Ethanol: Production and Uses

Ethanol

• Also known as alcohol USP, grain alcohol, or ethyl alcohol
• Appears as a clear, colorless, mobile liquid
• Has a specific gravity of 0.7939 at 25°C
• Has a characteristic odor and burning taste
• It has a characteristic sweet odor and burning taste when consumed
• Boils at 78.9°C and freezes at -130°C
• Refers to ethyl alcohol unless otherwise specified
• Common name is ethyl alcohol, widely used as a solvent

Production of Ethanol

• Obtained from the fermentation of sugars
• Biochemical process: glucose is broken down into pyruvate, which then undergoes decarboxylation to release CO2, forming ethanol (C2H5OH) as the final product

Yeasts Involved in Fermentation

• Saccharomyces cerevisiae (baker's yeast) is used in bread-making and wine production; it facilitates dough rising by producing CO2
• Saccharomyces carlsbergensis (brewer's yeast) was originally used for beer production; it works efficiently at lower temperatures

Sources of Ethanol-Based Alcoholic Beverages

• Beer is made from grains like barley and malt.
• Wine is exclusively made from grapes
• Cider is typically made from apples or pears
• Mead is one of the oldest fermented drinks, made from honey
• Kilju is made from a saturated sugar solution
• Pulque is a traditional Mexican alcoholic beverage, utilizing honey water
• Rice wine (Tapuy) is made from sticky rice and is commonly found in Southeast Asia

Notes

• One standard drink per day is recommended (varies by health guidelines)
• Alcohol content in beverages is typically below 45% alcohol by volume (ABV)
• Alcoholism is characterized by alcohol dependence, where some individuals need alcohol to function daily

Phenol

• Known as carbolic acid, cresol, or hydroxybenzene (according to IUPAC)
• Classified as the simplest aromatic alcohol
• Appears as needle-like crystals with a pinkish tinge in its pure state
• Insoluble in water due to the benzene ring's influence on the hydroxyl (-OH) group
• Primary uses include disinfectant, sanitizer, and surface anesthetic
• Used as the standard for antimicrobial effectiveness

Phenol Coefficient

• It measures and compares the effectiveness of other disinfectants
• Determines the concentration of phenol required to effectively kill microorganisms
• Higher water solubility means better penetration into microorganisms, leading to increased antimicrobial effectiveness

Ethyl Acetate/Ethyl Ethanoate

• Also known as ethyl ester or acetidin
• Appears as a colorless liquid
• Has a fruity odor, similar to plastic balloons
• Easily volatilized and highly flammable
• Formed by esterification of ethanol (ethyl alcohol) and ethanoic acid (acetic acid)
• Dehydration reaction between these components results in ethyl acetate
• Carboxyl side (-COO-) takes priority in the molecular structure
• The presence of "-ate" in a compound's name indicates an ester or a salt

Acetone

• Also known as 2-propanone, propanone, or dimethyl ketone
• Colorless liquid with a characteristic fruity odor
• Boils at 56°C
• Simplest ketone and smallest molecule in the ketone family
• Common names are acetone and dimethyl ketone
• Related compound is 3-pentanone, a larger ketone

Acetone Uses & Regulations

• Common uses include nail polish remover and as an industrial solvent for paints, adhesives, and cleaning agents
• It is a regulated substance because it's used in the illegal synthesis of methamphetamine (shabu/methylpentamine)
• Not freely available; requires a PDEA license for large-scale storage or purchase

Formaldehyde General Properties

• Also known as methanal (IUPAC name), formalin, or formol
• Appears as a colorless gas with a characteristic pungent odor and a burning taste
• Condenses into a liquid at -20 degrees Celsius and solidifies at 90 degrees Celsius

Formaldehyde Chemical & Uses

• named formaldehyde ("-al") based on the aldehyde functional group
• Disinfectant that kills microorganisms
• Embalming fluid that preserves dead tissue
• Preservative for biological specimens by protein precipitation, which prevents decomposition
• As a gas, it can be used to sterilize an entire room

Historical Naming of Aldehydes

• Form- = "Ants" (formic acid originally derived from ant venom)
• Acet- = "vinegar" (acetic acid)
• Propion- = "Milk" (propionic acid)
• Butyr- = "Butter" (butyric acid)
• Valer- = "valerian root" (valeric acid)
• Capro-, Capryl-, Capr- = "Goat" (capric acid)
• Enanth- = "vine" (enanthic acid)
• Pelargon- = "herb" (pelargonic acid)
• Formalin is a solution of formaldehyde gas dissolved in water, producing a pungent odor and burning taste

Toluene

• Also known as methyl benzene
• Appears as a colorless liquid
• Has a paint thinner-like smell
• Boils at 100.6°C

Toluene Effects & Uses

• CNS effects: Exposure to toluene fumes can cause effects on the central nervous system (CNS), including dizziness and headaches
• Used in (paints, adhesives, and chemicals)
• Used in gasoline and explosives production

Methanol

• Also known as methyl alcohol or wood alcohol
• Appears as a colorless liquid with a specific gravity of 0.802
• Boils at 60°C and has a pungent odor and taste

Methanol Production & Sources

• "Wood Alcohol" was named because it was originally produced by destructive distillation of wood
• Also a contaminant in alcohol production
• Found in homemade alcoholic beverages like lambanog
• Methanol poisoning incidents occur due to contamination in illegally or poorly distilled liquors

Methanol Toxicity & Effects

• Highly poisonous
• Metabolism in humans: broken down by alcohol dehydrogenase (ADH) into formaldehyde, which is further converted into formic acid and is a natural irritant and is highly toxic
• Optic nerve & retinal damage and severe toxicity can be fatal
• Ethanol byproducts are less toxic than methanol byproducts

Ethanol Vs. Methanol

• Acetaldehyde can cause hangovers, while formic acid (from methanol) causes severe toxicity

Methanol: Uses & Regulation

• Industrial uses include use in aniline dye production
• Denatured alcohol, used to make it unfit for drinking is sold to consumers

Methanol Poisoning Management

• Disulfiram inhibits aldehyde dehydrogenase, leading to an accumulation of acetaldehyde
• It is used for the treatment of alcoholism to deter alcohol consumption by causing severe hangover effects

Diethyl Ether

• Known as ethoxy ethane, or ether
• A component of starting fluids and a solvent in synthetic dye and plastics manufacture
• Used as the prototype anesthetic until replaced in the 1960's
• CNS effects are attributed to interactions with neuronal membranes and ion channels

Diethyl Ether - Mechanism & Uses

• Mechanism of action: interacts with neuronal membranes and ion channels in the CNS
• Reduces ion movement in axons, delaying electrical impulses and leading to loss of sensation
• Industrial uses: component of starting fluids (used for engines in cold conditions) and solvent in synthetic dye and plastic production

Salicylic Acid

• 2-hydroxybenzoic acid, or o-hydroxybenzoic acid
• Long white needle-like crystal with a sweet, acidulous taste
• Keratolytic
• From bark of Salix purpurea, Family SALICACEA
• Slightly soluble in water, highly soluble in alcohol and ether

Salicylic Acid - Uses & Applications

• Keratolytic Agent: Used in skincare to exfoliate dead skin cells and treat acne, warts, and psoriasis
• Pharmaceutical Use: Precursor of acetylsalicylic acid (Aspirin) with Anti-inflammatory and analgesic properties

Benzoic Acid

• Benzene carboxylic acid, flowers of benzoin
• White crystalline flakes.
• Melting point of 122 degrees Celsius
• Name derived from gum benzoin
• Precursor for synthesis of many organic substances.

Benzoic Acid: Sources, Properties, and Uses

• Source: Derived from Gum Benzoin (Styrax benzoin resin), simplest aromatic carboxylic acid (contains a benzene ring with a carboxyl (-COOH) functional group)
• Uses & Applications:
  • Precursor for organic synthesis
  • Used for:
    • dDyes, perfumes, and food preservatives.
• Solubility & Chemical Properties
  • Weakly acidic, reacts with sodium bicarbonate (NaHCO3) but is less alkaline than NaOH
  • Not soluble in all solvents and is likely non-polar

Benzoic Acid Other Names

• Carboxybenzene, dracylic acid, benzenemethanoic acid, benzeneformic acid
• Flowers of Benjamin/Benzoin, phenylcarboxylic acid, phenylformnic acid benzoate = other names
• Simplest aromatic carboxylic acid
• Slightly soluble in cold water; soluble in hot water / Weakly acidic aqua solution

Test Using Ferric Chloride

• If Phenol, violet colour after test If Benzoic Acid, buff colored after test

Benzoic Acid With Sulfuric Acid

• White precipitate
• product is: 3-Carboxybenzenesulphonic acid

With NAOH

• Carboxylate Salt + Phenolate Salt (More soluble in water)

IDENTIFICATION TEST

• Toluene & Ethyl Acetate

GENERAL CHARACTERISTICS OF ORGANIC COMPOUNDS

• Don't dissolve in water/polar solvents
  • Van der Waals Forces: organic compounds are immiscible in polar solvents due to similar spatial distribution and the tendency of like molecules to bind together.

- Dissolve in organic/non-polar solvents - Due to nature and interactions - Maximum catenation and tetravalency of carbon.

• Formation of long open and closed chain compounds through covalent bonds. Volatile, inflammable, low BP & MP. Due inter-molecular forces interactions. Some polymerisation: Ex plastic proteins and fibers

-Isomerism - Compounds w similar molecular formula but differ- Non-conductors of electricity. - Absence prevents electrical

COMMON IMPURITIES

• Side Products/Catalysis
• Excesive staring reagnets
• Must be isolated from the reactions
• Purified for iseor identifation

METHODS OF PURIFICATION OF SOLID PRODUCTS: CRYSTALIZATION

• A mixture solids used ifying solvent, material has at the rate is low at tempratures for highly solids and readlily form

Methods for Solid Products Purification: Recrystallization

• Dissolve in minimum amount of solvenrt, Filtering the hot solution and letting it cool until crystilized and filteted of solvent.
• Compound cold or should beinsoluble at room temperature
• Should be a minimal of solvent to make concentrated for similarity.

METHODS Fractional Crystalization/Products Sublimation.

• The solubility of the product need one another Series of repeat to related compounds.
• Method: in substances passes when heated, such as naphthalene or camphor. For/non-volatile

METHODS OF PUR STEAM

Requirements for impure compounds: - Must not decompose at a steam temperature - Fairly high vapor pressure at 373K - Insoluble in water

SYNTHESIS FORMULA

• Shows the reaction between C7H8+6KMno4+ 18HC1 = 5C7H502+ 6MNCL2+&KCI+

TEST

• TOLUNE With Bromine with Fering and ethyl acitate