By sulfuric acid

To a solution of 1.94 grams of crystalline cannabidiol in 35 cc. of cyclohexane (free from unsaturated material) was added one drop of 100% sulfuric acid. The mixture was refluxed for one hour, at the end of which time the alkaline Beam test was negative. The solution was decanted from the sulfuric acid, washed twice with aqueous 5% bicarbonate solution and twice with water, and evaporated. The residue was distilled under reduced pressure. Three fractions were collected, B. P. 165-170° (0.1 mm.),[a]29 D—259° to—269°. Rotation.—0.0381 gram made up to 5 cc. with acetone at 29° gave [a] D—210° 1, 1 [a]29 D—264°. 

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Sulfonic acids can come from the sulfonation of oil cuts from white oil production by sulfuric acid treatment. Sodium salts of alkylaromatic sulfonic acids are compounds whose aliphatic chains contain around 20 carbon atoms. The aromatic ring compounds are mixtures of benzene and naphthalene rings. 

Sulfated ash in lubricating oils in greases NF T 60-143 ISO 3987 ASTM D 874 NF T 60-144 ASTM D 128 Weight of residue after treatment of the ash by sulfuric acid and calcination As above... 

Production Technology. Processes for extraction of P2O3 from phosphate rock by sulfuric acid vary widely, but all produce a phosphoric acid—calcium sulfate slurry that requires soHds-Hquid separation (usually by filtration (qv)), countercurrent washing of the soHds to improve P2O3 recovery, and concentration of the acid. Volatilized fluorine compounds are scmbbed and calcium sulfate is disposed of in a variety of ways. 

Modem chrome-tanning methods are weU controUed and employ an extensive knowledge of the chemistry of the system. The most common chromium-tanning material used is basic chromium sulfate [12336-95-7] Cr(0H)S04, made by the reduction of sodium bichromate with sulfur dioxide or by sulfuric acid and a sugar. 

Manufacture and Processing. Until World War II, phthaUc acid and, later, phthaUc anhydride, were manufactured primarily by Hquid-phase oxidation of suitable feedstocks. The favored method was BASF s oxidation of naphthalene [91-20-3] by sulfuric acid ia the presence of mercury salts to form the anhydride. This process was patented ia 1896. During World War I, a process to make phthaUc anhydride by the oxidation of naphthalene ia the vapor phase over a vanadium and molybdenum oxide catalyst was developed ia the United States (5). Essentially the same process was developed iadependendy ia Germany, with U.S. patents being granted ia 1930 and 1934 (6,7). 

Reduction. Just as aromatic amine oxides are resistant to the foregoing decomposition reactions, they are more resistant than ahphatic amine oxides to reduction. Ahphatic amine oxides are readily reduced to tertiary amines by sulfurous acid at room temperature in contrast, few aromatic amine oxides can be reduced under these conditions. The ahphatic amine oxides can also be reduced by catalytic hydrogenation (27), with 2inc in acid, or with staimous chloride (28). For the aromatic amine oxides, catalytic hydrogenation with Raney nickel is a fairly general means of deoxygenation (29). Iron in acetic acid (30), phosphoms trichloride (31), and titanium trichloride (32) are also widely used systems for deoxygenation of aromatic amine oxides. 

Miscellaneous. Halogenation of the methyl group of dimethyl sulfate by chlorine and by fluorine has been described (64,65). Reduction of dimethyl sulfate by hydhodic acid occurs in a way that is comparable to that shown by sulfuric acid and results in reduction to sulfur (66). 

Although ilmenites and leucoxenes can be used in the chloride process, ores having higher Ti02 contents, eg, mineral mtile, which is not readily attacked by sulfuric acid, are preferred in order to minimise loss of chlorine in iron chloride by-product. 

Butyl Ether. -Butyl ether is prepared by dehydration of -butyl alcohol by sulfuric acid or by catalytic dehydration over ferric chloride, copper sulfate, siUca, or alumina at high temperatures. It is an important solvent for Grignard reagents and other reactions that require an anhydrous, inert medium. -Butyl ether is also an excellent extracting agent for use with aqueous systems owing to its very low water-solubiUty. 

Aryl-l,2-benzisoxazoles can also be prepared by the reaction of o-nitrobenzaldehydes and an aromatic hydrocarbon catalyzed by sulfuric acid (67AHC(8)277). Cyclization of (576) by Zn/HOAc gave (577) sulfuric acid cyclization gave (578) and (579) (62JOC3683, 66DIS(B)102). 

Note that the group on the left side of Eq. (14-182) is dimensionless. When turbulence promoters are used at the inlet-gas seclion, an improvement in gas mass-transfer coefficient for absorption of water vapor by sulfuric acid was obsei ved by Greenewalt [Ind. Eng. Chem., 18, 1291 (1926)]. A falhug off of the rate of mass transfer below that indicated in Eq. (14-182) was obsei ved by Cogan and Cogan (thesis, Massachusetts Institute of Technology, 1932) when a cauTiiug zone preceded the gas inlet in ammonia absorption (Fig. 14-76). 

Alkylations—for example, of olefins with aromatics or isoparaffins—are catalyzed by sulfuric acid, hydrofluoric acid, BF3 and AICI3. 

The failure was caused by sulfuric acid containing excessive water. Nearly pure sulfuric acid is only very mildly corrosive. However, when moisture content approaches 20% at 100°F (38°C), corrosion rates on 304... 

The weight of the superphosphate can be reduced by replacing sulfuric acid with phosphoric acid (obtained by sulfuric acid acting on phosphate rock followed by product separation, or by the... 

Eclazolast (41) is an antiallergy compound which inhibits release of mediators of allergy. One reported synthesis involves the simple e.ster exchange of methyl 2-benzoxazolecarboxylate (40) with 2-ethoxyethanol catalyzed by sulfuric acid [13]. 

Benzyl cyanide is first reacted with 2-butylbromide in the presence of sodium amide to give 2-phenyl-3-methylvaleronitrile which is hydrolyzed by sulfuric acid to give 3-methyl-2-phenyl-pentanoic acid. 24 g of 2-phenyl-3-methyl-pentanoic acid are heated for one hour at 175° to 185°C with 30 g of 2-diethylaminoethanol and 0.5 g of sodium methylate. The excess diethyl-aminoethanol is removed in vacuo, the residue is dissolved in 300 cc of 2 N-acetic acid, the acid solution is shaken with ether and made alkaline with concentrated potassium carbonate solution and ice. The ether solution Is washed with water, dried with sodium sulfate and evaporated. The residue is distilled under high vacuum, yielding 20 to 21 g of the basic ester (60% of the theoretical) is obtained, the ester boiling at 98° to 100°C at a pressure of 0.03 mm. The hydrochloride of the ester melts at 112° to 113°C and the methobromide at 100° to 101°C. 

Ammonia is one of the most important inorganic chemicals, exceeded only by sulfuric acid and lime. This colorless gas has an irritating odor, and is very soluble in water, forming a weakly basic solution. Ammonia could be easily liquefied under pressure (liquid ammonia), and it is an important refrigerant. Anhydrous ammonia is a fertilizer by direct application to the soil. Ammonia is obtained by the reaction of hydrogen and atmospheric nitrogen, the synthesis gas for ammonia. The 1994 U.S. ammonia production was approximately 40 billion pounds (sixth highest volume chemical). 

This approach explains the experimental fact that the complete decomposition of columbite or tantalite by sulfuric acid yields hydroxides of tantalum and niobium according to the first step of Equation (127). 

This ease with which we can control and vary the concentrations of H+(aq) and OH (aq) would be only a curiosity but for one fact. The ions H+(aq) and OH (aq) take part in many important reactions that occur in aqueous solution. Thus, if H+(aq) is a reactant or a product in a reaction, the variation of the concentration of hydrogen ion by a factor of 1012 can have an enormous effect. At equilibrium such a change causes reaction to occur, altering the concentrations of all of the other reactants and products until the equilibrium law relation again equals the equilibrium constant. Furthermore, there are many reactions for which either the hydrogen ion or the hydroxide ion is a catalyst. An example was discussed in Chapter 8, the catalysis of the decomposition of formic acid by sulfuric acid. Formic acid is reasonably stable until the hydrogen ion concentration is raised, then the rate of the decomposition reaction becomes very rapid. 

However, in most cases, relation (48) does not account for results obtained under experimental conditions used in industry, i.e. high reactant concentrations. Othmer carried out a detailed study in this field and suggested second-order reactions for the esterifications of n-butanol with acetic acid245 and monobutyl terephthalate246 catalyzed by sulfuric acid. Since such relations cannot be established in all cases, no reaction order could be found for the esterification of 2,3-butanediol with acetic arid247 in the presence of sulfuric add. Moreover, Othmer s reaction orders were obtained for very concentrated media and in our opinion cannot be connected to a mechanism. In fact, this was not Othmer s objective who established these relations for practical use in industrial esterifications. 

O2N)5C10H2.OH, mw 369.18, N 18.97%, OB to CO2 —45.51%. Prepn from naphthalene by action of nitric acid Hg nitrate followed by sulfuric acid... 

PET powder was prepared from commercial PET bottles and had a number-average molecular weight of 30,000. PET powder (0.2 g) was placed in 30 mL of relatively dilute sulfuric acid (10 M) in a sealed Pyrex tube and heated to 150°C for 1-6 h in an oven. After the reaction mixture was allowed to cool, the precipitate of TPA and PET residue deposited was filtered through a 1G-5 glass filter. TPA was separated as the ammonium salt by dissolving it in 12 mL of 5 M NH3. The TPA was reprecipitated by sulfuric acid solution. The yield of TPA was 100% in 10 M sulfuric acid solution. 

Fatty alcohols were sulfated with concentrated sulfuric acid before World War II, most frequently involving oleyl alcohols or alcohols derived from sperm and whale oil. Low temperatures were often suggested. Oleyl alcohol was sulfated by adding the alcohol to concentrated sulfuric acid, precooled to a temperature only slightly above the melting point of the alcohol [19], or by addition of cooled sulfuric acid (<95.12%) mixed with diethyl ether and phosphorus pentoxide to the alcohol, under constant stirring, for 3 h at 6-7°C, giving a yield of 98% [20]. Oleyl alcohol was also sulfated either by sulfuric acid or by oleum at 15°C [21]. 

Because Br and I are oxidized by sulfuric acid, phosphoric acid is used in the preparation of HBr and HI ... 

The sulfate process is based on the attack of activated beryl by sulfuric acid to form water-soluble Be and A1 sulfates and insoluble silica. A flow diagram summarizing this process is given in Scheme 1. Activated beryl must be used since the natural ore is resistant to acid attack except by HF, which is prohibitively expensive. High-grade beryl ore (> 10% BeO) is normally activated by a heat-treatment process... 

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