Boron chloride phosphoric acid

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). 

Note that ethylbenzene is a derivative of two basic organic chemicals, ethylene and benzene. A vapor-phase method with boron trifluoride, phosphoric acid, or alumina-silica as catalysts has given away to a liquid-phase reaction with aluminum chloride at 90°C and atmospheric pressure. A new Mobil-Badger zeolite catalyst at 420°C and 175-300 psi in the gas phase may be the method of choice for future plants to avoid corrosion problems. The mechanism of the reaction involves complexation of the... 

Aromatic amines form addition compounds and complexes with many inorganic substances, such as ziac chloride, copper chloride, uranium tetrachloride, or boron trifluoride. Various metals react with the amino group to form metal anilides and hydrochloric, sulfuric, or phosphoric acid salts of aniline are important intermediates in the dye industry. 

Nakagome and co-workers effected the successful cyclization of N-ethyl-N-arylaminomethylenemalonates (749) in poly phosphoric acid, prepared from orthophosphoric acid and phosphorus pentoxide in polyphosphate ester (PPE), prepared from phosphorus pentoxide and anhydrous diethyl ether in chloroform in phosphoryl chloride on the action of boron trifluoride etherate on the action of acetic anhydride and concentrated sulfuric acid or on the action of phosphorus pentoxide in benzene [71GEP2033971, 71JHC357 76JAP(K) 18440]. Depending on the work-up process, l-ethyl-4-oxoquinoline-3-carboxylates (750, R1 = Et), l-ethyl-4-oxoquinoline-3-carboxylic acids (750, R2 = H) and 3-ethoxycarbonyl-4-chloroquinolinium iodides (751) were obtained. Only the cyclization of... 

Several catalysts have been recommended for the N-acetylation of carbazole with acetic anhydride boron trifluoride, phosphorus pentoxide, concentrated sulfuric acid, zinc chloride, and phosphoric acid all gave 9-acetylcarbazole in moderate to good yield. 9-Acetylcarbazole can also be prepared using the Vilsmeier complex of N,N-dimethylacetamide and phosgene. ... 

The exceedingly high reactivity of ferrocene to Friedel-Crafts acylation is exemplified by the fact that mild catalysts such as stannic chloride (63), boron trifluoride (32), zinc chloride (86), and phosphoric acid (29), can be used with considerable success. When ferrocene and anisole were allowed to compete for limited amounts of acetyl chloride and aluminum chloride, acetylferrocene was the sole product isolated, again illustrating the high reactivity of ferrocene toward electrophilic reagents (6). 

Substances that are ordinarily deliquescent are sulfuric add (concentrated), glycerol, calcium chloride crystals, sodium hydroxide (solid), and 100% ethyl alcohol. In an enclosed space, these substances deplete the water vapor present to a definite degree. Other substances are used to accomplish this end by chemical reaction, e.g.. phosphorus pentoxide (forming phosphoric acid), and boron trioxide (forming boric acid). Water is absorbed from nonmiscible liquids by addition of such substances as anhydrous sodium sulfate, potassium carbonate, anhydrous calcium chloride. and solid sodium hydroxide. The converse phenomenon is known as efflorescence. 

E. D. Chattaway and H. P. Stevens found that phosphoric acid decomposes nitrogen iodide, producing ammonia. According to A. Geuther, when phosphoric acid is treated with phosphorus pentachloride at ordinary temp., phosphoryl chloride and hydrogen chloride are formed phosphorus trichloride furnishes meta-phosphoric and phosphorous acids and phosphoryl chloride is without action in the cold, but when hot, metaphosphoric acid is formed if the phosphoryl chloride be in excess, and phosphorous acid if only a little be present. G. Meyer, and A. Vogel prepared a complex with boric oxide or boric acid—vide boron phosphate, 5. 32, 27. 

Important aviation and motor alkylate gasoline processes are the jet-type sulfuric acid process, the Kellogg sulfuric acid autoref rigeration process, the UOP hydrofluoric acid process, and the Stratford effluent refrigeration process. Petrochemical alkylation includes various processes using as catalysts solid phosphoric acid, aluminum chloride, hydrofluoric acid, boron trifluoride, and phenol and ether complexes of boron trifluoride (1). 

Other workers also report studies on alkylation of aromatics over silica-alumina (63). Ivanov el al. alkylated coal-tar aromatics with olefins in the presence of aluminum chloride-hydrogen chloride and obtained a product suitable for use as a lubricating oil (143). Topchiev and Paushkin have reported high yields in the alkylation of isopentene with propylene in the presence of a catalyst containing phosphoric acid and boron trifluoride (395). 

Catalyst, alumina, 34, 79, 35, 73 ammonium acetate, 31, 25, 27 boron tnfluonde etherate, 38, 26 copper chromite, 31, 32, 36, 12 cupric acetate monohydrate, 38, 14 cuprous oxide silver oxide, 36, 36, 37 ferric nitrate, hydrated, 31, 53 phosphoric acid, 38, 25 piperidine, 31, 35 piperidine acetate, 31, 57 Raney nickel, 36, 21, 38, 22 sulfuric acid, 34, 26 Catechol, 33, 74 Cetylmalonic acid, 34, 16 Cetylmalonic ester, 34,13 Chlorination, by sulfuryl chloride, 33, 45, 37, 8... 

Both acid and base catalysis have been used extensively to catalyze exchange in aromatic, and to a lesser extent, heterocyclic molecules. In acid exchange, the most widely used catalysts are sulfuric acid,122,129, 131 phosphoric acid,132 trifluoroacetic acid5133 perchloric acid,134 aluminum chloride,135 and the phosphoric acid-boron trifluoride complex.132 These reactions constitute the simplest electrophilic substitution. The mechanism for such substitution in benzenoid compounds is now comparatively well understood 122 however, the problem of heteroaromatic electrophilic substitution is still being clarified and has led to renewed interest in acid-catalyzed exchange in heterocyclic compounds.122... 

ACIDS, INORGANIC Boric acid. Chloro-Iridic acid. Hydrobtomic acid. Hydrochloric acid. Hydrogen bromide. Hydrogen chloride. Hydrogen fluoride. Hydrogen fluoride-Boron trifluoride. ion-exchange resins. Nitric acid. Periodic acid. Phosphoric acid. Folyphosphoric acid. Sulfuric acid. 

The usefulness of catalysts other than aluminum chloride, e.g., anhydrous hydrogen fluoride 202, 223), boron trifluoride 100), and phosphoric acid 94), has been examined. The mercuration reaction which is characteristic of aromatic systems takes place also for ferrocene, as has been described by Nesmeyanov and his co-workers 143,147) Through the mercury compounds these workers have also obtained the halogeno-ferrocenes. 

Effective catalysts for preparing the polyformals were p-toluenesulfonic acid, camphorsulfonic acid, methanedisulfonic acid, and perchloric acid. Various other acidic compounds were evaluated as catalysts with tetramethylcyclobutanediol. In these experiments, 0.5 to 1.0 gram of acidic compound per mole of tetramethylcyclobutanediol was normally added. If insufficient water was obtained, more catalyst was added. If the prepolymer was obtained but an appreciable amount of brown color was present, less catalyst was then used. Compounds which did not catalyze the reaction (no water obtained) were phosphoric acid, zinc chloride, trifluoroacetic acid, and heptafluorobutyric acid. Incomplete reactions (insufficient water) took place with concentrated hydrochloric acid, concentrated nitric acid, zinc fluoroborate, or Amberlite IRC-50 ion exchange resin as catalyst. A prepolymer was obtained when boron trifluoride etherate was used, but buildup did not take place in the solid phase (catalyst probably too volatile). Brown or speckled-brown polymers (after solid-phase buildup) were obtained with catalysts containing sulfonic acid groups (benzenesulfonic, dodecylbenzenesulfonic, sulfo-acetic, methanetrisulfonic, sulfuric, p-toluenesulfonic, camphorsulfonic, and methanedisulfonic acids). To obtain white polymers from tetramethylcyclobutanediol it was necessary to treat the solvent and prepolymer reaction mixture as previously described. (White polyformals were obtained from the other diols without this treatment.)... 

Preferably the reaction in accordance with the invention is performed in the presence of a suitable catalyst, proton acids such as for instance haloid acids, sulfuric acid, phosphoric acid, perchloric acid, organic sulfonic acids, such as for instance methanesulfonic acid and p-toluenesulfonic acid, carboxylic acids, such as for instance oxalic acid, trifluoroacetic acid and other Lewis acids, such for instance boron trifluoride, ferric chloride, zinc chloride, zinc bromide, stannic chloride, titanium chloride or iodine having proved to be suitable. Furthermore mixtures of the individual catalysts may be used in certain cases. 

Rast molecular wEiom- determination Isoquinuclidone (set Dowtherm.) Rearranoements Beckmann p-Acetamldobanzanasuironyl chloride. Boron trifluoride. Formic acid (see Hypochloroua acid). Iodine pentafluoride. Phosphoryl chloride. Poly-phosphoric acid. p-Toluenesulfonyl chtorlda. Trlfluoroacetlc anhydride. 

Esterification Alumina. Boron trifluoride. Diazomethane. Dimethylformamide dimethyl acetal. Dimethylformamide dineopentyl acetal. Dimethyl sulfite. Diphenyidiazomethane. Ethyldicyclohexylamine. Ion-exchange resins. Isobutene. Methanesulfonic anhydride. 3 % Methanolic HCl (see Acetyl chloride). Methyl iodide. l-Methyl-3-p-tolyltriazine. Poly-phosphoric acid. Sulfosalicylic acid. Sulfuryl chloride. p-Toluenesulfonic acid. p-Tpluene-sulfonyl chloride. Triethylamine. Triethylorthoformate. Trifluoroacetic anhydride. Esterification of phosphoric acid Trichloroacetonitrile. 

However, this can now be overcome through the use of a cool-on-line injector and programming of the oven after sample injection (P. Teal, personal comm.). Cyclization of JH III to mono- and bicyclic products also occurs readily in the presence of boron trifluoride or phosphoric acid (H3PO4) [34]. Transition metals may catalyze similar reactions in aqueous solutions [12]. Inorganic salts, such as ferric chloride and zinc and magnesium sulfate, react with JH I, producing undetermined products [35]. The methyl ester function on C-l of JH III is resistant to saponification by strong base [14]. 

A variety of catalysts have been examined, comprising protonated acids inciuding phosphoric acid on Fuller s earth, sulphuric acid on the same support, and cation exchange materials. Lewis acids such as aluminium chloride, boron trifiuoride and its etherates, zinc chioride, siiica/aiumina, toluene-4-sulphonic acid and montmorillonite clays have found some application in numerous studies although generally the phosphoric acid system appears to be most favoured. 

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