Ethanol denaturation

Some of the substances used to denature ethanol include methanol benzene pyri dine castor oil and gasoline... 

Value shown is for denatured ethanol. Neat ethanol blended at 10.0 vol % produces 3.7 wt % oxygen. 

Denatured Ethanol. Eor hundreds of years alcohoHc beverages have been taxed all over the world to generate government revenue. When ethanol emerged as a key industrial raw material, the alcohol tax was recognized as a burden to many essential manufacturing industries. To lift this burden, the Tax-Eree Industrial and Denatured Alcohol Act of 1906 was passed in the United States. The U.S. Treasury, Bureau of Alcohol, Tobacco, and Firearms (BATE), now oversees the production, procurement, and use of ethanol in the United States. 

The crude ketal from the Birch reduction is dissolved in a mixture of 700 ml ethyl acetate, 1260 ml absolute ethanol and 31.5 ml water. To this solution is added 198 ml of 0.01 Mp-toluenesulfonic acid in absolute ethanol. (Methanol cannot be substituted for the ethanol nor can denatured ethanol containing methanol be used. In the presence of methanol, the diethyl ketal forms the mixed methyl ethyl ketal at C-17 and this mixed ketal hydrolyzes at a much slower rate than does the diethyl ketal.) The mixture is stirred at room temperature under nitrogen for 10 min and 56 ml of 10% potassium bicarbonate solution is added to neutralize the toluenesulfonic acid. The organic solvents are removed in a rotary vacuum evaporator and water is added as the organic solvents distill. When all of the organic solvents have been distilled, the granular precipitate of 1,4-dihydroestrone 3- methyl ether is collected on a filter and washed well with cold water. The solid is sucked dry and is dissolved in 800 ml of methyl ethyl ketone. To this solution is added 1600 ml of 1 1 methanol-water mixture and the resulting mixture is cooled in an ice bath for 1 hr. The solid is collected, rinsed with cold methanol-water (1 1), air-dried, and finally dried in a vacuum oven at 60° yield, 71.5 g (81 % based on estrone methyl ether actually carried into the Birch reduction as the ketal) mp 139-141°, reported mp 141-141.5°. The material has an enol ether assay of 99%, a residual aromatics content of 0.6% and a 19-norandrost-5(10)-ene-3,17-dione content of 0.5% (from hydrolysis of the 3-enol ether). It contains less than 0.1 % of 17-ol and only a trace of ketal formed by addition of ethanol to the 3-enol ether. 

Reduction done in 3A Ethanol (a denatured ethanol) with 85% HjpO at 60 psig. 

Denatured ethanol, 592 Density The ratio of the mass of a substance to its volume, 14-15 measuring, 14-15 electron, in hydrogen atom, 165 lipoprotein, 603-604 measuring, 14-15 molar mass and, 109-111 Dexedrine, 601 Diabetes, 593... 

D. 4a(S),8a(R)-2-Benzoyloctahydro-6(2H)-isoquinolinone (4). Palladium (Pd), 10% on carbon, 4.0 g, (Note 21) is placed in a 500-mL Parr bottle under N2 and carefully wetted with 50 mL of cold denatured ethanol (EtOH). A slurry of 34.7 g of enone 3 (0.14 mol) in denatured EtOH (250 mL) is added and the Parr shaker apparatus assembled. After the system is purged with nitrogen-hydrogen (N2/H2), the reaction is shaken at 50 psi H2 and 50°C until H2 uptake is complete (1 hr, Note 22). The catalyst is filtered over a Celite pad (Note 23) and rinsed with warm chloroform (CHCI3) (4 x 75 mL). The filtrate is concentrated under reduced pressure, dissolved in 90 mL of CH2CI2 and crystallized with 200 mL of hexanes. The crystalline solid is filtered, rinsed with hexanes and dried to afford 34.3 g (98%, Note 24) of the ketone 4, representing a 51% yield over four steps. 

Place a mixture of 4 parts concentrated sulfuric acid and one part denatured ethanol in a flask containing enough clean, dry sand to form a thin paste. 

B destaining solution 10% acetic acid (v/v), 30% methanol or non-denaturated ethanol or isopropanol (v/v) in deionized water... 

A 0.2 g Coomassie Brilliant Blue R250 are dissolved in 40 ml methanol or non-denaturated ethanol then 10 ml glacial acetic acid are added and the solution is filled up to 100 ml with deionized water. Stable at RT B 0.05 g Bismarck Brown R are dissolved in 40 ml methanol or non-denaturated ethanol then 10 ml glacial acetic acid are added and the solution is filled up to 100 ml with deionized water. Stable at RT. 

When denatured ethanol is blended into gasoline at 10% by volume, the blend is identified as gasohol. Some of the important properties of gasohol compared to gasoline without 10% ethanol are included in TABLE 3-8. 

Alternative Fuel Includes methanol, denatured ethanol and other alcohols, separately or in mixtures of 85% by volume or more with gasoline or other fuels, CNG, LNG, LPG, hydrogen, coal derived liquid fuels, fuels other than alcohols derived from biological materials, electricity, neat biodiesel, or any other fuel determined to be substantially not petroleum and yielding substantial energy security benefits and substantial environmental benefits. It is defined pursuant to the EPACT (Energy Policy Act of 1992), alternative fuels. 

E10 (Gasohol) Ethanol/gasolinc mixture containing 10% denatured ethanol and 90% gasoline, by volume. 

E85 Ethanol/gasoline mixture containing 85% denatured ethanol and 15% gasoline, by volume. 

D-Dibenzoyltartaric acid (D-DBTA) (32.2 g, 90 mmol, 1.0 eq) is added to a hot solution of racemic 4-benzyl albuterol (29.6 g, 90 mmol, 1.0 eq) in 180 mL of anhydrous denatured ethanol (type 3A, denatured with 5 vol % 2-propanol). The resulting solution is refluxed for 15 min and cooled to room temperature over 40 min and seeded with 99% ee (R)-4-benzyl albuterol D-DBTA salt. The mixture is cooled to 5°-10°C and stirred for 1 hour. The white solid is collected by filtration and dried at 40°C and 28 inches of Hg for 1 hour to give (R)-4-benzyl albuterol D-DBTA salt (31.8 g, 50% yield, 83.6% ee). 

Place 35 kg of L-norvaline in approximately 300 kg of denatured ethanol in a reactor. Introduce approximately 60 kg of thionyl chloride, slowly and gradually. After stirring for a quarter of an hour, heat to reflux for 3 hours and... 

A 100 g portion of 3-methoxybenzenethiol and 39.1 g of potassium hydroxide dissolved in 300 ml of water were added to 750 ml of denatured ethanol, and the flask was put in a cooling bath. A total of 164 g of a-bromo-4-methoxyacetophenone was then added in small portions, and the mixture was stirred for 10 minutes in the cooling bath after the addition was complete and then for 3 hours at ambient temperature. The solvent was then evaporated off in vacuum, and 200 ml of water was added. The mixture was extracted with ethyl acetate, and the organic layer was washed twice with water, twice with aqueous sodium bicarbonate solution, and twice with aqueous sodium chloride solution. The organic layer was then dried over magnesium sulfate, filtered... 

Like methanol, ethanol is an excellent solvent of low toxicity that is cheap to produce. Unfortunately, the liquor tax makes ethanol relatively expensive. Use of untaxed ethanol is possible, but it requires extensive record keeping and purchase of a special license. Denatured alcohol is ethanol that contains impurities that make it undrinkable. Denatured ethanol is untaxed, but the impurities (methanol, methyl isobutyl ketone, aviation gasoline, etc.) also make it unsuitable for many laboratory uses. 

Free Acetic Acid Transfer 10.0 g of sample into a 250-mL glass-stoppered Erlenmeyer flask, dissolve in 75 mL of ethylene dichloride, add 60 mL of specially denatured ethanol formula 2B, and mix. Add phenolphthalein TS, and titrate with 0.02 N methanolic potassium hydroxide to a faint pink endpoint. Perform a blank determination (see General Provisions), and make any necessary correction. Each milliliter of 0.02 N methanolic potassium hydroxide is equivalent to 1.201 mg of C2H402. 

Note. Two other classes of methylated spirits are recognised in the United Kingdom mineralised methylated spirits and denatured ethanol. Mineralised methylated spirits is ethanol of an appropriate strength, 90 parts by volume mixed with wood naphtha 9.5 parts by volume and crude pyridine 0.5 parts by volume, and to every 2000 litres of this mixture is added 7.5 litres of mineral naphtha (petroleum oil) and 3.0 g of methyl violet. Denatured ethanol is ethanol, of a strength not less than 85% v/v, 98 parts by volume mixed with propanol 2 parts by volume, and to the resulting mixture is added denatonium benzoate 10 pg/ml, or solid quassin 120 pg/ml, or sucrose octa-acetate 4000 pg/ml. 

Note. The commercial substance known as wood naphtha , pyroxylic spirit or wood spirit contains 60 to 90% of methanol, together with acetone and other empyreumatic impurities. The variety used for denaturing ethanol (see under Ethanol) contains not less than 72% v/v of methanol. 

---