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==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}}</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 |}
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