solventsorganic solventorganic solvents
Ethers like diethyl ether and tetrahydrofuran (THF) can form highly explosive organic peroxides upon exposure to oxygen and light. THF is normally more likely to form such peroxides than diethyl ether. One of the most susceptible solvents is diisopropyl ether, but all ethers are considered to be potential peroxide sources. The heteroatom (oxygen) stabilizes the formation of a free radical which is formed by the abstraction of a hydrogen atom by another free radical. The carbon-centred free radical thus formed is able to react with an oxygen molecule to form a peroxide compound.

Skeletal formula

representedskeletal structureskeleton
TMS, TBDMS, TES, TBDPS, TIPS, ... for various silyl ether groups. PMB for the 4-methoxybenzyl group. MOM for the methoxymethyl group. THP for the 2-tetrahydropyranyl group. Solid lines represent bonds in the plane of the paper or screen. Solid wedges represent bonds that point out of the plane of the paper or screen, towards the observer. Hashed wedges or dashed lines (thick or thin) represent bonds that point into the plane of the paper or screen, away from the observer. Wavy lines represent either unknown stereochemistry or a mixture of the two possible stereoisomers at that point.


alcoholbioethanolethyl alcohol
Ethanol is a versatile solvent, miscible with water and with many organic solvents, including acetic acid, acetone, benzene, carbon tetrachloride, chloroform, diethyl ether, ethylene glycol, glycerol, nitromethane, pyridine, and toluene. It is also miscible with light aliphatic hydrocarbons, such as pentane and hexane, and with aliphatic chlorides such as trichloroethane and tetrachloroethylene. Ethanol's miscibility with water contrasts with the immiscibility of longer-chain alcohols (five or more carbon atoms), whose water miscibility decreases sharply as the number of carbons increases.

Glossary of chemical formulae

List of organic compoundsDictionary of chemical formulas
This is a list of common chemical compounds with chemical formulae and CAS numbers, indexed by formula. This complements alternative listing at inorganic compounds by element. There is no complete list of chemical compounds since by nature the list would be infinite.


A simple example of isomerism is given by propanol: It has the formula C 3 H 8 O (or C 3 H 7 OH) and occurs as two isomers: propan-1-ol (n-propyl alcohol; I) and propan-2-ol (isopropyl alcohol; II) These two molecules are position isomers of each other, because the position of the hydroxy group differs between the two: It is attached to an end carbon in the first isomer, and to the center carbon in the second. There is also another isomer of C 3 H 8 O that has significantly different properties: methoxyethane (ethyl-methyl-ether; III). Unlike the isomers of propanol, methoxyethane has an oxygen connected to two carbons rather than to one carbon and one hydrogen.

Azeotrope tables

Azeotrope (data)
Azeotropes of isopropanol, b.p.=82.5 °C. {| class="wikitable". colspan="5" align="center" | with various esters. ethyl acetate || 77.1 || 75.3 || 75. bgcolor="#FFFFCC" | 0.869. isopropyl acetate || 91.0 || 81.3 || 40. bgcolor="#FFFFCC" | 0.822. colspan="5" align="center" | with various hydrocarbons. benzene || 80.2 || 71.9 || 66.7. bgcolor="#FFFFCC" | 0.838. - bgcolor="#FFFFCC". toluene ‡ || 110.8 || 80.6 || 42 ||. benzene || 80.2 || 71.9 || 66.7. bgcolor="#FFFFCC" | 0.838. - bgcolor="#FFFFCC". toluene ‡ || 110.8 || 80.6 || 42 ||. - bgcolor="#FFFFCC". cyclohexane || 80.7 || 68.6 || 67.0 || 0.777. - bgcolor="#FFCCFF". n-pentane || 36.2 || 35.5 || 94 ||. n-hexane || 68.9 || 62.7 || 77 ||. - bgcolor

Heat of combustion

calorific valueEnthalpy of combustionlower heating value
The heating value (or energy value or calorific value) of a substance, usually a fuel or food (see food energy), is the amount of heat released during the combustion of a specified amount of it.


MOSCED (short for “modified separation of cohesive energy density model) is a thermodynamic model for the estimation of limiting activity coefficients (also known as activity coefficient at infinite dilution). From a historical point of view MOSCED can be regarded as an improved modification of the Hansen method and the Hildebrand solubility model by adding higher interaction term such as polarity, induction and separation of hydrogen bonding terms. This allows the prediction of polar and associative compounds, which most solubility parameter models have been found to do poorly.

Tert-Butyl alcohol

tert''-butanoltert''-butyl alcoholtert-butanol
tert-Butyl alcohol (TBA), also called tert-butanol or t-butanol, is the simplest tertiary alcohol, with a formula of (CH 3 ) 3 COH (sometimes represented as t-BuOH). It is one of the four isomers of butanol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether. tert-Butyl alcohol has been identified in beer and chickpeas. It is also found in cassava, which is used as a fermentation ingredient in certain alcoholic beverages. tert-Butyl alcohol is derived commercially from isobutane as a coproduct of propylene oxide production.


OO 2 molecular oxygen
There are many important organic solvents that contain oxygen, including: acetone, methanol, ethanol, isopropanol, furan, THF, diethyl ether, dioxane, ethyl acetate, DMF, DMSO, acetic acid, and formic acid. Acetone and phenol are used as feeder materials in the synthesis of many different substances. Other important organic compounds that contain oxygen are: glycerol, formaldehyde, glutaraldehyde, citric acid, acetic anhydride, and acetamide. Epoxides are ethers in which the oxygen atom is part of a ring of three atoms. The element is similarly found in almost all biomolecules that are important to (or generated by) life.

List of MeSH codes (D02)

. --- borohydrides. --- tetraphenylborate. --- acetamides. --- 2-acetylaminofluorene. --- acetoxyacetylaminofluorene. --- hydroxyacetylaminofluorene. --- allylisopropylacetamide. --- iodoacetamide. --- piracetam. --- thioacetamide. --- acetic acid. --- acetates. --- dichloroacetate. --- fluoroacetates. --- iodoacetates. --- potassium acetate. --- sodium acetate. --- thioglycolates. --- zinc acetate. --- acetic anhydrides. --- aminooxyacetic acid. --- edetic acid. --- egtazic acid. --- iodoacetic acid. --- iodoacetamide. --- iodoacetates. --- nitrilotriacetic acid. --- pentetic acid. --- gadolinium dtpa. --- technetium tc 99m pentetate. --- peracetic acid. --- phosphonoacetic acid. --- foscarnet

Flammability limit

lower explosive limitexplosive limitupper explosive limit
Mixtures of dispersed combustible materials (such as gaseous or vaporised fuels, and some dusts) and air will burn only if the fuel concentration lies within well-defined lower and upper bounds determined experimentally, referred to as flammability limits or explosive limits. Combustion can range in violence from deflagration through detonation.

Proton affinity (data page)

Proton affinities are quoted in kJ/mol, in increasing order of gas-phase basicity of the base.

Acetic acid

aceticglacial acetic acidacetate
The three major products are ethylene glycol monoethyl ether acetate (EEA), ethylene glycol monobutyl ether acetate (EBA), and propylene glycol monomethyl ether acetate (PMA, more commonly known as PGMEA in semiconductor manufacturing processes, where it is used as a resist solvent). This application consumes about 15% to 20% of worldwide acetic acid. Ether acetates, for example EEA, have been shown to be harmful to human reproduction. The product of the condensation of two molecules of acetic acid is acetic anhydride. The worldwide production of acetic anhydride is a major application, and uses approximately 25% to 30% of the global production of acetic acid.

Paint thinner

thinnerthinnerspaint thinning
Acetone. Turpentine. Naphtha. Toluene. Methyl ethyl ketone (MEK). Dimethylformamide (DMF). 2-Butoxyethanol, or any of the other glycol ethers. Ethylbenzene. Xylene. n-Butyl acetate. Butanol.


inhalantsinhalant abusesolvent abuse
Several medical anesthetics are used as recreational drugs, including diethyl ether (a drug that is no longer used medically, due to its high flammability and the development of safer alternatives) and nitrous oxide, which is widely used in the 2010s by dentists as an anti-anxiety drug during dental procedures. Diethyl ether has a long history of use as a recreational drug. The effects of ether intoxication are similar to those of alcohol intoxication, but more potent. Also, due to NMDA antagonism, the user may experience all the psychedelic effects present in classical dissociatives such as ketamine in forms of thought loops and feeling of mind being disconnected from one's body.

Isopropyl alcohol

Isopropyl alcohol can be oxidized to acetone, which is the corresponding ketone. This can be achieved using oxidizing agents such as chromic acid, or by dehydrogenation of isopropyl alcohol over a heated copper catalyst: :(CH 3 ) 2 CHOH → (CH 3 ) 2 CO + H 2 Isopropyl alcohol is often used as both solvent and hydride source in the Meerwein-Ponndorf-Verley reduction and other transfer hydrogenation reactions. Isopropyl alcohol may be converted to 2-bromopropane using phosphorus tribromide, or dehydrated to propene by heating with sulfuric acid. Like most alcohols, isopropyl alcohol reacts with active metals such as potassium to form alkoxides that can be called isopropoxides.

Clostridium acetobutylicum

C. acetobutylicumABE fermentationClostridium acetobutylicum'' N1-4081
A senior lecturer at the University of Manchester, England, he used them in 1916 as a bio-chemical tool to produce at the same time, jointly, acetone, ethanol, and butanol from starch. The method has been described since as the ABE process, (Acetone Butanol Ethanol fermentation process), yielding 3 parts of acetone, 6 of butanol, and 1 of ethanol. Acetone was used in the important wartime task of casting cordite. The alcohols were used to produce vehicle fuels and synthetic rubber.

Butanol fuel

Butanol. Catalyst. Dimethyl ether. Distillation. Emission standards. Energy crop. Ethanol fuel. Fermentation facility. Formic acid: can be used as an intermediary to produce isobutanol from CO2 using microbes. Gevo Biofuels. List of vegetable oils used for biofuel. Biobutanol (EERE). Biobutanol research news from Green Car Congress. Butanol 3D view and pdb-file.

Polar solvent

aprotic solventprotic solventaprotic
Other solvents meeting IUPAC's criteria include pyridine, ethyl acetate, DMF, HMPA, and DMSO. Common characteristics of aprotic solvents: The criteria are relative and very qualitative. A range of acidities are recognized for aprotic solvents. Their ability to dissolve salts depends strongly on the nature of the salt. Polar aprotic solvents are generally incompatible with strong bases, such as Grignard reagents or t-butyllithium. These reagents require ethers, not nitriles, amides, sulfoxides, etc. The strong base may even deprotonate them ( such as methyl anion as a base having a pKaH of 50, and sulfoxides have pKa of approximately 35.


etheneC 2 H 4 ethylene gas
ACC synthesis increases with high levels of auxins, especially indole acetic acid (IAA) and cytokinins. Ethylene is perceived by a family of five transmembrane protein dimers such as the ETR1 protein in Arabidopsis. The genes encoding ethylene receptors have been cloned in the reference plant Arabidopsis thaliana and many other plants. Ethylene receptors are encoded by multiple genes in plant genomes. Dominant missense mutations in any of the gene family, which comprises five receptors in Arabidopsis and at least six in tomato, can confer insensitivity to ethylene.


propyleneC 3 H 6 propane dehydrogenation
Propene and benzene are converted to acetone and phenol via the cumene process. Propene is also used to produce isopropanol (propan-2-ol), acrylonitrile, propylene oxide, and epichlorohydrin. The industrial production of acrylic acid involves the catalytic partial oxidation of propene. Propene is also an intermediate in the one-step propane selective oxidation to acrylic acid. In industry and workshops, propene is used as an alternative fuel to acetylene in Oxy-fuel welding and cutting, brazing and heating of metal for the purpose of bending. It has become a standard in BernzOmatic products and others in MAPP substitutes, now that true MAPP gas is no longer available.


hydrogenatedcatalytic hydrogenationhydrogenated vegetable oil
E.g. 1-propanol is produced from propionaldehyde, produced from ethene and carbon monoxide. Xylitol, a polyol, is produced by hydrogenation of the sugar xylose, an aldehyde. Primary amines can be synthesized by hydrogenation of nitriles, while nitriles are readily synthesized from cyanide and a suitable electrophile. For example, isophorone diamine, a precursor to the polyurethane monomer isophorone diisocyanate, is produced from isophorone nitrile by a tandem nitrile hydrogenation/reductive amination by ammonia, wherein hydrogenation converts both the nitrile into an amine and the imine formed from the aldehyde and ammonia into another amine.


The depressant effect on the central nervous system (similar to ethanol intoxication) is a potential hazard when working with n-butanol in enclosed spaces, although the odour threshold (0.2–30 ppm) is far below the concentration which would have any neurological effect. * Butanol fuel. Diethyl ether.

Cellulose acetate

acetateCellonacetate microfilm
The anhydroglucose unit is the fundamental repeating structure of cellulose and has three hydroxyl groups which can react to form acetate esters. The most common form of cellulose acetate fiber has an acetate group on approximately two of every three hydroxyls. This cellulose diacetate is known as secondary acetate, or simply as "acetate". After it is formed, cellulose acetate is dissolved in acetone, forming a viscous solution for extrusion through spinnerets (which resemble a shower head). As the filaments emerge, the solvent is evaporated in warm air via dry spinning, producing fine cellulose acetate fibers.