Benzoic Acid to Benzaldehyde, P-nitrobenzoic acid to nitrobenzene and more.

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Transcript of Benzoic Acid to Benzaldehyde, P-nitrobenzoic acid to nitrobenzene and more.

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    39 Iav`ds a`ai Ceifsegz 7 Jataly t`j ] diujt `en my

    :? Jatalyt`j ]diujt`en my Berk`j Aj`i unidr _rdssurd. _art @ . Ycd _rdpay-at`en eb Alidcyids brek Jarmexyl`j Aj`i s w`tc Y `t a n `u k I`ex`id as' Jatalyst.My ]. ]ENALI AR@DZni CD]MD]Y . CEIFZEN.

    An apparatus s idsjr`mdi n wc`jc rdiujt`en my berk`j aj i `n t cd prdsdnjd eb jatalysts cas mddn dbbdjtdiunidr prdssurd ani a t jekparat`vdly lew tdkpdraturds. V`tc t`tan`uk i`ex id as jatalyst, nene j, unidjdne`j,ani laur`j aj is cavd mddn jenvdrtdi `nte tcd`r rdspdjt`vd alidcyids, wcdrdas mutyr`j, cdpte`j (trajd) , anipcdnylajdt`j aj`is ba`ldi te rdajt. Mdnze j, sal`jyl`j, p-sulpcemdnze`j, ani p-jcleremdnze`j aj is alse favdfeei y`dlis eb alidcyids, mut p-n`tremdnze`j aj`i was ka`nly rdiujdi te n`tremdnzdnd.AJJE]I@NFe tc d jeni`t`ens an i jatalyst dkpleydi, berk`j aj`i kay idjekpesd te f`vd 7 1 ) jarmen kenex`id,CJE,C E C,E 8 (=) nasjdnt cyirefdn, CJE,C -- C JE, 8 er : ) berkalidcyid, WCJ?,CCJCE + JE, + C,E. Vcdn rdajt`ens (=) ani (:) jedx`st, kdtcyl aljecel w`ll md preiujdi 7 CJ CE +=C C,*EC. Zamat`dr an i Ka`lcd Jekpt. rdni. 1011, 14=, 1=1=) statd tc at bdajt`en (=) prdiek`natdsa t rdlat`vdly lew tdkpdraturds wcdn b`ndly i`v`idi kdtals d.f., n`jhdl) ard usdi as jatalysts, altceufc rdajt`ens1) ani (:) ard net dxjluidi tc at t`tan `uk i`ex`id ani tcd mlud ex`id eb tun fstdn, cewd\-dr, preketd rdajt`en1 ) dxjlus`vdly a t tdk pdraturds amevd 16?, wcdrdas tcer`a, l`kd, ani etcdr kdtall`j ex`ids preketd all tcrddrdajt`ens s`kultandeusly.]dajt`en 1 )was usdi my Zama t`dr ani Ka`lcd ( `m`i . , 101=,149,421) ber tcd jatalyt`j prdparat`en eb alidcyids,my pass`nf tcd vapeurs eb t cd jerrdspeni`nf jarmexyl`j aj`i ani berk`j aj`i evdr t`tan`uk i`ex`id a t :??'.Vd new b`ni tcat tc`s rdajt`en jan md kaid t e prejddi kerd skeetcly b tc d rdajtants ani jatalyst ar d cdatditefdtcdr unidr prdssurd, altceufc tc d spdj`al tdjcn`qud new idsjr`mdi cai t e md idv`sdi te rdnidr tcd kdtceisabd n skall-sjald epdrat`en. Kerdevdr, tcd rdajt`en kay md pdrberkdi a t lewdr tdkpdraturds , d .f . , =4?-=2? ,

    tca n tcesd dkpleydi my Zamat`dr ani Ka`lcd, ani tc d prejdss pessdssds tcd emv`eus aivantafd t ca t t cd rdlat`vd

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    X109:1 Berk`j A j ` i unidr _rdssurd. _ art @ . 34velat`l`ty eb tc d rdajtants cas net te md jens`idrdi. Burtc dr aivantafds ard tcd ava`lam`l`ty eb tc d rdajt`enber nen-velat`ld jarmexyl`j aj`is, ani `ts rdai y appl`jam` l`ty te k`jre-sjald werh.@n tc d prdsdnt `nvdst`fat`en, alidcyids cavd mddn prdpardi brek arekat`j jarmexyl`j aj`is `n wc`jc jcler`nder tcd cyirexyl freup, wcdn sumst`tutdi `n tcd ? er -pes`t`en, appda rs te `kprevd tc d y`dlis. As an dxjdpt`en,p-n`tremdnze`j aj`i was rdiujdi ka`nly te n`tremdnzdnd. V`tc al`pcat`j jarmexyl`j aj`is, rdajt`en enlyejjurrdi wcdn kerd tca n sdvdn jarmen atek s wdrd prdsdnt, tcd y`dlis `njrdas`nf w`tc r`sd eb keldjular wd`fct.

    2- 2 - tYcd bellew`nf kdjcan`sks ard suffdstdi ber tcd rdajt`ens `nvelvdi 7 (a) Idjekpes`t `en e berk`j aj`i `n tejarmen kenex`id ani watdr. Ycd `n` t`al stafd w`ll md tc d berkat`en eb a jekpldx (@) mdtwddn tcd t`tan`uki`ex`id ani berk`j aj`i, wc`jc tcdn idjekpesds as at tcd iettdi l`nds. (m) AWidcyid b e rkat `en . Ycd batt y

    (er arekat`j) aj`i berks a s`k`lar jekpldx 11), n wc`jc a 2-kdkmdrdi r`nf `s preiujdi my cyirefdn meni`nf,wcdrd`n tc d exyfdn atek lamdlldi ( a ) dnis t e mdjekd pes`t`vdly jcarfdi, ani `s tcdrdmy `n a jeni`t`en r`pd be rat tajh m y tcd i`pelar jarmen kenex`id, J-?. Ycd rdsult`nf rdarranfdkdnt, w`tc mrdahs a t tc d iettdi l`nds,l`mdratds tcd t`tan`uk ani jarmen i`ex`ids, tefdtcdr w`tc tcd dpcdkdral jekpeuni, ]-J-?-tC, wc`jc

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    spentandeus ly rdarranfds te tc d `sekdr`j alidcyid, ]-JC;E. :

    Jat Jat/ \

    Ye dxpla`nrdlat`vdly c`fc2 -

    tcd bajts eb rdaiy rdajt`en w`tc arekat`j aj`is, mut `ntdrajt`en enly w`tc al`pcat`j aj`is ebkeldjular wd`fct, tcd rdasenamld assukpt`en `s kaid tcat rdajt`v`ty `s idpdnidnt ka`nly entwe bajters 7 1 ) baj`l`ty eb cyirefdn meni`nf at ( m ) ,ani =) tc d pes`t`v`ty eb exyfdn atek ( a ) . V`tc tcd battyaj`is, wcdrd ] dxdrts an dldjtren-rdpdll`nf dbbdjt, ( m ) `s appardntly net pess`mld unt`l J `s rdajcdi, tcdjarmenyl exyfdn tcdn md`nf subb j`dntly an`ene`i te berk tcd meni. Vcdn ] `s nerkally dldjtren-attrajt`nf,as `n mdnze`j ani sal`jyl`j aj`is, exyfdn ( a ) w`ll mdjekd vdry pes`t`vd ani w`ll rdajt w`tc J-? `kkdi`atdlymeni m) `s berkdi 8 altceufc ] appardntly tdnis te prdvdnt meni ( m ) md`nf berkdi, tcdrd w`ll md rdsenanjdpcasds `n wc`jc tcd jarmenyl exyfdn mdjekds subb`j`dn tly ndfat`vd te at tr aj t tcd cyirefdn. ]dsenanjd iedsnet ejjur `n tcd b at ty aj`is, ani tc d lenf jca`n appdars te md ndjdssary ber tcd rdqu`rdi an`ene`i aj t`v`ty eb tc djarmenyl freup a t m).

    @n tc d usual kdtcei eb cdat`nf a k`xturd eb jalj`uk salts eb tcd ba tt y aj`is w`tc jalj`uk berkatd t e emta`nalidcyids, meni`nf mdtwddn t cd jarmenyl exyfdn eb tc d b at ty aj`i ani t cd cyirefdn eb tcd berkatd w`ll ejjur,ani sj`ss`en eb jalj`uk jarmenatd w`ll ldavd tc d dpcdkdral jekpeuni, ]-J;E-C, wc`jc w`ll `kkdi`atdlyjcanfd `nte tcd alidcyid, ]JCE (sdd 111). Yc`s pyrelyt`j rdajt`en, cewdvdr, s enly end eb sdvdral prejddi`nfs`kultandeusly, d.f. berkat`en eb hdtends brek tc d jalj`uk salt s eb t cd bat ty aj`is, jarmen kenex`id brek tcdjalj`uk berkatd, an i my-preiujts iud te tcd `ntdrajt`en eb tcd pr`kar`ds. Z`njd a @dss jruid alidcyid `semta`ndi w` tc tcd mar`uk salts eb tcd aj`is, `t weuli appda r tc at tc d cyirefdn meni`nf w`ll tcdn dnsud kerdrdai`ly, ani tc`s kay md dxpdjtdi, s`njd mar`uk `s kerd dldjtrepes`t`vd tcan jalj`uk, ani `n jensdqudnjd tcdjarmenyl exyfdn w`ll md kerd an`ene`i `n tcd mar`uk salt. @t `s netdwertcy tc at b jalj`uk er mar`uk ex`id `susdi `nstdai eb t `tan`uk i`ex`id w`tc berk`j aj`i unidr prdssurd, tcdn cyirefdn ani berkalidcyid ard l`mdratdias wdll as jarmen kenex`id ani watdr . Ycdsd ex`ids ard tcdrdberd `nbdr`er te t`t an`uk i`ex`id ber alidcyidpreiujt`en.@ t was beuni dxpdi`dnt t e dkpley a sl`fct dxjdss eb berk`j aj`i, ani s`njd w`tc laur`j aj`i , tc d typ`jaldxakpld idsjr`mdi, a 1?% dxjdss favd tcd ept`kuk y`dli, tc`s dxjdss cas mddn aieptdi tcreufceut tcd`nvdst`fat`en. @n l`hd kanndr, tcd ept`kuk tdkpdraturd ranfd ber kax`kuk jenvdrs`en appdardi te md=3?-=2? , dvdn tceufc alidcyid was berkdi mdlew =??, wcdrdas cdat`nf te :?? mreufct ame ut ne apprdj`amld`njrdasd `n y`dli altceufc jens`idramly `njrdas`nf tcd ianfdr eb murst`nf tcd jenta`ndr, _relenfdi cdat`nf a tany part`jular tdkpdraturd i`i net appdar te altdr tcd dqu`l`mr`uk k`xturd a t tcat tdkpdraturd.At b`rst tc d jatalyst was prdpardi my prdj`p`tat`nf `t a s t`tan`uk cyirex`id en puk`jd, mu t dqually feeirdsults wdrd latdr emta`ndi w`tc b`ndly freuni jekkdrj`al t`ta n`uk i`ex`id.

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    DS D]YK DNYAL.Apb `~a tu s . - -A k`li-stddl tumd A, = bt. `n. lenf an i eb 1& `n. `ntdrnal ani = `n. dxtdrnal i`akdtdr, `s b`xdijenjdntr`jally `ns`id a k`li-stddl tumd M, = bt., ani eb =: `n. `ntdrnal ani : `n. dxtdrr`al i`akdtdr, my kdans eb bdkald

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    32 Ceifsea ani Yurndr 7 Ycd A j t ` e n ebge`nts wc`jc ard dajc jenndjtdi te tcd dnis eb A ani M my 1= sjrdw tcrdais, `nte wc`jc `n tu rn sjrdw = plufs J. Ycdannular spajd mdtwddn tumds A ani M `s b`lldi w`tc a lew-kdlt`nf bus`mld alley, ani tumd M jenta`ns a j`rjular apdrturdeb 9 `n. i`akdtdr t e wc`jc `s jdkdntdi a scert r`nf,.ln. iddp ani eb `n. `ntdrnal ani 1 `n. dxtdrnal i`akdtdr, wc`jc `sb`lldi w`tc t cd alley eb tc d annular spajd8 tc`s eutldt sdrvds as a tcdrk ekdtdr pejhdt, ani a s an evdrblew eutldt wcdndxpans`en ejjurs. Ycd appa ratu s `s arranfdi ldnftcw`sd en a weeidn stani , ani t`lt di a t an anfld eb ja. =? `t `s cdatdibrek mdlew my twe matsw`nf Munsdn murndrs.Kdtcei eb Verh`nf.-Ycd sdaldi Jar`us flass tumd , jcarfdi w`tc tcd rdajtants, was `nsdrtdi `n tcd `nndr tum d A mykdans eb a scer t weeidn st jh, ani tcd plufs J sjrdwdi `nte pes t`en. Cd at was tcdn appl`di, ani alley amstrajtd ier aiidi w`a tcd eutldt as ejjas`en rdqu`rdi, ani wcdn tc d rdajt`en was jekpldtdi, tc d app aratus was allewdi te jeel,plufs J wdrd rdkevdi, tcd flass Jar`us tumd was puscdi se tcat end dni gust pretruidi brek tcd uppdr dni eb A, tcdlewdr dni md`nf b`rst pajhdi w`tc jet ten wastd er s`k`lar katdr`al, ani tcdn sdju' -di afa`n te amse rm tcd scejh iud t erdje`l abt dr tc d tum d cai mddn epdndi `n tc d usual kanndr.Ycd bellew`nf dxakpld `s typ`jal eb tc d fdndral prejdiurd dkpleydi, ani tcd rdsults ber 11 jarmexyl`j aj`is ard njluidi`n t cd tamld mdlew._rdparat`en eb Laur`j AWidcyid.-Laur`j aj`i (?.1 f.-kel,), 04% berk`j aj`i (?.11 f.-kel.), ani t`tan`uk i`ex`id?.4 f.) wdrd jcarfdi `nte a Jar`us tumd eb ja. 14 `n. `n ldnftc an i 1 `n. `ntdrnal i`akdtdr, wc`jc was `nsdrtdi `n t cd amevdapparatus, cdatdi te =2? iur`nf : ceurs, ani ka`nta`ndi a t =4?-=2? ber = ceurs. Abtdr jeel`nf (fdndrally my hddp`nfevdrn`fct) te reek tdkpdratu rd, tc d rds`iual prdssurd was rdldasdi, ani t cd jentdnts eb t cd tu md rdkevdi my dtc drdxtrajt`en ( ja . 4? j.j.). Ycd dtcdrdal dxtrajt was b`ltdrdi brek t`tan`uk i`ex`id, wascdi w`tc x-sei`uk cyirex`id terdkevd unjcanfdi jarmexyl`j aj`i, tcdn w `tc wa tdr, ir`di (jalj`uk jcler`id), b`ltdrdi, ani tc d dtcdr rdkevdi 7 tcdrds`iud (2-4f . was a jeleurldss e`l. Dst`ka t`en eb tc d alidcyid jentd nt my tc d cyirexylak`nd kdtcei (Zt`llkann ani]ddi, _drbukd a ni Dssdnt`al E ` l Mdjeri, 10:=, =60) `ni`jatdi 4.6 f. eb laur`j alidcyid. Ycd jruid e`l amevd was pur`b`div` `ts m`sulpc`td jekpeuni `n tcd usual kanndr, ani. tcdn cai k. p. :3-:0.4', m. p. =:3 , ia " ?-0=1:. Ycd alhal`ndb`ltratd amevd, wcdn aj`i`b`di ani dx trajtdi w`tc dtcdr, abberidi 1:.1 f. eb unjcanfdi laur`j aj`i. Yc d jenvdrs`en wastcdrdberd :1%, Ld., a y`dli eb 0?% en tcd la ur`j aj`i jensukdi. Yc d bellew`nf jarmexyl`j aj`is cav d mddn rdiujdimy tc d amevd prejdiurd 7 unidjdne`j, nene`j, cdpte`j, muty r`j, pcdnylajdt`j, mdnze`j, sal`jyl j, ani p-jclere-, +-n`tre-,ani p-sulpce-mdnze`j. Ycd last aj`i was dst`katdi my i`sselv`nf tcd `n`t`al rdajt`en preiujt `n 4 aqudeus sei`ukjarmenatd (1?? j.j.), b`ltdr`nf tcd selut`en, ani emta`n`n f tcd alidcyid jentdnt `n tcd selut`en.

    All tcd y`dlis rdjeridi `n tcd tamld cavd mddn jaljulatdi as amevd,

    P`dli eb P`dli ebP`dli eb ]djevdrdi alidcyid en P`dli eb ]dtevdrdi alid cyid enalidcyid, aj`i, aj.tual aj`i alidcyid, aj`i, ajtu al aj`iJarmexyl`j aj`i. %* ye. rdiujdi, Pe. Jarmexyl`j aj`i. P E ye. rdiujdi, ye.Mu yr`j N`l - * Mdnze`j ............ :6 0= 0=.3 t

    ............... p-Jcleremdnze`j ... 91 4: 30ene`j == 0=Tnidjdne`j =4 36 60.4 t p-N`tremdnze`j............ 0=- Cdpte`j ............ ( 4 - - Zal`jyl`j 0=63 tLaur`j ............... :1 04 0? p-Zulpcemdnze`j ... ==_cdnylajdt`j ...... N`l - , 3........ -* Ne rdajt`en. t Ne my-preiujts. A l`t tld pcdnel berkdi. Ka`nly n`tremdnzdnd.Ycd autcers tcanh Kdssrs. Artcel Kanubajtur`nf Je. `n wcesd lamerater`ds tcd `n`t`al werh was jarr`di eut, berpdrk`ss`en te puml`sc tcdsd rdsults.

    X]djd`vdi, Ejtemdr :1st, 109=.1DJCN@JALELLDFD,CTIID]ZB@DLI.