Glyceryl Acetate
   HOME

TheInfoList



OR:

Glycerol () is a simple
triol In chemistry, a triol is an organic compound containing three hydroxyl groups ( functional groups),viscous Viscosity is a measure of a fluid's rate-dependent resistance to a change in shape or to movement of its neighboring portions relative to one another. For liquids, it corresponds to the informal concept of ''thickness''; for example, syrup h ...
liquid. The glycerol backbone is found in
lipid Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing ...
s known as
glyceride Glycerides, also known as acylglycerols, are esters formed from glycerol and fatty acids, and are generally very hydrophobic. Glycerol has three hydroxyl functional groups, which can be esterified with one, two, or three fatty acids to form mo ...
s. It is also widely used as a sweetener in the food industry and as a
humectant A humectant is a hygroscopic (water-absorbing) substance used to keep things moist. They are used in many products, including food, cosmetics, medicines and pesticides. When used as a food additive, a humectant has the effect of keeping moistu ...
in
pharmaceutical formulation Pharmaceutical formulation, in pharmaceutics, is the process in which different chemical substances, including the active drug, are combined to produce a final medicinal product. The word ''formulation'' is often used in a way that includes dos ...
s. Because of its three
hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
s, glycerol is
miscible Miscibility () is the property of two substances to mix in all proportions (that is, to fully dissolve in each other at any concentration), forming a homogeneous mixture (a solution). Such substances are said to be miscible (etymologically ...
with
water Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...
and is
hygroscopic Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption (chemistry), absorption or adsorption from the surrounding Natural environment, environment, which is usually at normal or room temperature. If water mol ...
in nature. Modern use of the word glycerine (alternatively spelled glycerin) refers to commercial preparations of less than 100% purity, typically 95% glycerol.


Structure

Although
achiral Chirality () is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is distinguishable from ...
, glycerol is prochiral with respect to reactions of one of the two primary alcohols. Thus, in substituted derivatives, the
stereospecific numbering Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes in eukaryotic cells. They are a type of lipid, of which its composition affects membrane structure and properties. Tw ...
labels the molecule with a ''sn''- prefix before the stem name of the molecule.


Production


Natural sources

Glycerol is generally obtained from plant and animal sources where it occurs in
triglyceride A triglyceride (from '' tri-'' and '' glyceride''; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates ...
s,
ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s of glycerol with long-chain
carboxylic acids In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...
. The
hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
,
saponification Saponification is a process of cleaving esters into carboxylate salts and Alcohol (chemistry), alcohols by the action of aqueous alkali. Typically aqueous sodium hydroxide solutions are used. It is an important type of alkaline hydrolysis. When the ...
, or
transesterification Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. Strong acids catalyze the r ...
of these triglycerides produces glycerol as well as the fatty acid derivative:
Triglycerides can be saponified with
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...
to give glycerol and fatty sodium salt or
soap Soap is a salt (chemistry), salt of a fatty acid (sometimes other carboxylic acids) used for cleaning and lubricating products as well as other applications. In a domestic setting, soaps, specifically "toilet soaps", are surfactants usually u ...
. Typical plant sources include
soybeans The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean. Soy is a staple crop, the world's most grown legume, and an important animal feed. Soy is a key source of f ...
or
palm Palm most commonly refers to: * Palm of the hand, the central region of the front of the hand * Palm plants, of family Arecaceae ** List of Arecaceae genera **Palm oil * Several other plants known as "palm" Palm or Palms may also refer to: Music ...
. Animal-derived
tallow Tallow is a rendered form of beef or mutton suet, primarily made up of triglycerides. In industry, tallow is not strictly defined as beef or mutton suet. In this context, tallow is animal fat that conforms to certain technical criteria, inc ...
is another source. From 2000 to 2004, approximately 950,000 tons per year were produced in the United States and Europe; 350,000 tons of glycerol were produced in the U.S. alone. Since around 2010, there is a large surplus of glycerol as a byproduct of
biofuel Biofuel is a fuel that is produced over a short time span from Biomass (energy), biomass, rather than by the very slow natural processes involved in the formation of fossil fuels such as oil. Biofuel can be produced from plants or from agricu ...
, enforced for example by EU directive 2003/30/EC that required 5.75% of petroleum fuels to be replaced with biofuel sources across all
member states A member state is a state that is a member of an international organization or of a federation or confederation. Since the World Trade Organization (WTO) and the International Monetary Fund (IMF) include some members that are not sovereign states ...
. Crude glycerol produced from triglycerides is of variable quality, with a selling price as low as US$0.02–0.05 per kilogram in 2011. It can be purified in a rather expensive process by treatment with
activated carbon Activated carbon, also called activated charcoal, is a form of carbon commonly used to filter contaminants from water and air, among many other uses. It is processed (activated) to have small, low-volume pores that greatly increase the surface ar ...
to remove organic impurities, alkali to remove unreacted glycerol esters, and
ion exchange Ion exchange is a reversible interchange of one species of ion present in an insoluble solid with another of like charge present in a solution surrounding the solid. Ion exchange is used in softening or demineralizing of water, purification of ch ...
to remove salts. High purity glycerol (greater than 99.5%) is obtained by multi-step distillation; a
vacuum chamber A vacuum chamber is a rigid enclosure from which air and other gases are removed by a vacuum pump. This results in a low-pressure environment within the chamber, commonly referred to as a vacuum. A vacuum environment allows researchers to c ...
is necessary due to its high boiling point (290 °C). Consequently, glycerol recycling is more of a challenge than its production, for instance by conversion to glycerol carbonate or to synthetic precursors, such as
acrolein Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat ...
and epichlorohydrin.


Synthetic glycerol

Although more expensive than production from plant or animal triglycerides, glycerol can be synthesized by various routes. During
World War II World War II or the Second World War (1 September 1939 – 2 September 1945) was a World war, global conflict between two coalitions: the Allies of World War II, Allies and the Axis powers. World War II by country, Nearly all of the wo ...
, synthetic glycerol processes became a national defense priority because it is a precursor to
nitroglycerine Nitroglycerin (NG) (alternative spelling nitroglycerine), also known as trinitroglycerol (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless or pale yellow, oily, explosive liquid most commonly produced by ...
. Epichlorohydrin is the most important precursor. Chlorination of propylene gives
allyl chloride Allyl chloride is the organic compound with the formula C H2=CHCH2 Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a c ...
, which is oxidized with
hypochlorite In chemistry, hypochlorite, or chloroxide is an oxyanion with the chemical formula ClO−. It combines with a number of cations to form hypochlorite salts. Common examples include sodium hypochlorite (household bleach) and calcium hypochlorite ...
to
dichlorohydrin 1,3-Dichloropropan-2-ol (1,3-DCP) is an organic compound with the formula HOCH2CHClCH2Cl. It is a colorless liquid. It is an intermediate in the production of epichlorohydrin. 1,3-DCP is a believed to be a carcinogen and mutagen. The Internati ...
, which reacts with a strong base to give
epichlorohydrin Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscibility, miscible with most p ...
. Epichlorohydrin can be hydrolyzed to glycerol.
Chlorine Chlorine is a chemical element; it has Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between ...
-free processes from propylene include the synthesis of glycerol from
acrolein Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat ...
and
propylene oxide Propylene oxide is an epoxide with the molecular formula C3H6O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols f ...
. :


Applications


Food industry

In food and beverages, glycerol serves as a
humectant A humectant is a hygroscopic (water-absorbing) substance used to keep things moist. They are used in many products, including food, cosmetics, medicines and pesticides. When used as a food additive, a humectant has the effect of keeping moistu ...
,
solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...
, and
sweetener A sweetener is a substance added to food or drink to impart the flavor of sweetness, either because it contains a type of sugar, or because it contains a sweet-tasting sugar substitute. Various natural non-sugar sweeteners (NSS) and artificial s ...
, and may help preserve foods. It is also used as filler in commercially prepared
low-fat Diet food (or dietetic food) refers to any food or beverage whose recipe is altered to reduce fat, carbohydrates, and/or sugar in order to make it part of a weight loss program or diet. Such foods are usually intended to assist in weight loss o ...
foods (e.g.,
cookie A cookie is a sweet biscuit with high sugar and fat content. Cookie dough is softer than that used for other types of biscuit, and they are cooked longer at lower temperatures. The dough typically contains flour, sugar, egg, and some type of ...
s), and as a
thickening agent A thickening agent or thickener is a substance which can increase the viscosity of a liquid without substantially changing its other properties. Edible thickeners are commonly used to thicken sauces, soups, and puddings without altering their ...
in
liqueur A liqueur ( , ; ) is an alcoholic drink composed of Liquor, spirits (often rectified spirit) and additional flavorings such as sugar, fruits, herbs, and spices. Often served with or after dessert, they are typically heavily sweetened and un-age ...
s. Glycerol and water are used to preserve certain types of plant leaves. As a
sugar substitute A sugar substitute or artificial sweetener, is a food additive that provides a sweetness like that of sugar while containing significantly less food energy than sugar-based sweeteners, making it a zero-calorie () or low-calorie sweetener. Arti ...
, it has approximately 27
kilocalories The calorie is a unit of energy that originated from the caloric theory of heat. The large calorie, food calorie, dietary calorie, kilocalorie, or kilogram calorie is defined as the amount of heat needed to raise the temperature of one liter o ...
per
teaspoon A teaspoon (tsp.) is a small spoon that can be used to stir a cup of tea or coffee, or as a tool for measuring volume. The size of teaspoons ranges from about . For dosing of medicine and, in places where metric units are used, for cooking pu ...
(sugar has 20) and is 60% as
sweet Sweetness is a basic taste most commonly perceived when eating foods rich in sugars. Sweet tastes are generally regarded as pleasurable. In addition to sugars like sucrose, many other chemical compounds are sweet, including aldehydes, ketones, ...
as
sucrose Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula . For human consumption, sucrose is extracted and refined ...
. It does not feed the
bacteria Bacteria (; : bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of Prokaryote, prokaryotic microorganisms. Typically a few micr ...
that form
dental plaque Dental plaque is a biofilm of microorganisms (mostly bacteria, but also fungi) that grows on surfaces within the mouth. It is a sticky colorless deposit at first, but when it forms Calculus (dental), tartar, it is often brown or pale yellow. It is ...
and cause
dental cavities Tooth decay, also known as caries,The word 'caries' is a mass noun, and is not a plural of 'carie'.'' is the breakdown of teeth due to acids produced by bacteria. The resulting cavities may be a number of different colors, from yellow to black ...
. As a
food additive Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives, such as vinegar ( pickling), salt ( salting), smoke ( smoking) and sugar ( crystallization), have been used f ...
, glycerol is labeled as
E number E numbers, short for Europe numbers, are codes for substances used as food additives, including those found naturally in many foods, such as vitamin C, for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly ...
E422. It is added to icing (frosting) to prevent it from setting too hard. As used in foods, glycerol is categorized by the U.S.
Academy of Nutrition and Dietetics The Academy of Nutrition and Dietetics is a multi-unit enterprise that includes a 501(c)(6) trade association in the United States. With over 112,000 members, the association claims to be the largest organization of food and nutrition professiona ...
as a
carbohydrate A carbohydrate () is a biomolecule composed of carbon (C), hydrogen (H), and oxygen (O) atoms. The typical hydrogen-to-oxygen atomic ratio is 2:1, analogous to that of water, and is represented by the empirical formula (where ''m'' and ''n'' ...
. The U.S.
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respo ...
(FDA) carbohydrate designation includes all caloric
macronutrient A nutrient is a substance used by an organism to survive, grow and reproduce. The requirement for dietary nutrient intake applies to animals, plants, fungi and protists. Nutrients can be incorporated into cells for metabolic purposes or excret ...
s excluding protein and fat. Glycerol has a caloric density similar to table sugar, but a lower
glycemic index The glycemic (glycaemic) index (GI; ) is a number from 0 to 100 assigned to a food, with pure glucose arbitrarily given the value of 100, which represents the relative rise in the blood glucose level two hours after consuming that food. The GI of ...
and different
metabolic pathway In biochemistry, a metabolic pathway is a linked series of chemical reactions occurring within a cell (biology), cell. The reactants, products, and Metabolic intermediate, intermediates of an enzymatic reaction are known as metabolites, which are ...
within the body. It is also recommended as an additive when polyol sweeteners such as
erythritol Erythritol (, ) is an organic compound, the naturally occurring achiral meso four-carbon sugar alcohol (or polyol). It is the reduced form of either D- or L- erythrose and one of the two reduced forms of erythrulose. It is used as a food ad ...
and
xylitol Xylitol is a chemical compound with the formula , or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular Stereoisomerism, stereoisomer with that structural formula. It is a colorless or white crystalline solid. It is classified as a polyalcoho ...
are used, as its heating effect in the mouth will counteract these sweeteners' cooling effect.


Medical

Glycerol is used in
medical Medicine is the science and Praxis (process), practice of caring for patients, managing the Medical diagnosis, diagnosis, prognosis, Preventive medicine, prevention, therapy, treatment, Palliative care, palliation of their injury or disease, ...
,
pharmaceutical Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the ...
and
personal care Personal care products are consumer products which are applied on various external parts of the body such as skin, hair, nails, lips, external genital and anal areas, as well as teeth and mucous membrane of the oral cavity, in order to make ...
preparations, often as a means of improving smoothness, providing
lubrication Lubrication is the process or technique of using a lubricant to reduce friction and wear and tear in a contact between two surfaces. The study of lubrication is a discipline in the field of tribology. Lubrication mechanisms such as fluid-lubr ...
, and as a
humectant A humectant is a hygroscopic (water-absorbing) substance used to keep things moist. They are used in many products, including food, cosmetics, medicines and pesticides. When used as a food additive, a humectant has the effect of keeping moistu ...
.
Ichthyosis Ichthyosis is a family of genetic disorder, genetic skin disorders characterized by Xeroderma, dry, Scleroderma, thickened, scaly skin. The more than 20 types of ichthyosis range in severity of symptoms, outward appearance, underlying genetic cau ...
and xerosis have been relieved by the topical use of glycerin. It is found in allergen
immunotherapies Immunotherapy or biological therapy is the treatment of disease by activating or suppressing the immune system. Immunotherapies designed to elicit or amplify an immune response are classified as ''activation immunotherapies,'' while immunotherap ...
,
cough syrup Cold medicines are a group of medications taken individually or in combination as a treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The term encompasses a broad array of drugs, including ana ...
s,
elixir An elixir is a sweet liquid used for medical purposes, to be taken orally and intended to cure one's illness. When used as a dosage form, pharmaceutical preparation, an elixir contains at least one active ingredient designed to be taken orall ...
s and
expectorant Mucoactive agents are a class of pharmacologic agents that include expectorants, mucolytics, mucoregulators, and mucokinetics that can affect the volume, viscosity, transportation, and composition of mucus or sputum. They often aid in clearing ...
s,
toothpaste Toothpaste is a paste or gel dentifrice that is used with a toothbrush to clean and maintain the aesthetics of Human tooth, teeth. Toothpaste is used to promote oral hygiene: it is an abrasive that aids in removing dental plaque and food from th ...
,
mouthwash Mouthwash, mouth rinse, oral rinse, or mouth bath is a liquid which is held in the mouth passively or swirled around the mouth by contraction of the perioral muscles and/or movement of the head, and may be gargled, where the head is tilted back ...
es,
skin care Skin care or skincare is the practice of maintaining and improving the health and appearance of the skin. It includes washing, moisturizing, protecting from the sun, and treating skin problems like acne and dryness. Skin care can help prevent i ...
products, shaving cream,
hair care Hair care or haircare is an overall term for hygiene and cosmetology involving the hair which grows from the human scalp, and to a lesser extent Facial hair, facial, Pubic hair, pubic and other body hair. Hair care routines differ according to a ...
products,
soap Soap is a salt (chemistry), salt of a fatty acid (sometimes other carboxylic acids) used for cleaning and lubricating products as well as other applications. In a domestic setting, soaps, specifically "toilet soaps", are surfactants usually u ...
s, and water-based
personal lubricant Personal lubricants (colloquially termed lube) are specialized lubricants used during sexual acts, such as intercourse and masturbation, to reduce friction to or between the penis and vagina, anus or other body parts, or applied to sex toys to ...
s. In solid dosage forms like tablets, glycerol is used as a tablet holding agent. For human consumption, glycerol is classified by the FDA among the
sugar alcohol Sugar alcohols (also called polyhydric alcohols, polyalcohols, alditols or glycitols) are organic compounds, typically derived from sugars, containing one hydroxyl group attached to each carbon atom. They are white, water-soluble solids that c ...
s as a caloric macronutrient. Glycerol is also used in
blood bank A blood bank is a center where blood gathered as a result of blood donation is stored and preserved for later use in blood transfusion. The term "blood bank" typically refers to a department of a hospital usually within a clinical pathology labora ...
ing to preserve
red blood cell Red blood cells (RBCs), referred to as erythrocytes (, with -''cyte'' translated as 'cell' in modern usage) in academia and medical publishing, also known as red cells, erythroid cells, and rarely haematids, are the most common type of blood cel ...
s prior to freezing. Taken rectally, glycerol functions as a
laxative Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation. Laxatives vary as to how they work and the side effects they may have. Certain stimulant, lubri ...
by irritating the anal mucosa and inducing a hyperosmotic effect, expanding the colon by drawing water into it to induce
peristalsis Peristalsis ( , ) is a type of intestinal motility, characterized by symmetry in biology#Radial symmetry, radially symmetrical contraction and relaxation of muscles that propagate in a wave down a tube, in an wikt:anterograde, anterograde dir ...
resulting in evacuation. It may be administered undiluted either as a
suppository A suppository is a dosage form used to deliver pharmaceutical drug, medications by insertion into a body orifice (any opening in the body), where it dissolves or melts to exert local or systemic effects. There are three types of suppositories, eac ...
or as a small-volume (2–10 ml)
enema An enema, also known as a clyster, is the rectal administration of a fluid by injection into the Large intestine, lower bowel via the anus.Cullingworth, ''A Manual of Nursing, Medical and Surgical'':155 The word ''enema'' can also refer to the ...
. Alternatively, it may be administered in a dilute solution, such as 5%, as a high-volume enema. Taken orally (often mixed with fruit juice to reduce its sweet taste), glycerol can cause a rapid, temporary decrease in the internal pressure of the eye. This can be useful for the initial emergency treatment of severely elevated eye pressure. In 2017, researchers showed that the probiotic '' Limosilactobacillus reuteri'' bacteria can be supplemented with glycerol to enhance its production of antimicrobial substances in the human gut. This was confirmed to be as effective as the antibiotic
vancomycin Vancomycin is a glycopeptide antibiotic medication used to treat certain bacterial infections. It is administered intravenously ( injection into a vein) to treat complicated skin infections, bloodstream infections, endocarditis, bone an ...
at inhibiting ''
Clostridioides difficile ''Clostridioides difficile'' ( syn. ''Clostridium difficile'') is a bacterium known for causing serious diarrheal infections, and may also cause colon cancer. It is known also as ''C. difficile'', or ''C. diff'' (), and is a Gram-positive spec ...
'' infection without having a significant effect on the overall microbial composition of the gut. Glycerol has also been incorporated as a component of bio-ink formulations in the field of bioprinting. The glycerol content acts to add viscosity to the bio-ink without adding large protein, saccharide, or glycoprotein molecules.


Botanical extracts

When utilized in tincture method extractions, specifically as a 10% solution, glycerol prevents tannins from precipitating in ethanol extracts of plants (
tincture A tincture is typically an extract of plant or animal material dissolved in ethanol (ethyl alcohol). Solvent concentrations of 25–60% are common, but may run as high as 90%.Groot Handboek Geneeskrachtige Planten by Geert Verhelst In chemistr ...
s). It is also used as an "alcohol-free" alternative to ethanol as a solvent in preparing herbal extractions. It is less extractive when utilized in a standard tincture methodology. Alcohol-based tinctures can also have the alcohol removed and replaced with glycerol for its preserving properties. Such products are not "alcohol-free" in a scientific or FDA regulatory sense, as glycerol contains three hydroxyl groups. Fluid extract manufacturers often extract herbs in hot water before adding glycerol to make glycerites. When used as a primary "true" alcohol-free botanical extraction solvent in non-tincture based methodologies, glycerol has been shown to possess a high degree of extractive versatility for botanicals including removal of numerous constituents and complex compounds, with an extractive power that can rival that of alcohol and water–alcohol solutions. That glycerol possesses such high extractive power assumes it is utilized with dynamic (critical) methodologies as opposed to standard passive "tincturing" methodologies that are better suited to alcohol. Glycerol does not denature or render a botanical's constituents inert as alcohols (
ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
,
methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...
, and so on) do. Glycerol is a stable preserving agent for botanical extracts that, when utilized in proper concentrations in an extraction solvent base, does not allow inverting or reduction-oxidation of a finished extract's constituents, even over several years. Both glycerol and ethanol are viable preserving agents. Glycerol is
bacteriostatic A bacteriostatic agent or bacteriostat, abbreviated Bstatic, is a biological or chemical agent that stops bacteria from reproducing, while not necessarily killing them otherwise. Depending on their application, bacteriostatic antibiotics, disinfec ...
in its action, and ethanol is bactericidal in its action.


Electronic cigarette liquid

Glycerin, along with
propylene glycol Propylene glycol ( IUPAC name: propane-1,2-diol) is a viscous, colorless liquid. It is almost odorless and has a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. As it contains two alcohol groups, it is classified as a diol. An al ...
, is a common component of
e-liquid An electronic cigarette is a handheld battery-powered vaporizer that simulates smoking, but without tobacco combustion. E-cigarette components include a mouthpiece (drip tip), a cartridge (liquid storage area), a heating element/ atomizer, a m ...
, a solution used with electronic vaporizers (
electronic cigarettes An electronic cigarette (e-cigarette), or vape, is a device that simulates smoking. It consists of an Construction of electronic cigarettes#Atomizer and tank, atomizer, a power source such as a battery, and a container such as a cartridge or ...
). This glycerol is heated with an atomizer (a heating coil often made of Kanthal wire), producing the
aerosol An aerosol is a suspension (chemistry), suspension of fine solid particles or liquid Drop (liquid), droplets in air or another gas. Aerosols can be generated from natural or Human impact on the environment, human causes. The term ''aerosol'' co ...
that delivers
nicotine Nicotine is a natural product, naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and ''Duboisia hopwoodii'') and is widely used recreational drug use, recreationally as a stimulant and anxiolytic. As ...
to the user.


Antifreeze

Like
ethylene glycol Ethylene glycol ( IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odo ...
and propylene glycol, glycerol is a non-ionic kosmotrope that forms strong hydrogen bonds with water molecules, competing with water-water
hydrogen bonds In chemistry, a hydrogen bond (H-bond) is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as a purely electrostatic force. It occurs when a hydrogen (H) atom, covalently bonded to a mo ...
. This interaction disrupts the formation of ice. The minimum freezing point temperature is about corresponding to 70% glycerol in water. Glycerol was historically used as an anti-freeze for automotive applications before being replaced by ethylene glycol, which has a lower freezing point. While the minimum freezing point of a glycerol-water mixture is higher than an ethylene glycol-water mixture, glycerol is not toxic and is being re-examined for use in automotive applications. In the laboratory, glycerol is a common component of solvents for
enzymatic An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as produc ...
reagents In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
stored at temperatures below due to the depression of the freezing temperature. It is also used as a
cryoprotectant A cryoprotectant is a substance used to protect biological tissue from freezing damage (i.e. that due to ice formation). Arctic and Antarctic insects, fish and amphibians create cryoprotectants ( antifreeze compounds and antifreeze proteins) in th ...
where the glycerol is dissolved in water to reduce damage by ice crystals to laboratory organisms that are stored in frozen solutions, such as
fungi A fungus (: fungi , , , or ; or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and mold (fungus), molds, as well as the more familiar mushrooms. These organisms are classified as one ...
,
bacteria Bacteria (; : bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of Prokaryote, prokaryotic microorganisms. Typically a few micr ...
,
nematode The nematodes ( or ; ; ), roundworms or eelworms constitute the phylum Nematoda. Species in the phylum inhabit a broad range of environments. Most species are free-living, feeding on microorganisms, but many are parasitic. Parasitic worms (h ...
s, and mammalian embryos. Some organisms like the
moor frog The moor frog (''Rana arvalis'') is a slim, reddish-brown, semiaquatic amphibian native to Europe and Asia. Moor frogs are known for their ability to freeze solid and survive thawing. The frog makes use of various cryoprotectants i.e. Antifreeze ...
produce glycerol to survive freezing temperatures during hibernation.


Chemical intermediate

Glycerol is used to produce a variety of useful derivatives.
Nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between Alcohol ...
gives
nitroglycerin Nitroglycerin (NG) (alternative spelling nitroglycerine), also known as trinitroglycerol (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless or pale yellow, oily, explosive liquid most commonly produced by ...
, an essential ingredient of various explosives such as
dynamite Dynamite is an explosive made of nitroglycerin, sorbents (such as powdered shells or clay), and Stabilizer (chemistry), stabilizers. It was invented by the Swedish people, Swedish chemist and engineer Alfred Nobel in Geesthacht, Northern German ...
,
gelignite Gelignite (), also known as blasting gelatin or simply "jelly", is an explosive material consisting of collodion-cotton (a type of nitrocellulose or guncotton) dissolved in either nitroglycerine or nitroglycol and mixed with wood pulp and Potassi ...
, and propellants like
cordite Cordite is a family of smokeless propellants developed and produced in Britain since 1889 to replace black powder as a military firearm propellant. Like modern gunpowder, cordite is classified as a low explosive because of its slow burni ...
. Nitroglycerin under the name glyceryl trinitrate (GTN) is commonly used to relieve
angina pectoris Angina, also known as angina pectoris, is chest pain or pressure, usually caused by insufficient blood flow to the heart muscle (myocardium). It is most commonly a symptom of coronary artery disease. Angina is typically the result of part ...
, taken in the form of sub-lingual tablets, patches, or as an
aerosol An aerosol is a suspension (chemistry), suspension of fine solid particles or liquid Drop (liquid), droplets in air or another gas. Aerosols can be generated from natural or Human impact on the environment, human causes. The term ''aerosol'' co ...
spray. Trifunctional polyether polyols are produced from glycerol and
propylene oxide Propylene oxide is an epoxide with the molecular formula C3H6O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols f ...
. Oxidation of glycerol affords
mesoxalic acid Mesoxalic acid, also called oxomalonic acid or ketomalonic acid, is an organic compound with formula C3H2O5 or HO−(C=O)3−OH. Mesoxalic acid is both a dicarboxylic acid and a ketonic acid. It readily loses two protons to yield the divalent an ...
. Dehydrating glycerol affords hydroxyacetone. Chlorination of glycerol gives the 1-chloropropane-2,3-diol: : The same compound can be produced by hydrolysis of epichlorohydrin. Epoxidation by reaction with
epichlorohydrin Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscibility, miscible with most p ...
and a
Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any ...
yields Glycerol triglycidyl ether.


Vibration damping

Glycerol is used as fill for
pressure gauge Pressure measurement is the measurement of an applied force by a fluid (liquid or gas) on a surface. Pressure is typically measured in units of force per unit of surface area. Many techniques have been developed for the measurement of press ...
s to damp vibration. External vibrations, from compressors, engines, pumps, etc., produce
harmonic In physics, acoustics, and telecommunications, a harmonic is a sinusoidal wave with a frequency that is a positive integer multiple of the ''fundamental frequency'' of a periodic signal. The fundamental frequency is also called the ''1st har ...
vibrations within
Bourdon gauge Pressure measurement is the measurement of an applied force by a fluid (liquid or gas) on a surface. Pressure is typically measured in unit of measurement, units of force per unit of surface area. Many techniques have been developed for the me ...
s that can cause the needle to move excessively, giving inaccurate readings. The excessive swinging of the needle can also damage internal gears or other components, causing premature wear. Glycerol, when poured into a gauge to replace the air space, reduces the harmonic vibrations that are transmitted to the needle, increasing the lifetime and reliability of the gauge.


Niche uses


Entertainment industry

Glycerol is used by set decorators when filming scenes involving water to prevent an area meant to look wet from drying out too quickly. Glycerine is also used in the generation of
theatrical smoke and fog Theatrical smoke and fog, also known as special effect smoke, fog or haze, is a category of atmospheric effects used in the entertainment industry. The use of fogs can be found throughout motion picture and television productions, live theatre, con ...
as a component of the fluid used in
fog machine A fog machine, fog generator, or smoke machine is a device that emits a dense vapor that appears similar to fog or smoke. This artificial fog is most commonly used in professional entertainment applications, but smaller, more affordable fog mac ...
s as a replacement for
glycol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting gro ...
, which has been shown to be an irritant if exposure is prolonged.


Ultrasonic couplant

Glycerol can be sometimes used as replacement for water in
ultrasonic testing Ultrasonic testing (UT) is a family of non-destructive testing techniques based on the propagation of ultrasonic waves in the object or material tested. In most common UT applications, very short ultrasonic pulse waves with centre frequencie ...
, as it has favourably higher
acoustic impedance Acoustic impedance and specific acoustic impedance are measures of the opposition that a system presents to the acoustic flow resulting from an acoustic pressure applied to the system. The International System of Units, SI unit of acoustic impeda ...
(2.42 MRayl versus 1.483 MRayl for water) while being relatively safe, non-toxic, non-corrosive and relatively low cost.


Internal combustion fuel

Glycerol is also used to power diesel generators supplying electricity for the FIA
Formula E Formula E, officially the ABB FIA Formula E World Championship, is an open-wheel single-seater motorsport championship for electric cars. The racing series is the highest class of competition for electrically powered single-seater racing cars ...
series of electric race cars.


Research on additional uses

Research continues into potential
value-added Value added is a term in economics for calculating the difference between market value of a product or service, and the sum value of its constituents. It is relatively expressed by the demand curve, supply-demand curve for specific units of sale. ...
products of glycerol obtained from biodiesel production. Examples (aside from combustion of waste glycerol): *
Hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...
gas Gas is a state of matter that has neither a fixed volume nor a fixed shape and is a compressible fluid. A ''pure gas'' is made up of individual atoms (e.g. a noble gas like neon) or molecules of either a single type of atom ( elements such as ...
production. * Glycerine acetate is a potential fuel additive. * Additive for
starch Starch or amylum is a polymeric carbohydrate consisting of numerous glucose units joined by glycosidic bonds. This polysaccharide is produced by most green plants for energy storage. Worldwide, it is the most common carbohydrate in human diet ...
thermoplastic. * Conversion to various other chemicals: **
Propylene glycol Propylene glycol ( IUPAC name: propane-1,2-diol) is a viscous, colorless liquid. It is almost odorless and has a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. As it contains two alcohol groups, it is classified as a diol. An al ...
**
Acrolein Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat ...
**
Ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
**
Epichlorohydrin Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscibility, miscible with most p ...
, a raw material for
epoxy resins Epoxy is the family of basic components or Curing (chemistry), cured end products of epoxy Resin, resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide fun ...


Metabolism

Glycerol is a precursor for synthesis of
triacylglycerol A triglyceride (from ''tri-'' and '' glyceride''; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates as ...
s and of
phospholipid Phospholipids are a class of lipids whose molecule has a hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue (usually a glycerol molecule). Marine phospholipids typ ...
s in the liver and
adipose tissue Adipose tissue (also known as body fat or simply fat) is a loose connective tissue composed mostly of adipocytes. It also contains the stromal vascular fraction (SVF) of cells including preadipocytes, fibroblasts, Blood vessel, vascular endothel ...
. When the body uses stored fat as a source of energy, glycerol and
fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...
s are released into the bloodstream. Glycerol is mainly metabolized in the liver. Glycerol injections can be used as a simple test for liver damage, as its rate of absorption by the liver is considered an accurate measure of liver health. Glycerol metabolism is reduced in both cirrhosis and
fatty liver disease Fatty liver disease (FLD), also known as hepatic steatosis and steatotic liver disease (SLD), is a condition where excess fat builds up in the liver. Often there are no or few symptoms. Occasionally there may be tiredness or pain in the upper r ...
. Blood glycerol levels are highly elevated during
diabetes Diabetes mellitus, commonly known as diabetes, is a group of common endocrine diseases characterized by sustained high blood sugar levels. Diabetes is due to either the pancreas not producing enough of the hormone insulin, or the cells of th ...
, and is believed to be the cause of reduced fertility in patients who suffer from diabetes and metabolic syndrome. Blood glycerol levels in diabetic patients average three times higher than healthy controls. Direct glycerol treatment of testes has been found to cause significant long-term reduction in sperm count. Further testing on this subject was abandoned due to the unexpected results, as this was not the goal of the experiment. Circulating glycerol does not glycate proteins as do
glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...
or fructose, and does not lead to the formation of advanced glycation endproducts (AGEs). In some organisms, the glycerol component can enter the
glycolysis Glycolysis is the metabolic pathway that converts glucose () into pyruvic acid, pyruvate and, in most organisms, occurs in the liquid part of cells (the cytosol). The Thermodynamic free energy, free energy released in this process is used to form ...
pathway directly and, thus, provide energy for cellular metabolism (or, potentially, be converted to glucose through
gluconeogenesis Gluconeogenesis (GNG) is a metabolic pathway that results in the biosynthesis of glucose from certain non-carbohydrate carbon substrates. It is a ubiquitous process, present in plants, animals, fungi, bacteria, and other microorganisms. In verte ...
). Before glycerol can enter the pathway of glycolysis or gluconeogenesis (depending on physiological conditions), it must be converted to their intermediate
glyceraldehyde 3-phosphate Glyceraldehyde 3-phosphate, also known as triose phosphate or 3-phosphoglyceraldehyde and abbreviated as G3P, GA3P, GADP, GAP, TP, GALP or PGAL, is a metabolite that occurs as an intermediate in several central pathways of all organisms.Nelson, D ...
in the following steps:
The enzyme glycerol kinase is present mainly in the liver and kidneys, but also in other body tissues, including muscle and brain. In adipose tissue, glycerol 3-phosphate is obtained from
dihydroxyacetone phosphate Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is the anion with the formula HOCH2C(O)CH2OPO32-. This anion is involved in many metabolic pathways, including the Calvin cycle in plants and glycolysis.Nelson, D. L.; Co ...
with the enzyme
glycerol-3-phosphate dehydrogenase Glycerol-3-phosphate dehydrogenase (GPDH) is an enzyme that catalyzes the reversible redox conversion of dihydroxyacetone phosphate (a.k.a. glycerone phosphate, outdated) to sn-glycerol 3-phosphate. Glycerol-3-phosphate dehydrogenase serves a ...
.


Toxicity and safety

Glycerol has very low toxicity when ingested; its LD50 oral dose for rats is 12600 mg/kg and 8700 mg/kg for mice. It does not appear to cause toxicity when inhaled, although changes in cell maturity occurred in small sections of lung in animals under the highest dose measured. A sub-chronic 90-day nose-only inhalation study in
Sprague Dawley Laboratory rats or lab rats are strains of the rat subspecies '' Rattus norvegicus domestica'' (Domestic Norwegian rat) which are bred and kept for scientific research. While less commonly used for research than laboratory mice, rats have ser ...
rats exposed to 0.03, 0.16 and 0.66 mg of glycerin per liter of air for 6-hour continuous sessions revealed no treatment-related toxicity other than minimal
metaplasia Metaplasia () is the transformation of a cell type to another cell type. The change from one type of cell to another may be part of a normal maturation process, or caused by some sort of abnormal stimulus. In simplistic terms, it is as if the ...
of the
epithelium Epithelium or epithelial tissue is a thin, continuous, protective layer of cells with little extracellular matrix. An example is the epidermis, the outermost layer of the skin. Epithelial ( mesothelial) tissues line the outer surfaces of man ...
lining at the base of the
epiglottis The epiglottis (: epiglottises or epiglottides) is a leaf-shaped flap in the throat that prevents food and water from entering the trachea and the lungs. It stays open during breathing, allowing air into the larynx. During swallowing, it closes ...
in rats exposed to 0.66 mg/L glycerin.


Glycerol intoxication

Excessive consumption by children can lead to glycerol intoxication. Symptoms of intoxication include
hypoglycemia Hypoglycemia (American English), also spelled hypoglycaemia or hypoglycæmia (British English), sometimes called low blood sugar, is a fall in blood sugar to levels below normal, typically below 70 mg/dL (3.9 mmol/L). Whipple's tria ...
,
nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...
and a
loss of consciousness Unconsciousness is a state in which a living individual exhibits a complete, or near-complete, inability to maintain an awareness of self and environment or to respond to any human or environmental stimulus. Unconsciousness may occur as the re ...
. While intoxication as a result of excessive glycerol consumption is rare and its symptoms generally mild, occasional reports of hospitalization have occurred. In the United Kingdom in August 2023, manufacturers of syrup used in slush ice drinks were advised to reduce the amount of glycerol in their formulations by the
Food Standards Agency The Food Standards Agency is a non-ministerial government department of the Government of the United Kingdom. It is responsible for protecting public health in relation to food in England, Wales and Northern Ireland. It is led by a board appoin ...
to reduce the risk of intoxication. A 2025 study reported that between 2018 and 2024, at least 21 children aged 2–7 in the UK and Ireland received emergency treatment for symptoms of glycerol intoxication following the consumption of slush ice drinks.
Food Standards Scotland Food Standards Scotland () is a non-ministerial government department of the Scottish Government. It is responsible for food safety, food standards, nutrition, food labelling and meat inspection in Scotland. Established by the Food (Scotland) ...
advises that slush ice drinks containing glycerol should not be given to children under the age of 4, owing to the risk of intoxication. It also recommends that businesses do not use
free refill Free refills occur when a drink's receptacle, usually that of a soft drink, tea or coffee, is allowed to be filled again by its purchaser, free of charge, after they have consumed the drink. Occasionally the glass or cup holding the drink is not ...
offers for the drinks in venues where children under the age of 10 are likely to consume them, and that products should be appropriately labelled to inform consumers of the presence of glycerol.


Historical cases of contamination with diethylene glycol

On 4 May 2007, the FDA advised all U.S. makers of medicines to test all batches of glycerol for
diethylene glycol Diethylene glycol (DEG) is an organic compound with the formula (HOCH2CH2)2O. It is a colorless, practically odorless, and hygroscopic liquid with a sweetish taste. It is a four carbon Dimer (chemistry), dimer of ethylene glycol. It is miscible in ...
contamination. This followed an occurrence of hundreds of fatal poisonings in Panama resulting from a falsified import customs declaration by Panamanian import/export firm Aduanas Javier de Gracia Express, S. A. The cheaper diethylene glycol was relabeled as the more expensive glycerol. Between 1990 and 1998, incidents of DEG poisoning reportedly occurred in Argentina, Bangladesh, India, and Nigeria, and resulted in hundreds of deaths. In 1937, more than one hundred people died in the United States after ingesting DEG-contaminated
elixir sulfanilamide Elixir sulfanilamide was an improperly prepared sulfonamide (medicine), sulfonamide antibiotic that caused mass poisoning in the United States in 1937. It is believed to have killed 107 people. The public outcry caused by this incident and other s ...
, a drug used to treat infections.


Etymology

The origin of the ''gly-'' and ''glu''- prefixes for
glycol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting gro ...
s and sugars is from
Ancient Greek Ancient Greek (, ; ) includes the forms of the Greek language used in ancient Greece and the classical antiquity, ancient world from around 1500 BC to 300 BC. It is often roughly divided into the following periods: Mycenaean Greek (), Greek ...
''glukus'' which means sweet. Name ''glycérine'' was coined ca. 1811 by
Michel Eugène Chevreul Michel Eugène Chevreul (; 31 August 1786 – 9 April 1889) was a French chemist whose work contributed to significant developments in science, medicine, and art. Chevreul's early work with animal fats revolutionized soap and candle manufacturing ...
to denote what was previously called "sweet principle of fat" by its discoverer
Carl Wilhelm Scheele Carl Wilhelm Scheele (, ; 9 December 1742 – 21 May 1786) was a Swedish Pomerania, German-Swedish pharmaceutical chemist. Scheele discovered oxygen (although Joseph Priestley published his findings first), and identified the elements molybd ...
. It was borrowed into English ca. 1838 and in the 20th c. displaced by 1872 term glycerol featuring an alcohols' suffix -ol.


Properties

Table of thermal and physical properties of saturated liquid glycerin: :


See also

*
Dioxalin Dioxalin is a reaction product of glycerol with oxalic acid at 533 Kelvin, K. Its IUPAC nomenclature, IUPAC name is 5-(hydroxymethyl)-1,4-dioxane-2,3-dione. Dioxalin readily loses two molecules of carbon dioxide at this high temperature to form ...
*
Epichlorohydrin Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscibility, miscible with most p ...
*
Nitroglycerin Nitroglycerin (NG) (alternative spelling nitroglycerine), also known as trinitroglycerol (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless or pale yellow, oily, explosive liquid most commonly produced by ...
*
Oleochemical Oleochemistry is the study of vegetable oils and animal oils and fats, and oleochemicals derived from these fats and oils. The resulting product can be called oleochemicals (from Latin: oleum "olive oil"). The major product of this industry is so ...
s *
Saponification Saponification is a process of cleaving esters into carboxylate salts and Alcohol (chemistry), alcohols by the action of aqueous alkali. Typically aqueous sodium hydroxide solutions are used. It is an important type of alkaline hydrolysis. When the ...
/ Soapmaking * Solketal *
Transesterification Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. Strong acids catalyze the r ...


References


External links


Mass spectrum of glycerol


{{Authority control Alcohol solvents Biofuels Commodity chemicals Cosmetics chemicals Demulcents E-number additives Food additives Glassforming liquids and melts Household chemicals Laxatives Sugar alcohols Triols By-products