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Solvent - Wikipedia, The Free Encyclopedia PDF
Solvent - Wikipedia, The Free Encyclopedia PDF
Solvent - Wikipedia, The Free Encyclopedia PDF
http://en.wikipedia.org/wiki/Solvent
Solvent
From Wikipedia, the free encyclopedia Jump to: navigation, search For other uses, see Solvent (disambiguation). A solvent (from the Latin solvere, "loosen") is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution 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 a paint thinner (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 nail polish, (part of how it stays on nails) and in chemical synthesis. The use of inorganic solvents (other than water) is typically limited to research chemistry and some technological processes. In 2005, the worldwide market for solvents had a total volume of around 17.9 million tons, which led to a turnover of about 8 billion Euro.[citation needed]
Contents
1 Solutions and solvation 2 Solvent classifications 2.1 Other polarity scales 2.2 Polar protic and polar aprotic 3 Physical properties of common solvents 3.1 Properties table of common solvents 3.2 Boiling point 3.3 Density 4 Health and safety 4.1 Fire 4.2 Explosive peroxide formation 4.3 Health effects 4.3.1 General precautions 4.4 Environmental contamination 5 See also 6 References 7 Bibliography 8 External links
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the solvent arrange themselves around molecules of the solute. Heat is involved and entropy is increased making the solution more thermodynamically stable than the solute alone. This arrangement is mediated by the respective chemical properties of the solvent and solute, such as hydrogen bonding, dipole moment and polarizability.[2]
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Non-polar solvents Pentane Cyclopentane Hexane Cyclohexane Benzene Toluene 1,4-Dioxane Chloroform Diethyl ether CH3-CH2CH2-CH2-CH3 C5H10 CH3-CH2-CH2-CH2CH2-CH3 C6H12 C6H6 C6H5-CH3 /-CH2-CH2-OCH2-CH2-O-\ CHCl3 CH3CH2-O-CH2-CH3 36 C 40 C 69 C 81 C 80 C 111 C 101 C 61 C 35 C 1.84 1.97 1.88 2.02 2.3 2.38 2.3 4.81 4.3 0.626 g/ml 0.751 g/ml 0.655 g/ml 0.779 g/ml 0.879 g/ml 0.867 g/ml 1.033 g/ml 1.498 g/ml 0.713 g/ml 1.3266 g/ml 0.886 g/ml 0.894 g/ml 0.786 g/ml 0.00 D 0.00 D 0.00 D 0.00 D 0.00 D 0.36 D 0.45 D 1.04 D 1.15 D
Polar aprotic solvents Dichloromethane (DCM) Tetrahydrofuran (THF) Ethyl acetate Acetone CH2Cl2 /-CH2-CH2-OCH2-CH2-\ CH3-C(=O)-OCH2-CH3 CH3-C(=O)-CH3 40 C 66 C 77 C 56 C 9.1 7.5 6.02 21 1.60 D 1.75 D 1.78 D 2.88 D
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Dimethylformamide (DMF) Acetonitrile (MeCN) Dimethyl sulfoxide (DMSO) Formic acid n-Butanol Isopropanol (IPA) n-Propanol Ethanol Methanol Acetic acid Water
153 C 82 C 189 C
38 37.5 46.7
0.944 g/ml 0.786 g/ml 1.092 g/ml 1.21 g/ml 0.810 g/ml 0.785 g/ml 0.803 g/ml 0.789 g/ml 0.791 g/ml 1.049 g/ml 1.000 g/ml
Polar protic solvents H-C(=O)OH CH3-CH2-CH2-CH2-OH CH3-CH(-OH)-CH3 CH3-CH2-CH2-OH CH3-CH2-OH CH3-OH CH3-C(=O)OH H-O-H 101 C 118 C 82 C 97 C 79 C 65 C 118 C 100 C 58 18 18 20 24.55 33 6.2 80 1.41 D 1.63 D 1.66 D 1.68 D 1.69 D 1.70 D 1.74 D 1.85 D
There's another powerful way to look at these same solvents. By knowing their Hansen solubility parameter values (HSPiP),[9][10] which are based on D=dispersion bonds, P=polar bonds and H=hydrogen bonds, you know important things about their inter-molecular interactions with other solvents and also with polymers, pigments, nanoparticles etc. so you can do two things. First, you can create rational formulations knowing, for example, that there is a good HSP match between a solvent and a polymer. Second, you can make rational substitutions for "good" solvents (they dissolve things well) that are "bad" (for the environment, for health, for cost etc.). 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 P and the protic solvents have higher levels of H. Because numerical values are used, comparisons can be made rationally by comparing numbers. So acetonitrile is much more polar than acetone but slightly less hydrogen bonding. Solvent Chemical formula D Dispersion P Polar H Hydrogen bonding
Non-polar solvents Hexane Benzene CH3-CH2-CH2-CH2CH2-CH3 C6H6 14.9 18.4 0.0 0.0 0.0 2.0
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Toluene Diethyl ether Chloroform 1,4-Dioxane Ethyl acetate Tetrahydrofuran (THF) Dichloromethane Acetone Acetonitrile (MeCN) Dimethylformamide (DMF) Dimethyl sulfoxide (DMSO) Acetic acid n-Butanol Isopropanol n-Propanol Ethanol Methanol Formic acid Water
C6H5-CH3 CH3CH2-O-CH2-CH3 CHCl3 /-CH2-CH2-O-CH2-CH2-O-\ CH3-C(=O)-O-CH2-CH3 /-CH2-CH2-O-CH2-CH2-\ CH2Cl2 CH3-C(=O)-CH3 CH3-CN H-C(=O)N(CH3)2 CH3-S(=O)-CH3
18.0 14.5 17.8 17.5 15.8 16.8 17.0 15.5 15.3 17.4 18.4
1.4 2.9 3.1 1.8 5.3 5.7 7.3 10.4 18.0 13.7 16.4
2.0 4.6 5.7 9.0 7.2 8.0 7.1 7.0 6.1 11.3 10.2
Polar protic solvents CH3-C(=O)OH CH3-CH2-CH2-CH2-OH CH3-CH(-OH)-CH3 CH3-CH2-CH2-OH CH3-CH2-OH CH3-OH H-C(=O)OH H-O-H 14.5 16.0 15.8 16.0 15.8 14.7 14.6 15.5 8.0 5.7 6.1 6.8 8.8 12.3 10.0 16.0 13.5 15.8 16.4 17.4 19.4 22.3 14.0 42.3
Consider a simple example of rational substitution. Suppose for environmental reasons we needed to replace the chlorinated solvent, chloroform, with a solvent (blend) of equal solvency using a mixture of two non-chlorinated solvents from this table. Via trial-and-error, a spreadsheet or some software such as HSPiP[9][10] we find that a 50:50 mix of toluene and 1,4 dioxane is a close match. The D of the mixture is the average of 18.0 and 17.5 = 17.8. The P of the mixture is the average of 1.4 and 1.8 = 1.6 and the H of the mixture is the average of 2.0 and 9.0 = 5.5. So the mixture is 17.8, 1.6, 5.5 compared to Chloroform at 17.8, 3.1, 5.7. Because Toluene itself has many health issues, other mixtures of solvents can be found using a full Hansen solubility parameter dataset.
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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.
Boiling point (C)[7] ethylene dichloride 83.48 Low boilers: boiling temperature below 100 C (boiling pyridine 115.25 point of water) methyl isobutyl ketone 116.5 Medium boilers: between 100 C and 150 C methylene chloride 39.75 High boilers: above 150 C isooctane 99.24 [edit] Density carbon disulfide 46.3 carbon tetrachloride 76.75 Most organic solvents have a lower density than water, which o-xylene 144.42 means they are lighter and will form a separate layer on top of water. An important exception: most of the 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. Solvent 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. Solvent Pentane Petroleum ether Hexane Heptane Diethyl amine Diethyl ether Triethyl amine Tert-butyl methyl ether Cyclohexane Tert-butyl alcohol Isopropanol Acetonitrile Ethanol Acetone Methanol Methyl isobutyl ketone Isobutyl alcohol 1-Propanol Methyl ethyl ketone Specific gravity[11] 0.626 0.656 0.659 0.684 0.707 0.713 0.728 0.741 0.779 0.781 0.785 0.786 0.789 0.790 0.791 0.798 0.802 0.803 0.805
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2-Butanol Isoamyl alcohol 1-Butanol Diethyl ketone 1-Octanol p-Xylene m-Xylene Toluene Dimethoxyethane Benzene Butyl acetate 1-Chlorobutane Tetrahydrofuran Ethyl acetate o-Xylene Hexamethylphosphorus triamide 2-Ethoxyethyl ether N,N-Dimethylacetamide Diethylene glycol dimethyl ether N,N-Dimethylformamide 2-Methoxyethanol Pyridine Propanoic acid Water 2-Methoxyethyl acetate Benzonitrile 1-Methyl-2-pyrrolidinone Hexamethylphosphoramide 1,4-Dioxane Acetic acid Acetic anhydride Dimethyl sulfoxide Chlorobenzene Deuterium oxide Ethylene glycol Diethylene glycol Propylene carbonate Formic acid
0.808 0.809 0.810 0.814 0.826 0.861 0.864 0.867 0.868 0.879 0.882 0.886 0.889 0.895 0.897 0.898 0.909 0.937 0.943 0.944 0.965 0.982 0.993 1.000 1.009 1.01 1.028 1.03 1.033 1.049 1.08 1.092 1.1066 1.107 1.115 1.118 1.21 1.22
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1,2-Dichloroethane Glycerin Carbon disulfide 1,2-Dichlorobenzene Methylene chloride Nitromethane 2,2,2-Trifluoroethanol Chloroform 1,1,2-Trichlorotrifluoroethane Carbon tetrachloride Tetrachloroethylene
1.245 1.261 1.263 1.306 1.326 1.382 1.393 1.498 1.575 1.594 1.623
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up quickly; they are more of a problem for laboratories which take years to finish a single bottle. Ethers have to be stored in the dark in closed canisters in the presence of stabilizers like butylated hydroxytoluene (BHT) or over sodium hydroxide. Peroxides may be removed by washing with acidic iron(II) sulfate, filtering through alumina, or distilling from sodium/benzophenone. Alumina does not destroy the peroxides; it merely traps them. The advantage of using sodium/benzophenone is that moisture and oxygen is removed as well.
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Wikimedia Commons has media related to: Solvents 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 model Water pollution 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. Occupational health Lyoluminescence Solvation Solution
[edit] References
1. ^ Tinoco, Sauer, Wang & Puglisi, Physical Chemistry Prentice Hall 2002 p. 134 ISBN 0130266078 2. ^ Lowery and Richardson, pp. 181-183 3. ^ a b Lowery and Richardson, p. 177. 4. ^ Kosower, E.M. "An introduction to Physical Organic Chemistry" Wiley: New York, 1969 p. 293 5. ^ Gutmann, V. (1976). "Solvent effects on the reactivities of organometallic compounds". Coord. Chem. Rev. 18 (2): 225. doi:10.1016/S0010-8545(00)82045-7. 6. ^ Lowery and Richardson, p. 183. 7. ^ a b Solvent Properties - Boiling Point 8. ^ Dielectric Constant 9. ^ a b Steven Abbott and Charles M. Hansen Hansen Solubility Parameters in Practice, ISBN 0955122023 (2008) 10. ^ a b Charles M. Hansen Hansen solubility parameters: a user's handbook CRC Press, 2007, ISBN 0849372488 11. ^ Selected solvent properties - Specific Gravity 12. ^ U.S. Department of Labor > Occupational Safety & Health Administration > Solvents Page current as of: 29 August 2007 13. ^ Lundberg I, Gustavsson A, Hgberg M, Nise G (June 1992). "Diagnoses of alcohol abuse and other neuropsychiatric disorders among house painters compared with house carpenters". Br J Ind Med 49 (6): 40915. PMC 1012122. PMID 1606027.
[edit] Bibliography
Lowery, T.H. and Richardson, K.S., Mechanism and Theory in Organic Chemistry , Harper Collins Publishers 3rd ed. 1987 ISBN 0063640449
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Concentration Molar concentration Mass concentration Number concentration Volume concentration and related Normality Percentage solution Molality Mole fraction Mass fraction Mixing ratio quantities Solubility equilibrium Total dissolved solids Solvation Solvation shell Enthalpy of Solubility solution Lattice energy Raoult's law Henry's law Solubility table (data) Solubility chart (category) Acid dissociation constant Protic solvent Inorganic nonaqueous solvent Solvation List of boiling and freezing information of solvents Solvent Partition coefficient Polarity Hydrophobe Hydrophile Lipophilic Amphiphile Retrieved from "http://en.wikipedia.org/wiki/Solvent" Categories: Chemical reactions | Soil contamination | Solvents | Solutions | Chemical compounds Hidden categories: All articles with unsourced statements | Articles with unsourced statements from March 2009 | Articles with unsourced statements from February 2011 | Use dmy dates from September 2010
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