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I. Linear Polymers (On vaporization these dopolyinerize Lo monomsrie formaldehyde gas) Lower Poly oxymcfcby lone Glycols Parafo rmaideky do Commercial Paraformaldehyde Alpha-Polyoxymcthylcne Betft-Polyoxymctbylene Polyo xy methyl en e Gly col Derivative sf Polyoxymothylenu Di&cctat es Lower PulyoxyinatKyloiie Dimethyl "Ethers Gamina-Polyoxymethylene (Hi gliBi- Polyoxy me thylene Dimethyl Kthera) DulLa-Polyoxyrnethyleno Ep s i 1 on-Pol yo xyra o thy I c no Bu-Polyo xy mu thyl ene II. Cyclic Polymers (On vaporization these do not dopolymerize) Trioxane (Alpha-Trioxy methylene) TetraoxymeUiyleiie HO(CKaO)»-H HO(CHaO)„-H HO(CH50)IJ-H HO(CIUO)„-H KO(CII20 L-Il + HaSO-i (trace) Tabic IB. liWjuiiiIdeliytle Polymiira. Type Formula. CHaCO-OfCHsOVCOCH, CfUQ
60 FORMALDEHYDE true polyoxymethylenes, have apparently never been prepared by the polymerization of monomelic formaldehyde. Paraformaldehyde, the only formaldehyde polymer now being manufactured in large commercial quantities, is a mixture of poiyoxymetlrylene glycols. A* Ave have previously pointed out, paraformaldehyde is an important industrial chemical, finding use wherever formaldehyde is desired in a form that is substantially free of water. The polymerization of formaldehyde is an exothermic reaction. Heats of polymerization, as calculated from available thermochemical data for various polyoxymethylene-type polymers, range from 12 to 15 kcal per mol of formaldehyde. Formaldehyde polymers are classified by structure, molecular weight and, in the ca*e of polyoxymethylene glycols and their derivatives, by the type of end-groups attached to the linear molecules. The system of classification illustrated in Table 15 shows the relation of structure, molecular weight, and end-groups to characteristic properties and offers a logical order for the discussion of the major polymer groups which have received the attention of chemical investigators. It will be noticed that "trioxymethylene" has been omitted from our list of formaldehyde polymers. This name has been so consistent^ misused as a designation for paraformaldehyde and the linear polyoxymethylenes that it can no longer be employed without confusion. LINEAR POLYMERS Linear formaldehyde polymers include the poiyoxymetlrylene glycols, HO*(CH;Q'vH3 polyoxymethylene glycol derivatives, and eu-polyoxymethylene, (CHaCOn. As previously pointed out, the polyoxymethylene glycols are hydrated polymers- chemically and structurally related to methylene glycol. This relationship is clearly indicated in the formulas shown below: Name Structural Formula Methylene glveol HO • CH«- OH Dioxymettivlene glycol HO • CHa • 0 • CHo • OH TriovYinefhvlenc plvcol HO-CH-OCHa-O-CBVOH p lV;t::o\\!!
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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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Page 29 and 30: Chapter 2 Monomeric Formaldehyde Al
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Page 35 and 36: 24 FORMALDEHYDE formaldehyde in ace
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Page 39 and 40: Chapter 3 State of Dissolved Formal
Page 41 and 42: 30 ' FORMALDEHYDE ethylene oxide wi
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Page 45 and 46: 34 FORMALDEHYDE Skrabal and Leutner
Page 47 and 48: 36 FORMALDEHYDE Equilibria of the f
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Page 55 and 56: 44 FORMALDEHYDE formaldehyde (methy
Page 57 and 58: 46 FORMALDEHYDE Toxicity: Physiolog
Page 59 and 60: Chapter 5 Physical Properties of Pu
Page 61 and 62: 50 :H:O/J00 £. Solution 2.23 4.60
Page 63 and 64: 50 FORMA UihlHYhi: by Natta. and Ba
Page 65 and 66: .32 FORMALDEHYDE Partial Pressure,
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Page 71 and 72: Chapter 6 Distillation of Formaldeh
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Page 83 and 84: 70 FORMALDEHYDE formaldehyde soluti
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Page 97 and 98: Table .17, Proportion at "VidyaxymQ
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Page 115 and 116: Chapter 8 ; Chemical Properties of
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Page 125 and 126: FORMALDEHYDE \V;:h a-motiii;, :orn^
Page 127 and 128: 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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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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