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{{short description|Substance dissolving a solute resulting in a solution}} {{Other uses}} {{Use dmy dates|date=January 2020}} [[File:Solvent.png|thumb|A solvent dissolves a solute, resulting in a solution]] [[File:Ethyl-acetate-3D-balls.png|thumb|Ethyl acetate, a nail polish solvent.<ref>{{cite web| url = https://health.howstuffworks.com/skin-care/nail-care/tips/non-acetone-nail-polish-remover.htm| title = What's the Difference Between Acetone and Non-acetone Nail Polish Remover?| date = 3 November 2009}}</ref>]] A '''solvent''' (from the [[Latin language|Latin]] ''[[wikt:solvo#Latin|solvō]]'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a [[Solution (chemistry)|solution]]. A solvent is usually a liquid but can also be a solid, a gas, or a [[supercritical fluid]]. Water is a solvent for [[Chemical polarity#Polarity of molecules|polar molecules]], and the most common solvent used by living things; all the ions and proteins in a [[Cell (biology)|cell]] are dissolved in water within the cell. Major uses of solvents are in paints, paint removers, inks, and dry cleaning.<ref>{{Ullmann |doi=10.1002/14356007.a24_437 |title=Solvents|year=2000 |last1=Stoye |first1=Dieter |isbn=3527306730}}</ref> Specific uses for [[Organic compound|organic]] solvents are in [[dry cleaning]] (e.g. [[tetrachloroethylene]]); as [[paint thinner]]s ([[toluene]], [[turpentine]]); as nail polish removers and solvents of glue ([[acetone]], [[methyl acetate]], [[ethyl acetate]]); in spot removers ([[hexane]], petrol ether); in detergents ([[D-limonene|citrus terpenes]]); and in [[perfume]]s ([[ethanol]]). Solvents find various applications in chemical,<ref>{{Cite journal |last=Suarez |first=Adiran Garaizar |last2=Göller |first2=Andreas H. |last3=Beck |first3=Michael E. |last4=Gheta |first4=Sadra Kashef Ol |last5=Meier |first5=Katharina |date=2024-10-29 |title=Comparative assessment of physics-based in silico methods to calculate relative solubilities |url=https://link.springer.com/article/10.1007/s10822-024-00576-y |journal=Journal of Computer-Aided Molecular Design |language=en |volume=38 |issue=1 |pages=36 |doi=10.1007/s10822-024-00576-y |issn=1573-4951}}</ref> [[pharmaceutical]],<ref>{{Cite journal |last=Higginbotham |first=T. |last2=Meier |first2=K. |last3=Ramírez |first3=J. |last4=Garaizar |first4=A. |date=2025-02-03 |title=Predicting Drug-Polymer Compatibility in Amorphous Solid Dispersions by MD Simulation: On the Trap of Solvation Free Energies |url=https://pubs.acs.org/doi/10.1021/acs.molpharmaceut.4c00810 |journal=Molecular Pharmaceutics |volume=22 |issue=2 |pages=760–770 |doi=10.1021/acs.molpharmaceut.4c00810 |issn=1543-8384}}</ref> oil, and gas industries, including in [[Chemical synthesis|chemical syntheses]] and purification processes Some [[petrochemical]] solvents are highly toxic and emit [[Volatile organic compound|volatile organic compounds]]. Biobased solvents are usually more expensive, but ideally less toxic and [[Biodegradation|biodegradable]]. Biogenic raw materials usable for solvent production are for example [[Lignocellulosic biomass|lignocellulose]], [[starch]] and [[sucrose]], but also waste and byproducts from other industries (such as [[Terpene|terpenes]], [[Vegetable oil|vegetable oils]] and [[Animal fat|animal fats]]).<ref>{{Cite web |title=Biobased Solvents Market Report: Market Analysis and Forecasts |url=https://ceresana.com/en/produkt/biobased-solvents-market-report-world |access-date=2025-02-12 |website=Ceresana Market Research |language=en-US}}</ref> ==Solutions and solvation== When one substance is [[Dissolution (chemistry)|dissolved]] into another, a [[Solution (chemistry)|solution]] is formed.<ref>{{cite book | last1 = Tinoco | first1 = Ignacio | last2 = Sauer | first2 = Kenneth | last3 = Wang | first3 = James C. | name-list-style = vanc | date = 2002 | title = Physical Chemistry | publisher = Prentice Hall | page = [https://archive.org/details/solutionsmanualp0000unse/page/134 134] | isbn = 978-0-13-026607-1 | url = https://archive.org/details/solutionsmanualp0000unse/page/134 }}</ref> This is opposed to the situation when the compounds are [[insoluble]] like sand in water. In a solution, all of the ingredients are uniformly distributed at a molecular level and no residue remains. A solvent-solute mixture consists of a single [[Phase (matter)|phase]] with all solute molecules occurring as ''solvates'' (solvent-solute [[Coordination complex|complexes]]), as opposed to separate continuous phases as in suspensions, emulsions and other types of non-solution mixtures. The ability of one compound to be dissolved in another is known as solubility; if this occurs in all proportions, it is called [[miscibility|miscible]]. In addition to mixing, the substances in a solution interact with each other at the molecular level. When something is dissolved, molecules of the solvent arrange around [[molecule]]s of the solute. [[Heat transfer]] is involved and [[entropy]] is increased making the solution more [[thermodynamically stable]] than the solute and solvent separately. This arrangement is mediated by the respective chemical properties of the solvent and solute, such as [[hydrogen bonding]], [[Bond dipole moment|dipole moment]] and [[polarizability]].<ref>Lowery and Richardson, pp. 181–183</ref> Solvation does not cause a chemical reaction or chemical configuration changes in the solute. However, solvation resembles a [[coordination complex]] formation reaction, often with considerable energetics (heat of solvation and entropy of solvation) and is thus far from a neutral process. When one substance dissolves into another, a solution is formed. A solution is a homogeneous mixture consisting of a solute dissolved into a solvent. The solute is the substance that is being dissolved, while the solvent is the dissolving medium. Solutions can be formed with many different types and forms of solutes and solvents. ==Solvent classifications== Solvents can be broadly classified into two categories: ''polar'' and ''non-polar''. A special case is elemental [[mercury (element)|mercury]], whose solutions are known as [[Amalgam (chemistry)|amalgams]]; also, other [[liquid metal|metal solutions]] exist which are liquid at room temperature. Generally, the [[dielectric constant]] of the solvent provides a rough measure of a solvent's polarity. The strong polarity of water is indicated by its high dielectric constant of 88 (at 0 °C).<ref name="NIST water">{{cite journal| vauthors = Malmberg CG, Maryott AA |title=Dielectric Constant of Water from 0° to 100 °C|journal=Journal of Research of the National Bureau of Standards|date=January 1956|volume=56|issue=1|page=1|doi=10.6028/jres.056.001|doi-access=free}}</ref> Solvents with a dielectric constant of less than 15 are generally considered to be nonpolar.<ref name=p177>Lowery and Richardson, p. 177.</ref> The dielectric constant measures the solvent's tendency to partly cancel the field strength of the electric field of a [[ion|charged particle]] immersed in it. This reduction is then compared to the [[field strength]] of the charged particle in a vacuum.<ref name=p177/> Heuristically, the dielectric constant of a solvent can be thought of as its ability to reduce the solute's effective [[chemical polarity|internal charge]]. Generally, the dielectric constant of a solvent is an acceptable predictor of the solvent's ability to dissolve common [[ionic compound]]s, such as salts. ===Other polarity scales=== Dielectric constants are not the only measure of polarity. Because solvents are used by chemists to carry out chemical reactions or observe chemical and biological phenomena, more specific measures of polarity are required. Most of these measures are sensitive to chemical structure. The ''[[Grunwald–Winstein equation|Grunwald–Winstein]] m'''Y''' scale'' measures polarity in terms of solvent influence on buildup of positive charge of a solute during a chemical reaction. ''[[Edward Kosower|Kosower]]'s '''Z''' scale'' measures polarity in terms of the influence of the solvent on [[Ultraviolet|UV]]-absorption maxima of a salt, usually [[pyridinium]] [[iodide]] or the pyridinium [[zwitterion]].<ref>Kosower, E.M. (1969) "An introduction to Physical Organic Chemistry" Wiley: New York, p. 293</ref> ''Donor number and donor acceptor scale'' measures polarity in terms of how a solvent interacts with specific substances, like a strong [[Lewis acid]] or a strong Lewis base.<ref>{{Cite journal| vauthors = Gutmann V |journal = Coord. Chem. Rev.|year = 1976|volume = 18|issue = 2|page = 225|doi = 10.1016/S0010-8545(00)82045-7|title = Solvent effects on the reactivities of organometallic compounds}}</ref> The ''[[Hildebrand parameter]]'' is the square root of '''cohesive energy density'''. It can be used with nonpolar compounds, but cannot accommodate complex chemistry. Reichardt's dye, a [[solvatochromic]] dye that changes color in response to polarity, gives a scale of ''E<sub>T</sub>''(30) values. ''E<sub>T</sub>'' is the transition energy between the ground state and the lowest excited state in kcal/mol, and (30) identifies the dye. Another, roughly correlated scale (''E<sub>T</sub>''(33)) can be defined with [[Nile red]]. Gregory's solvent ϸ parameter is a quantum chemically derived charge density parameter.<ref>{{Cite journal |last=Gregory |first=Kasimir P. |last2=Wanless |first2=Erica J. |last3=Webber |first3=Grant B. |last4=Craig |first4=Vincent S. J. |last5=Page |first5=Alister J. |year=2024 |title=A first-principles alternative to empirical solvent parameters |journal=Phys. Chem. Chem. Phys. |volume=26 |issue=31 |pages=20750–20759 |bibcode=2024PCCP...2620750G |doi=10.1039/D4CP01975J |pmid=38988220}}</ref> This parameter seems to reproduce many of the experimental solvent parameters (especially the donor and acceptor numbers) using this charge decomposition analysis approach, with an electrostatic basis. The ϸ parameter was originally developed to quantify and explain the [[Hofmeister series]] by quantifying polyatomic ions and the monatomic ions in a united manner. {{anchor|LikeDissolvesLike}}The polarity, dipole moment, polarizability and [[hydrogen bonding]] of a solvent determines what type of [[Chemical compound|compounds]] it is able to dissolve and with what other solvents or liquid compounds it is [[miscible]]. Generally, polar solvents dissolve polar compounds best and non-polar solvents dissolve non-polar compounds best; hence "''like dissolves like''". Strongly polar compounds like [[sugar]]s (e.g. [[sucrose]]) or ionic compounds, like [[Inorganic chemistry|inorganic]] [[Salt (chemistry)|salt]]s (e.g. [[table salt]]) dissolve only in very polar solvents like water, while strongly non-polar compounds like [[oil]]s or [[wax]]es dissolve only in very non-polar organic solvents like [[hexane]]. Similarly, water and [[hexane]] (or [[vinegar]] and vegetable oil) are not [[miscible]] with each other and will quickly separate into two layers even after being shaken well. Polarity can be separated to different contributions. For example, the '''Kamlet-Taft parameters''' are dipolarity/polarizability (''π*''), hydrogen-bonding acidity (''α'') and hydrogen-bonding basicity (''β''). These can be calculated from the wavelength shifts of 3–6 different solvatochromic dyes in the solvent, usually including [[Reichardt's dye]], [[nitroaniline]] and [[diethylnitroaniline]]. Another option, [[Hansen solubility parameter]]s, separates the cohesive energy density into dispersion, polar, and hydrogen bonding contributions. ===Polar protic and polar aprotic=== Solvents with a dielectric constant (more accurately, [[relative static permittivity]]) greater than 15 (i.e. polar or polarizable) can be further divided into [[protic]] and aprotic. Protic solvents, such as [[water]], solvate [[anion]]s (negatively charged solutes) strongly via [[hydrogen bonding]]. [[Polar aprotic solvent]]s, such as [[acetone]] or [[dichloromethane]], tend to have large [[Molecular dipole moment|dipole moments]] (separation of partial positive and partial negative charges within the same molecule) and solvate positively charged species via their negative dipole.<ref>Lowery and Richardson, p. 183.</ref> In [[chemical reaction]]s the use of polar protic solvents favors the [[SN1 reaction|S<sub>N</sub>1]] [[reaction mechanism]], while polar aprotic solvents favor the [[SN2 reaction|S<sub>N</sub>2]] reaction mechanism. These polar solvents are capable of forming hydrogen bonds with water to dissolve in water whereas non-polar solvents are not capable of strong hydrogen bonds. ==Physical properties== ===Properties table of common solvents=== The solvents are grouped into [[nonpolar]], polar [[aprotic]], and polar [[protic]] solvents, with each group ordered by increasing polarity. The [[Property|properties]] of solvents which exceed those of water are bolded. <!-- Here is a table of data; skip past it to edit the text. --> {| cellpadding="5" cellspacing="0" style="margin:auto; text-align:center;" class="wikitable" |- ! Solvent ! [[Chemical formula]] ! [[Boiling point]]<ref name=boil>[http://www.xydatasource.com/xy-showdatasetpage.php?datasetcode=9724855&dsid=1138&searchtext=solvent Solvent Properties – Boiling Point] {{webarchive|url=https://web.archive.org/web/20110614130546/http://www.xydatasource.com/xy-showdatasetpage.php?datasetcode=9724855&dsid=1138&searchtext=solvent |date=14 June 2011 }}. Xydatasource.com. Retrieved on 26 January 2013.</ref><br />(°C) ! [[Dielectric constant]]<ref>[http://macro.lsu.edu/HowTo/solvents/Dielectric%20Constant%20.htm Dielectric Constant] {{webarchive|url=https://web.archive.org/web/20100704013154/http://macro.lsu.edu/HowTo/solvents/Dielectric%20Constant%20.htm |date=4 July 2010 }}. Macro.lsu.edu. Retrieved on 26 January 2013.</ref> ! [[Density]]<br />(g/mL) ! [[Molecular dipole moment|Dipole moment]]<br />([[Debye|D]]) <!-- ### Non-polar solvents ### --> |- style="background:#ddd;height: 50px;vertical-align:top" ! colspan="6"| ==== Nonpolar [[hydrocarbon]] solvents ==== |- style="background:#ddd;" | [[Pentane]] |[[File:Pentane-2D-Skeletal.svg|frameless|200px]] CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | 36.1 | 1.84 | 0.626 | 0.00 |- style="background:#ddd;" | [[Hexane]] |[[File:Hexane-2D-skeletal.svg|frameless|241px]] CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | 69 | 1.88 | 0.655 | 0.00 |- style="background:#ddd;" | [[Benzene]] | [[File:Benzene 200.svg|90px]]<br />C<sub>6</sub>H<sub>6</sub> | 80.1 | 2.3 | 0.879 | 0.00 |- style="background:#ddd;" | [[Heptane]] | [[File:Heptane-2D-Skeletal.svg|frameless|286px]] H<sub>3</sub>C(CH<sub>2</sub>)<sub>5</sub>CH<sub>3</sub> | 98.38 | 1.92 | 0.680 | 0.0 |- style="background:#ddd;" | [[Toluene]] | [[File:Toluol.svg|55px]] C<sub>6</sub>H<sub>5</sub>-CH<sub>3</sub> | '''111''' | 2.38 | 0.867 | 0.36 |- style="background:#ddd;" ! colspan="6"| ==== Nonpolar [[ether]] solvents ==== |- style="background:#ddd;" | [[1,4-Dioxane]] | [[File:1-4-Dioxane.svg|100px]]<br />C<sub>4</sub>H<sub>8</sub>O<sub>2</sub> | '''101.1''' | 2.3 | '''1.033''' | 0.45 |- style="background:#ddd;" | [[Diethyl ether]] |[[File:Diethyl ether chemical structure.svg|frameless|203x203px]] CH<sub>3</sub>CH<sub>2</sub>-O-CH<sub>2</sub>CH<sub>3</sub> | 34.6 | 4.3 | 0.713 | 1.15 |- style="background:#ddd;" | [[Tetrahydrofuran]] (THF) | [[File:Tetrahydrofuran.svg|100px]]<br />C<sub>4</sub>H<sub>8</sub>O | 66 | 7.5 | 0.886 | 1.75 |- style="background:#fcf;" ! colspan="6"| ==== Nonpolar [[chlorocarbon]] solvents ==== |- style="background:#ddd;" | [[Chloroform]] |[[File:Chloroform displayed.svg|frameless|145x145px]] CHCl<sub>3</sub> | 61.2 | 4.81 |'''1.498''' | 1.04<!-- ### Polar aprotic solvents ### --> |- style="background:#fcf;height: 50px;vertical-align:top" ! colspan="6"|Polar [[Aprotic solvent|aprotic]] solvents |- style="background:#fcf;" | [[Dichloromethane]] (DCM) |[[File:Dichloromethane molecular structure.svg|frameless|138x138px]] CH<sub>2</sub>Cl<sub>2</sub> | 39.6 | 9.1 | '''1.3266''' | 1.60 |- style="background:#fcf;" | [[Ethyl acetate]] | [[File:Essigsäureethylester.svg]]<br />CH<sub>3</sub>-C(=O)-O-CH<sub>2</sub>-CH<sub>3</sub> | 77.1 | 6.02 | 0.894 | 1.78 |- style="background:#fcf;" | [[Acetone]] | [[File:Acetone-2D-skeletal.svg|90px]]<br />CH<sub>3</sub>-C(=O)-CH<sub>3</sub> | 56.1 | 21 | 0.786 | '''2.88''' |- style="background:#fcf;" | [[Dimethylformamide]] (DMF) | [[File:Dimethylformamide.svg|100px]]<br />H-C(=O)N(CH<sub>3</sub>)<sub>2</sub> | '''153''' | 38 | 0.944 | '''3.82''' |- style="background:#fcf;" | [[Acetonitrile]] (MeCN) |[[File:Acetonitrile-2D-skeletal.svg|frameless|164x164px]] CH<sub>3</sub>-C≡N | 82 | 37.5 | 0.786 | '''3.92''' |- style="background:#fcf;" | [[Dimethyl sulfoxide]] (DMSO) | [[File:Dimethylsulfoxid.svg]]<br />CH<sub>3</sub>-S(=O)-CH<sub>3</sub> | '''189''' | 46.7 | '''1.092''' | '''3.96''' |- style="background:#fcf;" | [[Nitromethane]] |[[File:Nitromethaan.svg|163x163px]] CH<sub>3</sub>-NO<sub>2</sub> | '''100–103''' | 35.87 | '''1.1371''' | '''3.56''' |- style="background:#fcf;" | [[Propylene carbonate]] |[[File:Propylene Carbonate V.1.svg|frameless|233x233px]] C<sub>4</sub>H<sub>6</sub>O<sub>3</sub> | '''240''' | 64.0 | '''1.205''' | '''4.9''' <!-- ### Polar protic solvents ### --> |- style="background:#fcc;height: 50px;vertical-align:top" ! colspan="6"| ==== Polar [[protic]] solvents ==== |- style="background:#fcc;" |[[Ammonia]] |[[File:Ammonia-2D.svg|frameless|152x152px]] NH<sub>3</sub> | -33.3 |17 |0.674 (at -33.3 °C) |1.42 |- style="background:#fcc;" | [[Formic acid]] | [[File:Formic acid.svg|120x120px]]<br />H-C(=O)OH | '''100.8''' | 58 | '''1.21''' | 1.41 |- style="background:#fcc;" | [[n-Butanol|''n''-Butanol]] |[[File:Butan-1-ol Skelett.svg|frameless|215x215px]] CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH | '''117.7''' | 18 | 0.810 | 1.63 |- style="background:#fcc;" | [[Isopropyl alcohol]] (IPA) | [[File:2-Propanol2.svg|155x155px]]<br />CH<sub>3</sub>-CH(-OH)-CH<sub>3</sub> | 82.6 | 18 | 0.785 | 1.66 |- style="background:#fcc;" | [[1-Propanol|''n''-Propanol]] |[[File:Propan-1-ol.svg|frameless|191x191px]] CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH | 97 | 20 | 0.803 | 1.68 |- style="background:#fcc;" | [[Ethanol]] |[[File:Ethanol-2D-skeletal.svg|frameless|125x125px]] CH<sub>3</sub>CH<sub>2</sub>OH | 78.2 | 24.55 | 0.789 | 1.69 |- style="background:#fcc;" | [[Methanol]] |[[File:Methanol-2D.svg|frameless|128x128px]] CH<sub>3</sub>OH | 64.7 | 33 | 0.791 | 1.70 |- style="background:#fcc;" | [[Acetic acid]] |[[File:Acetic-acid-2D-skeletal.svg|alt=|frameless|128x128px]]<br />CH<sub>3</sub>-C(=O)OH | '''118''' | 6.2 | '''1.049''' | 1.74 |- style="background:#fcc;" | [[Water (molecule)|Water]] | [[File:Wasser Strukturformel V1.svg|98x98px]]<br />H-O-H | 100 | 80 | 1.000 | 1.85 |} The [[American Chemical Society|ACS Green Chemistry Institute]] maintains a tool for the selection of solvents based on a [[principal component analysis]] of solvent properties.<ref>{{cite journal |doi=10.1021/acs.oprd.6b00015 |title=Toward a More Holistic Framework for Solvent Selection |year=2016 |last1=Diorazio |first1=Louis J. |last2=Hose |first2=David R. J. |last3=Adlington |first3=Neil K. |journal=Organic Process Research & Development |volume=20 |issue=4 |pages=760–773 |doi-access=free }}</ref> ===Hansen solubility parameter values=== The [[Hansen solubility parameter]] (HSP) values<ref name=hansen/><ref name="hansen2">{{Cite book |last=Hansen |first=Charles M. |url=https://books.google.com/books?id=gprF31cvT2oC |title=Hansen Solubility Parameters: A User's Handbook, Second Edition |date=2007-06-15 |publisher=CRC Press |isbn=978-1-4200-0683-4 |language=en}}</ref><ref>{{Cite journal |last=Bergin |first=Shane D. |last2=Sun |first2=Zhenyu |last3=Rickard |first3=David |last4=Streich |first4=Philip V. |last5=Hamilton |first5=James P. |last6=Coleman |first6=Jonathan N. |date=2009-08-25 |title=Multicomponent Solubility Parameters for Single-Walled Carbon Nanotube−Solvent Mixtures |url=https://pubs.acs.org/doi/abs/10.1021/nn900493u |journal=ACS Nano |volume=3 |issue=8 |pages=2340–2350 |doi=10.1021/nn900493u |issn=1936-0851|url-access=subscription }}</ref> are based on [[Van der Waals forces|dispersion bonds]] (δD), [[polar bonds]] (δP) and [[hydrogen bonds]] (δH). These contain information about the inter-molecular interactions with other solvents and also with polymers, pigments, [[nanoparticle]]s, etc. This allows for rational formulations knowing, for example, that there is a good HSP match between a solvent and a polymer. Rational substitutions can also be made for "good" solvents (effective at dissolving the solute) that are "bad" (expensive or hazardous to health or the environment). The following table shows that the intuitions from "non-polar", "polar aprotic" and "polar protic" are put numerically – the "polar" molecules have higher levels of δP and the protic solvents have higher levels of δH. Because numerical values are used, comparisons can be made rationally by comparing numbers. For example, acetonitrile is much more polar than acetone but exhibits slightly less hydrogen bonding. <!-- Here is a table of data; skip past it to edit the text. --> {| class="wikitable sortable" style="margin:auto; text-align:center;" |- ! Solvent ! [[Chemical formula]] ! δD Dispersion ! δP Polar ! δH Hydrogen bonding <!-- ### Non-polar solvents ### --> |- style="background:#ddd;height: 50px;vertical-align:top" ! colspan="5"| ==== Non-polar solvents ==== |- style="background:#ddd;" | [[n-Pentane]] | CH<sub>3</sub>-(CH<sub>2</sub>)<sub>3</sub>-CH<sub>3</sub> | 14.5 | 0.0 | 0.0 |- style="background:#ddd;" | [[n-Hexane]] | CH<sub>3</sub>-(CH<sub>2</sub>)<sub>4</sub>-CH<sub>3</sub> | 14.9 | 0.0 | 0.0 |- style="background:#ddd;" | [[n-Heptane]] | CH<sub>3</sub>-(CH<sub>2</sub>)<sub>5</sub>-CH<sub>3</sub> | 15.3 | 0.0 | 0.0 |- style="background:#ddd;" | [[Cyclohexane]] | <u>/-(CH<sub>2</sub>)<sub>6</sub>-\</u> | 16.8 | 0.0 | 0.2 |- style="background:#ddd;" | [[Benzene]] | C<sub>6</sub>H<sub>6</sub> | 18.4 | 0.0 | 2.0 |- style="background:#ddd;" | [[Toluene]] | C<sub>6</sub>H<sub>5</sub>-CH<sub>3</sub> | 18.0 | 1.4 | 2.0 |- style="background:#ddd;" | [[Diethyl ether]] | C<sub>2</sub>H<sub>5</sub>-O-C<sub>2</sub>H<sub>5</sub> | 14.5 | 2.9 | 4.6 |- style="background:#ddd;" | [[Chloroform]] | CHCl<sub>3</sub> | 17.8 | 3.1 | 5.7 |- style="background:#ddd;" | [[1,4-Dioxane]] | <u>/-(CH<sub>2</sub>)<sub>2</sub>O(CH<sub>2</sub>)<sub>2</sub>O-\</u> | 17.5 | 1.8 | 9.0 |- style="background:#fcf;height: 50px;vertical-align:top"<!-- ### Polar aprotic solvents ### --> ! colspan="5"| ==== Polar aprotic solvents ==== |- style="background:#fcf;" | [[Ethyl acetate]] | CH<sub>3</sub>-C(=O)-O-C<sub>2</sub>H<sub>5</sub> | 15.8 | 5.3 | 7.2 |- style="background:#fcf;" | [[Tetrahydrofuran]] | <u>/-(CH<sub>2</sub>)<sub>4</sub>-O-\</u> | 16.8 | 5.7 | 8.0 |- style="background:#fcf;" | [[Dichloromethane]] | CH<sub>2</sub>Cl<sub>2</sub> | 17.0 | 7.3 | 7.1 |- style="background:#fcf;" | [[Acetone]] | CH<sub>3</sub>-C(=O)-CH<sub>3</sub> | 15.5 | 10.4 | 7.0 |- style="background:#fcf;" | [[Acetonitrile]] | CH<sub>3</sub>-C≡N | 15.3 | 18.0 | 6.1 |- style="background:#fcf;" | [[Dimethylformamide]] | H-C(=O)-N(CH<sub>3</sub>)<sub>2</sub> | 17.4 | 13.7 | 11.3 |- style="background:#fcf;" |[[Dimethylacetamide]] |CH<sub>3</sub>-C(=O)-N(CH<sub>3</sub>)<sub>2</sub> |16.8 |11.5 |10.2 |- style="background:#fcf;" |[[Dimethylimidazolidinone]] |C<sub>5</sub>H<sub>10</sub>N<sub>2</sub>O |18.0 |10.5 |9.7 |- style="background:#fcf;" |[[DMPU|Dimethylpropyleneurea]] |C<sub>6</sub>H<sub>12</sub>N<sub>2</sub>O |17.8 |9.5 |9.3 |- style="background:#fcf;" |[[N-Methylpyrrolidone]] |<u>/-(CH<sub>2</sub>)<sub>3</sub>-N(CH<sub>3</sub>)-C(=O)-\</u> |18.0 |12.3 |7.2 |- style="background:#fcf;" |[[Propylene carbonate]] |C<sub>4</sub>H<sub>6</sub>O<sub>3</sub> |20.0 |18.0 |4.1 |- style="background:#fcf;" |[[Pyridine]] |C<sub>5</sub>H<sub>5</sub>N |19.0 |8.8 |5.9 |- style="background:#fcf;" |[[Sulfolane]] |<u>/-(CH<sub>2</sub>)<sub>4</sub>-S(=O)<sub>2</sub>-\</u> |19.2 |16.2 |9.4 |- style="background:#fcf;" | [[Dimethyl sulfoxide]] | CH<sub>3</sub>-S(=O)-CH<sub>3</sub> | 18.4 | 16.4 | 10.2 |- style="background:#fcc;height: 50px;vertical-align:top" ! colspan="5"| ==== Polar protic solvents ==== |- style="background:#fcc;" | [[Acetic acid]] | CH<sub>3</sub>-C(=O)-OH | 14.5 | 8.0 | 13.5 |- style="background:#fcc;" | [[n-Butanol|''n''-Butanol]] | CH<sub>3</sub>-(CH<sub>2</sub>)<sub>3</sub>-OH | 16.0 | 5.7 | 15.8 |- style="background:#fcc;" | [[Isopropanol]] | (CH<sub>3</sub>)<sub>2</sub>-CH-OH | 15.8 | 6.1 | 16.4 |- style="background:#fcc;" | [[1-Propanol|''n''-Propanol]] | CH<sub>3</sub>-(CH<sub>2</sub>)<sub>2</sub>-OH | 16.0 | 6.8 | 17.4 |- style="background:#fcc;" | [[Ethanol]] | C<sub>2</sub>H<sub>5</sub>-OH | 15.8 | 8.8 | 19.4 |- style="background:#fcc;" | [[Methanol]] | CH<sub>3</sub>-OH | 14.7 | 12.3 | 22.3 |- style="background:#fcc;" |[[Ethylene glycol]] |HO-(CH<sub>2</sub>)<sub>2</sub>-OH |17.0 |11.0 |26.0 |- style="background:#fcc;" |[[Glycerol]] |HO-CH<sub>2</sub>-CH(OH)-CH<sub>2</sub>-OH |17.4 |12.1 |29.3 |- style="background:#fcc;" | [[Formic acid]] | H-C(=O)-OH | 14.6 | 10.0 | 14.0 |- style="background:#fcc;" | [[Water (molecule)|Water]] | H-O-H | 15.5 | 16.0 | 42.3 |- |} If, for environmental or other reasons, a solvent or solvent blend is required to replace another of equivalent solvency, the substitution can be made on the basis of the Hansen solubility parameters of each. The values for mixtures are taken as the [[weighted average]]s of the values for the neat solvents. This can be calculated by [[trial-and-error]], a spreadsheet of values, or HSP software.<ref name=hansen>{{cite book | vauthors = Abbott S, Hansen CM | title = Hansen solubility parameters in practice. | publisher = Hansen-Solubility | date = 2008 | isbn = 978-0-9551220-2-6 | url = https://books.google.com/books?id=efMbTvlfc8wC }}</ref><ref name="hansen2" /> A 1:1 mixture of [[toluene]] and [[1,4 dioxane]] has δD, δP and δH values of 17.8, 1.6 and 5.5, comparable to those of [[chloroform]] at 17.8, 3.1 and 5.7 respectively. Because of the health hazards associated with toluene itself, other mixtures of solvents may be found using a full HSP dataset. ===Boiling point=== <div style="float:right; margin:5px;"> {| class="wikitable" style="margin:1em auto; text-align:center;" |- ! Solvent ! Boiling point (°C)<ref name=boil/> |- | ethylene dichloride | 83.48 |- | pyridine | 115.25 |- | methyl isobutyl ketone | 116.5 |- | methylene chloride | 39.75 |- | isooctane | 99.24 |- | carbon disulfide | 46.3 |- | carbon tetrachloride | 76.75 |- | ''o''-xylene | 144.42 |}</div> The boiling point is an important property because it determines the speed of evaporation. Small amounts of low-boiling-point solvents like [[diethyl ether]], [[dichloromethane]], or acetone will evaporate in seconds at room temperature, while high-boiling-point solvents like water or [[dimethyl sulfoxide]] need higher temperatures, an air flow, or the application of [[vacuum]] for fast evaporation. *Low boilers: boiling point below 100 °C (boiling point of water) *Medium boilers: between 100 °C and 150 °C *High boilers: above 150 °C ===Density=== Most organic solvents have a lower [[density]] than water, which means they are lighter than and will form a layer on top of water. Important exceptions are most of the [[halogen]]ated solvents like [[dichloromethane]] or [[chloroform]] will sink to the bottom of a container, leaving water as the top layer. This is crucial to remember when [[partition coefficient|partitioning]] compounds between solvents and water in a [[separatory funnel]] during chemical syntheses. Often, [[specific gravity]] is cited in place of density. Specific gravity is defined as the density of the solvent divided by the density of water at the same temperature. As such, specific gravity is a unitless value. It readily communicates whether a water-insoluble solvent will float (SG < 1.0) or sink (SG > 1.0) when mixed with water. {| class="wikitable sortable mw-collapsible mw-collapsed" style="margin:1em auto; text-align:center;" ! Solvent ! [[Specific gravity]]<ref>[http://www.xydatasource.com/xy-showdatasetpage.php?datasetcode=831841&dsid=97&searchtext=solvent Selected solvent properties – Specific Gravity] {{webarchive|url=https://web.archive.org/web/20110614130527/http://www.xydatasource.com/xy-showdatasetpage.php?datasetcode=831841&dsid=97&searchtext=solvent |date=14 June 2011 }}. Xydatasource.com. Retrieved on 26 January 2013.</ref> |- | Pentane | 0.626 |- | Petroleum ether | 0.656 |- | Hexane | 0.659 |- | Heptane | 0.684 |- | Diethyl amine | 0.707 |- | Diethyl ether | 0.713 |- | Triethyl amine | 0.728 |- | ''tert''-Butyl methyl ether | 0.741 |- | Cyclohexane | 0.779 |- | ''tert''-Butyl alcohol | 0.781 |- | Isopropanol | 0.785 |- | Acetonitrile | 0.786 |- | Ethanol | 0.789 |- | Acetone | 0.790 |- | Methanol | 0.791 |- | Methyl isobutyl ketone | 0.798 |- | Isobutyl alcohol | 0.802 |- | 1-Propanol | 0.803 |- | Methyl ethyl ketone | 0.805 |- | 2-Butanol | 0.808 |- | Isoamyl alcohol | 0.809 |- | 1-Butanol | 0.810 |- | Diethyl ketone | 0.814 |- | 1-Octanol | 0.826 |- | ''p''-Xylene | 0.861 |- | ''m''-Xylene | 0.864 |- | Toluene | 0.867 |- | Dimethoxyethane | 0.868 |- | Benzene | 0.879 |- | Butyl acetate | 0.882 |- | 1-Chlorobutane | 0.886 |- | Tetrahydrofuran | 0.889 |- | Ethyl acetate | 0.895 |- | ''o''-Xylene | 0.897 |- | Hexamethylphosphorus triamide | 0.898 |- | 2-Ethoxyethyl ether | 0.909 |- | ''N'',''N''-Dimethylacetamide | 0.937 |- | [[Diglyme|Diethylene glycol dimethyl ether]] | 0.943 |- | ''N'',''N''-Dimethylformamide | 0.944 |- | 2-Methoxyethanol | 0.965 |- | Pyridine | 0.982 |- | Propanoic acid | 0.993 |- | Water | 1.000 |- | 2-Methoxyethyl acetate | 1.009 |- | Benzonitrile | 1.01 |- | 1-Methyl-2-pyrrolidinone | 1.028 |-. | Hexamethylphosphoramide | 1.03 |- | 1,4-Dioxane | 1.033 |- | Acetic acid | 1.049 |- | Acetic anhydride | 1.08 |- | Dimethyl sulfoxide | 1.092 |- | Chlorobenzene | 1.1066 |- | Deuterium oxide | 1.107 |- | Ethylene glycol | 1.115 |- | Diethylene glycol | 1.118 |- | Propylene carbonate | 1.21 |- | Formic acid | 1.22 |- | 1,2-Dichloroethane | 1.245 |- | Glycerin | 1.261 |- | Carbon disulfide | 1.263 |- | 1,2-Dichlorobenzene | 1.306 |- | Methylene chloride | 1.325 |- | Nitromethane | 1.382 |- | 2,2,2-Trifluoroethanol | 1.393 |- | Chloroform | 1.498 |- | 1,1,2-Trichlorotrifluoroethane | 1.575 |- | Carbon tetrachloride | 1.594 |- | Tetrachloroethylene | 1.623 |} == Multicomponent solvents == {{citations needed|section|date=January 2022}} Multicomponent solvents appeared after World War II in the [[USSR]], and continue to be used and produced in the post-Soviet states. These solvents may have one or more applications, but they are not universal preparations. === Solvents === {| class="wikitable" |- ! Name !! Composition |- | Solvent 645 || [[toluene]] 50%, [[butyl acetate]] 18%, [[ethyl acetate]] 12%, [[butanol]] 10%, [[ethanol]] 10%. |- | Solvent 646 || toluene 50%, ethanol 15%, butanol 10%, butyl- or [[amyl acetate]] 10%, [[ethyl cellosolve]] 8%, [[acetone]] 7%<ref>{{cite web| url = https://www.dcpt.ru/rastvoritel-646/#tab3| title = dcpt.ru Solvent 646 Characteristics (ru)}}</ref> |- | Solvent 647 || butyl- or amyl acetate 29.8%, ethyl acetate 21.2%, butanol 7.7%, toluene or [[benzopyrene]] 41.3%<ref>{{cite web| url = https://www.dcpt.ru/rastvoritel-647/#tab3| title = dcpt.ru Solvent 647 Characteristics (ru)}}</ref> |- | Solvent 648 || butyl acetate 50%, ethanol 10%, butanol 20%, toluene 20%<ref>{{cite web| url = https://www.dcpt.ru/rastvoritel-marki-r-648/| title = dcpt.ru Solvent 648 Characteristics (ru)| access-date = 18 January 2018| archive-date = 17 May 2017| archive-url = https://web.archive.org/web/20170517175055/http://www.dcpt.ru/rastvoritel-marki-r-648/| url-status = dead}}</ref> |- | Solvent 649 || ethyl cellosolve 30%, butanol 20%, [[xylene]] 50% |- | Solvent 650 || ethyl cellosolve 20%, butanol 30%, xylene 50%<ref>{{cite web| url = https://www.dcpt.ru/primenenie-r-650-ximicheskogo-rastvoritelya/| title = dcpt.ru Solvent 650 Characteristics (ru)}}</ref> |- | Solvent 651 || [[white spirit]] 90%, butanol 10% |- | Solvent KR-36 || butyl acetate 20%, butanol 80% |- | Solvent R-4 || toluene 62%, acetone 26%, butyl acetate 12%. |- | Solvent R-10 || xylene 85%, acetone 15%. |- | Solvent R-12 || toluene 60%, butyl acetate 30%, xylene 10%. |- | Solvent R-14 || [[cyclohexanone]] 50%, toluene 50%. |- | Solvent R-24 || solvent{{Clarify|reason=It is unclear what is meant by "solvent". If it is a generic term, please specify|date=September 2024}} 50%, xylene 35%, acetone 15%. |- | Solvent R-40 || toluene 50%, ethyl cellosolve 30%, acetone 20%. |- | Solvent R-219 || toluene 34%, cyclohexanone 33%, acetone 33%. |- | Solvent R-3160 || butanol 60%, ethanol 40%. |- | Solvent RCC || xylene 90%, butyl acetate 10%. |- | Solvent RML || ethanol 64%, ethylcellosolve 16%, toluene 10%, butanol 10%. |- | Solvent PML-315 || toluene 25%, xylene 25%, butyl acetate 18%, ethyl cellosolve 17%, butanol 15%. |- | Solvent PC-1 || toluene 60%, butyl acetate 30%, xylene 10%. |- | Solvent PC-2 || white spirit 70%, xylene 30%. |- | Solvent RFG || ethanol 75%, butanol 25%. |- | Solvent RE-1 || xylene 50%, acetone 20%, butanol 15%, ethanol 15%. |- | Solvent RE-2 || petroleum spirits 70%, ethanol 20%, acetone 10%. |- | Solvent RE-3 || petroleum spirits 50%, ethanol 20%, acetone 20%, ethyl cellosolve 10%. |- | Solvent RE-4 || petroleum spirits 50%, acetone 30%, ethanol 20%. |- | Solvent FK-1 (?) || absolute alcohol (99.8%) 95%, ethyl acetate 5% |} === Thinners === {| class="wikitable" |- ! Name !! Composition |- |Thinner RKB-1 || butanol 50%, xylene 50% |- | Thinner RKB-2 || butanol 95%, xylene 5% |- | Thinner RKB-3 || xylene 90%, butanol 10% |- | Thinner M || ethanol 65%, butyl acetate 30%, ethyl acetate 5%. |- | Thinner P-7 || cyclohexanone 50%, ethanol 50%. |- | Thinner R-197 || xylene 60%, butyl acetate 20%, ethyl cellosolve 20%. |- | Thinner of WFD || toluene 50%, butyl acetate (or amyl acetate) 18%, butanol 10%, ethanol 10%, ethyl acetate 9%, acetone 3%. |} ==Safety== ===Fire=== Most organic solvents are [[flammable]] or highly flammable, depending on their [[volatility (chemistry)|volatility]]. Exceptions are some chlorinated solvents like [[dichloromethane]] and [[chloroform]]. Mixtures of solvent vapors and air can [[explosion|explode]]. Solvent vapors are heavier than air; they will sink to the bottom and can travel large distances nearly undiluted. Solvent vapors can also be found 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 disulfide]] have exceptionally low [[autoignition temperature]]s which increase greatly the fire risk associated with these solvents. The autoignition temperature of carbon disulfide is below 100 °C (212 °F), so objects such as [[steam]] pipes, [[light bulb]]s, [[hotplate]]s, and recently extinguished [[bunsen burner]]s are able to ignite its vapors. In addition some solvents, such as methanol, can burn with a very hot flame which can be nearly invisible under some lighting conditions.<ref>{{Cite book|last1=Fanick|first1=E. Robert|last2=Smith|first2=Lawrence R.|last3=Baines|first3=Thomas M. | name-list-style = vanc |date=1 October 1984|chapter=Safety Related Additives for Methanol Fuel|chapter-url=http://papers.sae.org/841378/ |publisher=SAE |location=Warrendale, PA|url-status=live|archive-url=https://web.archive.org/web/20170812062146/http://papers.sae.org/841378/|archive-date=12 August 2017|doi=10.4271/841378|title=SAE Technical Paper Series|volume=1}}</ref><ref>{{Cite journal| vauthors = Anderson JE, Magyarl MW, Siegl WO |date=1 July 1985|title=Concerning the Luminosity of Methanol-Hydrocarbon Diffusion Flames|journal=Combustion Science and Technology|volume=43|issue=3–4|pages=115–125|doi=10.1080/00102208508947000|issn=0010-2202}}</ref> This can delay or prevent the timely recognition of a dangerous fire, until flames spread to other materials. ===Explosive peroxide formation=== [[Ether]]s like [[diethyl ether]] and [[tetrahydrofuran]] (THF) can form highly explosive [[organic peroxide]]s 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.{{clarify|date=March 2017}} The carbon-centered free radical thus formed is able to react with an oxygen molecule to form a peroxide compound. The process of peroxide formation is greatly accelerated by exposure to even low levels of light, but can proceed slowly even in dark conditions. Unless a [[desiccant]] is used which can destroy the peroxides, they will concentrate during [[distillation]], due to their higher [[boiling point]]. When sufficient peroxides have formed, they can form a [[crystalline]], shock-sensitive solid [[precipitate]] at the mouth of a container or bottle. Minor mechanical disturbances, such as scraping the inside of a vessel, the dislodging of a deposit, or merely twisting the cap may provide sufficient energy for the peroxide to [[detonation|detonate]] or explode violently. Peroxide formation is not a significant problem when fresh solvents are used up quickly; they are more of a problem in laboratories which may take years to finish a single bottle. Low-volume users should acquire only small amounts of peroxide-prone solvents, and dispose of old solvents on a regular periodic schedule. To avoid explosive peroxide formation, ethers should be stored in an airtight container, away from light, because both light and air can encourage peroxide formation.<ref>{{Cite web|url=https://www.uaf.edu/safety/industrial-hygiene/laboratory-safety/chem-gas/chemical-hazards/peroxides-ethers/|title=Peroxides and Ethers {{!}} Environmental Health, Safety and Risk Management|website=www.uaf.edu|language=en|access-date=25 January 2018}}</ref> A number of tests can be used to detect the presence of a peroxide in an ether; one is to use a combination of [[iron(II) sulfate]] and [[potassium thiocyanate]]. The peroxide is able to [[oxidize]] the Fe<sup>2+</sup> ion to an Fe<sup>3+</sup> ion, which then forms a deep-red [[coordination complex]] with the [[thiocyanate]]. Peroxides may be removed by washing with acidic iron(II) sulfate, filtering through [[alumina]], or [[distillation|distilling]] from [[sodium]]/[[benzophenone]]. Alumina degrades the peroxides but some could remain intact in it, therefore it must be disposed of properly.<ref>{{Cite web|url=https://ehs.ucsc.edu/lab-safety-manual/specialty-chemicals/peroxide-formers.html#removalofperoxides |title=Handling of Peroxide Forming Chemicals |language=en|access-date=24 September 2021}}</ref> The advantage of using sodium/benzophenone is that [[moisture]] and oxygen are removed as well.<ref>{{Cite journal |last1=Inoue |first1=Ryo |last2=Yamaguchi |first2=Mana |last3=Murakami |first3=Yoshiaki |last4=Okano |first4=Kentaro |last5=Mori |first5=Atsunori |date=2018-10-31 |title=Revisiting of Benzophenone Ketyl Still: Use of a Sodium Dispersion for the Preparation of Anhydrous Solvents |journal=ACS Omega |language=en |volume=3 |issue=10 |pages=12703–12706 |doi=10.1021/acsomega.8b01707 |issn=2470-1343 |pmc=6210062 |pmid=30411016}}</ref> ==Health effects== {{See also | Substance-induced psychosis}} General health hazards associated with solvent exposure include toxicity to the nervous system, reproductive damage, liver and kidney damage, respiratory impairment, cancer, hearing loss,<ref>{{Cite report |url=https://www.cdc.gov/niosh/docs/2018-124/pdfs/2018-124.pdf |title=Preventing Hearing Loss Caused by Chemical (Ototoxicity) and Noise Exposure |date=2018-03-08 |access-date=2024-11-15}}</ref><ref>{{cite journal | url=https://pubmed.ncbi.nlm.nih.gov/16938795/ | pmid=16938795 | date=2006 | last1=Fuente | first1=A. | last2=McPherson | first2=B. | title=Organic solvents and hearing loss: The challenge for audiology | journal=International Journal of Audiology | volume=45 | issue=7 | pages=367–381 | doi=10.1080/14992020600753205 }}</ref> and [[dermatitis]].<ref>{{cite web|url = https://www.osha.gov/SLTC/solvents/index.html |publisher = U.S. Department of Labor |website= Occupational Safety & Health Administration |title = Solvents|url-status = live | archive-url=https://web.archive.org/web/20160315034707/https://www.osha.gov/SLTC/solvents/index.html |archive-date=15 March 2016 }}</ref> ===Acute exposure=== Many solvents{{which?|date=November 2023}} can lead to a sudden loss of consciousness if [[inhalation|inhaled]] in large amounts.{{cn|date=November 2023}} Solvents like [[diethyl ether]] and [[chloroform]] have been used in medicine as [[anesthetics]], [[sedatives]], and [[hypnotics]] for a long time.{{when?|date=March 2024}} Many solvents (e.g. from [[gasoline]] or solvent-based glues) are abused recreationally in [[Volatile substance abuse|glue sniffing]], often with harmful long-term health effects such as [[neurotoxicity]] or [[cancer]]. Fraudulent substitution of [[1,5-pentanediol]] by the psychoactive [[1,4-butanediol]] by a subcontractor caused the [[Bindeez]] product recall.<ref>{{Cite web|url=https://www.theage.com.au/news/national/recall-for-toy-that-turns-into-drug/2007/11/06/1194329225773.html|title=National: Recall ordered for toy that turns into drug|website=www.theage.com.au|language=en|last = Rood|first = David|date=7 November 2007}}</ref> [[Ethanol]] (grain alcohol) is a widely used and abused [[psychoactive drug]]. If ingested, the so-called "toxic alcohols" (other than ethanol) such as [[methanol]], [[1-propanol]], and [[ethylene glycol]] metabolize into toxic aldehydes and acids, which cause potentially fatal [[metabolic acidosis]].<ref name="Kraut_2018">{{cite journal | vauthors = Kraut JA, Mullins ME | title = Toxic Alcohols | journal = The New England Journal of Medicine | volume = 378 | issue = 3 | pages = 270–280 | date = January 2018 | pmid = 29342392 | doi = 10.1056/NEJMra1615295 | s2cid = 36652482 }}</ref> The commonly available alcohol solvent methanol can cause permanent blindness or death if ingested. The solvent [[2-Butoxyethanol|2-butoxyethanol]], used in [[fracking fluid]]s, can cause [[hypotension]] and metabolic acidosis.<ref>{{cite journal | vauthors = Hung T, Dewitt CR, Martz W, Schreiber W, Holmes DT | title = Fomepizole fails to prevent progression of acidosis in 2-butoxyethanol and ethanol coingestion | journal = Clinical Toxicology | volume = 48 | issue = 6 | pages = 569–71 | date = July 2010 | pmid = 20560787 | doi = 10.3109/15563650.2010.492350 | s2cid = 23257894 }}</ref> ===Chronic exposure=== {{main|Chronic solvent-induced encephalopathy}} Chronic solvent exposures are often caused by the inhalation of solvent vapors, or the ingestion of diluted solvents, repeated over the course of an extended period. Some solvents can damage internal organs like the [[liver]], the [[kidney]]s, the [[nervous system]], or the [[Human brain|brain]]. The cumulative brain effects of long-term or repeated exposure to some solvents is called [[chronic solvent-induced encephalopathy]] (CSE).<ref>{{Cite journal |last1=van der Laan |first1=Gert |last2=Sainio |first2=Markku |date=2012-08-01 |title=Chronic Solvent induced Encephalopathy: A step forward |url=https://www.sciencedirect.com/science/article/pii/S0161813X12000885 |journal=NeuroToxicology |series=Neurotoxicity and Neurodegeneration: Local Effect and Global Impact |volume=33 |issue=4 |pages=897–901 |doi=10.1016/j.neuro.2012.04.012 |pmid=22560998 |bibcode=2012NeuTx..33..897V |issn=0161-813X|url-access=subscription }}</ref> Chronic exposure to organic solvents in the work environment can produce a range of adverse neuropsychiatric effects. For example, occupational exposure to organic solvents has been associated with higher numbers of painters suffering from [[alcoholism]].<ref name="pmid1606027">{{cite journal | vauthors = Lundberg I, Gustavsson A, Högberg M, Nise G | title = Diagnoses of alcohol abuse and other neuropsychiatric disorders among house painters compared with house carpenters | journal = British Journal of Industrial Medicine | volume = 49 | issue = 6 | pages = 409–15 | date = June 1992 | pmid = 1606027 | pmc = 1012122 | doi = 10.1136/oem.49.6.409 }}</ref> Ethanol has a [[synergy|synergistic]] effect when taken in combination with many solvents; for instance, a combination of [[toluene]]/[[benzene]] and ethanol causes greater [[nausea]]/[[vomiting]] than either substance alone. Some organic solvents are known or suspected to be cataractogenic. A mixture of [[aromatic hydrocarbons]], [[aliphatic hydrocarbons]], [[Alcohol (chemistry)|alcohols]], [[Ester|esters]], [[Ketone|ketones]], and [[Terpene|terpenes]] were found to greatly increase the risk of developing [[cataract]]s in the lens of the eye.<ref>{{cite journal | vauthors = Raitta C, Husman K, Tossavainen A | title = Lens changes in car painters exposed to a mixture of organic solvents | journal = Albrecht von Graefes Archiv für Klinische und Experimentelle Ophthalmologie. Albrecht von Graefe's Archive for Clinical and Experimental Ophthalmology | volume = 200 | issue = 2 | pages = 149–56 | date = August 1976 | pmid = 1086605 | doi = 10.1007/bf00414364 | s2cid = 31344706 }}</ref> ===Environmental contamination=== A major pathway of induced health effects arises from spills or leaks of solvents, especially [[Organochlorine chemistry|chlorinated solvents]], that reach the underlying soil. Since solvents readily migrate substantial distances, the creation of widespread [[soil contamination]] is not uncommon; this is particularly a health risk if [[aquifer]]s are affected.<ref>{{Cite journal |last1=Matteucci |first1=Federica |last2=Ercole |first2=Claudia |last3=del Gallo |first3=Maddalena |date=2015 |title=A study of chlorinated solvent contamination of the aquifers of an industrial area in central Italy: a possibility of bioremediation |journal=Frontiers in Microbiology |volume=6 |page=924 |doi=10.3389/fmicb.2015.00924 |pmid=26388862 |pmc=4556989 |issn=1664-302X |doi-access=free }}</ref> [[Vapor intrusion]] can occur from sites with extensive subsurface solvent contamination.<ref>{{cite journal | vauthors = Forand SP, Lewis-Michl EL, Gomez MI | title = Adverse birth outcomes and maternal exposure to trichloroethylene and tetrachloroethylene through soil vapor intrusion in New York State | journal = Environmental Health Perspectives | volume = 120 | issue = 4 | pages = 616–21 | date = April 2012 | pmid = 22142966 | pmc = 3339451 | doi = 10.1289/ehp.1103884 }}</ref> == See also == {{Commons category|Solvents}} * [[ASTDR]] * [[Construction]] | [[Refurbishment (disambiguation)|Refurbishment]] | [[Renovation]] * [[Free energy of solvation]] * [[International Agency for Research on Cancer | IARC]] * Solvents are often refluxed with an appropriate [[desiccant]] prior to distillation to remove water. This may be performed prior to a chemical synthesis where water may interfere with the intended reaction * [[List of water-miscible solvents]] * [[Lyoluminescence]] * [[Occupational health]] * [[Partition coefficient]] (log ''P'') is a measure of differential solubility of a compound in two solvents * [[Pollution]] * [[Solvation]] * Solvent systems exist outside the realm of ordinary organic solvents: [[Supercritical fluid]]s, [[ionic liquid]]s and [[deep eutectic solvent]]s * [[Superfund]] * [[Volatile Organic Compound]] * [[Water model]] * [[Water pollution]] {{Anchor|Desiccant}} == References == {{Reflist|30em}} ==Bibliography== * {{cite book | vauthors = Lowery TH, Richardson KS | title = Mechanism and Theory in Organic Chemistry | publisher = [[Harper Collins Publishers]] | edition = 3rd | date = 1987 | isbn = 978-0-06-364044-3 }} == External links == {{Wiktionary|solvent}} *[https://www.acs.org/content/acs/en/greenchemistry/research-innovation/tools-for-green-chemistry/solvent-tool.html Solvent selection tool] ACS Green Chemistry Institute *[http://www.esig.org "European Solvents Industry Group - ESIG - ESIG European Solvents Industry Group"] Solvents in Europe. *[https://web.archive.org/web/20041113054037/http://www.usm.maine.edu/~newton/Chy251_253/Lectures/Solvents/Solvents.html Table and text] O-Chem Lecture *[https://web.archive.org/web/20041207190740/http://virtual.yosemite.cc.ca.us/smurov/orgsoltab.htm Tables] Properties and toxicities of organic solvents *[https://www.cdc.gov/niosh/topics/organsolv/ CDC – Organic Solvents – NIOSH Workplace Safety and Health Topic] *[https://www.epa.gov/hwgenerators/final-rule-2013-conditional-exclusions-solid-waste-and-hazardous-waste-solvent EPA – Solvent Contaminated Wipes] {{Reaction mechanisms}} {{Chemical solutions}} {{Authority control}} [[Category:Soil contamination]] [[Category:Solvents| ]] [[Category:Solutions]] [[Category:Chemical compounds]] [[he:תמיסה#הממס]] [[Category:Polymer physics]]
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