Download - Immiscible Solvents
Immiscible solvents
SOLVENTS Immiscibility
Acetone can be mixed with any of the solvents listed in the column at left
Acetonitrile cyclohexane, heptane, hexane, pentane, 2,2,4-trimethylpentane
carbon tetrachloride
can be mixed with any of the solvents listed in the column at left except water
chloroform can be mixed with any of the solvents listed in the column at left except water
cyclohexane acetonitrile, dimethyl formamide, dimethyl sulfoxide, methanol, water
1,2-dichloroethane can be mixed with any of the solvents listed in the column at left except water
dichloromethane can be mixed with any of the solvents listed in the column at left except water
diethyl ether dimethyl sulfoxide, water
dimethyl formamide cyclohexane, heptane, hexane, pentane, 2,2,4-trimethylpentane, water
dimethyl solfoxide cyclohexane, heptane, hexane, pentane, 2,2,4-trimethylpentane, diethyl ether
1,4-dioxane can be mixed with any of the solvents listed in the column at left
ethanol can be mixed with any of the solvents listed in the column at left
ethyl acetate can be mixed with any of the solvents listed in the column at left except water
heptane acetonitrile, dimethyl formamide, dimethyl sulfoxide, methanol, water
hexane acetonitrile, dimethyl formamide, dimethyl sulfoxide, methanol, acetic acid, water
methanol cyclohexane, heptane, hexane, pentane, 2,2,4-trimethylpentane
methyl-tert-butyl ether
can be mixed with any of the solvents listed in the column at left except water
pentane acetonitrile, dimethyl formamide, dimethyl sulfoxide, methanol, water, acetic acid
1-propanol can be mixed with any of the solvents listed in the column at left
2-propanol can be mixed with any of the solvents listed in the column at left
tetrahydrofuran can be mixed with any of the solvents listed in the column at left
toluene can be mixed with any of the solvents listed in the column at left except water
2,2,4-trimethylpentane
acetonitrile, dimethyl formamide, dimethyl sulfoxide, methanol, water
watercarbon tetrachloride, chloroform, cyclohexane, 1,2-dichloroethane, dichloromethane, diethyl ether, dimethyl formamide, ethyl acetate, heptane, hexane, methyl-tert-butyl ether, pentane, toluene, 2,2,4-trimethylpentane
Solvents Drying and Drying Agents
Removing water from Solvents
There are various ways of removing water and other impurities from a solution. This can become a major task once the used reagents are also sensitive towards water e.g. Grignard reagents or enolates. If water is one of the products, it also has a detrimental effect on the yield and/or reaction rate. In those cases, drying agents like activated alumina¹, calcium hydride (CaH2), sodium metal (in combination with benzophenone which forms a dark blue ketyl radical), lithium aluminum hydride (LiAlH4) or phosphorous pentoxide (P4O10) are used to chemically destroy the water. The drying agents commonly used in the organic laboratories are the anhydrous forms of calcium chloride (CaCl2), sodium sulfate (Na2SO4) Calcium sulfate (CaSO4 (as Drierite) and magnesium sulfate (MgSO4).Organic liquids are considered to be wet if they contain water,but the organic liquid will still be a liquid after it is dried.
Activated Alumina
Activated alumina ¹ is a very porous form of aluminum oxide of high surface area which adsorbs liquids and gases without any change in form. Activated alumina will not soften or disintegrate when immersed in liquids. Activated alumina may be regenerated to its original adsorption efficiency by heating to a temperature between (177-316°C).
Activated alumina can be used for:
Reconditioning of mineral oils like transformer or insulating oils. Removal of oil vapor mist from compressed air. Drying of organic liquids to a moisture level of 10 ppm or below.Drying of various liquids such as Benzene, Carbon, Tetrachloride, Chlorobenzene, Ethyl Acetate, Transformer oil, Vegetable oils etc.
Solvents drying guide
TO DRY USE ONE OF THE FOLLOWING DRYING AGENTS
AlcoholsAnhydrous forms of potassium carbonate; anhydrous magnesium or calcium sulphate; quicklime.
Alkyl halidesAryl halides
Anhydrous calcium chloride; anhydrous forms of sodium sulphate, magnesium sulphate, or calcium sulphate; sodium pentoxide.
Saturated andAromatic hydrocarbons
Anhydrous calcium chloride or sulphate; metallic sodium; phosphorus pentoxide.
AldehydesAnhydrous sodium sulphate; anhydrous magnesium or calcium sulphate.
KetonesAnhydrous sodium sulphate; anhydrous magnesium or calcium sulphate; anhydrous potassium carbonate.
Organic bases(amines)
Solid potassium or sodium hydroxide; quicklime; barium oxide.
Organic acidsAnhydrous sodium sulphate; anhydrous magnesium or calcium sulphate.
Solvents: Properties and Drying agents
SolventBoiling
Pt.°C
DensityFlash
Pt.°C
Drying agent
Acetone 56 0.791 -18 K2CO3; Molecular sieve 0.3nm; CaCl2
Acetic acid 118 1.049 +40 P2O5; CuSO4
Acetic anhydride 136 1.082 +49 CaCl2
Acetonitrile 82 0.782 +6CaCl2; P2O5; K2CO3; calcium hydride; Molecular sieve 0.3nm
Aniline 184 1.022 +76 KOH; BaO
Anisole 154 0.995 +51 CaCl2; Na; distillation
Benzene 80 0.879 -10CaCl2; distillation; Na; Pb/Na; ; calcium hydride; Na wire; Molecular sieve 0.4nm
1-Butanol 117 0.810 +29 K2CO3; distillation
2-Butanol 100 0.808 +24 K2CO3; distillation
tert-Butanol 82 0.882 +11 CaO; Freezing
n-Butyl acetate 127 0.882 +33 MgSO4;
Carbon disulphide 46 1.263 -30 CaCl2P2O5;
Carbon tetrachloride 77 1.594 none distillation; P2O3; Pb/Na; Molecular sieve 0.4nm
Chlorobenzene 132 1.106 +29 CaCl2; distillation;P2O5
Chloroform 62 1.486 none CaCl2; P2O5; Pb/Na; Molecular sieve 0.4nm
Cyclohexane 81 0.799 none Na; Na/Pb; LiAlH4; Molecular sieve 0.4nm
Cyclohexanone 155 na na Distillation
Decahydronaphthalene(Dekalin)
~190 0.886 <54 CaCl2; Na; Pb/Na
Dichloromethane 40 1.325 none CaCl2; Pb/Na; calcium hydride; Molecular sieve 0.4nm
Dicyclopentadiene:(cyclopentadiene dimer)
170 na naRefractionation: distillate at 40 - 42°C. (Use at once! or keep in dry ice/acetone bath no longer than 1 Hr.)
Diethyl carbonate 126 0.975 +25 Na2SO4; K2CO3
Diethylene glycoldibutyl ether
225 0.885 +118 CaCl2; Na
Diethylene glycol dimethyl ether
155165
0.906 +70 CaCl2; Na
Diethyl ether 34 0.714 -40CaCl2; Na; Pb/Na; LiAlH4; Na wire/benzophenone; Molecular sieve 0.4nm
Di-isopropyl ether 68 0.726 -23 CaCl2; Na; Molecular sieve 0.4nm
Dimethyl formamide 153 0.950 +62 distillation; Molecular sieve 0.4nm
Dimethyl sulfoxide 189 1.101 +95 distillation; Molecular sieve 0.4nm
1,4 Dioxane 101 1.034 +11.8 CaCl2; Na; Molecular sieve 0.4nm
Ethanol 79 0.791 +12 CaO; Mg; MgO; Molecular sieve 0.3nm
Ethyl acetate 77 0.901 -4K2CO3; P2O5; Na2SO4; calcium hydride; Molecular sieve 0.4nm
Ethylenediamine:(1-2 diaminoethane)
118 na na Simple distillation.
Ethylene glycol 197 1.109 +111 distillation; Na2SO4
Ethylene glycol monoethyl ether
135 0.930 +41 distillation
Ethylene glycol monomethyl ether
125 0.965 +52 distillation
Ethyl formate 54 0.924 -20 MgSO4; Na2SO4;
Formamide 211 1.134 155 Na2SO4; CaO
Glycerol 290 1.260 +176 distillation
Heptane 98 0.684 -4 calcium hydride; Na wire
n-Hexane 69 0.659 -23Na; Pb/Na; LiAlH4; calcium hydride; Na wire/benzophenone; Molecular sieve 0.4nm
Isobutanol 108 0.803 +28 K2CO3; CaO; Mg;
Isobutyl methyl ketone 117 0.801 +15.5-4 K2CO3;
Methanol 65 0.792 +11 Mg; CaO; Molecular sieve 0.3nm
Methyl acetate 57 0.933 -10 K2CO3; CaO;
1-Methyl-2-pyrrolidone 202 1.026 +95 Na2SO4; distillation; Molecular sieve 0.4nm
Methyl Ethyl ketone 80 0.806 -44 K2CO3;
Nitrobenzene 211 1.204 +92 CaCl2; P2O5; distillation;
n-Pentane 36 0.626 -49 Na; Pb/Na;calcium hydride; Na wire
Pet ether mixture na nacalcium hydride; Na wire/benzophenone; Molecular sieve type 4A
1- Propanol 97 0.804 +15 CaO; Mg
2-Propanol 82 0.785 +12 CaO; Mg; Molecular sieve 0.3nm
Pyridine 116 0.982 +20 KOH; BaO; Molecular sieve 0.4nm
Tetrahydrofuran 66 0.887 -17.5 Molecular sieve 0.4nm
Tetrahydronaphthalene(Tetralin)
208 0.973 CaCl2; Na
Thionyl chloride 48 na na Redistill.
Toluene 111 0.867 +4 distillation; Ca; CaCl2; Na; Molecular sieve 0.4nm
Trichloroethylene 87 1.462 none distillation; Na2SO4; K2CO3
Xylene 137/140 -0.86 +25 distillation; Na; CaCl2; Molecular sieve 0.4nm
Storage of Incompatible Chemicals
Substance Incompatible with
Acetic acidChromium oxide, nitric acid, perchloric acid, peroxides, permanganates, alcohol, ethylene glycol
Acetic anhydride Hydroxyl-containing compounds e.g. ethylene glycol, perchloric acid
Acetone Concentrated nitric acid and sulphuric acid mixtures, hydrogen peroxide
Acetylene Chlorine, bromine, fluorine, copper, silver, mercury
Activated carbon Calcium hypochlorite, oxidizing agents
Alkali metalsWater, carbon tetrachloride and other halogenated alkanes, carbon dioxide, halogens. (Do not use water or foam extinguishers for fires involving these metals Use the appropriate class D extinguisher.
Aluminium All oxidizing agents, acids, alkalis, halogenated hydrocarbons, peroxides
Aluminium alkyls water
Ammonia, liquid or gas
Mercury (e.g. in pressure gauges), chlorine, calcium hypochlorite, iodine, bromine, hydrogen fluoride
Ammonium nitrateAcids, powdered metals, flammable liquids, chlorates, nitrates, sulfur, fine-particulate organic or combustible materials
Aniline Nitric acid, hydrogen peroxide
Arsenic materials Any reducing agent
Azides Acids
Bromine see chlorine
Calcium oxide Water
Carbon activated Calcium hypochlorite, other oxidants
ChlorineAmmonia, acetylene, butadiene, butane, methane, propane, hydrogen, petroleum benzine, benzene, powdered metals
ChloratesAmmonium salts, acids, powdered metals, sulfur, fine-particulate organic or combustible substances
Chromium (V1) oxide, chromic acid
Acetic acid, naphthalene, camphor, glycerol, petroleum benzine, alcohols, flammable liquids
Copper Acetylene, hydrogen peroxide
Cumene hydroperoxide
Acids, both organic and inorganic
Cyanides Acids
Flammable liquidsAmmonium nitrate, chromium (VI) oxide, hydrogen peroxide, nitric acid, sodium peroxide, halogens, chromic acid.
Fluorine Extremely aggressive; store separately! Isolate from everything!
Hydrazine Hydrogen peroxide, nitric acid, any other oxidant
Hydrocarbonsbutane, propane, benzene etc.
Fluorine, chlorine, bromine, chromium (VI) oxide, sodium peroxide
Hydrogen fluoride Ammonia (laboratory gas or solutions)
Hydrogen peroxideCopper, chromium, iron, metals and metal salts, alcohols, acetone, organic substances, aniline, nitromethane, combustible substances (solid or liquid)
Hydrogen sulphide Fuming nitric acid, oxidizing gases
Hypochlorites Acids, activated carbon
Iodine Acetylene, ammonia (laboratory gas or solutions)
Mercury Acetylene, ammonia
Nitrates and nitrites Acids
Nitric acidAcetic acid, aniline, chromium (VI) oxide, prussic acid, hydrogen sulfide, flammable liquids and gases
Nitroparaffins Inorganic bases, amines
Oxalic acid Silver, mercury, mercury salts
Perchloric acidAcetic anhydride, bismuth and its alloys, alcohols, paper, wood, grease. oil, (all organics)
Peroxides, organic Acids (organic and inorganic), avoid friction, store cold.
Phosphorus Sulfur, compounds containing oxygen, e.g. chlorates, air, oxygen
Phosphorus pentoxide
Alcohols, strong bases, water
Potassium Carbon tetrachloride,carbon dioxide, water
Potassium chlorate see chlorate
Potassium perchlorate
see chlorate
Potassium permanganate
Glycerol, ethylene glycol, benzaldehyde, sulfuric acid
Silver Acetylene, oxalic acid tartaric acid, ammonium compounds
Sodium see alkali metals
Sodium peroxideMethanol, ethanol, glacial acetic acid, acetic anhydride, benzaldehyde, carbon disulfide, glycerol, ethylene glycol, ethyl acetate, methyl acetate, furfural
Sulphides Acids
Sulphuric acid Potassium chlorate, potassium perchlorate, potassium permanganate
sulphur Metals, all oxidizing agents
Zinc All oxidizing agents, acids, alkalis, halogenated hydrocarbons, peroxides
Reactions of incompatible chemicals
Chemicals Stored Together Possible Reaction
1. Acetic acid & AcetaldehydeSmall amounts of acetic acid will cause the acetaldehyde to polymerize, releasing heat.
2. Acetic anhydride & Acetaldehyde Reaction can be violently explosive
3. Aluminum metal & ammonium nitrate
A potential explosive.
4. Aluminum & bromine vaporAluminum foil reacts with bromine vapor at room temperature and incandesces.
5. Ammonia vapor & bromine vapor Unstable nitrogen tribromide is formed, explosion may result.
6. Ammonium nitrate & acetic acidA mixture may result in ignition, especially if acetic acid is concentrated.
7. Cupric sulfide & cadmium chlorate
Will explode on contact.
8. Hydrogen peroxide & ferrous sulfide
Forms a vigorous, highly exothermic reaction.
9. Hydrogen peroxide & lead II or IV oxide
Violent, possibly explosive reaction.
10. Lead perchlorate & methyl alcohol
Forms an explosive mixture if agitated.
11. Lead sulfide & hydrogen peroxide
Vigorous, potentially explosive reaction.
12. Mercury II nitrate & methanol May form mercury fulminate - an explosive.
13. Nitric acid & phosphorus Phosphorus burns spontaneously in the presence of nitric acid.
14. Potassium cyanide & potassium peroxide
A potentially-explosive mixture if heated.
15. Sodium nitrate & sodium thiosulfate
A mixture of the dry materials can result in an explosion.
References :1. Merck chemical company.2. Chemical Safety Office, Risk Management Department, University of Vermont.3. Hazards in the Chemical Laboratory, 4th. edition. 1986. Bretherick.