Butyryl Chloride Research Articles

Reactions of Dichloroxozirconium(IV) Octahydrate with Monocarboxylic Acid Chlorides

Dichloroxozirconium(IV) octahydrate reacts with acetyl, propionyl, butyryl and chloracetyl chlorides at low temperatures to form addition compounds of the parent carboxylic acid, ZrOCl2 · 2 RCO2H, but at higher temperatures the corresponding carboxylates of the type ZrO(RCO2)2 · RCO2H are obtained. Benzoyl chloride does not react at low temperatures, but at 60 °C gives an addition product ZrOCl2 · 2 C6H5CO2H, and at higher temperatures a substitution product ZrO(C6H5CO2)2 · 2 C6H5CO2H is obtained. Elemental analyses, molar conductance measurements, infrared spectral studies and thermal decompositions have been carried out to understand the nature of these compounds.

The kinetics and mechanism of polymerization of N-methyl-, N-butyl- and N-benzylcapryllactam initiated with hydrogen chloride

The polymerization of N-alkyl-8-oct anelactams (N-alkylcapryllactams) at 150—200°C is a first order reaction with respect to monomer and hydrogen chloride; both the activation energy and the frequency factor decrease with increasing size of the substituent. The polymerization initiated with butyryl chloride proceeds ten times slower than with hydrogen chloride or an equimolar mixture of butyryl chloride and dibutylamine hydrochloride. The main monomer fraction is incorporated into the polymer by a sequence of two reactions, namely, cleavage of N-alkyllactam with hydrogen chloride to N-alkyl-8-ami nooctanoyl chloride followed by its bimolecular condensation. However, the participation of sec-amine hydrochloride catalyzed polyaddition of lactams to the carbonyl chloride group cannot be excluded so far. Of the initiators of the polymerization of N-methyl-8-oc tanelactam (/), hydrogen chloride or lactam hydrochloride1 is the most effective. The effect of hydrogen chloride in the cationic polymerization of the above lactam consists in the deacylating cleavage of the amide bond with formation of N-methyl-8-am inooctanoyl chloride hydrochloride2

Sur la formation de composés bicycliques lors de réactions de Friedel–Crafts

The acylation of 1-methylcyclohexene with propionyl, butyryl, and benzoyl chloride in the presence of different Lewis acids is reported. The exo and endo 1-acyl-6-methyl bicyclo [3.1.0]hexane isomers are formed with variable percentages depending upon the catalyst used. An unexpected compound, 3-benzoyl-2-methylcyclohexanol, was isolated from the reaction of 1-methylcyclohexene with benzoyl chloride. The acylation of 1,3,3,5,5-pentamethylcyclohexene with acetyl chloride – stannic chloride gave no bicyclic compounds.

Acylation of Aluminum Trisacetylacetonate with n-Butyryl Chloride in the Presence of Aluminum Chloride

Acylation of Aluminum Trisacetylacetonate with <i>n</i>-Butyryl Chloride in the Presence of Aluminum Chloride

Friedel–Crafts acylations of aromatic hydrocarbons. Part IX. Relative reactivities of acetyl, propionyl, butyryl, isobutyryl, valeryl, hexanoyl, decanoyl, benzoyl, and mesitoyl chlorides in the acylation of benzene and mesitylene

The relative reactivities in Friedel-Crafts acylations catalysed by aluminium chloride of the acyl chlorides given in the title are (i) with benzene, in ethylene dichloride solution, 1·00, 0·66, 0·54, 0·23, 0·49, 0·38, 0·38, 7·3 × 10–4, and 2·4 × 10–3, respectively; (ii) with benzene, in nitromethane solution, 1·00, 0·92, 0·78, 0·20, 0·64, 0·62, 0·55, 0·06, and 1·8 × 10–3, respectively; (iii) with mesitylene, in nitromethane solution, 1·00, 0·30, 0·27, 0·18, 0·45, 0·58, 0·67, 0·35, and 1·3 × 10–4, respectively.

Effects of Metal Chlorides on the Reaction of Acetylacetone with n-Butyryl Chloride

Effects of Metal Chlorides on the Reaction of Acetylacetone with <i>n</i>-Butyryl Chloride

Preparation and Rates of Hydrolysis of Perfluoro- Esters of Cellulose

Partial esters of cellulose varying in degree of substitution from 0.02 to 0.58 were prepared by reacting cellulose immersed in dimethylformamide with either perfluoro butyryl chloride or perfluorooctanoyl chloride in the presence of a tertiary aromatic amine. The use of essentially homogeneous solutions of acid chlorides resulted in prod ucts which retained properties of the original cotton and showed in addition oil and water repellency which was durable to dry cleanings and aqueous launderings in the presence of neutral detergents. Rates of uncatalyzed hydrolysis of the perfluorooctanoyl cellulose esters were determined at 25°, 35°, and 45° C., and the rate of the alkaline catalyzed hydrolysis was estimated at 25° C. The energy and entropy of activation for the uncatalyzed hydrolysis were determined.

Photochlorination of butyryl, valeryl and caproyl chloride

AbstractThe photochlorination at room temperature of butyryl, valeryl and caproyl chloride in the liquid phase has been investigated.The acid chlorides were allowed to interact with a third of the equimolecular amount of chlorine under irradiation with a mercury lamp. The reaction mixtures obtained were separated by fractional distillation and counter current distribution according to Craig.The monochloro‐derivatives of the acid chlorides were characterized by preparing the ρ‐toluidides. The identity of α‐, β‐, δ‐ and ϵ‐chlorocaproic acids was established by synthesis.It is found that butyryl chloride yields &lt;2% α‐, 50‐55% β‐ and 45‐50% γ‐chlorobutyryl chloride; valeryl chloride yields &lt;1.5% α‐, 15‐20% β‐, 50‐55% γ‐ and 30‐35% δ‐chlorovaleryl chloride, while caproyl chloride produces &lt; 1 % α‐, 5‐10% β‐, 25‐30% γ‐, 40‐45% δ‐and 20‐25% ϵ‐chlorocaproyl chloride.These results can be explained by reckoning with the fact that secondary hydrogen atoms are replaced more rapidly than primary and taking into account the deactivating effect of the carbonyl chloride group along the chain.

Acyl derivatives of 1-hydroxyalkylphosphonic esters

1. By the action of acetyl, butyryl, and isobutyryl chlorides on some 1-hydroxyalkylphosphonic esters having a hydrogen on the 1-carbon, the corresponding acyl derivatives of the esters were obtained. Some of their physical constants were determined. 2. It was shown that similar compounds can be prepared by reaction of aldehydes with esters of mixed anhydrides of phosphorous acid and various carboxylic acids.

The photochlorination of butyryl and valeryl chloride: (Preliminary communication)

AbstractSome preliminary experiments on the photochlorination of butyryl and valeryl chloride in the liquid and the vapour phase are described.The chlorination of butyryl chloride in the liquid phase yields about equal quantities of β‐ and γ‐chlorobutyryl chloride and only a small amount of the α‐chloro compound. In the gas phase somewhat more of the β‐chloro derivative is formed.In the chlorination of valeryl chloride, too, the substitution preferentially occurs in positions remote from the carbochloride group. This result differs considerably from that obtained by Bruylants and collaborators'). These authors report that in the gas phase, together with a small amount of the a‐chloro compound, only β‐ and γ‐chlorovaleryl chloride are formed, whereas we have found that the reaction mixture contains, in addition to the above‐mentioned substances, 25‐30% of δ‐chlorovaleryl chloride. Our results do not support the hypothesis of Bruylants c.s. that the course of the chlorination depends on a cyclic conformation of the acid halides.

Societies and Academies

Societies and Academies