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Keyword,
คำสัญคัญ, ชื่อเรียกอื่นๆ
Glycerine,
กลีเซอรีน
Glycerine
USP, กลีเซอรีนเกรดยูเอสพี
Glycerine
Pharmaceutical Grade, กลีเซอรีนเกรดยา
Pure
Glycerine, กลีเซอรีนบริสุทธิ์
Reifined
Glycerine, รีไฟน์กลีเซอรีน
Glycerine
99.5% Min, กลีเซอรีน 99.5 %
99.5% purified Glycerine, กลีเซอรีนบริสุทธิ์ 99.5%
Glycerine
99.5% USP, กลีเซอรีนเกรดUSP 99.5%
Liquid Glycerine,
กลีเซอรีนเหลว
Glycerol,
กลีเซอรอล
Glycerol
USP, กลีเซอรอลเกรดยูเอสพี
Glycerol
Pharma Grade, กลีเซอรอลเกรดยา
Pure
Glycerol, กลีเซอรอลบริสุทธิ์
Reifined
Glycerol, รีไฟน์กลีเซอรอล
Glycerol
99.5% Min, กลีเซอรอล 99.5%
99.5% purified Glycerol, กลีเซอรอลบริสุทธิ์ 99.5%
1,2,3-Propanetriol,
โพรเพนไตรออล
Glyceritol,
กลีเซอริตอล
Glycic
Alcohol, ไกลซิสแอลกอฮอล์
1,2,3-Trihydroxypropane,
ไตรไฮดรอกซีโพรเพน
CAS No.
56-81-5, C3H5(OH)3, Glycerin, propane-1,2,3-triol
กลีเซอรีนเหลว กลีเซอรีนบริสุทธิ์ 99.5% หรือ Refined Glycerine 99.5% กลีเซอรีนบริสุทธิ์ มีลักษณะเป็นของเหลวใส รสหวาน กลีเซอรีน ถูกใช้งานอย่างกว้างขวางเป็น สารละลาย(solvent) สารเพิ่มความหวาน(sweetener) เครื่องสำอาง(cosmetics and personal care products) สบู่เหลว(liquid soaps) ลูกอม(candy) สุรา(liqueurs) หมึก(inks) และสารหล่อลื่น(lubricants) เพื่อให้ยืดหยุ่น(pliable) สารป้องกันการแข็งตัว (antifreeze mixtures) เป็นส่วนผสมอาหาร(Food and beverage ingredients ) อาหารสัตว์(Animal feed ) สารปฏิชีวนะ(Antibiotics) ยา (Pharmaceuticals) สารให้ความชุ่มชื้น(moisturizers) น้ำมันไฮดรอลิกส์(Hydraulic fluids) และสารตั้งต้นทางปีโตรเคมีต่างๆ(Polyether polyols, propylene glycol, epichlorohydrin และอื่นๆ)
Glycerol /ˈɡlɪsərɒl/[4] (also called glycerine or glycerin;
see spelling differences) is a simple polyol compound. It is a colorless,
odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol
backbone is found in all lipids known as triglycerides. It is widely used in
the food industry as a sweetener and humectant and in pharmaceutical
formulations. Glycerol has three hydroxyl groups that are responsible for its
solubility in water and its hygroscopic nature.[5]
Structure[edit]
Although achiral, glycerol is prochiral with respect to
reactions of one of the two primary alcohols. Thus, in substituted derivatives,
the stereospecific numbering labels each carbon as either sn-1, sn-2, or
sn-3.[6][7]
Production[edit]
Glycerol is generally obtained from plant and animal sources
where it occurs as triglycerides. Triglycerides are 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:.
SaponificationGeneral.svg
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):
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 United States alone from 2000 to 2004.[8] Production will increase as
the EU directive 2003/30/EC are implemented, which required the replacement of
5.75% of petroleum fuels with biofuel across all member states by 2010, as
glycerol is a byproduct in the production of biodiesel. It was projected in
2006 that by the year 2020, production would be six times more than
demand.[5][needs update]
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 per pound in 2011.[9] It can be purified, but the process
is expensive. Some glycerol is burned for energy, but the heat value is
low.[10]
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 (> 99.5%) is obtained by multi-step distillation;
vacuum is helpful due to the high boiling point of glycerol (290 °C).[5]
Synthetic glycerol[edit]
Although usually not cost-effective, glycerol can 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. This epichlorohydrin is then
hydrolyzed to give glycerol. Chlorine-free processes from propylene include the
synthesis of glycerol from acrolein and propylene oxide.[5]
Synthetic routes to glycerol.png
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.[11] (See the Chemical intermediate section of this article.)
Applications[edit]
Food industry[edit]
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.[12] 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. It is added to icing (frosting) to
prevent it from setting too hard.
As used in foods, glycerol is categorized by the 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, so some dietary advocates[who?] accept glycerol as a sweetener
compatible with low carbohydrate diets.
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.[13]
Pharmaceutical and personal care applications[edit]
Glycerol suppositories used as laxatives
Glycerol is used in medical and pharmaceutical and personal
care preparations, mainly as a means of improving smoothness, providing
lubrication and as a humectant. 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 U.S. FDA among the sugar
alcohols as a caloric macronutrient.
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]
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 and induces a hyperosmotic effect.[14]
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.[15]
Botanical extracts[edit]
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 sense, as glycerol contains three
hydroxyl groups. Fluid extract manufacturers often extract herbs in hot water
before adding glycerol to make glycerites.[16][17]
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.[citation needed] That glycerol possesses such high extractive power
assumes it is utilized with dynamic 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 (as alcohols – i.e. ethyl (grain) alcohol,
methyl (wood) alcohol, etc., 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.[citation needed] Both
glycerol and ethanol are viable preserving agents. Glycerol is bacteriostatic
in its action, and ethanol is bactericidal in its action.[18][19][20]
Electronic cigarette liquid[edit]
Vegetable glycerin is a common component of e-liquid, a
solution used with electronic vaporizers (electronic cigarettes), that is
heated with an atomizer to produce a vapor in order to deliver flavors and
optionally nicotine.
Antifreeze[edit]
Main article: 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.[21][22]
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. 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.
Internal Combustion Fuel[edit]
Used to power diesel generators supplying electricity for
the FIA Formula E series of electric race cars.[23]
Chemical intermediate[edit]
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 glycerol
made it difficult to increase production to meet wartime demand. Hence,
synthetic glycerol 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.
Allyl iodide, a chemical building block for polymers,
preservatives, organometallic catalysts, and pharmaceuticals, can be
synthesized by using elemental phosphorus and iodine on glycerol.[24]
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.[25] The
use of crude glycerol as an additive to biomass for a renewable energy source
when burned or gasified is also being explored.
Hydrogen gas production unit[26]
Glycerine acetate (as a potential fuel additive)[27]
Conversion to propylene glycol[28]
Conversion to acrolein[29][30]
Conversion to ethanol[31]
Conversion to epichlorohydrin,[32] a raw material for epoxy
resins
Film Industry[edit]
Glycerol is used by the film industry when filming scenes
involving water in order to stop areas from drying out too quickly.[33]
Metabolism[edit]
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. 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[which?] 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 Glycerol-3-phosphate Glycerol-3-phosphate dehydrogenase Dihydroxyacetone phosphate Triosephosphate isomerase Glyceraldehyde 3-phosphate
Glycerin Skelett.svg ATP ADP Glycerol-3-phosphate.png NAD+ NADH
DHAP struct.svg G3P-2D-skeletal.png
Biochem reaction arrow forward YYNN horiz med.svg Biochem reaction arrow reversible YYYY
horiz med.svg Biochem reaction arrow
reversible NNNN horiz med.svg
NAD+ NADH
The enzyme glycerol kinase is present mainly in the liver
and kidneys, but also in other body tissues, including muscle and
brain.[34][35][36] In adipose tissue, glycerol 3-phosphate is obtained from
dihydroxyacetone phosphate (DHAP) 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.
Historical cases of contamination with diethylene[edit]
On 4 May 2007, the US Food and Drug Administration advised
all US makers of medicines to test all batches of glycerol for the toxic
diethylene glycol.[37] 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.[38][39]
Etymology[edit]
The origin of the gly- and glu- prefixes for glycols and sugars
is from Greek glukus which means sweet.[40]
