Aluminum chloride catalyst preparation

Isopropylnaphthalenes can be prepared readily by the catalytic alkylation of naphthalene with propjiene. 2-lsopropylnaphthalene [2027-17-0] is an important intermediate used in the manufacture of 2-naphthol (see Naphthalenederivatives). The alkylation of naphthalene with propjiene, preferably in an inert solvent at 40—100°C with an aluminum chloride, hydrogen fluoride, or boron trifluoride—phosphoric acid catalyst, gives 90—95% wt % 2-isopropylnaphthalene however, a considerable amount of polyalkylate also is produced. Preferably, the propylation of naphthalene is carried out in the vapor phase in a continuous manner, over a phosphoric acid on kieselguhr catalyst under pressure at ca 220—250°C. The alkylate, which is low in di- and polyisopropylnaphthalenes, then is isomerized by recycling over the same catalyst at 240°C or by using aluminum chloride catalyst at 80°C. After distillation, a product containing >90 wt % 2-isopropylnaphthalene is obtained (47). 

To prepare multifunctionalized symmetric organosilicon compounds by the polyalkylation of benzene. (2-chloroethyi)trichlorosilane and (3-chloropropyl)tri-chlorosilane were reacted with benzene. Polyalkylations of benzene with (2-chloroethyl)silane and (3-chloropropyl)silane were carried out in the presence of aluminum chloride catalyst at a reaction temperature of 80 C. The reaction of benzene with excess (2-chloroethyI )trichlorosilanes afforded pcralkylated product, hexakis(2-(trichlorosilyl)ethyl)benzene in good yield (70%). ... 

Trimethylsilyl)benzophenone cyanohydrin has been prepared previously by the addition of trimethylsilyl cyanide to benzophenone using an aluminum chloride catalyst.4 The preparation of cyanohydrin silyl ethers described in the synthesis is based on... 

The aluminum chloride catalyst for the alkylation process may be purchased material or the aluminum chloride may be prepared in situ. For large plants preparation in situ from cheap powdered aluminum and anhydrous HCl js preferred however, ethyl chloride is just as effective as HCl although more expensive. A small supplementary agitated vessel is used to... 

Studies on the conditions of the reaction have been made using simple compounds as model substances, A comparison of thirty-nine metallic chlorides shows aluminum chloride to be the most effective in the preparation of p-methylacetophenone. Optimum yields result when the molar ratios of aluminum chloride to anhydride, acyl chloride, and acid are 3.3, 1,0, and 2.5, respectively. Halogen and oxyhalogen carriers are not helpful. Inconsistent yields in the Friedel-Crafts reaction have been attributed to the presence of ferric chloride or moisture in the aluminum chloride Catalyst. Prolonged heating causes condensation of the ketone product. 

Catalyst or with acetyl chloride and aluminum chloride catalyst have been reported. o-Nitrophenyl 2-thienyl ketone has been prepared. ... 

Besides the already mentioned acidic aluminum chloride catalysts, alternative Friedd-Crafts catalysts such as supported acidic tin catalysts have also been developed. The tin-based catalysts were prepared by a method which closely resembled the already mentioned two-step grafting method devised for the aluminum chloride catalyst. Here, SnCU was anchored on silica materials modified with tetraalkylammonium chloride moieties obtained for example, from reaction with [3-(trimethoxysrlyl)propyl]octadecyldimethylammonium chloride, thereafter, reaction of the Lewis acid with the chloride moieties leads to formation of pentacoordinated anionic tin species forming catalytically active complexes (i.e. [R4N][SnCl5] species), associated with the surface. The supported tin catalysts were employed for condensation reactions of olefins with aldehydes forming unsaturated alcohols (Prins condensation. Scheme 5.6-2) [76]. 

Write a stepwise mechanism for the preparation of diphenylmethane by treating benzene with dichlo-romethane in the presence of an aluminum chloride catalyst. (See Example 9.4)... 

Poly[isobutylene-co-isoprene] or butyl rubber was synthesized in 1937 at the Standard Oil Development Co., forerunner of ExxonMobil Chemical Co. (2). The first sulfur-curable copolymer was prepared in ethyl chloride over an aluminum chloride catalyst with 1,3-butadiene as the comonomer however, it was soon found that isoprene was a better comonomer and that methyl chloride was a better polymerization diluent. During World War II, the natural rubber supply to the United States was drastically curtailed, boosting the production of synthetic rubber. The commercial production of butyl rubber in 1943 was an enormous scientific and engineering achievement given the very early state of the art and complexity of this technology. 

L Preparation of Poly (vinyl ethyl ether) Using Aluminum Chloride Catalyst. 241... 

Aldehyde Synthesis. Formylation would be expected to take place when formyl chloride or formic anhydride reacts with an aromatic compound ia the presence of aluminum chloride or other Friedel-Crafts catalysts. However, the acid chloride and anhydride of formic acid are both too unstable to be of preparative iaterest. 

Friedel-Crafts Acylation. The Friedel-Crafts acylation procedure is the most important method for preparing aromatic ketones and thein derivatives. Acetyl chloride (acetic anhydride) reacts with benzene ia the presence of aluminum chloride or acid catalysts to produce acetophenone [98-86-2], CgHgO (1-phenylethanone). Benzene can also be condensed with dicarboxyHc acid anhydrides to yield benzoyl derivatives of carboxyHc acids. These benzoyl derivatives are often used for constmcting polycycHc molecules (Haworth reaction). For example, benzene reacts with succinic anhydride ia the presence of aluminum chloride to produce P-benzoylpropionic acid [2051-95-8] which is converted iato a-tetralone [529-34-0] (30). 

At 225—275°C, bromination of the vapor yields bromochloromethanes CCl Br, CCl2Br2, and CClBr. Chloroform reacts with aluminum bromide to form bromoform, CHBr. Chloroform cannot be direcdy fluorinated with elementary flourine fluoroform, CHF, is produced from chloroform by reaction with hydrogen fluoride in the presence of a metallic fluoride catalyst (8). It is also a coproduct of monochlorodifluoromethane from the HF—CHCl reaction over antimony chlorofluoride. Iodine gives a characteristic purple solution in chloroform but does not react even at the boiling point. Iodoform, CHI, may be produced from chloroform by reaction with ethyl iodide in the presence of aluminum chloride however, this is not the route normally used for its preparation. 

Tetrachloroethane is often an incidental by-product in the manufacture of chlorinated ethanes. It can be prepared by heating the 1,1,2,2-isomer with anhydrous aluminum chloride or chlorination of 1,1-dichloroethylene at 40°C (118). Hydrochlorination of trichloroethylene using a FeCl catalyst may also be used. 

Diphenylmethane has been prepared with aluminum chloride as a catalyst from methylene chloride and benzene, from chloroform and benzene as a by-product in the preparation of triphenylmethane, and from benzyl chloride and benzene. It has been prepared by the reduction of benzophenone with hydriodic acid and phosphorus, or with sodium and alcohol. It has also been made by heating a solution of benzyl chloride in benzene with zinc dust, or with zinc chloride. The above method is only a slight modification of the original method of Hirst and Cohen. ... 

An efficient catalyst for thermal isomenzations of halofluorocarbons [6, 7, 8, 9] IS prepared by treatment of alumina with dichlorodifluoromethane at 200-300 °C [9] or aluminum chloride with chlorofluorocarbons in the presence of metals [W] or palladium on alumina [II These catalysts are far more efficient than aluminum halides themselves (equations 1 and 2)... 

Acctothicnone has been prepared by treating thiophene with acetyl chloride in the presence of aluminum chloride1 or stannic chloride,2 and by treating 2-chloromercurithiophene with acetyl chloride.3 The present method is essentially that of Stadnikoff and Goldfarb.2 Stannic chloride is superior to aluminum chloride as a catalyst for this reaction as the latter induces polymerization of the thiophene. 

The first compounds of this class46 have been obtained via Route A. The initial condensation of phthalic anhydride with dimethylaniline requires a Friedel-Crafts catalyst, while condensation of the resulting benzophenone with the indole requires acetic anhydride. For Route B preparation of the intermediate l,2-dimethyl-3-(2-carboxybenzoyl)indole has also been described47 by condensation of the two components in the presence of aluminum chloride. However, in our experience, aluminum chloride is, in this case, unnecessary, thus rendering this route the method of choice. 

The parent hexathiaadamantane (185) is obtained preparatively when a solution of formic acid and hydrochloric acid in nitrobenzene is allowed to stand for several weeks in a hydrogen sulfide atmosphere the product which separated is almost insoluble in all common solvents and purification presents a problem. Only large volumes of dimethyl sulfoxide at reflux serve for recrystallization.224 The reaction of thioacetic acid with formic acid in the presence of zinc chloride gives tetramethyl-(186), monomethyl-, dimethyl-and trimethylhexathiaadamantane derivatives (187).225 Other variations include the reaction of thioacetic acid with a /i-diketone,226 and the use of boron trifluoride227 or aluminum chloride as a catalyst.228... 

Other Methods of Preparation.—Ethyl 2-(D-ara6i no-tetrahydroxybutyl)-5-methyl-4-furoate has been prepared by heating D-glucose plus ethyl acetoacetate in aqueous alcohol without a catalyst,1 or from the same reagents (1 g. and 0.5 ml., respectively) in 0.5 ml. of 96% ethanol plus 1.5 ml. of water at room temperature in the presence of ferric chloride, zinc chloride (with small quantities of hydrochloric acid or of sodium hydroxide), cupric chloride, ferric sulfate, zinc sulfate, aluminum chloride, nickel chloride, or cobalt nitrate.18... 

For the preparation of aryl esters from phosphorus oxychloride, a Lewis acid is generally added as a catalyst. Commonly, aluminum chloride with an excess of phosphorus oxychloride added to the phenol provides excellent yields (Equation 4.2).4... 

A similar type of catalyst including a supported noble metal for regeneration was described extensively in a series of patents assigned to UOP (209-214). The catalysts were prepared by the sublimation of metal halides, especially aluminum chloride and boron trifluoride, onto an alumina carrier modified with alkali or rare earth-alkali metal ions. The noble metal was preferably deposited in an eggshell concentration profile. An earlier patent assigned to Texaco (215) describes the use of chlorinated alumina in the isobutane alkylation with higher alkenes, especially hexenes. TMPs were supposed to form via self-alkylation. Fluorinated alumina and silica samples were also tested in isobutane alkylation,... 

Allylmagnesium bromide, 41, 49 reaction with acrolein, 41,49 5-AUyl-l,2,3,4,5-pentachlorocydopen-tadiene, 43, 92 Allyltriphenyltin, 41, 31 reaction with phenyllithium, 41, 30 Aluminum chloride, as catalyst, for isomerization, 42, 9 for nuclear bromination and chlorination of aromatic aldehydes and ketones, 40,9 as Friedel-Crafts catalyst, 41, 1 in preparation of mesitoic acid, 44, 70 in preparation of 2u-thiohomo-phthalimide, 44, 91... 

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