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P U R IF IC A T IO N OL A B O R A T O R Y C H E

W ilfred L. F .A rm are goC h ristina U U n C hai

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METHODS OF PURIFICATION OF REAGENTS AND SOLVENTS 7

SOLVENT EXTRACTION AND DISTRIBUTION 7

DISTILLATION 8Techniques 8Distillation of liquid mixtures 9Types of distillation 10

The distilling flask 10T y pes of columns and packings 10Types of condensers 11

Vacuum distillation 11Spinning-band distillation 12Steam distillation 12 A zeotropic distillation 13Kugelrohr distillation 13 Isopiestic or isothermal distillation 14

RECRYST ALLIS ATION 14Technique s 14

Filtration 15Solvents 15

Choice of solvents 15Water 16 Petroleum eth ers 16 Mixed solv ents 16

Recrystallisation from the melt 17Zone refining 17

CHROMATOGRAPHy 18Va pour phase chromatography (GC or gas-liquid chromatography) 18Liquid chromatography 18

Adsorption chromatograph y 19Thin layer chromatography (TLC) 19Paper chromatography 20Column chromatograph y 20

Graded adsorb ents and solvents 20Preparation and standardisation of alumina 20Pr e paration of oth er adsorb ents 21

Silica 21 Diatomaceous earth 21Charcoal 21Cellulose 21Supelco products 21

Flash Chromatography (FC and HPFC) 22Paired- ion Chromatography (PIC) 22Ion-exchange Chromatography 23

Ion-exchange R esins 23 Ion-exchang e cellulos es and sephade x 24

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LIQUIDS FOR DRYING PISTOLS .44VAPOUR PRESSURES (mm Hg) OF SATURATED AQUEOUSSOLUTIONS IN EQUILIBRIUM WITH SOLID SALTS .45DRYING AGENTS FOR CLASSES OF COMPOUNDS 46

STATIC DRYING FOR SELECTED LIQUIDS (25 C) 46AQUEOUS BUFFERS 47SOLUBILITY COEFFICIENTS OF AIR AT 1atm IN WATER .48SOLUBILITY COEFFICIENTS OF O 2 AT 1atm IN WATER 48BUNSEN COEFFICIENTS (~) OF GASES AT 1atmIN ORGANIC SOLVENTS AT 20C 48OSTWALD COEFFICIENTS (l) / L OF O 2 AT 1atmIN AQUEOUS SOLUTIONS AT 25C .49SOLUBILITIES OF HCI AND NH 3 AT 760mm (g/lOOg OFSOLUTION) 50BOILING POINTS OF SOME USEFUL GASES AT 760 mm 50

PREFIXES FOR QUANTITIES 50BIBLIOGRAPHy 51

TABLE 15.TABLE 16.

TABLE 17.

TABLE 18.TABLE 19 .TABLE 20.TABLE 21.TABLE 22.

TABLE 23.

TABLE 24.

TABLE 25.

TABLE 26.

CHEMICAL METHODS USED IN PURIFICATION 61

GENERAL REMARKS 61

REMOVAL OF TRACES OF METALS FROM REAGENTS 61METAL IMPURITIES 61DISTILLATION 61SCAVENGER RESINS AND OTHER SUPPORTS 62USE OF ION EXCHANGE RESINS 62PRECIPITATION 62

Removal of lead contaminants 62Removal of iron contaminants 62Removal of other metal contaminants 63

EXTRACTION 63COMPLEXATION 63

USE OF METAL HYDRIDES 63LITHIUM ALUMINIUM HYDRIDE 63CALCIUM HyDRIDE 63SODIUM BOROHYDRIDE 63POTASSIUM BOROHYDRIDE 64

PURIFICATION via DERIV ATIVES 64ALCOHOLS 64ALDEHYDES 65AMINES 65

Picrate s 65

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Salt s 65Double salts 66 N- Acetyl derivative s 66 N- To sy I derivative s 66

AROMATIC HyDROCARBONS 66Adduct s 66Sulfonation 66

CARBOXYLIC ACIDS 664-Bromophenacy I esters 66Alkyl e ster s 66Salt s 67

HYDRO PEROXIDES 67KETONES 67

Bisulfite adduct 67Semicarba zone s 67

PHENOLS 67Benzoat es 67Acetat es 68

PHOSPHATE AND PHOSPHONATE ESTERS 6 8MISC ELLANEOUS 68

GENERAL METHODS FOR THE PURIFICATION OF CLASSES OF COMPOUNDS 68PROCEDURES 68CRITERIA OF PURITY 69

GENERAL PROCEDURES FOR THE PURIFICATION OF SOME CLASSES OFORGANIC COMPOUNDS 69

ACETALS 70ACIDS 70Carbo xylic acid s 70Sulfonic acid s 70Sulfinic acids 70

ACID CHLORIDES 71ALCOHOLS 71

Monohydric alcohols , 71Polyhydric alcohol s 71

ALDEHYDES 71AMI DES 71AMINES 72AMINO ACIDS 72ANHYDRIDES 7 2CAROTENOIDS 72ESTERS 7 3ETHERS 7 3HALIDES 74HyDROCARBONS 74IMIDES 75IMINO COMPOUNDS 75KETONES 75MACROMOLECULES 75

NITRILES 75

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NITRO COMPOUNDS 76 NUCLEIC ACIDS 76PHENOLS 76POLYPEPTIDES AND PROTEINS 76

QUINONES 76SALTS 76

With metal ions 76With organic cation s 77With sodium alkane sulfonate s 77

SULFUR COMPOUNDS 77Disulfides 77Sulfone s 77Sul f oxides 77Thioether s (sulfide s) 77Thiols 77Thiolsulfonates (disulfoxides) 77

THE FUTURE OF PURIFICATION 80

INTRODUCTION 80

ORGANOCATAL YSIS 80

MICROWAVE T ECHNOLOGIES 81

SOLID PHASE S y NTHESIS 81SOLID PHAS E PEPTIDE SYNTHESIS (SPPS) 82SOLID PHAS E DEOXYRIBONUCLEOTIDE SYNTHESIS 82POLYMER SUPPORTED REACTANTS 82SCAVENGER RESINS 82COMBINATORIAL CHEMISTRy 83

ALTERNATI VE SOLVENTS 83

SUPERCRITICAL FLUIDS 8 3IONIC LIQUIDS 84FLUOROUS CHEMISTRY 84

BIBLIOGRAPHy 85

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PURIFICATION OF ORGANIC CHEMICALS

INTRODUCTION 88ALIPHATIC COMPOUNDS 89ALICYCLIC COMPOUNDS 194AROMATIC COMPOUNDS 223HETEROCYCLIC COMPOUNDS 353

PURIFICATION OF INORGANIC AND METAL ORGANIC CHEMICALS(Including Organic compounds of B, Bi, P, Se, Si, and ammonium andmetal salts of organic acids)

INTRODUCTION 445INORGANIC COMPOUNDS 446METAL-ORGANIC COMPOUNDS 505

PURIFICATION OF BIOCHEMICALS AND RELATED PRODUCTS

INTRODUCTION 577AMINO ACIDS and PEPTIDES 583PROTEINS, ENZYMES, DNA and RNA 607CAROTENOIDS 625CARBOHyDRATES 631STEROIDS 650

MISCELLANEOUS COMPOUNDS (including biologically useful reagents,Low-molecular-weight bioactive substances, antibiotics, coenzymes, vitamins ,lipids, phospholipids, nucleosides, nucleotides and polynucleotides) 662