Abstract: The present invention refers to a process for direct C—H functionalization, the reagents used in the process and the use thereof for the direct C—H functionalization as well as the so-obtained products.

Abstract: To provide a novel process for producing p-dichlorobenzene satisfying both of high selectivity of p-dichlorobenzene and high conversion of chlorine at the same time.

Abstract: A method for recovering and reusing a ring-halogenation catalyst comprises: (A) contacting an aromatic compound with chlorine or bromine in the presence of a catalyst composition, where the catalyst composition comprises at least one salt comprising a Group 4-13 metal, a lanthanide metal, or an actinide metal; and at least one organic counterion derived from an organic acid having a pKa relative to water of 0 or greater; and at least one organic sulfur compound; to form a first product mixture comprising a monochloro or a monobromo aromatic compound and a Group 4-13 metal halide, a lanthanide metal halide or an actinide metal halide; (B) separating the metal halide from the first product mixture; and (C) contacting at least a portion of the metal halide and an aromatic compound with chlorine or bromine, and at least one organic sulfur compound; to form a second product mixture comprising a monochloro or a monobromo aromatic compound and a Group 4-13 metal halide, a lanthanide metal halide or an actinide metal

Abstract: A method for the nuclear chlorination of ortho-xylene using a chlorinating agent in the presence of at least one Friedel-Crafts catalyst and chloro-substituted 2,8-dimethylphenoxathiin as co-catalyst.

Abstract: The invention relates to a process for preparing 4-chlorobiphenyl by (a) reacting biphenyl and chlorine in the presence of one or more ring-chlorination catalysts, and (b) subjecting the reaction mixture obtained in step (a) to fractional distillation to obtain 4-chlorobiphenyl.

Abstract: The work-up of the gaseous products from the thermal cracking of 1,2-dichloroethane is simplified if the cracking gases are cooled to a temperature range of about 150 to 180° C., only a subsidiary proportion, which comprises all the coke formed, being condensed and fed to a separate work-up.

Abstract: This invention relates to an improved process for producing 2,6-dichloro-3,5-di(secondary or tertiary alkyl)toluene represented by the following formula (I). The process comprises chlorinating 3,5-di(secondary and tertiary alkyl)toluene represented by the following formula (II) by reacting with a chlorinating agent in the presence of a Lewis acid together with an aromatic sulfur compound represented by the formula (III) as a promoter: wherein R1 and R2 are independently a secondary alkyl or tertiary alkyl group, Ar1 and Ar2 are independently an unsubstituted or substituted aromatic ring, and n is 1 or 2.

Abstract: Disclosed is a method of increasing the percentage of certain isomers made when di or tri-substituted benzenes are chlorinated in the presence of a Friedel-Crafts catalyst. The use of about 0.001 to about 1 wt % a cocatalyst during chlorination alters the isomeric ratio of the product mixture. In particular, the percentage of the 2,5-isomer is increased when said substituted benzene is ortho or meta-substituted, the percentage of the 3,4-isomer is increased when said substituted benzene is para-substituted, and the percentage of the 2,4,5-isomer is increased when said substituted benzene is 2,4-disubstituted, 3,4-disubstituted, or 2,5-disubstituted.

Abstract: Disclosed is a method of making high purity 2,4- and 3,4-dichlorotoluene from parachlorotoluene that contains some metachlorotoluene. About 0.0001 to about 5 wt % of a Friedel-Crafts catalyst and about 0.5 to about 10 equivalents of a brominating agent are added to the parachlorotoluene. The metachlorotoluene is brominated, but most of the parachlorotoluene is not brominated. Without separating the brominated products from the unbrominated products, about 0.5 to about 1.5 equivalents of a chlorinating agent are added, whereby only the unbrominated products (i.e., the parachlorotoluene) are chlorinated. The resulting 2,4-dichlorotoluene and 3,4-dichlorotoluene can be separated by distillation.

Abstract: Disclosed is a method for making high purity .alpha.-chloroxylenes. A composition is formed of about 15 to about 80 wt % of a xylene and about 20 to about 85 wt % of a solvent. The solvent can be toluene, ring halogenated toluene, benzotrichloride, ring halogenated benzotrichloride, benzotrifluoride, ring halogenated benzotrifluoride, .alpha.,.alpha.,.alpha.,.alpha.',.alpha.',.alpha.'-hexafluorometaxylene, .alpha.,.alpha.,.alpha.,.alpha.',.alpha.',.alpha.'-hexafluoroparaxylene, or a mixture thereof. The composition is heated to about 70 to about 160.degree. C. No base is present in the composition. Chlorine gas is sparged through the composition and chlorine free radicals are generated therein. The chlorine free radicals can be generated either with UV light or by means of a chlorine free radical initiator.

Abstract: Disclosed is a method of making a chlorobenzene having the general formulas ##STR1## where X is Cl or F, and X' is X or CF.sub.3. A compound having the formula ##STR2## is sulfonated using at least 2 moles per mole of said compound of a sulfonating agent selected from the group consisting of sulfuric acid, chlorosulfonic acid, and mixtures thereof, to produce a sulfonated compound. The sulfonated compound is chlorodesulfonated to produce a chlorobenzene, such as 1,2,4-trichlorobenzene. Preferably, the starting material is ortho-dichlorobenzene.

Abstract: A process for the para-directed nuclear chlorination of an alkylbenzene, such as toluene, comprises reacting the alkylbenzene with chlorine in the presence of a Lewis acid catalyst and a novel co-catalyst of the formula: ##STR1## where Z is ##STR2## ; and R is Cl, Br, F, C.sub.1 to C.sub.8 alkyl to C.sub.1 to C.sub.8 alkoxy; x and y are each hydrogen, or taken together form a fused cyclopentyl or cyclohexyl ring; n is 0, 1 or 2, with the proviso that when Z is [3], n is 0 or 1.

Abstract: Dichlorobenzene having an increased p-content and a greatly reduced m-content is obtained by ring chlorination of benzene or chlorobenzene in the presence of Friedel-Crafts catalysts if the reaction is carried out in the presence of co-catalysts of the formula (I) ##STR1## wherein X represents fluorine, chlorine, bromine, trifluoromethyl or pentafluoroethyl andA represents 2 hydrogen atoms or the group --CH.dbd.CH--CH.dbd.CH--.

Abstract: A regioselective process is provided for preparing 4-bromo-o-xylene in an isomer mixture of 4-bromo-o-xylene and 3-bromo-o-xylene by combining a molar excess of bromine with o-xylene. The produced 3-bromo-o-xylene isomer preferentially reacts with the excess bromine to produce dibromo-o-xylenes. The weight ratio of the 4-bromo-o-xylene to the 3-bromo-o-xylene in the product isomer mixture can be as high as about 97:3. Concurrent production of alpha-bromo-o-xylene is avoided by conducting the admixing in either darkness or in sulfur dioxide solution. The dibromo-o-xylene by products are easily separated by subsequent vacuum distillation or similar expedients.

Abstract: Aromatic hydrocarbons monosubstituted by straight-chain or branched C.sub.1 -C.sub.12 -alkyl or by Chd 3-C.sub.8 -cycloalkyl can be chlorinated in the aromatic ring in the liquid phase in the presence of Friedel-Crafts catalysts if cyclic amidines which are oxy-sustituted on the exocyclic N atom are employed as co-catalysts. An increased proportion of the p-isomer is obtained in this reaction.

Abstract: In the preparation of 2-chloro-4-nitro-alkylbenzene by reaction of 4-nitro-alkylbenzene with elemental chlorine or chlorine-releasing compounds in the presence of a Friedel-Crafts catalyst in the liquid phase, particularly high selectivities in respect of the target compounds chlorinated exclusively in the 2-position are achieved if a dibenzo-condensed sulphur heterocycle of the formula ##STR1## having the meanings given in the description for R.sup.1 to R.sup.8, X and n, is used as co-catalyst.

Abstract: A process for synthesizing 3,5-dichloroalkylbenzene and recovering 1,3-dichlorobenzene from a starting mixture of 1,3- and 1,4-dichlorobenzenes. The process includes the sequential steps of selectively alkylating the 1,3-dichlorobenzene in the starting mixture; isomerizing a portion of the 2,4-dichloroalkylbenzene produced to 3,5-dichloroalkylbenzene; separating the 1,4-dichlorobenzene from the isomeric mixture of dichlorocumenes; and selectively transalkylating the dichlorocumenes to yield alkylbenzene, 3,5-dichloroalkylbenzene and 1,3-dichlorobenzene. By selectively alkylating only a portion of the 1,3-dichlorobenzene, the reaction products are obtained in good yield and substantially free of undesirable by-products.

Abstract: A regioselective process is provided for preparing 4-bromo-o-xylene in an isomer mixture of 4-bromo-o-xylene and 3-bromo-o-xylene by combining bromine with o-xylene in liquid sulfur dioxide medium. A bromine to o-xylene mole ratio of about 0.4:1 to about 1:1 is utilized at a temperature in the range of about -20.degree. C. to about 40.degree. C. While preferred temperatures are in the about -15.degree. C. to about -9.degree. C. range, temperatures above about -9.degree. C. can be used by maintaining the reactant solution under pressure. A product isomer mixture can be isolated by vacuum distillation. A 92:8 weight ratio mixture of 4-bromo-o-xylene and 3-bromo-o-xylene is thus obtainable.

Abstract: 4,4'-Dibromobiphenyl is selectively produced in high yields by actively brominating biphenyl in a reaction medium containing at least one strong acid having a pKa of at most 4, e.g., a carboxylic or sulfonic acid, and, optionally, a reaction solvent.

Abstract: Aromatic hydrocarbons which are monosubstituted by straight-chain or branched C.sub.1 -C.sub.12 -alkyl or by C.sub.3 -C.sub.8 -cycloalkyl can be chlorinated in the presence of Friedel-Crafts Catalysts in liquid phase on the aromatic ring if cyclic benzo-fused imines or benzo[f]-1,4-thiazepines are used as co-catalysts. This makes it possible to obtain a higher proportion of p-isomers.

Abstract: Aromatic hydrocarbons which are monosubstituted by straight-chain or branched C.sub.1 -C.sub.12 -alkyl or by C.sub.3 -C.sub.8 -cycloalkyl can be chlorinated in the presence of Friedel-Crafts Catalysts in liquid phase on the aromatic ring if 1,6-benzothiazocins are used as co-catalysts. This makes it possible to obtain a higher proportion of p-isomers.

Abstract: Monohalogenated cyclobutarenes are prepared by halogenating a cyclobutarene in the presence of an organic complexing agent, an acid scavenger, or water. Faster reaction rates highly selective to monohalogenated cyclobutarenes are obtained without conventional heavy metal or halogen catalysts.

Abstract: A p-substituted halobenzene derivative, which is very valuable in industry, can be obtained by halogenation of benzene and/or a benzene derivative in the liquid phase using, as a catalyst, a faujasite type zeolite in the presence of any one member selected from the group consisting of sulfur-containing compounds, nitrogen-containing organic basic compounds, salts of said nitrogen-containing organic basic compounds, and a mixture of said nitrogen-containing organic basic compounds and salts thereof.

Abstract: Aromatic hydrocarbons are chlorinated in the nucleus in the presence of Friedel-Crafts catalysts and in the presence of co-catalysts in the liquid phase by using thiazepines as co-catalysts.

Abstract: Monobrominated cyclobutarenes are prepared by brominating a cyclobutarene in the presence of an organic complexing agent, an acid scavenger, or water. Faster reaction rates highly selective to monobrominated cyclobutarenes are obtained without conventional heavy metal or halogen catalysts.

Abstract: Disclosed herein is a process for producing 2,5-dichlorotoluene which is useful as a monomer of heat-resistant polymers and an intermediate raw material for medicines, agricultrual chemicals and various organic synthetic substances, the process giving 2,5-dichlorotoluene at a high selectivity and in a high yield and comprising the steps of chlorinating 4-t-alkyltoluene or 4-isopropyltoluene in the presence of a catalyst, thereby obtaining a 2,5-dichlorocompound, and bringing the formed 2,5-dichlorocompound into contact with toluene in the presence of a catalyst, thereby subjecting the 2,5-dichlorocompound to transalkylation.

Abstract: The invention relates to a process for the removal of m-dichlorobenzene from dichlorobenzene mixtures by chlorination in the liquid phase at elevated temperature in the presence of Friedel-Crafts catalysts, the chlorination being carried out with addition of sulphur, sulphur compounds, iodine and/or iodine compounds and the chlorination mixture then being worked up in the usual way.

Abstract: In the ring chlorination of toluene, a particularly high proportion of p-chlorotoluene is obtained by using in addition to the customary Lewis acid catalysts as cocatalyst a chlorination product of 2,8-dimethylphenoxathiin which comprises in the main 1,3,7,9-tetrachloro-2,8-dimethylphenoxathiin of the formula ##STR1##

Abstract: Process for the preparation of 6-chloro-2,4-dinitroaniline by chlorination of 2,4-dinitroaniline with sodium hypochlorite in water using acid, which comprises carrying out the chlorination in the presence of a mineral acid or strong organic acid at a pH value .ltoreq.0 and in the presence of a dispersing agent at temperatures of about 40.degree. to 50.degree. C. and, when the chlorination has ended, either (a) filtering the resulting acid aqueous dispersion hot and washing the filtered reaction product with hot aqueous alkali solution, or (b) initially rendering the resulting acid aqueous dispersion alkaline with aqueous alkali solution and then filtering the mixture hot and subsequently washing the filtered reaction product with hot dilute mineral acid.

Abstract: Para-chlorotoluene is prepared selectively at high yield by nuclear chlorination of toluene, in the presence of a Lewis acid catalyst, and a co-catalyst comprising at least one compound selected from the group consisting of phenoxthine derivatives and highly chlorinated phenoxthine derivatives obtained by chlorinating said phenoxthine derivatives at higher degree, said phenoxthine derivatives being represented by the general formula of: ##STR1## wherein R represents methyl group or groups at the position-1 and/or position-3,m is zero or an integer of 1 or 2,X is hydrogen or chlorine atom, andY is chlorine atom or methyl group;and whereinm is an integer of 1 or 2 andX is hydrogen or chlorine atom when Y is chlorine atom,X is chlorine atom when Y is methyl group and m is zero, andX is hydrogen atom when Y is methyl group and m is an integer of 1 or 2.

Abstract: The meta-dihalobenzenes are selectively 2-chlorinated by reacting same with a chlorine donor, e.g., hexachlorobenzene or pentachlorobenzene, in the presence of at least one alkali metal amide, e.g., sodamide, and at least one compound which complexes the cation of such at least one alkali metal amide.

Abstract: A process for the preparation of monochlorinated and dichlorinated bis-(perhalomethyl)-benzenes of the formula (I) by reacting bis-(perhalomethyl)-benzenes of the formula (II) with elementary chlorine in chlorosulfonic acid as the reaction medium, at a temperature of, preferably, 0.degree. to 10.degree. C. The present invention makes it possible to obtain pure compounds of the formula (I), in high yields, in a single process step.

Abstract: Process for nuclear chlorination of non-phenolic aromatic compounds, said process comprising contacting and reacting a non-phenolic aromatic compound having a net Hammett .sigma. value of about -0.1 to about 2.0 with chlorine monoxide in the presence of at least one-half an equivalent amount, based on the chlorine monoxide, of an acid having a pK.sub.a no greater than that of trichloroacetic acid, provided, however, when the net Hammett .sigma. value is about 0.7 to about 2.0, the acid has a pK.sub.a no greater than that of trifluoroacetic acid.

Abstract: p-Chloroalkylbenzene is selectively produced by chlorinating an alkylbenzene in the presence of a phenoxthine compound having the formula ##STR1## wherein X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are the same or different and respectively represent hydrogen atom; an electron attractive group or an electron donative group and a Lewis acid or its precursor as a catalyst.The process for producing a p-chloroalkylbenzene can be repeatedly carried out by separating the resulting a p-chloroalkylbenzene and adding a hydrogen halide to the residual mixture containing the catalyst to activate the catalyst and chlorinating a newly added alkylbenzene.

Abstract: A process for the para-directed chlorination of alkylbenzenes comprises reacting an alkylbenzene with chlorine in the presence of a catalyst mixture previously prepared by the steps of (a) reacting sulfur monochloride with toluene or chlorotoluene in the presence of a Lewis acid catalyst, and (b) reacting the reaction product of step (a) with chlorine.