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Hydrogen peroxide
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Hydrogen peroxide
Names
IUPAC name
Hydrogen peroxide
Other names
Dioxidane
Oxidanyl
Perhydroxic acid
0-hydroxyol
Dihydrogen dioxide
Identifiers
CAS Number
7722-84-1 Y
3D model (JSmol)
Interactive image
ChEBI
CHEBI:16240 Y
ChemSpider
763 Y
ECHA InfoCard 100.028.878
EC Number 231-765-0
IUPHAR/BPS
2448
KEGG
D00008 Y
PubChem CID
784
RTECS number MX0900000 (>90% soln.)
MX0887000 (>30% soln.)
UNII
BBX060AN9V Y
UN number 2015 (>60% soln.)
2014 (20–60% soln.)
2984 (8–20% soln.)
InChI[show]
InChI=1S/H2O2/c1-2/h1-2H Y
Key: MHAJPDPJQMAIIY-UHFFFAOYSA-N Y
InChI=1/H2O2/c1-2/h1-2H
Key: MHAJPDPJQMAIIY-UHFFFAOYAL
SMILES[show]
OO
Properties
Chemical formula
H2O2
Molar mass 34.0147 g/mol
Appearance Very light blue color; colorless in solution
Odor slightly sharp
Density 1.11 g/cm3 (20 °C, 30% (w/w) solution )[1]
1.450 g/cm3 (20 °C, pure)
Melting point −0.43 °C (31.23 °F; 272.72 K)
Boiling point 150.2 °C (302.4 °F; 423.3 K) (decomposes)
Solubility in water
Miscible
Solubility soluble in ether, alcohol
insoluble in petroleum ether
Vapor pressure 5 mmHg (30 °C)[2]
Acidity (pKa) 11.75
Magnetic susceptibility (χ)
−17.7·10−6 cm3/mol
Refractive index (nD)
1.4061
Viscosity 1.245 cP (20 °C)
Dipole moment
2.26 D
Thermochemistry
Specific
heat capacity (C)
1.267 J/(g·K) (gas)
2.619 J/(g·K) (liquid)
Std enthalpy of
formation (ΔfHo298)
−187.80 kJ/mol
Pharmacology
ATC code
A01AB02 (WHO) D08AX01 (WHO), S02AA06 (WHO)
Hazards
Safety data sheet ICSC 0164 (>60% soln.)
GHS pictograms
GHS signal word danger
GHS hazard statements
H271, H302, H314, H332, H335, H412
GHS precautionary statements
P280, P305+351+338, P310
NFPA 704
0
3
3
OX
Flash point Non-flammable
Lethal dose or concentration (LD, LC):
LD50 (median dose)
1518 mg/kg[citation needed]
2000 mg/kg (oral, mouse)[3]
LC50 (median concentration)
1418 ppm (rat, 4 hr)[3]
LCLo (lowest published)
227 ppm (mouse)[3]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 1 ppm (1.4 mg/m3)[2]
REL (Recommended)
TWA 1 ppm (1.4 mg/m3)[2]
IDLH (Immediate danger)
75 ppm[2]
Related compounds
Related compounds
Water
Ozone
Hydrazine
Hydrogen disulfide
Dioxygen difluoride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is Y N ?)
Infobox references
Hydrogen peroxide is a chemical compound with the formula H
2O
2. In its pure form, it is a pale blue, clear liquid, slightly more viscous than water. Hydrogen peroxide is the simplest peroxide (a compound with an oxygen–oxygen single bond). It is used as an oxidizer, bleaching agent and antiseptic. Concentrated hydrogen peroxide, or "high-test peroxide", is a reactive oxygen species and has been used as a propellant in rocketry.[4] Its chemistry is dominated by the nature of its unstable peroxide bond.
Hydrogen peroxide is unstable and slowly decomposes in the presence of base or a catalyst. Because of its instability, hydrogen peroxide is typically stored with a stabilizer in a weakly acidic solution. Hydrogen peroxide is found in biological systems including the human body. Enzymes that use or decompose hydrogen peroxide are classified as peroxidases.
Contents
[hide]
1 Properties
1.1 Aqueous solutions
1.2 Structure
1.3 Comparison with analogues
2 Discovery
3 Manufacture
3.1 Availability
4 Reactions
4.1 Decomposition
4.2 Redox reactions
4.3 Organic reactions
4.4 Precursor to other peroxide compounds
5 Biological function
6 Uses
6.1 Bleaching
6.2 Detergents
6.3 Production of organic compounds
6.4 Disinfectant
6.4.1 Cosmetic applications
6.4.2 Use in alternative medicine
6.5 Propellant
6.6 Other uses
7 Safety
7.1 Historical incidents
8 See also
9 References
10 External links
Properties[edit]
The boiling point of H
2O
2 has been extrapolated as being 150.2 °C, approximately 50 °C higher than water. In practice, hydrogen peroxide will undergo potentially explosive thermal decomposition if heated to this temperature. It may be safely distilled at lower temperatures under reduced pressure.[5]
Aqueous solutions[edit]
In aqueous solutions hydrogen peroxide differs from the pure material due to the effects of hydrogen bonding between water and hydrogen peroxide molecules. Hydrogen peroxide and water form a eutectic mixture, exhibiting freezing-point depression; pure water has a melting point of 0 °C and pure hydrogen peroxide of −0.43 °C. The boiling point of the same mixtures is also depressed in relation with the mean of both boiling points (125.1 °C). It occurs at 114 °C. This boiling point is 14 °C greater than that of pure water and 36.2 °C less than that of pure hydrogen peroxide.[6]
Phase diagram of H
2O
2 and water: Area above blue line is liquid. Dotted lines separate solid+liquid phases from solid+solid phases.
Density of aqueous solution of H2O2
H2O2 (w/w)
Density (g/cm3)
Temperature (°C)
3% 1.0095 15
27% 1.10 20
35% 1.13 20
50% 1.20 20
70% 1.29 20
75% 1.33 20
96% 1.42 20
98% 1.43 20
100% 1.45 20
Structure[edit]
Hydrogen peroxide (H
2O
2) is a nonplanar molecule with (twisted) C2 symmetry. Although the O−O bond is a single bond, the molecule has a relatively high rotational barrier of 2460 cm−1 (29.45 kJ/mol);[7] for comparison, the rotational barrier for ethane is 12.5 kJ/mol. The increased barrier is ascribed to repulsion between the lone pairs of the adjacent oxygen atoms and results in hydrogen peroxide displaying atropisomerism.
The molecular structures of gaseous and crystalline H
2O
2 are significantly different. This difference is attributed to the effects of hydrogen bonding, which is absent in the gaseous state.[8] Crystals of H
2O
2 are tetragonal with the space group D4
4P4121.[9]
Structure and dimensions of H2O2 in the gas phase
Structure and dimensions of H2O2 in the solid (crystalline) phase
Properties of H2O2 and its analogues
values marked * are extrapolated
Name
Formula
Molar mass (g/mol)
TM (°C)
TB (°C)
Hydrogen peroxide HOOH 34.01 −0.43 150.2*
Water HOH 18.02 0.00 99.98
Hydrogen disulfide HSSH 66.15 −89.6 70.7
Hydrazine H2NNH2 32.05 2 114
Hydroxylamine NH2OH 33.03 33 58*
Diphosphane H2PPH2 65.98 −99 63.5*
Comparison with analogues[edit]
Hydrogen peroxide has several structural analogues with Hm−X−X−Hn bonding arrangements (water also shown for comparison). It has the highest (theoretical) boiling point of this series (X = O, N, S). Its melting point is also fairly high, being comparable to that of hydrazine and water, with only hydroxylamine crystallising significantly more readily, indicative of particularly strong hydrogen bonding. Diphosphane and hydrogen disulfide exhibit only weak hydrogen bonding and have little chemical similarity to hydrogen peroxide. All of these analogues are thermodynamically unstable. Structurally, the analogues all adopt similar skewed structures, due to repulsion between adjacent lone pairs.
Discovery[edit]
Alexander von Humboldt synthesized one of the first synthetic peroxides, barium peroxide, in 1799 as a by-product of his attempts to decompose air.
Nineteen years later Louis Jacques Thénard recognized that this compound could be used for the preparation of a previously unknown compound, which he described as oxidized water – subsequently known as hydrogen peroxide.[10] [11] An improved version of this process used hydrochloric acid, followed by addition of sulfuric acid to precipitate the barium sulfate byproduct. Thénard's process was used from the end of the 19th century until the middle of the 20th century.[12]
Thénard and Joseph Louis Gay-Lussac synthesized sodium peroxide in 1811. The bleaching effect of peroxides and their salts on natural dyes became known around that time, but early attempts of industrial production of peroxides failed, and the first plant producing hydrogen peroxide was built in 1873 in Berlin. The discovery of the synthesis of hydrogen peroxide by electrolysis with sulfuric acid introduced the more efficient electrochemical method. It was first implemented into industry in 1908 in Weißenstein, Carinthia, Austria. The anthraquinone process, which is still used, was developed during the 1930s by the German chemical manufacturer IG Farben in Ludwigshafen. The increased demand and improvements in the synthesis methods resulted in the rise of the annual production of hydrogen peroxide from 35,000 tonnes in 1950, to over 100,000 tonnes in 1960, to 300,000 tonnes by 1970; by 1998 it reached 2.7 million tonnes.[13]
Pure hydrogen peroxide was long believed to be unstable, as early attempts to separate it from the water, which is present during synthesis, all failed. This instability was due to traces of impurities (transition-metal salts), which catalyze the decomposition of the hydrogen peroxide. Pure hydrogen peroxide was first obtained in 1894—almost 80 years after its discovery—by Richard Wolffenstein, who produced it by vacuum distillation.[14]
Determination of the molecular structure of hydrogen peroxide proved to be very difficult. In 1892 the Italian physical chemist Giacomo Carrara (1864–1925) determined its molecular mass by freezing-point depression, which confirmed that its molecular formula is H2O2.[15] At least half a dozen hypothetical molecular structures seemed to be consistent with the available evidence.[16] In 1934, the English mathematical physicist William Penney and the Scottish physicist Gordon Sutherland proposed a molecular structure for hydrogen peroxide that was very similar to the presently accepted one.[17]
Manufacture[edit]
Previously, hydrogen peroxide was prepared industrially by hydrolysis of the ammonium peroxydisulfate, which was itself obtained by the electrolysis of a solution of ammonium bisulfate (NH
4HSO
4) in sulfuric acid:
(NH
4)
2S
2O
8 + 2 H
2O → H
2O
2 + 2 (NH
4)HSO
4
Today, hydrogen peroxide is manufactured almost exclusively by the anthraquinone process, which was formalized in 1936 and patented in 1939. It begins with the reduction of an anthraquinone (such as 2-ethylanthraquinone or the 2-amyl derivative) to the corresponding anthrahydroquinone, typically by hydrogenation on a palladium catalyst; the anthrahydroquinone then undergoes autoxidation to regenerate the starting anthraquinone, with hydrogen peroxide as a by-product. Most commercial processes achieve oxidation by bubbling compressed air through a solution of the derivatized anthracene, whereby the oxygen present in the air reacts with the labile hydrogen atoms (of the hydroxy groups), giving hydrogen peroxide and regenerating the anthraquinone. Hydrogen peroxide is then extracted, and the anthraquinone derivative is reduced back to the dihydroxy (anthracene) compound using hydrogen gas in the presence of a metal catalyst. The cycle then repeats itself.[18][19]
The simplified overall equation for the process is simple:[18]
H
2 + O
2 → H
2O
2
The economics of the process depend heavily on effective recycling of the quinone (which is expensive) and extraction solvents, and of the hydrogenation catalyst.
A process to produce hydrogen peroxide directly from the elements has been of interest for many years. Direct synthesis is difficult to achieve, as the reaction of hydrogen with oxygen thermodynamically favours production of water. Systems for direct synthesis have been developed, most of which are based around finely dispersed metal catalysts.[20][21] None of these has yet reached a point where they can be used for industrial-scale synthesis.
ISO tank container for hydrogen peroxide transportation
Availability[edit]
Hydrogen peroxide is most commonly available as a solution in water. For consumers, it is usually available from pharmacies at 3 and 6 wt% concentrations. The concentrations are sometimes described in terms of the volume of oxygen gas generated; one milliliter of a 20-volume solution generates twenty milliliters of oxygen gas when completely decomposed. For laboratory use, 30 wt% solutions are most common. Commercial grades from 70% to 98% are also available, but due to the potential of solutions of more than 68% hydrogen peroxide to be converted entirely to steam and oxygen (with the temperature of the steam increasing as the concentration increases above 68%) these grades are potentially far more hazardous and require special care in dedicated storage areas. Buyers must typically allow inspection by commercial manufacturers.
In 1994, world production of H
2O
2 was around 1.9 million tonnes and grew to 2.2 million in 2006,[22] most of which was at a concentration of 70% or less. In that year bulk 30% H
2O
2 sold for around 0.54 USD/kg, equivalent to 1.50 USD/kg (0.68 USD/lb) on a "100% basis".[23]
Hydrogen peroxide occurs in surface water, groundwater and in the atmosphere. It forms upon illumination or natural catalytic action by substances contained in water. Sea water contains 0.5 to 14 μg/L of hydrogen peroxide, freshwater 1 to 30 μg/L and air 0.1 to 1 parts per billion.[13]
Reactions[edit]
Decomposition[edit]
Hydrogen peroxide is thermodynamically unstable and decomposes to form water and oxygen with a ΔHo of −98.2 kJ/mol and a ΔS of 70.5 J/(mol·K):
2 H
2O
2 → 2 H
2O + O
2
The rate of decomposition increases with rising temperature, concentration and pH, with cool, dilute, acidic solutions showing the best stability. Decomposition is catalysed by various compounds, including most transition metals and their compounds (e.g. manganese dioxide, silver, and platinum).[24] Certain metal ions, such as Fe2+
or Ti3+
, can cause the decomposition to take a different path, with free radicals such as (HO·) and (HOO·) being formed. Non-metallic catalysts include potassium iodide, which reacts particularly rapidly and forms the basis of the elephant toothpaste experiment. Hydrogen peroxide can also be decomposed biologically by the enzyme catalase. The decomposition of hydrogen peroxide liberates oxygen and heat; this can be dangerous, as spilling high-concentration hydrogen peroxide on a flammable substance can cause an immediate fire.
Redox reactions[edit]
Hydrogen peroxide exhibits oxidizing and reducing properties, depending on pH.
In acidic solutions, H
2O
2 is one of the most powerful oxidizers known—stronger than chlorine, chlorine dioxide, and potassium permanganate. Also, through catalysis, H
2O
2 can be converted into hydroxyl radicals (·OH), which are highly reactive.
Oxidant/reduced product
Oxidation potential, V
fluorine/hydrogen fluoride 3.0
ozone/oxygen 2.1
hydrogen peroxide/water 1.8
potassium permanganate/manganese dioxide 1.7
chlorine dioxide/HClO 1.5
chlorine/chloride 1.4
In acidic solutions Fe2+
is oxidized to Fe3+
(hydrogen peroxide acting as an oxidizing agent):
2 Fe2+
(aq) + H
2O
2 + 2 H+
(aq) → 2 Fe3+
(aq) + 2 H
2O(l)
and sulfite (SO2−
3) is oxidized to sulfate (SO2−
4). However, potassium permanganate is reduced to Mn2+
by acidic H
2O
2. Under alkaline conditions, however, some of these reactions reverse; for example, Mn2+
is oxidized to Mn4+
(as MnO
2).
In basic solution, hydrogen peroxide can reduce a variety of inorganic ions. When it acts as a reducing agent, oxygen gas is also produced. For example, hydrogen peroxide will reduce sodium hypochlorite and potassium permanganate, which is a convenient method for preparing oxygen in the laboratory:
NaOCl + H
2O
2 → O
2 + NaCl + H
2O
2 KMnO
4 + 3 H
2O
2 → 2 MnO
2 + 2 KOH + 2 H
2O + 3 O
2
Organic reactions[edit]
Hydrogen peroxide is frequently used as an oxidizing agent. Illustrative is oxidation of thioethers to sulfoxides:[25][26]
Ph−S−CH
3 + H
2O
2 → Ph−S(O)−CH
3 + H
2O
Alkaline hydrogen peroxide is used for epoxidation of electron-deficient alkenes such as acrylic acid derivatives, and for the oxidation of alkylboranes to alcohols, the second step of hydroboration-oxidation. It is also the principal reagent in the Dakin oxidation process.
Precursor to other peroxide compounds[edit]
Hydrogen peroxide is a weak acid, forming hydroperoxide or peroxide salts with many metals.
It also converts metal oxides into the corresponding peroxides. For example, upon treatment with hydrogen peroxide, chromic acid(CrO
3 + H
2SO
4) forms an unstable blue peroxide CrO(O
2)
2.
This kind of reaction is used industrially to produce peroxoanions. For example, reaction with borax leads to sodium perborate, a bleach used in laundry detergents:
Na
2B
4O
7 + 4 H
2O
2 + 2 NaOH → 2 Na
2B
2O
4(OH)
4 + H
2O
H
2O
2 converts carboxylic acids (RCO2H) into peroxy acids (RC(O)O2H), which are themselves used as oxidizing agents. Hydrogen peroxide reacts with acetone to form acetone peroxide and with ozone to form trioxidane. Hydrogen peroxide forms stable adducts with urea (hydrogen peroxide - urea), sodium carbonate (sodium percarbonate) and other compounds.[27] An acid-base adduct with triphenylphosphine oxide is a useful "carrier" for H
2O
2 in some reactions.
The peroxide anion is a stronger nucleophile than hydroxide and displaces hydroxyl from oxyanions e.g. forming perborates and percarbonates. Sodium perborate and sodium percarbonate are important consumer and industrial bleaching agents; they stabilize hydrogen peroxide and limit side reactions (e.g. reduction and decomposition note below). The peroxide anion forms an adduct with urea, hydrogen peroxide–urea.
Hydrogen peroxide is both an oxidizing agent and reducing agent. The oxidation of hydrogen peroxide by sodium hypochlorite yields singlet oxygen. The net reaction of a ferric ion with hydrogen peroxide is a ferrous ion and oxygen. This proceeds via single electron oxidation and hydroxyl radicals. This is used in some organic chemistry oxidations, e.g. in the Fenton's reagent. Only catalytic quantities of iron ion is needed since peroxide also oxidizes ferrous to ferric ion. The net reaction of hydrogen peroxide and permanganate or manganese dioxide is manganous ion; however, until the peroxide is spent some manganous ions are reoxidized to make the reaction catalytic. This forms the basis for common monopropellant rockets.
Biological function[edit]
Ascaridole
Hydrogen peroxide is formed in human and animals as a short-lived product in biochemical processes and is toxic to cells. The toxicity is due to oxidation of proteins, membrane lipids and DNA by the peroxide ions.[28] The class of biological enzymes called SOD (superoxide dismutase) is developed in nearly all living cells as an important antioxidant agent. They promote the disproportionation of superoxide into oxygen and hydrogen peroxide, which is then rapidly decomposed by the enzyme catalase to oxygen and water.[29]
2 O 2 − + 2 H + → SOD H 2 O 2 ⏞ + hydrogen peroxide O 2 ⏞ oxygen {\displaystyle {\ce {{2O2^{-}}+2H+->[{\ce {SOD}}]\overbrace {H2O2} ^{hydrogen\ peroxide}+\overbrace {O2} ^{oxygen}}}}
Formation of hydrogen peroxide by superoxide dismutase (SOD)
Peroxisomes are organelles found in virtually all eukaryotic cells.[30] They are involved in the catabolism of very long chain fatty acids, branched chain fatty acids, D-amino acids, polyamines, and biosynthesis of plasmalogens, etherphospholipids critical for the normal function of mammalian brains and lungs.[31] Upon oxidation, they produce hydrogen peroxide in the following process:[32]
R − CH 2 − CH 2 − CO − SCoA + O 2 → FAD R − CH = CH − CO − SCoA + H 2 O 2 ⏞ hydrogen peroxide {\displaystyle {\ce {{R-CH2-CH2-CO-SCoA}+O2->[{\ce {FAD}}]{R-CH=CH-CO-SCoA}+\overbrace {H2O2} ^{hydrogen\ peroxide}}}}
FAD = flavin adenine dinucleotide
Catalase, another peroxisomal enzyme, uses this H2O2 to oxidize other substrates, including phenols, formic acid, formaldehyde, and alcohol, by means of the peroxidation reaction:
H 2 O 2 + R ′ H 2 ⟶ R ′ + 2 H 2 O {\displaystyle {\ce {{H2O2}+ R'H2 -> {R'}+ 2H2O}}} , thus eliminating the poisonous hydrogen peroxide in the process.
This reaction is important in liver and kidney cells, where the peroxisomes neutralize various toxic substances that enter the blood. Some of the ethanol humans drink is oxidized to acetaldehyde in this way.[33] In addition, when excess H2O2 accumulates in the cell, catalase converts it to H2O through this reaction:
H 2 O 2 ⏞ → CAT hydrogen peroxide 1 2 O 2 + H 2 O {\displaystyle {\ce {\overbrace {H2O2} ^{hydrogen\ peroxide}->[{\ce {CAT}}]{1/2O2}+H2O}}}
Another origin of hydrogen peroxide is the degradation of adenosine monophosphate which yields hypoxanthine. Hypoxanthine is then oxidatively catabolized first to xanthine and then to uric acid, and the reaction is catalyzed by the enzyme xanthine oxidase:[34]
Degradation of hypoxanthine to uric acid to form hydrogen peroxide. XO = xanthinoxidase
Australian bombardier beetle
The degradation of guanosine monophosphate yields xanthine as an intermediate product which is then converted in the same way to uric acid with the formation of hydrogen peroxide.[34]
Eggs of sea urchin, shortly after fertilization by a sperm, produce hydrogen peroxide. It is then quickly dissociated to OH· radicals. The radicals serve as initiator of radical polymerization, which surrounds the eggs with a protective layer of polymer.[35]
The bombardier beetle has a device which allows it to shoot corrosive and foul-smelling bubbles at its enemies. The beetle produces and stores hydroquinone and hydrogen peroxide, in two separate reservoirs in the rear tip of its abdomen. When threatened, the beetle contracts muscles that force the two reactants through valved tubes into a mixing chamber containing water and a mixture of catalytic enzymes. When combined, the reactants undergo a violent exothermic chemical reaction, raising the temperature to near the boiling point of water. The boiling, foul-smelling liquid partially becomes a gas (flash evaporation) and is expelled through an outlet valve with a loud popping sound.[36][37][38]
Hydrogen peroxide is a signaling molecule of plant defense against pathogens.[39]
Hydrogen peroxide has roles as a signalling molecule in the regulation of a wide variety of biological processes.[40] The compound is a major factor implicated in the free-radical theory of aging, based on how readily hydrogen peroxide can decompose into a hydroxyl radical and how superoxide radical byproducts of cellular metabolism can react with ambient water to form hydrogen peroxide.[41] These hydroxyl radicals in turn readily react with and damage vital cellular components, especially those of the mitochondria.[42][43][44] At least one study has also tried to link hydrogen peroxide production to cancer.[45] These studies have frequently been quoted in fraudulent treatment claims.[citation needed]
The amount of hydrogen peroxide in biological systems can be assayed using a fluorimetric assay.[46]
Uses[edit]
Bleaching[edit]
About 60% of the world's production of hydrogen peroxide is used for pulp- and paper-bleaching.[22]
Detergents[edit]
The second major industrial application is the manufacture of sodium percarbonate and sodium perborate, which are used as mild bleaches in laundry detergents. Sodium percarbonate, which is an adduct of sodium carbonate and hydrogen peroxide, is the active ingredient in such products as OxiClean and Tide laundry detergent. When dissolved in water, it releases hydrogen peroxide and sodium carbonate:[47]
2 Na 2 CO 3 ⋅ 3 2 H 2 O 2 ⟶ 2 Na 2 CO 3 + 3 H 2 O 2 {\displaystyle {\ce {2Na2CO3.3/2H2O2 -> {2Na2CO3}+ 3 H2O2}}}
Production of organic compounds[edit]
It is used in the production of various organic peroxides with dibenzoyl peroxide being a high volume example. It is used in polymerisations, as a flour bleaching agent and as a treatment for acne. Peroxy acids, such as peracetic acid and meta-chloroperoxybenzoic acid are also produced using hydrogen peroxide. Hydrogen peroxide has been used for creating organic peroxide-based explosives, such as acetone peroxide.
Disinfectant[edit]
Skin shortly after exposure to 35% H
2O
2
Hydrogen peroxide is used in certain waste-water treatment processes to remove organic impurities. In advanced oxidation processing, the Fenton reaction[48][49] gives highly reactive ·OH. These hydroxyl radicals degrade organic compounds, including those that are ordinarily robust, such as aromatic or halogenated compounds.[50] It can also oxidize sulfur based compounds present in the waste; which is beneficial as it generally reduces their odour.[51]
Hydrogen peroxide can be used for the sterilization of various surfaces,[52] including surgical tools[53] and may be deployed as a vapour (VHP) for room sterilization.[54] H2O2 demonstrates broad-spectrum efficacy against viruses, bacteria, yeasts, and bacterial spores.[55] In general, greater activity is seen against Gram-positive than Gram-negative bacteria; however, the presence of catalase or other peroxidases in these organisms can increase tolerance in the presence of lower concentrations.[56] Higher concentrations of H2O2 (10 to 30%) and longer contact times are required for sporicidal activity.[57]
Hydrogen peroxide is seen as an environmentally safe alternative to chlorine-based bleaches, as it degrades to form oxygen and water and it is generally recognized as safe as an antimicrobial agent by the U.S. Food and Drug Administration (FDA).[58]
Historically hydrogen peroxide was used for disinfecting wounds, partly because of its low cost and prompt availability compared to other antiseptics. It is now thought to inhibit healing and to induce scarring because it destroys newly formed skin cells.[59] Only a very low concentration of H2O2 can induce healing, and only if not repeatedly applied.[60] Surgical use can lead to gas embolism formation.[61][62] Despite this it is still used for wound treatment in many developing countries.[63][64]
Dermal exposure to dilute solutions of hydrogen peroxide cause whitening or bleaching of the skin due to microembolism caused by oxygen bubbles in the capillaries.[65]
Cosmetic applications[edit]
Diluted H
2O
2 (between 1.9% and 12%) mixed with ammonium hydroxide is used to bleach human hair. The chemical's bleaching property lends its name to the phrase "peroxide blonde".[66] Hydrogen peroxide is also used for tooth whitening. It can be found in most whitening toothpastes. Hydrogen peroxide has shown positive results involving teeth lightness and chroma shade parameters. It works by oxidizing colored pigments onto the enamel where the shade of the tooth can indeed become lighter. Hydrogen peroxide can be mixed with baking soda and salt to make a home-made toothpaste.[67]
Hydrogen peroxide may be used to treat acne,[68] although benzoyl peroxide is a more common treatment.
Use in alternative medicine[edit]
Practitioners of alternative medicine have advocated the use of hydrogen peroxide for various conditions, including emphysema, influenza, AIDS and cancer,[69] although there is no evidence of effectiveness and in some cases it may even be fatal.[70][71][72][73][74]
The practice calls for the daily consumption of hydrogen peroxide, either orally or by injection and is, in general, based around two precepts. First, that hydrogen peroxide is naturally produced by the body to combat infection; and second, that human pathogens (including cancer: See Warburg hypothesis) are anaerobic and cannot survive in oxygen-rich environments. The ingestion or injection of hydrogen peroxide is therefore believed to kill disease by mimicking the immune response in addition to increasing levels of oxygen within the body. This makes it similar to other oxygen-based therapies, such as ozone therapy and hyperbaric oxygen therapy.
Both the effectiveness and safety of hydrogen peroxide therapy is scientifically questionable. Hydrogen peroxide is produced by the immune system but in a carefully controlled manner. Cells called phagocytes engulf pathogens and then use hydrogen peroxide to destroy them. The peroxide is toxic to both the cell and the pathogen and so is kept within a special compartment, called a phagosome. Free hydrogen peroxide will damage any tissue it encounters via oxidative stress; a process which also has been proposed as a cause of cancer.[75] Claims that hydrogen peroxide therapy increase cellular levels of oxygen have not been supported. The quantities administered would be expected to provide very little additional oxygen compared to that available from normal respiration. It should also be noted that it is difficult to raise the level of oxygen around cancer cells within a tumour, as the blood supply tends to be poor, a situation known as tumor hypoxia.
Large oral doses of hydrogen peroxide at a 3% concentration may cause irritation and blistering to the mouth, throat, and abdomen as well as abdominal pain, vomiting, and diarrhea.[70] Intravenous injection of hydrogen peroxide has been linked to several deaths.[72][73][74]
The American Cancer Society states that "there is no scientific evidence that hydrogen peroxide is a safe, effective or useful cancer treatment."[71] Furthermore, the therapy is not approved by the U.S. FDA.
Propellant[edit]
For more details on this topic, see High-test peroxide.
Rocket-belt hydrogen-peroxide propulsion system used in a jet pack
High-concentration H
2O
2 is referred to as "high-test peroxide" (HTP). It can be used either as a monopropellant (not mixed with fuel) or as the oxidizer component of a bipropellant rocket. Use as a monopropellant takes advantage of the decomposition of 70–98% concentration hydrogen peroxide into steam and oxygen. The propellant is pumped into a reaction chamber, where a catalyst, usually a silver or platinum screen, triggers decomposition, producing steam at over 600 °C (1,112 °F), which is expelled through a nozzle, generating thrust. H
2O
2 monopropellant produces a maximal specific impulse (Isp) of 161 s (1.6 kN·s/kg). Peroxide was the first major monopropellant adopted for use in rocket applications. Hydrazine eventually replaced hydrogen-peroxide monopropellant thruster applications primarily because of a 25% increase in the vacuum specific impulse.[76] Hydrazine (toxic) and hydrogen peroxide (less-toxic [ACGIH TLV 0.01 and 1 ppm respectively]) are the only two monopropellants (other than cold gases) to have been widely adopted and utilized for propulsion and power applications. The Bell Rocket Belt, reaction-control systems for X-1, X-15, Centaur, Mercury, Little Joe, as well as the turbo-pump gas generators for X-1, X-15, Jupiter, Redstone and Viking used hydrogen peroxide as a monopropellant.[77]
As a bipropellant, H
2O
2 is decomposed to burn a fuel as an oxidizer. Specific impulses as high as 350 s (3.5 kN·s/kg) can be achieved, depending on the fuel. Peroxide used as an oxidizer gives a somewhat lower Isp than liquid oxygen, but is dense, storable, noncryogenic and can be more easily used to drive gas turbines to give high pressures using an efficient closed cycle. It can also be used for regenerative cooling of rocket engines. Peroxide was used very successfully as an oxidizer in World War II German rocket motors (e.g. T-Stoff, containing oxyquinoline stabilizer, for both the Walter HWK 109-500 Starthilfe RATO externally podded monopropellant booster system, and for the Walter HWK 109-509 rocket motor series used for the Me 163B), most often used with C-Stoff in a self-igniting hypergolic combination, and for the low-cost British Black Knight and Black Arrow launchers.
In the 1940s and 1950s, the Hellmuth Walter KG-conceived turbine used hydrogen peroxide for use in submarines while submerged; it was found to be too noisy and require too much maintenance compared to diesel-electric power systems. Some torpedoes used hydrogen peroxide as oxidizer or propellant. Operator error in the use of hydrogen-peroxide torpedoes was named as possible causes for the sinkings of HMS Sidon and the Russian submarine Kursk.[78] SAAB Underwater Systems is manufacturing the Torpedo 2000. This torpedo, used by the Swedish Navy, is powered by a piston engine propelled by HTP as an oxidizer and kerosene as a fuel in a bipropellant system.[79][80]
Other uses[edit]
Chemiluminescence of cyalume, as found in a glow stick
Hydrogen peroxide has various domestic uses, primarily as a cleaning and disinfecting agent.
Glow sticks
Hydrogen peroxide reacts with certain di-esters, such as phenyl oxalate ester (cyalume), to produce chemiluminescence; this application is most commonly encountered in the form of glow sticks.
Horticulture
Some horticulturalists and users of hydroponics advocate the use of weak hydrogen peroxide solution in watering solutions. Its spontaneous decomposition releases oxygen that enhances a plant's root development and helps to treat root rot (cellular root death due to lack of oxygen) and a variety of other pests.[81][82]
Fish aeration
Laboratory tests conducted by fish culturists in recent years have demonstrated that common household hydrogen peroxide can be used safely to provide oxygen for small fish. The hydrogen peroxide releases oxygen by decomposition when it is exposed to catalysts such as manganese dioxide.
Safety[edit]
Regulations vary, but low concentrations, such as 6%, are widely available and legal to buy for medical use. Most over-the-counter peroxide solutions are not suitable for ingestion. Higher concentrations may be considered hazardous and are typically accompanied by a Material Safety Data Sheet (MSDS). In high concentrations, hydrogen peroxide is an aggressive oxidizer and will corrode many materials, including human skin. In the presence of a reducing agent, high concentrations of H
2O
2 will react violently.
High-concentration hydrogen peroxide streams, typically above 40%, should be considered hazardous due to concentrated hydrogen peroxide's meeting the definition of a DOT oxidizer according to U.S. regulations, if released into the environment. The EPA Reportable Quantity (RQ) for D001 hazardous wastes is 100 pounds (45 kg), or approximately 10 US gallons (38 L), of concentrated hydrogen peroxide.
Hydrogen peroxide should be stored in a cool, dry, well-ventilated area and away from any flammable or combustible substances. It should be stored in a container composed of non-reactive materials such as stainless steel or glass (other materials including some plastics and aluminium alloys may also be suitable).[83] Because it breaks down quickly when exposed to light, it should be stored in an opaque container, and pharmaceutical formulations typically come in brown bottles that block light.[84]
Hydrogen peroxide, either in pure or diluted form, can pose several risks, the main one being that it forms explosive mixtures upon contact with organic compounds.[85] Highly concentrated hydrogen peroxide itself is unstable and can cause a boiling liquid expanding vapour explosion (BLEVE) of the remaining liquid. Distillation of hydrogen peroxide at normal pressures is thus highly dangerous. It is also corrosive, especially when concentrated, but even domestic-strength solutions can cause irritation to the eyes, mucous membranes and skin.[86] Swallowing hydrogen peroxide solutions is particularly dangerous, as decomposition in the stomach releases large quantities of gas (10 times the volume of a 3% solution), leading to internal bloating. Inhaling over 10% can cause severe pulmonary irritation.[87]
With a significant vapour pressure (1.2 kPa at 50 °C[88]), hydrogen-peroxide vapour is potentially hazardous. According to U.S. NIOSH, the immediately dangerous to life and health (IDLH) limit is only 75 ppm.[89] The U.S. Occupational Safety and Health Administration (OSHA) has established a permissible exposure limit of 1.0 ppm calculated as an 8-hour time-weighted average (29 CFR 1910.1000, Table Z-1).[85] Hydrogen peroxide has also been classified by the American Conference of Governmental Industrial Hygienists (ACGIH) as a "known animal carcinogen, with unknown relevance on humans".[90] For workplaces where there is a risk of exposure to the hazardous concentrations of the vapours, continuous monitors for hydrogen peroxide should be used. Information on the hazards of hydrogen peroxide is available from OSHA[85] and from the ATSDR.[91]
Historical incidents[edit]
On 16 July 1934, in Kummersdorf, Germany, a propellant tank containing an experimental monopropellant mixture consisting of hydrogen peroxide and ethanol exploded during a test, killing three people.
During the Second World War, doctors in German concentration camps experimented with the use of hydrogen peroxide injections in the killing of human subjects.[92]
Several people received minor injuries after a hydrogen peroxide spill on board a flight between the U.S. cities of Orlando and Memphis on 28 October 1998.[93]
The Russian submarine K-141 Kursk sailed to perform an exercise of firing dummy torpedoes at the Pyotr Velikiy, a Kirov-class battlecruiser. On 12 August 2000, at 11:28 local time (07:28 UTC), there was an explosion while preparing to fire the torpedoes. The only credible report to date is that this was due to the failure and explosion of one of the Kursk's hydrogen peroxide-fueled torpedoes. It is believed that HTP, a form of highly concentrated hydrogen peroxide used as propellant for the torpedo, seeped through its container, damaged either by rust or in the loading procedure back on land where an incident involving one of the torpedoes accidentally touching ground went unreported. The vessel was lost with all hands. A similar incident was responsible for the loss of HMS Sidon in 1955.
On 15 August 2010, a spill of about 30 US gallons (110 L) of cleaning fluid occurred on the 54th floor of 1515 Broadway, in Times Square, New York City. The spill, which a spokesperson for the New York City fire department said was of hydrogen peroxide, shut down Broadway between West 42nd and West 48th streets as fire engines responded to the hazmat situation. There were no reported injuries.[94]
See also[edit]
FOX reagent, used to measure levels of hydrogen peroxide in biological systems.
Hydrogen chalcogenide
References[edit]
Notes
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In 1882, Kingzett proposed as a structure H2O=O. See: Thomas Kingzett, Charles (29 September 1882). "On the activity of oxygen and the mode of formation of hydrogen dioxide". The Chemical News. 46 (1192): 141–142.
In his 1922 textbook, Joseph Mellor considered three hypothetical molecular structures for hydrogen peroxide, admitting (p. 952): "... the constitution of this compound has not been yet established by unequivocal experiments". See: Joseph William Mellor, A Comprehensive Treatise on Inorganic and Theoretical Chemistry, vol. 1 (London, England: Longmans, Green and Co., 1922), p. 952–956.
W. C. Schumb, C. N. Satterfield, and R. L. Wentworth (1 December 1953) "Report no. 43: Hydrogen peroxide, Part two", Office of Naval Research, Contract No. N5ori-07819 On p. 178, the authors present six hypothetical models for hydrogen peroxide's molecular structure. On p. 184, the present structure is considered almost certainly correct—although a small doubt remained. (Note: The report by Schumb et al. was reprinted as: W. C. Schumb, C. N. Satterfield, and R. L. Wentworth, Hydrogen Peroxide (New York, New York: Reinhold Publishing Corp. (American Chemical Society Monograph), 1955).)
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Penney, W. G.; Sutherland, G. B. B. M. (1934). "A note on the structure of H2O2 and H4N2 with particular reference to electric moments and free rotation". Transactions of the Faraday Society. 30: 898–902.
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2O
2.
J. March (1992). Advanced Organic Chemistry (4th ed.). New York: Wiley. p. 723.
W.T. Hess (1995). "Hydrogen Peroxide". Kirk-Othmer Encyclopedia of Chemical Technology. 13 (4th ed.). New York: Wiley. pp. 961–995.
External links[edit]
Hydrogen Peroxide at The Periodic Table of Videos (University of Nottingham)
Material Safety Data Sheet
ATSDR Agency for Toxic Substances and Disease Registry FAQ
International Chemical Safety Card 0164
NIOSH Pocket Guide to Chemical Hazards
Process flow sheet of Hydrogen Peroxide Production by anthrahydroquinone autoxidation
Hydrogen Peroxide Handbook by Rocketdyne
[show]
v
t
e
Hydrogen compounds
H3AsO3
H3AsO4
HAt
HSO3F
HBF4
HBr
HBrO
HBrO2
HBrO3
HBrO4
HCl
HClO
HClO2
HClO3
HClO4
HCN
HCNO
H2CrO4/H2Cr2O7
H2CO3
H2CS3
HF
HFΟ
HI
HIO
HIO2
HIO3
HIO4
HMnO4
H2MoO4
HNC
NaHCO3
HNCO
HNO
HNO2
HNO3
H2N2O2
HNO5S
H3NSO3
H2O
H2O2
H2O3
H3PO2
H3PO3
H3PO4
H4P2O7
H5P3O10
H2PtCl6
H2S
H2S2
H2Se
H2SeO3
H2SeO4
H4SiO4
H2SiF6
HSCN
HNSC
H2SO3
H2SO4
H2SO5
H2S2O3
H2S2O6
H2S2O7
H2S2O8
CF3SO3H
H2Te
H2TeO3
H6TeO6
H4TiO4
H2Po
HCo(CO)4
[show]
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Antiseptics and disinfectants (D08)
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Chlorhexidine#
Propamidine
Hexamidine
Polihexanide
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Hexachlorophene
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Phenol
Triclosan
Triclocarban
Chloroxylenol#
Biphenylol
Fenticlor
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Nitrofurazone
Iodine products
Iodine/octylphenoxypolyglycolether
Povidone-iodine#
Diiodohydroxypropane
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Chlorquinaldol
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Silver compounds
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Ethanol (ethyl alcohol)#
Other
Potassium permanganate
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Eosin
Tosylchloramide
Octenidine dihydrochloride
#WHO-EM
‡Withdrawn from market
Clinical trials:
†Phase III
§Never to phase III
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[show]
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Molecules detected in outer space
Molecules
Diatomic
Aluminium monochloride
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Argonium
Carbon monophosphide
Carbon monosulfide
Carbon monoxide
Carborundum
Cyanogen radical
Diatomic carbon
Fluoromethylidynium
Hydrogen chloride
Hydrogen fluoride
Hydrogen (molecular)
Hydroxyl radical
Iron(II) oxide
Magnesium monohydride cation
Methylidyne radical
Nitric oxide
Nitrogen (molecular)
Nitrogen monohydride
Nitrogen sulfide
Oxygen (molecular)
Phosphorus monoxide
Phosphorus mononitride
Potassium chloride
Silicon carbide
Silicon mononitride
Silicon monoxide
Silicon monosulfide
Sodium chloride
Sodium iodide
Sulfur monohydride
Sulfur monoxide
Titanium oxide
Triatomic
Aluminium hydroxide
Aluminium isocyanide
Amino radical
Carbon dioxide
Carbonyl sulfide
CCP radical
Chloronium
Diazenylium
Dicarbon monoxide
Disilicon carbide
Ethynyl radical
Formyl radical
Hydrogen cyanide (HCN)
Hydrogen isocyanide (HNC)
Hydrogen sulfide
Hydroperoxyl
Iron cyanide
Isoformyl
Magnesium cyanide
Magnesium isocyanide
Methylene radical
N2H+
Nitrous oxide
Nitroxyl
Ozone
Phosphaethyne
Potassium cyanide
Protonated molecular hydrogen
Sodium cyanide
Sodium hydroxide
Silicon carbonitride
c-Silicon dicarbide
Silicon naphthalocyanine
Sulfur dioxide
Thioformyl
Thioxoethenylidene
Titanium dioxide
Tricarbon
Water
Four
atoms
Acetylene
Ammonia
Cyanic acid
Cyanoethynyl
Cyclopropynylidyne
Formaldehyde
Fulminic acid
HCCN
Hydrogen peroxide
Hydromagnesium isocyanide
Isocyanic acid
Isothiocyanic acid
Ketenyl
Methylene amidogen
Methyl radical
Propynylidyne
Protonated carbon dioxide
Protonated hydrogen cyanide
Silicon tricarbide
Thioformaldehyde
Tricarbon monoxide
Tricarbon sulfide
Thiocyanic acid
Five
atoms
Ammonium ion
Butadiynyl
Carbodiimide
Cyanamide
Cyanoacetylene
Cyanoformaldehyde
Cyanomethyl
Cyclopropenylidene
Formic acid
Isocyanoacetylene
Ketene
Methane
Methoxy radical
Methylenimine
Propadienylidene
Protonated formaldehyde
Protonated formaldehyde
Silane
Silicon-carbide cluster
Six
atoms
Acetonitrile
Cyanobutadiynyl radical
E-Cyanomethanimine
Cyclopropenone
Diacetylene
Ethylene
Formamide
HC4N
Ketenimine
Methanethiol
Methanol
Methyl isocyanide
Pentynylidyne
Propynal
Protonated cyanoacetylene
Seven
atoms
Acetaldehyde
Acrylonitrile
Vinyl cyanide
Cyanodiacetylene
Ethylene oxide
Hexatriynyl radical
Methylacetylene
Methylamine
Methyl isocyanate
Vinyl alcohol
Eight
atoms
Acetic acid
Aminoacetonitrile
Cyanoallene
Ethanimine
Glycolaldehyde
Heptatrienyl radical
Hexapentaenylidene
Methylcyanoacetylene
Methyl formate
Propenal
Nine
atoms
Acetamide
Cyanohexatriyne
Cyanotriacetylene
Dimethyl ether
Ethanol
Methyldiacetylene
Octatetraynyl radical
Propene
Propionitrile
Ten
atoms
or more
Acetone
Benzene
Buckminsterfullerene (C60 fullerene, buckyball)
C70 fullerene
Cyanodecapentayne
Cyanopentaacetylene
Cyanotetra-acetylene
Ethylene glycol
Ethyl formate
Methyl acetate
Methyl-cyano-diacetylene
Methyltriacetylene
Propanal
n-Propyl cyanide
Pyrimidine
Deuterated
molecules
Ammonia
Ammonium ion
Formaldehyde
Formyl radical
Heavy water
Hydrogen cyanide
Hydrogen deuteride
Hydrogen isocyanide
Methylacetylene
N2D+
Trihydrogen cation
Unconfirmed
Anthracene
Dihydroxyacetone
Ethyl methyl ether
Glycine
Graphene
H2NCO+
Linear C5
Naphthalene cation
Phosphine
Pyrene
Silylidine
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Tholin
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[show]
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Oxygen compounds
AgO
Al2O3
AmO2
Am2O3
As2O3
As2O5
Au2O3
B2O3
BaO
BeO
Bi2O3
BiO2
Bi2O5
BrO2
Br2O3
Br2O5
CO
CO2
C2O3
CaO
CaO2
CdO
CeO2
Ce3O4
Ce2O3
ClO2
Cl2O
Cl2O3
Cl2O4
Cl2O6
Cl2O7
CoO
Co2O3
Co3O4
CrO3
Cr2O3
Cr2O5
Cr5O12
CsO2
Cs2O3
CuO
D2O
Dy2O3
Er2O3
Eu2O3
F2O
F2O2
F2O4
FeO
Fe2O3
Fe3O4
Ga2O
Ga2O3
GeO
GeO2
H2O
H218O
H2O2
HfO2
HgO
Hg2O
Ho2O3
I2O4
I2O5
I2O6
I4O9
In2O3
InO2
KO2
K2O2
La2O3
Li2O
Li2O2
Lu2O3
MgO
Mg2O3
MnO
MnO2
Mn2O3
Mn2O7
MoO2
MoO3
Mo2O3
NO
NO2
N2O
N2O3
N2O4
N2O5
NaO2
Na2O
Na2O2
NbO
NbO2
Nd2O3
Chemical formulas
[show]
v
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TRP channel modulators
TRPA
Activators
4-Hydroxynonenal
4-Oxo-2-nonenal
4,5-EET
12S-HpETE
15-Deoxy-Δ12,14-prostaglandin J2
α-Sanshool (ginger, Sichuan and melegueta peppers)
Acrolein
Allicin (garlic)
Allyl isothiocyanate (mustard, radish, horseradish, wasabi)
AM404
Bradykinin
Cannabichromene (cannabis)
Cannabidiol (cannabis)
Cannabigerol (cannabis)
Cinnamaldehyde (cinnamon)
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Curcumin (turmeric)
Dehydroligustilide (celery)
Diallyl disulfide
Dicentrine (Lindera spp.)
Farnesyl thiosalicylic acid
Formalin
Gingerols (ginger)
Hepoxilin A3
Hepoxilin B3
Hydrogen peroxide
Icilin
Isothiocyanate
Ligustilide (celery, Angelica acutiloba)
Linalool (Sichuan pepper, thyme)
Methylglyoxal
Methyl salicylate (wintergreen)
N-Methylmaleimide
Nicotine (tobacco)
Oleocanthal (olive oil)
Paclitaxel (Pacific yew)
Paracetamol (acetaminophen)
PF-4840154
Phenacyl chloride
Polygodial (Dorrigo pepper)
Shogaols (ginger, Sichuan and melegueta peppers)
Tear gases
Tetrahydrocannabinol (cannabis)
Thiopropanal S-oxide (onion)
Umbellulone (Umbellularia californica)
WIN 55,212-2
Blockers
Dehydroligustilide (celery)
Nicotine (tobacco)
Ruthenium red
TRPC
Activators
Adhyperforin (St John's wort)
Diacyl glycerol
GSK1702934A
Hyperforin (St John's wort)
Substance P
Blockers
DCDPC
DHEA-S
Flufenamic acid
GSK417651A
GSK2293017A
Meclofenamic acid
N-(p-amylcinnamoyl)anthranilic acid
Niflumic acid
Pregnenolone sulfate
Progesterone
Pyr3
Tolfenamic acid
TRPM
Activators
ADP-ribose
BCTC
Calcium (intracellular)
Cold
Coolact P
Cooling Agent 10
CPS-369
Eucalyptol (eucalyptus)
Frescolat MGA
Frescolat ML
Geraniol
Hydroxycitronellal
Icilin
Linalool
Menthol (mint)
PMD 38
Pregnenolone sulfate
Rutamarin (Ruta graveolens)
Steviol glycosides (e.g., stevioside) (Stevia rebaudiana)
Sweet tastants (e.g., glucose, fructose, sucrose; indirectly)
Thio-BCTC
WS-3
WS-12
WS-23
Blockers
Capsazepine
Clotrimazole
DCDPC
Flufenamic acid
Meclofenamic acid
Mefenamic acid
N-(p-amylcinnamoyl)anthranilic acid
Nicotine (tobacco)
Niflumic acid
Ruthenium red
Rutamarin (Ruta graveolens)
Tolfenamic acid
TPPO
TRPML
Activators
MK6-83
PI(3,5)P2
SF-22
TRPP
Activators
Triptolide (Tripterygium wilfordii)
Blockers
Ruthenium red
TRPV
Activators
2-APB
5',6'-EET
9-HODE
9-oxoODE
12S-HETE
12S-HpETE
13-HODE
13-oxoODE
20-HETE
α-Sanshool (ginger, Sichuan and melegueta peppers)
Allicin (garlic)
AM404
Anandamide
Bisandrographolide (Andrographis paniculata)
Camphor (camphor laurel, rosemary, camphorweed, African blue basil, camphor basil)
Cannabidiol (cannabis)
Cannabidivarin (cannabis)
Capsaicin (chili pepper)
Carvacrol (oregano, thyme, pepperwort, wild bergamot, others)
DHEA
Diacyl glycerol
Dihydrocapsaicin (chili pepper)
Estradiol
Eugenol (basil, clove)
Evodiamine (Euodia ruticarpa)
Gingerols (ginger)
GSK1016790A
Heat
Hepoxilin A3
Hepoxilin B3
Homocapsaicin (chili pepper)
Homodihydrocapsaicin (chili pepper)
Incensole (incense)
Lysophosphatidic acid
Low pH (acidic conditions)
Menthol (mint)
N-Arachidonoyl dopamine
N-Oleoyldopamine
N-Oleoylethanolamide
Nonivamide (PAVA) (PAVA spray)
Nordihydrocapsaicin (chili pepper)
Paclitaxel (Pacific yew)
Paracetamol (acetaminophen)
Phorbol esters (e.g., 4α-PDD)
Piperine (black pepper, long pepper)
Polygodial (Dorrigo pepper)
Probenecid
Protons
Rutamarin (Ruta graveolens)
Resiniferatoxin (RTX) (Euphorbia resinifera/pooissonii)
Shogaols (ginger, Sichuan and melegueta peppers)
Tetrahydrocannabivarin (cannabis)
Thymol (thyme, oregano)
Tinyatoxin (Euphorbia resinifera/pooissonii)
Tramadol
Vanillin (vanilla)
Zucapsaicin
Blockers
α-Spinasterol (Vernonia tweediana)
AMG-517
Asivatrep
BCTC
Cannabigerol (cannabis)
Cannabigerolic acid (cannabis)
Cannabigerovarin (cannabis)
Cannabinol (cannabis)
Capsazepine
DCDPC
DHEA
DHEA-S
Flufenamic acid
GRC-6211
HC-067047
Lanthanum
Meclofenamic acid
N-(p-amylcinnamoyl)anthranilic acid
NGD-8243
Niflumic acid
Pregnenolone sulfate
RN-1734
RN-9893
Ruthenium red
SB-705498
Tolfenamic acid
See also: Receptor/signaling modulators • Ion channel modulators
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Structural formula of hydrogen peroxide

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GHS hazard statement

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abbr
Causes severe skin burns and eye damage

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