ORGANIC SOLVENTS

DEFINE VOLATILITY

THE EASE WITH A SUBSTANCE VAPORISES, OR BECOMES A GAS. IT IS A PHYSICAL PROPERTY. DEPENDS ON THE TEMPERATURE, PRESSURE AND INTERMOLECULAR FORCES OF THE PARTICLES

PROPERTIES OF ORGANIC SOLVENTS

LIQUID AT ROOM TEMPERATURE

VOLATILE

FLAMMABLE AND EXPLOSIVE

NON-REACTIVE

Methanol

Wood alcohol

Blindness

Formaldehyde and formic metabolites formed, snowstorm blindness

Metabolic acidosis, delayed

USES

PAINT, DEGREASES, FUELS, GLUES, DRY CLEANING

Styrene

Hearing loss

Color vision affected

Acute and chronic CNS effects

Irritant dermatitis

IARC 2A

ROUTES OF EXPOSURE

INHALATION

SKIN ABSORPTION

INGESTION

WHAT IS THE RELATIONSHIP BETWEEN THE CARBON ATOMS AND ALIPHATIC HYDROCARBONS

NUMBER OF CARBON ATOMS!!!

• GAS VS LIQUID VS SOLID : 4 ATOMS OR LESS IS A GAS

• EFFECTS OF EXPOSURE

  • METHANE: SIMPLE ASPHYIANT —> CNS DEPRESSANTS

  • N-HEXANE

  • NITROPROPANE - HEPATOXIC/LIVER FAILURE

METHANE

Asphyxiant

ALIPHATIC COMPOUNDS (ALKANES,ALKENES,ALKYNES)

CARBON ATOMS ARE ARRANGED IN CHAINS (STRAIGHT OR BRANCHED) OR NON AROMATIC RINGS

SINGLE BOND= SATURATED = ALKANE E.G. METHANE- SIMPLEST

DOUBLE OR TRIPLE BONDS ARE UNSATURATED

1 DOUBLE - ALKENE

1 TRIPLE - ALKYNE

C-C-C-C- / C=C

ALIPHATIC HYDROCARBON

CYCLIC HYDROCARBONS

THE RINGS!!

MONO- CYCLIC OR POLYCYCLIC

RINGS! - SATURATED OR UNSATURATED WITH ATLEAST 3 CARBON ATOMS

WHAT A COMMON SOURCES OF CYCLIC HYDROCARBONS

PETROLEUM INDUSTRY

OIL!

THINK PETROL, PARAFFIN, KEROSENE - COMBINATIONS OF ALIPHATIC AND CYCLIC HYDROCARBONS

What group does Benzene, toulene and xylene belong to

Aromatic hydrocarbons

AROMATIC HYDROCARBONS (BENZENE RING STRUCTURE)

PLEASANT SMELL

BENZENE RING OR PHENYL RING(E.G. POLYPHENYL)

CNS DEPRESSANTS AND SKIN IRRITANTS

WHAT ARE AROMATIC HYDROCARBONS KNOWN FOR

CNS DEPRESSANT EFFECT

SKIN IRRITATION

HALOGENATED HYDROCARBONS ARE DANGEROUS

CARCINOGENIC ESP CHLORINE AND BROMINE CONTAINING ONES

IN TERMS OF TOXICITY, HOW WOULD YOU RANK HALOGENATED HYDROCARBONS

FLOURINE - LEAST TOXIC

BROMINE AND IODINE MORE TOXIC THAN CHLORINE CONTAINING HYDROCARBONS

NAME TWO IMPORTANT SOURCES OF HALOGENATED HYDROCARBONS

INSECTICIDES AND FUMIGANTS

DEGREASES

LIST THREE HALOGENATED HYDROCARBONS THAT ARE CARCINGENIC

CARBON TETRACHLORIDE

CHLOROFORM

TRI OR TETRACHLOROETHYLENE

EXAMPLES OF KETONES

ACETONE

MBK

MEK

GIVE AN EXAMPLE OF SYNERGISTIC EFFECTS FOR KETONES

MEK ON ITS OWN - NO PERIPHERAL NEUROPATHY

MEK + MBK => PERIPHERAL NEUROPATHY

WHAT ARE SOME ADVANTAGES OF KETONES

EXCELLENT SOLVENTS

LOW TOXICITY

NAME ON DANGEROUS ALDEHYDE

FORMALDEHYDE!! CARCINOGENIC TO MAN

HYDRCARBON+CARBONYL (C=O)

ALDEHYDE

HYDROCARBON+ OH

ALCOHOL

TWO EXAMPLES OF ALCOHOLS

METHANOL

ETHANOL

HEALTH EFFECT OF ALCOHOLS

NARCOSIS - WORSE WITH HIGHER MOLECULAR WEIGHT

ORGANIC HYDROCARBON USED IN ANTI FREEZE

GLYCOLS- THEY HAVE A HIGH BOILING POINT AND LOW FREEZING POINT

GLYCOLS ARE MAINLY A RISK IF INGESTED RATHER THAN INHALED

TRUE

HYDROCARBON+HYDROCARBON+0XYGEN

ETHER

IF CYCLIC THAN EPOXY COMPOUND

NAME ONE ETHER THATS CARCONOGENIC

EPICLHORHYDRIN

BENZENE RING + HYDROXYL GROUP

CRESOLS OR PHENOLS

WHAT ARE PHENOLS(CARBOLIC ACID)AND CRESOLS KNOWN FOR

HIGHLY CORROSIVE TO ALL TISSUES

Used as disinfectants

2 hydrocarbons plus Carbonyl group

Ketones

IARC 1 CANCER FOR FORMALDEHYDE

NASOPHARYNGEAL CANCER

CYCLOHEXANE

CYCLIC HYDROCARBON HAS A CLOSED RING STRUCTURE OF CARBON AND HYDROGEN ATOMS

NYLON PRODUCTION

ALSO PAINT AND VARNISHING

NON-POLAR SOLVENT = DISSOLVES FATS, WAXES, OILS, RESINS

LINK BETWEEN HALOGENATED HYDROCARBONS ESPECIALLY CHLORINE CONTAINING AND UV LIGHT EXPOSURE OR HEAT

FORMATION OF TOXIC PHOSGENE GAS

PHOTO OXIDATION REACTION

THINK OF CHLOROFORM, TRICHLOROETHYLENE, METHYL CHLORIDE SOLVENTS

USING CHLORINATED SOLVENTS FOR CLEANING METALS BEFORE WELDING OR CUTTING IS DANGEROUS!!!! OR BURNING/FIRES ON PVC!!!

AROMATIC COMPOUNDS ARE NOT THE SAME AS AROMATIC HYDROCARBON

AROMATIC COMPOUNDS HAVE A BENZENE RING, P AND ARE STABLE, DELOCALISATION OF PI ELECTRONS

EXAMPLE CRESOLS HAVE A HYDROXYL GROUP ATTACHED TO A BENZENE RING

Carbonyl groups

Ketones

Aldehydes

OH Groups

Phenols

Alcohols

oxygen atom

ether

nitrobenzene

aniline dyes, methaemoglobinemia

Nitropropane - hepatitis, carcinogen

Benzene

Aplastic anaemia

AML

Cytochrome p450 in liver

Urinary tt MA most common,.used for ongoing chronic exposure monitoring and also recent exposure

Urinary S phenyl mercapturic acid

Personal air monitoring plus bei

Oel 1

If smell above 1

Aromaticity: very stable because of pi electrons, delocalization

More stable than alkenes

Substitution reaction rather than additive