For other uses, see Solvent (disambiguation). A solvent is a fluid phase (liquid, gas, or plasma) that dissolves a solid, liquid, or gaseous solute, resulting in a solution. The most common solvent in everyday life is water. The term organic solvent refers to most other solvents that are organic compounds and contain carbon atoms. Solvents usually have a low boiling point and evaporate easily or can be removed by distillation, thereby leaving the dissolved substance behind. Solvents should therefore not react chemically with the dissolved compounds — they have to be inert. Solvents can also be used to extract soluble compounds from a mixture, the most common example is the brewing of coffee or tea with hot water. Solvents are usually clear and colorless liquids and most of them have a characteristic odor. The concentration of a solution is the amount of compound that is dissolved in a certain volume of solvent. The solubility is the maximal amount of compound that is soluble in a certain volume of solvent at a specified temperature. Common uses for organic solvents are in dry cleaning (e.g. tetrachloroethylene), as paint thinners (e.g. toluene, turpentine), as nail polish removers and glue solvents (acetone, methyl acetate, ethyl acetate), in spot removers (e.g. hexane, petrol ether), in detergents (citrus terpenes), in perfumes (ethanol), and in chemical syntheses. Contents 1 Polarity, solubility, and miscibility 2 Protic and aprotic solvents 3 Boiling point 4 Density 5 Chemical interactions 6 Health and Safety 6.1 Fire 6.2 Peroxide formation 6.3 Narcotic and other acute health effects 6.4 Environmental contamination 6.5 Chronic health effects 6.5.1 General precautions 7 Properties table of common solvents 8 See also 9 External links Polarity, solubility, and miscibility Solvents and solutes can be broadly classified into polar (hydrophilic) and non-polar (lipophilic). The polarity can be measured as the dielectric constant or the dipole moment of a compound. The polarity of a solvent determines what type of compounds it is able to dissolve and with what other solvents or liquid compounds it is miscible. As a rule of thumb, polar solvents dissolve polar compounds best and non-polar solvents dissolve non-polar compounds best: "like dissolves like". Strongly polar compounds like inorganic salts (e.g. table salt) or sugars (e.g. sucrose) dissolve only in very polar solvents like water, while strongly non-polar compounds like oils or waxes dissolve only in very non-polar organic solvents like hexane. Similarly, water and hexane (or vinegar and salad oil) are not miscible with each other and will quickly separate into two layers even after being shaken well. Protic and aprotic solvents Polar solvents can be further subdivided into polar protic solvents and polar aprotic solvents. Water (H-O-H), ethanol (CH3-CH2-OH), or acetic acid (CH3-C(=O)OH) are representative polar protic solvents. A polar aprotic solvent is acetone (CH3-C(=O)-CH3). In chemical reactions the use of polar protic solvents favors the SN1 reaction mechanism, while polar aprotic solvents favor the SN2 reaction mechanism. Boiling point Another important property of solvents is boiling point. This also determines the speed of evaporation. Small amounts of low-boiling solvents like diethyl ether, dichloromethane, or acetone will evaporate in seconds at room temperature, while high-boiling solvents like water or dimethyl sulfoxide need higher temperatures, an air flow, or the application of vacuum for fast evaporation. Water is a strange exception in this sense, because most solvents of the same size tend to evaporate in very low temperatures. The exception is caused by cohesion i.e., at high temperatures, several water molecules will group together and act as a larger molecule - and evaporate. Density Most organic solvents have a lower density than water, which means they are lighter and will form a separate layer on top of water. An important exception: many halogenated solvents like dichloromethane or chloroform will sink to the bottom of a container, leaving water as the top layer. This is important to remember when partitioning compounds between solvents and water in a separatory funnel during chemical syntheses. Chemical interactions A solvent will create various weak chemical interactions with the solute to solubilize the solute. The most usual of these interactions are the relatively weak van der Waals interactions (induced dipole interactions), the stronger dipole-dipole interactions, and the even stronger hydrogen bonds (interaction between O-H or N-H hydrogens with O or N atoms). Health and Safety Fire Most organic solvents are flammable or highly flammable, depending on their volatility. Exceptions are some chlorinated solvents like dichloromethane and chloroform. Mixtures of solvent vapors and air can explode. Solvent vapors are heavier than air, they will sink to the bottom and can travel large distances nearly undiluted. Solvent vapors can also form in supposedly empty drums and cans, posing a flash fire hazard; hence empty containers of volatile solvents should be stored open and upside down. Both diethyl ether and carbon disulphide have exceptionally low autoignition temperatures which increase greatly the fire risk associated with these solvents. The autoignition temperture of carbon disulphide is below 100 oC, so as a result objects such as steam pipes, light bulbs, hotplates and recently extingished bunsen burners are able to ignite its vapours. Peroxide formation Ethers like diethyl ether and tetrahydrofuran (THF) can form highly explosive organic peroxides upon exposure to oxygen and light, THF is normally more able to form such peroxides than diethyl ether. One of the worst ethers for the formation of peroxides is diisopropyl ether. The effect of the heteroatom (oxygen) is to stabalise the formation of a free radical which is formed by the abstraction of a hydrogen atom by a free radical, the carbon centred free radical this formed is able to react with an oxygen molecule to form a peroxide compound. A range of tests can be used to detect the presense of a peroxide in an ether, one is to use a combination of iron sulphate and potassium thiocyanate. The peroxide is able to oxidize the ferrous ion to a ferric ion which then form a deep red coordination complex with the thiocyanate. In extream cases the peroxides can form crystaline solids within the vessel of the ether. These peroxides will concentrate during distillation due to their higher boiling point (Never distill an ether to dryness), also the peroxide can sometimes form a crystaline (and shock sensitive) solid at the mouth of the bottle it is stored in. It is possible for the peroxide to detonate when the bottle is opened. Ethers have to be stored in the dark in closed canisters in the presence of stabilizers like BHT or over sodium hydroxide. Narcotic and other acute health effects Many solvents can lead to a sudden loss of consciousness if inhaled in larger amounts. Solvents like diethyl ether and chloroform have been used in medicine as anesthetics and narcotics for a long time. Ethanol is a widely used and abused psychoactive drug. Diethyl ether, chloroform, and many other solvents (e.g. from gasoline or glues) are used recreationally in glue sniffing, often with harmful long term health effects like neurotoxicity or cancer. Methanol can cause internal damage to the eyes, including permanent blindness. It is interesting to note that ethanol has a synagistic effect when taken in combination with many solvents. For instance a combination of toluene/benzene and ethanol causes greater nasua/vommiting than either substance alone. Many chemists make a point of not drinking beer/wine/other alcoholic drinks if they know that they have been exposed to an aromatic solvent. Environmental contamination A major pathway to induce health effects arises from spills or leaks of solvents that reach the underlying soil. Since solvents readily migrate substantial distances, the creation of widespread soil contamination is not uncommon; there may be about 5000 sites worldwide that have major subsurface solvent contamination; this is particularly a health risk if aquifers are affected. Chronic health effects Some solvents including chloroform and benzene (an ingredient of gasoline) are carcinogenic. Many others can damage internal organs like the liver, the kidneys, or the brain. General precautions Avoid the generation of solvent vapors by working in a fume hood, local exhaust ventillation (LEV) or a well ventilated area Keep the storage containers tightly closed. Never use open flames near flammable solvents, use electrical heating instead. Never flush flammable solvents down the drain to avoid explosions and fires. Avoid the inhalation of solvent vapors. Avoid contact of the solvent with the skin — many solvents are easily absorbed through the skin. They also tend to dry the skin and thus cause sores and wounds. Properties table of common solvents The solvents are grouped into non-polar, polar aprotic, and polar protic solvents and ordered by increasing polarity. The polarity is given as the dielectric constant. The density of nonpolar solvents that are heavier than water is bolded. Solvent Chemical Formula Boiling point Dielectric constant?? (use the tables linked at the bottom to be safe) Density Non-Polar Solvents Hexane CH3-CH2-CH2-CH2-CH2-CH3 69 °C 2.0 0.655 g/ml Benzene C6H6 80 °C 2.3 0.879 g/ml Toluene C6H5-CH3 111 °C 2.4 0.867 g/ml Diethyl ether CH3CH2-O-CH2-CH3 35 °C 4.3 0.713 g/ml Chloroform CHCl3 61 °C 4.8 1.498 g/ml Ethyl acetate CH3-C(=O)-O-CH2-CH3 77 °C 6.0 0.894 g/ml Dichloromethane CH2Cl2 40 °C 9.1 1.326 g/ml Polar Aprotic Solvents 1,4-Dioxane /-CH2-CH2-O-CH2-CH2-O-\ 101 °C 2.3 1.033 g/ml Tetrahydrofuran (THF) /-CH2-CH2-O-CH2-CH2-\ 66 °C 7.5 0.886 g/ml Acetone CH3-C(=O)-CH3 56 °C 21 0.786 g/ml Acetonitrile (MeCN) CH3-C≡N 82 °C 37 0.786 g/ml Dimethylformamide (DMF) H-C(=O)N(CH3)2 153 °C 38 0.944 g/ml Dimethyl sulfoxide (DMSO) CH3-S(=O)-CH3 189 °C 47 1.092 g/ml Polar Protic Solvents Acetic acid CH3-C(=O)OH 118 °C 6.2 1.049 g/ml n-Butanol CH3-CH2-CH2-CH2-OH 118 °C 18 0.810 g/ml Isopropanol CH3-CH(-OH)-CH3 82 °C 18 0.785 g/ml n-Propanol CH3-CH2-CH2-OH 97 °C 20 0.803 g/ml Ethanol CH3-CH2-OH 79 °C 24 0.789 g/ml Methanol CH3-OH 65 °C 33 0.791 g/ml Formic acid H-C(=O)OH 100 °C 58 1.21 g/ml Water H-O-H 100 °C 80 1.000 g/ml See also Look up solvent in Wiktionary, the free dictionary. Partition coefficient (log P) is a measure of differential solubility of a compound in two solvents Solvent systems exist outside the realm of ordinary organic solvents: Supercritical fluids, ionic liquids and deep eutectic solvents. Water pollution External links Table Properties of common organic solvents Table and text O-Chem Lecture Tables Properties and toxicities of organic solvents Miscibility Table Phenomex Solvent Miscibility Table (includes Polarity Index) Miscibility Table GLS Solvent Miscibility Table (includes Dielectric Constant) Search Term: "Solvent" Categories: Soil contamination | Solvents | Solutions | Chemical compounds

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