Document MJ82GYjYp7Dm5X0nv9XVYpO4j

I *) l June 13, 1961 j qA27i CAPACITOR CONTAINING AN ALKQXYALKYL ETHER AS A DIELECTRIC Fiid Bay 21. 1959 2 MS (57Q CHLOROPHENYL " ' 10 )/l A FIG. I dielectric metal -CONTAINING ELECTRODES AN ALKOXYALKYL CHLOROPHENYL ETHER FIG.-4 FIG.-3 PAPER IMPREGNATED WITH 2-BUTOXYETHYL 2-CHLOROPHENYL ETHER INVESTOR. JOACHIM DAIIl AGENT | ' HONS 201745 <r* i c United States Patent Office 2.988,879 Ptttnltd Jun* 13. 1961 l is to provide electric*! apparatus having tong, useful 2 9M 879 life and good dielectric stability CAPACITOR COXIAIMNC AN AI KOWAI.KVL According to the invention, Hick and other obicrts CHLOROPHENYL mint AS A DIELECTRIC which will be hereinafter disclosed are provided bv Ihe Jofifhiin Darri, Basel, Sw Urcrfnrtd, assignor (o Monjnxto Chemical Caiupaii), St, Louis, Mo, a corponlioa ef Delaware Filed Mar 21. 19 Ser No t|4,gt} t following invention whcicin there is provided electrical apparatus comprising, in combination, conducting etcmenu disposed in sp.iecd relationship lo each other md J Claim*, (Cl, 317--15`i adapted during operation of the apparatus, io have a different! la electrical poieoiial thcr-bciwcen and, inter The prowm invention relate* lo clecincal device* and Id posed between mid tbMMi for insulating one from the more p imcul.irly deal* wtiit apparatus comprising a com* other, a liquid dkWesrir medium oomprumg nlkozy- bi nation of electricity conducting element* and dielectric aUtyl chloroaryl elbora qf the formula uuulnting media The ute o( a dtelcctne n required in certain electrical R. equipment lor the purpose of removing beat and of al ** -|-fO(Cll.).0*,|. lowing the making of tleclrtcal contact in the abacnet of mr or of explosive mixtures The requirements for such dielectric* are, among other thinp, very high re Ht. sistance of the now of electric current*, high stability lo in which R is an alkyl radical of front 1 to 5 carbon .lintorphcric condiiion* at ordinary and at tomewhat ele- 10 atoms, z is aa integer of from 0 to 4. m is an integer v-ited temperatures, high minancc to thermal decom of from 1 lo 2, R' is an alkyl radical of from 1 to t position, low vapor pressure, low confta!ia| tempera carbon atoms, sum integer of (rum 2 to 4, and i* ture. low inflammabilny and high Hath point Prefer an Integer of from l lo 4, ably the dielectric ihould be a mobile liquid even at Aa described io my copending application, Serial No. relatively low temperature* and ihould ba a |ood heat a* 5JO,239, bled November 30. 1955, now US. F-itent No transfer agent 2.4U.4W, alkoxyalkyl chlorosryl ethers of the above In commercial practice, high boding fractions of petro leum distillates have been largely tiled for (hn purpose formula art readily prepared by heating a chlorinated aromatic hydrocarbon of ths formula There liquids do not satisfy ail of the above-stated re quirements They are relatively, poor heal transfer ,, agem* and under the condition* of their u*e they gradu- jlty decanipore with the formation of nodealrable prod- tin* which adversely influence the electrical propeme*. O"- - Some of ihc*e product* are tarry, and others are ap u with one or two moles of in ilkoxyaUmot of the for preciably volatile and may present Are and eaploaion mula R'OfCHjl.OH, where y, i. R. R' and i are aa hazard*. defined above, Chlortne-substuuted aromatic hydioesr- Another disadvantage of the mineral oil* i* that they bong having Ihe above formula are, for example, on ho-, lend to form deposit* generally known a* "*iiid*e" dur mesa- or para-dichlorobenxcne, 2.3-, 3,4-, 2.4- 2.4-. 2.5- ing the pcuod of tbcir u*e. This i* due lo oxidation and or 3,5-dtcblorotolueile, 2J-dichloro-p-xykne, 4,5-dichto- deeompotiiien and alio result* to aome extent in the ro-m xylene, 2,3,4-tncMoro-n-btiiylbcazcnc, ar-trtrachio- formation of acid* which is equally undesirable The (OAeri-amylbcnzene, pentachlorobenzene 1.3 5 , ,2.J- sludging of dielectrics during use is a serious disadvan or t,t,4-trKhlorabenzcne. 1,2,4.5- or t.2.3.5-tetrachJoro- tage .inti requires either replacement of (he oil or treat bcezene. J,6-4ieblMo-l,2,,Jletra<lhylbertfne. ar-di- ment lo remove the sludge and revivify the dielectric A *g chloro-p-eymcnc. at-diehloro-ar-tert-binyl-m-xylene. ar- Miivfactory dielectric liquid should not sludge or undergo dtchloro-ar- tsobutylmeitlyiene. ar-inehloro-1 4-jdvdyl- siibvt.intinl deleterious change during uac usd it a one benzene, etc. Alkonyaiktinoti which are reacted with the of the ohyccts of this invention to provide a liquid which docs not posset* (ha imdeuribie disadvantage charlC) chlonnalcd benzenes or the chlorinated .itkylhen/ciks mcording lo Ihe invention are those having from I lo * u.ir icmticot the mineral ode go bon ittome In the atkosy rnsbcivl and from 2 m J sxrhun The undesirable effect of decomposition n further toms in the alkanoi portion of the molecule, r g 2-iru.th- manifested when the mineral oils are used n capacitor oxyethanoi. 2-buioxyrihamil, J-ethaiyprop mot ; rthiur imprCftAantt- Thus, msder high operating icrnpcrviurcs ethanol. 2-atnyloxyeihanoJ. e-eihonybuiano!. j-mrihoxy- and direct current voltages, eapaciiors impregnated there propanol, 3-amyloxypropaiwl, 2-octyloxyeihunc.l 2->*o- with undergo a characteristic type of deterioration which H propoxyrthanol, 5-bexyltuypropannJ result! in an ever increasing leakage current, a short Reaction of the chlorinc-siibsiiiuled benicnoui tom- capacitor life, visible localized decomposition of the di pound* with the alkoxyalkanoli lo give the ptcs-mlv electric end common of the electrode* Moreover, in useful atkoxyalkyt chioronryl ethers takes pU,e ti tddy the c.itc of capacitors operating on alternating current, by besting the two reactants in ihe press fk* p( art the decomposition sometimes results ta an excessive in qg alkali metal hydroxide, it, Sodium, potassium or lithium crease in power factor of the dielectric material hydroxide, at a temperature of from. U), 150* C la It is. therefore, an obicct of the present invention to 210* C. at Ordinary atmotphenc or mcrci-ed pressure provide u method for ihe insulanon of element* m elec until formation of the ethers bar take* place Since <fu trical apparatus wherein lb* above obiectenable proper- reaction may result in the replacement of mole than one tics arc either completely eliminated or substantially re 0t Chlortne atom by the alkoxynlkoay radical h,-n .touring duced a preponderance of the substitution of only one chlorine An additional ob;eci is io provide transformers, ca atom by the alkoxyalkoxy group, it is generally iilv >- pacitors, circuit breakers cables, twitches, fuses, reactors, able to imc a large excess of ths chlonnalcd he remold regulators and the like wherein the deleterusvn action compound Oft the other hand, when the mnr product common to the prior arl dielectric materials such a* ihe JO to he obtained i* the dmber, an excess of the tlkoay deterioration of paper insulation and metal parts alktool is advamageodtly used. The quantity of alkali eliminated or materially reduced. Stilt another obrect metal hydroxide employed is il eomewtiat controlling 1 HONS 20X746 S ` 4 in the type of product obtained Hjdrogcn chloride it phenyl ethers are characterized h> pn.piriicy liberated in (lie replacement of the nuclear chlorine by recommend ihcm for use as liquid dielectric* the .ilkoxyatkoxy tnoicty of >be allnxy ill, .no), and m Another presently valuable class of ethers arc tb-'se order lo obtain pood yield* of ruber the mono-ether oc obtained from a tnchlorobcneene and *,iid dxoty 'he di-ciher, llicrc thou Id be prc**.rsi in ihe reaction mix ( alkanols These may be represented by the formula ture cnouplt of die alkali to neutralize the libcrutcd acid Usually from one to two motet of the alkali metal ct IijJ-oxiJc per mole of Ihe jlxoxy ilk .noi ti incd An exccsi of sodium hydroxide it not detrimental to Ihe o-iPii,on retcuon, where** a quantity which u cuOttaniially teat 10 iLeii el),u of the alkoxyalkanol on a motes bun it eon- due,re to lower yield! of ether product The reu, .1011 tune .mj kinperaiure appear! to have little, if any, cfTcct on Ihe nature of hie enter product Al'liouph a primarily formed mono ether will rel w,th another mole of aikoxvalkanol lo yield a dicthcr higher temperatures and/or continued healing (tone do not suffice in effecting stihstanual conversion to Ihe diethcr in which T sciec'cd from the d,,*i con-i-unt. nf ehloftno and Ihe radical Q--(01,1,0(1' viuMn , denotes an integer of frasn 2 10 4 and K1 ,s an x> 1 14 radical of from I to t carbon atoms The mono -met* which are obtained by tsaiatg a large excess of iK in chlorobenzene with lha altwyalkanol, have the formula An eicett of Ihe alkoxyalkanol ore' that required for toreplaecnteni of one chlorine atom ihouid be present in order to obtain any iubttnnti.il fotmalion of the diet her Whether (he rcnctam quantities preienl arc those which favor mono substitution (excess of chlorinated hydro carbon) or whether the proportion,, arc such aa to favor They may be broadly referred to as aikoxyulkyl Jithu, n di-subttituuon (excess of alkoxyalkanol), ether formation * phenyl ethers having from I to 4 curt-on atom* m the occurs after heating at a temperature of from IJO* C alkoxy radical and from 2 lo 4 carbon atoms in the to 210* C and preferably of from 160* C-210* C or alkyl radical Examples of such presently provided 2!0* C for a unit of. say, several houn lo a day The monothcra are 2-butoxycthyl 2iJ-dichk>mphcayf ether projects of the reaction can be penenUy followed by 2.4-dichlorophcnyl 2-metho>yethyl ether 2.6-dnlilnro noting the refractive index of the reaction mixture or by ** phtssyl )-*thoxypropyl ether, !,j-dichloropbenyt a pr noting the quantity of water being formed aa the liber poxybulyl ether, etc Examples of dt ethers provided ated hydrogen rhiondc is neutralized by Ihe wdnim by the present invention from the (nehloroK.-nr.-ne* arc hydroxide Wliilc provision for removal of water during e.g., 2,)-bf2-ethoxyelhoxy>chlorobenn;n< 2 3 hiu; -he reaction is not required, better yields of ether product ernybiyethoxyKhlorobcnr-cnc. !.4-brxf4-methosvhn(oxyu and a ready means of determining reaction rate arc ** chlorobenzene, JJ-btaO-ixopfOpoiypropniylehlorobcn. afforded -by operating in a reaction vessel which t> zene, etc. The mono-ether* and the dt-ethtr* .ire re -diiv equipped with some water-removing facility, eg., a water separable by fractional distillation. but since both po**e*s trap or take-off head dielecinc propertscs, the isolation procedure may be (re Although, as above sl-ttad, ruction of Ihe chlorinated quently omitted wtsan these cornpounds arc to he und bcnzenoid compound and the nlkoxyalWanol can be so ** in this Acid. directed aa to remit in a preponderance of either mono- The telrachloeobeiuenex similarly react with the or dt-cthcr formation, generally the product contains aUtoayalkanola to give presently useful mono-ethers. mixture of the two in varying proportions. One class of presently useful ethers by the present B'O(CBd ,0 ei ' mveniion are the mono-ethers prepared from ortho-, mete- and para-dtehlorohcnicne and an alkotyalkanol of the formula R'OfCHi^OH wherein It' ia an alkyl radical of from I to cariwo atoms anti a is an integer of from 2 to 4 Thus from onho-dtchlorobcnzene and 2-n propoayethanol there is obtained 2-chkuophcnyl M Md pmrntly mIU di-cthcri 2-n-propoiyethyl ether; from para-dtchlorobenzenc and ro(OKi>o ci 4-butoxybutanol there si obtained 4-butoaybuiyI 4-cMoso- phanyl ether; from mcta-diehiorobcnrene and 1-meihoxy- ethanol than it obtained 2-chlorophesyl 2-maiho*yathyl ether, astd from ortho-dichlorobanzcnc and 2-ethoxy albootoi there a obtained 2-chloropbenyl 2-ethoxyethyl K'OfOHJtO ci atbor. Thsoa ana formed according to the reaction From l.2*).4*ittrachlorob;fucne and* e j, ; meiho>> 01 ' otcno.or ethanol (heir it obtained 2-mrtiwtkyeihyl 2 3 J-in.hloro- phenyl ether u ihe meno-elher prcKlu.1 and brsiT H mcthoxycihoxy).3>4wdchlorobcnzene ** (he d. vliter jwoduci Pcnlachlorobcnxent Irkewtw undergoes replutmcni of one or two chlorine itonf hy ilkoxv.ilLo*? m Varying quantiues of by-product chlormc-frec di-etber five yratnily luefut ether* Thus, with 3 nho\vpron*> may also be formed in (ha reaction, depending upon the 4# nol there is obtained 3<ethoypropyi ictracUInrop^wn;! reactant proportions, thus' ether as the moiUKciher product and ar-t*( WiboM G.-. . OtCHxi.OH 0(011.) .OR propoay) inchlorohenccae a* (he di-dhrr product I have also found (hai (he pre^nce or an jigvf s i, attached lo the aromatic nn* of ihe thiorinitu) ft, .s' Yd carbon component neither detract* from im* which replacement of the nuclear chlorine hy ihe alkoxy radical lake* place nor front the di.ii-irK The cblorine-free di-etber is easily separated from the efficiency of the ethen. Tk dichlorobeneene mu n. chlorine-containing mono-ether by fractions) distillation tubtiituted hy from I to 4 aJkyi radicai*. the ir>chio ^ As will be hereinafter shown, the aikoxyalkyt chkuo- TO beotene vttfe 1 to 3 alkvl radicals. etc Thu*. frwn HONS 201747 3.M8.67& 56 r 7 rfirhlorttfihvltonrcne and 2-clhxyihanol ihcre >i * from ccltuto.c, c f , pulps, fibers, icxiilcs or paper, derived oh- ..uni nr.J*o cbJorflcihilphcny] 2*cihoxvcihyt rthrr from wood, colton or linen, which porous product, have : ' t'-O cihovvrihot))cihytKn7cne as by product From bten impropriated with the present .ikoiyalLvl chloroaryl ir t\J >f inchtarobcnttno <ind 4*mclho*ybutanol fhcre ethers A noteworthy feature of the present invention 1 s imtamcii -r mm! ;ir djchiomphcn>| 4 mcllinxybuly? 6 is the provision of a capacitor comprising a pair of elec <"Vr ts ihi- ninnocihcr product and *r amyl-ar Hisf4- trodes and an msulattOE agent associated with each of r,, i cHoj P.rcn/1 nc the d*-CibC] product the electrodes and isolating them from each other, said rri'-- - oproml ir tci'ircMornbenzenc and 2 hutoiy- insulaimc agent comprising a eellulosic material impreg c"!" i"oi ^ ;mi l trt\> oKj (ined ar b>(? bmoxyctbony) nated with the present ethers ir-d . ore r '.rpropN lbcntcnc From the pQtya^ylaifd 10 Examples of electrical apparatus in which the present ar u ;pforo trrmcih>Siemens and 4*cihoxyhrtafio? there ilkoxyalkyl chlorophenyl ethers are valuable components is ohi fined Jhc mono-cihcr product ar cMoro ir lucth}]* are shown tn the nccompanymf drawing phenvj J cPio'yhuiyl eibcf 1 Ki'w fooiut tlifll the above divtV.'sd alkoxyaUyl FIG 1 ta a front cievMton pertly m section of a trans former, t1, fi-cini cihm icfsc .n v^y useful dielectric media If FIG. 1 illustrates a switch tn a similar manner, when inierp'^d m electro,d npparmm Kiv'Cvii mculhc conduc.in c elements ihnt have a difference m potenii.il FIG 3 represents a rolled capacitor, FIG 4 shows a sectional view of a portion o( the during open'll ion of l!ic Tpparatu* became ih*y Are very electrodes and dielectric sheets of FIG 3, and xunic fiqiiiiU hich possesi pood dielectric strength, low FIG 5 is a aide new of a cable, the caatnc beinj partly po^fT factor and pood ohm rcsistmiy They arc par- tO removed in permu the interior of the parts to be seen ucinar v s.^iuble ,is liQuid imprcgnanK, in capacitor and The transformer illustrated in FIG I compnsci a eas- canfe martufic urc, as transformer coolant* and in the tnj I, core 1, coiit 3 insulated with manila paper, krafl fabrication nf swnch pear paper, cotton or other fibrout insulation, msulannc and Characteristjc* of the present ehloro-eihera are such cooling medium 4. lead-in bushings 5, and stniahle leads ai to render them particularly valuable as imprepnanti M 4 connected to the coil assembly. The insulating and for cdlulo&ic insulating materials It a known in the an th it impregnation of cellufosic material* eg wood pulp cooling medium m.iy consul of an ether such as 2-bui* oiyethy) 2-chlorophenyl ether which may tic employed as puper cotton, cotton fabric. cellulose ncetatc fibers and such or m combination with a highly chlorinated biphenyl textiles, hv cert-un liquid dielectrics provides an insul.it- aueh as "Aroclor" tmanufactured by Monsanto Chcmiie) mp 'nAicrinl ulrch hM a dielectric constant which ts much 80 Co., St Lotus, Mo ) These two components may be hiptier ilun ihnt of either (he eellulosic material before >ui|>rcgii,uiun or of the liquid dielectric Some of the employed in proportions such as from 50'/b to 90% by weight of one or more of the present ethers with the r>rM liquids used for tins purpose were mineral oils. 1 he balance being I he Aroclor Liquid hydrocarbons or other dielectric xiTfifurih of oihimprcgnated paper having been helogtnaled hydrocarbons or mixtures thereof may also reporicd by Rat Icy (Radio Engineering. 17 17, 75 (1&77)) *8 be used >n combination wtih the alkoxyaUyl chlorophenyl to he 15 time* as high as that of the otf alone Howeve- because mineral oils are readily oxidiud. their use* ethers as dielectric media, e g , petroleum oil. halogenated compound* of naphthalene, toluene, benzene, nttrobi- fulness as insuKuing media and .n impregnating agents phenyi or diphenyl ox.de for eellulosic natcn*ls h.is been tjmned in that exposure The twitch shown >n FIG 2 comprises a cuing 7, to air, sunlight or moisture often leads to gas formation, gaseous loni/jition und formation of wax These change* fixed coni nets I and 9, and movable contacts It and II which cooperate therewith The movable contacts are ,>flcci power facior stability mounted upon a support 12 which in turn is operatively Although wood pulp paper, alone, has good mstdaimg connected to actueting levers 13 A suitable .rc-queocO- properties, u is also affected by exposure to nr, panic- mg liquid which may be used in thtt device, either as the ul.iriv at higher temperatures While the rale of me' 43 sole dielectric, or in combination with a minor propor cl'-1meal deterioration ts reduced by impregnating the non of a petroleum oil or u halogenaicd hydrocarbon insulation with oil, this wai of little advantage as noted siiiovc Accordingly. U* art resorted to other impeeg- such u highly chlorinated biphenyl, it 2,butoxyethyl ethyt-ar-ietrachlorophcnyl ether or ar-bist J buioxyeth- na^ng agents, particularly the highly chlorinated iro o*y )eihyl-ar-triehlorobenzene ns,itic hydrocarbons The** muienoJi have dielectric Ad The capacitor shown in FIG 3 it made up of alternate stiengihs which are higher than those of the mineral oils fn addition, they are non^Aammahle and more stable to the influence of air. moisture and light How- layers of metal foil such u aluminum or tin foil sepa rated by sheets of dielectric material FJG 4 shows a section of one turn of the finished rolled capacitor dins iver, their general utility has been somewhat hampered trating the alternate electrode* and dielectric layers De tn th.ii under High operating temperatures and voltage* M tails of the construction of the paper capacitor are set uetompoMiion wf Hud highly chlorinated hydrocarbons forth licrc by way of illustration. i* ,ii,inifcMad .Hydrogen chloride it evolved, and this Him sheds of tissue paper (preferably kraft capacitor Attars not untg the paper which had been impregnated, tissue) are stacked upon each other, and a thin aluminum but .iNo the mesa) portions of the capacitor foil (about 0 0003" m thickness) is laid on the top sheet Tlic presently provided atkoxyalkyl chloroaryl ethers 00 of tissue The foil is then covered with three more ate ligh-liothng materials which possess high resistivities and luw power /nclors (heir mahiJiiy to high tempera* sheets of the tissue and another sheet of the foil i, placed thereon so that the (wo sheets of mclat foil are Separated turc* i* evidenced by ImJe or no change in power factor rc iitiri.ifier healing for 24 lioura m 100* C Tlicir from each other by the tissues On the second metal sheet there are slacked three more sheets ot said tissue s-'.ibi.wv further jllustraicd by continued high resistive 05 and tbc stack of alternating layers of metal foil and ijcs which mdic'iic* freedom Tiom conducting ion* tissues thus obtained is wound into a cylindrical roll winch would he present if decomposition of the ethers This is placed in a con lamer, and at this point elect ne.d ocuirnd 7 he present cl lien remain liquid at low tern- connecting means, e g . wtic or bar conductors, depenu pu'diuic'i vjiercny there is avoided a decrease in dieiec* mg upon the size of the assembly, may be connected 10 triL cimsuiu due to freezing of the dipoles 70 the metal foil in known manner After drying, prefer Titc uuovc characteristics thus speak for eminent suit' ably m a healed vacuum oven, one or more of the pres ability of the .tikoxyalxyi chloroaryl ethers as impregnat ing agents for eellulosic material*, and an embodiment of ent atkoxyalkyl chloroaryl ethers it added to the con tainer m a quantity sufficient to impregnate thoroughly the present invention is the provision of improved cellu- (be paper content thereof. The container is then scaled losic insulating agents comprising porous materials derived 75 Alternatively, and particularly in the manufacture of HONS 201748 -B,BM,70 7s Muill rcmtori wbidi for the sake or economy are boused butoiycthyl 2-ctUorophceyf ciher, D P C /! mm in paper tubes rather titan in leak-proof container!, the *on 1.5022 bated on (he recovered dichlorwbcrucnt. nisuc paper is impregnated wilt the aikoxyalk)! ehloro- The nuantity of taid ether obtained repre'-enu a cun nryl alien previous to inierlcevinc with the metal foil in veruon of the dtchiorobcnzcne comumcd n the tcdciivn the manner described above * The invention is further illustrated but not limited by Eiwmpit 3 ihe following examples Tku* example describe* the reaction of ^f,viHch!orn Ei iniip/r I benzene w*ih 2*t>uioiycthanol A minure conM\"nt of 294 5 42 molet) of ihe tUchlornheorene g () imiliM \ miKiurc consisting of 2 moles (294 p 1 of ortho-di- 10 or the buloxy cib.-moL 114 c <33 molo) of pot.^uum hy clilnrobcnreue 2 moles (334 ) of 2-butosyeihano). 2 3 droinle, and 100 ml of toluene w charged lo *i Hasli moles (100 g) of lodiuni hydroxide and 140 mr of equipped with a mirrtr, ihemuxncicr ami column bearing toluene ss-is brought to a icmpcr-iiure of 140* C within a head for take-off of the dmillaic h w;n he tied *. a penod of 43 minutes, and Ihcn maintained .i a tempera- temperature of from 154-1M1 C. for about I hour* dur lure of from 140* C to ITS* C for 4 lioun. During this If mg which itmt 76 ml of wotcr wiu collccicd The r--jc period 30 0 ml of waicr was collrcied in a Dean-Stark non miRhirc w%% theo rtAuftcd with 1500 mi of writer water trap Carried on a condenser with which Ihe reaction aod 100 ml. of ioIum# (or one hour U wj< ihcn *flr*wcd vessel was equipped The cooled reaction mixture wat to cool and indificd whh JA mi of conccntricd hydro domed wnlt 400 ml of ether and washed neutral with chloric ickI It wt* theo Altered and the rcuduf wii a dilute hydrochloric acid Distillation of the washed gg >ashed with water and treated with alcohol in order in material pave 250 g of a fraction, BP 40-100* C at affect atratsAcMsoo The organic layer which formed 2(3 mm , the chlorine analysis of which showed n to ba was separated and distilled first at a prtvsurc of 23 -30 essentially dtchiorobcnzcne. and 257 2 i of the substan mm of H| to ramov* water and then so obtain 13 3 | of tially pure 2-butoiycthyl 2-chlorophenyl ether, B P the substantially pure 2-butoxyethyl para-chlorophenyi 124-130* CJ1 mm . n0" 1.5022 and analyzing at fol M ether, B.P. 170-110* C./23-30 mm, n0" 1 3021 and lows aaalyMf ae lottows Found Calcd for CitH|iOyCl Found Calcd. for CtHiiClO| Percent C................ .......... 25 *3.00 Purceat C 43 57 43 oi Percent II --.---------------- 7 51 7 45 Percent H.. 7 37 7 sf Percent Cl...--...___ _ 13 35 15.37 w Perceat a........................ 14 71 13 50 Based on the recovered dJchlorobemene the yield of 2- Example 4 buioxyethy) 2-chtorophenyl elhcr obtained represents ap proximately 1294 conversion of the dtchiorobefifene to Into a 3-liter flaik equipped with a stirrer and a column which earned a Dean-Stark trap there were charged 4 1 the said ether The 2-butoxyethyl I-chloronhenyl ether thus obtained was found to have a volume reaisliviiy o/ 33 X10* ohmcm at 100* C,, a pour-point of minus 70* C., and iht following dielectric constant and power factor values at the frequencies and temperatures noted below - II moles (70fi g.) of 2-Nitoxyeihanol, 4 23 moles (254 g ) sodium hydroxide. I moles (1431 2 g) of 3,2,4-tnchlorobenrena and 200 ml of toluene The temperature of the reactKm mixture was brought to 153* C within about I hour at tha and of which period the collection of water was noted to the trap Healing was continued at a tem- peratlira of from 133* C. to I go* C for about 3 hours Tk nMWTQe MMiM I fowT Mv, prml during which time a total of about 112 ml of waicr was 1 owner. 1 ** -sre wr r m*c. 1 Mrc ! id am am i a in ft l tsr ii ** ftjl * ft i 9*9 ** collected. At this point an additional 0 23 mole of the 2butoxyethanol was added and heating was continued for another It hoars at a temperature of from 110* C to >40* C- After being allowed to cool to room temperature tha traction mixture was acidified by addition of 30 ml of concentrated hydrochloric acid It was then diluted The low power factor values at both teat frequencies with 1230 mi. of water and allowed to stratify The or and ft the three teat temperatures show very food liability -- game layer which separated was washed 4 times with 100 of the 2-butoxmhyl 2-chtorophenyl ether Paper capac cc porta--* of dilute sodium hydroxide, several times itors in which the present ether is employed for unpnpnat- with water and finally with brine The washed product inf the paper and particularly useful m high-altitude air wat haatod to 43 * C./22 mm to remove water Further craft m tut they my ba used without treexmg of the dmillxtna gave 1000 g. of the lubstanually pure 2-n- dipcJes at temperatures which appraximata ths very low boloxyetbyl dseMorophenyl ether, B.P. 117-131 * C /20- f-- poiat of this eshar. ** 22mm. and20.1 g.of bu(2-e-buioxyetbyl)chlorobenzeac. BP. 144-173* C./20-22 mm. A (reckon. B f. 117-120* Example 2 C./20-22 am. up* IdlM analysed aa follows This example showi the use of an exeats of ortho-dichlorebenxeae in the preparation of 2-butoiyelhyl 2chtorophettyi ether from ortho-diehk>robcnzene and 2butoxyetheool Into a reaction vessel equipped with stirrer end a column carrying a Dean-Stark trap there wat chirped 1 5 moles (177 g ) of 2-butoayeihnnot. 4 ) moks (441 5 g ) of ortho-dichlorobcnzene, 11 motel of sodium hydroxide and 200 ml of xylene Hestihg of he charge si a temperature of 150* C to 190* C. for # hours resulted tn collection of about 27 ml of water tn ihe Deen-Sterk trap After atlowing the reaction mixture - Found Calcd. for CnHieCisO] y Fervent C...................... 54 71 34n Pureere H............... 6 27 413 Fervent Q........................ 24 13 2493 The diether. B.F. 1*4-173' C./20-22 bus analyzed as follows.' . 4* Found Calcd. for CuHwClO, Percent C----------------------41 51 42 eg Percent H____ ________ 7.32 141 Percent Cl.______ _____ 12 42 10.21 to cool it was diluted with about 200 ml of water neutraliicd with 33 ml of concentrated hydrochloric acid Id Example 5 (equal to 0 31 mole of llCl) and finally washed with Thu example describes tha reaction of 2,4-dichlorotolu- waicr The aqueous layer was extracted with ether and ana with 2-butaayethanol. To a 4*aeck. 1 liter disk the ether extract was distilled to give 341 g. o( a fraction, equipped with a stirrer, thermometer and column hear B I* 75-SO* C./23 mm., which comprised unreacted di ing a taka-off head there was charged 2 mole* (322 g ) chlorobenzene and 233 | of the substantially pun 2- Tfi of 2,4-dscMorMoitme, 3 moles (334 g) of 2-btunxy- | M0NS 201749 r') Q i 9 clhinol ("Tiulyl Ccllotolvc"). 3 moles (111 | ) of poi. 10 ANALTIIH--II MU'11 hydroxide and 100 ml of lokne Tbt mixiure was Found Cekd (orCj^i,,CJ,r\ heated wait tliranc (or about I houn at a temperature Percent C______ _______ 53 44 of from 160-101" C , during which time 71 ml of water v as collected At the end of the healing period 1300 ml of water was added to the mixture with stirring and the | Percent H_ ________ _ Percent a________ ____ *91 26 15 5445 703 2416 wiotc wav acidified with 100 ml of concern rated hydro Rued on the sharped pentichifirocihylhenrcnc there elilorie nod I ilir.attein of itic xtiitdic.i mixture pare a waa obtained a 71 6% i novel mm lo the innno-rtlier and filirue from whu-11 the ore inn. 1 O'er .i arpamicd and a 4 P'1 conversion in ih* <1. ,! Cor water w. iclwd After removing Ihe water hy heating to 10 Testing of the clcttra-al prupcrths n((t),ic 2-huluxr- 65' C /JO ami the remaining material waa distilled 10 five lot [ of the auhnantially pure (I) 2-butoxyethyl ethyl etbyl-ar-tetrachlorophcnyl el tier save a volume r*. antivity value of 50x10* ohen-cm. at 100* C, and the ar-ehlofotolyl ether, B P 170-15" 010-25 mm it,,* I 5023 which analyzed at ahown below, and 59 g. of (11) followTMp dielectric constant and power (actor velum at the frequencies and lamperatarae ahown below bnttiutOxyethuxy)tolucne. BP 220-240* C/0.2-0,3 }g mm , nD** 1 5006 analyzing aa ahown below Percent C __ . Percent H____ Percent D____ AKALTglg--I Found Caied for CiaHisOsCl 64 32 7.19 14.61 ** IWltdt to *0. uro VC. nr v tft lift Mf iM u ti 1 14 IN t ft AJtAi.ll)*-- 1) Found Percent C_____ Percent H_ .. ................ 2i Calcd lorCieHoO, 70.33 . *.44 The low power Iacton shown above at both the ten frequencies am) both the teat temperatures, together with (ha volume rsantmty value ahown above attest to very pood atability of (ha 2-butoeycthyl elhyl-er leirachloro- Example 6 phenyl ether. Paper capacitors prepared by imprcpnai- Tbit example deecnbea the reaction of 1,4-dichkxotolw cne with 2-butoxyctbanol ("Butyl Celloeo!ve"), A mu- 4 M ing krsfl timui paper with impregnated items between (his ether, interleaving the thirnmum foil, and rolling lure consisting of 2 motes 012 g.) ol 3.4-dschlocotoiucue, 3 molet (354 g ) of the butoxyethaaet, 3.3 moke lbs interleaved amembly wen useful ti temperatures of down to about minus 40* C. which n the solidifying (185 p ) of poiiufum hydroxide aad 100 ml. of lotuena point of (I). wai heated with itimni at a temperature of from 164 Testing of (If). t.e. the ar-btt(2-buioiycthoxy)e<hyl- 167" C. lor about I hours During flat um 7* mL of water was collected in a take-off bead attached to a col M ar-trichtorohenzcna also gave good rernlu, the dielectric eonetant of (II) bang 5 4 at both 10 kc and 100 kc umn with which ihe reaction vessel was equipped At when teetod at 25* C. and 4 4 at both 10 kc and 100 kc the and of the haotinp period 1500 ml. of water wae added to ihe reaction mixture and the whole waa acidified with 85 ml of concentrated hydrochloric acid end At- 41 when tested at 100' C The power factor at 100 kc was found to ba 007 at 2S* C and 0.1 at 100* C Because (II) ha* a aohdifyinp point which is approximately that fered The orgaaic layer which formed in the filtrate of (I), a mixture of (1) and (U) may he employed as wai separated and washed with water. After removing the water hy heating lo *5* C./25-30 mm. (ha residue the impregnating agent in the manufacture of paper ca pacitor*. wat distilled topivt 3)4g. of the tubetaotially pure butoxy- Although the pnaaat ethers an particularly useful a* ethyi ar-chlorotoiyl ether. B P. 175-1*5* C/20-33 mm. - Impregnating agents far cellulose: materials adapted for and analyang aa follows: * naa as dielectric*, bscanst of their very good electrical psopsrliw (hair thermal stability and their ability to re Found Percent C.......................... *4.4* Percent H.......................... 1.07 Percent Q........... ............ 13.0 Calctf. tor CuUmOiCI *4.32 7.1* 14*1 mail liquid ai low temperatures they an of genera! utility a* liquid dialarfrin They era likewise very sdvanta. 0*om)y employed aa functional (nidi, e-g., aa heat-trinafer media end aa hydraulic fluids. Throughout the ipeeiBcation and claiiM, the prefix ar when mod in naming a chemical compound denotes at A nuxturs coMtattog of 4 molee (472 g.) of 2-hutoiyethanoi. 2 molaa (554.12 g.) of ar-ethylpantaehlorobea- tachment of Ihe radical or element winch it precedes at u an aromatic ring carbon atom, rather than at an aliphatic cans, U aotoa (100 p of sodium kydrouds and 100 ml. ** carbon. )1 is employed whenever the exact position on ol lalaana Was hasted with stirring at a temperature of the li raises ring at which tbt tubatitutioa occurs a un up to 190* C for 2 hours, during which lima 45 mL of known. water of reaction was collected, and than batted for 5 This application a coniiiHianon-in-part ol my eo- more houn at a temperature of 170* C. The whole waa ,, penthnp application Serial No 550,239, tiled November then cooled" to 10* C, diluted with 500 ml. of water " . 1*55 and now FatsM No. 2,913,499. and neuiralized with hydrochloric add. tt waa than diluted with ether and the organic layer which formed What I claim is 1. Electrical apparatus comprising, in combination, wai separated, made alkaline, and waabed to nautral. Distillation qf the washed materiel ga*e 5*0 p. of (I) metallic conducting dements disposed in spaced relation ship to each other and adapted during operation of the 2-butoxyeihyl ethyl-ar-tetrachlorophenyl ether. B.P, 170- apparatus to have a difference in electrical potential there SO* C /Q 7 mm , nD** 1 5324 inalyzinp as ebown below between and. interposed between said elements for insu and (II) 61 p. of ir-bii(I*butoxyeihoiy)tihyl-ar-cneUi- lating on* from the ether, a liquid dielectric medium coo- robenzene. BP 205-217* C/0 4-10 mm, *b" 1.5072 storing meettially of aa etbar of tbe formula ' and analyzing aa shown below. 4>AL.nxe--i Q-toiCdd.oai. Found Percent C4751 Percent H 5 2* Pcrcmit a_________-- j7j* Calcd. tor CmHmOsO) 4*.5* 5.02 j n c in which & is aa alkyl radical of bom I to 5 carbon MOMS 201750 3,aaa,j87o 11 atoms, ' n an integer of from 0 10 4, tn it in integer of 12 insulating agent associated with each of the electrodes and from 1 lo 2. K' is an alkyl radical of from 1 to 8 carbon isolating them from each other, said insulating agent con moms, i is an integer of from 2 to 4, and n n an integer sisting essentially of the dielectric composition defined in of from I lo 4 claim 2. 2 A diclccmc composition consisting essentially of k j 4 A capacitor comprising a pair of electrodes and an rclliilosic malcrul impregnated with an etber of the insulating agent associated with each of the electrodes formula and isolating them from each other, said insulating agent consisting essentially of a cctlulosie material impregnated with 2-taiitoxycthyl 2-chlorophcny! ether 5 A capacitor comprising a pair of electrodes and an insulating agent associated with each of the etectrodes and uolatiog them from each other, said insulating agent consisting essentially of a cellulosic material impregnated ,n which R is an alkyl radical of from 1 io J carbon with 3-butoxyelhyi ar-ethyl-ar-tetrachlorophcnyl ether atoms, r it an integer of from 0 to 4, m it an integer of from 1 io 2, R" is an alkyl radical of from 1 to carbon aioms, jr it an integer of from 2 to 4, and n u an integer of from 1 to 4 3. A capacitor compnaing a pair of alactrod** and an W Sdmaesa Cited in the Ale of this patent UNITED STATES PATENTS 2J64,314 Roes et el.-----------------------Ad*. 14, mi 2,703,(35 Real eL----- ,,------- - Pah. 22, 1955 HONS 201751