TP GIFT OF D.D. [Reprinted from the Journal of Industrial and Engineering Cbemiitry, Vol. 11, No. 3, page 263. March, 1919.] Bibliography on Carbonyl Chloride (Phosgene) and Its Derivatives By D. D. Berolzheimer i C 51 (Reprinted from the Journal of Industrial and Engineering Chemistry, Vol. II, No. 3, page 263. March, 1919.] BIBLIOGRAPHY ON CARBONYL CHLORIDE (PHOSGENE) AND ITS DERIVATIVES By D. O. BKROLZHKIMBK, Assistant Technical Editor, The Chemical Catalog Company, New York City This bibliography is based upon that published by the late Dr. Morris Loeb, in bis Ph.D. thesis of 1887 (see reference 129), being revision and amplification of same. The author will be glad to have any errors or omissions in the bibliography called to his attention. The numbers following each entry refer to the literature citations In the appended list of references, page 264. Standard Refor.ncws Beibteln, 1, p. 546 Beltatein Suppl.. 1, p. 219 Richter, 1, p. 36 Stctanr, p. 26 I Production From carbon monoxide and chlo- rine: 1, 4, 6, 11, 23, 35. 69, 97. 215, 248, 250. 252, 258 Prom carbon bisulfide and hypo- chlorous acid anhydride: 32 Prom carbon bisulfide, chlorine, and sulfuric acid: 2, 8 Prom carbon tetrachloride: 21, 33, 37, 46, 153 Prom chloroform: 26, 27, 28, 153 Prom perchloroformic acid methyl ester: 10 Prom sodium trichloroacetate : 8, 7 1 II Liquaf action 181 III Purification 84 IT PropartUi 27, 38, 57, 68, 79, 93, 129, 154, 156, 159, 188, 190. 207, 208, 218, 220, 224, 228 T Reactions With the following compounds or classes of compounds: Acctaldehyde: 15, 17, 20, 29, 31, 34. 108 Acetamide: 47 Acetic acid: 44, 45, 235 Acetic acid ester: 106, 119 Acetone: 24, 44 Acetylamidobeatylpiperidines: 166, 168 Acetylated diamino bases: 166, 168 Acetzylide: 158 Acid*: 44, 45, 180, 231. 234, 235 Alcohols: 3, 5. 12, 50, 55, 76, 84, 113 Aldehydes: 15, 17, 20. 29, 31, 34. 44,49, 108, 117, 173 Aliphatic hydrocarbons: 18, 39, 42 Alkali metal alloys or amalgams: 221, 222 Alkaline hydrogen peroxide: 253 Alkyl toinidines: 237 Alkyl substituted ammonium salts: 96, 111, 123, 125 AHophan amide (biuret): 47 Alloys of alkali metals: 221. 222 Aluminum bromide: 161, 185 Aluminum chloride: 179 Aluminum iodide: 189 Amalgams of alkali metals: 221, 222 Amides: 47, 48, 59, 83, 96, 157 Amidines: 116, 121, 130, 239, 240, 242 Amidoacetic acids: 212, 213 Aminoanthraquinones: 200, 201, 202, 203, 204, 205, 209 Amidoazobenzene : 102 Amidobeniylplperidine: 223 Amidodimethylanilinc: 80 Amidoisobutylbenzene: 102 Amidozimes: 109, 112 Amidophenetol : 160 Amidopropylbenzene: 95 Amidosulfonic acids: 128 Amines: 1, 7, 9, 13, 25, 54, 58, 60. 61, 62, 63, 64, 70, 73, 74, 75, 78, 79, 80, 81, 82, 87, 88, 89, 94, 95, 97, 100, 101, 102, 114, 116, 121, 122, 127, 130, 131, 132, 133, 141, 143, 145, 146, 149, 155, 158, 160, 174, 187, 194,. 206, 225, 236, 237, 239, 240, 241, 242 Ammonia: 1, 7, 13, 25, 70 Ammonium chloride: 126, 137 Amylmercaptan: 56, 104 Aniline: 9,96, 160 Aniline hydrochloride: 96 Anilinophenylethanes: 229, 230 Anisidine: 75 Anthracene: 30, 105, 124 Antipyrine: 194 Aromatic hydrocarbons: 16, 30, 39, 65, 66, 67, 107, 110, 120, 124, 167, 172, 194 Benzaldehyde: 44, 173 Benzamide: 47 Benzene: 16, 39, 66 Benzenylamidoximes: 109 Benzidine: 80 Benzidine hydrochloride: 123 Benzy lace t amide: 158 Benzylbenzamlde: 158 Biuret: 47 Boron bromide: 161, 182 BromoMenzene: 36 Butenjpdiphenyldiamine : 131, 242 Cadmium sulfide: 148 Carbazines: 136, 140 Carbazol: 149 Chloral: 173 Chloroacettc acid: 234 Chloranthranilic acid : 196 Chlorhydrins: 85 Cresol: 44 Cyanides: 162 Cymidine: 97 Dialkylamine: 194 I lianisalacetone: 199 Diazoamldobcnzene: 82, 86 Diazoamido compounds: 82, 86 Oiazobenzene toluidide: 82. 86 Dibenzylamine : 146 Diisobutylamine: 145 Diethylamine: 58 Diethylaniline: 58, 63 Dlmethylaniline: 60, 61, 62. 63, 87, 88, 89, 94, 114, 115 Dimethylamlne: 74. 89 Dimethylbenzaxnide: 59 Dinaphthylamine: 143 Diphenylamine: 60, 64 Diphenylhydrazine : 175 Diphenylkctene: 244 Dlphenylurea: 96 Diphenylurea azo compounds: 135, 138 392622 THE JOURNAL \i)F INDUSTRIAL AND ENGINEERING CHEMISTRY Vol. n, No. 3 Ditolylamine: 146 Ditolylthiourea : 83 Epichlorhydrin : 44 Kthenyldiphenylaraido oximcs: 112 Ethenyldiphenyldiamine: 116, 121, 130, 239, 240, 242 Ethenylditoluyldiamines: 131, 242 Ethyl alcohol: 3, 76 Ethylamine hydrochloride: 125 Ethylene glycol : 92 Ethylenediphenyldiamine: 81, 127 Ethyl xanthate: 184 Eugenol: 117, 193 Fatty acid salts: 96, 97 Formates: 139 Gallic acid: 231 Glycol: 92 Glycolchlorhy drin- 118 Glycollic acid ester: 43 Guaiacol: 193 Guanidines: 78, 79 Hydrazin derivatives: 136, 140, 142, 157 Hydrocarbons: 16, 18, 30, 39, 41, 42, 65, 66, 67, 105, 107, 110, 120, 124, 167, 172, 194 Hydrogen peroxide (alkaline): 253 Hydrogen sulfide: 163 Hy droquinone : 147 Inorganic compounds: 1, 7, 13, 25, 52, 53, 70, 126, 137, 148, 161, 162, 163, 179, 182, 185, 186, 189, 192, 216, 217, 221, 222, 227, 238 Isoamyl alcohol: 12 Isobntenyldiphenyldiamine : 131, 242 Isopropyl alcohol: 50, 134 Ketones: 24, 44 Lactic acid: 44 Magnesium organic compounds: 176, 177 Malonlc acid hydrazide: 136 Mercaptans: 51, 56, 103, 104 Metals of the alkali group: 221 , 222 Metal oxide*: 216 Metal sulfides: 148, 217 Menthol: 219 Methane: 232, 243, 245 Methyl alcohol: 5, 84, 113 Methylatnine hydrochloride : 125 Methylaniline: 73 Methyldiphenylamine: 104, 115 Methylphenylthiocarbazide: 164, 178 Naphtholi: 117, 193 Naphthylene diamine: 225 Nitroamldophenol: 144 Nitrophenol: 44 Nitrososulfonic acids: 128 Organo-ammonium compounds: 96, 111, 123, 125 Organo-magnesium compounds: 176, 177 Oxarnidi. t? , 48 Oxides: 238 Oximes: 109, 112 Oxybenzenes: 147 Oxybyazolones: 136, 140 Oxyphenylaminoacetic acid: 212, 213 Plicnanthrene: 124 Phenols: 44, 77, 90, 99, 117, 147, 169, 170, 171, 193, 198, 219, 233 Phenolates: 90, 169, 170, 233 Phenol sulfonite: 150 Phenyl cyanate : 98 Phenylhydrazins: 123, 136, 142 Phenylnaphthylamine: 143 Phenylphosphine: 72 Phenylenediamines: 141,236 Phenylenediamine hydrochloride: 111 Phosphates: 227, 238 Phosphonium compounds: 163 Piperidines: 166, 168 Platinum: 52, 53 Potassium cyanide: 162 Primary amines: 1, 7, 9, 13, 25, 54, 70, 75, 80, 95, 96, 97, 102, 160, 237 Propenyldiphenyldiamine: 131, 242 Propionitrile: 14 Propyl alcohol: 55 Pyridine: 167, 194 Pyrrol: 107 Quinoline: 101, 171, 194 Rare earths: 216 Resorcinol: 77, 147 Salicylic acid: 180 Salicylic acid esters: 193 Salicylic aldehyde: 117 Salicylosalicylic acid: 191 Secondary amines: 58, 60, 64, 73, 74, 80, 81, 82, 121, 122, 127, 130, 131, 132, 141, 143, 158, 174, 194, 206, 225, 236, 239, 240, 241, 242 Seleniuretted hydrogen : 163 Silicates: 227 Silicomethane: 22 Sodium acetate: 44, 235 Sulfides: 139, 163, 217 Sulfoureas: 151 Tertiary amines: 58, 60, 61, 62, 63, 87, 88, 89, 94, 100, 101, 114, 115, 133, 194 Thiodinaphthylamine: 149 Thiophen: 110 Thiophenol: 117 Thiosemicarbazides: 164, 178, 197, 214 Thymol: 44 Toluene: 65, 172 Toluidines: 54, 237 Toluylenediamine hydrochloride: 123 Tritnethylenediphenyldiamide: 127 Tyrosine and homologs: 183, 212, 213 Ureas: 47, 151, 165 Urethanes: 122, 132, 241, 242 Xylene: 67, 120 Zinc methyl: 19, 40 VI Products of Reactions Acetyl chloride: 44, 234, 235 Acetylamidobenzyl chlorides: 223 Acid carbonate: 191 Acid chlorides: 16, 18, 19, 30, 36, 39, 40, 41, 42, 58, 60, 61, 62, 63, 65, 66, 67, 87, 88, 89, 94, 105, 107, 110, 114, 115, 120, 124, 169, 170, 171, 172, 174, 234, 235 Aliphatic acids and anhydrides: 96, 97, 139 Anhydrous chlorides: 44, 133, 192, 199, 216, 217 Anhydrides of fatty acids: 44, 96, 97 Anthracene carboxylic acid chloride: 30, 105, 124 Anthranilic acid esters: 196 Benzal chloride: 44 Benzophenones: 68, 60, 61, 62, 63, 87, 88, 89, 94, 114, 115, 133 Carbamides: 1, 7, 9, 13, 25, 47, 54, 58, 60, 64, 70, 73, 74, 75, '80, 81, 82, 95, 102, 127, 141, 142, 145, 146, 149, 155, 160, 165, 174, 183, 201, 202, 203, 204, 205, 206, 209, 212, 213, 225, 236, 237 Carbamic acid chlorides: 58, 60, 64, 73, 74, 81, 82, 127 Carbanilide: 9, 96 Carbon oxysulfide: 148 Carbonyl bromide: 161 Carbonyl chlorobromide : 161 Carbonyl chlorplatinites: 52, 53 Carbonyl cyanide: 162 Carbonyldiurea: 47, 165 Carbonyl pyrrol: 107 Carboxylic acid esters: 3, 5, 12, 43, 44, 50, 51, 55, 56, 76, 77, 84, 92, 99, *103, 113, 117, 118, 134, 150, 169, 170, 171, 193, 196, 198, 219, 233 Chlorination products: 15, 17, 18, 19, 20, 24, 25, 29, 30, 31, 34, 36, 39, 40, 41, 42, 44, 58, 60, 61, 62, 63, 65, 66, 67, 87, 88, 89, 94, 105, 107, 108, 110, 114, 115, 120, 124, 163, 172, 173, 192, 193, 198, 216, 217, 223, 232, 243, 245 Chloroformic acid esters: 3, 5, 12, 43, 44, 50, 51, 55, 56, 76, 77, 84, 92, 99, 103, 113, 117, 118, 233 Cyanuric acid: 47, 165 Diaminodiphenyl carbamide: 236 Dichloroacetone : 44 Diparaphenetol carbamide: 160 Diphenyl carbamide: 9, 96, 160 Diphenyl carbonate: 90 Diphenyl carbazide: 142 Diphenylthiourazol: 197,214 Dipyrrol acetone: 107 Esters: 3, 5,' 12, 43, 44, 50, 51, 55, 56, 76, 77, 84, 92, 99, 103, 113, 117, 118, 233 Ethylxanthic anhydride: 184 Isocyanates: 96, 111, 123, 125, 166, 200 . Keto chloride: 199 Ketones: 16, 18, 19, 30, 36, 39, 40, 41, 42, 58, 60, 61, 62, 63, 65, 66, 67, 87, 88, 89, 94, 105, 107, 110, 114, 115, 120, 124, 172, 211 Methyl chloride: 232, 243, 245 Methyl violet: 89 Michler's ketone: 58, 60, 61, 62, 63, 87, 88, 89, 94, 114, 115, 211 Naphthalene carbamide: 225 Oxyanthrimidazole: 209 Phenyl isocyanate: 96 Phenylurea: 212, 213 Pyrrone: 107 Selenium chloride: 163 Sulfamyl: 56, 104 Symmetrical ureas: 1, 7, 9, 13, 25, 54, 70, 75, 80, 95, 102, 183, 212, 213 Tetramethyldiaminobenzophenone : 61, 62, 63 Thiocarbanilides: 151 Thorium chlorides: 192 Tyrosin urea: 183 Urazole derivatives: 164,178 Ureas: 1, 7, 9, 13, 25, 47, 54, 58 60, 64, 70, 73, 75, 80, 81, 82, 95, 102, 127, 141, 145, 146, 149, 155, "160, 165, 174, 183, 201, 202, 203, 204, 205, 206, 209, 212, 213, 225, 236, 237 Urea chlorides: 143 Ureides: 47, 48, 59, 83, 96, 212, 213 VII Miscellaneous As an agent for arresting isonieric change: 187, 195 Bactericidal and antiparasitic prop- erties: 226 As solvent for chlorides of sulfur in ebullioscopic determinations 186 Toxicological action: 210, 224, 246, 251 General reactions: 194 Removing free chlorine from car* bonyl chloride: 84 Use in the dyestuff industry: 152 Statistical discussion of manu- facture. 254 Testing chloroform for presence of Carbonyl chloride : 1 60 REFERENCES 20 1 Davy. 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Abs.. 11 (1917), 847) 1916 Whitehouse. U. S. P. 1231226, June 26 (Chem. Abs., 11 (1917), 2396) 1917 Zunz. Ambulance de I'ocean, 1, 2S7;(Chem. Abs., 13 (1918). 1897) 1917 Garner. Am. Gas Eng. J., 108, 489 and 505; (Chem. Abs., IS (1918), 1827) 1918 Kleinstueck. Ber., 51, 108; (Chem. Abs., IS (1918), 1721). . . 1918 Raxous. L'industrie chimiyue. 5, 3; (Chem. Abs., 11(1918). 1108) 1918 Hcriy. J. Ind. Ent. Otum., 11. 9 1919 THIS BOOK IS DUE ON THE LAST DATE STAMPED BELOW AN INITIAL FINE OP 25 CENTS 392622 UNIVERSITY OF CALIFORNIA LIBRARY