Glycerol

| Ball-and-stick model of glycerol | Space-filling model of glycerol

|

Names
Preferred IUPAC name

Propane-1,2,3-triol[1]

Other names

Glycerin
Glycerine
1,2,3-Trioxypropane
1,2,3-Trihydroxypropane
1,2,3-Propanetriol

Identifiers

CAS Number

* 56-81-5 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:17754 Y

ChEMBL |

* ChEMBL692 Y

ChemSpider |

* 733 Y

DrugBank |

* DB04077 Y

IUPHAR/BPS

* 5195

KEGG |

* D00028 Y

PubChem CID

* 753

UNII |

* PDC6A3C0OX Y

InChI

* InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2 Y

Key: PEDCQBHIVMGVHV-UHFFFAOYSA-N Y

* InChI=1/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2

Key: PEDCQBHIVMGVHV-UHFFFAOYAF

SMILES

* OCC(O)CO

Properties

Chemical formula

| C3H8O3
Molar mass | 92.094 g·mol−1
Appearance  | Colorless hygroscopic liquid
Odor | Odorless
Density | 1.261 g/cm3
Melting point |  17.8 °C (64.0 °F; 290.9 K)
Boiling point |  290 °C (554 °F; 563 K)[5]

Solubility in water

| miscible[2]
log P | −2.32[3]
Vapor pressure | 0.003 mmHg (0.40 Pa) at 50 °C[2]

Magnetic susceptibility (χ)

| −57.06×10−6 cm3/mol

Refractive index (nD)

| 1.4746
Viscosity | 1.412 Pa·s (20 °C)[4]
Pharmacology
1=ATC code }}  | A06AG04 (WHO) A06AX01 (WHO), QA16QA03 (WHO)
Hazards
Safety data sheet | JT Baker ver. 2008 archive
NFPA 704 (fire diamond)  |

Flash point | 160 °C (320 °F; 433 K) (closed cup)
176 °C (349 °F; 449 K) (open cup)
NIOSH (US health exposure limits):

PEL (Permissible)

| TWA 15 mg/m3 (total)
TWA 5 mg/m3 (resp)[2]

REL (Recommended)

| None established[2]

IDLH (Immediate danger)

| N.D.[2]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Glycerol (/ˈɡlɪsərɒl/),[6] also called glycerine or glycerin, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known as glycerides. Because it has antimicrobial and antiviral properties, it is widely used in wound and burn treatments approved by the U.S. Food and Drug Administration. Conversely, it is also used as a bacterial culture medium.[7] Its presence in blood can be used as an effective marker to measure liver disease. It is also widely used as a sweetener in the food industry and as a humectant in pharmaceutical formulations. Because of its three hydroxyl groups, glycerol is miscible with water and is hygroscopic in nature.[8]

## Contents

* 1 Structure
* 2 Production
* 2.1 Synthetic glycerol
* 3 Applications
* 3.1 Food industry
* 3.2 Medical, pharmaceutical and personal care applications
* 3.3 Botanical extracts
* 3.4 Electronic cigarette liquid
* 3.5 Antifreeze
* 3.6 Chemical intermediate
* 3.7 Vibration damping
* 3.8 Niche uses
* 3.8.1 Entertainment industry
* 3.8.2 Ultrasonic couplant
* 3.9 Internal combustion fuel
* 3.10 Research on additional uses
* 4 Metabolism
* 5 Historical cases of contamination with diethylene glycol
* 6 Etymology
* 7 Properties
* 8 See also
* 9 References
* 10 External links

## Structure

Although achiral, glycerol is prochiral with respect to reactions of one of the two primary alcohols. Thus, in substituted derivatives, the stereospecific numbering labels the molecule with a sn\- prefix before the stem name of the molecule.[9][10][11]

## Production

Glycerol is generally obtained from plant and animal sources where it occurs in triglycerides, esters of glycerol with long-chain carboxylic acids. The hydrolysis, saponification, or transesterification of these triglycerides produces glycerol as well as the fatty acid derivative:

Triglyceride

3 NaOH / H

3 × soap

3 ×

glycerol

Triglycerides can be saponified with sodium hydroxide to give glycerol and fatty sodium salt or soap.

Typical plant sources include soybeans or palm. Animal-derived tallow is another source. Approximately 950,000 tons per year are produced in the United States and Europe; 350,000 tons of glycerol were produced per year in the U.S. alone from 2000 to 2004.[12] The EU directive 2003/30/EC set a requirement that 5.75% of petroleum fuels were to be replaced with biofuel sources across all member states by 2010. It was projected in 2006 that by 2020, production would be six times more than demand, creating an excess of glycerol as a byproduct of biofuel production.[8]

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 US$0.02–0.05 per kilogram in 2011.[13] It can be purified, but the process is expensive. Some glycerol is burned for energy, but its heat value is low.[14]

Crude glycerol from the hydrolysis of triglycerides can be purified by treatment with activated carbon to remove organic impurities, alkali to remove unreacted glycerol esters, and ion exchange to remove salts. High purity glycerol (greater than 99.5%) is obtained by multi-step distillation; a vacuum chamber is necessary due to its high boiling point (290 °C).[8]

### Synthetic glycerol

Because of the large-scale production of biodiesel from fats, where glycerol is a waste product, the market for glycerol is depressed. Thus, synthetic processes are not economical. Owing to oversupply, efforts are being made to convert glycerol to synthetic precursors, such as acrolein and epichlorohydrin.[15]

Although usually not cost-effective because so much is produced from processing of fats, glycerol can be produced by various routes. During World War II, synthetic glycerol processes became a national defense priorities because it is a precursor to nitroglycerine. Epichlorohydrin is the most important precursor. chlorination of propylene gives allyl chloride, which is oxidized with hypochlorite to dichlorohydrin, which reacts with a strong base to give epichlorohydrin. Epichlorohydrin can be hydrolyzed to glycerol. Chlorine-free processes from propylene include the synthesis of glycerol from acrolein and propylene oxide.[8]

## Applications

### Food industry

In food 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., cookies), and as a thickening agent in liqueurs. Glycerol and water are used to preserve certain types of plant leaves.[16] 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 a dental plaque and cause dental cavities.[citation needed] As a food additive, glycerol is labeled as E number 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 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.

It is also recommended as an additive when using polyol sweeteners such as erythritol and xylitol which have a cooling effect, due to its heating effect in the mouth, if the cooling effect is not wanted.[17]

Excessive consumption by children can lead to glycerol intoxication.[18] Symptoms of intoxication include hypoglycemia, nausea and a loss of consciousness (syncope). 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 to reduce the risk of intoxication.[19]

### Medical, pharmaceutical and personal care applications

A bottle of glycerin purchased at a pharmacy Personal lubricants commonly contain glycerol Glycerol is an ingredient in products such as hair gel Glycerol suppositories used as laxatives

Glycerin is mildly antimicrobial and antiviral and is an FDA-approved treatment for wounds. The Red Cross reports that an 85% solution of glycerin shows bactericidal and antiviral effects, and wounds treated with glycerin show reduced inflammation after roughly two hours. Due to this it is used widely in wound care products, including glycerin based hydrogel sheets for burns and other wound care. It is approved for all types of wound care except third-degree burns, and is used to package donor skin used in skin grafts.[20]

Glycerol is used in medical, pharmaceutical and personal care preparations, often as a means of improving smoothness, providing lubrication, and as a humectant.

Ichthyosis and xerosis have been relieved by the topical use of glycerin.[21][22] It is found in allergen immunotherapies, cough syrups, elixirs and expectorants, toothpaste, mouthwashes, 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 FDA among the sugar alcohols as a caloric macronutrient. Glycerol is also used in blood banking to preserve red blood cells prior to freezing.

Glycerol is 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]

Taken rectally, glycerol functions as a laxative by irritating the anal mucosa and inducing a hyperosmotic effect,[23] expanding the colon by drawing water into it to induce peristalsis resulting in evacuation.[24] It may be administered undiluted either as a suppository or as a small-volume (2–10 ml) enema. Alternatively, it may be administered in a dilute solution, such as 5%, as a high-volume enema.[25]

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.[26]

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 at inhibiting Clostridioides difficile infection without having a significant effect on the overall microbial composition of the gut.[27]

Glycerol has also been incorporated as a component of bio-ink formulations in the field of bioprinting.[28] 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 (tinctures). 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.[29][30]

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.[31] 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 possesses the intrinsic property of not denaturing or rendering a botanical's constituents inert like alcohols (ethanol, methanol, 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 mitigates reduction-oxidation of a finished extract's constituents, even over several years.[citation needed] Both glycerol and ethanol are viable preserving agents. Glycerol is bacteriostatic in its action, and ethanol is bactericidal in its action.[32][33][34]

### Electronic cigarette liquid

Glycerin is often used in electronic cigarettes to create the vapor

Glycerin, along with propylene glycol, is a common component of e-liquid, a solution used with electronic vaporizers (electronic cigarettes). This glycerol is heated with an atomizer (a heating coil often made of Kanthal wire), producing the aerosol that delivers nicotine to the user.[35]

### Antifreeze

Main article: Chemistry: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 interaction disrupts the formation of ice. The minimum freezing point temperature is about −38 °C (−36 °F) 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.[36][37]

In the laboratory, glycerol is a common component of solvents for enzymatic reagents stored at temperatures below 0 °C (32 °F) due to the depression of the freezing temperature. 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 fungi, bacteria, nematodes, and mammalian embryos. Some organisms like the moor frog produce glycerol to survive freezing temperatures during hibernation.[38]

### Chemical intermediate

Glycerol is used to produce a variety of useful derivatives.

Nitration gives nitroglycerin, an essential ingredient of various explosives such as dynamite, gelignite, and propellants like cordite. Nitroglycerin under the name glyceryl trinitrate (GTN) is commonly used to relieve angina pectoris, taken in the form of sub-lingual tablets, patches, or as an aerosol spray.

Trifunctional polyether polyols are produced from glycerol and propylene oxide.

Oxidation of glycerol affords mesoxalic acid.[39] Dehydrating glycerol affords hydroxyacetone.

Chlorination of glycerol gives the 1-chloropropane-2,3-diol:

HOCH(CH
2OH)
2 \+ HCl → HOCH(CH
2Cl)(CH
2OH) + H

The same compound can be produced by hydrolysis of epichlorohydrin.[40]

### Vibration damping

Glycerol is used as fill for pressure gauges to damp vibration. External vibrations, from compressors, engines, pumps, etc., produce harmonic vibrations within Bourdon gauges 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.[41]

### 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.[42]

Glycerine is also used in the generation of theatrical smoke and fog as a component of the fluid used in fog machines as a replacement for glycol, 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, as it has favourably higher acoustic impedance (2.42 MRayl versus 1.483 MRayl for water) while being relatively safe, non-toxic, non-corrosive and relatively low cost.[43]

### Internal combustion fuel

Glycerol is also used to power diesel generators supplying electricity for the FIA Formula E series of electric race cars.[44]

### Research on additional uses

Research continues into potential value-added products of glycerol obtained from biodiesel production.[45] Examples (aside from combustion of waste glycerol):

* Hydrogen gas production.[46]
* Glycerine acetate is a potential fuel additive.[47]
* Additive for starch thermoplastic.[48][49]
* Conversion to various other chemicals:
* Propylene glycol[50]
* Acrolein[51][52][53]
* Ethanol[54][55]
* Epichlorohydrin,[56] a raw material for epoxy resins

## Metabolism

Glycerol is a precursor for synthesis of triacylglycerols and of phospholipids in the liver and adipose tissue. When the body uses stored fat as a source of energy, glycerol and fatty acids 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.[57][58]

Blood glycerol levels are highly elevated during diabetes, 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.[59]

Circulating glycerol does not glycate proteins as do glucose or fructose, and does not lead to the formation of advanced glycation endproducts (AGEs). In some organisms, the glycerol component can enter the glycolysis pathway directly and, thus, provide energy for cellular metabolism (or, potentially, be converted to glucose through gluconeogenesis).

Before glycerol can enter the pathway of glycolysis or gluconeogenesis (depending on physiological conditions), it must be converted to their intermediate glyceraldehyde 3-phosphate in the following steps:

Glycerol

Glycerol kinase

ATP

ADP

Glycerol-3-phosphate

Glycerol-3-phosphate dehydrogenase

NAD+

NADH

NAD+

NADH

Dihydroxyacetone phosphate

Triosephosphate isomerase

Glyceraldehyde 3-phosphate

The enzyme glycerol kinase is present mainly in the liver and kidneys, but also in other body tissues, including muscle and brain.[60][61][62] In adipose tissue, glycerol 3-phosphate is obtained from dihydroxyacetone phosphate with the enzyme glycerol-3-phosphate dehydrogenase.

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 (SD) rats exposed to 0.03, 0.16 and 0.66 mg/L glycerin (Per liter of air) for 6-hour continuous sessions revealed no treatment-related toxicity other than minimal metaplasia of the epithelium lining at the base of the epiglottis in rats exposed to 0.66 mg/L glycerin.[63][64]

## 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 contamination.[65] 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.[66][67] 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, a drug used to treat infections.[68]

## Etymology

The origin of the gly- and glu\- prefixes for glycols and sugars is from Ancient Greek γλυκύς glukus which means sweet.[69] Name glycérine was coined ca. 1811 by Michel Eugène Chevreul to denote what was previously called "sweet principle of fat" by its discoverer Carl Wilhelm Scheele. 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:[70][71]

Temperature (°C)  | Density (kg/m3)  | Specific heat (kJ/kg·K)  | Kinematic viscosity (m2/s)  | Conductivity (W/m·K)  | Thermal diffusivity (m2/s)  | Prandtl number | Bulk modulus (K−1)

|
|
|
|
|
|
|

0  | 1276.03  | 2.261  | 8.31×10−3 | 0.282  | 9.83×10−8 | 84700  | 4.7×10−4
10  | 1270.11  | 2.319  | 3.00×10−3 | 0.284  | 9.65×10−8 | 31000  | 4.7×10−4
20  | 1264.02  | 2.386  | 1.18×10−3 | 0.286  | 9.47×10−8 | 12500  | 4.8×10−4
30  | 1258.09  | 2.445  | 5.00×10−4 | 0.286  | 9.29×10−8 | 5380  | 4.8×10−4
40  | 1252.01  | 2.512  | 2.20×10−4 | 0.286  | 9.14×10−8 | 2450  | 4.9×10−4
50  | 1244.96  | 2.583  | 1.50×10−4 | 0.287  | 8.93×10−8 | 1630  | 5.0×10−4

## See also

* Dioxalin
* Epichlorohydrin
* Nitroglycerin
* Oleochemicals
* Saponification/Soapmaking
* Solketal
* Transesterification

## References

1. ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. pp. 690. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
2. ↑ 2.0 2.1 2.2 2.3 2.4 NIOSH Pocket Guide to Chemical Hazards. "#0302". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0302.html.
3. ↑ "glycerin_msds". https://www.chemsrc.com/en/cas/56-81-5_401679.html.
4. ↑ Segur, J. B.; Oberstar, H. E. (1951). "Viscosity of Glycerol and Its Aqueous Solutions". Industrial & Engineering Chemistry 43 (9): 2117–2120. doi:10.1021/ie50501a040.
5. ↑ Lide, D. R., ed (1994). CRC Handbook of Data on Organic Compounds (3rd ed.). Boca Raton, FL: CRC Press. p. 4386.
6. ↑ "glycerol – Definition of glycerol in English by Oxford Dictionaries". https://www.oxforddictionaries.com/definition/english/glycerol.
7. ↑ Dams, Rosemeri I.; Viana, Michael B.; Guilherme, Alexandre A.; Silva, Camila M.; Dos Santos, André B.; Angenent, Largus T.; Santaella, Sandra T.; Leitão, Renato C. (2018). "Production of medium-chain carboxylic acids by anaerobic fermentation of glycerol using a bioaugmented open culture". Biomass and Bioenergy 118: 1–7. doi:10.1016/j.biombioe.2018.07.023. https://doi.org/10.1016/j.biombioe.2018.07.023. Retrieved 16 September 2021.
8. ↑ 8.0 8.1 8.2 8.3 Christoph, Ralf; Schmidt, Bernd; Steinberner, Udo; Dilla, Wolfgang; Karinen, Reetta (2006). Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a12_477.pub2. ISBN 3527306730.
9. ↑ Hirschmann, H. (1960-10-01). "The Nature of Substrate Asymmetry in Stereoselective Reactions". Journal of Biological Chemistry 235 (10): 2762–2767. doi:10.1016/S0021-9258(18)64537-5. PMID 13714619.
10. ↑ "IUPAC-IUB Commission on Biochemical Nomenclature (CBN)". European Journal of Biochemistry 2 (2): 127–131. 1967-09-01. doi:10.1111/j.1432-1033.1967.tb00116.x. PMID 6078528.
11. ↑ "Effects of Plant Oil Interesterified Triacylglycerols on Lipemia and Human Health". International Journal of Molecular Sciences 19 (1): E104. 2017. doi:10.3390/ijms19010104. PMID 29301208.
12. ↑ Nilles, Dave (2005). "A Glycerin Factor". Biodiesel Magazine. https://www.biodieselmagazine.com/article.jsp?article_id=377.
13. ↑ San Kong, Pei; Kheireddine Aroua, Mohamed; Ashri Wan Daud, Wan Mohd (2016). "Conversion of crude and pure glycerol into derivatives: A feasibility evaluation". Renewable and Sustainable Energy Reviews 63: 533–555. doi:10.1016/j.rser.2016.05.054.
14. ↑ Sims, Bryan (25 October 2011). "Clearing the way for byproduct quality: why quality for glycerin is just as important for biodiesel". Biodiesel Magazine. https://www.biodieselmagazine.com/articles/8137/clearing-the-way-for-byproduct-quality.
15. ↑ Yu, Bin (2014). "Glycerol". Synlett 25 (4): 601–602. doi:10.1055/s-0033-1340636.
16. ↑ Gouin, Francis R. (1994). "Preserving flowers and leaves". Maryland Cooperative Extension Fact Sheet 556: 1–6. https://extension.umd.edu//sites/extension.umd.edu/files/_images/programs/hgic/Publications/non_HGIC_FS/FS556.pdf. Retrieved 20 January 2018.
17. ↑ Nikolov, Ivan (20 April 2014). "Functional Food Design Rules". https://www.ivannikolov.com/functional-food-design-rules-part-2/.
18. ↑ Burrell, Chloe (2023-06-02). "Perth and Kinross parents warned as 'intoxicated' kids hospitalised by slushy drinks" (in en-GB). https://www.thecourier.co.uk/fp/news/perth-kinross/4445065/perth-kinross-warning-slushy-drinks/.
19. ↑ "'Not suitable for under-4s': New industry guidance issued on glycerol in slush-ice drinks" (in en). https://www.food.gov.uk/news-alerts/news/not-suitable-for-under-4s-new-industry-guidance-issued-on-glycerol-in-slush-ice-drinks.
20. ↑ Stout, Edward I.; McKessor, Angie (February 2012). "Glycerin-Based Hydrogel for Infection Control". Advances in Wound Care 1 (1): 48–51. doi:10.1089/wound.2011.0288. PMID 24527279.
21. ↑ (in en) Ichthyosis: New Insights for the Healthcare Professional. ScholarlyEditions. 22 July 2013. p. 22. ISBN 9781481659666.
22. ↑ Mark G. Lebwohl; Warren R. Heymann; John Berth-Jones; Ian Coulson (19 September 2017) (in en). Treatment of Skin Disease E-Book: Comprehensive Therapeutic Strategies. Elsevier Health Sciences. ISBN 9780702069130.
23. ↑ "Glycerin Enema". Drugs.com. https://www.drugs.com/cdi/glycerin-enema.html.
24. ↑ "glycerin enema". NCI Drug Dictionary. National Cancer Institute. 2 February 2011. https://www.cancer.gov/publications/dictionaries/cancer-drug/def/glycerin-enema.
25. ↑ E. Bertani; A. Chiappa; R. Biffi; P. P. Bianchi; D. Radice; V. Branchi; S. Spampatti; I. Vetrano et al. (2011), "Comparison of oral polyethylene glycol plus a large volume glycerine enema with a large volume glycerine enema alone in patients undergoing colorectal surgery for malignancy: a randomized clinical trial", Colorectal Disease 13 (10): e327–e334, doi:10.1111/j.1463-1318.2011.02689.x, PMID 21689356
26. ↑ "Glycerin (Oral Route)". Mayo Foundation for Medical Education and Research. https://www.mayoclinic.com/health/drug-information/DR601713.
27. ↑ Spinler, Jennifer K.; Auchtung, Jennifer; Brown, Aaron; Boonma, Prapaporn; Oezguen, Numan; Ross, Caná L.; Luna, Ruth Ann; Runge, Jessica et al. (October 2017). "Next-Generation Probiotics Targeting Clostridium difficile through Precursor-Directed Antimicrobial Biosynthesis". Infection and Immunity 85 (10): e00303–17. doi:10.1128/IAI.00303-17. ISSN 1098-5522. PMID 28760934.
28. ↑ Atala, Anthony; Yoo, James J.; Carlos Kengla; Ko, In Kap; Lee, Sang Jin; Kang, Hyun-Wook (March 2016). "A 3D bioprinting system to produce human-scale tissue constructs with structural integrity". Nature Biotechnology 34 (3): 312–319. doi:10.1038/nbt.3413. ISSN 1546-1696. PMID 26878319.
29. ↑ Long, Walter S. (14 January 1916). "The Composition of Commercial Fruit Extracts". Transactions of the Kansas Academy of Science 28: 157–161. doi:10.2307/3624347.
30. ↑ Does alcohol belong in herbal tinctures? newhope.com
31. ↑ "Glycerine: An Overview". The Soap and Detergent Association. 1990. https://www.aciscience.org/docs/Glycerine_-_an_overview.pdf.
32. ↑ Lawrie, James W. (1928) Glycerol and the glycols – production, properties and analysis. The Chemical Catalog Company, Inc., New York, NY.
33. ↑ Leffingwell, Georgia and Lesser, Miton (1945) Glycerin – its industrial and commercial applications. Chemical Publishing Co., Brooklyn, NY.[page needed]
34. ↑ The manufacture of glycerol – Vol. III (1956). The Technical Press, LTD., London.[page needed]
35. ↑ Dasgupta, Amitava; Klein, Kimberly (2014). "4.2.5 Are Electronic Cigarettes Safe?". Antioxidants in Food, Vitamins and Supplements: Prevention and Treatment of Disease. Academic Press. ISBN 9780124059177. https://books.google.com/books?id=5iiSAgAAQBAJ&q=propylene glycol electronic cigarettes&pg=PA67. Retrieved 16 August 2017.
36. ↑ Hudgens, R. Douglas; Hercamp, Richard D.; Francis, Jaime; Nyman, Dan A.; Bartoli, Yolanda (2007). "An Evaluation of Glycerin (Glycerol) as a Heavy Duty Engine Antifreeze/Coolant Base". SAE Technical Paper Series. 1. doi:10.4271/2007-01-4000.
37. ↑ Proposed ASTM Engine Coolant Standards Focus on Glycerin . Astmnewsroom.org. Retrieved on 15 August 2012
38. ↑ Shekhovtsov, Sergei V.; Bulakhova, Nina A.; Tsentalovich, Yuri P.; Zelentsova, Ekaterina A.; Meshcheryakova, Ekaterina N.; Poluboyarova, Tatiana V.; Berman, Daniil I. (January 2022). "Metabolomic Analysis Reveals That the Moor Frog Rana arvalis Uses Both Glucose and Glycerol as Cryoprotectants" (in en). Animals 12 (10): 1286. doi:10.3390/ani12101286. ISSN 2076-2615. PMID 35625132.
39. ↑ Ciriminna, Rosaria; Pagliaro, Mario (2003). "One-Pot Homogeneous and Heterogeneous Oxidation of Glycerol to Ketomalonic Acid Mediated by TEMPO". Advanced Synthesis & Catalysis 345 (3): 383–388. doi:10.1002/adsc.200390043.
40. ↑ Sutter, Marc; Silva, Eric Da; Duguet, Nicolas; Raoul, Yann; Métay, Estelle; Lemaire, Marc (2015). "Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies". Chemical Reviews 115 (16): 8609–8651. doi:10.1021/cr5004002. PMID 26196761. https://hal.archives-ouvertes.fr/hal-01312971/file/ChemRev_2015_115_8609-8651.pdf.
41. ↑ Pneumatic Systems: Principles and Maintenance by S. R. Majumdar. McGraw-Hill, 2006, p. 74 [ISBN missing]
42. ↑ Chemicals in Film reagent.co.uk
43. ↑ Acoustic Properties for Liquids nde-ed.org
44. ↑ Formula E uses pollution-free glycerine to charge cars. fiaformulae.com. 13 September 2014
45. ↑ Johnson, Duane T.; Taconi, Katherine A. (2007). "The glycerin glut: Options for the value-added conversion of crude glycerol resulting from biodiesel production". Environmental Progress 26 (4): 338–348. doi:10.1002/ep.10225.
46. ↑ Marshall, A. T.; Haverkamp, R. G. (2008). "Production of hydrogen by the electrochemical reforming of glycerol-water solutions in a PEM electrolysis cell". International Journal of Hydrogen Energy 33 (17): 4649–4654. doi:10.1016/j.ijhydene.2008.05.029.
47. ↑ Melero, Juan A.; Van Grieken, Rafael; Morales, Gabriel; Paniagua, Marta (2007). "Acidic mesoporous silica for the acetylation of glycerol: Synthesis of bioadditives to petrol fuel". Energy & Fuels 21 (3): 1782–1791. doi:10.1021/ef060647q.
48. ↑ Özeren, Hüsamettin D.; Olsson, Richard T.; Nilsson, Fritjof; Hedenqvist, Mikael S. (2020-02-01). "Prediction of plasticization in a real biopolymer system (starch) using molecular dynamics simulations" (in en). Materials & Design 187: 108387. doi:10.1016/j.matdes.2019.108387. ISSN 0264-1275.
49. ↑ Özeren, Hüsamettin Deniz; Guivier, Manon; Olsson, Richard T.; Nilsson, Fritjof; Hedenqvist, Mikael S. (2020-04-07). "Ranking Plasticizers for Polymers with Atomistic Simulations; PVT, Mechanical Properties and the Role of Hydrogen Bonding in Thermoplastic Starch". ACS Applied Polymer Materials 2 (5): 2016–2026. doi:10.1021/acsapm.0c00191.
50. ↑ "Dow achieves another major milestone in its quest for sustainable chemistries" (Press release). Dow Chemical Company. 15 March 2007. Archived from the original on 16 September 2009. Retrieved 13 July 2007.
51. ↑ Ott, L.; Bicker, M.; Vogel, H. (2006). "The catalytic dehydration of glycerol in sub- and supercritical water: a new chemical process for acrolein production". Green Chemistry 8 (2): 214–220. doi:10.1039/b506285c.
52. ↑ Watanabe, Masaru; Iida, Toru; Aizawa, Yuichi; Aida, Taku M.; Inomata, Hiroshi (2007). "Acrolein synthesis from glycerol in hot-compressed water". Bioresource Technology 98 (6): 1285–1290. doi:10.1016/j.biortech.2006.05.007. PMID 16797980.
53. ↑ Abdullah, Anas; Zuhairi Abdullah, Ahmad; Ahmed, Mukhtar; Khan, Junaid; Shahadat, Mohammad; Umar, Khalid; Alim, Md Abdul (March 2022). "A review on recent developments and progress in sustainable acrolein production through catalytic dehydration of bio-renewable glycerol" (in en). Journal of Cleaner Production 341: 130876. doi:10.1016/j.jclepro.2022.130876. https://linkinghub.elsevier.com/retrieve/pii/S0959652622005145.
54. ↑ Yazdani, S. S.; Gonzalez, R. (2007). "Anaerobic fermentation of glycerol: a path to economic viability for the biofuels industry". Current Opinion in Biotechnology 18 (3): 213–219. doi:10.1016/j.copbio.2007.05.002. PMID 17532205.
55. ↑ "Engineers Find Way To Make Ethanol, Valuable Chemicals From Waste Glycerin". ScienceDaily (Press release). 27 June 2007.
56. ↑ "Dow Epoxy advances glycerine-to-epichlorohydrin and liquid epoxy resins projects by choosing Shanghai site" (Press release). Dow Chemical Company. 26 March 2007. Archived from the original on 8 December 2011. Retrieved 21 February 2022.
57. ↑ Glycerol clearance in alcoholic liver disease. Gut (British Society of Gastroenterology). 1982 Apr; 23(4): 257–264. D G Johnston, K G Alberti, R Wright, P G Blain
58. ↑ "Fatty liver disrupts glycerol metabolism in gluconeogenic and lipogenic pathways in humans". September 2018 The Journal of Lipid Research, 59, 1685–1694. Jeffrey D. Browning, Eunsook S. Jin1, Rebecca E. Murphy, and Craig R. Malloy
59. ↑ Molecular Human Reproduction, Volume 23, Issue 11, November 2017, pp. 725–737
60. ↑ Tildon, J. T.; Stevenson, J. H. Jr.; Ozand, P. T. (1976). "Mitochondrial glycerol kinase activity in rat brain". The Biochemical Journal 157 (2): 513–516. doi:10.1042/bj1570513. PMID 183753.
61. ↑ Newsholme, E. A.; Taylor, K (May 1969). "Glycerol kinase activities in muscles from vertebrates and invertebrates". Biochem. J. 112 (4): 465–474. doi:10.1042/bj1120465. PMID 5801671.
62. ↑ "Glycerol Kinase and Dihydroxyacetone Kinase in Rat Brain". Journal of Neurochemistry 26 (2): 377–385. 1976. doi:10.1111/j.1471-4159.1976.tb04491.x. PMID 3631. https://deepblue.lib.umich.edu/bitstream/2027.42/65297/1/j.1471-4159.1976.tb04491.x.pdf. Retrieved 27 August 2019.
63. ↑ Phillips, Blaine; Titz, Bjoern; Kogel, Ulrike; Sharma, Danilal; Leroy, Patrice; Xiang, Yang; Vuillaume, Grégory; Lebrun, Stefan et al. (2017). "Toxicity of the main electronic cigarette components, propylene glycol, glycerin, and nicotine, in Sprague–Dawley rats in a 90-day OECD inhalation study complemented by molecular endpoints". Food and Chemical Toxicology 109 (Pt 1): 315–332. doi:10.1016/j.fct.2017.09.001. PMID 28882640.
64. ↑ Renne, R. A.; Wehner, A. P.; Greenspan, B. J.; Deford, H. S.; Ragan, H. A.; Westerberg, R. B. (1992). "2-Week and 13-Week Inhalation Studies of Aerosolized Glycerol in Rats". International Forum for Respiratory Research 4 (2): 95–111. doi:10.3109/08958379209145307.
65. ↑ "FDA Advises Manufacturers to Test Glycerin for Possible Contamination". U.S. Food and Drug Administration. 4 May 2007. https://www.fda.gov/bbs/topics/NEWS/2007/NEW01628.html.
66. ↑ Walt Bogdanich (6 May 2007). "From China to Panama, a Trail of Poisoned Medicine". The New York Times. https://www.nytimes.com/2007/05/06/world/06poison.html.
67. ↑ "10 Biggest Medical Scandals in History". 20 February 2013. https://www.topmastersinpublichealth.com/10-biggest-medical-scandals-in-history.
68. ↑ Lang, Les (2007-07-01). "FDA Issues Statement on Diethylene Glycol and Melamine Food Contamination" (in en). Gastroenterology 133 (1): 5–6. doi:10.1053/j.gastro.2007.05.013. ISSN 0016-5085. PMID 17631118. https://www.gastrojournal.org/article/S0016-5085(07)00995-X/abstract. Retrieved 25 December 2020.
69. ↑ glyco- , dictionary.com
70. ↑ Holman, Jack P. (2002) (in English). Heat Transfer (9th ed.). New York, NY: McGraw-Hill Companies, Inc.. pp. 600–606. ISBN 9780072406559.
71. ↑ Incropera 1 Dewitt 2 Bergman 3 Lavigne 4, Frank P. 1 David P. 2 Theodore L. 3 Adrienne S. 4 (2007) (in English). Fundamentals of Heat and Mass Transfer (6th ed.). Hoboken, NJ: John Wiley and Sons, Inc.. pp. 941–950. ISBN 9780471457282.

## External links

* Mass spectrum of glycerol
* CDC – NIOSH Pocket Guide to Chemical Hazards – Glycerin (mist)

* v
* t
* e

Alcohols

Straight-chain
primary
alcohols (1°)|

* Methanol (C1)
* Ethanol (C2)
* 1-Propanol (C3)
* n-Butanol (C4)
* 1-Pentanol (C5)
* 1-Hexanol (C6)
* 1-Heptanol (C7)
* 1-Octanol (C8)
* 1-Nonanol (C9)
* 1-Decanol (C10)
* Undecanol (C11)
* Dodecanol (C12)
* Tridecan-1-ol (C13)
* 1-Tetradecanol (C14)
* 1-Pentadecanol (C15)
* Cetyl alcohol (C16)
* Heptadecan-1-ol (C17)
* Stearyl alcohol (C18)
* Nonadecan-1-ol (C19)
* Arachidyl alcohol (C20)
* Heneicosan-1-ol (C21)
* Docosanol (C22)
* Tricosan-1-ol (C23)
* 1-Tetracosanol (C24)
* Pentacosan-1-ol (C25)
* 1-Hexacosanol (C26)
* 1-Heptacosanol (C27)
* 1-Octacosanol (C28)
* 1-Nonacosanol (C29)
* Triacontanol (C30)
* Hentriacontanol (C31)
* Dotriacontanol (C32)
* Tritriacontanol (C33)
* Tetratriacontanol (C34)
* Pentatriacontanol (C35)
* Hexatriacontanol (C36)
* 1-Heptatriacontanol (C37)
* 1-Octatriacontanol (C38)
* Nonatriacontan-1-ol (C39)
* Tetracontanol (C40)

Other primary
alcohols|

* Isobutanol (C4)
* Isoamyl alcohol (C5)
* 2-Methyl-1-butanol (C5)
* Phenethyl alcohol (C8)
* Tryptophol (C10)

Secondary
alcohols (2°)|

* Isopropanol (C3)
* Cyclopropanol (C3)
* 2-Butanol (C4)
* 2-Pentanol (C5)
* 3-Pentanol (C5)
* Cyclopentanol (C5)
* 2-Hexanol (C6)
* 3-Hexanol (C6)
* Pinacolyl alcohol (C6)
* Cyclohexanol (C6)
* 2-Heptanol (C7)
* 3-Heptanol (C7)
* 2-Octanol (C8)

Tertiary
alcohols (3°)|

* tert-Butyl alcohol (C4)
* tert-Amyl alcohol (C5)
* 2-Methyl-2-pentanol (C6)
* 2-Methylhexan-2-ol (C7)
* 2-Methylheptan-2-ol (C8)
* 3-Methyl-3-pentanol (C6)
* 3-Methyloctan-3-ol (C9)

Preparations|

* Substitution of haloalkane
* Carbonyl reduction
* Ether cleavage
* Hydrolysis of epoxide
* Hydration of alkene
* Ziegler process

Reactions|

* Deprotonation
* Protonation
* Alcohol oxidation
* Glycol cleavage
* Nucleophilic substitution
* Fischer–Speier esterification
* Williamson ether synthesis
* Elimination reaction
* Nucleophilic substitution of carbonyl group
* Friedel-Crafts alkylation
* Nucleophilic conjugate addition
* Transesterification

* Category

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