Phthalic Anhydride Derivatives. A Partial Collection ... - ACS Publications

piled, and although it does not pretend to include every com- pound that was ever made from phthalic anhydride, it is, never- theless, published here ...
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Mar., 1921

T H E J O U R N A L OF I L V D U S T R I A L A N D E N G I N E E R I N G C H E M I S T R Y

247

ADDRESSES AND CONTRIBUTED ARTICLES ~~

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PHTHALIC ANHYDRIDE DERIVATIVES‘ A PARTIAL COLLECTION OF NAMES A N D REFERENCES

By M a x Phillips COLORLABORATORY, BUREAU OF

DEPARTMENT OF A G R I C U ~ T U R WASHINGTON, E, D. C. Received June 28, 1920

CHEXISTRY,

In connection with some work on the new process for making phthalic anhydride developed in this laboratory, it became necessary to know the number and kind of compounds that can be made from it. Accordingly the following list was com3-Acetaminophthalic anhydride J. A m . Chem. S o d . , 81 (1909), 483 3-Acetaminophthalimide J . A m . Chem. SOC.,81 (19091, 483 1-Acetaminophthalphenylhydrazine J. A m . Chem. Soc., 81 (1909), 483 3-Acetaminophthal-o-tolil J . A m . Chem. SOC.,31 (1909), 483 Acetoiiylphthalimide Rer 21 (1888) 2684 Ber:: a6 (1893): 2198 dcetylphthalimide Be?., 19 (1886), 1400 A~lylphthalimide Ber 28 (1890) 999 Be“:: 26 (1893): 2850 en-Aminobenzaldehydephthalanil J . grakt. Chem., [2] 88 (1913), 810 9-Aminobenzaldehyde hthalanil J . 9rakt. Chem., 88 f)1913), 810 3-Amino-4-phthalic acid J. A m . Chem. SOC.,81 (1909), 483 3-Aminophthalic anhydride J . A m . Chem. SOC.,81 (1909), 483 Anhydro hthalylbisdiketohydrindene Gass. c k m . it& 87 [I11 (1907), 303

Benzenylazoxime-benzenyl-o.carboxylicacid Ber.. 18 (1885). 2463 a-Benzoylaminoacetalcarbox ylic acid Ber., 27 (1894), 3103 Renzoylresorcinolphthalein B e . , 14 (1881), 1864 Btmzylphthalimide Ber., 20 (1887), 2227 Biphthalimide Ann., 228 (1885), 137 Biphthalyl Ann., 164 (1872), 230 Riphthalyl chloride Ann., 228 (1885). 133 e-(Carboxyethylbenzoyl) -3-g-tolylcrotonlactone Ber , 47 (1914), 2708 C-Chloro0uorescein Ann., a88 (1886), 239

piled, and although it does not pretend to include every compound that was ever made from phthalic anhydride, it is, nevertheless, published here in the hope that it may be of some benefit to those working along this line.

p-Cresolphthalein anhydride Ann., ala (1882), 340 Cresorcinolphthalein Ann., 216 (1882), 95

P-Cresoxyethylphthalamide Ber., 24 (1891), 191 Cyanobenzylphthalimide Ber., ao (1887), 2231 3-Diacetaminophthalimide J. A m . Chem. SOC.. 31 (1909), 483 Diacetylphthalhydraqide J. prakt. Chem., [Z] 61 (1895), 382 Diallylphthalide J. Russ. Phys. Chem. Soc., 44 (1912), 1868 Diamidofluorescein Ann., 183 (1876), 35

9-Diaminobenzylsulfidephthalide Ber., 28 (1895). 1339 Dihromodimethylanilinephthalein Ber., 10 (18771, 1623 Dibromodinitrotluorescein Ann., 183 (1876), 61 3,4-Dichloro-5 ,6-diiodo- hthalic anhydride J . A m Chem. Soc., 4$(1918), 214 3,6-Dichloro-4,5-diiodo-phthalic anhydride J. A m . Chem. Soc.. 40 (1918). 214 . 4,5-Dichloro-3 6-diiodo-phthalic anhydride J . A m . Cheh. SOC.,40 (1918), 214 I,

~

Dichloromethylanthraquinone(2,3)

U. S. Patent 902,895

Diethyldisulfidediphthalamide Ber., 24 (1891). 2131 Diethylditoluylphthalamide Ann., 227 (1885), 188 Diethyleosine Ann., 168 (1876), 50

6,6’-Dihydroxynaphthol0uorane Ber., 47 (1914). 1076 3,CDiiodo hthalic anhydride J . A m . &em. SOC.,40 (1918), 214 3,6-Diiodo-phthalic anhydride J. A m . Chem. SOG.,40 (1918). 214 Diisopropyl phthalate Caxz. chim. ilal., 28 [ I I ] (1898), 50 2,B-Dimeth 1 3 acetylpyrrolenephthalide Z . phrsiof. ;hem.. 82 (1912). 266 Dimethyl-3-aminophthalic acid hydrochlor :ide (?) J . A m . Chem. SOC.,81 (1909), 483 3,6-Dimeth I0uorane Ber., 46 89131, 1484 Dinitrofluorescein Ann., 188 (1876), 30 Di-a-diphenylenephthalamicacid Monatsh., 28 (1907), 411 Diphenylene-oxide-keto-benzoic acid Monatsh., 28 (1907). 411 Diphenylphthalamide Ann.. a27 (1885). 190 Di hthalethylenqdfimide Eaxx. chim. ital., 24 [ I ] (1894), 405 Di hthalsuccinanilide %e,., 18 (1885), 3123 Di hthalsuccinidehydranilide ger., 18 (1885), 3123 Di hthalyl-2 5-diaminohydroquiml 8 a m . c h i d ital.. 16 (1886), 254 Diphthalyllactone Ber., 46 (1913), 1484 Di hthalyl-o-phenylenediamine honatsh., 89 (1918), 873 Diresorcinolphthalein Ber , 13 (ISSO), 1654 Ethylbenz ylsulfidephthalamide Ber., 26 (1892), 3050

Ethylenediphthalamide Ber.. 21 (1888), 2670 Ethylenedi hthalimide Ber., 20 ?1887), 2225 Ethylenephthalamide Gam. chim. ital., 24 [ I ] (1894), 405 Ethyleosine A n n . , 183 (1876), 15 Ethyl ester of phthalglycine Ann., 248 (1887),5 Ethylphenolphthalein Ber., 17 (1884),669 Ethylphenylphthalamide Ann.. 237 (1885), 185 Ethylphthalimide Ber., 10 (18771, 1645 Ethyl a-phthaliminopropionate Ber., 88 (1900), 980 Ethylsulfonediphthalamide Ber., 24 (18911, 3103 Fluorescein carboxylic acid Ber 11 (1878) 3103 Wit%. akad. S A . , 121 77, 224 Hematoxylin phthalein Ber.. la (1879). 1651 Rydrobiph~halyl’ Ber., 17 (1884), 2180 Hydroquinolphthalein Ber 6 (1873) 506 Ber:: 11 (187d. 713 Hydroxybiphthalyl Ann., 238 (1886), 244 8-Hydroxyethylphthalamide hydrochloride Ber.. 21 (1888). 572 Hydroxyphthalamide Ann., 205 (1880), 306 Hydroxyphthalanil Ber., 9 (1876), 1528

8-Hydroxytrimethylenediphthalimide B n . , B 1 (1888), 2690

Isoamylphthalamide BW., as (i890),998 N-Isopropylene-aminophthalimide Ber., 27 (1894), 691 ,5-Chloronaphthanthraquinone Is0 ropylphthalide W. S. Patent 941.320 Ebxz. chim. ital., 28 [ I I ] (1898), 501 8-Chloro hthalanil. Ber., 1’1 (18781, 2260 Kryptopyrrole hthalide Cbloroquinophthalone (sulfonated) 2. ghysiol. R e m . , 62 (1912), 266 U. S. Patent 890.588 1-Methyl-3-aminophthalic acid hydrochloride Chloro-o-xylylphthalimide J . A m . Chcm. SOC.,81 (1909), 483 Ber., 21 (1888), 580 N-Methylcarbazole-3 7-diphthalddehydic acid Compound CaHtNsOa Monatsh., sa ( i g i i j , 1103 A m . Chem. J . , 9 (1887), 220 N-Methylcarbazole-3-phthaldehydicacid Compound (addition) of KOH and phthalic Monatsh.. 82 (1911). 1103 anhydride Methylenediphthalikide J. A m . Chem. Soc., 89 (1917), 2646 Bev., 28 (1890), 1002 Condensation product of phthalimide and forMethylenephthalamide maldeh de Ber., 26 (1893), 957 Ber , 31 &898), 3230 Methyleosine e n d e n s a t i o n product of phthalimide and forMon. sci., 20 (1878), 1171 maldehyde Methylphthalhydrazine Ber., 81 (1898). 2732 J. Drakf Chem , 121 61 (1895), 382 Condensation product (resin) Methylphthalimide U. S. Patent 1,108,329 A n n , 247 (1888), 302 Condensation product (resin) 2-Methyl-4-quinazolone-5-carboxylic acid U. S. Patent 1.108.330 J . A m . Chem. Soc., 81 (1909), 484 Condensation product (resin) Monomethyltetrabromoiluorescein (methlrleryU. S . Patent 1,108,331 thrin) Condensation product containing nitrogen Ann., 188 (1876), 50 D. R. P. 202,354 Chem. Abs.. 8 (1909). 492 Naphthylphthal‘ ide ccresolphthalein ’’ Gaze. chim. i t a r 16 (1885), 346, 480 Ber., 12 (1879), 237 Nitrobenzylphthalimide Ann., 202; (isso), 153 Ber., 20 (1887), 2227 1 In addition to.the well-known journals, for which the standard American Chemical Society abbreviations are used, the following publications are indud$, with abbreviations as noted: Beitrage zur Chemischen Physiologie und Pathologie ” by Franz Hofmeistef,: Beitr. che.m. physiol. (Hof.). “Fortschritte der Theertarbenfabrikation,,und verwaAdter Industriezweige by F. Friedlander: Friedl “Handbuch der Fiif;berei der Spinnfassen by Knecht, Rawson and Lowenihal, 2nd Ed. (Berlin, 1900) : ’Handb. “Parbstofftabellen by G. Schultz, 5th Ed. (Berlin, 1914): Schullz. “Wiener akademis’ches Berrchte:” Ween. akad. Ber “Zusammenstellung der Patente auf dem Gebiete d;r organischen Chemie,” 1877 t o 1904. by Adolf Winther: Winthcr.

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T H E JOURATAL O F INDUSTRl.4.L A N D ENGILVEERING C H E M I S T R Y

Nitrobiphthalyl Ann., 233 (1886), 243 Nitrophthalanil Ber., 28 (1895), 1120 Nitrophthalanilide Ber., 28 (1895). 1120 4-Nitrophthalic acid Ann 208 (1881) 224 Ber.,”l8 (1885), j448 Nitrofluorescein Bull. SOC. chim., [2] SO (1878), 531 Orcinolphthalein Ber., 7 (1874), 2314 Ann., 183 (1870), 63 Phenolphthalein anhydride Ann., 212 (1882), 347 Phenoxyethylphthalamide Ber., 2a (1889), 3255 Phenylenediethylacetone Ann. 133 (1865) 259 Ber.,’4 (1871), 65)s Ber., 9 (1876) 1230 A n n , 202 (lShO), 68 Phenylphthalamide Jahresber., 1847-48, 605 Phenylphthalanilurethane Gam. chim. ital., 16 (1886), 253 N-Phenylphthalimide (phthananil) Ann., 210 (1881), 267 3-Phenyluraminophthalimide J. Am. Chem. Soc., 31 (1909), 483 P h t halall ylpseudocumidoamide Ber., 17 (1884), 1808 Phthalaminothiophenol Ber., 13 (1880), 1233 Phthalamide Am. Chem. J., 3 (1881-1882), 29 Phthalanil-o-carboxylic acid Ber., as (18961, 2679 Phthalcarhoxylic acid Ber., 31 (1898), 369 Phthalchloride D. R. P. 139,553 Phthaldinitromesidil Ber., 16 (1882), 1017 Phthalglycine J. prakt. Chem., [2] a7 (1883), 418 Phthalhydrazide J. prakt. Chem., [21 51 (1895), 396 Phthalhydrazideacetic acid J. prakt. Chem., [2] 61 (1895), 383 Phthalic acid Ann., 76 (1850), 1 1-Phthalidene-3-p-methoxystyrylcrotonolactone Bev., 47 (19141, 2708 I-Phthalidene-3-phenylcrotonolactone Bev., 47 (1914), 2708 Phthalimide Ann 41 (1842) 98 Ber.,”31 (1898),’2732 sym-Phthalimide Ber., 19 (1886), 1398 m-Phthalimidobenzoic acid Ber., 16 (1883), 1320 o-Phthalimidobenzoic acid Bey., 11 (1878), 2261 1-Phthalimido-2-nitro-p-tolunitrile Bey., 27 (1894), 2165 Phthalimidosulfonic acid A n n . , 233 (1886), 226 a-Phthalimino-N-ethyl butyrate Bey., 33 (1900), 980 Phthalisocymidide Ann., 221 (1883), 169 Phthalmesidil Ber., 16 (18821, 1017 Phthalnitroisocymidide Ann., 221 (1883), 169 Phthalnitromesidil Bev., 16 (18821, 1017 Phthaloxime Am. Chem. J., 47 (1912), 89 Phthalpseudocumidide Ber., 17 (1884), 1802 Phthalpseudocumidoamide Ber., 17 (1884), 1802 Phthalpseudocumidomethylamide Ber., 17 (1884), 1808 Phthalureide Ann., 114 (1882), 23 Phthaluric acid Ann., 214 (18821, 19 Phthalyl-p-aminobenzoic acid Bcr., 10 (1877), 579 Phthalyl-N-aminobutyronitrile Ber., 12 (1889), 3337 Phthalylaminocapric acid Ann., 242 (1887), 9

Phthalyl-o-aminodiphenylmethane Ber., 27 (1894), 2786 Phthalyl-9-aminophenol Arch. Pharm., 234 (1896), 620 Phthalyl-0-aminophenol acetate Arch. Pharm., 234 (1896), 620 Phthalyl-p-aminophenol benzoate Arch. Pharm., 234 (1896), 620 Phthalyl-p-aminophenol butyrate Arch. Pharm., 234 (1896), 620 Phthalyl-p-aminophenol propionate Arch. Pharm., 234 (1896), 620 Phthalylasparagineaminohenzoic acid Gazz. chim. ital., 16 (1886), 7 Phthalylasparaginephenylimide GQZZ.chim. %tal.,16 (1886), 7 Phthalylasparaginic acid Gazz. chim. ztal., 16 (1886), 2 P h t halylchloride Ber., 19 (1886), 1187 Phthalylcyanacetylene J. pvakt. Chem., I21 39 (1889), 275 Phthalyldiaminoacetal Ber., a7 (1894), 3102 Phthalyldicreatinine Beitu. chem. physiol. ( H o f . ) ,9, 183 Pht halyldisarcosine Ber., 21 (1888), 278 Phthalyldiphenylasparagine Gazz chim. ital., 16 (1886), 10 Phthalylguanidine J. pvakt. Chem., [2] 49 (1894), 42 Phthalylhydroxylamine Ann., 206 (1880), 295 Phthalyltaurine J. Chetn. Soc., 54 (1888), 1303 2,4,6-Picrylphthalimide Ber., a2 (1889), 3257 Styrylphthalamide Ber., ‘26 (1893), 1857 Styrylphthalimide Ber., 26 (1893), 1857 Sulfoamidophthalic acid Ann., 233 (18861, 229 3-Sulfophthalic acid Ann., a33 (1886), 220 4-Sulfophthalic acid Ann., 143 (1867), 257 4-Sulfophthalic acid monochloride Ann., 233 (1886), 228 4-Sulfophthalic acid trichloride Ann., 233 (1886), 228 Tetrachlorophthalic anhydride U. S. Patent 322,368 Tetramethyl-3-azo-phthalate J. Am. Chem. Soc., 31 (1909), 483 Tetraphenylpht halamide Ber. 16 (1882) 830 Ann’., aa7 (isah, 192 o-2-Thenoylbenzoic acid Ann., 407 (1915), 94 Thiophthalic anhydride Ber., 17 (1884), 1176 Thiophthalic naphthoquinone U. S. Patent 852,158 3-4-6-Triiodophthalic anh dride J. Ant. Chem. Soc., 40 8 9 1 8 ) , 214 Triphthalylpicramide Gazz. ckim. ital., 16 (1886), 253 o-Xylylenephthalimide Ber., 2 1 (1888), 579 Ber., 26 (1893), 2213 Xylylphthalimide Ber., 21 (19881, 576 XANTHENEDYJ%S Alkyl ester of dialkyl-homo-rhodamine U. S. Patent 516,585 Aureosin (chlorofluorescein) D. R. P. 2618 Chrysoline Mon Sci. [3] 7 (1887), 860 Jahrksber.: 1887, 1233 Heumann 1 463 Handb. t i n & ed.). ?65 Cerulein paste A B e y . , 4 (1871), 5.56 Cerulein B, BR, BW in paste, BWR in powder Ann., 183 (1876), 28 Schults, 204 Cerulein S in paste; Cerulein S W in paste; Cerulein MS; Alizarin green; Anthracene green A n n . 209 (1881) 272 Dingier’s polytech’. J., aa9 (1878), 178 Schultz, 205 Handb. (2nd ed.), 1062

1’01. 1 3 . NO. 3

Cyanosine (alc. sol.) Handb 768 Schultz‘,’201 Cyanosine B (J) Schultz, 203 Diethyleosine Ann., 183 (1876), 50 Diethylrhodamine U. S . Patent 456,081 Dimethyldiethylrhodamine U. S. Patent 576,222 Dimethylmethylrhodamine (not esterified) U. S. Patent 578,578 Diphenyldichlororhodamine U. S. Patent 413,049 Diphenylrhodamine U. S. Patent 413,048 . Diphenyltetrachlororhodamine U. S. Patent 413,050 Eosine BN; Nopalin G; Safrosin J Ann. 183 (1876) 61 Ann.: 202 (1880): 68 Heumann. 1. 483

Erythrosin B; Pyrosin B; Dianthrene B Mon. Sci., 20 (1878), 1171 Erythrosin D Heumann, 1, 489 Erythrosin (extra blue) Dingler’s polytech. J. 263 (1887), 66 Dingler’s polytech. J . : 283 (1892), 258 Erythrosin R (J); Erythrosin (extra yellow) Handb., 767 Ethyl ester of tolurhodamine U. S. Patent 821,452 Gallein Alizarin violet’ Anthracene violet Ber. ‘4 (1871) 457 j 5 5 , 663 An;,., 209 ( l s b l ) , 49 D. R. P. 30,648 ,Meth yleosine Mon. Sci., 20 (1878), 1171 Metliyleosine J Ann. 183 (1876) 53 Chem’.-Ztg., 16 (1’892), 1956 Monomethyltetrabromofluorescein ( m e t h y l erythrin) Ann., 183 (1876), 50 Phloxin P. New Pink; Erythrosin BB British Patent 44,779 Chem. tnd., 3 (1880);59 Handb., 768 Schultz, 201 Phloxin N , BB; Eosine blue; Cyanosine [DH]; Eosine 10 B Schulta, 202 Handb. (2nd ed.), 768 Phthal green Corn&.206 Ann. rend,, (1880) lad (1897), 112 221 Primrose, Eosine alc. sol. Ann. 183 (1876) 46 Dingier’s polytech’. J. 263 (1887), 49, 99 Dingler’s polytech. J.; 283 (1892), 210 Rhodamine B ; Rhodamine 0; Safraniline Brit. Patent 15,374; ’96,000 U. S. Patent, 377,349 : 377.350 D . R . P. 44.002: 48.3I67 . @;.Patent -i86,697 Chem - Z t g 16 (1892) 1056 J. So;. Chk‘m. I n d . , 12 (1893), 513 Rhodamine 3 B. Anisoline D. R. P. 66,228; 71,490; 73,451 U. S. Patent 499, 927 Bull. 7 (1892) 523 C h e i . - Z t g . , 16’(1892), 1956 Schultz, 192 Rhodamine G D R P.63325 U: S.‘Pateni 516,588 Fr. Patent 215,700 Friedl., Winthev,3,2,175 192

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Rose hengal 2 B; Rose bengal B; Bengalrose 2 B Handb., 768 Schultz, 203 A sulfonated amino-oxyphthalein or toluylrhodal U. S. Patent 609,997 Tetraethylrhodamine U. S. Patent 377,350

Mar., 1921

T H E J O U R N A L OF I N D U S T R I A L A N D E N G I N E E R I N G C H E M I S T R Y

Tetramethylrhodamine U. S. Patent 377.349 Triethylbenzylrhodamine sulfo U. S. Patent 609,998 Uranine; Fluorescein Bcr.. 4 (1871). 558. 662 Ber.; 8 ii875j; 146’ dnn., 183 (1876), 2 Ann., 212 (1882), 347 Ber., 7 (1874), 1211 .I. SOC.C h e n . I n d . , 6 (1887), 283 J . SOC.Chem. I n d . , 11 (1892), 675 Chem.-Ztg., 16 (1892), 1956 .I. SOC.Chem. I n d . , 12 (1893), 513 Ber., 21 (1888), 3376 E e r . . 34 (1891). 1412 B e y ; 2s (18925; 1385, 2118, 3586 Ber., 38 ( 1 8 9 3 , 28 B e ? . , 44 (1911), 312, 396, 428

QUINOLINEDYES Quinaldine yellow U. S. Patent 290,585 Brit. Patent 136.283 Schultz, 210 Winther, 2, 786 Ber., 16 (1883), 297, 878, 513, 1082 uinoline yellow (alc. sol.) D. R . P. 23,188 uinoline yellow (water sol.) D. R . P. 23,188

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uinophthalone U. S . Patent 290.585 Brit. Patent 136,283 Ber., 16 (1883), 297, 298 Ber., 16 (1883), 513, 1082 Ann., 315 (1901), 303

THE AMERICAN POTASH INDUSTRY AND ITS PROBLEMS’ By John E. Teeple 5 0 EAST4 1 s ~STREET,NEW YORK,N . Y. Economic conditions growing out of the war left two chemical foundlings on our shores. One was the dye industry and the other the potash industry. The first proved to be a noisy one, and we have been kept rather well informed of its progress, its possibilities, its hopes, and particularly its needs. The potash industry has been far less noisy, although we have been kept informed from time to time that we have such an industry. But when we ask, “How much of a potash industry have we?” -“Is it a permanent one?” and “Can it either now or in the future compete with the German potash industry, or must it temporarily or always receive protection as an infant industry in order to exist?” we find a considerable divergence of opinion. I want t o discuss some things regarding the progress and problems of this American potash industry, its present position, and its hopes. POTASH IN THE UNITED STATES

This is primarily an agricultural country. It normally consumes 250,000 tons KzO per year, which is equivalent to 400,000 tons of 100 per cent KC1 (potassium chloride). This figure, of course, includes all grades of potassium salts brought into this country, and over 90 per cent of the total is used on the land as fertilizer. Before the war we produced no potassium salts a t all in this country, with the exception of an infinitesimal amount of potash leached from wood ashes. Even the caustic potash made in this country was made from imported potassium chloride. When the war shut off commerce with Germany and the country awoke to the fact that it had no potash and that it must have it t o produce the large crops that were needed, our Government sent out urgent requests to hasten the discovery and the production of potash from every possible source. These urgent Tequests, together with the high price which could be obtained for any salts containing potassium, resulted in the installation of plants to work the natural brines ol Nebraska, California, and Utah; the dust from cement kilns and blast furnaces; the waste liquors from distilleries and beet-sugar factories ; the alunite deposits of Utah; the leucite deposits of Wyoming; the kelp fields of the Pacific coast; the wood ashes of Michigan; and even the greensand of New Jersey. I n all we find a total of over 100 different plants built to produce potash from these sources. In 1918, the banner year, 123 different plants operated, giving a total production of over 54,000tons KzO. I n 1919, with the €all of the price of potash, this production dropped to about 30,000 tons: and, while the figures are not yet available for 1920, the production will be probably in the same neighborhoodthat is, something like one-eighth of the country’s requirement. 1 Based on addresses given before the Rochester and Cornel1 Sections of the American Chemical Society. January 24 and 25, 1921.

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ANTHRAOUINONE DYES Alizarin brown-R N G, F, H, WR Handb. (2nd eh.),’1046 Schults, 270 Anthracene brown W, WR, WG Ber., 10 (1877), 38

INDIGO DYES Indigo Literature extensive-see Schultz, 297-298 UNNAMEDDYES U. S . Patent 929,422 U. S. Patent 1,196,127 U . S. Patent 968,533 U. S . Patent 688,885 U S. Patent 633 883 U: S Patent 540’564 U. S: Patent 990:224 U. S. Patent 675,216 U. S. Patent 188,217 U. S . Patent 211,180 D. R. P . 275,670

Out of the 128 plants reported as producing in 1918, only 43 were reported as producing in 1920. With the price of potash in 1921 still lower than i t was in 1920 we may expect a still greater falling off in the number of producing plants, and possibly in the total output. Up to the present time probably 70 per cent of the total production of potash in this country has come from natural brines. These natural brines include a whole series of lakes in Nebraska, the Salduro Marsh in Utah, and Searles Lake in California. There are eight plants working on the Nebraska brines, one on the Salduro Marsh, and three on Searles bake. Just now, of the eight Nebraska plants five are closed down and only one of the three plants on Searles Lake is in regular operation. SEARLES LAKE POTASH

The oldest and largest of the plants working on Searles Lake and also the largest producer of potash in the United States is the American Trona Corporation. In 1918, the year during which the United States produced more potash than it has ever done before or since, this one plant was responsible for about one-seventh of the entire production of the country. To-day this one plant is probably responsible for about 30 per cent of the production of the United States, and as it seems to be making more progress and spending more money in studying its problems than any other potash organization, a study of its difficulties encountered and results achieved should give us some basis for predicting the future. I hope that a study of these difficulties will be interesting from a chemical and engineering point of view, and a t the same time it will show us why the industry has not progressed faster than it has, why potash is not yet as cheap as i t was before the war, and why we may expect that with moderately good fortune a permanent potash industry can be founded here. When I first assumed responsibility for the operations of this concern about a year and a half ago, I found a going plant which represented an investment not far from $lO,OOO,OOO,but which still did not seem particularly well adapted to the purpose for which it was built. It was producing a t that time only a moderate tonnage of potassium chloride, averaging less than 70 per cent in purity, and its production costs were high. Many different processes had been tried a t this plant in a desultory manner, many millions of dollars had been spent, not always wisely, and even with such a brief history behind it the plant was being run on tradition rather than on information. This is not said in a spirit of petty criticism, for we all realize that pioneer work when done under pressure for production is not usually accompanied by careful, painstaking work, calm judgment, and economical operation. The whole spirit under such conditions is one of snap judgment and lavish expenditure, and a certain amount of both is excusable and unavoidable. In any case, by the middle of 1919 the plant had passed the pioneer stage and the press for production where such modes of operation could be excused, and was entering on a period where a n entirely different