1

Glycol and 02/26/2022

Derivatives
‫الحمد هلل رب‬
‫العالمين‬

: DONE BY
JASER YAMIN
BAKR ALAWNA
ODAI MAQBOUL
AMJAD QESHAWI
SANDY MONTHER
ENAS BARAGHITHE
 GLYCOL
Glycols and derivatives, such as ethylene glycol (the most frequent and most
basic member of the class), It's a type of organic substance that belongs to the
alcohol family. Different carbon atoms are connected to two hydroxyl (OH)
.groups

‫الحمد هلل رب العالمين‬ 02/26/2022 2

 HISTORY :
Charles-Adolphe Wurtz, a French
scientist, created ethylene glycol for
.the first time in 1859

‫الحمد هلل رب العالمين‬ 02/26/2022 3

 HISTORY CONT. :

• During World War I, it was made on a small scale for use as a coolant and
an explosive element. When ethylene oxide, a component in its
manufacture, became readily available in 1937, widespread industrial
manufacturing began.

• ethylene oxide
‫الحمد هلل رب العالمين‬ 02/26/2022 4
 HISTORY CONT. :

When it was originally introduced, it

caused a little revolution in aircraft design
since its higher boiling point enabled for
smaller radiators to operate at higher
temperatures when used in place of water
.as an engine coolant

‫الحمد هلل رب العالمين‬ 02/26/2022 5

 HISTORY CONT. :

• Many aircraft manufacturers attempted to adopt evaporative cooling systems

that utilized high-pressure water before ethylene glycol became widely available.
These were invariably faulty and readily damaged in combat due to the fact
that they took up a lot of space on the plane and were easily struck by gunfire.

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 THE ACCIDENTAL POISON THAT FOUNDED THE MODERN FOOD AND
DRUG ADMINISTRATION
(FDA)

In the 1937, Elixir Sulfanilamide was a breakthrough antibiotic—until it killed more than 100 •
patient. The cause of that was the using of diethylene glycol as a solvent. After this disaster The
Modern FDA was founded because other crises and disasters could happen and FDA job is to
.prevent them

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 ‫‪TYPES AND EXAMPLES‬‬

‫ح‬

‫الحمد هلل رب العالمين‬ ‫‪02/26/2022‬‬ ‫‪8‬‬

 Types and Examples cont.
**THERE ARE TWO MAIN TYPES OF GLYCOL :-
1- ETHYLENE GLYCOL :- IS AN ORGANIC COMPOUND WITH
THE FORMULA (CH2OH)2, IS A COLORLESS, SWEET-TASTING
LIQUID.
2- PROPYLENE GLYCOL :- ITS CHEMICAL FORMULA IS
CH3CH(OH)CH2OH, IS A VISCOUS, COLORLESS LIQUID, WHICH
IS NEARLY ODORLESS BUT POSSESSES A FAINTLY SWEET
TASTE.
3- POLYETHYLENE GLYCOL (HO.CH2.(CH2.O.CH2)NCH2OH):- IS A
HIGH MOLECULAR WEIGHT INERT MOLECULE THAT IS
COMMONLY COMBINED WITH ELECTROLYTES . 

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 Types and Examples cont.
***OTHER TYPES:-
A - ETHYL GLYCOL ETHER :-
(C2H5.O.CH2.CH2.OH)
B- METHYL GLYCOL ETHER :-
(CH3.O.CH2.CH2.OH)
.C- DIETHYLENE GLYCOL :- (HO.CH2.CH2.
O.CH2.CH2. OH).

‫الحمد هلل رب العالمين‬ 02/26/2022 10

 Types and Examples cont.

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Glycol uses:
They are utilized in humans to generate
anesthetic and dermal effects.

It's used in a lot of industrial

procedures (e.g. energy, plastics,
automobiles, aluminum building
components, and chemical( as anti-
freezing agents.
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 Glycol uses cont.
**Examples of things we use that contain glycol :-

- Antifreeze Contain the ethylene glycol.

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 ‫‪Glycol uses cont.‬‬

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 Glycol uses cont.
- In food :
Propylene glycol is often used to maintain the moisture in prepared foods
And works to maintain their flavor quality for longer periods of time and
some glycols are used as sweeteners.

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 Glycol uses cont.
- hydraulic brake fluids : contain glycol-ether.

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 ‫‪Glycol uses cont.‬‬

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 Preparation of Ethylene Glycol
18
(EG).
a variety of chemical systems (e.g.,
catalytic and non-catalytic) have been
investigated for the synthesis of EG.

‫الحمد هلل رب العالمين‬ 02/26/2022

.Preparation of Ethylene Glycol (EG) cont 19

It is a prominent member of the class of dihydroxy alcohols known as

:ethylene glycols, dihydric alcohols or diols. We can get it by these methods

‫الحمد هلل رب العالمين‬ 02/26/2022

.Preparation of Ethylene Glycol (EG) cont
.from the hydroxylation of ethylene .1 20

Hydroxylation takes place at both the carbon atoms when the ethylene is
treated with Baeyer’s reagent (cold dilute alkaline solution of potassium
.permanganate)

‫الحمد هلل رب العالمين‬ 02/26/2022

.Preparation of Ethylene Glycol (EG) cont
.From the hydrolysis of ethylene oxide .2 21

Ethylene oxide obtained after catalytic oxidation of ethylene is hydrolysed

in the presence of dilute acid or base at high temperature to ethylene
. glycol

‫الحمد هلل رب العالمين‬ 02/26/2022

.Preparation of Ethylene Glycol (EG) cont
.From Oxalic esters .3 22

Oxalic esters on reduction in the presence of sodium and alcohol give

.ethylene glycol

‫الحمد هلل رب العالمين‬ 02/26/2022

:Fate of Ethylene Glycol (EG) 23

EG is not persistent in air, surface water, soil, or groundwater because it

undergoes rapid biodegradation in aerobic and anaerobic environments
(approximately 100% removal of EG within 24 h to 28 days) and EG does
.not bio-accumulate in aquatic organisms

‫الحمد هلل رب العالمين‬ 02/26/2022

Transport and transfer of Ethylene glycol EG 24

Ethylene glycol has a low vapour pressure (7.9 Pa at 20 °C) so it is

expected to exist almost entirely in the vapour phase if released to the
.atmosphere

‫الحمد هلل رب العالمين‬ 02/26/2022

Diethylene glycol (DEG) 25

It is an organic compound (HOCH2CH2)2O. It is a practically

odorless, colorless, poisonous and hygroscopic liquid with a sweetish taste.
.It is miscible in alcohol, water, acetone, ether and ethylene glycol

‫الحمد هلل رب العالمين‬ 02/26/2022

Sources of Diethylene glycol (DEG) 26

Depending on the conditions, varying amounts of Diethylene glycol and

.related glycols are produced by the partial hydrolysis of ethylene oxide

‫الحمد هلل رب العالمين‬ 02/26/2022

Fate of Diethylene glycol (DEG) 27

1- In water : duo to its release to the environment from its production and
use. Diethylene glycol has been detected in drinking water, ground water,
surface water, and indoor air resulting.

‫الحمد هلل رب العالمين‬ 02/26/2022

.Fate of Diethylene glycol (DEG) cont 28

2- In the atmosphere : When released to the atmosphere, Diethylene glycol

in air in particulate-phase may be removed by wet deposition. vapor-phase
diethylene glycol is degraded by reaction with photo-chemically produced
hydroxyl radicals with an estimated half-life of 13 h.
.Fate of Diethylene glycol (DEG) cont 29

In soil: when released to soil or water, diethylene glycol is highly mobile; -3

volatilization is not expected to be important; adsorption to soil and
sediment is very low. It is not susceptible to photolysis on soil surface, but is
.expected to biodegrade quickly in both soil and water

‫الحمد هلل رب العالمين‬ 02/26/2022

Transport and transfer of Diethylene glycol (DEG) 30

DEG is transported by soil or water and it is highly mobile. transferring

through the atmosphere is not the optimal way for DEG because when
.released to the atmosphere is rabidly removed by environmental factors

‫الحمد هلل رب العالمين‬ 02/26/2022

 Polyethylene glycol (PEG) 31

Polyethylene glycol is a polyether compound derived from petroleum

with many applications, from industrial manufacturing to medicine. The
.structure of PEG is commonly expressed as H−(O−CH2−CH2)n−OH

‫الحمد هلل رب العالمين‬ 02/26/2022

 Sources of Polyethylene glycol (PEG) 32

Polyethylene glycol is produced by the interaction of ethylene oxide with

water, ethylene glycol, or ethylene glycol oligomers. The reaction is
catalyzed by acidic or basic catalysts. Polymer chain length depends on the
.ratio of reactants
HOCH2CH2OH + n(CH2CH2O) → HO(CH2CH2O)n+1H

‫الحمد هلل رب العالمين‬ 02/26/2022

 Fate of Polyethylene glycol (PEG)
33

In water: Polyethylene glycols (PEGs) are frequently used in hydraulic -1

fracturing fluids and have been detected in water returning to the surface
from hydraulically fractured oil and gas wells in multiple basins. Under
toxic conditions, it can reach the ground water and contaminate it
.because of it’s solubility and other physical characteristics
In soil: polyethylene glycols (PEG) with molecular weight up to 20,000 -2
were degraded by soil microorganisms , e.g. Pseudomonas aeruginosa
.which was isolated from soil

‫الحمد هلل رب العالمين‬ 02/26/2022

 .Fate of Polyethylene glycol (PEG) cont
34

the Biodegradation of polyethylene by Waxworms The caterpillar

stage of the Greater wax moth, Galleria mellonella, has intestinal microflora
.with the ability to degrade polyethylene (PE) into ethylene glycol

‫الحمد هلل رب العالمين‬ 02/26/2022

https://www.sciencedirect.com/science/article/abs/pii/S0048969719359261
 .Fate of Polyethylene glycol (PEG) cont
35

In the atmosphere : when released to the atmosphere, the wet air -3

oxidation of aqueous solutions of polyethylene glycol will happen , in
other words it was found that the autocatalytic mechanism of
thermochemical autoxidation was capable of converting macromolecules to
lower molecular weight end-products, such as oligomers and carboxylic
.acids, at very short reaction times and mild operating conditions

‫الحمد هلل رب العالمين‬ 02/26/2022

 Transport and transfer of Polyethylene glycol
(PEG) 36

.It is likely to be move by water more than by air and soil

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Propylene glycol (PPG) 37

Propylene glycol is a stable, odorless, colorless, viscous liquid. It is an excellent

solvent because it is freely miscible with water yet dissolves hydrophobic
substances. Among the glycols, propylene glycol has the lowest toxicity.

‫الحمد هلل رب العالمين‬ 02/26/2022

Sources of Propylene glycol (PPG) 38

The following figures is to some methods used to prepare

propylene glycol:

‫الحمد هلل رب العالمين‬ 02/26/2022

Fate of Propylene glycol (PPG) 39

Upon release to the environment, PPG is expected to partition to and be

transported in surface water and groundwater. Biodegradation is the most
important transformation process in surface waters and soils. Propylene
glycol is rapidly degraded in all environmental media; it is not expected
.to persist or bio-accumulate in aquatic organisms

‫الحمد هلل رب العالمين‬ 02/26/2022

Transport and transfer of Propylene glycol (PPG) 40

propylene glycol will have high mobility in soil and potential to leach into
groundwater because of its solubility in water and lack of adsorption to
.soils

‫الحمد هلل رب العالمين‬ 02/26/2022

 ROUT OF EXPOSURE,
METABOLISM AND EXCRETION

41
 EXPOSURE

-The most prevalent method of exposure to ethylene

glycol poisoning is accidental or intentional
consumption of antifreeze.

42
EXPOSURE CONT.
RISK GROUPS

-Those who live near airports where large amounts of ethylene

glycol are used for aircraft de-icing or hazardous waste sites
contaminated with ethylene glycol, as well as workers in
industries that produce or use products containing ethylene glycol,
are the most common people who are at high risk of glycol
exposure.

43
EXPOSURE CONT.
TOXINS WILL ENTER THE BODY BY:-

1-Eye exposure.

2-Inhalation exposure.

3-Skin exposure.

4-Ingestion exposure.
44
METABOLISM AND EXCRETION

-Ethylene glycol is metabolized in the liver by a series of oxidations that result in a

numbers of different  compounds, including:
1-glycoaldehyde
2-glycolic acid
3-glyoxylic acid
4-oxalic acid
-These compounds are even more hazardous than ethylene glycol.
-Alcohol dehydrogenase (ADH) catalyzes the transformation of ethylene glycol into
glycoaldehyde.
-its The rate-limiting step in this metabolic process.
45
METABOLISM AND
EXCRETION CONT.

46
 METABOLISM AND EXCRETION CONT.

-The liver metabolizes about 80% of an absorbed

dose of ethylene glycol, a tiny percentage of
ethylene glycol goes through the urine intact, and
the breakdown of ethylene glycol metabolites can
produce CO2, which is expelled through the
lungs.

47
‫‪02/26/2022‬‬ ‫الحمد هلل رب العالمين‬ ‫‪48‬‬
 Side effects cont.
GLYCOLS ARE LINKED TO A HIGHER RISK
OF DEATH AND SERIOUS MORBIDITY.
ETHYLENE GLYCOL IS THE MOST TOXIC
AND DANGEROUS ONE AND IT IS MORE
ENCOUNTERED THAN OTHER GLYCOLS
LIKE:
• DIETHYLENE GLYCOL
• PROPYLENE GLYCOL
• ETHYLENE GLYCOL MONOBUTYL ETHER
(EGBE)
• ETHYLENE GLYCOL MONOMETHYL
ETHER (EGME)
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SIDE AND ADVERSE EFFECTS CONT.

-GLYCOL COMMON SIDE EFFECTS:

1. GI DISTRESS (NAUSEA,VOMMITING, STOMACH CRAMPS AND IRRITATION,
BLOATING, RECTAL IRRITATION).
2. INSOMNIA (SLEEP PROBLEMS).
3. DEHYDRATION (MOUTH DRYNESS, EXCESSIVE SWEATING)
4. DIZZINESS, HEADACHE

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 SIDE AND ADVERSE EFFECTS CONT.

- RARE BUT SEVERE SIDE EFFECTS INCLUDE:

• ALLERGIC REACTIONS (EX; HIVES),ANAPHYLAXIS ,ANGIOEDEMA.
• ACIDOSIS.
• HIGH LEVEL OF URIC ACID IN THE BLOOD.
• CNS SYMPTOMS (EX; SEIZURES, MUSCLE TREMORS,
• DECREASED LEVEL OF CONSCIOUSNESS ,CONFUSION)

‫الحمد هلل رب العالمين‬ 02/26/2022 51

Hives
 SIDE AND ADVERSE EFFECTS CONT.

• CARDIOPULMONARY PROBLEMS (EX; ATRIAL FIBRILLATION, ABNORMAL HEART

RHYTHM, ASYSTOLE, TROUBLE BREATHING.

• DECREASED KIDNEY FUNCTION THAT MAY PROGRESS TO RENAL TOXICITY AT

END STAGIES.

• HEPATIC DYSFUNCTION.

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 SIDE AND ADVERSE EFFECTS CONT.

• GI BLEEDING , FROM STOMACH, ESOPHAGUS OR DUDENUM .

• FLUID RETENTION AND PUFFY FACE, SWELLING OF THE TONGUE.
• LOSS OF APPETITE.
• BLUE-COLOR LIPS
• SUNKEN-EYES
• PALE, CRACKED, DRY SKIN.

‫الحمد هلل رب العالمين‬ 02/26/2022 53

 HOW CAN WE REDUCE THE
?GLYCOLS CONTAMINATION

‫الحمد هلل رب العالمين‬ 02/26/2022 54

 HOW CAN WE REDUCE THE GLYCOLS
.CONTAMINATION? CONT
In 2013, 14% of facilities that reported glycol ethers also said they
had recently implemented source reduction activities. Changing
paints, coatings, cleaning materials, or product formulas to reduce
glycol ether use is a common reported activity. Facilities also reported
altering production schedules to reduce the usage of glycol ethers for
cleaning by minimizing equipment, feedstock, and/or color
.changes
‫الحمد هلل رب العالمين‬ 02/26/2022 55
 HOW CAN WE REDUCE THE GLYCOLS
.CONTAMINATION? CONT

:Examples include
A kitchen cabinet and countertop manufacturer -1
switched to a new cleaning solution
.that didn't contain glycol ethers

‫الحمد هلل رب العالمين‬ 02/26/2022 56

 HOW CAN WE REDUCE THE GLYCOLS
.CONTAMINATION? CONT
A burial casket manufacturer reduced the number -2
of color changeovers through batch production and
increased its first-pass yield, reducing its releases of
.glycol ethers

‫الحمد هلل رب العالمين‬ 02/26/2022 57

 HOW CAN WE REDUCE THE GLYCOLS
.CONTAMINATION? CONT
A printed circuit board company altered equipment -3
and process chemistry over several years to lower the
.amount of glycol ethers needed

‫الحمد هلل رب العالمين‬ 02/26/2022 58

 HOW CAN WE REDUCE THE GLYCOLS
.CONTAMINATION? CONT
A new paint line was built at a facility that makes -4
aluminum building components, dramatically
.lowering glycol ether air emissions

‫الحمد هلل رب العالمين‬ 02/26/2022 59

 HOW CAN WE REDUCE THE GLYCOLS
.CONTAMINATION? CONT
Between 2003 and 2013, facilities reported a 38 percent
reduction in glycol ether emissions and a 55 percent reduction
.in total waste managed

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 References 61

https://byjus.com/chemistry/ethylene-glycol/ https://pubs.acs.org/doi/10.1021/es504038a
https://pubmed.ncbi.nlm.nih.gov/11302583/
https://www.who.int/ipcs/publications/cicad/en/cicad22.pdf
https://www.jem-journal.com/article/S0736-4679(07)00467-2/fulltext /Lu Yu, in
Encyclopedia of Toxicology (Second Edition), 2005
Bailey FE, Koleske JV (1990). Alkylene oxides and their polymers / Polyethylene glycol,
Chemindustry.ru
‫الحمد هلل رب العالمين‬ 02/26/2022
 References cont. 62

https://www.atsdr.cdc.gov/csem/ethylene-propylene-glycol/biological_fate.html
https://www.cdc.gov/niosh/ershdb/emergencyresponsecard_29750031.html
https://www.epa.gov/sites/default/files/2015-10/documents/p2_spotlight_glycol_ethers.pdf
https://www.aafp.org/afp/2002/0901/p807.html
https://www.sciencedirect.com/science/article/abs/pii/S0048969719359261
 References cont. 63

https://www.researchgate.net/figure/Commercial-synthesis-of-propylene-glycol_fig2_305366517
https://pubmed.ncbi.nlm.nih.gov/24984837/ ////
https://thechemco.com/chemical/diethylene-glycol/
Karyn Bischoff DVM, MS, DABVT, in Small Animal Toxicology (Third Edition), 2013 ///
https://www.atsdr.cdc.gov/ToxProfiles/tp189-c5.pdf //
https://www.sciencedirect.com/science/article/pii/0009250996002722 ///
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC187047/
https://pubs.rsc.org/en/content/articlelanding/2019/em/c8em00291f