Fundamental processes of dye chemistry. 1949

474	SUBJECT INDEX

Malachite, green, 300 Manganese dioxide, 9

Manganous-manganic oxide, 9, 303 Martius yellow, 151

Meldola blue, 9, 310 Melting point

apparatus, 43-46 block, 45 definitoin, 46 determination, 41

Mercuric oxide as sulfonation catalyst, 56, 230, 234

Metachrome brown, 153 Metal containers, 16 Metanilic acid, 120

Methane base, see Tetramethyl- p,p'-diaminodiphenylmethane

1-Methoxyanthraquinone, 234

1-Methylaminoanthraquinone, 233 /3-Methylanthraquinone, 223, 227 Methylene blue, 311

titration with TiCk, 393 Methylene green, 313

Michler's hydrol, see Tetramethyl- p,p'-diaminobenzohydrol Michler's ketone, see Tetramethyl- p,p'-diaminobenzophenone

Mikado orange R, 297 Mirbane, oil of, 160 Mixed acid, 69

Mixed melting point, 46 Mixing, 5

Modern violet, 310 Monastral fast blue BS, 338 Monoethylaniline, 134

physical properties, 135, 136

N

Naphthamine yellow NN, 335 Naphthalene, 1, 53

catalytic oxidation, 171 Naphthalene-1,5-disulfonic acid,

219 Naphthalene-2,7-disulfonic acid,

209, 308 Naphthalene-3,6-disulfonic acid,

209

Naphthalene green V, 308

Naphthalene-a-sulfonic acid, 214 nitration, 215

Naphthalene-^-sulfonic acid, 184 187

nitration, 184

solubility of sodium salt, 189 Naphthalenesulfonic acids, 53,

183 ff. nitration, 54

Naphthalene-l,4,5,8-tetracar- boxylic acid, 221

Naphthalene-1,3,5,7-tetrasulfonic acid, 55, 211

Naphthalene-l,3,6-trisulfonic acid,

211

Naphthazarin, 122 Naphthionic acid, 180, 293 Naphthogene blue RR, 220 a-Naphthol, 180

determination, 388 /3-Naphthol, 188

determination, 365 sulfonation, 191

technical observations, 190 Naphthol AS-ITR, 98 Naphthol blue black B, 289

l-Naphthol-3,8-disulfonic acid, 220 2-Naphthol-3,6-disulfonic acid, 192,

194, 197 determination, 390

2-Naphthol-6,8-disulfonic acid, 192, 194, 197, 208

Naphthol pitch, 344 l-Naphthol-4-sulfonic acid, 182

determination, 390 2-Naphthol-l-sulfonic acid, 84, 199 2-Naphthol-6-sulfonic acid, 192,

193,194,197, 391 2-Naphthol-3,6,8-trisulfonic acid,

192

Naphthol yellow S, 151 Naphthsultone, 187, 217 a-Naphthylamine, 176

diazotization, 245, 260 technical observations, 178

^-Naphthylamine, 54, 203 diazotization, 246

Naphthylamine black D, 277 l-Naphthylamine-2,4-disulfonic

acid, 80, 85, 178

SUBJECT INDEX

475

l-Naphthylamine-3,6-disulfonic acid, 209, 277

l-Naphthylamine-3,8-disulfonic acid, 219, 220

l-Naphthylamine-4,8-disulfonic acid, 219, 220

2-Naphthylamine-4,8-disulfonic acid, 122, 219, 408 2-Naphthylamine-5,7-disulfonic

acid, 205

determination in presence of 2,6,8-isomer, 391

2-Naphthylamine-6,8-disulf onic acid, 205

determination in presence of 2,5,7-isomer, 391

l-Naphthylamine-5-sulfonic acid, 214

l-Naphthylamine-6-sulfonic acid, 184

l-Naphthylamine-7-sulfonic acid,

184, 280 l-Naphthylamine-8-sulfonic acid,

214

2-Naphthylamine-l-sulfonic acid, 4,

200 l-Naphthylamine-3,6,8-trisulfonic

acid, 211 2-Naphthylamine-l,5,7-trisulfonic

acid, 205 Neoprene, 368 Nerol dyes, 100

Nevile-Winther acid, see l-Naphthol-4-sulfonic acid

Nickel, 364 Nitrating acid, 69 Nitration

general, 6, 69 kettle, 69, 71, 101

of primary aromatic amines, 166 Nitric acid as oxidizing agent, 9 Nitrite solution, 1 N, 240, 385 2-Nitro-4-acetaminotoluene, 52 3-Nitro-4-acetaminotoluene, 52 p-Nitroacetanilide, 131

Nitro acid III, see 4-Nitro-2-amino- phenol-6-sulfonic acid

4-Nitro-2-aminophenol, 102, 115 4-Nitro-2-aminophenol-6-sulfonic

acid, 122

2-Nitro-4-aminotoluene, 52, 165 o-Nitroaniline, 8, 92

diazotization, 246 uses, 93

m-Nitroaniline, 80, 113 p-Nitroaniline, 8, 92, 107, 132

diazotization, 246, 260 technical observations, 93 uses, 93

o-Nitroaniline-p-sulfonic acid, 107 p-Nitroaniline-o-sulfonic acid, 93,

99

o-Nitroanisole, 93, 97, 107, 148 p-Nitroanisole, 148 1-Nitroanthraquinone, 58 4-Nitroanthraquinonyloxamic acid,

232

Nitrobenzene, 66, 68, 72 chlorination, 117 technical observations, 69 toxicity, 76

Nitrobenzene-2,5-disulfonic acid,

106

o-Nitrobenzenesulfonic acid, 85,122 m-Nitrobenzenesulfonic acid, 58,

120

technical observations, 122 Nitrochloro-, see also Chloronitro- 2-Nitro-4-chloroaniline, 109

diazotization, 247 o-Nitrochlorobenzene, 90, 107, 109 m-Nitrochlorobenzene, 116 p-Nitrochlorobenzene, 90 Nitrochlorobenzenes

physical properties, 91 separation of o- and p- isomers, 90

2-Nitrochlorobenzene-4-sulfonic acid, 70, 85, 104, 107

4-Nitrochlorobenzene-2-sulfonic acid, 99

2-Nitro-4-chlorotoluene, 52,160,

164

2-Nitro-6-chlorotoluene, 52,160,

164 Nitro-p-dichlorobenzene, 93,108 l-Nitro-2,4-dimethoxy-5-chloro-

benzene, 98 Nitro filters, 368

Nitroformanilides, o- and p-, 133 Nitro group, lability, 101

476	SUBJECT INDEX

Nitrometer, Lunge, 72 l-Nitro-2-methylanthraquinone,

227

1-Nitronaphthalene, 80, 175 technical observations, 178

l-Nitronaphthalene-3,8-disulfonic acid, 219

l-Nitronaphthalene-4,8-disulfonic acid, 219

2-Nitronaphthalene-4,8-disulfonic acid, 122, 219

l-Nitronaphthalene-5-sulfonic acid, 215

l-Nitronaphthalene-6-sulfonic acid, 184

l-Nitronaphthalene-7-sulfonic acid, 184

l-Nitronaphthalene-8-sulfonic acid, 215

l-Nitronaphthalene-3,6,8-trisulfonic acid, 211

o-Nitrophenol, 147 p-Nitrophenol, 147 2-Nitrophenol-4,6-disulfonic acid,

153

Nitrophenols, alkylation, 148 o-Nitrophenol-p-sulfonic acid, 107 p-Nitrophenyloxamic acid, 93 o-Nitrophenylhydrazine, 97 p-Nitrophenylhydrazine, 95 Nitrophenylpyrazolones, 97 Nitrosobenzene, 78 p-Nitrosodiethylaniline, 309 p-Nitrosodimethylaniline, 308, 311

reduction, 78, 312 Nitroso-£-naphthol, 80, 201 p-Nitrosophenol, 85 Nitrosylsulfuric acid, 9, 247 o-Nitrotoluene, 53, 160 m-Nitrotoluene, 51 Nitrotoluenes, 3 3-Nitro-4-toluidine, diazotization,

246 l-Nitro-2,4,5-trichlorobenzene, 98

O acid, see o-Carboxyphenylthio- glycolic acid

Oleum, 70, 82

Orange II, 262, 378 Orange IV, 273 Orientation rules, 50 ff.

anthraquinone series, 56 benzene series, 51 carbazole series, 60 naphthalene series, 53

Orienting power, 51 Orthanilic acid, 122 Oxazine dyes, 308 ff. Oxidation methods, 8

Package store, 378

Palatine chrome black 6B, 202 Para red, 93

Partial condensers, 24, 341 Partial reduction, 79, 113 Patent blues, 301 Permanent red 2G, 267 Phenanthrene, 1

Phenol, 51, 86

from chlorobenzene, 76, 88 technical observations, 86

Phenolphthalein paper, 395 Phenols, separation, 30 Phenol-o-sulfonic acid, 51 Phenol-m-sulfonic acid, 144, 145 l-Phenylaminonaphthalene-8-

sulfonic acid, 217, 218 2-Phenylamino-5-naphthol-7-

sulfonic acid, 281 2-Phenylamino-8-naphthol-6- sulfonic acid, 209

Phenylazodinitrodiphenylamine,

272

Phenyldiazonium solution, 0.1 N, 395

ra-Phenylenediamine, 112,115 p-Phenylenediamine, 93, 133 m-Phenylenediaminesulfonic acid,

103 p-Phenylenediaminesulfonic acid,

99

monobenzoyl derivative, 99 Phenyl-gamma acid, see 2-Phenyl- amino-8-naphthol-6-sulfonic

acid

SUBJECT INDEX

477

Phenylglycine, 90 Phenylglycine-o-carboxylic acid, 90,

323 Phenylhydrazine, 80

Phenylhydrazine-p-sulfonic acid, 128

Phenylhydroxylamine, 78 rearrangement, 78

Phenyl-J acid, see 2-Phenylamino- 5-naphthol-7-sulfonic acid

l-Phenyl-3-methyl-5-pyrazolone, 129

Phenyl-a-naphthylamine, 179 Phosgene, 139

Phosphorus, 66 Phosphorus chloride, 66

Phthalic anhydride, 58,171, 225, 227

Phthalimide, 173 Phthalocyanine dyes, 338 Picramic acid, 152

Picric acid, 102, 150 Pigment colors, 109 Polar brilliant red 3B absorption, 407

analysis, 404 Polar yellow 5G, 266

Polyazo dyes, 95, 277 ff., 282 Polychlorobenzenes, 62, 65 Polyphenyl yellow 3G, 297 Polyvinyl chloride, 368 Poma-Cesano-Maderno process, 65 Porcelain, 367

Precipitates, washing, 20 Precipitation, fractional, 38 Presses, 20

Pressure vessels, general rules on use, 361

Primuline, 4, 332 Primuline base, 332

Primuline fusion, separation of melt, 334

Primuline red, 334 Proportions, 13 Purity

control, 49

of starting materials, 11-13 Purification of products, 34 Pyramidone, 129 Pyranthrone, 223

Pyrazolone dyes, 265

Pyrene, 1, 221

Pyrenequinone, 222

Pyrex glass, 16, 366

Pyridine, 1, 251

Pyrolusite, 58

Quartz, 367

Quinizarin, 58, 237, 318 Quinizarin green, 317 Quinoline, 1

synthesis, 69 Quinoneoxime, 85

R

R acid (R salt), see 2-Naphthol- 3,6-disulfonic acid

Raschig rings, 24, 88, 151, 341 Reaction kettles, 316

Reaction products, separation, 27 Reaction tables, 5

Recipes, 4 Recrystallization, 35 Rectification, 23 Reduction

apparatus, 94 electrolytic, 80 general, 7, 77 kettles, 77, 94, 96 partial, 79, 113

Reductions with sodium sulfide, equations, 114

Reductive splitting of azo dyes, 402 Repair shops, 371

Reprecipitation, 37 Reservoirs, acid resistant, 366 Resorcinol, 144

Rubber, 368 hard, 368

S

Saccharin, 83

S acid, see l-Amino-8-naphthol-4- sulfonic acid

Salicine black U, 202 Salicylic acid, 154

technical observations, 155

478	SUBJECT INDEX

Salting out, 39 Sample dyeing, 375

Sandmeyer reaction, 9, 67,161, 163 Schaeffer acid (and salt), see 2- Naphthol-6-sulfonic acid

Schultz dye tables, 399 Screw press, 20, 107

Separation of reaction products, 27 Silver salt, see Anthraquinone-2-

sulfonic acid

Sirius light blue G, 107, 279 Sodium amide, 90, 324

Sodium hydrosulfide, 79, 113, 114, 320

Sodium hydrosulfite, 80, 157, 321, 402, 404

Sodium hypochlorite, 9,145,167 Sodium 0-naphtholate, 54

Sodium sulfide, 79, 228, 237, 321, 330

Solvent of crystallization, 42 Solvents

distilling off, 21

for recrystallization, 35 Spiral gas washing bottle, 62 Spot test reagents, 396

SS acid (Chicago acid), see 1- Amino-8-naphthol-2,4- disulfonic acid

Standardization of product, 377 Standard titrimetric materials, 384 Stannous chloride, 80, 402, 404,

407

Starch-iodide paper, 395 Steam

consumption, 372 distillation, 26 superheater, 26 trap, 26

Steel, 364

Stirrers, 16, 17, 366 Stirring, 15

Stone filter funnel, 150 Stoneware, 365

Substituents, classification, 50 Suction filter, 19

Sulfanilic acid, 126, 262 diazotization, 248,261 pure for analysis, 384

Sulfides as reducing agents, 76, 79, 113

Sulfite, removal, 58 Sulfo chrysoidine, 287

Sulfo groups, indirect introduction, 85

cD-Sulfomethyl group, introduction, 85, 250

Sulfon acid blue R, 218 Sulfonation

general, 6, 82 vessels, 101, 105

Sulfone reagent, 185, 211, 243 Sulfones, 85

Sulfonic acids rearrangement, 82 separation, 31

l-p-Sulfophenyl-3-methyl-5- pyrazolone, 129

Sulfoxylate, 80

Sulfur black T, 102, 337 Sulfur fusions, 332

Sulfuric acid, heat capacity, 70 Sulfuryl chloride, 67, 145 Sun yellow G, 296 Superheater, 142

Temperature-pressure curves for aqueous ammonia, 90

for aqueous sodium hydroxide, 89 Test dyeing, 48

Testing for purity, 40 Test papers, 395 Tetrachloroethane, 66

3,5,8,10-Tetrachloropyrene, 221 Tetraethyl-p,p'-diaminobenzo-

hydrol, 308 Tetraethyl-p,p'-diaminobenzo-

phenone, 140

Tetramethyl-p,p'-diaminobenzo- hydrol, 138, 307

Tetramethyl-p,p'-diaminobenzo- phenone, 139, 298, 306 Tetramethyl-p,p'-diaminodiphenyl-

methane, 137 Thermometer corrections, 40

SUBJECT INDEX

479

Thermometers, recording type, 88 Thiazine blue, 314

Thiazine dyes, 308 Thiazole paper, 395 Thiazole yellow, 335, 336

Thiele melting point apparatus, 44 Thioamide, 325, 327 Thiocarbanilide, 76, 326 Thiocyanates in coupling reactions,

250

Thioflavine T and S, 335 Thioindigo, 330 a-Thiosatin, 326, 329 Thionine blue, 314

Thiooxamidodiphenylamidine, 325,

327

Thiosalicylic acid, 330 Thiosulfate in coupling reactions,

250 Thio-p-toluidine, 332 Tin, 80, 364

Titanium trichloride solution, 393 Tobias acid, see 2-Naphthylamine-

1-sulfonic acid o-Tolidine, tetrazotization, 261

o-Tolidine-o-cresotinic acid intermediate, 285

Toluene, 1, 51 Toluenedisulfonic acid, 302 p-Toluenesulfanilides, 53, 250 p-Toluenesulfonethylanilide, 134 o-Toluenesulfonyl chloride, 84

p-Toluenesulfonyl chloride, 67, 84, 134, 304

p-Toluidine, 52 nitration, 70, 165

1,2,4-Toluylenediamine, 116 p-Tolyhydroxylaminesulfonic acid,

118

Trichlorobenzene, 66

Trinitrophenol, 150 Triphenylmethane dyes, 298 ff.

titration with TiCk, 394 Trisazo dyes, 279, 281 Tropaeoline, 273

U

Ultraviolet light, 158

Vacuum, 373 distillation, 341 ff. pumps, 344

Vanadium oxide, 8 Vats, 367 Vesuvine R, 282

Vicinal derivatives, 53 Victoria blue B, 140, 306

Victoria pure blue BO, 140, 307 Volumetric analysis of dyes,

Knecht method, 392 Vulcanization accelerators, 76

W

Washing precipitates, 19 Wave-breaker, 17 Weighing, 13

Weiler-Ter Meer process, 75 Weldon mud, 9, 303 Wood, 367

Wool, 368

Wool blue 5B, 305 Wool fast blue BL, 220 Wool green S, 307 Work bench, 11 Wrought iron, 364

scrap, 77, 79, 212

Xylene, 1

Xylene blue VS, 301 Xylene yellow, 266 m-Xylidinesulfonic acid, 84

Yields, 10

Zambesi black V, 187 Zinc, 364

Zinc dust, 80, 123, 125, 402 evaluation, 396

Zincke thermometers, 43