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DETECTION OF FORMALDEHYDE 249 The method appears to be one of growing importance. Its use \> naturaUy restricted to solutions which are free from materials whose halt-wave potentials? are in the region —1.4 to -l.S volts. Procedure: According to Boyd and Bambach*, best results are obtained wter. 3 cc of the solution to be tested are mixed with 1 ce of a solution which is 0.4A' in potassium chloric^ and 0.2,\ in potassium hydroxide. Xitrogen is bubbled through the resulting solution for 15 minutes, after which a polarogram is taken from -1.4 io -tS volts. The Leeds and Xorthmp Eleetro-chemograph is recommended. The h&lf^vave of the formaldehyde step is reported* to occur at -1,63 volts (normal calomel electrode). The solution should be kept in a constant-temperature bath controlled to 0.1 £ C during the determination, since the wave height is stated io change bv about 6.0 per cent for each l c change in temperature- Boyd and Bambaeb state that- 3 ppm of formaldehyde can be determined. Jahoda 30 claimed that 0.07 npm may be estimated with an accuracy of 10 per cent. In genera] the method appears applicable to any formaldehyde solution which can be isolated by distillation or is otherwise free of interfering"substances. Boyd and Bambach state that acetaldehyde is reduced at a potential of —l.S volts (normal calomel electrode). This aldehyde and formaldehyde can be estimated simultaneously if the potassium electrolyte is replaced by lithium hydroxide. The potassium wave interferes with acetaldehyde detection. A polarogram obtained by the above investigators showing -both formaldehyde and acetaldehyde is shown in Figure 17. IDENTIFICATION OF FOHMALDEHYDE For purposes of identification, it is often desirable to prepare characteristic formaldehyde derivatives whose identity can be certified by melting points, analyses, etc. The following reagents are of value for this purpose in cases involving small quantities of formaldehyde. Methone (dimethyldihydroresorcinol, 5,5-dimethyl-cyclohexanedione). A diauclear methylene derivative of this agent, methylene bis-methoneT is precipitated when a few drops of a o to 10 per cent solution of the reagent in alcohol is added to the solution to be tested, which has been made faintly add with acetic acid. The precipitate obtained with formaldehyde melts at 1S9°C after recrystallization from hot alcohol. The presence of salt in the reaction mixture is stated to increase sensitivity, which is claimed to be approximately 4 ppm. Methylene bis-methone is soluble in dilute alkali and does not become alkali-insoluble after heating on a boiling water bath with a small amount of glacial acetic acid for 6 to 7 hours, Methone derivatives of other aliphatic aldehydes become alkali-insoluble when treated in this way (pages 265-266). p-Nitropnenylhydrazine Hydrochloride. This agent precipitates a p-nitrophenylhydraône from mildly acid formaldehyde solutions. On purification from alcohol, the product melts at 181-1S2°C 5 ' 49 . 2,4-Dinitrophenylhydrazine Hydrochloride. This agent LS used in the same manner as the one mentioned above. Formaldehyde-2,4-dinitrophenylhydrazone melts at 166-167°C 1(U1 .
250 FORMALDEHYDE Beta-Naphthoi. Beta-naphthol react* with formaldehyde in acid solution :u inve n precipitate of methylene dinaphthol 13 . Application of this res: involve.- the treatment *JI a few drops or formaldehyde solution with
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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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Page 213 and 214: 200 FORMALDEHYDE cold reaction mixt
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Page 229 and 230: 2IM FORMA LDEH YDE In the presence
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Page 239 and 240: 220 FORMALDEHYDE 97. SeieiEer, E, T
Page 241 and 242: 22S FORMALDEHYDE Since strongly aci
Page 243 and 244: 230 FOEMALDBBYDE feolsble derivativ
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Page 247 and 248: 234 CHj CHa / \ FORMALDEHYDE CHs /
Page 249 and 250: 2m FORMALDEHYDE extremely stringent
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Page 257 and 258: Chapter 16 Detection and Estimation
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Page 265 and 266: 252 FORMALDEHYDE bridle compounds o
Page 267 and 268: 254 FORMALDEHYDE 14. Dtoigts, G., C
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Page 293 and 294: 2S0 FORMALDEH YDE Reactions I and I
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Page 307 and 308: 294 FORMALDEHYDE acetone in boiling
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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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33(3 FORMA LDEHYDE low dishes or on
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338 FORMALDEHYDE sistance and other
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340 FORMALDEHYDE complUhed by deriv
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M2 FORMALDEHYDE is reported thai t'
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344 FORMALDEHYDE References 1. Bore
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341) FORMALDEHYDE distilled water a
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34S FORMALDEHYDE high wet-strength
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350 FORMALDEHYDE a roll, after whic
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35*2 FORMA LDEH \ 'DK chloride "lit
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354 FORMALDEHYDE forming developers
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356 FORMALDEHYDE In addition, it is
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35S FORMALDEHYDE An entirely differ
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360 FORMALDEHYDE According to Seymo
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362 FORMALDEHYDE improved by an aci
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364 FORMALDEHYDE type because the p
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366* FORMALDEHYDE spiration can be
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36S FORMALDEHYDE itatrng bath which
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370 FORMALDEHYDE 39. Lantz, L. A.,
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Abel, JM 1S1 Acres, S. F., 125 Adam
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Lacy, B. S.t 54 Ladisck, C, 215 Lae
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IB, 1, Itotaf,!,! Ifflt,0,S i,! ife
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Ammonia, reaction, of formaldehyde
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Cyclic polymers, 65; 94-100 Tetraox
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Hydrocarbon gases, production from,
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Polyeondensation of simple, 112 Rea
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Lower polyoxymethylene glycols, 67-
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Aromatic hydrocarbons, 231-237 Dlar
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Latex, 355-356 Synthetic, 358 Salic
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,- T7 Dyes, 327-329 Embalming, 329-
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No. 35. Noxious Gases. By Yandell H
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