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388 Properties of formaldehyde—Cont'd. Physical*—Cont'd. Paraformaldehyde, 71-72 Polvoxymethylene diacetates, 82-S3, ~S4-S5 Polyoxymethylene dimethyl ethers, Trioxane, 95-96 Physiological; Hexaniethylenetetraroine, 2S6 Trioxane, 99 Solvent, aqueous solutions, pure, 56-57 Thermodynamic, trioxane, 96-9S Propionaldehyde, reaction of formaldehyde with, 153-154 Proofing, crease- and crush, use of formaldehyde, 362~3&t Protein fibers, use of formaldehyde, 367-368 Protein resins, 312-315 Proteins: Reactions of formaldehyde wish, 221- 224 Reactions of hexamethyienete'Eramine with, 296 Purity, commercial formaldehyde solutions, 39-40 Q Quantitative analysis, formaldehyde solutions and polymers, 255-274 Assay of commercial formaldehyde, 266-274 Metallic impurities, 270 Methanol, determination of. 267-270 Formaldehyde, determination of, 267 Formic acid, determination of, 267 Assay of commercial paraformaldehyde, 270-271 Formaldehyde content, 271 Chemical methods, 256-266 Alkaline peroxide method, 2S&-259 Ammonium chloride method, 260- 261 Hydroxylamine hydrochloride method, 263 lodhnetrie method, 259-260 Mereurimetric method, 261-262 Methone method, 263-266 Potassium cyanide method, 262-263 Sodium sulfite method, 257-258 Determination in special compositions and in products treated with formaldehyde, 271-273 Dusting powders, 273 FORMALDEHYDE Formals, determination of combined formaldehyde in, 273 Fungicides, 273 Hexamethylenetetramine, 297-263 Medicinal soaps, 272 Phenol and phenol-formaldehyde condensates, mixtures containing, 272 Physical methods, 255-256 Products treated with formaldehyde determination of combined formaldehyde in, 273-274 Seed-conserving agents, 273 R Reaction mechanism., production oi formaldehyde from methanol, 4-5 Reactions of formaldehyde; Acetaldehyde: Gas-phase reactions involving, 153 In water solution, 150-151 Acetone, 155-157 Acetylenic hydrocarbons, 237-238 Acid anhydrides, 193 Acids, 133-135 Acyl chlorides, 193-194 Addition, 109-112 Methylol derivatives, 114 Alcohols, 138-140 Joint, with hvdrogen halides and, 144-146 Aldehydes, with, 150-155 Acetaldehyde: Gas-phase reactions involving, 153 In water solution, 150-151 Pentaerythritol production, 151-153 Aromatic, 155 Higher aliphatic, 153-155 Aldol-type condensations, 106-108 Alkali and alkaline-earth hydroxides, 117-119 Alkali metals, 117 Amides, 206-216 Diamides, 215-216 Monamides, 206-20S Substituted ureas, 213-215 Urea, 208-210 Urea-formaldehyde resins, 211-213 Amines, 199-206 Aliphatic, 199-203 Aromatic, 203-206 Amino acids and esters, 220-221 Aminonitriles, 218-220 Ammonia, 120-121 Ammonium salts, 121-123 Aniline, 203 Aromatic aldehydes, 155
Aromatic hydrocarbons, 231-237 Dlarylmetbanes, formation of, >35- 237 Halornethylation reactions, 231-235 Reams? formation of, 235-237 Aryl aliphatic ketones, 159-160 Cannizzaro, 106 Carbamates, 216 Carbon monoxide, 126 Carboxylic acids, 191-193 Casein, 221-224 Cellulose, 143-144 Condensation, 109-112 Cyauarnides, 218-220 Cyclic ketones, 158-159 Di-ketones, 159 Diamides, 215-216 Esters, 194-19S Formaldehyde with formaldehyde. 106-108 Aldol-type condensations, 106-10S Cannizzaro reaction, 106 Polymerization reactions; 106 Tischenko reaction, 106 Gas-phase, involving formaldehyde and acetaldehyde, 153 Glue, 221-224 Glvcerols, 140-142 Glycols, 140-142 Halogens, 135 HexamethyleneteLramine, 286-296 Inorganic compounds, with, 286-292 Organic compounds, with, 292-296 Higher aliphatic aldehydes, 153-155 Higher aliphatic ketones, 157-15S Hydrazine, 123-124 Hydrocarbons, with, 227-242 Acetylenic, 237-23S Aromatic, 231-237 Diarylme thanes, formation of, 235-237 Halomethylation reactions, 231- 235 Resins, formation of, 235-237 Cyclo-olefins, 227-230 Halogenated olefins, 230-231 Nitro-, 240-242 Olefins, 227-230 Cyelo-, 227-230 Halogenated, 230-231 Organometallic derivatives, 233-240 Hydrogen: Cyanide and cyanides, 125-126 Peroxide and peroxides, 126-129 Sulfide and sulfides, 129-131 Hydrohalogen acids, 134-135 SUBJECT IXDEX Hydroxides, 119 Hydroxy compounds, with, 13S-146 Alcohols. 13S-I40 Cellulose, 143-144 Glycols and glycerols. 140-142 Joint, with alcohols and hvdrogen halides, 144-146 Starch, 142-143 Sugars, 142 Hydroxylamine, 124-125 Imides, 216 Inorganic agents, with, 117-135 Acids, 133-135 Acids: Hydrohalogen acids, 134-135 Xitric acid, 134 Xitrous acid, 134 Phosphoric acid, 133-134 Sulfuric acid, 133 Alkali and alkaline-earth hydroxides, 117-119 Alkali metals, 117 Ammonia, 120-121 Ammonium salts, 121-123 Carbon monoxide, 126 Halogens, 135 Hydrazine, 123-124 Hydrogen: Cyanide and cyanides. 125-126 Peroxide and peroxides, 126-129 Sulfide and sulfides, 129-131 Hydroxides, 119 Hydroxylamine, 124-125 Metal oxides, 119 Metallic salts, 119-120 Metals, 119 Phosphorus halides, 135 Sulfur dioxide and sulfites, 131-133 Involving two or more types, 115 Joint, with alcohols and hydrogen halides, 144-146 Ketones, with, 155-160 Acetone, 156-157 Aryl aliphatic, 159-16X3 Cyclic, 158-159 Di-ketones, 159 Higher aliphatic, 157-158 Melamine, 21S Mercaptans, with, 146-147 Metal oxides, 119 Metallic salts, 119-120 Metals, 119 Methylol derivatives, 113^-115 Addition reactions, 114 Condensation with other compounds, 114
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Formaldehyde Tank Cars. Courtesy B.
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Copyright, 1944, by REIXHOLD PUBLIS
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iv FORMALDEHYDE of the highest valu
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Introduction Formaldehyde chemistry
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Page o y GENERAL IxrRODrcTiON iii P
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Page CHAPTER IS. HEXAIIETHYLEXEIETR
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Early History of Formaldehyde FORMA
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FORMALDEHYDE Production of Formalde
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6 POEM ALDEHYDE 30-cm hard-glass tu
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_ 3, "Formaldehyde unit developed b
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10 FORMALDEHYDE hyde. A modern plan
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12 FORMALDEHYDE catalysts contain f
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14 FORMALDEHYDE decompose at temper
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18 FORMALDEHYDE comprising aluminum
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Chapter 2 Monomeric Formaldehyde Al
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20 FORMALDEHYDE u-av contain small
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22 FORMALDEHYDE turea from 25 to 12
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24 FORMALDEHYDE formaldehyde in ace
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2G FORMALDEHYDE polymerizes very sl
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Chapter 3 State of Dissolved Formal
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30 ' FORMALDEHYDE ethylene oxide wi
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32 FORMALDEHYDE cal equilibrium bet
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34 FORMALDEHYDE Skrabal and Leutner
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36 FORMALDEHYDE Equilibria of the f
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38 FORMALDEHYDE molecule is saturat
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40 FORMALDEHYDE develop measurable
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42 ' FORMALDEHYDE present in the mo
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44 FORMALDEHYDE formaldehyde (methy
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46 FORMALDEHYDE Toxicity: Physiolog
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Chapter 5 Physical Properties of Pu
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50 :H:O/J00 £. Solution 2.23 4.60
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50 FORMA UihlHYhi: by Natta. and Ba
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.32 FORMALDEHYDE Partial Pressure,
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54 FORMALDEHYDE Lacy 17 * has recen
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50 FORMALDEHYDE At temperatures bel
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Chapter 6 Distillation of Formaldeh
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60 FORMALDEHYDE and that the soluti
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62 FORMALDEHYDE was found to contai
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Chapter 7 Formaldehyde Polymers Pol
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60 FORMALDEHYDE true polyoxymethyle
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6S FORMALDEHYDE sodium sulfate, and
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70 FORMALDEHYDE formaldehyde soluti
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72 FORMALDEHYDE ance of a colorless
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74 FORMALDEHYDE centrationa the rea
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76 FORMALDEHYDE the vacuum concentr
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78 FORMALDEHYDE mately 0.1 to 0.3 p
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80 FORMALDEHYDE dehyde solution was
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S2 FORMALDEHYDE ingers studies of t
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Table .17, Proportion at "VidyaxymQ
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SB FORMALDEHYDE soluble solid diace
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ss FORMALDEHYDE gradually increases
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go FORMALDEHYDE sulfuric acid were
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92 FORMALDEHYDE molecules. This con
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94 FORMALDEHYDE temperature. Since
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96 FORMALDEHYDE are forming or evap
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9S FORMALDEHYDE of formaldehyde to
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100 FORMALDEHYDE sublimate in the f
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Chapter 8 ; Chemical Properties of
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104 FORMALDEHYDE modif}- the decomp
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106 FORMALDEHYDE Reactions of Forma
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IMS FORMALDEHYDE i-.n^ ;t!i a-i^-at
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Ha FORI! ALDEHYDE arid 'ii:„-":.;
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FORMALDEHYDE \V;:h a-motiii;, :orn^
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m FORMALDEHYDE Under anhydrous cond
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116 FORMALDEHYDE 34,1. G. Farbenind
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118 FORMALDEHYDE The effect of alka
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120 FORMALDEHYDE precipitates. Coll
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122 FORMALDEHYDE On heating solutio
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124 FORMALDEHYDE prepared it by gra
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126 FORMALDEHYDE By reaction of 960
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X2S FORMALDEHYDE On reaction of two
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130 FORMALDEHYDE methylene glycol d
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132 FORMALDEHYDE Although this acid
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134 FORMALDEHYDE evolved and carbon
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m FORMALDEHYDE References I. Anders
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Chapter 10 Reactions of Formaldehyd
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ttJSAUTiuivs WITH HYDROXY COMPOUNDS
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142 FORMALDEHYDE alcohol with forma
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144 FORMALDEHYDE that no stable con
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146 FORMALDEHYDE hydrogen halide, a
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148 FORMALDEHYDE Z, Backer, H. :..
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152 FORMALBEH YDE Pentaerythritol i
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] 54 FORMA LDEHYDB Pentaglyeerol ap
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lot; CH2OH),C-CHOH,Cf;CEtOH)8 FORMA
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15S FORM A L DEH YDE In the ease ox
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1,30 FORMALDEHYDE with cold concent
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104 FORMALDEHYDE indicated. rhi> re
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166 FORMALDEHYDE substituted phenol
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H3S FORMALDEHYDE The preparation an
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170 FORMALDEHYDE are slow to react
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172 FORMALDEHYDE produce methylene
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174 FORMALDEHYDE The ether, dimethy
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i7G FORMALDEHYDE ratios, as would b
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ITS FORMALDEHYDE ami it- polviiueU-
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ISO FORMALDEHYDE HO^ /> - CH-OCaq)
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1S2 FORMALDEHYDE On oxidation and h
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154 FORMALDEHYDE ghieinol itseli ar
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l&e H 0 T FORMALDEHYDE O il a c / ^
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1SS FORMALDEHYDE Phenols having thr
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190 FORMALDEHYDE 27. Eanus, F., J.
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192 FORMALDEHYDE Acids containing a
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194 FORMALDEHYDE reaction which tak
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190 FORMALDEHYDE era! hiji;rs. When
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19S FORMALDEHYDE By oxidation with
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200 FORMALDEHYDE cold reaction mixt
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202 FORMALDEHYDE In the case of eth
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204 FORMALDEHYDE *m \it.^:U:Z hi mt
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200 FORMALDEHYDE In av^îu:, -econd
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2QS FORMALDEHYDE Mixed methylene de
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•210 FORMALDEHYDE According to Ka
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12 FORMALDEHYDE Tho t>*.:y:;.*:'k-
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214 FORMALDEHYDE hy employing an ac
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2IM FORMA LDEH YDE In the presence
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21S FORMALDEHYDE On exposure TO dil
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220 FORMALDEHYDE •with 4 or more
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222 FORMALDEHYDE anism by which the
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224 FORMALDEHYDE H'iris \.\\i. :\j:
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220 FORMALDEHYDE 97. SeieiEer, E, T
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22S FORMALDEHYDE Since strongly aci
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230 FOEMALDBBYDE feolsble derivativ
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232 HOCHjCi - j V / u H H CH2C! FOR
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234 CHj CHa / \ FORMALDEHYDE CHs /
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2m FORMALDEHYDE extremely stringent
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23S FORMALDEHYDE silver aeervHde an
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24.0 FORMALDEHYDE alcohol*. Moureu
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242 FORMALDEHYDE Farbenindusnie pat
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Chapter 16 Detection and Estimation
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24ti FORMALDEHYDE iiiriue :'-r vrr.
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*>JS FOIOIALBEHYD, t-,TîKêd «JJ
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250 FORMALDEHYDE Beta-Naphthoi. Bet
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252 FORMALDEHYDE bridle compounds o
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254 FORMALDEHYDE 14. Dtoigts, G., C
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250 FORMALDEHYDE Formaldehyde may a
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23S FORMALDEHYDE analyzed, but shou
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2u0 FORMALDEHYDE by Roniijn :: . Th
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262 FORMALDEHYDE The following modi
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2-', I FORMALDEHYDE lleilione Is ^
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26G FORMALDEHYDE should be neutral
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2i kS FORMALDEHYDE previously m^-ur
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270 FORMALDEHYDE tioii of ike metha
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272 FORMALDEHYDE insoluble material
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274 FORMALDEHYDE hyde liberated by
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Chapter 18 Hexamethylenetetramine H
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27S FORMALDEHYDE show monobasic cha
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2S0 FORMALDEH YDE Reactions I and I
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2S2 FORMALDEHYDE 275"F 135 ; C/. By
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2S4 FORMALDEHYDE On ignition, it bu
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2S6 FORMALDEHYDE Physiological Prop
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2SS FORMA LDEH YDE base or ?JV :he
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290 FORMALDEHYDE Reaction* with Sul
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292 FORMA LDEH1 'BE erately concent
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294 FORMALDEHYDE acetone in boiling
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296 FORMALDEHYDE for 15 minute* wit
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298 FORMALDEHYDE approximately 0/2
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300 FORMALDEHYDE 35. D^v-jkv. -T. V
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Chapter 19 Uses of Formaldehyde, Fo
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304 ' FORMA LDEH YJj£ of both plan
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306 FORMALDEHYDE ent, resistant to
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305 FORMALDEHYDE Resins, joining wo
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310 FORMALDEHYDE has played an incr
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312 FORMA LB Ell 3 V D£ resin-like
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314 FORMALDEHYDE For example, it is
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316 FORMALDEHYDE ically involved in
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Chapter 20 Uses of Formaldehyde, Fo
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320 FORMALDEHYDE 12-24 hours-. Some
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322 FORMALDEHYDE has been utilized
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324 FORMALDEHYDE References 1. Baue
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326 FORMALDEHYDE soaking for four t
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32S FORMALDEHYDE colors is among th
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330 FORMALDEHYDE 7. Jones, H. I., !
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332 FORMALDEHYDE Tetranifcthylenedi
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334 FORMALDEHYDE 0. Rinser, F., :o
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Page 357 and 358: 344 FORMALDEHYDE References 1. Bore
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Page 379 and 380: 366* FORMALDEHYDE spiration can be
Page 381 and 382: 36S FORMALDEHYDE itatrng bath which
Page 383 and 384: 370 FORMALDEHYDE 39. Lantz, L. A.,
Page 385 and 386: Abel, JM 1S1 Acres, S. F., 125 Adam
Page 387 and 388: Lacy, B. S.t 54 Ladisck, C, 215 Lae
Page 389 and 390: IB, 1, Itotaf,!,! Ifflt,0,S i,! ife
Page 391 and 392: Ammonia, reaction, of formaldehyde
Page 393 and 394: Cyclic polymers, 65; 94-100 Tetraox
Page 395 and 396: Hydrocarbon gases, production from,
Page 397 and 398: Polyeondensation of simple, 112 Rea
Page 399: Lower polyoxymethylene glycols, 67-
Page 403 and 404: Latex, 355-356 Synthetic, 358 Salic
Page 405 and 406: ,- T7 Dyes, 327-329 Embalming, 329-
Page 407 and 408: No. 35. Noxious Gases. By Yandell H
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