Glycerol
FromWikipedia, the free encyclopaedia
"Glycerine"and "Glycerin"
Glycerol |
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IUPAC name propane-1,2,3-triol |
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Other names: glycerine, glycerine, propanetriol
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Identifiers |
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CAS number |
56-81-5 |
Pub Chem |
753 |
ChemSpider |
733 |
UNII |
PDC6A3C0OX |
Drug Bank |
DB04077 |
KEGG |
D00028 |
ChEBI |
CHEBI:17522 |
ChEMBL |
CHEMBL692 |
ATC code |
A06AG04, A06AX01, QA16QA03 |
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Properties |
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Molecular formula |
C3H8O3 |
Molar mass |
92.09 g mol−1 |
Appearance |
colourless liquid |
Odour |
odourless |
Density |
1.261 g/cm3 |
Melting point |
17.8 °C, 291 K, 64 °F |
Boiling point |
290 °C, 563 K, 554 °F |
Refractive index (nD) |
1.4746 |
Viscosity |
1.412 Pa·s |
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Hazards |
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MSDS |
External MSDS |
NFPA 704 |
1 1 0 |
Flash point |
160 °C (320 °F) (closed cup) |
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Supplementary data page |
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Structure and |
n, εr, etc. |
Thermodynamic |
Phase behaviour |
Spectral data |
UV, IR, NMR, MS |
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Glycerol (or glycerine, glycerin)is a simple polyol compound.
It is a colourless,odourless, viscous liquid that is widely used in pharmaceutical formulations.
Glycerolhas three hydroxyl groupsthat are responsible for its solubility in water and its hygroscopicnature.
The glycerol backbone is central to all lipids known as triglycerides.
Glycerolis sweet-tasting and of low toxicity.
Production
Approximately 950,000 tons per annum are produced in the USA and Europe; 350,000 tons of glycerol were produced per year in the United States alone from 2000–2004.
Productionwill increase as the EU directive 2003/30/EC is implemented, which requires the replacement of 5.75% of petroleum fuels with bio fuel across all Member Statesby 2010, as glycerol is a byproduct in the production of biodiesel.
It isprojected that by the year 2020, production will be six times more than demand.
From fats and oils
Triglycerides found in fats and oils are by definition esters of glycerol with long-chaincarboxylic acids; the hydrolysis (saponification) or transesterification of these triglycerides produces stoichiometric quantities of glycerol.
In this scheme, glycerol is produced as a co-product in the production of long-chaincarboxylate salts used as soaps
It is also a by product of the production of biodiesel via transesterification.
This form of crude glycerin is often dark in appearance with a thick, syrup-like consistency. Triglycerides (1) are treated with an alcohol such as ethanol (2) with catalytic base to give ethyl esters of fatty acids (3)and glycerol (4):
Glycerol from triglycerides is produced on a large scale, but the crude product is of variable quality, with a low selling price of as low as 1-8 U.S. cents perpound in 2011.
It can bepurified, but the process is expensive.
As a result, a good fraction of crude glycerol is disposed of as waste.
Some glycerol is burned for energy, but the heat value is low.
That said, crude glycerol from the hydrolysis of triglycerides can be purified by treatment with activated carbon to remove organic impurities, alkali to remove un-reacted glycerol esters, and ion exchange to remove salts.
High purity glycerol (> 99.5%) is obtained by multi-step distillation; vacuum is helpful due to the high boiling point of glycerol (290 °C).
Synthetic glycerol
Synthetic glycerol refers to material obtained from non-triglyceride sources.
Glycerol may also be produced by various routes from propylene.
The epichlorohydrin process is the most important; it involves the chlorination of propylene to give allyl chloride, which is oxidized with hypochlorite to dichlorohydrins, which reacts with a strong base to give epichlorohydrin.
Epichlorohydrinis then hydrolyzed to give glycerol.
Chlorine-free processes from propylene include the synthesis of glycerol from acrolein and propyleneoxide.
Because of the emphasis on biodiesel, where glycerol is a waste product, the market for glycerol is depressed, and these old processes are no longer economical on a large scale.
In fact, due to the glycerol glut, efforts are being made to convert glycerol to its precursors, such as acrolein and epichlorohydrin.
Applications
Food industry
In foods and beverages, glycerol serves as a humectant, solvent, and sweetener, and may help preserve foods.
It is also used as filler in commercially prepared low-fat foods (e.g biscuits) and as a thickening agent in liqueurs.
Glycerol and water are used to preserve certain types of leaves.
As a sugar substitute, it has approximately 27 kilocalories per teaspoon (sugar has 20) and is 60% as sweet as sucrose.
It does not feed the bacteria that form plaques and cause dental cavities.
As a food additive, glycerol is labeled as E number E422.
As used in foods, glycerol is categorized by the American Dietetic Association as a carbohydrate.
The U.S. Food and Drug Administration (FDA) carbohydrate designation includes all caloric macronutrients excluding protein and fat.
Glycerol has a caloric density similar to table sugar, but a lower glycemic index and different metabolic pathway within the body, so some dietary advocates accept glycerol as a sweetener compatible with low carbohydrate diets.
Pharmaceutical and personal care applications
Glycerol suppositories used as laxatives
Glycerolis used in medical and pharmaceutical and personal care preparations, mainly a sa means of improving smoothness, providing lubrication and as a humectant.
It is found in allergen immune therapies, cough syrups, elixirs and expectorants, toothpaste, mouth washes, skin care products, shaving cream, hair care products, soaps and water based personal lubricants.
In solid dosage forms like tablets, glycerol is used as a tablet holding agent.
For human consumption, glycerol is classified by the U.S. FDA among the sugar alcohols asa caloric macronutrient.
Glycerolis a component of glycerin soap.
Essential oils are added for fragrance.
This kind of soap is used by people with sensitive, easily irritated skin because it prevents skin dryness with its moisturizing properties.
It draws moisture up through skin layers and slows or prevents excessive drying and evaporation.[citation needed]
With similar benefits, glycerin is a common ingredient in many bath salts recipes.
However, some assert that due to glycerin's moisture absorbing properties, it can be more of a hindrance than a benefit.
Glycerol can be used as a laxative when introduced into the rectum in suppository or small-volume (2–10 ml) (enema) form; it irritates the anal mucosa andinduces a hyperosmotic effect
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 a useful initial emergency treatment of severely elevated eye pressure.
Botanical extracts
When utilized in 'tincture' method extractions, specifically as a 10% solution, glycerol prevents tannins from precipitating in ethanol extracts of plants (tinctures).
It is also used as an 'alcohol-free' alternative to ethanol as a solvent in preparing herbal extractions.
It isless extractive when utilized in a standard tincture methodology.
Glycerol is approximately 30% more slowly absorbed by the body resulting in a much lower glycemic load.
Alcohol based tinctures can also have the alcohol removed and replaced with glycerol for its preserving properties.
Such products are not 'alcohol-free' in either a scientific or consumable sense, but should in all instances more accurately be referred to as"Alcohol Removed" products.
Fluid extract manufacturers often extract herbs in hot water before adding glycerin to make glycerites.
When used as a primary 'true' alcohol free (e.g.no alcohol, i.e. ethanol) ever being used) botanical extraction solvent in innovative non tincture based 'dynamic' methodologies, glycerol has been shown, both in literature and through extraction applications, 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 possess.
Such high extractive power assumes that glycerol, with its tri-atomic structure, is utilized with dynamic methodologies as opposed to standard passive 'tincturing' methodologies that are better suited to alcohol's di-atomic structure.
Glycerol possesses the intrinsic property of not denaturing or rendering a botanical's constituents inert (as di-atomic alcohols, i.e. ethanolic (grain) alcohol,methanolic (wood) alcohol, etc., do).
Glycerolis a stable preserving agent for botanical extracts that, when utilized inproper 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 in its action, and ethanol is bactericidal in its action.
Antifreeze
Like ethylene glycol and propylene glycol, glycerol is a non-ionic kosmotrope that forms strong hydrogen bonds with water molecules, competing with water-water hydrogen bonds.
This disrupts the crystal lattice formation of ice unless the temperature is significantly lowered.
The minimum freezing point temperature is at about −36 °F / −37.8 °C 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 reagents stored at temperatures below 0 °C due to the depression of the freezing temperature of solutions with high concentrations of glycerol.
It is also used as a cryoprotectant where the glycerol is dissolved in water to reduce damage by ice crystals to laboratory organisms that are stored in frozen solutions, such as bacteria, nematodes, and mammalian embryos.
Chemical intermediate
Glycerol is used to produce nitroglycerin, which is an essential ingredient of various explosives such as dynamite, gelignite, and propellants like cordite.
Reliance on soap making to supply co-product, glycerine made it difficult to increase production to meet wartime demand.
Hence, synthetic glycerin processes were national defense priorities in the days leading up to World War II. Nitroglycerin, also known as glyceryl trinitrate(GTN) is commonly used to relieve angina pectoris, taken in the form of sub-lingual tablets, or as an aerosol spray.
A great deal of research is being conducted to try to make value-added products from crude glycerol (typically containing 20% water and residual esterification catalyst) obtained from biodiesel production.
The use of crude glycerin as an additive tobiomass for a renewable energy source when combusted or gasified is also beingexplored.
Metabolism