Document peXEaJyo9vJNM0JzjRav62mj7
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Name of Co.: Department :
00308.41 SO.
Subiect ; trnmm - mm m mmmmm m mm
p. m. p : APR 1 1929
Author
1,
: 4* *, TOOTKTSS
SgaffilMitOaS
Date mm& 22, 122*
<?] I tM-xli-},
Stow is epjHWMsatly little tetelia asefi la this oouatry, aaS little
jSNWfee% of fates use as long m petrolotaa, tepeatia e aafl eoal te
ssefiaots sear their preeeat prices, its eMef eoapetitors "feeing
tcmzol* see tafcl tale, it will cost
fretely shaat 4*3/2 eants r It. to iteofaetare tetralia. It is list*
eft la tit* Ml, yaiat, aM .Drag ssperte at 20 oasts yes 11* la areas, 1st
t*y gweat proination ia this country weala ia all likeilbaefi cause the
yet** to rp tlow coat of
it ia fceliwa that the m|er
oeasaaptisM here is of lsgvt$ sateriaX*
*BEuaagj^^ She prices teles are e&leaiatefi *e* fiats oMalaefi la oar
iitey e& latest JetuEBals,
.sate
SSSif* #*ai* Haphtfcalea ferpeatiaa Qasoliaa
Percent of local tePcatiBO Brice
29.3 2?.f 2?,9 10Q 26.2
price peg lb.
$0,200 0*0S1 0*022 0,099 0,016
Mass
>- S3 *. ls*>
*5&&9k&$m $a*eIwB* tlae**
100
0*310
goat of fstrsiia ysi
&**& gjtertsl 1WWW6W HrTKtf* ssist
im
IS
mfef lOSlffiSS
ar
! e#t, at fo02 sea 1%, of tetralia lis.tetsalia itelasleo of
MttoiiftJMg. ^PfpCjm .
0 0*9*1
tsm
Beport - B80-1002 - A.2.mckafuss - g/22/29
getes,.
fhe yield of tetralin, tfi percent, la what we 'believe can be
done m basis ef ear desalts-..
Site .08 lb. sodium is calculated on the basis of 0 saeeess-
ive mas without renewing the catalyst, the best that is claimed for
niefcel,
fhe operating east of z cents per lb. of tetralin is basal on
report of H- A- Bead, file M8O-10OS, Jan. 4, 1026 for production of
formamid at 7C. and 30 lbs, p.s.i,, where 1.6 ets. per lb. of formeaid
seas calculated. wax tetralin at 2603 and @ lbs., 2 seats per lb, of
product is aensidered a liberal figure.
Eeaulta iadieate that erode naphthalene ear be hydrogenated as
Will as para naphthalene with sod lam present at start. It is probable
therefore, that shift-gas hydrogen weuia be well adapted to this process.
la the pwe ess its described by juraess below, 73$ of the
hydrogen delivered is lost during operation, bat it is net believed that
this is a necessary less under modern conditions.
She literature abstracted below will give the details, from
this the following uses axe elted, all being in competition with cheaper
materials.
Seating fuel in cooking apparatus, go. Sotor fuel (mixed with aleohol and benzol), niomiaatlng fuel (in kerosene lamps). In shoe polish. Xa polishing, waxes. Solvent for resins. tars, da. la varnlsh manofae sure la paints, enamels, sad paint driers. As a general turpentine substitute. In laetuer marufnature, in the tanning industry, in dye manufacture, in the explosives industry, for pharmaceutical preparations. for absorbing benzene and S3g from prude illuminating gas. for absorbing alsohel vapors la certain processes. for water proof Varnish, for cleaning textile fibres. in the extraction of oil shale. s mu m.. la extracting1 sulphur from spent oxide of the gas industry. In production of disinfectants. In the perfumery Indusby.
nr* laaiWB mm mmffiai as s mm or wmMus
VZmxa?, 8*231
Ms h*a bees swamtestured by l^ptrtBeaatles with si catalyst by
fetralia,
Basils, ilw if17. S. Sehreetar brought tee presses to
HMsd emmm m a aestlsaewe operation. see b .E.p .* $9012 &a3 Steels*
la order to parify the istphihaiaa*, Sohreeter renewed tee poisons by treat*
neat ef tee fused evade naphthalene with finely divided, easily fased setals*
ffce naphthalene, se treated, .is distilled under diainiahed pressure dlreetly
late tee h&Q&og*m%lm eaieolsve, teer* is provided a agitation autoclave
for eetelag pressere ef 40 atmospheres (teO tea*} with eeairlvaisees far diatSUs
teg Sit wetter diminished pressure end for sashing la er tenting in awe
efcarges ef asphth&len She auteelava contains stehsi as catalyst and can be
used ter nestis without opening er renewing ef the catalyst. tee hydregenat*
tea is eseteertKte, so that far earryiag eat the reaction a eupply ef heat is
available* After reaching the tetnabydre stage the hydrogenation rate slews
up as that tea eat ef the roaetioa is easily noted, tee totralin tom& Is
then 41stilled eff under diminished pressure and ware naphthaleas added.
(tee ehaage te the Biesa" follows la another eateel&ve with fresh sat&lyst,
er another supply ef eatelyst}* tee tetrelin so obtained is very yore, it
eeatalm aaly traces ef naphthalene or ef higher hydrogenation derivatives,
whltjh, however* have so offset oa its sees*
Baring the war, tetralia served ft heating eat motor fuel fer the savy.
It is hew wed ter heating purposes {eeeJciHg apparatus, household stoves}
sad ter the operation of aaiemblle me tore* it haras with a acn-smohing
elear Qtn in herosene lamps end adapts itself for every motor use. it has
been wed is set ineeasiatwahle gnsatitie* m a dissolving and dilating
naterlal is tea sh&e palish mi polishing wax industries as well as Is
lstuer manufacture, tP*<*ahyfinmaphlheleee is -used similarly)* Baphihaleae
has heretofore bees a "drag es the jasshef, ee that sehreeter*a saeeesafal
teshaieal prodseiiea ef the hydrogenated .saphthateMKi eases as a sew and very
premieteg prustieol application. - terse preduets are mmteetuned by fetralia, I
&& BH*, Berlin is a teetery at hessian (ink*) which has reaehsd a daily
jpwdeetiea ef 190*12 Sean teas (100,089 to 120,098 2%*J 229,402 te 824,880 lbs,| 119 te 1^2 ordinary aagiish short toss) per day (is 1929)*
'$9r jpiisiPt year# theft jhsto h#t* hp9hh*&*ss inyostigatiohs 1 h&iig
hasktkaleriie
hy&raaarb&ha to
with Attfln , by alksistleru
itojjfc" for use ae feet * m$m` &* bat thSft* ISMliMf JtfiM* to hate fossa
* im Ut
eg tetrails,
IflRlI mtr tb* MW *f a#.ifi^StJtfesst.eff for astoawbile fuel there km been ti$M8*& on the atarhet 4 sixtare of
Ullmann, 9-431
(SWOB S*e 449 OH is a general 4ia04BSi4 Of hytoOgaESfciOH). Sehroettor werkeS alis.8 with WiBtBor (BHP S86852 anfl 888488)* The beat
0*wSe mphthalass eoat&ias 026g of seljrhur. she teehnioal prObles was to
sesewe the eatalytis pOisesa * predBOtion m a large soale, after sahreefcter
aOlwed the poison problem, efts bf |Mr & gehreatb, IS? 5S4S62 and 324862 where finely (It UM or easily fasafi natal was used, or fan** earth (PSP 8249&1}. Similar praeesaes are the pitt-proeess of the parson oil So., Praseh process ef Standaril Oil Co, and BHP 140717 of SeiehJer & .lasso*
Is profiaalag tetraiia, the catalyst oan be osed SO-50 lines fhe hydrega mot be eopooially pare .
m* oxide of si &s. as eatalyst, see Aatiea Seaalleehaft fir Aallia mhrihatiea in Berlin, PHP 298541, 290553, a4 381275.
Por osea of tetrallu see Stmatstoffe, 1926-185, ip to TFlBsana, 8, Oil, it ahou.M bo stated that Sooalia, instead of tetrails, is ased os illwmiaatiag oil and meter fool, leealin eaa be parifled with lig,aid SOg {ISP 210781).
ho same soapsay (sietrslia, .Hub#S.} hydrogenates aeeteae to Isopropyl alcohol, and phenol to oyttlohescaaol (hswlin), the latter being esterified to hexalia aaetate. f the three great applications of hydrogenation, the first is fat-Jsuftraeniag, the seeoaa, tetralia} and the third, is the prodnotion of aiedhei frea asetyleiie {1st te ethyls & then te aloshel), {or hjaregemtion of asetalSehyaa diieet to aleohol).
6,A, 14 (192} - S281J ROW, proa, SM., 23 (1920)- 437.
There are 5 hydroaaphthaleaes possible, all known, only "tetra"
*8
sprt - 880-18(3 - A.E.Baftefia8s - 3/22/29
**8 adeoa" are owed. fotralia Is as exoelleat solvent fax1 aateral resins* oournarone realsa, ladeae, t*i*s, wares, oil, fats, varnishes, driers, **,,, lit alseible ia all projaa^feais with spirits of turpentine, xasia all, eeal tar, aSMm&l oil listUM&aa, trleJ&erethylene, amyl aostat, &. ska asia *e ef tebr&lia sad deoalia is as solventb ia lae^aar mi varnish Industries, fSteats &t for use la tanning, dyestuffs, explosives, and phartt&aeatiaal preparation ladastries. "Easeno ef tetrttlian is tetrallfc $3m eyolohexanel, anevea better solvent m varnishing there is danger af my seat baiag disselvet by the #nbee0aat seat. Ma is prevented by ass of totraXiBHmt** ia tl varnish (and by ether Bethels)* setr&liBextra ia tetnellm plus desalts* Of 88 resins tested only three (eop&ls} mao insel&ble ia tetralin. sealas fen alsehel varnishes are not soluble in tetr&lia.
0.A., 18 (1021) - @28, sreanst, 0k*, (3920) - 39. then tetraHn is digested with 1$ ilOlg, about S0 of a aixtare of oei&hydre&ntfcnaeeB* sad otai^rephemnthrene is obtained*
C.A., 19 (1923) - 2289* 8. lay. Oh.* 38 - 389 (1928)* Bata are gives to show suitability of tatralin for abaoxbing
benaeae, benzine, mi QSg ant of illaalmtlng gaa. Pries and volatility are satisfactory.
S.A., 28 (1923) - 788; , Ag. Sh., 38-10X9 (1928). fetralin and deealin are shown by vapor pressure eurves to be x h k
eseellsat li^aiffi for absorbing alcohol vapors. 0.1*, SO - 274S (Xf2()j 3es u. yasssc ., 89-493* fetraHa is shows to be bettor than seal tar wash oil for
shrubbing hemes* eat of liluaiBatiag gas. SO* . 18 (1922) - 841) #. Alsg, 0h., 34 aufs11921) - 494. Agitate aelluloi a with t*trails, deeslia, or hexalin and it
dissolves. Add a fatty ell and a eeliei&al pigseafe. Result is a water proof varnish useful in mHng buttesfe, &*., or waterproofing yarns or iasabating copper wire.
C.A., 18 (1922) - imi inn. 428 - 1 (J.022) - sehroetey. fall washing details for afg. of tetralin at 180-290 and 6-15
acts* with ai. purified by its 30gH dariv.
m&< e
Resort saaiss2 -
~ 9/22/2
s .j u , is uw * m$ mmm * m. mm* awn.
fetratta has tfen seStfeat pMpwUm of as mm&%U hydro-
tawbes* dseslia, etf a tslaspal oil distillate.
U* is (19245 - S90* $mmm, 4-681 (19225.
s?trails eaalslea la m&Q by agitating it -with 6# Ha eleata
Bolstiea* this is a uaefttl fat and ease reaewr for t**ctil uses;
alas for Kim boiliag eottea.
0.A., 34 (J920) * aasei w%e. m* 2 (1920) - 2280*
Efce flab osier of shite aael files made frea totnOia is sal
due to tbs telpaXigu
6.JU, 14 (1920) - 8&&8; Rtf-ten. 2feg, 26 (2926) - 231.
MffissatiaB of tofcralis Is f&iatt* aad aaasia aaeet- slow firy-
lag, ^sagging", sad "oarfealai^ of the filias, asfl softening of tfeo
mSm ooats* fhse say be everooss by additioa of naphthas sag alaes-
al upim. 9talia pas 8a0 glees a glossy mss. s mh bs Is tnoa
betraSia hats as goal a gloss as with other aoltoats.
6.1*, 14 (3920) .- 26001 MV. eb. lad., 29-192 (1SS0).
Sydregoastsd aapbbhsleaes art saperler to basseae, aaphthas,
yolysiOere altphabie deritattves! sag other tarpestino substitutes
Is tbs ssaufaeture of lasgaasa and tarnishes. betail* gitea,
0.JU, 20 (1920) * 2221}
<ft, 9-149,101 (I90).
fetmUa yielded a 19,9$ solution Is extra?tlag oil a halo,
while hsmel yielded a 2*18# eolation*
0.1., IS (1922) - mZ\ 0h.2tg. 46-897 (JM},
Mixtures of beazel, tetrails, and aXeebel are reoHKeaafi .as
gaaoliao substitute bmmm of their high beat value pm salt yoimo
sd tbs large predwetlen yoaisifcl*.
e.i., is (i92i) - tat) aw.jMt. ch*, 22 - fis <1020}.
Review of literature of $ of tetraXia, be*
eju,is (3924) - am - s a m* sa-s-ps (1924).
fatso as above*
e.i., 14 (192)3) - seen seat* #u ztg. 22-60 (its).
Beaalia is ore libs turpentine than ietrails.
7 sport - 689-1098 - ASUiaeite8aftLS3 - Z/22/89
O.A., If (1923) - WfS| g. 11 A Color @u mm.. -fa USES)
Review #1 f&* & uses of tetralia, Ac.
C.&.. m (192d) - 24931 M* Byestaff. Bept*. 14-346 (IMS)
lrep, prep. and ssea of tetralia &e. are gives is molt detail.
@*JU, IS (1924) - aS6S| BV. ParfBa*, 4-394 (1924).
Possible tujea of tetralia is perfumery industry.
0.A., 14 (192) - as!; Z. Beat. 0. & f. tod., 40-421 (1920).
toxleity of tetraMa. it reverts to naphthalene la tody as
say color aria green, Oat is sly mildly texie.
G.A., 16 (1922) - 214.1? dura. Age.
20-173 (1932).
Bevies of ag* 4 ages of tetralia, &e.
8.A., 14 U92@) - tMfef 0m* 2fe. 87-779 (2920).
Tetralia la a good solvent for ralter.
S,A 16 (1921) - 34101 Z. Mg. Oh., 34 aaffe. - 366 (1921),
la proparlag rubier atifevtitats*, fcy dilating the vegetable as
drying oil with, tslarailia, the reaction of this oil with SgfSg is
materially retarded usd vtsisaee diminished, Mineral #12 also does
this, hat totralla hits the advantage of aixlag ia all proportions
with way drying oil.
0.A., 16 (1921) - 9601 Seifoasu Ztg., 47 (1929) - 937.
fwo types of shoe polishes are In use. (1) soaps ssnlsifled
with water to a paste and (2) ells and waxes dissolved to a paste
in terpentine. path types taS tetralia, with amah improvement.
Ho o t waxes can he mods with tetralia, 16 recipes are given.
C*A., 19 (1926) - 3603} Paint, $fg. Asm. ire, #848 - Ssrdaer,
Hexaiia is only one of the new solvents (hacahydre phase!,
tetralia, deeelia) that has cay pronounced action on nitre cellulose .
Ahstroots of literatase given.
0.A., 17 (292?) - 1W| MMI, h., 3-330 (1922).
1teuay selves te have he on tried he extract s from spent oxide gas-
yarifying material feat they have heca too expensive or gave a trry
salphar. .Tetralia dissolves %$ S at ord. tea, and 4jS at M0S. It
recovers a eleer yellow sslpfcar team the spent oxide. The aside is
$m $ part
* sfn/m
ready m am again and tie teiralto in moral. 4t 14 f3S28) - 8342} Jtotofa* 2%,:, tt-lfTV flttf)#
fetraito is fully aiiKlfale with all euivmtB aad alia of tfae to*ij*fa totestry tot not fully witfa fayprodaat turpentine, (Sa sad 98^ aXaetolj also dissolves '*#11 resins and restoalas, exaep t tfae alsotol satoMe 0803* it i sot adapted to eatoJt drying laoa&era, $<# a resin Itotser Bade witfa ttoptoitoo 4x4 oi la & Kin., *Mlt %ha ease witfa toto&lixt dried to 2 faro. it a*y to used la Multiple toot mark*
efaosu m .t *,, s (ms) * i*. 208,.800,800 Xto* naphthalene attNttiUy predated to dnerlea. tJeei for ^ttfaalle anhydride & Malted output*
fao use of tetmJ&a afaread as motor fool and tutoenttoe gfatotitate eas fasva m interest la 0,8* 8 wsefa greater interest to as ia its tola la 639 staffs, its too ua*iiyft*egesated sueleoa oats very nosh Ufce toasts!., taming too mm derivatives, toelading dyes. it is very griftafaie that tetraUa eaa to produced la uvs. at a prise allowing e*jtttiB with faeasel. Sew dye effests ptosifaly way he desirable, wm. at filially greater eos* then tomel* Only pure naphthalene can to asst for faydwsgetotito. Ordinary w^fatfafatene, if rtofeto with atm* B%0-4 la a aorta?* gives a red or pin* eolsr, If It toes net, it is pare totogfa-free frea tfai#~aapbthe as,
X*r the parifieahiea tfae totralin 0sufa.H., Barlto, uses faltore* earth, eedlam, eedasdd, &s. She aapfatfaaleae after treatjaent is filtered or totter distilled to vaauss, direst tots tfas av&wterm ms hydrogentea at Si# 4 18 ata. sydregoa atosrpttos is sapid at first tod Utile or as heat is reauired E3tfaorate roastisa) * Sapid agitotiaa is seeossary.
Ussy types of autoclaves ere usahLe, bat it is advisable to esoleso stirring goer and asters, sines matfaetua of lt| totralto toes up 28000 0u.fl. hydrogen to preparation to ordinary agitating autostores too satalyst is reduced nltoel upon fsliars* earth, or niotol oxide froa
1m *
mwrt * Im*wm - a.e . Etofceatosa * S/2S/29
aietel earheaate (sa follara* earth). latter is olaiateS fee have Stahls the activity of fe.mer, la meat patent ef fetyalia, asub.H.,
sat la mm eheayly
After lees of activity, the eata3yst sa "be regeaexafcea with little Siffiealty.
26,686 etuft, of hyterogm are uaefi fee 1 tea tetealizu Catalyst ehtofes sM paLfleatloa easts ta not be heavy. ser pmetieal purposes feotralin ssast he eap&hle of preflwtioB a* a yrioe cotsparable fee that of f&al ,ts* hemal ass lama* ttoa that des&aaea for jsertcaa turpsafeiae la Europe. traea are give* as la previous pages. If It la ehlarUaatal anft the ehler aemv&tive eftadsiwea with tstralin itself , a go lahrieattag ail results.
ihr lyewtatfe *m 'Bam, J.Soe.Ch. IBS*, (352.6) 14 - 241 * S* fetrs*y4r0^5hthal9ae-2aashth03. is a iisiafeetaat, the ethyl ether ef tetsahyilseaafhthsl has valuable 4 iferovts
HOW, jUS.G.I., 14 (1526) - 2411 the m& Syes fern tetralia 6 iffar oeagiserably la stole teem the eorreapoMiag ayes from aaphthaleto Is this way, the tetrahy4rea mphthylaalae (as susAe from tetralla#) ast its derivatives sight well prove useful laterjoediatea*
A. M, Eaokeafasa
