What is a solvent?

Chemical substance which is used to dissolve or dilute other

substances and materials (solutes) without chemical changes.
The solvent may be inorganic and organic.
We will discuss exclusively the inorganic non-aqueous
solvents.
Uses of Solvents

As a Solvent As Something Else

Dissolution Fuels (gasoline, octane)
Extraction Feedstock (raw material)
Drugs of abuse (alcohol)
Degreasing
Beverages
Inks, dyes, paints,
Antifreeze (lowers
coatings
freezing point of water-
Dilution, dispersal
based liquid, also called
Dry cleaning coolant used in the
radiator of automobiles)
 Inorganic solvent
An inorganic non-aqueous solvent is a solvent other
than water (only aqueous inorganic solvent), that is not an
organic compound (doesn’t contain carbon). Examples are
liquid ammonia, liquid sulfur dioxide, phosphoryl
chloride, dinitrogen tetroxide, antimony trichloride,
bromine pentafluoride, hydrogen fluoride, pure sulfuric
acid and other inorganic acids. These solvents are used in
chemical research and industry for reactions.
 Classification of solvents
Solvents can be classified in a number of ways depending on
their physical and chemical properties:

1st classification: based on proton-donor and proton-acceptor

property of solvents.
2nd classification: based on the fact that ” like dissolves like”
(polar and non-polar nature of the solvents).
3rd classification: based on aqueous and non- aqueous nature.
1st classification:
1. Protic or protonic solvents: These solvents have hydrogen atoms in
their formula and are of two types:
 (A)Acidic or protogenic solvents: have strong tendency to donate
protons. Examples: H2SO4,HCl,CH3COOH,HCN.
 (B) Basic or protophilic solvents: have strong tendency to accept
protons. Examples: NH3, amines, N2H4.

2. Aprotic or non-protonic solvents: may or may not have hydrogen in

their formula and neither donate nor accept protons. Examples:
C6H6,CHCl3,CCl4,SO2, BrF4.

3. Amphi-protic or amphoteric solvents: have hydrogen in their formula

and can act both as acids and bases. These solvents dissociate freely into
protons and anions. Examples are: H2O CH3COOH.
2nd classification:

1. Ionizing solvents or Polar solvents: polar or ionic in nature and

dissolve ionic compounds and initiate ionic reactions. These exist as ions
in their pure state and thus are weak conductors of electricity. These have
high values of dielectric constants. Because of their polar nature they
have strong tendency to form associated structures. Examples are:
H2O,NH3, HF, SO2 etc.

2. Non-ionizing solvents or non-polar solvents: non-polar or non-ionic

in nature and hence dissolve only non-polar or neutral compounds and
do not initiate ionic reactions. These have low dielectric constants and
have little associating and solvating tendency between the solute and
solvents. Examples: C6H6, CCl4 is non-polar. Most of the organic
solvents are non-polar in nature.
3rd classification: Aqueous and Non-aqueous Solvents
The solvents other than water are called non-aqueous solvents. The
groups obtained as a result of self-ionization of H2O and non-aqueous
solvents are analogous to each other, e.g., H3O+ and OH- groups
obtained from self-ionization of H2O are analogous to NH4+ and NH2-
groups respectively resulted from the self-ionization of liq- NH3. This is
called parent solvent concept and a large number of chemical reactions
have been correlated in terms of this concept. Some of the parent
solvents and analogous groups are given below:

H2O + H2O = H3O+ + OH-

NH3 + NH3 = NH4+ + NH2-
NH2OH + NH2OH = NH3OH+ + NHOH-
H2S + H2S = H3S+ + SH-
 The most popular inorganic (not containing
carbon) solvents are water (H2O) and aqueous solutions
containing special additives (surfactants, detergents, PH
buffers). Other inorganic solvents are liquid
anhydrous Ammonia (NH3), concentrated sulfuric acid
(H2SO4), sulfuryl chloride fluoride (SO2ClF).
 Organic solvents
Oxygenated solvents
Oxygenated solvent is an organic solvent, molecules of which
contain oxygen. Oxygenated solvents are widely used in the
paints, inks, pharmaceuticals, fragrance sectors, adhesives,
cosmetics, detergents, food industries. Examples of
oxygenated solvents: alcohols (ethanol, methanol), esters
(methyl acetate, ethyl acetate) ketones (acetone), glycols
(diethylene glycol, propylene glycol), ethers.

Hydrocarbon solvents
Molecules of hydrocarbon solvents consist only of hydrogen and
carbon atoms.
Aliphatic solvents
Molecules of aliphatic solvents have straight-chain structure.
Hexane, gasoline, kerosene are aliphatic solvents.

White spirits (mineral turpentine spirits)

White spirit is a mixture of aromatic and paraffinic
hydrocarbons.

Pure aromatic solvents
Molecules of pure aromatic solvents have benzene ring
structure. Examples of pure aromatic solvents are benzene,
toluene and xylene.
Halogenated solvents
Halogenated solvent is an organic solvent, molecules of which contain
halogen atoms: chlorine (Cl), fluorine (F), bromine (Br) or iodine (I).

Accordingly to the type of halogen, halogenated solvents are classified

into the following categories:

 Chlorinated solvents
The common chlorinated solvents are methylene chloride (Dichloro
methane) (CH2Cl2), carbon tetrachloride (CCl4)), chloroform (CHCl3).
Fluorocarbon solvents
Examples of fluorocarbon solvents: dichlorofluoromethane
(freon 21, CHCl2F), trichlorofluoromethane (freon 11, CCl3F),
tetrafluoromethane (freon 14, CF4)-used in refrigerator.
Brominated solvents
Examples of brominated solvents: ethylene dibromide (1,2-
dibromoethane, BrCH2-CH2Br), methyl bromide, (bromomethane,
CH3Br).
Iodinated solvents
Examples of iodinated solvents: n-butyl iodide (1-iodobutane,
CH3CH2CH2CH2I), methyl iodide (iodomethane, CH3I).
 Antioxidant
Oxidation is a chemical reaction that transfers electrons or
hydrogen from a substance to an oxidizing agent.
Oxidation reactions can produce free radicals. In turn,
these radicals can start chain reactions. When the chain
reaction occurs in a cell, it can cause damage or death to
the cell. Antioxidants terminate these chain reactions by
removing free radical intermediates, and inhibit other
oxidation reactions. They do this by being oxidized
themselves, so antioxidants are often reducing agents.
An antioxidant is a molecule that inhibits
the oxidation of other molecules.
Defining “antioxidant”
The term “antioxidant” has many definitions:
Chemical definition: “a substance that opposes oxidation
or inhibits reactions promoted by oxygen or peroxides”
Biological definition: “synthetic or natural substances that
prevent or delay deterioration of a product (oxidative
degradation), or are capable of counteracting the
damaging effects of oxidation in animal tissues”
Institute of Medicine definition: “a substance that
significantly decreases the adverse effects of reactive
species such as ROS (Reactive Oxygen Species) on normal
physiological function in humans.
Types of antioxidants
Inorganic antioxidants: Sulfur dioxide (SO2), Sodium
metabisulfite (Na2S2O3.5H2O), Sodium nitrite (NaNO2),
Sodium sulfate (Na2SO3).

Organic antioxidants: polyphenols (tannic acid, gallic

acid), flavonoids, ascorbic acid, vitamin E, C & A,
carotenoids (dietary antioxidants), enzymes such as
catalase, peroxidases etc.
Sources of antioxidants in the diet:

Polyphenols, carotenoids & vitamins

Cranberries & blueberries (flavonoids & tannins)
Strawberries (ellagic acid, ellagitannins)
Tea (catechins, tannins)
Chocolate (catechins)
Onions (quercetin)
Spinach & leafy greens (lutein & zeaxanthin)
Eggs (lutein)
Citrus fruits (Vitamin C)
Plant oils (Vitamin E & omega-3)
Red wine (tannins, resveratrol, flavonoids)
 Radicals and ROS
The enemy: “Reactive Oxygen Species” (ROS) are
highly reactive free radicals
 Superoxide (O2-.) – protonation forms .OOH
 Hydroxyl radical (.OH) most reactive
 Peroxy radicals (.OOH,.OOR) more selective
 Alkoxy radicals (.OR)
 Peroxynitrite (ONOO-)
They form as the result of stress, inflammation, and the
human body’s natural defenses in vivo, many are formed
in the mitochondria, by phagocytes and peroxisomes, and
by CYP450 activities. They target tissue, proteins, lipids
and DNA. Aging = cumulative damage of cells over the
years.
Therefore, antioxidants are molecules capable of reducing
the causes or effects of oxidative stress. Oxidative stress
can be caused by environmental factors, disease, infection,
inflammation, aging (ROS production). ROS or “reactive
oxygen species” include free radicals and other oxygenated
molecules resulting from these factors.
What do antioxidants do?-Mechanism
 Prevent formation of ROS: Inhibit xanthine oxidase,
COX, LOX, chelate metals.
 Scavenge/remove ROS before they can damage important
biomolecules.
 Aid the human body’s natural defenses
 Up regulate superoxide dismutase (O2-.), catalase
(H2O2), glutathione peroxidase (endogenous
Antioxidant)
 Repair oxidative damage
 Eliminate damaged molecules
 Prevent mutations
 Lipid oxidation: a radical mechanism
UFAs (R-H) are major target due to reactivity of C=C
Initiation:
X· + RH  X-H + R·
ROOH  RO· + HO· or 2 ROOH  RO· + ROO· + H2O
Propagation
R· + O2  ROO·
ROO· + R’H  ROOH + R’·
Termination
ROO· + R’OO·  ROOR’ + O2
RO· + R’·  ROR’
Hydroperoxides (ROOH) also oxidize to aldehydes and
ketone by-products
Flavonoids as antioxidants
Flavonoids are especially effective because of structural
features including:
Conjugation to further stabilize radicals
ortho-dihydroxysubstituted B ring allows for
chelation of pro-oxidant metal ions
(Fe2+, Fe3+, Cu2+, etc.)
 -unsaturated ketone and 3-OH on C-ring .
OH
OH

HO O

OR
OH O