produced in the same reactor by feeding molecular chlorine and chloroethene (viz., vinyl chloride) as well as 1,1-dichloroethane to the reactor. The ratios at which the two trichloroethanes are produced can be easily controlled by controlling the relative ratios of 1,1-dichloroethane and chloroethene introduced to the reactor. The reactions are conducted in the liquid phase in the presence of free radical initiator.

Abstract: The invention relates to a process for selectively producing alkyl halides from alkanes, such as methane and ethane at relatively mild temperatures and pressures in an organic liquid phase in the presence of halogen and transition metal complex. The alkane may be neat if in a liquid form, or may be solubilized with a suitable organic solvent, if the alkane not a liquid at reaction conditions. The reaction is for a time, under conditions of temperature and pressure and in effective amounts that will permit the formation of alkyl halides. Optional hydrolysis to the corresponding alcohols may follow. The alkyl halides have utility as precursors for alternative fuels, such as methanol.

Abstract: Disclosed is a process for the coproduction of (1) an alkyl iodide and (2) an .alpha.-iodocarboxylic acid, a mono-.alpha.-iodocarboxylic anhydride or a mixture thereof which comprises contacting a mixture of an iodine compound and a carboxylic anhydride with a peroxide at an elevated temperature.

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: 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: Free chlorine values are removed by radical chlorination from uncombined admixtures thereof, notably admixtures of free chlorine and at least one halogenated organic compound that is not completely chloro-substituted.

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 higher chloroalkanes, advantageously the higher chloromethanes, are continuously produced from at least one lesser chloroalkane, by (i) continuously introducing chlorine and said at least one lesser chloroalkane into a stream of reaction medium continuously and essentially autogenously recirculating in a loop circuit which comprises an essentially vertical principal reaction zone, (ii) continuously chlorinating said at least one lesser chloroalkane in said essentially vertical principal reaction zone, and (iii) continuously withdrawing higher chloroalkane product from said stream of essentially autogenously recirculating reaction medium.

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: The substitution chlorination reactions of organic compounds are carried out by means of molecular chlorine, using, as a radical initiator, decachlorobutane or an octachlorobutane such as octachlorobut-1-ene or a mixture containing these two products.Good degrees of conversion and good yields are obtained at moderate temperatures.The process is, for example, applicable to the substitution chlorination of benzene and of chloroform.

Abstract: A process is disclosed for preparing 1,1,2,3-tetrachloropropene comprising allylic rearrangement of 2,3,3,3-tetrachloropropene using a substantially anhydrous ferric chloride catalyst. Alternatively, 1,1,2,3-tetrachloropropene is prepared by dehydrochlorination of 1,1,1,2,3-pentachloropropane using a ferric chloride catalyst. Process schemes commencing with the preparation of the precursor 1,1,1,3-tetrachloropropane by reaction of ethylene with carbon tetrachloride are also disclosed.

Abstract: This invention relates to an improved liquid phase chlorination process for the chlorination of methyl chloride to preferentially produce methylene chloride. The chlorine is provided to the reaction mixture in a mole percent, based upon the total moles of chlorine and methyl chloride in the mix, which ranges from about 16 mole percent to about 2 mole percent.

Abstract: The process is an improvement over the chlorination of EDC in a boiling bed. The reactants, chlorine and dichloroethane (either 1,1- or 1,2-) are mixed in the vapor phase and passed over a molecular sieve which serves as a catalyst to produce 1,1,2-trichloroethane.

Abstract: In a process for producing an iodo-aromatic compound which comprises iodinating an aromatic compound having an electron-donating substituent bonded to the benzene ring with iodine in the presence of a solvent, the improvement wherein about 1/2 to about 10 moles, per mole of iodine added to the reaction system, of nitrogen dioxide (NO.sub.2) is added in the form of NO.sub.2 to the reaction system, and the reaction is carried out in the presence of nitrogen dioxide.

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 process is disclosed for preparing 1,1,2,3-tetrachloropropene comprising allylic rearrangement of 2,3,3,3-tetrachloropropene using a substantially anhydrous ferric chloride catalyst. Alternatively, 1,1,2,3-tetrachloropropene is prepared by dehydrochlorination of 1,1,1,2,3-pentachloropropane using a ferric chloride catalyst. Process schemes commencing with the preparation of the precursor 1,1,1,3-tetrachloropropane by reaction of ethylene with carbon tetrachloride are also disclosed.

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: 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: In the preparation of methylchloroform by vapor phase chlorination of 1,1-dichloroethane, the formation of undesirable chlorohydrocarbon reaction products is suppressed by conducting the vapor phase reaction in the presence of a controlled amount of elemental oxygen.

Abstract: There is disclosed a process for the production of hexachlorocyclopentadiene comprising the steps of:1. Reacting liquid cyclopentadiene and chlorine at a temperature of from about 0.degree. to about 100.degree. C. until an average of at least 4 chlorine atoms has been added per mole of cyclopentadiene to form a first-stage product;2. heating the resultant liquid reaction product of Step 1 in a second stage at a temperature of from about 140.degree. C. to below about 200.degree. C. with chlorine in the presence of from about 0.0001% to about 5.0% (by weight) of an aromatic compound until the reaction products of Step 1 contain an average of about 6 chlorine atoms per molecule, based on cyclopentadiene starting material; wherein said aromatic compound contains from 1 to 3 aromatic rings; at least one of the rings containing a nitrogen atom;3. vaporizing and heating the resulting reaction products of Step 2 in a third stage in the presence of chlorine to a temperature of above 450.degree. C.