Abstract: Substituted 2-haloanilines are prepared from the correspondingly substituted 2,4-dichloro- or 2,4-dibromoanilines by selectively reducing a chloro or bromo substituent para to a protected amino group in the presence of the same halogen as an ortho substituent. The selective reductions are accomplished by protecting the amino function of the aniline with two protecting groups, e.g., as the diacetanilide or the succinimide.

Abstract: 2-Chloro and 2,6-dichloroanilines, optionally substituted in the 3-, 5-, and/or 6-position are prepared from the corresponding anilides by selective bromination, chlorination, reduction and hydrolysis. The selectivity of the process for introducing chlorines ortho to the amino group is very high.

Abstract: A process for the production of 2,4-dihaloaniline, especially 4-bromo-2-fluoroaniline, via the halogenation (bromination) of 2-haloaniline (2-fluoroaniline) in the presence of quaternary ammonium halide (bromide) catalyst in an inert solvent. The yield and selectivity are very high and the inventive method includes continuous processing with recycle of the catalyst/solvent mixture.

Abstract: The invention relates to the compounds of the formula: ##STR1## in which R.sub.1 and R.sub.2 denote, independently of one another, a hydrogen atom, a C.sub.1 -C.sub.4 alkyl radical or a C.sub.2 -C.sub.3 mono- or polyhydroxyalkyl radical,Z and Z' denote, independently of one another, a C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.4 hydroxyalkyl radical, with the proviso that, when R.sub.1 and R.sub.2 simultaneously denote a hydrogen atom, Z and Z' do not simultaneously denote a methyl radical, and to their addition salts with an acid, to a process for preparation thereof and also to their use, by way of couplers, in an aqueous vehicle, in combination with at least one oxidation dye percursor of the para type, for the dyeing of human hair.The invention also relates to the intermediate compounds of the formula: ##STR2## in which R' denotes a hydrogen atom, a C.sub.1 -C.sub.4 alkyl radical, a C.sub.2 or C.sub.3 mono- or polyhydroxyalkyl radical, or an acetyl or .beta.

Abstract: A process for preparing a 2,2,6,6-tetrahalocyclohexaneimine derivative (I) which comprises reacting a 2,2,6,6-tetrahalocyclohexanone with a primary amine or ammonia in the presence of a Lewis acid, a process for preparing a 2,6-dihaloaniline derivative (II) which comprises subjecting the 2,2,6,6-tetrahalocyclohexaneimine derivative (I) to dehydrohalogenation in the presence or absence of a catalyst, and an N-phenyl-2,2,6,6-tetrahalocyclohexaneimine. According to the process of the present invention, the 2,2,6,6-tetrahalocyclohexaneimine derivative (I) can be prepared from inexpensive starting materials in high yield through a few steps. Also, the 2,6-dihaloaniline derivative (II) can be prepared from inexpensive starting materials in high yield and high purity through a few steps. Further, the N-phenyl-2,2,6,6-tetrahalocyclohexaneimine is very useful in the preparation of N-phenyl-2,6-dihaloaniline.

Abstract: Disclosed is a process for the preparation of a perfluoroorganic compound, which comprises fluorinating a partially fluorinated or unfluorinated organic compound having carbon-to-fluorine bonds under mild conditions and then, contacting the resulting reaction mixture with a fluorine gas at a temperature of 110.degree. to 180.degree. C.

Abstract: Disclosed is a process for the preparation of a perfluoro organic compound, which comprises fluorinating a partially fluorinated or unfluorinated organic compound having carbon-to-fluorine bonds under mild conditions and then, contacting the resulting reaction mixture with a fluorine gas at a temperature of 110.degree. to 180.degree. C.

Abstract: A process of selectively preparing p-bromo-o-alkylanilines (e.g. 4-bromo-2-methylaniline) by reacting o-alkylanilines (e.g., 2-methylaniline) with unadsorbed bromine in a solvent selected from the group consisting of an inert di- tri- or tetrahaloaliphatic hydrocarbon (e.g., dichloromethane and dibromomethane), an alkyl nitrile (e.g., acetonitrile) and mixtures thereof.

Abstract: 4-Bromoaniline hydrobromides of formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of the other C.sub.1 -C.sub.10 alkyl or C.sub.3 -C.sub.7 cycloalkyl, are prepared by brominating an aniline hydrohalide of formula II ##STR2## wherein X is chlorine or bromine and R.sup.1 and R.sup.2 are as defined above, in the presence of an inert organic solvent.

Abstract: The invention relates to a process for the preparation of chloronitroanilines or chloronitrophenols, which comprises chlorinating nitroanilines or nitrophenols in hydrochloric acid by adding simultaneously separate streams of nitroanilines or nitrophenols and of a chlorinating agent to said hydrochloric acid. The process affords pure products in good yield. An accumulation of chlorine during the reaction is avoided.Chloronitroanilines and chloronitrophenols are useful intermediates for the snythesis of disperse dyes.

Abstract: A process for chlorinating compounds containing a carbon atom bonded to a hetero-atom selected from the group consisting of oxygen, nitrogen and sulfur; said process comprises contacting the carbon hetero-atom containing compound with a chloro phosphorus complex of the formulaRP.sup..sym. CL.sub.3 P.sup..crclbar. Cl.sub.6wherein R is selected from the group consisting of aryl, substituted aryl, alkyl and substituted alkyl, so that the hetero-atom is replaced by at least one chlorine atom; compounds capable of being chlorinated can include, for example, carboxylic acids, acid chlorides, ketones, aldehydes, alcohols, epoxides, esters, anhydrides, ethers, thiols, and aromatic nitro groups; the reaction can be extended to compounds containing the carbon to chlorine bond alpha to a carbon atom containing at least one hydrogen atom, it can be further dehydrochlorinated, e.g., by either heating to a temperature ranging from about 50.degree. C. to about 300.degree. C. or by reaction with a base selected, e.g.

Abstract: A process for the preparation of trifluoromethylanilines. Hydrolysis and exchange fluorination of a para-trihalomethyl benzene isocyanate or carbamyl halide are carried out in liquid hydrofluoric acid.

Abstract: A method for the preparation of 2-halogenoresorcinols having the following formula I ##STR1## where X represents a halogen atom and R and R.sub.1 may be the same or different and represent a hydrogen atom or a free organic functional or functionally modified group or a hydrocarbon group, which may be substituted by one or more free organic functional or functionally modified groups and R and R.sub.1 jointly may also represent a free organic functional or functionally modified group or a hydrocarbon group which may be substituted by one or more free organic functional or functionally modified groups, and esters, ethers, or salts thereof.The method comprises sulfonating the corresponding resorcinols which do not contain a halogen in the 2-position and then halogenating the sulfonic acids thus obtained. The halogenated sulfonic acids thereby obtained are subsequently protodesulfonated by acid hydrolysis and, if desired, any functional groups which may be present can be modified.

Abstract: A process for producing 1,3-bis(3-aminophenoxy)-benzenes which are very useful as a monomer for heat-resistant high molecular weight polymers is provided, which process comprises dehalogenating a bis(3-aminophenoxy)-halogenobenzene by its reduction, which compound is selected from the group consisting of 1,3-bis(3-aminophenoxy)-5-halogenobenzenes, 1,3-bis(3-aminophenoxy)-2,4-dihalogenobenzenes and 1,5-bis(3-aminophenoxy)-2,4-dihalogenobenzenes, these raw material compounds being respectively obtained by reacting a 1,3,5-trihalogenobenzene, a 1,2,3,4-tetrahalogenobenzene or a 1,2,4,5-tetrahalogenobenzene with 3-aminophenol in the presence of a dehydrohalogenating agent.

Abstract: A process for the preparation of compounds containing a difluoromethylene or trifluoromethyl group. A compound containing a carbonyl group, preferbly an acid, acid halide, amide, ketone or any compound containing a perhaloalkylcarbonyl moiety is placed, in anhydrous liquid hydrofluoric acid, in contact with boron trifluoride in a quantity such that the absolute pressure of boron trifluoride in the reaction system is at least one bar for a time sufficient to convert the carbonyl group to a difluormethylene or trifluoromethyl group.The compounds obtained are useful as synthesis intermediates in the pharmaceutical, plant-protection and dye industries, as anesthetics or as heat-transfer and lubricating fluids.

Abstract: This invention relates to a process for the preparation of meta-chloroanilines. Polychloroanilines containing at least one chloroatom in the meta position are reacted with hydrogen iodide in a homogeneous aqueous or organic medium at a temperature between about 90.degree. and 250.degree. C. Gaseous hydrogen and solid catalysts are not required. The meta-chloroanilines are useful in the manufacture of agrochemical intermediates.

Abstract: Process for the dehalogenation of aryl and alpha-araliphatic halides comprising contacting the aryl halide or alpha-araliphatic halide with hypophosphite salt, in the presence of a catalytic amount of a noble metal catalyst. This process is useful in the field of organic synthesis and for the removal of environmentally hazardous aryl and alpha-araliphatic halides, including polychlorinated biphenyls and dibenzo-p-dioxins.

Abstract: Preparation of 3,3'- or 3,4'-diaminobenzophenone by nitrating a chloronitrobenzophenone mixture obtained by the Friedel-Crafts reaction between 3- or 4-nitrobenzoyl chloride and chlorobenzene, and catalytically reducing and dechlorinating the resulting chlorodinitrobenzophenone mixture in the presence of a reduction catalyst and a dehydrochlorinating agent.

Abstract: This invention relates to a process for preparing 2'-methyl-2-haloacetanilides by selective catalytic hydrogenation of 2'-(halomethyl)-2-haloacetanilides. The 2'-(halomethyl)-2-haloacetanilides are initially prepared by reacting an ortho-(halomethyl) aniline or its anilinium salt with a haloacetyl halide.

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: Process for the preparation of 2,6-dichloro-4-nitroaniline by chlorination of 4-nitroaniline with chlorine bleaching liquor in water using acids, which comprises chlorinating 1 mole of 4-nitroaniline in 3-6 moles of hydrochloric acid (HCl) or nitric acid (HNO.sub.3) in the form of a dilute, aqueous acid in the presence of a dispersing agent which is stable under the reaction conditions, the chlorination initially being carried out at 5.degree. to 10.degree. C. and then at 15.degree.-20.degree. C. and, finally, after 90-95% of the 2-chloro-4-nitroaniline intermediately formed has been converted into 2,6-dichloro-4-nitroaniline, the temperature of the aqueous suspension being increased from 15.degree.-20.degree. C. to 70.degree. C., without further addition of chlorine bleaching liquor, and then by post-chlorinating, by renewed addition of chlorine bleaching liquor, at temperatures between 20.degree. and 70.degree. C., bringing the pH of the aqueous suspension to 9.

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: 3,3'- or 3,4'-diamino benzophenone is prepared by catalytically reducing and dehalogenating, in the presence of a reduction catalyst and a dehydrohalogenation agent, a benzophenone compound or benzophenone compounds of the general formula ##STR1## in which X is a halogen atom at position 2 or 4 of the benzene ring and Y is hydrogen or a halogen atom and in which the nitro group is at position 3' or 4' of the benzene ring if Y is hydrogen, while Y is at position 4' and the nitro group is at position 3' of the benzene ring if Y is a halogen atom.

Abstract: Preparation of 3,3'- or 3,4'-diaminodiphenylmethane by catalytically reducing and dechlorinating, in the presence of a reduction catalyst, a dinitrobenzophenone compound having the formula ##STR1## wherein X is chlorine and attached to a position 4 or 6 on the benzene ring, and Y is hydrogen or chlorine with the proviso that when Y is hydrogen, the nitro group is attached to a position 3' or 4', and when Y is chlorine, Y is attached to a position 4' and the nitro group is attached to a position 3'.

Abstract: Process for the selective preparation of metachloroanilines.It is carried out by the hydrodechlorination of polychloroanilines or polychloronitrobenzenes with hydrogen, in the liquid phase and in an acid medium, under the action of heat and under pressure, in the presence of a noble metal used in association with a heavy metal.These meta-chloroanilines are intermediates especially for active plant-protection substances.

Abstract: A process is disclosed for the separation of p-fluoroaniline from a mixture, containing aniline and p-fluoroaniline, by contacting the mixture with a mineral acid in the presence of an organic solvent. The corresponding salt of p-fluoro-aniline is insoluble and can easily be isolated by conventional means such as filtration. If desired, the isolated salt can be converted to p-fluoroaniline by reaction with a base.

Abstract: Polymer-containing polyether polyamines containing terminal aromatically-bound amino groups are produced by in situ polymerization of a polyether polyamine with an olefinically unsaturated monomer. The polyether polyamine starting material must have terminal aromatic amino groups, a molecular weight of from 800 to 10,000 and an aromatic amino group content of from 0.3 to 16 wt. %. Suitable olefinically unsaturated monomers include .alpha.,.beta.-unsaturated nitriles, aromatic vinyl compounds, .alpha.,.beta.-unsaturated carboxylic acids and esters thereof, vinyl esters, vinyl halides, vinylidene halides, .alpha.,.beta.-unsaturated carboxylic acid amides and aminoalkyl esters of unsaturated carboxylic acids. Acrylonitrile/styrene mixtures are preferred monomers. The starting materials are employed in quantities such that the product modified polyether polyamine contains from 1 to 60 wt. % polymer or graft-polymer. The product polyamines are particularly useful in the production of polyurethanes.

Abstract: Process for the preparation of anilines substituted in the meta-position by a halogen atom.An aniline of the formula: ##STR1## in which: X' and X", R', R" and R"' are a halogen atom, alkyl (C.sub.1 -C.sub.4) or alkoxy (C.sub.1 -C.sub.4), one of the symbols X and one of the symbols R necessarily being a halogen and it being possible for one of the symbols X and one of the symbols R to be a hydrogen atom,is subjected to catalytic hydrogenation, in an anhydrous organic liquid phase, namely a chlorobenzene phase, in the presence of a halogen-containing hydracid and of a noble metal from group VIII of the periodic classification.

Abstract: 3,3'-diamino diphenylsulfones are prepared by catalytically reducing and dehalogenating, in the presence of a reduction catalyst and a dehydrohalogenation agent, a diphenylsulfone compound of the general formula ##STR1## in which X is a halogen atom and Y is hydrogen or a halogen atom.

Abstract: The invention relates to a process for the preparation of anilines which are m-substituted by chlorine, by selective dehalogenation of more highly chlorinated anilines in an acid medium in the presence of noble metal catalysts and in the presence of optionally substituted phenols.The 3-chloro- or 3,5-dichloroanilines obtainable by the process according to the invention are known intermediate products, and can be used for the preparation of plant protection agents.

Abstract: 2,4,6-Trichloroaniline is prepared by reaction of aniline, which is optionally substituted by halogen, with a chlorinating agent in the presence of inert organic solvents and/or diluents at elevated temperatures.

Abstract: Novel processes for making arylpropionic acids are described. One process comprises carboxylating particular Grignard compounds which are the products of a catalyzed reaction between corresponding arylmagnesium bromides and ethylene. Furthermore, the reaction making the particular Grignard compounds is itself novel. Also, an improved method is disclosed for making coupled aryl compounds useful as intermediates for making compounds having a pharmaceutical use. For example, particular biaryls may be used to make some of the Grignard compounds herein from which the arylpropionic acids are made. Finally, an improved bromination is disclosed giving high yields of 4-bromo-2-fluoroaniline, which is thereafter coupled with benzene, then used to make the arylmagnesium bromide reacted with ethylene to obtain the particular Grignard compound and subsequent desired arylpropionic acid, i.e. 2-(2-fluoro-4-biphenylyl)propionic acid.

Abstract: An improved process for the preparation of an m-halogen-substituted aniline from a polyhalogen substituted aniline by the reaction of the aniline with hydrogen in an acid medium is disclosed wherein the process is carried out in the presence of hydrogen iodide and/or a compound which under the reaction conditions yields hydrogen iodide and in the presence of an optionally substituted phenol.

Abstract: Process for the selective preparation of meta-chloroanilines.It is carried out by the hydrodechlorination of polychloroanilines or polychloronitrobenzenes with hydrogen, in the liquid phase, under the action of heat, at atmospheric pressure or under pressure, in the presence of a noble metal, in an anhydrous organic medium and in the presence of a Lewis acid.These meta-chloroanilines are intermediates especially for active plant-protection substances.

Abstract: (1) Process for the manufacture of 2,6-dichloro-4-nitroaniline.(2) This process consists in chlorinating paranitroaniline, with chlorine gas, in an aqueous solution of hydrochloric acid having a concentration of between 4 and 7.5 N, at the boil, at a temperature between 95.degree. and 110.degree. C.(3) This process makes it possible to obtain 2,6-dichloro-4-nitroaniline with an improved yield and an improved quality of product.

Abstract: There are provided novel substituted aniline intermediates, useful in the synthesis of certain substituted N-nitroanilines or salts thereof which may be used to elicit several desirable and advantageous biological responses in plants.

Abstract: Process for the preparation of 4-chloro-2,6-dialkylanilines, characterized in that the ammonium salts of the 2,6-dialkylanilines are reacted with a chlorination agent at -15.degree. to 100.degree. C. in the presence of an inert organic solvent and/or diluent and, if necessary, the presence of Friedel-Crafts catalysts, and 4-chloro-2,6-dialkylaniline is then liberated from the 4-chloro-2,6-dialkylanilinium salt obtained.

Abstract: Para-fluoroaniline is prepared by reaction of N-phenylhydroxylamine with anhydrous hydrogen fluoride at atmospheric pressure and reflux conditions.

Abstract: A method for the preparation of 2,4-dinitroaniline from 1-chloro-2,4-dinitrobenzene comprising adding ammonia to melted 1-chloro-2,4-dinitrobenzene in such dosages that the temperature of the mixture does not exceed 120.degree. C. and that the pressure does not exceed 3 bar. 6-halo-2,4-dinitroaniline may be produced from the so formed 2,4-dinitroaniline by neutralizing the suspension containing the 2,4-dinitroaniline with acid to give a pH of from the 6-halo-2,4-dinitroaniline. The 6-halo 2,4-dinitroaniline is useful in the preparation of dyestuffs.

Abstract: A process for the dechlorination of aromatic nitro or amino compounds consists in reacting anilines or nitrobenzenes which are polysubstituted by chlorine, with hydrogen, under the action of heat, in the presence of iodide or bromide ions, in the liquid phase and at low pressure.The process makes it possible selectively to obtain anilines which are chlorine-substituted in the meta-position.

Abstract: A process for the dechlorination of aromatic nitro or amino compounds consists in reacting anilines or nitrobenzenes which are polysubstituted by chlorine, with hydrogen, under the action of heat, in the presence of cations (Bi, Pb, Sn, Tl, Hg and Ag), in the liquid phase and at low pressure.The process makes it possible selectively to obtain anilines which are chlorine-substituted in the meta-position.

Abstract: A process for the dechlorination of aromatic nitro or amino compounds comprising reacting anilines or nitrobenzenes, which are polysubstituted by chlorine, with hydrogen, under the action of heat, in the presence of an excess of chloride ions, in the liquid phase and at low pressure.The process makes it possible selectively to obtain anilines which are chlorine-substituted in the meta-position.

Abstract: A method of preparing 2,4-difluoroaniline by reacting 2,4,5-trichloronitrobenzene with a fluorinating agent to form 2,4-difluoro-5-chloronitrobenzene which is then hydrogenated with hydrogen in the presence of a catalyst to form 2,4-difluoroaniline.

Abstract: Substituted N-alkylated aromatic amines are produced by reductively alkylating and dehalogenating the corresponding m-nitrobenzyl halides with pressurized hydrogen in the presence of a ketone and a platinum catalyst.