2010_11_05_lecture_ch21

2010_11_05_lecture_ch21 - I. \< 2 lo \—/ Y c. AO\—\...

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Unformatted text preview: I. \< 2 lo \—/ Y c. AO\—\ 471‘ :r \\1\1\‘- 0-" {‘fi‘v’lA‘ J)!" O” o— m ’f... x 4‘" ‘ e——9 \/ \/ §° 7 1‘“, H 9 ('9 R «our \a-w MM 3“9—‘1wuura O‘— O \\ H E; C“) cu1 (\(U‘VO- &or~c’dn ‘ 0“".“f' °\—\ C... YVL; Yr-cvcsu\ b ,, Mm. (“—— ehdn- } / ‘ VQA" )" D“ .A‘ .- S!< w:¥;5«-Jn vul- __ Dunnite — Wildpedia, the free encyclopedia , http:f/en.wikipediaprg/wiki/Dunnite Dunnite From Wikipedia, the free encyclopedia Dunnite, also known as Explosive D or . systematically as ammonium picrate, is an explosive developed by Major Dunn in 1906?] Ammonium picrate is a salt formed by reacting picric acid and ammonia. It was used extensively by the United States Navy during World War LB] Though Dunnite was generally considered an insensitive substance, by 1911 the United States Army lUPAC name“ I I The Navy, however, used it in armor—piercing artillery __flafiiHlPllFREltt?WEE..-_.____ ._._._._._ shells and projectiles, and in coastal defense. 1 E E E had abandoned its use in favor of other alternatives.[4] i “Other names Ammonium Picrate; Picratol; 2,4,6—Trinitrophenol . ammonium salt; Ammonium picronitrate; Explosive D Dunnite typically did not detonate on striking heavy armor. Rather, the shell encasing it would penetrate gm,MWWWmmmgkgfiggmm,mmmmm,m the armor, after which the charge would be triggered L945 numbwel‘il31-74-3 WWWWWWWWWWWWWWWWWWWW mm, by a fuse - iEE‘BEFEE-Wig].me W. , w , a, w a - §SM1LES E In 2008 caches of discarded Dunnite in remote §C1:C(C:C(C(:C1[N+](:O)[O_D locations were mistaken for rusty rocks at Cape [0—])[N+](=O)[O-])[N+](=O) Porcupine, Newfoundland and Labrador, Canada. [VQilr-lNlddflw EMolecular §c6146N407 , E . References Jemdemwt ,,,,,,,,,,,,,,,,,,, WWWWW..3 twat.__._§%€E§;i}._._._._._._._._. lDensity 311] i l. A a b Record ofAmmoniumpikrat :rMmij—wwmgrlizlgwg/mgnmwwmmmww"MWWMWWMWWWrg (http://biade.itrust.defbiaen/lpext.dll?%id& E 8. 1mg 1 . . . . Epomt 2265 °C[ 1 1d:b1adb:r:570068&t:mam—h.htm) In the GESTIS § Eliastgggplpatabase from the FA, accessed on 24 ESOlubility in gym g/L (20 DC) (http:Hquery.nytimes.com/mem/archive~ ‘ wmmwwam»mm»~m-m3ml5flmwfiwmwmwwwwwwmwj Ephrases a SR3 1123/24/25 E Elieeptluwhere noted otherwise, dais;"sis;'eii"“"“; E" materials in their standard state (at 25 °C, 100 kPa) lnfobox references free/pdf‘?res=9AOCEEDDlF3 0E233A2575BC1A96E9C946697D6CF) , The New York Times, August 18, 1907 3. A Dunnite (http://www.firstworldwar.com/atoz/dunnitehtm) , Firstworldwarcom 4. A Ridicule Spy Story: Anny Abandoned the Use of Dunnite Years Ago, Officers Say (http://query.nytimes.com/mem/archive— free/pdf‘Pres=9903E4DC1131E233A2575BCOA96E9C946096D6CF) , The New York Times, August 8, 1 of2 11/5f20109z27 AM c. nvdcwfl-n‘t dwawnflfic (end \-IU“‘ V. I WW“: ——-—- 6. dg 1.0391; "‘23" 1.622. in of nitrates: Germuth. 1929). nine. a,4—Dimethylben- hylphenyl)propane; 1 -p- hetamine. le-IISN; mol 19.39%. Prepn: Meet! at r). ismine. N,N-Dimethyl— :hylaniline. CnHIZNz; mol \l 20.58%. Prepn from p- itained from dimethylani- is des Organischen Chemi- 1961) p 273. By reduction 'ractical Organic Chemistry i9) p 624. 'N(CH3)2 3°. also stated as 41“. bp reform, ether. Keep tightly 31. white to grayish-white, Freely sol in water; sol in nscopy and in tests for noe- dases. lignin, ozone, H301. enylpropyl)veratrylnrniue. imethylbenzenebutarmmine; 1ethylarnino-4-pheny1but- yl-or-(3 -phenylpropyl)benz- 1.45. C 76.64%. H 8.68%. N Brit. pat. 802,723 (1958 to 332 2enacsz— c6115 ; Sp 281, Manzal, Monzal— 1,2-Benzenedicnrboxyl‘ic acid tethyl ester;methyl phthalate; ate; DMP; Palatinol M; Fer- ,; mol wt 194.19. c 61.35%. ustrially from phthalic anhy- :yes. Clark. Industrial Chem- 9 267. (2nd. ed.. 1957) p 309. pl: Cross at at. J’. Chem. Soc 0000113 "12000113 )r. d}? 1.196; dfi 1.1940; dfi lbs. Flash pt 295°F. mp 5.5o :es around (1°). 13pm, 283.7”; um 210.0% 13pm 194.0“; hp“, 3250 Colorless to yellow liquid. d3,“ 1.1362. hf,” 1.4733. bp5 123.3; bp 280—281“ (some decompn). Miscible with lower aromatic hydrocarbons; partially miscible with naphthenes, olefins. paraffins. Limited miscibility with water. use: Solvent for liquid-liquid and vapor—liquid extraction processes. Dimetlrylthiambutene 182.8“; bpw 164.0“; hp“, l47.6°; bps 131.8°; bpm 100.3“. Vapor press at 20° < 0.0] mm. The vapor is heavy. d z 6.69 (air = l). 11%,“ 1.5168. Viscosity at 25" = 17.7. centipoiscs. Heat of vaporization: 93.1 g-call‘ g; heat of combustion: 119.7 kg-callmole. uv max (ethanol): 277 nm (13;; 57.7). Miscible with alcohol. ether. chloroform. Practically insol in water (0.43 g.’ 100 m1). petr ether, and other paraffin hydro- carbons. Soly in mineral oil at 20°: 0.34 gilOO g. LD5n orally in rats: 7 milkg. USE: Solvent and plasticizer for cellulose acetate and cellu- lose acetate—butyrate compositions. Insect repellent for per- sonal protection against biting insects. Caution: Irritating to mucous membranes. eyes; can cause CNS depression when ingested. Not irritating to or absorbed through skin. 3245. 4'-(Dimethylsulfamoyllsulianilanilide. 4-[[{4— AminaphenyllsnlfonyIJnminoj- NLN-dimethylbenzenesulfon- amide; 4-(4-aminophenylsulfonamido)phenylsulfondimeth- ylamide; NI.Nl-dimethyl— N‘-sultanilylsulfanilamide; DB 90; Diseptal; Diseptal A; Uleron: Uliron. C,,H,.,N,0,s,; mol wt 355.43. C 47.31%, H 4.82%. N 11.82%. 0 18.01%. S 18.04%. Prepn: Yoshicla. J. Pharm. Soc. Japan 74, 1280 (1954). CA. 49, l4666g (1955). H2“ Q 302“ @502}: (CH3) 2 Crystals, mp 194‘. Slightly sol in water; more so] in alco- hol or acetone; freely sol in sq solns of sodium carbonate and bicarbonate. MLD iv. in mice: 750 mglkg. THERAP CAT: Antibacterial. 3246. Dimethyl Sulfate. Sulfuric acid dimethyl ester. 1160,,8; mol wt 126.13. C 19.04%. H 4.80%. O 50.74%. S 25.42%. (CH3)ZSO,. Prepn by distillation of a mixture of olcum and methanol: Guyot. Simon. Compt. Rend. 169, 796 (1919). Technical production from dimethyl ether and 303: BIOS Final Report No. 986. p 176. Review: C. M. Suter. The Organic Chemistry of Sulfur (John Wiley. New York, 1944) p 49-61. Colorlms oily liq. bp about 188° with decompn; hp,5 76‘. Solidif —27°. dill 1.3322. nil," 1.3874. Flash pt 182“F.A Soly in Water 2.8 g.’ 100 ml at 18°. Hydrolysis is rapid at or above this temp. Vapor density 4.35. Sol in ether. dioxane. ace- tone. aromatic hydrocarbons. Sparingly sol in carbon disul- fide. aliphatic hydrocarbons. LB,“3 orally in rats: 440 inglkg, Smyth 3! £11., Arch. Ind. Hyg. Occup. Med. 4, 119 1951 . See also Methyl Sulfate. CHJOSOZOH. USE: Methylating agent in the manuf of many organic chemicals: L. Fieser. M. Fieser. Reagents for Organic Syn- thesis (John Wiley. New York. 1967) pp 293-295. War gas. Caution: Extremely hazardous. No warning characteristics (eg. odor, irritation). Delayed appearance of symptoms may permit unnoticed exposure to lethal quantifies. Liquid produces severe blistering. necrosis of skin. Sufficient skin absorption can occur to give serious poisoning. Vapors. alter relatively asymptomatic latent period. cause severe in- flammation and necrosis of eyes. mouth, respiratory tract. Severe and fatal pulmonary damage may result. Systemical- 1y causes prostration. convulsions. delirium. paralysis. coma, delayed damage to kidneys. liver. heart with ensuing death in severe cases: E. Browning, Toxicity and Metabolism of Industrial Solvents (Elsevier, New York. 1965) pp 713-721. 3247. 2,4—Dimethylsulfolane. 2,4-Dimethyttetmhydro— thiaphene 1,1-dr'oxide; 2,4-dimethy1thiacyclopentane 1.1- ' dioxide; 2.4«dimethyltetramethylene sulfone; 2,4-dimethyl— 5 cyclotetramethylenc sulfone. CEHIZO S; mol wt 148.24. C 43.62%. H 8.16%. 0 21.59%. 5 21.63 a. Pro-pd by catalytic E hydrogenation of 2.4~dirnethyl-3—sulfolene: Morris. Mel- ; chinr. U.S. pat. 2,451,298 (1948 to Shell). 3248. Dimethyl Snltone. DMSO,; methyl sulfcme: meth- ylsulfonylmethane. €214,015; mol wt 94.33. C 25.52%, H 6.43%. O 34.00%. S 34.06%. CH3802CH3. Has been found in primitive plants such as Equt‘setum arvense L.. Equiseta— cede and in the adrenal cortex of cattle: Pfilfner, North. J. Biol. Chem. 134, 781 (1940). Easily prepd by oxidation of dimethyl sulfide: Douglas, J. Am. Chem. Soc. 68, 1072 (1946); McAllan et 01., lbid. 73, 3627 (1951). Crystals. mp 109”. bpm, 238“. Sublimes at 13 mm and 90° to 100°. Infrared absorption (solid) 7.6-8.7 p. Dipole mo- ment 4.44 (vapor). Freely sol in water, methanol. ethanol. acetone. Sparingly 501 in ether. use: High temp solvent for many inorganic and organic substances. 3249. Dimethyl Snlfoxide. Sul'finyl'br'sfmethane]; methyl sulfoxt'de; DMSO; SQ 9453; DMS-70; DMS~90; Deltan; Demasorb; Demavet; Demeso; Dermasorb; Dolicur; Dome- so; Dromisol; Gamasol 90; Hyadur; Infiltrina; Sornipront; Syntexan; Topsym (rescinded). CZHGQS; mol wt 78.13. C 30.74%. H 7.74%, O 20.48%. S 41.03%. (CHQISO. Prepd by air-oxidation of dimethyl sulfide in the presence of nitrogen oxides: Smedslund. U.S. pat. 2,581,050 (1952. to Aktiebola- get Centrallaboratorium); Coma. Gerttula. 13.8. pat. 3,045,- 051 (1962 to Crown Zellerbach). Usually obtained as a lay-product of wood pulp manuf for the paper and allied industries: Robbins. Chem Eng. 68, No. 13. 100 (1961). Purification: Traynelis er a!" J. Org. Chem. 27, 2377 (1962). Toxicity data: Brown et 01.. J. Pharm. Pharmacol. 15, 688 (1963); Willson er al.. Toxicol. Appl. Pharmacol. 7, 104 (1965). Reviews of pharmacology and toxicology: Jacob, Wood. Arzneimittel-Forsch 17, 1553-1560 (1967); David, Ann. Rev. Pharmacol. 12, 353-374 (1972). Review: Ranky, Nelson, “Dimethyl Sulfoxide“ in Organic Sulfur Compounds. vol. 1, N. Kharasch, Ed. (Pergamon Press. New York. 1961) pp 170-182. ' Very hygroscopic liquid. Practically no odor or color. Slightly bitter taste with sweet after-taste. :11” 1.100. mp 18.45“ (supercools easily). bp 189°; bp" 83°; bps“ 56.6“; b13132 4.74"; 13pm, 30°; hp”, 20". Flash pt 95°C (203°F). rig 1.4795; rtn 1.4737. Viscosity at 27° = 1.1 cp. Specific heat 0.7 call g '(liq). Dielectric constant: 45. So] in water. etha- nol, acetone. ether. benzene. chloroform. Forms stable coordination complexes with metals: Meek et at. J. Am. Chem. Soc 82, 6013 (1960). L135“ orally in rats: > 20 glkg. Human Toxicity: Skin contact results in primary irritation with redness, itching and sometimes scaling. Urticarial wheels are not uncommon. Corneal opacities have been produced in exptl animals. use: Solvent for acetylene. sulfur dioxide and other 535%. As antifreezr: or hydraulic fluid when mixed with water. Solvent for Orion. As paint and varnish remover. Dissolves some hydrocarbons more than others. see data sheets issued by Crown Zellerbach Corp.. Carries, Wash. Review of use in organic chemistry: Agarni, Bull. Soc. Chim. France 1965, 1021-1039. Tilt-IRA? CAT: Topical anti-inflammatory. 'I'HERAP CAT (Vt-71‘): Proposed as analgesic, anti-inflamma- tory agent. and penetrant carrier to enhance absorption. 3250. Dimethylthiambutene. N,N—Dimerhyi-4,4—di-2— thienyl-3-bur‘en-2-amr'ne; MNJ-trimethyl-3,3-di-2-thienyl- allylamine; 3—dimethylamino-1.1-bis(2-thienyl)-l—butene; 3-dimethy1amino-l.l-di(2'-thienyl)but-l-ene; NIH-4542; 338C43; Ohton; Aminobutene; Dimethibutin; Kobaton; Takaton. CI‘H N51; mol wt 263.42. C 63.84%, H 6.51%, N 5.32%. S 24.35 c. Prepn: Grignard reaction of ethyl fi—di- ‘r “N f0 methylaminobutyrate with 2-thicnyllithimn and dehydration s (:33 of the resulting 3—dirnethylamino—1.1-di-2-thieny1butanol i with HCI: Adamson. J. Chem. Soc. 1950, 885; US. pat. " l l 2,561,899 (1951 to Burroughs Wellcome); Brit. pat. 657,301 ': C“ (1951 to Wellcome Foundation). 1 Page 433 ...
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2010_11_05_lecture_ch21 - I. \< 2 lo \—/ Y c. AO\—\...

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