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HEXAMETHYLEXETETRAMIXE ** jy nêd in hexamethylenetetramine by the usual analytical procedures. In general, no precipitation of silver chloride should result when 5 cc of a 331percent hexamethylenetetramine solution is acidified with a few drops of nitric acid and treated with a drop of A'/IO silver nitrate. Ten per cent barium chloride should not precipitate barium sulfate from a similar solution. The substantial absence of heavy metals is demonstrated if no coloration results when a few drops of 10 per cent sodium sulfide is added to a solution of hexamethylenetetramine in distilled water which has been made distinctly alkaline with ammonia. Ash may be determined by igniting 5 g of hexamethylenetetramine in a weighed crucible. Technical hexamethvlenetetramine should show not more than 0.3 per cent ash; U.S.P. hexamethylenetetramme not more than 0.05 per cent. References . 1. Altpeter, J., "Das Hexfimethylenetetramine wnd Seine Verwejidupg," pp. 31-65, Halle, Verlag von Wilhdra Knapp, 3931. 2. Itnd., pages 5-15. 3. Ibid., pages S0-S3, •4. Ibid., page 25. 5. Ibid.t page SS. 6. Ibid., page 89. 7. Bally, J., IZev. Aluminum, IB, 1155-66 (I22S); C. A., 32, S839. S. Baur, E., and Huetschi, W., Heir. Chim. Acta, 24, 754-67 [1941). 9. Bebie, J. H„ "Manual ofJSxplosivos, Military Pyrotechnics, and Chemical "Wariare Agents," page £1, Mew York, The Macmiilan Co., New York, 1943. 10. Beilstein-Frager-Jacobscm, "<strong>Org</strong>anische Chemie," Vol. I, pages 5S&-7; I (&uppl.), 30S-11, Berlin, Julias Springer, 191S and 1938 feuppl,). 11. Birehall, T., and Coffer* &.. (to Imperial Chemical Industries Ltd.) V. S. Patent 2,021,550 ;1S30', 12. Bordeianu, C. V., Ann. Sei. Univ. Jaa$y.t IS, 3S0-3 (1929); C 'A,, 23, 3189 (1929), 13. BUchi, J., Pharni. Acta Heh., 13, 132-7 (193S). 13a. Buratti, R., Swiss Patent 90,703 (1921); Chem. Zentr.r 1922, TV, 891- 14. Butlerov, (Butlewr) A., Ann.t 111, 350 (1859). 15. Butlerov, (Butlerow) A., Ann.* 115, 322 (1SG0). 16. Butlerov, (Butierow) A., Ann., 115, 353 (I860). 17. Cambist, B.T, and Brocket, A., Bull. soc. chim. France ($), 13,354. IS. Carles, P. J., Pharm. Chim, (7), U, 279; JZayerf- pharm,, 28, 139 (1916); C. A., 19, 1896. 19. Carter, C. B., and Case, A. B., (to S. Karpen & Bros.), TJ. S. Patent 1,499,001 (1924). 20. Carter, C. B., (to S. Karpen & Bros.) TJ. S. Patents 1,489,002 (1924); 1.56&.S22 (1925); 1,630,752 (1927); 1,635,707 (1927). 21. Carter, C. B,, (to S. Karpen and Bros.) U". S. Patent 1,566,820 (1935). 22. Chemnitus, F-, Chan. Zt$„ 52, "35 (192S). 22a. Davis, T. L.T "The Chemistry of Powder and Explosives," Vol. II, page 451, John WUey & Sons, ^BW York, 1943. 23. DeKeine, M., Bull. *w* chim, France (3), llr 552 (1S95). 24. Delepine, IT., Bull. soc. chim. France (3), U, 74 (1S95). 25. Delgpme, MM Bull. soc. chim. France (3), 13-,136 (1S95)- 26. Delepine, H., Bidl. soc. chim.France (S), 13, 353 (1S95); 17,110. 27. DelfSpine, M.( Com.pt. rend., 123, SSS (1S96). SS. Delepine, 31.. 5«IL «*• cAiffl. Fra^s (3)> 17,292. 29. Dele"pine, M., Bull. soc. chim. France (3), 17,390. 30. Delepine, M., Bull. soc. chim.France Q), 9,1025 £1911). 31. Dem*g, H., and Kelly, M-, (io Superfine Chemicals, Ltd.), British Paten*%HA8tHft&5- 32. Desrergnes, L., CAun. rf Iwd. 2S, 103S (1932). 33. Dickinson, It. G., and Raymond, A. L., J". Am. Chem. Soc., 45, 52 (19&)*C 34. Dominikiewics, M., ^rcft. Cfom. Farm., 4,1-7 (1933); Ci**». Zwtr^ 1M£2I, 1 & S3- tf f *
300 FORMALDEHYDE 35. D^v-jkv. -T. V„ u;-'i Werîr^, IV. D.. Be\. 49, 1041 ;:?:•} . JU Duden, P.. ar.d Scharff, 11., AKH., 2SS. 2J3-22Q ,1595 . 37. Dudmr P., ar.dacharff, M., Ber., 28,533 ,']5^5:. MS. Du£,.J. C, and BilU, E. J.,/. Cte«-. Soc.r 1929. 4Ei. 8P. D;iff, J. C, 7. J. D. Hiedel A.-C, German Patent337,939 (1921). 65. Kag&nors, F. I., and Shul'mann, A. A., Farm. Zftnr., 12. No. 3,15-16 (19391. 60. Kirchho?, F.t Gummi-Ztg., 39. S92 (1925); C. .4., 19, 2424. 70. Klinov, I. Va., Orff. CS^. /nd. (U.S.S.R.), 7. 45-S (1940). 71. Knudsen, P., Bfr., 42, 39P4 (I&09 j. 72. Kollo, C. and -Vngelescu, B., Bull. soc. chim. (Rumania), S, 17-20 (1926); C, A., 22.1302. 7S. Kolosov, S., Xavosti TeibiiJh", 1936„ Xos. 40, 41, and 42; C. A.? 31, 3002. 74. Kbrostishev-ska, L., Farm. Zhur., 13. No. 2, 2S-27 (1940); C. î.r 35, S4S. 75. Landftt-Bernsleui, "Thi.-sikalish-Chemischen Tabellen," 3rd. Suppl., 5th Ed., page 3911, Berlin. Julius Spriager, 1935. 76. Iândt, G-> and Adams, W.( {to Continental Diamond Fiber Co.) L\ 3. Patent 1,774,929 (19301, 77. Lebach, H., r. ange.it. Cksin., 22, 1600 (1909); C. A., 4,391. 7S. Legler, L., £ir.5 18, 3350 (1SS5). 79. Letdier, A., cfoi,T J". pAomi.c&fri.,29.343-61 (10S3);C. A., 34. 73. 50. Leyt H„ Ann., 278,59 (lSWj. 51. Lobering, J-, and Philippi, E., BiocAem. 2,, 277,365-75 (1935); C. Au, 29. 4655 J1933). 52. Losefcann, G., CAem. Zf0., 14,140S (18901; Ckem. Zenir., 1890, II, S14. 53. Mannich.CândHahn, F. L., Per., 44. 1542 (lflU). St. Mark, H., Ber., 57.1820 (1924); C. A., 19, 754. 85. Marottn, D., and Allessandiini, M. E., .
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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.
Page 261 and 262: *>JS FOIOIALBEHYD, t-,TîKêd «JJ
Page 263 and 264: 250 FORMALDEHYDE Beta-Naphthoi. Bet
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Page 267 and 268: 254 FORMALDEHYDE 14. Dtoigts, G., C
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Page 277 and 278: 2-', I FORMALDEHYDE lleilione Is ^
Page 279 and 280: 26G FORMALDEHYDE should be neutral
Page 281 and 282: 2i kS FORMALDEHYDE previously m^-ur
Page 283 and 284: 270 FORMALDEHYDE tioii of ike metha
Page 285 and 286: 272 FORMALDEHYDE insoluble material
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Page 289 and 290: Chapter 18 Hexamethylenetetramine H
Page 291 and 292: 27S FORMALDEHYDE show monobasic cha
Page 293 and 294: 2S0 FORMALDEH YDE Reactions I and I
Page 295 and 296: 2S2 FORMALDEHYDE 275"F 135 ; C/. By
Page 297 and 298: 2S4 FORMALDEHYDE On ignition, it bu
Page 299 and 300: 2S6 FORMALDEHYDE Physiological Prop
Page 301 and 302: 2SS FORMA LDEH YDE base or ?JV :he
Page 303 and 304: 290 FORMALDEHYDE Reaction* with Sul
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Page 307 and 308: 294 FORMALDEHYDE acetone in boiling
Page 309 and 310: 296 FORMALDEHYDE for 15 minute* wit
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Page 315 and 316: Chapter 19 Uses of Formaldehyde, Fo
Page 317 and 318: 304 ' FORMA LDEH YJj£ of both plan
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Page 321 and 322: 305 FORMALDEHYDE Resins, joining wo
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Page 325 and 326: 312 FORMA LB Ell 3 V D£ resin-like
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Page 331 and 332: Chapter 20 Uses of Formaldehyde, Fo
Page 333 and 334: 320 FORMALDEHYDE 12-24 hours-. Some
Page 335 and 336: 322 FORMALDEHYDE has been utilized
Page 337 and 338: 324 FORMALDEHYDE References 1. Baue
Page 339 and 340: 326 FORMALDEHYDE soaking for four t
Page 341 and 342: 32S FORMALDEHYDE colors is among th
Page 343 and 344: 330 FORMALDEHYDE 7. Jones, H. I., !
Page 345 and 346: 332 FORMALDEHYDE Tetranifcthylenedi
Page 347 and 348: 334 FORMALDEHYDE 0. Rinser, F., :o
Page 349 and 350: 33(3 FORMA LDEHYDE low dishes or on
Page 351 and 352: 338 FORMALDEHYDE sistance and other
Page 353 and 354: 340 FORMALDEHYDE complUhed by deriv
Page 355 and 356: M2 FORMALDEHYDE is reported thai t'
Page 357 and 358: 344 FORMALDEHYDE References 1. Bore
Page 359 and 360: 341) FORMALDEHYDE distilled water a
Page 361 and 362: 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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