ASSIGNMENT TOPIC:

Waxes, their structure, types and commercial

importance.

SUBMITTED TO:
Prof. Doctor Shahid

SUBMITTED BY:
Faizan Shah

Class:
M.Phil Zoology (1st Semester)
(2014 – 16)
Contents

a. Introduction

b. Structure

c. Properties

d. Types

e. Functions and Applications

f. Uses

g. Importance

h. Summary

i. References
WAXES
Introduction:
Waxes is a general term used to refer to the mixture of long-chain apolar lipids forming a
protective coating (cutin in the cuticle) on plant leaves and fruits but also in animals (wax of
honeybee, cuticular lipids of insects, spermaceti of the sperm whale, skin lipids, uropygial
glands of birds, depot fat of planktonic crustacea), algae, fungi and bacteria. Some waxes are
of mineral origin. Montan wax originates from mob or lignite, that fossilized compound
representing a late step of the transformation of vegetal into hydrocarbons.

The various materials named waxes do not form a chemically homogeneous group. All waxes
are water-resistant materials made up of various substances including hydrocarbons (normal or
branched alkanes and alkenes), ketones, diketones, primary and secondary alcohols, aldehydes,
sterol esters, alkanoic acids, terpenes (squalene) and monoesters (wax esters), all with long or
very long carbon chains (from 12 up to about 38 carbon atoms) and solid in a large range of
temperature (fusion point between 60 and 100°C). More commonly, waxes are esters of an
alcohol other than glycerol (long chain alcohol, sterol, hydroxycarotenoids, vitamin A) and a
long chain acid (wax esters). Wax esters are saponified by hot alkaline solutions and give a fatty
acid and an alcohol. They are soluble in aromatic solvents, chloroform, ethers, esters and
ketones.

Chemical structure:
Wax is a type of long chain apolar lipid which made up of various n-alkanes, ketones, primary
alcohol, secondary alcohols, monoesters, beta diketones, aldehydes,etc. Waxes will form
protective coating on plants and fruits, and in animal (example: beewax, whale spermaceti,
etc.). More commonly, wax is ester of alcohol and fatty acids. They differ from fats since they
don’t have triglyceride ester of three fatty acids. Waxes are water resistant, so they are
insoluble in water.

Fig: Structure of a Wax Ester

Properties:
Due to the versatility of waxes, nature has manipulated them for their water-resistant
properties, colligative properties (high melting point, relatively low viscosity at high
temperatures, transparency, etc.) and coating properties.
Types of Waxes
1. Beeswax –for consumption
2. Chinese Wax – for polishes
3. Ear Wax – used as a protective layer over the ear membrane
4. Lanolin – for rust prevention and cosmetics
5. Shellac – used as a wood sealant
6. Spermaceti – for cosmetics and leatherworking
7. Vegetable (many different types extracted from plants) – used as
a protective layer on the plant to prevent loss of water
8. Mineral – used as fine polishes
9. Petroleum – fuels, paints, culinary, candles
10. Synthetic – modified waxes for use in the medical field

Other Types of waxes

Paraffin and Microcrystalline
Waxes are derived from petroleum. They are easy to recover and offer a wide range of physical
properties that can often be tailored by refining processes. Most producers offer two distinct
types of petroleum waxes:

Paraffins which is distinguished by large, well formed crystals; and microcrystallines, which are
higher melting waxes with small, irregular crystals. Microcrystalline wax contains substantial
proportions of branched and cyclic saturated hydrocarbons in addition to normal alkanes.

Synthetic waxes
Entered the wax market in the past 50 years. Polyethylene waxes are low molecular weight
polyethylenes (less than 10,000 Mn) having wax-like properties made by either high-pressure
or low-pressure (Zeigler-type catalyst) polymerization. All such waxes have the same basic
structure, but the various production processes yield products with distinctly different
properties, and these have a major impact on the use of products. Products from one
manufacturer may satisfy one particular application, while product from a similar process will
not work well.

Fischer-Tropsch (FT)
Wax is a synthetic wax produced by the polymerization of carbon monoxide under high
pressure, a technology used in the emerging natural Gas to Liquid (GTL) projects. The
hydrocarbon product of FT reaction is distilled to separate the mix into fuels products and
waxes with melting points ranging from about 45 - 106ºC. Currently FT waxes are commercially
produced in South Africa and Malaysia. It is estimated that the overall synthetic wax
consumption in North America in 2010 was 420 million lbs., of which FT wax accounts for about
195 million lbs.

Alpha olefin waxes:

Synthetically derived from ethylene via a Ziegler-Natta catalyst. The process results in a Schulz-
Flory distribution of alpha olefins ranging from C4 through C30+. These are distilled into the
individual carbon fractions or carbon fraction blends. Due to the high melting points of the
waxes, C20 and higher carbon numbers are fractionated into blends.

Montan wax:
Derived by solvent extraction of lignite. The earliest production of montan wax on a commercial
scale was in Germany during the latter half of the nineteenth century. Germany continues to
lead the world in production of montan wax; although some montan wax is produced in the
United States from the Ione lignite bed in California. The composition of montan wax varies
geographically with production, but includes varying amounts of wax, resin and asphalt.

Other mineral waxes

Peat waxes, ozokerite and ceresin waxes
Beeswax
Has been traded for over 2,000 years and references to "wax" before the 19th century typically
meant beeswax. Yellow beeswax is secreted by bees to build honeycombs; the empty comb is
melted in boiling water to recover the wax.

Other animal-based waxes

Include lanolin from the wool of sheep; ambergris produced in the intestines of sperm whales;
and tallow from beef fat.

Carnauba wax
Recovered from a variety of palm tree which grows almost exclusively in northeastern Brazil.
Carnauba wax forms on the fronds of the trees and is recovered by cutting and drying the
fronds, then mechanically removing the wax. Impurities are removed from the wax by melting
and filtering, or centrifuging.

Candelilla wax
Harvested from shrubs grown in the Mexican states of Coahuila and Chihuahua and in Texas.
The entire mature plant is uprooted and immersed in boiling water acidified with sulfuric acid;
the wax floats to the surface for recovery.

Other vegetable-based waxes

Include Japan wax, produced on the berries of a small tree native to Japan and China; ouricury
wax, obtained from the fronds of another type of palm tree growing in Brazil; rice-bran wax,
extracted from crude rice bran; and jojoba, obtained from the seeds of the jojoba plant grown
in parts of Costa Rica, Israel, Mexico and the United States, and soy wax which is produced by
hydrogenated soybean oil.

Functions and Applications:

Waxes contain many functions in society. Man has manipulated and synthesized many waxes to
be used for cosmetics, sealants and lubricants, insecticides, UV protection, energy reserves,
food, etc

Soap:
It is a mixture of sodium salts forming by adding sodium hydroxide or sodium carbonate to
natural fatty acids. The density of soap will be decreased by air bubble forming. The general
reaction in producing soap:

Fat + NaOH → soap + glycerol

Detergent:
Detergent is a material that helps in cleaning. Detergent contains one of more surfactants which are capable of
reducing the surface tension of liquid such as water. Commonly, detergent consists of long chain hydrocarbon and
ionic group (such as alky sulfate or derivative of ammoniac group).

Types of Detergents:

Anionic
These detergents are man-made and consist of long hydrocarbon chains and a water-soluble
ionic group, which is usually negatively charged. These detergents are commonly known as
surfactants, or alkyl benzene sulfonates
Cationic
These detergents are also man-made, and they only differ from anionic detergents in that the
water-soluble ionic group is positively charged. These detergents are primarily derivatives of
ammonium and are commonly used as a germicide and in shampoo.
Neutral
These type of detergents contain the same general set up as all other detergents, except it’s
overall charge is neutral. The head of the detergent is polar due to the presence of three
hydroxyl groups and an ester group.
Natural
Natural detergents such as bile salts (sodiumglycoholate) are made in the liver. These
detergents are derivatives of cholesterol, a type of lipid. Its main function is digestion. The bile
salt is capable of emulsifying fats and oils such that enzymes may break them down further.
Functions of Detergents
Detergents have many functions and applications including cleaning off fats and oils, softening
materials, acting as aromas or abrasives, or sanitizing and disinfecting. Though detergent and
soap are used interchangeably, people can see the various uses of detergents in common house
products including hand soap, laundry detergent, dish and glass detergents, etc.

Chemistry of waxes
Waxes are organic compounds that characteristically consist of long alkyl chains. They may also
include various functional groups such as fatty acids, primary and secondary long chain
alcohols, unsaturated bonds, aromatics, amides, ketones, and aldehydes. They frequently
contain fatty acid esters as well. Synthetic waxes Ceroline are often long-chain hydrocarbons
(alkanes or paraffins) that lack functional groups.[1]
Plant and animal waxes
Waxes are synthesized by many plants and animals. Those of animal origin typically consist of
wax esters derived from a variety of carboxylic acids and fatty alcohols. In waxes of plant origin,
characteristic mixtures of unesterified hydrocarbons may predominate over esters. [2] The
composition depends not only on species, but also on geographic location of the organism.
Animal waxes
The most commonly known animal wax is beeswax but other insects secrete (release) waxes.
A major component of the beeswax used in constructing honeycombs is the ester myricyl
palmitate which is an ester of triacontanol and palmitic acid. Its melting point is 62-
65 °C. Spermaceti occurs in large amounts in the head oil of the sperm whale. One of its main
constituents is cetyl palmitate, another ester of a fatty acid and a fatty alcohol. Lanolin is a wax
obtained from wool, consisting of esters of sterols.[1]
Plant waxes
Plants secrete waxes into and on the surface of their cuticles as a way to control evaporation,
wettability and hydration.[3] The epicuticular waxes of plants are mixtures of substituted long-
chain aliphatic hydrocarbons, containing alkanes, alkyl esters, fatty acids, primary
and secondary alcohols, diols, ketones, aldehydes.[2] From the commercial perspective, the
most important plant wax is carnauba wax, a hard wax obtained from the Brazilian
palm Copernicia prunifera. Containing the ester myricyl cerotate, it has many applications, such
as confectionery and other food coatings, car and furniture polish, floss coating, and surfboard
wax. Other more specialized vegetable waxes include candelilla wax and ouricury wax.
Modified plant and animal waxes
Plant and animal based waxes or oils can undergo selective chemical modifications to produce
waxes with more desirable properties than are available in the unmodified starting
material This approach has relied on green chemistry approaches including olefin metathesis
and enzymatic reactions and can be used to produce waxes from inexpensive starting materials
like vegetable oils.
Polyethylene and related derivatives
As of 1995, about 200 million kilograms/y were consumed.
Polyethylene waxes

These are manufactured by one of three methods:

1-direct polymerization of ethylene (may include co -monomers also)

2- thermal degradation of high molecular weight polyethylene resin

3- recovery of low molecular weight fractions from high molecular weight resin production.

Each production technique generates products with slightly different properties. Key properties
of low molecular weight polyethylene waxes are viscosity, density and melt point.

The Versatility of Waxes

As supplies of limited minerals have declined, innovators have developed ways to replace the
functionality of these materials by modifying other waxes; this is a trend that continues today.

Microcrystalline hydrocarbon and synthetic waxes may be modified to meet specific market
needs, most often to match performance characteristics of animal or vegetable waxes. In most
cases, the first step is air oxidation of the wax, with or without catalysts. An alternative
approach is to react the wax with a carboxylic acid at high temperature. Oxidized wax can be
further modified by saponification or esterification at the carboxyl sites. Oxidized wax is easily
emulsified in water through the use of surfactants or simple soaps, and is widely used in many
coating and polish applications. Petroleum waxes modified in this way can compete in specific
areas with vegetable and insect waxes.

Polymers of higher olefins (e.g. Carbon Number>20) have wax-like properties and are sold as
synthetic waxes. The polymerization process yields highly branched materials with broad
molecular weight distributions. Properties of the individual products are highly dependent on
the olefin monomers and polymerization conditions. Melting points range from 54 - 74oC. The
unique structure makes these products very effective when used in additive amounts to modify
the properties of paraffin wax, primarily for use in candles. The products can increase the
hardness and opacity of the paraffin with minimal impact on cloud point or viscosity. Other
uses include mold release for polyurethane foams, additives for casting wax, and additives for
leather treating.

Examples:
Candles

One of the oldest uses of wax, but still vital. No longer used for primary illumination, candles
are the fastest growing segment of the wax market with new decorative and therapeutic uses.
Chlorinated paraffins

Chemicals manufactured by chlorination of paraffin waxes. The largest application for

chlorinated paraffins is as a plasticiser and flame-retardant in flexible PVC. It is also used as an
extreme pressure-additive for metalworking fluids and other lubricants.
Corrugated board

Food-grade wax is applied to corrugated containers in order to provide strength and

waterproofing for food packaging during transportation.
Coatings
Wax can be used to form a coating that allows oxygen to pass but not water; generating
numerous applications in such diverse areas as cosmetics, food, packaging, furniture, time
release properties, etc.
Flexible packaging
Food-grade waxes and wax blends are used in laminating compounds and surface coatings to
provide strength, to waterproofing, and improve appearance and moisture-vapor transmission.
Cosmetics and pharmaceuticals
Fully-refined wax is non-toxic, and many products are approved for direct use in food and
personal care formulations. Waxes are widely used in the cosmetic industry in products such as
lipstick, mascara, moisturizing creams and sunblock.
Chewing gum
Chewing gum base is a compound of elastomers, resin and food-grade wax to which other
materials are added to produce chewing gum. Hard, high melt-point waxes are used in this
application, including microcrystalline and candelilla waxes.

Food
Food grade wax is used to cover certain types of cheese that would dehydrate if not properly
protected. It is sprayed on citrus and other fruit to protect from oxidation and enhance
appearance, and in meat and bone wraps.
Hot melt adhesives
waxes are present in most hot melt adhesive formulations to control the viscosity of the
adhesive and contribute to open time, flexibility and elongation.
Inks
Graphical printing inks include wax in their formulation as an anti-scuff agent.
Investment casting
In the "lost wax" method of casting jewelry, and other industrial products, a wax model of the
piece is made and used to create a clay mold. The wax is melted out and the clay is used to cast
the final piece.
Polishes
The application of waxes to wooden floors to improve their appearance and provide protection
dates back several hundred years. It serves to retard the penetration of air and moisture,
thereby increasing the life of the flooring material as well as preventing abrasion by surface grit.
PVC
Two different lubricants are used in the manufacture of polyvinyl chloride thermoplastic:
internal and external; and two different types of wax are used in the lubricants. Internal
lubricants are formulated to help PVC flow in the manufacturing process by forming a solution
with PVC. External lubricants are not soluble in PVC and can produce a film between the PVC
and its extrusion equipment.
Tire and rubber
Wax is a vital component in rubber tire formulations and is added for protection from
atmospheric ozone that will "dry" unprotected rubber, causing cracking that compromises the
strength of the tire. Wax creates a physical barrier between the tire surface and the
atmosphere.

Uses
Waxes are mainly consumed industrially as components of complex formulations, often for
coatings.[ The main use of polyethylene and polypropylene waxes is in the formulation of
colourants for plastics. Waxes confer matting effects and wear resistance to paints.
Polyethylene waxes are incorporated into inks in the form of dispersions to decrease friction.
They are employed as release agents, find use as slip agents in furniture, and confer corrosion
resistance.
Candles
Waxes and hard fats such as tallow are used to make candles, used for lighting and decoration.
Wax products
Waxes are used as finishes and coatings for wood products.[10] Beeswax is frequently used as a
lubricant on drawer slides where wood to wood contact occurs.
Other uses
Sealing wax was used to close important documents in the Middle Ages. Wax tablets were used
as writing surfaces. There were different types of wax in the Middle Ages, namely four kinds of
wax (Ragusan, Montenegro, Byzantine, and Bulgarian), "ordinary" waxes from Spain, Poland,
and Riga, Unrefined waxes and colored waxes (red, white, and green). Waxes are used to
make wax paper, impregnating and coating paper and card to waterproof it or make it resistant
to staining, or to modify its surface properties. Waxes are also used in shoe polishes, wood
polishes, and automotive polishes, as mold release agents in mold making, as a coating for
many cheeses, and to waterproof leather and fabric. Wax has been used since antiquity as a
temporary, removable model in lost-wax casting of gold, silver and other materials.
Wax with colorful pigments added has been used as a medium in encaustic painting, and is
used today in the manufacture of crayons, china markers and colored pencils. Carbon paper,
used for making duplicate typewritten documents was coated with carbon black suspended in
wax, typically montan wax, but has largely been superseded by photocopiers and computer
printers. In another context, lipstick and mascara are blends of various fats and waxes colored
with pigments, and both beeswax and lanolin are used in other cosmetics. Ski wax is used
in skiing and snowboarding. Also, the sports of surfing and skateboardingoften use wax to
enhance the performance.
Some waxes are considered food-safe and are used to coat wooden cutting boards and other
items that come into contact with food. Beeswax or coloured synthetic wax is used to
decorate Easter eggs in Romania, Ukraine, Poland, Lithuania and the Czech Republic. Paraffin
wax is used in making chocolate covered sweets.
Wax is also used in wax bullets, which are used as simulation aids.

Specific examples:
Animal waxes

 Beeswax - produced by honey bees

 Chinese wax - produced by the scale insect Ceroplastes ceriferus
 Lanolin (wool wax) - from the sebaceous glands of sheep
 Shellac wax - from the lac insect Kerria lacca
 Spermaceti - from the head cavities and blubber of the sperm whale

Vegetable waxes

 Bayberry wax - from the surface wax of the fruits of the bayberry shrub, Myrica faya
 Candelilla wax - from the Mexican shrubs Euphorbia cerifera and Euphorbia antisyphilitica
  Carnauba wax - from the leaves of the Carnauba palm, Copernicia cerifera
 Castor wax - catalytically hydrogenated castor oil
 Esparto wax - a byproduct of making paper from esparto grass, (Macrochloa tenacissima)
 Japan wax - a vegetable triglyceride (not a true wax), from the berries
of Rhus and Toxicodendron species
 Ouricury wax - from the Brazilian feather palm, Syagrus coronata.
 Rice bran wax - obtained from rice bran (Oryza sativa)
 Soy wax - from soybean oil
 Tallow Tree wax - from the seeds of the tallow tree Triadica sebifera.

Mineral waxes

 Ceresin waxes
 Montan wax - extracted from lignite and brown coal
 Ozocerite - found in lignite beds
 Peat waxes

Petroleum waxes
 Paraffin wax - made of long-chain alkane hydrocarbo

Importance of waxes:

. Waxes, such as that found in the ear, provide a helpful barrier against infection. Earwax collects dirt
and microbes that might otherwise enter the body.
 The wax is produced by the ceruminous glands, they are found in the ear canal and secrete the waxy
substance called cerumen.
 Small particles. It collects dirt and debris in your ear canal and moves it out ofyour ears where you can
wash it off as you wash your face and external ears. Cerumen also helps prevent foreign substances
(including insects) from entering theauditory canal. It forms a layer of protective wax in the ear canal
which is a water repelling shield (ear canals need to be dry to be healthy).
 The wax also is slightly acidic and will not allow the growth of bacteria or fungi. It fights infections as
well, with some mild antibacterial components.
 Waxes are a type of lipid.... lipids consist of waxes, fats, and oils.. lipids store energy for our cells to use
when they need it. sort of like using a bank.without lipids and carbohydrates, whe wouldn't have
enough energy to exersise, and play sports.
 An important characteristic of waxes in living things is that waxes can be produced in living things (if the
organism is dead it cant produce waxes).
 Some important characteristics include the smell, amount, its matabolism, and bio sucks CA all the way.
 An important characteristic of wax in living organisms is there water proof and they produce earwax
which helps keep out microorganisms from entering the ear canal.
 Applying most wax products would not require the use of personal protective equipment.
 The wax used on automobiles fills the pores in the paint of the car. This prevents dirt from building in
these pores. It also provides a thin layer of protection from various elements such as corrosion due to
salt. Waxing also provides a sheen to the paint.

SUMMARY:
Waxes is a general term used to refer to the mixture of long-chain apolar lipids forming a
protective coating (cutin in the cuticle) on plant leaves and fruits but also in animals (wax of
honeybee, cuticular lipids of insects, spermaceti of the sperm whale, skin lipids, uropygial
glands of birds, depot fat of planktonic crustacea), algae, fungi and bacteria. Due to the
versatility of waxes, nature has manipulated them for their water-resistant properties,
colligative properties (high melting point, relatively low viscosity at high temperatures,
transparency, etc.) and coating properties. Waxes contain many functions in society. Man has
manipulated and synthesized many waxes to be used for cosmetics, sealants and lubricants,
insecticides, UV protection, energy reserves, food, etcWaxes are organic compounds that
characteristically consist of long alkyl chains. They may also include various functional
groups such as fatty acids, primary and secondary long chain alcohols, unsaturated bonds,
aromatics, amides, ketones, and aldehydes.These are mainly consumed industrially as
components of complex formulations, often for coatings.[ The main use of polyethylene and
polypropylene waxes is in the formulation of colourants for plastics. Waxes confer matting
effects and wear resistance to paints

References
1. ^ Jump up to:a b EA Baker (1982) Chemistry and morphology of plant epicuticular waxes. In The Plant
Cuticle. Ed. DF Cutler, KL Alvin, CE Price. Academic Press. ISN 0-12-199920-3
2. ^ Jump up to:a b c Uwe Wolfmeier, Hans Schmidt, Franz-Leo Heinrichs, Georg Michalczyk, Wolfgang Payer,
Wolfram Dietsche, Klaus Boehlke, Gerd Hohner, Josef Wildgruber "Waxes" in Ullmann's Encyclopedia of
Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a28_103.
3. Wax-wikipedia https//en.m.wikipedia.org>wiki>wax