Document 99L8vqaBN6QyZBxGgJGw9ymrL

P)E Be ANOTRRRTEARR an EP1757581A1 12) EUROPEAN PATENT APPLICATION (43) 2D8a.t0e2o.f20pu0b7licaBtiuonl: t 200709 (51)SIontrClt. aomtarmnen core somone 1) Aopteston umber os2s4362.2 22) Oat of ing: 18.08.2008 84) ADeTsGigEnaBtGedCCHonCYracGiZnDgESaDtKe EE ES FIFRGB GR| 72)+Smyewnetto,rsRobert George SHKU IE IS IT LILT LU LV MC NL PL PT RO SE SI + AClalmepnitoonw,n,BPetAh1A8m10n3-5451 (US) ADeLsGigAnaNtRedKYU Extension States: 90) priory: 24082005 Us 211388 (71) lAgepnitcoawsn:,iPAPr1o9d1u9c5t-1s5a0n1d(CUSh)emica, inc. + ACWloolroenpneetrros,wvnGl,lreeP,gAoPr1Ay811A09a45n8(5US()US) (74) FBReaepncrweksoeGonrdteaotHniovauer:seMuir, Benjamin M. J. 2LonFduotnowwooodrlaacne G8) (54) Preparation of high purity fluorinated peroxides. (in67a)siHmigphpuprrotcyefssuarnwathedepceraorxbiodens farueorprdepar1e9d arocdeuwciwnhiachy'psoelsisoenrttiatolproarof roaegaaccsteeoeduspreaactcion unreacid cuvony uid ana by producersro mpohvaesdefcornmdtthoen;gaasnedoiunsenrtehacetfiuonorpnraotdaucdpuenrdoexrdcgioass ected n gas pase < 52 ~5Hg a w EP 1757581 A1 Description BACKGROUND OF THE INVENTION [0001] Fluorinated peroxides are powerful oxidizing agents and have value as free radical generators and etchanis. In the manufacture of electronic components. Pefluorodimethy! peroxide or sometimes called bisrisoromeptehry. oxide is [0002] an example One ofthe mofaanycoremqmuoinrelmuenrtospeirmopxoisdeedebmyptlhoeyeeldecitnrtohneicseinadpupsltircaytiisontsh.at of high purty. The resting product 10 mrustebeasaunbcdsbtyatpnrtoiadaulcftnrsefeotrofmeusdnirneahcetesdynctohnetsaims,intahnertesa.rBeemcaanuysesaoffettyhesuhiegshalynrdeeecxiriveemeacndarheaszarredquoiursedniantsuyrnethoefstihse: and recovery of igh purty product t[h0e00p3r]oducTthieonfoolflpoewirnfgluaotroldeimsetahnydl ppaetreonxtisdearaendretphreeesernetcaotvievrey.of the art wit restopfleuorcinatted peroxides including 15 [re0a0c0t4i]on oUfSePqua3l,1m0o0l,a8r03amaonudntUsSoPf3c,a2r3bo0r,y2!64fl(uGoIriPdeofw2i6t4u)odrioscmleostehtyhle shyynptohleusoirstoefipnetrhleuoprroedsiemnectehyoif paemreotxaildeflbuyoritdhee: tcartaaplsyscto.olReeadcbtyiolniqtuiedmpoexryagetnu.reTshgeencoenrdaelnsaareteintehxenceisssoefp2a0r0ateCd.bySadimstpillaetoosfn.prInoodtuhcetrsparroecceodlulreecste,dcbayrbcoonndmeonnsoixnigdei.n Is reacted with fluorine in various ras, thus generating carbon fluoride and tfuoromethyi hypofuorte in si. 20 [ca0r0b0o5n]yl UflSuoPri3de,2(0G2O,F7;1)8 wdiitshclcohsleosrianemteltuhoordidfeor(tGhIeFp)reaptatreamtpieornaotfurbeiss (rafnlguionrgofmreotmhy0)fpoe3r0o0xidCe,(pBreTfMePr)ablbyybreetacwteienng p1r0o0duacntdth2r5o0ugCh,aItnutbheeofprgersaennulcaetoefdfclaulocriiudmecshalsor.idIes,olsactriuonbbainndgpwuirhfiwcaatteironanofdBTuMtPecias.uesftfieccoterdebmyovpaesrseisnigduhalecrheloarcitnieo,n hydrogen fluoride, and carbonyl fluoride, passing the scrubbed stream through a -80 C rap to freeze out water and 25 lcoosnsodefnbsies(trheflbuiorrofmueotrhoym)eptehryoxlipdeer.oWxihdeen,tatnrdaftlieorpoamsestihnagnethies plriqeusiednsttarseambtyphrrodouucgta,h udreimtoovgeednasta lrtaostpsarteevppebnyt d10i0t06i]oRnoberts, HL. PrepoafBris(airtfuoiromoetrny) PeraondixtsRiedudctieon with HexafluoropropeneJ,. Chen aSotci.oo(1f19.6474:)1)45a3t8hdiiscgloshes -a ptroaceensdsmhfiopgrhtpehreerpsrseuapraer(ta2t7iuo5n"roCfaeBndT7M8P0tphsrioguig3h7.t3hKePar)eancatrioinckoeflCaOuFto,ciwaivteh. CTFh;eaOuFto(cmloalvaer. 2 isconled1o room temperature and the products remaining nthe autoclave are removedand the gases passed trough qheuxiadfuicrrtorparpso.peTnheenantdheapcroondduecntsactoensiIsstdiinsgtilolfedwlinomaeProsdCbFi,aOl[iaCkaFcoluOmnC.FT,hwehererceovne2r2ediprfoordmuecdt.then is reacted wih [0007] Gard, G. L., eta, ReaocfXetnoniwiothCenrtasin Strong Oxidzing Agents, The UnivoefCrhiscagio Press, 35 re(Cahcitceagdow,it1h96r3lu(o5r1o0m9e-t1h1y1 dyipsocfliousoeivtaertioopusrordeaucctioxnesnoofndxfeinvoonriwdiethanvadrBioTuMsPo.xiIdnitzhiengreacgoevnetr.y sItnoop,neheexreaamcptlieonxpernoodnucst 1225Ciscooled in water bath, then coolet 0-78C and th volatie product pumped away and trough a uid niinttrhoegetnubreapis.Txheenvoonladitfileuomriadtee.rialsothrthan xenon areshtoobewGF;nOF, and OFs00CF andthematerialremaining "0 [c0a0r0b8o]n diUoxSid4ea,4n9d9,f0lu2o4rdiinsecilnotshees paprresoecnecsesoffoarctehseipurmodfulctoiroindocfatbailyssltu,oTrhoexypfruinccriopamlemtphuarniei(eBsDaMr)ebCyFOthFe,reCaOct,ioannodf (CF, although race by liquefaction and amounts of venting the gCaFs,e0o0usCFm:pucratinebs.e present. Separation 0 produce high purty product s accomplished [ha0l0i0d8e], U3.Sa4,,a6-5d4l,4u4o4rod-i-sbciuotsoersyaprporpolcoensysflorcphlroordiudeciwnitghlsoordiiuemcpoenrtoaixniidnegidniwaactyleprearnoxdideexstrbaycttihneg rtheeacptrioonduocftawniatchyal "5 sulable solvent BRIEF SUMMARY OF THE INVENTION 20. f[0o0r1m0e]dbTyhtihseirnevaecnttiioonnosfdarceacrtbeodntyolafnliumorpirdoewveimtehnatihnyapporfouocretses.foTrhperoidumcpirnogvehmieghntpurretsyidleusoiinnasatmepdpiefroexdidpersotcyepsicsfalolry the synthesis and gas phase recovery of high purl fluorinated peroxide product and comprises the steps: (par)isreedaocftitnhgetfhleuocrairnbaotneydlpefrluooxriiddeeawnitdh utnhreehaycptoefdlcuaorrtbeonuynldfelrucoorinddeitwihoincshishestsheanatGiaraseeleouofsurneraectaicotnedprhoydpucituocrotm-e 5 stomed: 5co)ndrietmioovnsintgheurnerbeyacgteenedrcatairnbgoangfalsueoroiudse apnrodduacntysbtyrperaomduccotnstafirnoimngthtehegaflsueooruinsatreedacpteiroonxipdreo;duacntdutnhdeen,r gas phase 2 EP 1757581 AT ) collecting ihe fluorinated peroxide from ste (5 in as phase. 1in0c0i1u1d]e: Significant advantages can be achieved sing th simpiied gas phase recovery process and soofmhease an aity to produce fluorinated peroxide of sufficient high purty to be used diecty for electronics appications: parnoacebsisettsyo; siminahtelowtemperature condensation stepsand stationtaps associatwietdhpropurficaton an ably0 produce such high purty fluorinated peroxide without he needfor a distlation ste: and, an abity toreduce he hazards associated wh ow temperature recovery processes employing condensation in producing highpurty fluorinated peroxides: DETAILED DESCRIPTION OFTHE INVENTION 1f0o0r1m2e]d Tirseianctvienngiaocnairsbodnirefctuerdidoeanwiitmhparohvypeomfeunotrtien. pTrhoecpersoscfeosrsthspgrenoedruacltliyocnoomfphriigshepduroftywofisotrenaptsedhefpesrtoxisdteesp 20 iphnavsoeinrgechoeversyynonfetshiesfloufohrienatfelduopreirnoaxteiddepefrrooxmitdheecorneatcatiinoinngprroedaucctti.on product and tha second step Invahing he Gas 1y0p0a13f)ioTrhkteefoifsotsrttehpinltahoerpnreotceedsspiersoxciodmep.riTsehtohyepaocftunograecmaarybboenypfluroridee pwripihoratahoycporonftuaeocrttweditshutchheacsarrbloonryolmleutcnriyde 2 oflrofroimdasda,lti.nLsiitk,eawifhsoreecxaarmbpolneyblyfluiohreiderceanabcotffociramroebdonnpmotr0nreaecotiwoinhwfihluthoerhiniytpnoefuporrtesoennocfieatacslfaoyrse,xaom.p6l.ea obyrrfeaocmteidngncairtbon moonneoxdiedseirweisth fluorine. Depering upon the reaction scheme selected reactantsmay be preformed s10u0c1h4at]ifuExoarmopmleetshoyflhyhpyopfoufourottees,schiourfoodrfreieuaocrtdoimoenthiyn|clhuydepohfeuoGyr., eanktyahfyupoorfoueotrhtylasPaynpodfCuo,rt,bihseatlakfyhuyoproofpvroorptya!s rypoandfbis(ufucrooxyrdfuotromeetha,ne. 10018] Prefered routes 0 desied fluorinated peroxides are described by the equations: " A excess COF, + ROF ~2 ROCF; + COF, R= CF (x= 1-8) `8 excess COF; + RY(OF); --a R{OOCF;); + COF, R= CF (x= 1-8) 1in0c0l1u6d]ing thheassimbpeiafnicfaotuonnodtthhaet orneecocvaenryrperdoucceestshebyhaiznaradls caosnstorcoilaitnegdtwhiethretahcetironeccoovnedriytioofnsflsusorsioncaitetdedpewrioxhidtehse 5 oyfntihheeshyip.Aoniiunotratlacbejmepcltoiyveednitnhtehseyrnehacetsioinc.ltRheaectfiuoonricnoanteidlpoenrsoxairdeeicsonotnreoollfeedftcotdnigeetheselquciommplebtasceodnvreearcstiioonn l10escsotmhpalnet0i.o5n%lehayvpionfgueosrsteengteianlernaolheyspsoftuhoarnte0.in1t%hanrdeapcrteifoenrapbrloyduecs.sths apnre0f.e0r5r%ebdytwheitgthth.reaction product have 10017] Ina preferred embodiment bisforomethy) peroxide i produced byaprocess which comprise: 55 c(ao)mrperaictsiendgocfarbbiosr(yv!lfuioorroimdeetrwiyt)hprefruooxridoem,eturnyreahcyipeodfucoarribtoenyulndfleurocroinddeiatniodnbsyspurcohdutchtasatangdasheaovuinsgrefaecstsitohnapnro0d.u5c%t triluoromethy| hypofuorte i formes; a EP 1757581 A1 c0o)ndrietimoonvsintgheurnerbeyagcetneedractairnbgonaylgafslueooruisdepraondducbtysptrroedaumctcsonftaoimnintghesagladsbeiosu(sfrueoarcotimoenthpryo)dupecrtoxuinddee;ragnadsthpehna,se ) collecting the bis(uoromethy) peroxide from step (o) i gas phase. [0018] A key factor leading to a reaction product essential ree of unreacted hypofiuorit fes in the reaction stochboymetrhye.abAosvteoiechiqomuetraitctoecxoicmepsolsetnoifocsna.rbMoonlyalrfrlatuioosrotfioctdaherebohnyyplaffiluuoorritdeeitsoehmypploofyueoditteo darrievegethneerreaalctfironomas1.r1ep0r.e3s1enatnedd 10 prdeofxeirdaeb,lyhyfdrromoge1n.2fl1uo1r.i7:d1e.,Oftluhoerirnbey,parondducatdsvecnotmimoaunsiwyaftoerr.meTdemipetrhaetrueraectsioonf ifnrsommal1l5t0rtaoc3e60amoCunantdinacultudoegecnaerobuosn pmraedses.ures are typical. Reaction conditions vay depending on the hypolluorte used and the fluoinated peroxide beng 10015] 1t has been found tha by conducting the reaction of carbonyl fluoride wth the hypafiuorie under condiions. 15 sreumocvahloftthheat essaunntraelayctneoducnarrebaocntyeldflhuyorpiodfeaunodrbe yrepmarinos,dfournoecmcttahnseriemapclteiomnenptroadugcatsapnhdarseecorveceortvehreyflpuroorcienastsetdpoearcohxieivdee.: without passinghe reaction productthroughlowtemperature condensation taps. By maintaining gasphase condiions. [th0r0o2u0g]h_ouItntrheecobvreoraydeosntesaevnosidesrtehceovhearzyoafrdtshaesfsloucoiraitnaetdedwipterhoxiigdheyfrreoamcttihveegcaosmepoouusnrdesacitnicononpdroednuscetdcfaonrmb.e achieved 20 bayndpanyabysprtohsdeugicatssen.ouAgs lreacktionaprolducet rAxouzgecohlteshsoarandbaennbnheydtgdcraopeuasbsldoedoa3f-rem1meogvri0anngtu5lheecs roenetxaemmioafrnptbhaoelardtsafoilrurboneringydtes, c[0a0p2a1b]le ofInrtehmeopvrienfgersruecdhreccoonvteamriynparnotsc.ess the gaseous reaction products inal scrubbed with an aqueous medium, typical an aqueous akaine medium, in order to hydrolyze unreacted carbonyl fluoride, and neutralize any acid 25 chyodmrpoxoiudned,spoptraessseinutminhytdhreoxgiadse,sctarleacmi.umAhnydarlokxaildieneansdosutoofnorthavsinagpfrerfoemrr5edtosc5r0u%bbibnygwaegiegnhtt. of akal, . Sodium 10022] In the secondpartofthe recovery process, the thus aqueous reated reacion product s passed through one. oanrdmoernetraabisnoerdpHt,i0v,e bReedpsretsoeanstsaitsitvien tahdesoermbaevntaslsoufltuendrefaorctreedmocavribnogncyolnitvaomriindaenatnsdfbryopmrtohfdluucotrcianrabtoendcpxeirdcexsi,de.p.r.oCdOusc.t 2 wiinthcthleufdleuzoeroiinteastesudcpheraosxi3daenpdro4duAct.zeoInlttehseeavnedntsohdaat-ismoem.eScmaarlblonpoorxeidzeesairteemsaisnhoautledrpbeasussaegdestohraosugohathveoiaddsreoarcbteinotn boexdi,detshoerparnoodtuhcetrmbaeyd obfeapdassosrbeedntthrough a reactant such as soda-lime whch i capable of reacting wih the carbon [0023] The folowing examples ae provideod lustrate various embodimeonftths invention and are not intended = to restrict the scope thereof. Example 1 Preparation of Bis(ruoromethypercxide Mole Ratio 1.52:1 " [0024] Reactants carbony florid, COF, and luoroxytrfuoromethane, GF OF, were prepared in alow system and collected in a clean and dry 600-co Monel pressure reactor. A ota of 500 mmol COF. and 328 mmol GF(OF was. c`oalulteocgteendoursepprreessesnutriengtoa2m74orCorvaetrothoefCcOou;rsGeFo;fO3F. hofou1r.s5a2n:1d. tThheenhmeilxtduarte2o7f4COFf,oraanndaGddFt;iOonFalw2ashohuersa.tAefderuntdheer 4 ispnedciiecataimmietx,teutrhdeeomfixCtuOre,waansdablilosw(eidlo0roComoelthfoypaemrboixeindete(mBpeTrMat)u,reC.FOAnOCIFnfsra,rewdishpencotGrFumOoFf tohbserrevaecdt.or contents f[o0l0l2o5w]ed bThaebygeadseoofuhseactoancttevnatsteodf 4thAemrleaecctlorarwsereevepaasnsdedsutbhsreouqguheantpyucorlflieccatteodn rinaaicnlecoannsaisnidndgyofcaolcleocltuiomnncoyfliHndOe.r at sub-amblent temperature. Infrared analyfsthse product in the collection cylinder indicated high-purty GF(OOCF, (ayBeTofM60%P. )eviwdenicetofahnynCOo,H,0, COF, orFOFpresent. TheBTMPproductweighed33 3gwhich represents. (10C0F2;6O]F ntUshiengretaictsiorneapcrtoidouncatnadnretchoevesreypaprraottioocnolhaoznaerdiss aabslseocfioataevdoihdertehewihha,zards associated wit the presence of Example 2 Preparatioofn Bis(rfuoromethyperoxide Mole Ratio of 1.25:1 [0027] nanexpesimriaritomhatedesncritbed n Example 1,443 mmol of COandF354 mmol GF OFwascalected 4 p 1757581 A1 `perperesseauntrieng a27mo0laCraantdotohfeChOeFs4beOtFwOeFenof271.025C1.anTdh2e8m0uCtefoofrC3.5OhFo,rsa.ndAfOeFr(hOeF swpaescifhieeadteidmeu,ndheeramuitxotugreenwoeuss i`lsofwueodrtoomceotlntyopaemrboiesndtete(mSpTerPa)t,urGe.F,A0n0CnF,a,rwhspneoctGuFm,OofFhaebsreeravcetdor contents ndated & mixture of COF and 5 a[n0a0l2y8s]isTofhtehprpordoudcutcotfntihnereecsocllleocntiwoansypiunrdeedrainnddciocaltleedcitgehdapcucrotrydiCnFg{o0t0hGeFm.et(hBoTdHPd)eswcirhibneodienvEixdaemncpeleo1f.anfyaCr0e3d. 1,0. COF,,or GF(OF. The BTMP product weighed 36.9 g which represents a yield of 61%. Examples Preparationfis(riuorometnyperoxde Molo Rao 1.99: 6100002-5c)c MoRneealctpraenstsucraeorneaycltorr,iAtdet,lGoOfFS,5,0amnmdoflloCrOoFyytfaundor2o8m1emhmaonel,GCFFFF,wawsrseeddisrteliperdesnaoni8ngceaamnolaanrdadtroy 15 coCuOrRs,ofG5F.,0hFouorfs a1n.0d01,thTehnehemlidstiureo2f6C9OFC,faonadnCaFd{dOtiFonwaalshhoure. dAfeurntdehreasupetcoigfeineodumsep,retshseurme 10.i27w5aCsraolvloeewhered 1(0i.ocorooltmoeatmnbyipenetrtoeimdpeera(tBuTreW.P)A,nGnF,a0r0CsFpweichtnoofGtFh,OrFesatbsoecrovnetdents ndcated a mire of CO, COF, and bs 2 a00b3e0d]othTehaotacconttievnatt4eofdhtmeolreaccutoswieerveespanadtsh treosutgehdacopnutrefntcsastuobnsaeqiunenctolnsyicstoilnegtoefdancoalcuemannoafnHa,c0rfyoclollolwectibony CpFi,n00eGaF,u(bB-TaWmbPl)eanntdteCmOp.eraAtpupraer.enItnlfyrartehde amnoalleycsuilsaorfshieevepsrowdaurcet ninattchocmolpeectlonfcfyalcitnvdeeraitndriecmaotvedinagmCOiy.reThoef c`AnaolysnisootffhteheeccnyollietndcetsroncoyntienntdsecrawteeredsnigpahspsedurGorFu;g0ht0aCycFo(uBTmoMf)swioh ndoaeniaddecno-clsecomifedany Ca03e,anHOd,ycCyiFndero.r = G10F03F1.] Tis example shows tha increasing the malar rato of carbo furide to tforametny hypafiorte above ca1.r7b,ohnoouxigdhecoenfteecnttv,efao wmeilnicmirzeinagstihnegvetlheofefvelloof urnreeatctehdypcoafrlouoorrtyeonrche,reaacntdiohnaptrocdruecatsredeolndInmcaryeaplsaecde nnacassary burdens on the scrubbing nd adsorbent systems in addtoo tnhe fos ofreactant arbor uorid. Examples Purfcaton of Crude Bisrfuorometnyperoxide Wih Soda-Lime 35 c[o0l0ec3t2e]dinaAcnculdeeansaanmpdldeycocntoailniengccatimiinxoteunr.eAof BnTWPaofatnhldecCyOylFi,ndsweracsoinptaessnstsedntciocuagtehdcoghlupmunrkoyfCsFo0da0diCmeFa(ndBtThMe)n with no evidence of any CO. 0, GOF, o FOF. [c0o0n3t3a]minaTtheiss fexoammpaleeadcemtonnsptrroadtuecsttchoanttaiinisinpgoshseiblfeuotroneamtpeldopyeraoxsiidneg,le adsorbent to remove substantially all of the amps Puricaton of rude Bs{rfuoromethyperoide With Water and Soda-Lime 45 [0o0u3g]h Acoclurmnuofdodea-sdmaenanpdtiheen ccoloeconftTdtMinaaPcialennadniCaOnnFdgwryaascopmlaesicsteisodnturcyorlunegehr.acAonlaulmysniosffH,i0eaynidnsduabrsceoqntueenntst inciceted igh purtyGF00GF: (TMP) wih no evidenocfan Gg, HO, GOFy.orGF5OF. Comparative Examples Puricaton of rude Bsrfvoremethyperoide Wih Soda Lime 0`c0o3l5u]mnAofnsaottdemapdt itwomapesnuotrscturcucydeessslalmpalsehceonptraoicneisnsg ageinsertautredoofxByTgMenPaasnweClFasOFarbeympeanssdionugstahmeomuinxttoufreotcraoiuzgehd 55 heat. That heat caused he subsequent decomposion of tha remaining ETP. t[0e0a3c6t]on~Tphriodsuecxtacmopnlteaisnhinogwsuethaecuinesuditpaboillitlyoufttheeg8asstph hasecarseecowvhearnyofCfOlFuo,riannadteGd pFerFoxiadreeprreoadcutcetdfirnomeqauaglasmeooaurs `amount The scrubbing of th reaction produc by contac with column of water nd removal of carbon xis s EP 1757581 AT Claims 1. Acopmrporciessessftorhpe srtopos:duahcgihpnurgty fluorinated peroxideby racing carbon furde witha hypafiuorte which c(oemrprieseadsocafistadicdiarfnbuoongnyatfeudoprriovwiidhessainddyupnorfeaucotretdecaurnbdoenryclofnliuoorindse wshucihctshatesasegnatsiaeloluysfreeeacotfiounnrperaocdtuecdt y(5p)roefmuorvitneguisnrfoeramcetde;dcarbon lurid fomihe gasereoacutison proundderguascphatsecondos hereby 0 generating a gaseous product stream containing sald fluorinated paroxide and then, () collecting the fluorinatedperoxidefromstep (b) in gas phase. 2. ApraocfeClsims1 wherein th reacon synnesi describe i tap (8) represented by the formuAlaansd " a excess COF, + ROF --2 ROOCF; + COF, 8 R= CyFp (x= 1-8) excess COF; + R{OF); -- R{OOCE;), + COF, Rip=CyFy (x=1-8) 3. AprocofeClsaism 1 or 2 wherein the mole ratoofcarbonyl fluoride to ypofucfrtom 1.1131 4. AprofCoecm weherseinssaid molerato rom 1210 1.71 5. A`apureoocuesssmeofdiaunmy aunndeeorfctohnedpitrieocnedoirnghcyloarmosyzwnhgerUerienatchteedGacsaerobuonsyrlefalcutoiroindeproducts nil contactedwith an 6. AprocessofClam 5 whereinthegaseous reaction produciscontacwithehdeaqueous medium underconditions for hycraing carbonyl fluoride an forming an acide compound. "0 7. aAqupreoocuesssreoafmaennyt,onie poafstsheedptrrecoeudgihnganclaabismosrwbhaenrte1inrtehmeogvaesaenoyusunrreeaacctitoendpcraordbuoctnystleoarmd,s,afbeyrprthoducopttsioannadl 8. AprocofeCslism 7wherein the adsorbeznetase lecularsieve. 455. AprocofeClsaism wherein the molecularsieveis 3Aor 4Amolecular ive 10. AprocofeCslism 7wherein the adsoirs abmoelecnultar iovor soda me. 11. ACypgbriosscoyefhysapnsoytaonerotfesthe preceding ims wharei the hypouorte i sleced rom Cy. alkyhypofuoies and 12. Apolprlouctees,seonftGalllaimor1o1etwhheyrhsyipnoftuhoethey,pohfeiputoarftueorisopsreolpeycitepdltorermee,layn!d bhiyspo(fluoorrotes,ydculoorroomdeftuaonreo.methy hy5513. Aprocofeisasm 12wherein the hypoforte fs furomethy hypotuorte 16.isApprersoenctoenfaasnnsyaomneoofuotfhneepstrechedainng0.c6a% mbsywwehigehrts.i unreacted tfloramethy hypofcrte nthe reaction product 6 EP 1757581 A1 15. AprocofeClsaism 14 wherein unreacted rfuoromethyl hypofuotte nth reactionproducts present in anamount ofess than 0.1%byweight. s 16. oAf pesrs o0.co0f5eC%lsbayismwe1i6ghwtherein unreacted rfuoromethyl hypofuotte nth reactionproducts presenti anamount 17. A process preformed of any prior to orneaecotfionthe preceding claims wherein the carbon fluoride and tiuoromathyl hypofiort are 1018. A process of one of las 1 to 16 whereln the carbonyl fluorideandorthe trifluoromethyl hypofivorte are formed insu. = 7 Ep 1757 581 A1 [-- 9 ota EUROPEAN SEARCH REPORT cJ o-- m DOCUMENTS CONSIDERED TO BE RELEVANT [oseS ] temn re d |be|e temr as| ho [1u6shA3eu20guush2to60le1A9d66o(cPuO(mR1eT5En6Rt6,-0+6R-O1G6E)R S T AD [1-18 | IcCowor.rctioaro/n1o/so x eS+qauSmaatbpirloenes1ss21a5n3d 3 14 vo ++ CGoalmutme4s,1i3nes 1:5 + 5-10 A 4[1v025)0382620h2Aautg7eu16stdAoc15u(6mE5e.LnLtI(N1+G9B6O5E-08E-L2L0S)VORTH K ET [1-18 vo |* example 11 5-10 v 2fS2uusmsfaor6ry2i2ofe19s6t7hea(1i(3rn9ovn7e-nG0t4ii-o2nn2)w 1s) s-10 olim's, Tine 52 - Tine 55 * | UoanmiaveenrsseityroefeMirnnesota: 10 0YS0ThE0oV3vE4eN0n6bC0el7ra7s2:064"So(d2a0c0L4i-n1e1-0V1a)p,or Trap Ta i e SaHFeactbhhs.:tLirmaec-thsi+omfl 15.um.edu/research_old/hal/ em] S|wan| vowmer 2006 | ronda, marenara | EEE. if EER i yom f= + iopon rns s BE ---- EETT tee [ams [em[m[um e US 5622682 A 22-04-1997 NONE 8 Formoredota about 1s amex: seeOficial Jowral of th EvoPapteaOfac,nNo. 12682 . EP 1757581 A1 "REFERENCES CITED IN THE DESCRIPTION Tphaitsenltisdtoocruemfeenrte.ncEavsecnittehdobuyghgheraepaptlciacraenhtassfboeehnerteaakdeenri'nsccoonmvpeinniegntcheeonrleye.rIentcdeose,snerortorfsoorrmopmairstosfitohnesEcuarnnooptebaon `excluded and the EPOdisclaimsall billy in this regard. Patent documents cited in the description ++ UUSs33213000AA28[[006000004344]] + US 320271A8 [0008] ++ UUSSB44a99dAA0[[00200a00498]] Non-patentteature cited in the description + RPeOrBoErRdTeSa,ndH.iLs.RePrdeupcatriaotniownihofHBeixsa(fliofruooprroompeetnney.) J. Chem. Soc, 1964, 4538 [0006] = SGtArRoDng,OGx.idLz.ientgalA.geRretasc.tiTohnes UofnXiveenrosniwoiftCCheirctaagion Press, 1963, 109-111 (0007) 0