A
Acetforaldehyde, properties of, 371 Acetf orate, sodium, decarboxylation of,
386, 387 Acetforic acid,
conductivities in, 358 dielectric constant of, 385 physical properties of, 386 preparation of, 383, 384 Acetforic carboxy fluoride, 390 Acetforyl anhydride, 390
Acetforyl fluoride, analysis of, 158 Acetforyl iodide, pyrolysis of, 367 Acetonitrile, fluorination of, 342 Acetyl fluoride,
analysis of fluorine in, 83 fluorination of, 342 Acforylation, 399
Acid fluorides, analysis of fluorine in, 83 Acrylic acid, methforyl containing, 265 Acrylic acid and derivatives, fluorine con
taining, 264, 265
Adrenergic blocking agents containing fluorine, 257
Air,
analysis of fluorine compounds in, 176 of fluorine in, 172, 176
of fluorocarbons in, 176 of hydrogen fluoride in, 176 Alcoholic beverages, tests for fluoride in,
94
Alcohols, fluorine containing, 229-232 Aldehydes,
containing methforyl group, 236 fluorine containing, 235, 236
Aliphatic aldehydes, fluorine containing, 235, 236
Aliphatic fluorides made from aliphatic halides, 218, 219
Aliphatic halides, reagent for aliphatic fluorides, 218, 219
Aliphatic organic compounds containing fluorine, 214-220
Alkforyl aromatic compounds, 399-403 Alkforyl arsenic compounds, 324, 325 Alkforyl cadmium compounds, 328 Alkforyl iodides, 321, 323
Alkforyl magnesium compounds, 327, 328 Alkforyl mercurials, 321, 322, 323 Alkforyl metallic compounds, 321-328 Alkforyl monoiodides, properties of, 368 Alkforyl phosphorus compounds, 323, 324 Alkforyl sulfur compounds, 326, 327 Alkforyl zinc compounds, 328 Alkyl arsenic fluorides, 330 Alkyl boron fluorides, 328 Alkyl fluorides,
analysis of fluorine in, 83
decomposition by oxidation, 76, 77 Alkyl germanium fluorides, 329 Alkyl lead fluorides, 330 Alkyl metal fluorides, 328-331 Alkyl phosphorus fluorides, 330 Alkyl selenium fluorides, 331 Alkyl silicon fluorides, 329 Alkyl sulfur fluorides, 331 Alkyl tellurium fluorides, 331 Alkyl thallium fluorides, 329 Alkyl tin fluorides, 330
Alpha fluoro-carboxylic acids, 239 Aluminum compounds, analysis of fluo
rine in, 177
Aluminum fluorides, X-ray patterns of, 160
Amides, fluorine containing, 240, 241 Amines,
fluorination of, 344
fluorine containing, 242, 243
Amino acids, fluorine containing, 246, 247, 248
Amperometric titration, 132, 133 Analytical chemistry of fluorine,
introduction, 53 reviews of, 54
Anilines, fluorination of, 344
Animal matter, analysis of fluorine in, 151 Animals, analysis of fluorine in, 173 Antibiotics, fluorine containing, 257, 258 Antimalarial drugs, fluorine containing,
253, 254, 255
Antimony, fluorocarbon compounds of, 399
Antiseptics, fluorine containing, 256 Apatites, analysis of fluorine in, 117, 175 Arc, alternating current, 154
direct current, 152, 153, 154
Aromatic aldehydes, fluorine containing, 235
Aromatic compounds,
analysis of fluorine in, 80, 83 fluorination of, 342
fluorine in ring, 223, 224
Aromatic compounds with fluorine con
taining side chain, 220-223 Aromatic fluorides,
analysis of, 164 decomposition by,
alkali metals, 79 alkaline fusion, 81 preparation, 223, 224
Aromatic fluorine compounds, difficulties of analysis, 75
Arsenic, alkforyl compounds of, 369 Arsenic fluoride,
analysis of, 158 microwave, 162 Aryl arsenic fluorides, 330 Aryl boron fluorides, 328 Aryl germanium compounds, 329 Aryl lead fluorides, 330
Aryl mercury fluorides, 328 Aryl metal fluorides, 328-331 Aryl phosphorus fluorides, 330 Aryl selenium compounds, 331 Aryl silicon fluorides, 329 Aryl tellurium fluorides, 331 Aryl thallium fluorides, 329 Aryl tin fluorides, 330
Aspirin, fluorine containing, 258 Auric fluoride, 4
Â
Bactericides, fluorine containing, 254, 256, 258
Baking powder, analysis of fluorine in, 68, 174
Bauxite, analysis of fluorine in, 175 Benzoyl fluoride, analysis of, 164 Beryllium compounds, analysis of fluorine
in, 177
Beryllium fluoride, analysis of fluorine in, 72
Beta fluoro-carboxylic acids, 239 Beverages, analysis of fluorine in, 174 Biological material, analysis of fluorine in,
68
Biological samples, analysis of fluorine in, 69, 71, 172, 173, 174
Blood, analysis of fluorine in, 68, 70, 86, 87, 173
Body fluids,
analysis of fluorine in, 173 tests for fluoride in, 94 Bone,
analysis of fluorine in, 69, 70, 71, 153, 173
tests for fluoride in, 99
Borates, analysis of fluorine in, 86, 177 Boron trifluoride,
analysis of, 57, 128, 158 of fluorine in, 177 of impurities in, 157 tests for, 102
Borosilicates, analysis of fluorine in, 72 Bromination of hydrofluorocarbons, 220 Bromine fluorides, 41, 42
analysis of, 158
Bromine monofluoride, 41, 42 physical properties of, 42 Bromine pentafluoride, 42 Bromine trifluoride,
acids in, 45 bases in, 44
chemical reactions in, 45, 46, 47 conductivity of, 44
ions in, 44
neutralization reactions in, 45 physical properties of, 42 reaction with carbon halides, 364 use in preparing complex fluorides, 45,
46, 47
Bromofluorides, 45, 46, 47
Butadienes, fluorine containing, 270 Butforaldehyde, properties of, 372
Butforane-butane, binary system, 356 Butforane, cyclo, binary mixtures of, 363
physical properties of, 348 Butforanes, analysis of, 158, 159 Butforene, cyclo, reactions of, 377, 378,
379, 380
Butforenes, comparison of reactivities, 377, 378
Butforyl, 1,1-dihydroalcohol, 393 Butforyne-2, 381
microwave study, 381 reactions of, 381
Butter, analysis of fluorine in, 174 Butyrforates, η-butyl, s-butyl and t-
butyl, hydrolysis of, 395 Butyrforic acid, 385
physical properties of, 386 properties of salts of. 387
C Calcium fluoride,
analysis for, 154 of fluorine in, 145 Carbon,
fluorination of, 345
reaction with chlorine trifluoride, 345 Carbon dioxide, determination of, in cell
gases, 62
Carbon monoxide, determination of, in cell gases, 64
Carbonates, analysis of fluorine in, 151 Catalytic activity, 157
Cathode, hollow, 154
Cell gases, molecular weight, determina
tion of, 65, 66
Chemical properties of fluorocarbons, 347-364
Chiolite, 9, 10
Chlorination of hydrofluorocarbons, 220 Chlorine, solubility in fluorocarbons, 354 Chlorine fluorides, 39, 40, 41
analysis of, 158, 159 Chlorine monofluoride,
physical properties of, 39, 40, 41 thermodynamic functions of, 40 Chlorine trifluoride,
acids and bases in, 48 conductivity of, 44 properties of, 41
reaction with carbon, 345
Chlorocyclohexforane, chemical reactions of, 366
Chloroethforylene, polymers, of, 260
thermodynamic properties of, 363 Chlorofluoroethylene, polymers, of, 266,
267
Chlorotrifluoroethylene, polymers, of, 267, 268, 269
Coal, analysis of fluorine in, 72, 175 Cobalt fluorides, heats of fluorination of,
345
Colorimetric methods, 134-149 Complex fluorides, 1
analysis of fluorine in, 89 of alkali metals, 2 of alkaline earth metals, 5 of aluminum, 9, 134, 135, 139, 140 of antimony, 19, 20
of arsenic, 19
of beryllium, 4, 136, 138, 139, 140 of bismuth, 20
of boron, 6 of bromine, 28 of cadmium, 5 of carbon, 12
of cerium, 12, 17, 139, 140 of chlorine, 28
of chromium, 24 of cobalt, 30 of columbium, 21, 22 of copper, 3
of gallium, 10 of germanium, 13 of gold, 4 of group I, 2 of group II, 4 of group III, 6 of group IV, 12 of group V, 17 of group VI, 22 of group VII, 28 of group VIII, 29 of hafnium, 15, 16 of indium, 10 of iodine, 28 of iridium, 32
of iron, 29, 30, 134, 135, 138, 139, 140 of lanthanum, 11, 17
of lead, 14 of magnesium, 5 of manganese, 28, 29 of mercury, 6 of molybdenum, 25 of neptunium, 17, 27 of nickel, 30, 31 of nitrogen, 17 of osmium, 32 of oxygen, 22 of palladium, 32
of phosphorus, 2, 17, 18, 19 of platinum, 31, 32, 33 of platinum metals, 31 of plutonium, 17, 27, 28 of protactinium, 22 of rare earth elements, 11 of rhenium, 29
of rhodium, 31 of ruthenium, 31 of scandium, 11 of selenium, 24 of silicon, 2, 12 of silver, 3
of sulfur, 2, 22, 23, 24 of tantalum, 21, 22 of tellurium, 24 of thallium, 10
of thorium, 16, 17, 134, 138, 139, 140 of tin, 14
of titanium, 15
of transuranium elements, 27 of tungsten, 26
of uranium, 11, 17, 26, 27 of vanadium, 20
of yttrium, 11 of zinc, 5
of zirconium, 15, 16, 134, 139, 140 Conductometric titration, 131, 132 Corn, analysis of fluorine in, 69
Cottonseed meal, analysis of fluorine in, 69
Cryolite, 9
analysis of fluorine in, 72, 84, 175 Cryolithionite, 2
Cyclobutane derivatives, fluorine con
taining, 226-229
Cyclobutane rings, formation, 226 Cyclohexforane,
carboxylic acid, 388
x-ray pattern, 160
Cyclohexforyl nitrogen difluoride, 392 Cyclopentforane, energy of vaporization,
theoretical calculations, 362 D
Decforanes, analysis of, 158 Delta fluoro-carboxylic acids, 240 Dibutforyl oxide, 339
solubilities in, 355
Dielectric constants, 162, 167 Diethforyl mercury, 323 Difluoroacetic aηid, 239
Difluorochloromethane, determination of, 59
Difluorodichloromethane, determination of, 58, 59
Difluorophosphates, 18 Difluorophosphoric acid, 18
Diketone fluorides, analysis of fluorine in, 83
Dimethforyl acetylene, 226 Dimethforyl iodophosphorus, 323 Dimethforyl mercury, 322
Dimethforylcyclohexforane, solubility of nitrogen in, 354
Dipole moments, 162 Discharge, electrodeless, 154 Drugs, fluorine containing, 253-258 Dyes, fluorine containing, 248-253
Ε
Eggs, analysis of fluorine in, 71 Elastomers,
fluorine containing, 261 fluorocarbon, 404
Electrochemical process, 340, 341 commercial plant, 340 products of, 341
starting materials for, 341 Electrodialysis, 162
Electrolytic cell gases, analysis of, 61-67 Electron diffraction, 161
Enamels, analysis of fluorine in, 176 Energy of formation of K F2, 3
Energy of vaporization of fluorocarbons, 357, 358
Enzymatic activity inhibition, 155
Esters, fluorine containing, 240 Ethers,
fluorine containing, 232-235 fluorocarbon groups containing, 397 Ethforanes, analysis of, 158
Ethforyl iodide, absorption spectra and photochemical decomposition, 368 Ethforylene,
poly, crystal properties of, 363 polymers of, 260
reactions of, 227, 383 reactions with,
alcohols, 394
fluorocarbon iodides, 367, 368 Ethforylene diiodide, reaction with eth
forylene, 367
Ethforylenes, analysis of, 158 Exchange reactions, 162
for fluorocarbon production, 346 F
Fertilizers, analysis of fluorine in, 173, 174 Fibers, fluorocarbon, 404
Fire extinguishers, fluorocarbon bromides as, 366
Fish, analysis of fluorine in, 174 Flours, analysis of fluorine in, 69 Fluoral, 236
Fluoride,
apparatus used for isolation by volatil
ization, 88
distillation as fluorosilicic acid, 83-89 evolution as hydrofluoric acid, 89, 90 isolation by pyrolydrolysis, 89 isolation by volatilization, 83-92
miscellaneous methods, 90
Fluoride complexes, equilibrium con
stants for, 140 Fuoride ion,
analysis of, 162
bleaching of lakes, tests for, 94, 95, 96 color and fluorescence, tests for, 96, 97 colorimetric methods, references for,
143, 144 determination as
calcium fluoride, 104-108 lead chlorofluoride, 102, 103, 104 rare earth metal or other metals
fluorides, 108, 109
determination of, 102-157 by catalytic activity, 157
by cerium and rare earth titrations, 119, 120
by electrometric methods, 128-134 amperometric titration, 132, 133 conductometric titration, 131, 132 high frequency oscillator titration,
133, 134 polarography, 134
potentiometric titration, 128-131 by enzymatic activity inhibition,
155, 156
by etching and wettability of glass, 156
by iron and aluminum titrations, 118, 119
by lead chlorofluoride and calcium fluoride titrations, 121, 122 by miscellaneous gravimetric meth
ods 109, 110
by neutralization titrimetric meth
ods, 123-128 miscellaneous, 127, 128
reactions involving fluorosilicic acid and potassium fluoro
silicate, 123-127
by photometric methods, 134-155 colorimetric bleaching, 134-147 chemistry of fluoride complexes,
134-140
colorimetric methods using aluminum, 147
ferric ion, 145, 146, 147 titanium, 141, 142 zirconium, 142-145
emission spectroscopy, 152-155 A.C. arc, 154
D.C. arc, 152, 153, 154 electrodeless discharge, 154 hollow cathode discharge tube,
154
indirect determinations, 155 fluorometric methods, 149, 150 methods using
molybdenum, 149 thorium, 147, 148, 149 miscellaneous colorimetric meth
ods. 147, 148, 149
555
nephelometric methods, 150, 151, 152
redox methods, 149
by precipitation of calcium fluoride, titrations, 122, 123
by thorium titrations, 110-117 effect of pH on, 111, 112, 113 indicators for, 115
indicators, optimum concentra
tions, pH, etc., 113 interfering substances, 117 miscellaneous experimental con
ditions for, 116
nature of the medium for, 114, 115 standardization of solution, 113 by titrimetric methods, 110-123 by zirconium titrations, 117 effect on iron redox potential, 137 etching and drop tests for, 92, 93, 94 gravimetric determination, 102-110 heating temperatures for precipitates in
gravimetric determination, 106 microscopic tests, 98, 99
miscellaneous tests for, 99, 100 precipitation of, 102-110 precipitation tests, 97, 98 qualitative tests for, 92-100
recovery form organic compounds, 53 separation and isolation of, 67-90 traces of, comparison of fluorometric
methods, 151 Fluorides,
complex (see Complex fluorides) higher of alkali metals, 2
insoluble qualitative analysis of, 91 Fluorination,
catalytic, 342, 343, 344 liquid phase, 345
metallic fluoride process, 344, 345 Fluorine,
qualitative analysis, reviews of, 91 qualitative detection and identification
of, 90-102
separation from other elements, 53 Fluorine compounds,
analysis of,
by infrared absorption, 157, 158, 159, 168
by measurement of physical proper
ties, 161, 162, 163
by Raman scattering, 157, 158, 159 by spectroscopic methods, 157-160 by ultraviolet absorption, 159, 160 by x-ray diffraction patterns, 160,
161
Fluorine compounds in water, conversion to fluoride ion, 82
Fluorine containing, complex salts and acids, 1 compounds, x-ray patterns, 160 olefins, polymerization of, 403 organic compounds, table of, 271-307 Fluorine gas, elementary analysis of, 59,
60, 61
Fluorine (elementary) in gaseous samples, determination of, 55, 56
Fluorine loss through volatilization, 54 Fluorite, analysis of fluorine in, 72, 84,
175
Fluoroacetates, analysis of fluorine in, 78 Fluoroacetic acid, 238
analysis of, 128 Fluoroacetyl sugars,
analysis of, 164
analysis of fluorine in, 80 Fluoroacridines, 245, 254, 256 Fluoroaluminate
of barium, 9 of potassium, 9, 10 of sodium, 9, 10 of strontium, 9 of thallium, 9, 10 Fluoroaluminates, 9, 10
crystal chemistry of, 9 Fluoroantimonates, 19, 20 Fluoroarsenates, 19 Fluoroaurates, 4
Fluorobenzamide, analysis of fluorine in, 80
Fiuorobenzene, analysis of fluorine in, 76, 79, 80
Fluorobenzenes, analysis of, 159
Fluorobenzoic acid, analysis of fluorine in, 80
Fluoroberyllates, 4 Fluorobismuthates, 20 Fluoroborate,
of aluminum, 8 of ammonium, 7, 8 of barium, 8
of calcium, 8 of cobalt, 8 of magnesium, 8 of nitronium, 8 of nitrosyl, 8 of potassium, 7 of silver, 8 of sodium, 7 of strontium, 8 of thallium, 8 of zinc, 8
Fluoroborate ion, decomposition in water, 7
Fluoroborates, 6 analysis of, 158
analysis of fluorine in, 89, 110, 177 aromatic, 223, 224
determination of fluorine in, 107 organic, 9
tests for, 99
tests for fluoride in, 94 Fluoroboric acid, 6, 7
Fluorobutadienes, polymers of, 270 Fluorocarbon,
antimony derivatives, 326, 399 arsenic derivatives, 324, 325, 326 cadmium derivatives, 328 inert, uses of, 349
magnesium derivatives, 327, 328 metal derivatives, 321-328 phosphorus derivatives, 323, 324 resistance to reaction, 336 selenium derivatives, 327, 399 silicon derivatives, 328
sulfur derivatives, 326, 327, 342 zinc derivatives, 328
Fluorocarbon acid fluorides, production of, 341
Fluorocarbon acid halides, infrared spec
tra of, 454
Fluorocarbon alcohols, 393, 394 Fluorocarbon aldehydes, 371, 372
infrared spectra of, 454 preparation of, 371
Fluorocarbon amides, infrared spectra of, 456
Fluorocarbon amines, 391 Fluorocarbon analysis, 67
Fluorocarbon aromatic ketones, 372, 373 Fluorocarbon beta diketones, 374, 375
Fluorocarbon bromides, 364, 365, 366 use as fire extinguishers, 366
Fluorocarbon carboxylic acid salts, de
carboxylation of, 387
Fluorocarbon carboxylic acids, 338, 3 8 3 - 391
aliphatic esters of, 394, 395 aromatic esters of, 395
containing hydrogen on terminal car
bon atom, 384, 385
decarboxylation of silver salt, 367 infrared spectra of, 455
methyl ortho esters of, 395, 396 peroxides, 390
pyrolysis of ammonium salts, 388 of salts of, 388
reaction of silver salts with halogens, 390
reactions of silver salts, 388 reduction of, 394
reduction to aldehydes, 371
use of separation of aromatic and paraflinic hydrocarbons, 391 vinyl esters of, 396
Fluorocarbon chemistry, 333-448 Fluorocarbon chlorides, 337, 364, 365, 366
pyrolysis and reduction of, 366 Fluorocarbon chlorides and bromides,
chemical reactions of, 366
Fluorocarbon derivatives, 337, 338, 3 6 4 - 404
effect of surface tension of water, 351 exchange reaction for, 346
physical properties of, 404
Fluorocarbon 1,1-dihydroalcohols, 393, 394
Fluorocarbon 1,1-dihydroamines, 391 Fluorocarbon 1,1-dihydroisocyanates, 391 Fluorocarbon elastomers, 404
Fluorocarbon esters, 394, 395, 396 infrared spectra of, 455 Fluorocarbon fibers, 404 Fluorocarbon halides,
infrared spectra of, 458 magnetic susceptibilities of, 366 Fluorocarbon hydrides, 337
infrared spectra of, 452 production of, 341
Fluorocarbon-hydrocarbons, deviations from Raouit's law, 339
Fluorocarbon iodides, 366-371 by replacement reactions, 368 chlorination and bromination of, 368 methods of preparation, 367
photochemical bromination or chlori
nation of, 365
reaction to form Grignard reagent, 369 with ethylene, 368
with mercury, 369
Fluorocarbon isocyanates, 392, 393 Fluorocarbon ketones, 372-375
infrared spectra of, 454
produced by catalytic fluorination, 372 by oxidation, 372
production of, 342
Fluorocarbon mercurials, 321, 322, 323 Fluorocarbon nitrides, 337, 339
production of, 341 properties of, 392
Fluorocarbon nitrides and other nitrogen- containing compounds, 391, 392, 393 Fluorocarbon nitriles, infrared spectra of,
453
Fluorocarbon nitro compounds, 391, 392 Fluorocarbon nomenclature, 334, 335 Fluorocarbon olefins, 375-383
addition of basic reagents to, 376 by pryolysis of fluorocarbon salt, 375,
376
by thermal reactions, 375
containing the terminal methforylene group, 382, 383
free radical additions to, 383 physical properties of, 376 Fluorocarbon oxides, 337, 339, 396
viscosity of, 352
Fluorocarbon oxides and ethers contain
ing fluorocarbon groups, 396, 397, 398
Fluorocarbon plastics, 404
Fluorocarbon polymerization, 403, 404 Fluorocarbon polymers, 403, 404
Fluorocarbon reactions, exchange of fluorine for other halogen, 346 Fluorocarbon rubbers, 404
Fluorocarbon salts, infrared spectra of, 455, 456
Fluorocarbon sulfur compounds, 398, 399 infrared spectra of, 458
Fluorocarbon surface, nonadhesiveness of, 352
Fluorocarbons, acetylenic, infrared spec
tra of, 453
Fluorocarbons, analysis for halogens in, 164
Fluorocarbons, analysis of, 163-170 as compounds, 168, 169, 170
by decomposition to fluoride ion, 163, 164
by determination of constituents other than fluorine, 164-168
carbon in, 164, 165 hydrogen in, 162, 164-167 nitrogen in, 168
oxygen in, 167 traces in air, 169 water in, 168 Fluorocarbons,
antimony containing, 326, 399 basis of properties, 335, 336, 337 chemical properties of, 347-364 determination of molecular weight of,
169, 170
difficulties of decomposition for analy
sis, 74, 75
dipole moments of, 364
energy of vaporization of, 357, 358 high temperature equilibria of, 358-362 high temperature reactions, thermo
dynamics of, 359, 360, 361 infrared spectra, comparison with hy
drocarbons, 451 infrared spectra of, 449-529 infrared spectrograms of, 459-528 interfacial tensions with water and
hydrocarbons, 351
mass spectrometer cracking patterns, 161
nitrogen containing, production of, 344 olefinic, infrared spectra of, 454 physical properties of, 347-364, 405-
436
production of, 341, 345 purification of, 349, 350 pyrolysis of, 347 reactions with
fluorine, energies of, 360 hydrogen, energies of, 359 water, energies of, 359
refractive indices of, 363, 364 removal of fluorine from, 335 rotational isomers in, 353
saturated, chemical properties of, 347, 348
secondary standard for liquid state, 354 selenium containing, 327, 399
solubility of chlorine in, 354 nitrogen in, 354
organic substances in, 355, 356 solubility properties of, 353-357 sulfur containing, production of, 326,
327, 342
surface properties of, 351, 352 theoretical considerations, 338, 339 thermodynamic properties of, 362, 363 utilitarian applications, 339
viscosity of, 352 x-ray patterns of, 160
Fluorocarbons and organic compounds, decomposition by
alkali metals, 80, 81 alkaline fusion, 81 hydrolytic methods, 83
reaction with silicon dioxide, 81, 82, 83
sodium in liquid ammonia, 79 decomposition for analysis, 74-83 determination in stream of hydrogen,
79
oxidation methods of decomposition, 76, 77, 78
reduction methods of decomposition, 78, 79, 80, 81
reviews of analytical methods, 75, 76 table of decomposition methods, 77 Fluorocarbons in air,
determination of, 59 tests for, 101
Fluorochemicals, methods of production, 340-346
Fluorochromates, 24 Fluorochromites, 24 Fluorocobaltates, 30 Fluorocolumbates, 22
Fluoroethanes, analysis of, 158 Fluoroethylenes, analysis of, 158, 159 Fluoroferrates, 30
Fluoroform, analysis of fluorine in, 80
Fluorogallates, 10 Fluorogermanates, 13, 14 Fluorogermanic acid, 13 Fluorohaf niβtes, 16 Fluoroindates, 10 Fluoroiodates, 28 Fluoroiridates, 32 Fiuoromanganites, 28, 29
Fluorometallatee, x-ray patterns, 160 Fluoromethane, analysis of fluorine in, 80 Fluoromethanes,
analysis of, 158, 159 microwave, 162
Fluorometric methods, 149, 150 Fluoromolybdates, 25, 26
Fluoronaphthalene, analysis of fluorine in, 76
Fluoroniobates, analysis of fluorine in, 89 Fluoroosmates, 32
Fluoropalladites, 32
Fluorophosgene, analysis of, 158 Fluorophosphates, 17, 18, 19
analysis of, 158, 159 of fluorine in, 78, 110, 141
determination of fluorine in, organic, 103
tests for, 99
Fluoroplatinates, 32, 33 Fluoroplumbates, 14 Fluoroprene, 217, 269, 270 Fluoroprotactinates, 22 Fluoropyridines, 243, 244 Fluoroquinolines, 244 Fluororhenates, 29 Fluororhodates, 31 Fluororhodites, 31 Fluoroselenites, 24
Fluorosilanes, analysis of fluorine in, 83 Fluorosilicate of sodium, 12
Fluorosilicates, 13
analysis of, 124, 158, 162 of fluoride in, 131, 132 of fluorine in, 87, 89, 175, 177 qualitative analysis of, 91 tests for fluoride in, 94 Fluorosilicic acid, 12 Fluorostannates, 14 Fluorosulfonate,
nitronium, 23 nitrosyl, 23
Fluorosulfonates, 23, 24 Fluorosulfonic acid, 22, 23 Fluorotantalates, 22 Fluorotellurites, 24
Fluorothene, analysis of, 159 Fluorothiophene, 246 Fluorotitanate of barium, 14 Fluorotitanates, 15
Fluorotoluene, analysis of fluorine in, 76 Fluorotoluenes, analysis of, 159
Fluorotyrosine, 258
Fluorouranates, x-ray patterns, 160 Fluorovanadates, 21
Fluorovanadites, 20, 21 Fluorozirconates, 15, 16
Fluorspar, analysis of fluorine in, 175 Fluxes, analysis of fluorine in, 177 Foliage, determination of fluorine in, 172,
173
Food, analysis of fluorine in, 69, 71, 87, 117, 174
Foods, tests for fluoride in, 94 Forbonic, 335
Forbons, 335
Freon, determination of, 58, 59 G
Gamma fluoro-carboxylic acids, 239, 240 Gaseous samples,
analysis of, 55
tests for fluorine in, 102
Gelatin, analysis of fluorine in, 69, 174 Germanium fluorides, analysis of, 158 Glass,
etching of, 156 wellability of, 156
Glasses, analysis of fluorine in, 176 Glucosyl fluoride, analysis of fluorine in,
83
Glutarforimide, 389
Graphite, fluorination of, 345 Grass, analysis of fluorine in, 70 Grignard, fluorocarbon, 327
Grignard reagents, reducing action on fluorocarbon carbonyl compounds, 372
H Halogen fluorides, 39
as ionizing solvents, 44-47
physical properties, 39, 40 Hep tf orane,
analysis of, 158 entropies of, 363 normal,
critical constants of, 363 entropy of vaporization of, 362 heat capacity of, 363
heat of fusion of, 363 heat of transition of, 363 infrared spectra, 353
solubilities organic substances in, 354 solubility of chlorine in, 354
of nitrogen in, 354 surface tension of, 351
thermodynamic properties of, 363 triple point of, 363
vapor pressure of, 363 purification of, 350
Heterocyclic organic compounds contain
ing fluorine. 243-246 Hexafluoroantimonates, 19, 20
structure of alkali metal salts, 20 Hexafluoroarsenates, 19
Hexafluorophosphates, 18, 19 Hexafluorophosphoric acid, 18
Hexforane, normal, infrared spectra, 353 Hexforanes, analysis of, 158
High frequency oscillator titration, 133, 134
Hydrocarbons, fluorination of, 343, 344 Hydrofluoric acid, analysis of, 130, 170,
171
Hydrofluorocarbons, 214-226 aliphatic, 214-220
aromatic, 223, 224
with aliphatic side chain, 220-223 unsaturated, 224, 225, 226
Hydrogen containing fluorocarbons, de
termination of hydrogen in, 67 Hydrogen fluoride,
addition to acetylenes, 216, 217 to olefins, 215, 216
analysis of, 158, 159, 162, 170, 171 of hydrogen sulfide in, 171 of silicon fluoride in, 149, 170, 171 of sulfur dioxide in, 170, 171 of sulfuric acid in, 170 of water in, 170, 171 determination of, 56, 57
in cell gases, 62, 63 in gaseous fluorine, 60 magnetic shielding for, 162 sampling techniques, 170 reaction with alcohols, 215 Hydrogen fluoride in air, tests for, 102 Hydrogen stretching frequencies, 451,
452, 453
carbon-hydrogen, 452 nitrogen-hydrogen, 452 oxygen-hydrogen, 451, 452
I
Infrared absorption, 157, 158, 159, 169 Infrared spectra, 459-528
fluorocarbons and related compounds, 449-533
structural group correlations for double and triple bonds, 457
Infrared spectrometry, 449 Inorganic fluorides,
analysis of fluorine in, 84 determination of gaseous, 57, 58 electron diffraction data, 161 magnetic shielding for, 162 qualitative tests for, 92-100 x-ray patterns, 160
Inorganic fluorine containing materials, ashing procedures, 68-71
ashing using aluminum compounds as fixatives, 71
using calcium compounds as fix
atives, 69, 70
using magnesium compound as fix
atives, 70, 71
evaporation procedures for analysis, 73, 74
fusion procedures for analysis, 71, 72 preliminary treatment for analysis, 6 6 -
74 Insecticides,
analysis of fluorine in, 173, 177 fluorine containing, 258, 259, 260 Insoluble fluorides, tests for fluoride ion
in, 95
Interhalogen compounds, melting and boiling points, 40
Interpιnιtration, heat of, 355
in binary mixtures, 356 Iodine fluorides, 43, 44
analysis of, 158
Iodine heptafluoride, physical properties of, 43, 44
Iodine monofluoride, 43 Iodine pentafluoride,
acids and bases in, 47 conductivity of, 44 physical properties of, 43
reaction to form fluorocarbon iodides, \ 367
with carbon halides, 364 Iodine trifluoride, 43
Iron redox potential, changes with fluoride ion, 137
j
Jellies, analysis of fluorine in, 174 Κ
Kel-F, 260 Ketones,
containing fluorine, 236-238
containing methforyl group, 236, 237, 238
fluorination of. 342 L
Lead chlorofluoride, analysis of fluorine in, 145
Lead fluoride, analysis of fluorine in, 145 Leaves, analysis of fluoride on, 156 Lime, analysis of fluorine in, 175, 177 Limestone, analysis of fluorine in, 70 Lithium minerals, analysis of fluorine in,
175
Lubricants, fluorine containing, 268, 269 M
Magnesium compounds, analysis of fluo
rine in, 177
Magnetic resonance, 162
Margarine, analysis of fluorine in, 174 Mass spectrometry, 161
Meat, analysis of fluorine in, 72, 174
Mιdicinale, fluorine containing, 256 Mercury, alkforyl compounds of, 369, 370 Mercury fluorides, 329
Metal fluorides, x-ray patterns, 160 Metallic compounds, fluorocarbon rad
icals containing, 321-328 Metallic fluoride process, 344, 345 Metallic fluorides, analysis of fluorine in,
89
Metals, separation and purification of, by methforyl beta diketones, 374, 375
Methforane,
compressibility of, 362 hydrolysis of, 347 in air, tests for, 102
photochemical reactions of, 348 virial coefficients of, 362 Methforanes, analysis of, 158 Methforyl acetone, 226, 236 Methforyl acetylene, 225 Methforyl aliphatic ketones, 374 Methforyl and fluorine atom, comparison
of electronegativities of, 391 Methforyl antimony compounds, 326 Methforyl antimony iodides, 326 Methforyl aromatic compounds, 400-403
ultraviolet absorption spectra of, 401 Methforyl arsenic bromides, 325 Methforyl arsenic chlorides, 325, 326 Methforyl arsenic compounds, 324, 325,
326
Methforyl arsenic iodides, 324, 325 Methforyl benzenes, 221, 222, 223, 399
amines of, 402
dipole moments of, 400 hydrolysis of, 399 hydroxides of, 402 nitro compounds of, 403
Methforyl benzyl ketone, reactions of, 373
Methforyl beta diketones, 374, 375 Methforyl bromide, preparation of, 364,
365
Methforyl bromides, ultraviolet absorp
tion spectra of, 365 Methforyl containing
acrylic acid, 265 alcohols, 229-232, 394 aldehydes, 236
carboxylic acids, 240 dyes, 248-253 ketones, 236, 237, 238
organic compounds, 241, 242, 243 organic olefins, 380, 381
styrenes, 261, 262, 263
Methforyl derivatives, analysis of, 158 Methforyl group,
chemical effect on organic compound.
219, 220
effect on organic substances, 225 effects on properties of ethers, 397 Methforyl halides,
carbon halide bond, distance in, 365 microwave studies of, 365
Methforyl iodide, 324, 326, 327
absorption spectra and photochemical decomposition, 368
iodine exchange reaction, 370 reaction with,
acetylene, 368 arsenic, 369 ethforylene, 367 phosphorus, 368, 369 potassium hydroxide, 370 sulfur, 369, 398
Methforyl mercuric hydroxide, 322 Methforyl mercuric iodide, 321, 322 Methforyl methanol, 229, 230 Methforyl methyl amine, 242, 243 Methforyl phenols, 402
Methforyl phosphorus compounds, 323, 324
Methforyl radical, formation of, 348 Methforyl selenium compounds, 327 Methforyl silicon compounds, 328 Methforyl styrenes, 403
Methforyl substituted diphenyl ethers, 397
Methforyl sulfur compounds, 326 Methforyl sulfur pentafluoride, 398 Methforyl, terminal, acids containing, 390 Methforylacetylene, 381, 382
microwave study, 382 reactions of, 382
Methforylbenzenes, halogen derivatives of, 401, 402
Methforylcyclohexforane, solubility of nitrogen in, 354
Methforylene,
effect on organic molecule, 239 life period of, 348
reactivity of compounds containing, 233, 234
Methforylene group, chemical effect in aliphatic compound, 219, 220 Methforylmethoxy containing dyes, 249,
250
Methforylquinolines, 244
Methylene, effect on fluorocarbon mole
cule, 338
Microwave spectrometry, 162 Milk, analysis of fluorine in, 70
Mineral waters, tests for fluoride in, 94, 97, 99
Minerals,
analysis of fluorine in, 70, 89, 153, 154, 173, 174, 175
tests for fluoride in, 94, 97
Molybdenum fluoride, analysis of, 158, 159
Monofluoroacetates, 259, 260 Ν
Nephelometric methods, 150, 151, 152 Neutron scattering, 162, 166, 167 Nitrogen, solubility in fluorocarbons, 354 Nitrogen fluorides, analysis of, 158 Nitromethforane, analysis of fluorine in,
80
Nitrosonium fluoroaurate, 4 Nonofluoroacetic acid, test for, 101 Nonofluorophosphates, 18
Nonofluorophosphoric acid, 17 Nuclear magnetic shielding, 162
Ο
Oats, analysis of fluorine in, 69 Octforane, 339
Octforanes, analysis of, 158 Oils, fluorine containing, 268 Olefins,
fluorine containing, 224, 225, 226, 240, 241, 242
fluorine containing, additions of alco
hols to, 232, 233
Oleum, analysis of fluorine in, 176
Opal glass, analysis of fluorine in, 72 Ores, analysis of fluorine in, 154, 174, 175 Organic acid chlorides, fluorine contain
ing, 241
Organic acids, fluorine containing, 2 3 8 - 242
Organic compounds,
analysis for fluorine in, 150 analysis of traces of fluorine in, 76 containing fluorine, 213-320
determination of fluorine in, 104, 107 fluorine analysis by Parr bomb, 78 fluorine containing, table of, 271-307 fluorine determined by microchemical
combustion, 77
by pressure combustion, 77 tests for fluorine in, 100, 101 Organic fluorides,
analysis of, 159
electron diffraction data, 161
from organic chlorides, 218, 219, 221, 223
in air, tests for, 101 in water, tests for, 101
removal of hydrogen fluoride from, 335, 336
Organic fluorosilanes, decomposition of, 78
Organic matter, analysis of fluorine in, 71, 154
Organic monofluoride, 215
Organic olefins, methforyl containing, 380, 381
Organometallic compounds, fluorine con
taining, 328, 331
Oxygen, determination of, in cell gases, 64 Oxygen fluoride,
determination of, 58
determination of, in cell gases, 63, 64 Oxygen fluorides, analysis of, 158, Ξ59
Ń
Pentamethforylene nitrogen fluoride, 392 Pentforane,
cyclo, surface tension of, 351 hydro, refractive indices of, 364 iso, surface tension of, 351 normal, infrared spectra, 353 normal, surface tension of, 351
physical properties of, 348 pyrolysis, of, 347
Pentforane-pentane, binary system, 356 Pentforane-tungsten hexafluoride, binary
system, 356, 357 Pentforanes,
analysis of, 158
refractive indices of, 364 Peroxyfluoromolydates, 26 Peroxyfluorotungstates, 26 Peroxyfluorouranates, 27
Pesticides, fluorine containing, 258, 259, 260
Pharmaceuticals, analysis of fluorine in, 177
Phosphate rock, analysis of fluorine in, 70 Phosphates, analysis of fluorine in, 84, 85,
173, 174, 175, 176
Phosphorus, alkforyl compounds of, 368, 369
Phosphorus fluorides, analysis of, 158 microwave, 162 Photometry, 135-155
Physical properties of fluorocarbons, 3 4 7 - 364
Pickling baths, analysis of fluorine in, 176 Plant ash, analysis of fluorine in, 84 Plants,
analysis of fluorine in, 69, 70, 71, 152, 172, 173
tests for fluoride in, 97 Plastics, fluorocarbon, 404
Plating baths, analysis of fluorine in, 176 Poisons, analysis of fluorine in, 87 Polarography, 134, 163
Polyacetforaldehyde, 371
Poly ethforylene, crystal properties of, 363
Polyfluoroprene, 269
Polymers, fluorine containing, 260-270 Polyvinyl fluoride, 266
Potassium fluoroborate, analysis of fluo
rine in, 145
Potassium fluorosilicate, analysis of fluo
rine in, 145
Potentiometric titration, 128-131 Preserves, analysis of fluorine in, 174 Pressor amines, fluorine containing, 257 Procaines, fluorine containing, 255
Propforane,
binary mixtures of, 363 pyrolysis of, 347
Propforanes, analysis of, 158
Propforyl iodide, reaction with sulfur, 398 Propforylene, identification by infrared
spectra, 450
Proteins, analysis of fluorine in, 78 Purity of fluorocarbons, 349, 350 Pyrethrum, analysis of fluorine in, 69 Pyridine, fluorination of, 344
Q
Quadrupole spectra, 162 R
Raman scattering, 157, 158, 159, 169 Rearrangements, fluorocarbon deriva
tives, 346
Redox pairs, changes of potential of, 136 Redox potential, iron, changes with
fluoride ion, 137 Rocks,
analysis of fluorine, 153, 174 tests for fluoride in, 94, 95, 97 Rodenticides,
analysis of fluorine in, 177 fluorine containing, 260
Rotational isomerism in fluorocarbons, 353
Rubbers, fluorine containing, 404 S
Salt, analysis of fluorine in, 174 Sampling of fluorine containing materials,
54
Selenium, fluorocarbon compounds of, 399
Selenium fluorides, analysis of, 158 Silicates,
analysis of fluorine in, 72, 151, 175 tests for fluoride in, 93, 94, 95
Siliceous matrix, analysis of fluorine in, 155
Silicic acid, analysis of fluorine in, 177 Silicon fluoride, analysis of, 57, 158 Silicon tetrafluoride,
determination of, 57, 58
mass spectrometer cracking pattern, 161
Slags, analysis of fluorine in, 72, 177 Sodium chloride, analysis of fluorine in,
177 Soil,
analysis of fluorine in, 68, 69, 70, 71, 72, 87, 89, 152, 153, 173, 174 tests for fluoride in, 97
Solubility, in fluorocarbons, 353-357 Spectra correlations 1350- to 6 5 0 - Cm"
1 region, 456, 458
Spectroscopy, emission, 152 Stretching frequencies,
oxygen-fluorine, 458 unsaturated bonds, 453-456
carbon-carbon double bond, 453 carbon-carbon triple bond, 453 carbon-nitrogen triple bond, 453 carbon-oxygen, acid and anhydride,
455
carbon-oxygen, acid halide, 454 carbon-oxygen, aldehyde and ketone,
454
carbon-oxygen, esters, 455
carbon-oxygen in salts, and amides, 455, 456
nitrogen-carbon-oxygen, 453 Styrene derivatives,
fluorine containing, 261-264 methforyl containing, 261, 262, 263 Succinforic acid, 242
derivatives of, 388 synthesis, 226 Succinforimide, 389
Sulfa compounds, fluorine containing, 256, 258
Sulfur,
alkforyl compounds of, 369
fluorocarbon compounds of, 398, 399 Sulfur compounds, fluorination of, 344 Sulfur containing fluorocarbons, 342 Sulfur fluorides, analysis of, 158 Sulfur hexafluoride, determination of, 58 Sulfuric acid, analysis of fluorine in, 176 Sulfuryl fluoride, 23
Superphosphate, analysis of fluorine in, 70
Surface chemistry of fluorocarbons, 351.
352
Surface properties of fluorocarbons, 351.
352
Swarts reaction, 346 Τ
Tannery waters, analysis of fluorine in, 177
Teeth, analysis of fluorine in, 69, 70, 153, 173
Teflon, 260 analysis of, 159
Tellurium fluorides, analysis of, 158 Tetrafluoroareenites, 19
Textiles, analysis of fluorine in, 177 Thyronine, fluorine containing, 246, 247 Tissues,
analysis of fluorine in, 172, 173 tests for fluoride in, 94
Trichloroethylene, fluorination of, 343 Trifluoroethylene, polymers of, 267 Trimethforyl arsenic, 324, 325 Trimethforyl arsenic dichloride, 325 Trimethforyl phosphorus, 323 Trimethforyltriazine, 384
Tripropforyl nitride, solubilities in, 355 Tungsten fluorides, analysis of, 158, 159 Tyrosine, fluorine containing, 246, 247
U
Ultraviolet absorption, 159, 160 Ultraviolet absorption spectra, fluoro
carbon bromides and chlorides, 365, 366
Uranium, analysis of fluorine in, 154 Uranium fluorides,
analysis of, 158 x-ray patterns, 160
Uranium trifluoride, mass spectrometer cracking pattern, 161
V
Vanadiumoxyfluoride, mass spectrometer cracking pattern, 161
Vegetable matter, analysis of fluorine in, 151
SUBJECT INDEX Vegetables, analysis of fluorine in, 172,
173
Vinyl fluoride, 216, 217, 225, 265, 266 Vinylidene fluoride, 225
polymers of, 267
Viscosity of fluorocarbons, 352
Volatile inorganic fluorides, determina
tion of, 58
W
Water,
analysis of fluorine in, 87, 90, 151, 175 analysis of fluorine compounds in, 175 determination in Freons, 157
tests for fluoride in, 94 Wine, analysis of fluorine in, 69
Wood, analysis of fluorine in, 70, 72, 173 Wood preservatives, analysis of fluorine
in, 173
X
X-ray diffractions, 160, 161 Ζ
Zinc blende, analysis of fluorine in, 72 Zinc ores,
analysis of fluorine in, 175 tests-for fluoride in, 95
Zirconium, analysis of fluorine in, 89 Zirconium and compounds, analysis of
fluorine in, 177
