Document Q8KJ6LnE052wXgNo3kN0NDKv

E I. DU PONT DE NEMOURS & COMPANY 256 VANDERPOOL STREET NEWARK, NEW JERSEY Copy No. / NEWARK PLANT PIGMENT COLOR RESEARCH REPORT t'" c r V :> fOI HU File (22341) File (22341) '/a* Siegel fwt'Vi'tn L&boMtwjf (PwX^S)' Serial Ho. %>i KR.54^21 / HEtfARK FUNT Progreee Rtport tXtbSI !AL*FHEE IBHUUiOCXABIHB miao c o v er ed * Aim, 1931 - msmm, 1953 CHARGE* A-II-C-257, 279 S0J3OTJSD BT* fA9WS APPROVED St 1 Dm SUBMITTED* JtBOS 28, 1934 DAIS ISSUED* JULY 13, 1954 DUP050069804 tlM Hgneats Department used to naricet * aetal-free phthalocyanine the preparation of netal-free pfathaloeyaniini directly front o*ctyaoo- beasanlde and from |gr trsatnsixt Pith antinciay, *f been disclosed (0*8, Patents Hoe. 2,000,051 art 2,000,052). In the latter patent, awonla is and alone with Bhthollsdds* It Is further dleolond Mot asy also be used, since the anhydride alii tons phthallalde tgr reaction rtfcb ansonia. The yield of netal-free pfathalooyinine fcgr the process of either paint is 34G0f based on the starting phthalio anhydride. A norm approach to the synthesis of metal-free phthalocyanlas tgr the phthalio anhydride-urea process invoicing "in-proceae" rednsticn nae investigated. Metal-free ood yield has been **.<"* fay the nae of ** *"*^y^aty^yoie^y^^^Cys. e^^os ai^Bis^^enaess^e'--y^^u^r^^aeoieftei^yy .se,,^. y^^v^^^y ay^^s^^,ye eyyy^^^eeyse^^w^esi e^j^, ayss^ar spasms ay*a .'Sesassstae4eyfcneys wtiinMi). tn ar'ftjttMrttlon with f|f ancillsiST "gents in the ynafrft'ac** anhydride-urea process, k hsasadeeaohlor metal-free phthalocyanine has, likeid.se, ben prepared, Caloitm nwyn<^ h, been synthesised tsy the phthalio etthplrlde- urea oroeeee in Pom* yield fear the use of onmdfi redneina aaenta.^me --^sn giae *^yavTyyyyy ^ee*e gvsy^yie |g,s*-yy^^-- u^yyyy ^y?s eye j^snseeiev^y .as ey^seses^eiaeg^ es|^goeaevrve e AtliBlfti to lynttnilM gom Igtrlltiintigl ph^iiin good jdgl4 Wsi^sf fecseHe^#^, y^eJ^ehtysk,ohssvtet^lyI*Sniey aM^eelvsyMa|^^{a|^n,,, 44M|^Q^wieeM njeewie w|a|fl yang y^^M^y^yk llHlflllf^^^eca--- n^wi n blending to antoh OiMbftO yaytapp HTTmyrnai Xt is tMpt^yyod -* *- the use of fp^**"*****111 <|>,1|"'|i^|i<> in ***** ^H.,aP|y n.y1 gg MyrlVt^yy jjj tMtCl-fTOO f> Synthesis tgf the enhydride^orea rente in patewNib^ef- DUP050069805 flila jKthylrtrtyawtn bgg 'fyy^ IvlfrhuF't'O bbOB bOdt by tho nriwrirtrts.ni'awisiiTiriint wwitf. twt baa boon aynthMlnd in <*< 4w fwm by the ifrfetifrifi* *fty1r1itiir otvo xmsti) .in troy^ttyny iff ib-flyt j^yf 2ft3J5 ortsie ea*tsetnaoted yields f*g phoyl* bydrtMdTff* rod din a^byfl fifwiryiff,i*ift*f lyH^pootlvffly^ oo yro^tioiiib yyfffcy ia tito oynthwili ftnjii,-yf<i evrittm |^gg wod on tiff octal iDspcini ?Hffthylwtot-vi ff** appearsmw mi OS^s h o v to ^p b4h o? t h^>Oot> a^weft<wr o*v i oaffffeeaottivitiosppp,eF^<p^^^a'^ i^rpMedduocoingff awgewnt fat* those w iw w m . ^p yjLoild of j%tbo^(*o>aoyyioffo>*iTw by Olio |y*i toots buy __ ___1st* oreosod ftm 244# to 3X4tf (otuto autttrraocotted) using BBT in the oyntheels. f^lHawWlpfRtOhO`yaPBOwfcjflHmWHiSllISOT^ HHBa^^ 4WT1^4HaW*PI #1iOMiiwiOMTOg1IttSUI eMfffeActtitviVe^i.a Twfhf^a^eg tUft Of WW.7 (Lorol tt-* ^" jyTff^**'****^ ostbaorylsle ooffKdyMot1 m Ctobon) dispersing agent, sad f&mm 441 (2,6 di-tort4Mfcyi p-erotol) on dooo nob appear to offot any gneot advantage. Calcine abide 1 o opetlor to > owh asV HBrHiMnhdVHrlaSiSH S1MH4fliHnfl^pr~i ^*W4p1^af^tiap <4N4 SMmO^m^f 4k4 ai*4aa*1t namgzwmM. titf ^^a<mm. 4bf order of yViiti'ffi of the reactants fwi the of o^itloo do iw*. Mtttrijllly affayt 44 yiaUia(^f ^ 4HSF^y^H 4^H4P^aiP^, 4BH0^^" p ^ Ttrlfflif ^>14 hobs bowa ttlod so tho , acetate, sulfide, sulfite, '*& offootlvo Ob oxide Tn MMMtfe. (uaag. no r*4ha1(wwiriw fontttibl hlUt OCOtfrred Ot **1. ttooo foraatlon in othoro. nwly Hbyjtfy jSM^ngypjiai y |^y OytdllOiiSOd ill ICOf yfoUd (ibSOVo) tjf n tooto to 'boo stoiiod* Cf oil" tho o^^h o^iHMttOogbiiibh tondb <q#*baibi^bfcgL ao o ^s Hoooooabg'oi^l oh pO^BW HWHaPHS^pHiHIPBfcH^HHOHPOH^F HrHP p^ a (^HO ` 4a Jbfrjo /Wornaana fillxAKiMma DUP050069806 3* . oi .wlohlnrihanstmm aiililnwMwhttnlw ib . amtI linivthlftw IflAO. n po3ypfcisyl)* the laat appear* to be the at desirable, insofar aa it otana to bo a etyatalliring advent for the HfPC* In no s u m* however, boo a yield in ifyttff ot 3S$ boon obtained* it^drao --p--? *tiyi^ fyjai Bewport (ex flwebal i^pgopi) ou mod In tho ojntilwiol * > Yfl <f*dv q 4C9S .M^oooim jbftbo^i^yBiP^iTw naeo obtained by tho moa* benoaono proaeaa osint ospsolts Mtal ponder as tbf t*io ***fi wrfwf)t 3& koroseno, nednooins phtHol 'WtyoTiHIno nas anhydride process in 17*9 and ylalds, using p fittnllBiMiBlfiBe miyd>ft4^mly, y i^wi4m> rnmnlft* Seaport) nee mod aa tho note! source. filotlqrlon ' ^WnjpR^Pjps>M(BoSAMbwipl**MvRMPk <^^mPm^njAwoWajad4JpawtmjjJ waaUmpmWw^Kn&Si* -v.VtwWoor wWL^ta^^Wwoamw ajomaaMaM"Jnp^jnWmP^m^ww- wM'.hyii ifli mm monavod in 43*i9f yield mlng > and in 17J& yield in tho ` of tho the m mti di- ohloride (an to bo tho Tmthon attempts to ^mpy*"** the yield of mapnwina phthalooyonlno tefe not boon OOBOOOOfbl* tfrriywiy't ma OdLfOtO Qftd *^riftwb,,*T**,4p IWNNI effective ao replaoetnoBte fop d5 ethyl obotrloffl'ffw (SET)* Sydoudno lulfsto tea mnM effective. ^*t"n<* lam ao ***** BBSm **** m adiunw to bo iooo doolr#>* p *>** bonoonoo ao a synthesis fop* .ssefC under *b7 conditions of toot* Arsenic trlojdde, ajpoonio |aiit(iililii| a*^, niimy trlohloirido did not aoifo ao anoiliaiy ****** fon tho oyuthoaio of nafnooim og* *ai*<* 'yhthalo* oyaninoo. tonm&a txioaddo. temnr, bhoe mod in a oatalytio aaonnt, m a 28tSf yiold of natanaoita phthaloeyaniBo. 19.3 Tn pM-.Kai nwyn^nt* vwo pcopaood by tho fboion 7% of thooretioal yiold, rospootlvoly* ftUwniitiO to dosotalliao thooo phtbtil^oyifp^fiiwp by ooi* .xnotlon of a ntjor poyticss of tho **brw^'Wo 4*AAa~ .1 ITiii1iiiij ii1m> lythl*1 **** of dlohlog*tin phUtalo*1 eolwxt f^* thooo Fbthalociyaninoo tdth goonoot to tho ohyoiooX tdioyaoiMn** of *h reaotion olomr* With nnoat to tho lattm* MHa^ftiO yWT?jM^tr*i^8y oB^ytfflTTO too reapootim ?TMflwqoiH>wrt7 Moblor-tin t4 wg tho ed yiold of 72.33C of analysed for 9m yield of 68*9P. HgM.1y |n Of 6Q9C A (thooxy * 9*6ai}. A repeat ayntheala gwo a DUP050069807 x * 4 ** m tMamDoi, iw>aiii Aaiji. Bfeai<w 01* fawpoui iwiftA* rrrspfint <*** tin aMd^ffifftr*T\g Qfd wpt iwtifli1>11j piwist tho dwtnoilM) of rtflffltnt. trlalfl ft# ailiilI^W tMWal jj^, f P^A ^^p *S flm vmeAxu&F't>1 Aia vkiii) ^P "^AeO^S gf^^P ^#^^^#Ppap^O^^SSF gl^e^OOP^^^^A ^S and ooak m* sr397& Ana green and weak i* aljfca phase no ^lm%TmW^mBg* iW^mmMA%WyHMl">;^I (OCraothonn)* tDomo siooIlvyahnt*crtriod W#' JMKLi^^^ClfcPyX*-"JmI f*lWMA#Nib *Iw* *mk**pmrk (bat* jfc,K^1rtw4^,y)|^<f ((%rOhBt) r* t. 10 ) A* PC OX Ootaohloro-ooRpor jdrthaloejiaoiao a m synthesised In a onto extracted yield of 92*20 ant a m inreatigated as a possible blending antertol tor ohlorinstoee CPC or U/CFO to produce a ehade eqtjlnlent to that of fatiO^toM pbthalo- CixolVBirt- of wiseuftp of both CP/CPC a"* 1B/GFC with ootaehloro- CPC yielded prodmte prcHpreaaiyely' waar Alth inoreasing chlorine content, tad w^itmiiliriilir milrit cM 4 11 . CF/GPG !* iniiiinii thin ty eoxwSP^S !^P1^f ^PPB*,w vP^tf m mmW.^MPvP P ^P^^P^P w immg ^P^P ^P ma m^W^P^P ^P IBP '^PP^SSSiP -PPPW ^P'^PS* OP ^^pp porting IB/dO blende. In those o mw Abere tbs jrodwte appeared as groan as, or than too alpha or bota phase metal-free > and dollar* LUbbk Lo o * Oo-oolnat ntH M^wip of |pflySftpy (JpQ tfg&J} both CPtrn and LIBB//CCPC yielded prodwta weak and d igalnat too *etal-f tandarda. too CF/CPC blert# i and iurrt lotenee than toolr An 13-type aystheaie ooriao using dp# 30# 35. 40 and 4$ and pacoaob fAtP#IS li^pg^Q^PSPp "Aw /t.t>/f^PlpP *fPi PM# PWf^iSnSHilaM*e A ^KMMPwgw^S PwPAS4P^i^Pae^^t^iPa^^PiSWSg 1ft ad jg$P^Pa^Pv"f^t^fl*BP&) *Plddd JtTmO* dad^tPt*t^ la Maft plaid# groan, otrong and Istanaa forsoa Bto3Qto0 (lot 90719) atandard# and AtiMg and rod vonras BT*297- (lot 373)* ^^jprtbaaaa ndtog 50, 55,t60d5^yl pwdootof i4-CFA ylOldad in good ylold and on tho groan oido of All tha pc dial# mtoo 6,5 nf* _p_a_y_^_s_if_tt nrigi a m 6*8 strong# groan ao4 anljp a traoo dnll KM97-0 (lot 373)* Menophacnd. ooppor a m syp*#tipi tort in 90*3ft onto as* treated plaid wtoff otasiiird bofftfimo ^ntboala# nolng 25 m ittfhili*F r^fwdwdo obtainad toon too srodost* flaltood bar irrtTorrti tnoriol 1;1CttuiiHdoalroSadSlrJ (lot 373). 4 ooya*^rr-1 ^t** bino# {OAoondbljr too wital ~~rras ^wyantnr (aaltopaotii to a diatlnot bluo), a m totalnod in onto oxfcnotod jdold of 149( of theory bar the nso of hydrogao aulfida gas DUP050069808 effective* In eas series* the Mantaatt Mrs heated to 195*0 tut then the reducing material was tMad* Zn another tardea tin reactants mm heated t 125*0 for aa extended period* to for* the lndnophtoolialdlno (I& recipe)* I wot then the organio reducing agent was added. Inorganic rednotants such as | oodiia hyirosulfite, ootiM sulfide or sodiua thiosulfate do not appear to imi iUMCiLfi wiatr q o in IpIo b i o x m# Attenpts to prapaM octal-free phthalocyanine directly by tho ureaptathalic anlydrlde process using orgaiio reducing agents sash to dlethylaastriaadne, ^lcIgBylawine, tat Mt^ltlocMndne9 pm distinct evidence of color* although laly in trot aoounta* AdnMw&e of *****1 * * itbMdCi area* twuiti mlvbdate. *><* toid* tod antloony wttl ponder yielded on acid-pasting t product in approadaateiy XGSK yield tat tentatively identified to aetal-free pbthaloqyanins* A control m without antimony octal powder yielded no colored natter* la KB aa t reaction solvent, a yield of approximately 20j6 Mt obtained (credo ex tracted! tern antimony metal etill pretest)* In kerosene roaotion oeditn* pelletization of the prodnot was observed* Both tatiaony oaddo and antimony sulfide mt o not effective in this eynthesia. An analogous ayathecie in triohlorbenzens using tetreohlor ytAhaHa anhydride* yielded a product in 16*85 yield tad tentatively identified at polyohloro octal-free phthalocyanine. A series using tatiaony wttl (20 noth or finer) ia increasing quantdtint for the aynthaaie of acttWrot phthalocyanine by the pbthalio anhydride route iatlotted some yield Increase with inorettod antimony usage* The yields* however* were only ia the 10*205 range* A low yield of rotal-free plrthalooyanine Me attained in a anhydrlde-urea synthesis using aMM-eeay w^si precipitated frea tn antimony chloride solution* Attempts to preptM aettldMo phthalocyanine by the phthalio anhydride- sst (in TGB) using oleic odd pita antMony avttl (a bydrogen sourca), antimony ehloridc alone or with antimony aetal* tilioa .gel as a oaialyst, or *Mc*BaM** carbonate dun aa catalMt* were act successful* Saie distinct evidence of odor formation (by acid-pasting) wet observed ia the cate of the ran *.* .<wrny .aettl end The nee of antimony powder ia 0onlinetion with ansoolua chloride (presumably t proton donor ia nolten mm) wee lnvestlgatsd oa a acaac far tya thesiaing metal-frse jirtlalocyanios by the tnTiyrtrl ito*iirci prococa* This getfloo sat given cnccniwpag recuitt* mt use or tactacwy atiti alone iavaritiuy gives a lessor yield* Acid-pasting of ^0 crude extracted (KaOS tad dll* %Kk| 5t*9d of theoretical yield on thia basis j attsrial indioatea a synthesis *<*14 of 42*g of thaoMtitai* Analysis of ths ecid*pasted aaterisl showed it to eoataia 69*755 of a blue notarial preeuaably awtel-free phthalo<yenine analysing for 01S6 satiiaany* sad a quantity of ianrgaaio aatiaony* -The nvoi sn aeld-psstod **> hydrochloric sold extracted yiidd is* thsnfOM* 29*g5 of thaoMtlcal* Bassss aaneatua ohloridt usage returns a lower yield* Idkndsc* the net of nsBordm DUP050069809 chloride in conjunction u&th antiaacy aetal returned a hitter crude extracted yield than did sstlsBuy nstsl alone in tetraohlorphthalic anhydride condensations 147*935vs. 35.935) in product n pdyahloro netal-free ptofchalocpwnins. phthalocyenlM^ froa jtothalio anhydride (eniJjaony aetal plus anaoniUB chloride nethod) in 29*035 yield* *aid-pasted, and hypoehlorits treated, rubbedws weak * green and tn intense *gainst#,phase scfcal-free NN04N9Ntfa ("ifettastral* Fast SELue 2 prepared gt Orchafrc* jfcthalonitrlle). Tbs solvent-allied counterpart (net bypoohlorit treated) was auk, green and doll* Antiaany Mtal-ensKulUB ohlorida syntheses have yielded products analysing -$ fnTtrieet Inpur* Total 35 Sb 35 Sb in crude Crude purity (35) Par Hold GEi9MriBdpaK&HJN8odClBda in crude extres-s---o---d--- ma"sm mmtlM ML,, lltestllaal U 62*235 60*835 11,9 12,9 16.9 18.3 35 Sb in residue after 44 0,32 4B 0,32 83*1 81*7 51.7 49.7 35 Ob in reeidue after igl&EdttlM.,,...... ,. 0.32 0*32 The analytical data suggest that even the iapur crude products aoafcain insufficient antiaoay to b accounted for as entiaony phthalooyanln* {SbCIPC analyzes for 18,225 autlsour)* Either isid*outia> or consentrated SSL extraction yields a product which is essentially aotlaoRy.free (0.3295 Sb) and uhieh appear* to be metal-free phthalocyanine. Tbs aeld<^|wiitsd products (not hypochlorite* treated) were equal id etrength, green, and dull vurcu "Mona*tr*l Fact iLuc 0 fa-phace). The solvent-willed counterparts (not lgrpooblorlte-treated) war vs .weak, Ml and green versus p" phase matal-free pfrfch*1! *> (Orehern manufacture ^^phthalonitrllej eolveetttdlled)* The yields of 51*7j5 and 40*735 of theoretical reported above (based on antimony analysis p***wd| its presanes ss SbO 01) were esseatlsliy oonflsued lay extracted M*1!* ssndysss* Actual yields, ttwiefcrti %nre 49.935 *** 49*235 of theoretical, respectively. A pure yield 54*835 of theoretical has since bssn ob tained (hither urea near, loniwr reaction Has}* Variable studies indicate that 1ever yields are attained at 175*-185* synthesis reaction teWDenaturea. and at snrnnrlTiiiitiilt 210*6* iBoaniiai nitrate jLfl 3jCQU|I 4feiNU& 4flBBK3Si*tBi ^^LF^pjyd[(8g QKfett SfittFCMMttMl JftKB (&SS '&2j(ijfii|!Lfi3pQi8 bensflm} gave an entrusted yield of 49*835* 'The 'use of kerosene as a reaction snwa^t does .not remit dispersion of the product md e^>ni^|e|vil:0 up uni caking (final product a single solid luqp)' of the eyntheeie s k is use experienced. DUP050069810 A orate entreated pishd of &*$( astal-Ffroo jfcthaloayanino mo ter Itinreacert amonim mane (in eoniwnstlntt \^ puritj of the product mo refilled V titration mth dfete si&febt using BM98-D (lot 55 MPPO ac pfathalonitrlle) o a standard* fhi* represent* tit# highest yield obtained to date* An optima H%d usage mam to to indicated, tnaaauch oo a dbseouant series mind still, jtraaier aments of *^******* *M*<i>a maned a. do* creasing yield (antinocy aotol usage, hooow, mo also increased la thisserles.) fte indications ar# that excessive aao of both antiaony m*al and snaonlum chloride Is deleterious to yield* %' asiteoaotina sod eubeeauent kruoehlorlts traatmnnt the mom metest obtainsd in &L*$j> yield mo ejmmdiniely' easel In strength* ^yy> md mwm c<phase WH m pfcthalooitrlle (lot 55)* SolvenfcHUling followed bgr hgrpmhlxirlte treatoent yielded a protest m strong* s. tell and rad versus /S phase WPC m Ltrdla* The potent mo res weak* * doll and from mt ex phase ifffO* io-aille4 naterial (hypochlorite-treated) mo eypmlnstsly oqpal in i, dull and rod mrsus ^ phase BPKU ininophthallMdine mo papered ter standard preeeao ( 855 yield) and subsequently- eaployed for metal-free PO synthesis to deterninethe necessity for prefondug this intermediate prior to the Introduction of eatiamgr and nmonlm chloride to tho synthesis mas* If tha Sb pins HHl CX .in ths prsosms of nrm or its decoapoaition products psrfom a ohmioal reduction service, ths loir yislds my possibly' be attributed to orer^rodusttico (persistant mter-eolufcle red an! yoiloir colored iapurltie* la tho product) or to lmuffloieat reduction (consuaptloa of mi mar prevent ths action of the * *-- aMoyM* as a proton donor)* Hetal-fVeo {tthalsmaniai ms synthesised in 4*1# of theoretical yield starting with fhthalegea Brilliant Bins 130 (dilsdnoiaoliiiolinsp 75$ purity') in a nsoam analoffous to that mad for tha jtespasmisii of nataiWrea 1C fron phthalo- oitrils cyolxtenQianins as roteoing agent* ' 1425 1454, 1465. vs^, ;. ^ ligagiaa^^ tiff faiiDiiif ingredients are ^ayry** to. a 0*Titiatr gimo reactor fitted ^|lr' ;a*4ff^Wflfjfil l4*4 O* tMlwliii *<ttw*M<l 1*0 gr* pm**< Molybdate pO0 al* trichlorobetuwns xao charge is first seated to anont *55fe* over a period-, of mom z noure and q u a between 155*0* ***< ido*o* far **** hour* 51 >5 gre* of pmterid f*yfc*Mfy *p^ 47*7 1* j)f oiyetalline inwi)i| aiyiwym* aro -thon iftepe* follomd by hwstlng to t1**** vtm s*faw ia cooled* filtered and washed Mien nMnW****' *ami tw mth acetone* m*. miltinc filtnraakt is sddsd to 4 liters of mtar ***> DUP050069811 fai^iriini TOO M| of wHi twdxftrido a*>A thi reelduel MdarMla am Mmwimt w stem d*4"|i!,^MyT sMialafrse ^Maymii^r Iff dooantffl fron the *>^t.,f<v>ry ponder, filtered, ad malted elkeli-free* Hie prodoati* eeparated frc* antlaony edlte bar htfltit in 500 ail* of eoaeentmted HCl for 1/2 hem fnllrnwl hr *--pi**** %dtb concentrated HCl end finally idth ester. After drying* 96,2 grs. of, natal* flee ffethaaoigmlo* of 9& parity (eerie solfat tltxsfcton) ie obtained, this jjriL.'BaWpwMrmvwtwji two^f A^FtaatVFar* M^eaf w.a>a>r^ r OFaaiawwMa wiiafgcpiwmfimi rgyimSplad^'0* fee predaei ie aoid-peeted tgr dleeolriag 25 re* of ponder in 250 gnu of 1000 wtifmm aoid at G**5-c7 After stirring for 2 hours# the coM eolation ie added dropsies into 2500 nl of boiling mter, The hot elerty ie filtered and ww frea of aaim> She prodnot oan be farther purified bar hypochlorite treating as follows! Raelarry aim a&d*pasted flltereske in a ne liter of mter 2$ al. sodim hypochlorite eolutlon (5-25%) and l*5|r* eodim carbonate. Agitata at roan teapersture for 3 hoars adding aodim hjToohlorlte solution and sodim carbonate at required to Maintain an aaeseea at all tiaaa# Hltar and meh ehlorlde free* DUP050069812 S' I. dtt PQST da mom & CQKPA8X ZB<XRPQBA1D ngPABWBaar (cedt tram eopiee d ft 9) oc$ J. I* fully - Hawark A# Siagal - " S' f Bfcriob- * file 7.3 MWlHillJTFb * UuflBlVVtiMkiaiM'IUIMSt 'Vt^l February 18, 1954 mu & h . c o o h s s ms mar i * mmotmm-jm.mxm free Tabulated bales laa rough ooat oottparlaao of ttandard type ohlortnoslth * aortal*free PS. The MMPC ooat eetiaate la baaod upon a laboratory (HB-1425*80BPB) and the following aanuaptioca (aa aupplled lor Dr. ihrioh)* 1 AaaotM plant uae of 12il aaldtCPO for aold panting. 2 - Aaasna 5*yield looa due to aald pasting. ' f $ <* Aaasna Ifljf plaid loaa due to hypochlorite treatnant. 4 * Aaaoaa no significant ohangee in bsfcob *i*e or operating cycles. .5 * Aaaotie tnof i 1Q SOI extraction. The laboratory product la app*riLately 35S strong versus ST~297-D Ingredients Operating A Dietrlb. Total BmM * &U?/o*t. J73/afta *l89.o/cmt. WL $10O.5/cst. These data Indicate the isotalmfrae product Seoul ooat raugfti*gdl.3Q/lb. taoro to orodose than solvent veil'd BG. This ooat umlty la laraalarmM to loo lie yield (50#)* plaid loaa doe to aald paating ( , 5%) and hypochlorite ' Lon < , 10S) and mate disposal' So attempt sea aide to estimate the additional investment repaired la alas of the Ixlg^bi manufacturing ooat# EPKdried DUP050069813 s i. dm po r t d mmm * oomm IBCQBPOBATEB PIOMSITS WiWIlBMr vp!vi# DE. j* H. COOPER KffMftftr - (Ontt frca copies 0 6 9) oot d* V Fully m Htvark A. Siegel * * F. F. Shriek* " Film 7.3 Hevport, Delaware Rorch 1, 1954 As MpMUd. * rough cost satiate has boom undo for mamfooturo of actal-free jfctlatf^cyimine from phthalonitrlle by en Orohm prooess (see attached). Tabulated below is s coaparleon of the HF-PC oost dots with Sewport eolrent Killed DO. In asking this estimate ths following assumptions were aadet 1 dsns batch else* s ohlorlne~free orudo. 2 75-7650 yield (Orohea data). 3 - FOB loss equal to kerosene loss. 4 - Satisfactory quality by sold posting. 5 * 12il acid} -ifC for sold posting} *5% yield loss. 6 * Phthalonitrlle available at #0.75 #1*25* and 12.00 per lb. (see below). Um Ingredients Operating A Blstrlbrntiree Total Mfg. Oost 63rM.Bg.. # 61.7/ewt. 127.3 0109.0/owt. JggES 0162,0/owt. jjj.ia... |2?0.6/ewt.# is the oost using phthalonitrlle at 00*75Ab. The total swmfaoturlag east be #345*0 and 1445.0/evb. using phthalonitrlle at #1.25 lal #2.00Ab. re* speotdvely. The higher most of RF-PQ t w o s BO is largely due to lower yield (+753*) and high ingredient ooet due to phthalonitrlle pastier EFKJrtad Attach. B* F. B-psnt, s l CHBHICAL BXVISIOH DUP050069814 (JIR^59-1-B# So* 151 HB-4448-187 & HB-4554-140) i FbthRloiiltrll* 1 rat Trlchlor* Boasono 3 " Hoat to 200-210*0 and bold at teaporature 12 boom (still kottlo, opoa to atnoaphoro) Flltar warn Wash vttb aolvont Dry- Hold * 7W7.5* of thooxy DUP050069815 <*4 .h J' ! *r i *t ' . 's. ft***' \ * " '*f 1* . 4, ** % 'K-x s t TfT;--.. a w **? DUP050069816