DEP0053352DA - Process for the production of salts of phthalocyanine dyes and their free phthalocyanine bases - Google Patents

Description

America "Gyanamid Company
30 Rockefeller 3? Laisa _s M # w York * IX »TStA ..

Process aaur manufacture yon gallows dey, Pft ^ alozyanin-

This lrfindUBg concerns a new fcO experience about salsa of the ensotetrasaporphinsf-dye © y ^ SXe commonly known as Pixtalo - he; rgi! Ssteile. ħÄÄiallea? commits »eich, die

on ®ia method »by which the Sal ^^ ö & aydrolyBier weräan, ttn ^ e ^ gm- ^ glo-aliribggHNsgaig ^ gläiä ^ l '^ B ^ i ^^

su generate oil '^ A ^^^^ iJ ^ icvu u ^ -

Me PliimloEyaaine besitaem aianolierx ¹ ©! id.oia.tig ©, forstige and siW hinöiolitlioii many color & toffeigensciiafteii her »

ge However, iacfcwe ^ wi ^ es ^ de laoliteile occur »woa ^ these f arrbs fcöf f θ uirfeei · fe ^ holdnib & en use fe will be,

when used in

The 'ürocknon of J \ nsti ^v ieh.compQ & itio "en who develop." Often has an unequal distribution of the ¥ oriiand © nen JPlgjaeat @ Bj ^ u |: * result. Pie ^ e loajagelliaft © Y Teilnag

durclx a ^ Ä ^^^^^ & ^ sa «« * rÄ * eÄ0 »aer colored dyestuff dividing provoked» u «Terden and egg» trookener filsi let often by «in tiBgl © iclmäi5 & ig0e _s mottled eye. @ ji · This influences the CHans »The evenness and the color value are negligibly overlooked.

Anatrichlcoia positions containing Mitx * © aelluloae,

tend, with the usual ShtfLlazyaxiija * » dyes, a particularly low-bodied <3S appearance. Unfortunately, some contain the

ü & t, Hu »öel« ä fiibroaellttloöej so

that the difficult as a result

represent serious -t'rubleift of l'ecimik »

OUWi ¹

trltt ^ aiclit pllein a be

^ on

de, r 'inconsistent

ondexsi it also eats. there&

the flaky

with the same / uastrioh & oinpositioxi under dung methods not constant «üS.B» i & t -saiimßsi & ailsag «when dip Änötrichkampotsition on öinen

much less than whom «, the blessing - nd -in

the same paint co-opoeition is dipped. In letatereai the pigment appears less colored and more cloudy in the ! Shadows «of both mias & n in some practical applications, some l'eilfieine © objects sprayed and other® dipped will*

TJFgriiHHS- / tjs? 'fi'-JtU''cik "^ foiigo · K'uaaeaM ^ Jliig ^ of (M

jatTO ^ dja ^ ma-aj ^ -aett-aiuf jail ^ BB. triHaae «^. It is that color particles auBaimaenf lie lakes or watch floolcig clench "Why ^ ₁ Ie Mch ω behavior let not το 11 clarified. Meanwhile, kaiin der ßrad ^^^ fl c-kigoa Btell * iia # diu * ch sole dene ftM ^ ttel exactly geiaeöööen w © rdeia _t some of which im

472 described Bind "iSine really satisfied--

Measurement of the degree carried out by a registering spectrophotometer «2.B. ^ a ^^ a_ßii _i M ^ liäl ± Ä ^^^ 3 ^ is «-44 © Ää-i ^ &

alli

liie lessaBg- the strength of the color through aas then gives a numerieehea measure of the degree of the ciderbeeser's loss of color value W3 ^ g £ u tests a

as a result of

see £ iitr © aellul © gselaekes using a flocculant Xupfer ~ fh1pälQgyaaiiae as a pigment can be 30 ~ 35? * weaker color for the infused pattern as violins for the sprayed pattern of the agglomerated or susaBmerigeflos6eiJ.en 'pigment particles are true

^ r many attempts were made * including the problem of

lignes this Yoreeiiläge consist in the Parbetoff with a Übersugösittel to iiberaiehea how

According to this method, the questionable part ₉ that the resulting product contains a small amount of color as a result of the larger amount of the substances used, and that the substance may be reactive in many cases and has properties of the can adversely affect final painting & enfcetattng «,

In the same way it has been suggested. " Certain distributing substance during the formation of the dye ύοϊ "of the? incorporation in © ine AnstrieniEOiapoBl tion. This method also suffers from the fact that foreign material is mixed with the dye because it is desiialb this solution ΐίΧτ the practice is not fully satisfactory »

Sq ßßßßßßßßös predominantly wai * fiiilier the problem of that it daduroli in aaaoiien cases

© became "that" ate at Beri ^ ier PhfelosiyaniJiQ used © _r the nioiit flooteig gusaiaiaenballen · Bi ^ se Method T # 3? öchlieöt the inwendwngsgabiet the gebriuoliliclien plimloayaninen country is not a © angeja®s & ene solution of i ^ oblents daj? "

The present invention relates to the production of courtship mats for the palpiß guanine in a very varied manner. This © Salae can be returned to Ph ^ log ^ anin-Bigmenteii hydrol ^ -

Then a tea for retirement against

and show none of the parts of the fragments which are coated with foreign substances became.

Yes, it has long been known that Pirmlosyanln-Pigoiente salified with strong acids. form able «Dae Piimlesyanin!» As a weak base, Pigaent can be used - this term in its theoretical and physical meaning - aixieis £ roton — Akaeptoi? S. will. Ber Ausdruete is not gebr IMD in the sense & u tit _f ma product au mark & giehnejifi daa SiOH sehneil ionized water in a pB results leutralwert above. Around PhtalosjaELin-Jäolekül there are β Btictetoffatome and one can therefore take it that way _? that it behaves against strong acids like a strong baae *

In the past, the phthalates of the Phthaline plant were made by oiling the pigment after its isolation and removal. with celebration centered? aqueous acid or with acid In. Absence of organic means of disarming hergeetelXt. Senn this§ were hydrolyzed, would be the resulting

not in atisreiciasiiäem ÜL & ße against

resistant, so that they were generally usable in a satisfactory manner for practical application »

A method of the invention comprises the loading of a Phthalosyania pigment in a bucket of inert _s © rga ~>

Liquid with a pure, strong, non-oxidizing acid. is not decisive and fcasK be applied is different Keagea aar HerBtellT2og of Elise, per molecule VhJa ₁ Io mjasiin 1 to 3 acid equivalent auffieiseia "The best & BSulta1? s are with 3cliwefelsäU2'e _s Ghlor aasserstoffsäure?, bromine? fasserstcsffßäui * e _s alipisatiscneii öcawefelBäureei3tei "2i5 an organic radical with nieiit iaeitr than 6 üoiil®aöiiof £ atoms beEitaea _r aro matisciien ßulfoa- acids of benzene and Hapirtjfelinreihe xmä ali ^ hatisdaen Sui fiasäuren." in which the organic radical has no more than 6 carbon atoms *. These two acids are therefore the preferred acids of this invention, ₉ which is even more evident when they are used Naturally evidently different from the Salsen, those produced by the ürasetaung of the Phyalosyaniae with kea, - Bentriertea ₅ aqueous acids or acids produced in the absence of organic diluents. The exact nature of the difference has not been established a chemical Unterschieä within the ge & aETbes PigmsntkOffipleses besttehen or ice jahysikaliseher differed on the surface "e © is not intended" the invention in any fheorie terms of this distinction £ it -csalegeii. Vfejm jed © eh apply the new Salse this invention hydrolyeiert ^ 'escape Pigments, which are very wiäerstaaasiä hig against -SseÄfee ^ Si ^^^ feafeÄ ^ Lsasfiass-sina and asahal new ^ areas of application for paintingaueasaaeiisetsisiigen with irhfelosyaain — Pigsieaiteja eroii ^ en This is achieved without the addition of any foreign matter in the pigment and through experience that can be carried out economically and smoothly. l £ aim «

tie satur the Fh ^ felozyaiiiri- ^ Pi ^ aentej which wex-den after the process of this isrfindung, I can vary widely «Sin ¥ orsug the invention ordered daria _? öaS the

v »w

üb High BJataloayaaia-Pigmerite as copper »Zinc · Jiickel-rUassi-iBetallfreies Phwloayanin serve as raw materials köimene addition below the BhWlQ ^ y nin & n itself and can their Uetallverbindungen üerivate be used as fetra" apn ^ tetraazoporphine · alkyl "- and Aryläerivato of .fh nine »halogenated © Pfroalosyanine» ietraaaaporphine. with dömea heterocyclic rings etc * iäe ϋ £ 3Α «& an advantage of the invention * that the pXiysilcalieoIie Fox ^ ia äea fhwlosyonine and its chemical purity vnwe & eatlioh i # * v As further

is described in more detail, the process of the present invention can be applied to raw pigments or even to the ite & ktiousmlschungp in dor the raw .pigiiient ^ produced Wj & r— the »apply * am a remarkable» economic advantage of the According to the invention, a purification and isolation of the PJb.yaloayanin ~ PigBenteß before the Gen. treatment is omitted and thus a significant reduction in costs occurs.

Bie used for Salsbildung® ». Acids

all lcein ^ n otark

oxy & atiron character. The © are the strong ", non-oxidizing läinerals & uren, such as bohwefeleäure" Ghloi ^a water ~ fötofXöture »Bromwsassei'aliOffeÄure» aroaiatisqthe sulfonic acids ^ like, Benaolsulfoäure, ^ oluoloulfosguren »Xylolöulfoeno & aleischen are brewing oleic acids · aliphatic oil sulfibar 'Especially if the ifohlenötofi'kefe-fce does not contain more than 6 £ OhlenstQ £ fatojne. Typical examples are methane sulfoic acid, aathane sulfoic acid, leUthionoic acid, usef. Aliphatisohe

o with higher molecular weight can also be used

be, but are less favorable liine next © class of strong organic ßEuren are the öqhwefelaäurehalbaater "like aB Methylsöhwefeleäurö, IthyleohwefelsSure us» w <- fciolbstverBtändlich also know J & iachungen dießer acids are used, and cases in some is the use voa fflisohtuigen "iirtaohaftliohför. The common acids are included in the "invention" and when acids are mentioned? wind & elbatverstiind «i · also lent solutions from the Söarsn included»

i "ie set forth above, ISFC" las Bhtaloayajiin.-iiiolelciil in the iage "öioh with 1 to B ftäureSquivalenton sra connect" can aeto Öaura vexisenden "However mittat" an excess äev

niclitu and only forms a superfluous waste * However, the process is completely dorch-

and it is therefore not intended that the present © Brfindtang bordered on any engin. The range of stoichiometric proportions of acid and phthalosyanine to be limited

In practice, any inert organic fluid can be wounded as a heat mediui. Bq can be the liquid 2 «B« a hydrocarbon, a mono- or polyhalogenated hydrocarbon, an ether »a star _for a per ton, etc.» Organic acids can also be used if they are sufficiently inert * Examples of organic liquids Bind / Benaol "eah? Qluol _r XyIoX ₉ iuono- _s di- and irlchlorbenaol, chloroform,! trichlorethylene» nonitrobenssol "aliphatic © nitro compounds such Mitroitteth Hitreäthan and Hitropropan, Bise'ssig etc.

iierai AUOH the organiB take S'lügei ness s widely ffiaße rilert may be "it's Natürli & h require _s that © i © some LöaeYör-fflögen besitaea v® & ad for VerWendetpn Siuron against the Phtaloayaiai""the Saei ^ e re ' Being sluggish in action «If the organic © f lüasigkeiTi a stronger one

Ψ
Akaeptor as that Phifalosyaiiin iet _t , the Sgmre will form a SaIa with de siglceit rather than with the pigment.

Here , an advantage of the invention is that the length of the liquid used as a reaction medium is not unduly important. Of course, there is a practical * lower öiwse how hot each Ömsetaung is carried out in an organic Pltisaigkeit "the, namely has enough liquid Torhanden seia _f so that the mixture can be stirred properly kaiua" JThe © forms di © practical Unters Crrenae that natuer borrowed something in Abiiängigktili Liquid changes · Yes, in general there are liquid quantities of 5 to 10 ropes per pigment part. Mixtures that are easy to stir. Larger quantities of liquid do not harm any further * but since they mean an economic waste "it is normally not desirable to go over a liquid quantity that results in a slightly au ruiirenaee Mecliuia"

Bs is desirable to leave you ot enough time. that & a can iaet with the acid, εο that the salt is completely possible in the desired. Ba that

PhtaXoayanin not a strong irotoaafcse ^ tor 1st, the te · »setaung does not take place mumeatan = Jm generally are guided by a few up to au, suitable for several studies · a silver ear axi

The reaction time is undesirable because this does not bring about any benefit and can adversely affect the piguant? by making it his maximum strength is reduced I wish you a good touch au. and in general there should be moderate movement during the reaction.

Öalsblldimg takes place within a wide range of temperatures. Jedooii give higher temperatures than room temperature and, with some liquids, pigments with lower values can be used. physical properties arise when the salsa are later hydrolysed "therefore Iat voranaielien, work at οβ, βτ, for example at Kiiamer - temperature" although the ßrfinaung dadiiroii is not strictly limited "

Obtaining the Q & Vab is a simple matter; common means such as filtering, i) ekantiorea, etc. are used. The particular method of isolation is not part of worlie ^ Naeen invention · Ds is not even necessary "the öala wl isolate prior to hydrolysis and therefore it let inöüliehs all © stages deö method of this invention in a einaigea Keäktionemedium durohsufUJiröa. *? Afa furthermore represents a detailed description of the invention »

The hydrolysis process step to be used if it is not possible to recover the hitalosyanine pigment, includes the implementation with a protonacceptor, which is a stronger irotonakaeptör than the Ph-falogyanin-Pigiaent lat * so that ar displaces the acid and oo daa oalss hydrolyzes. Typical proton receptors are water * alcohols, nitrogen bases * such as ammonia, pyridine, jiiraethylaniline, thisäolin, ifrlmethylaiain, morpholine and aniline. These are best .Oases in connection with lower aliphatic alcohols such as methanol or "Ethanol" are used "The Ibolierung des hydro- lysed pigment is effected by conventional means.

liesitzt _f ^ us £ pressed into the production of Ph ¹ ^ Iozyaninen that, faindj when the Kalae be hydrolyzed to aSamhiefthalluageii resis tandsiülii ^ diesel learn the ^ "invention further benefits" Z * B * may Sala © of lichteiHOfind "borrowed Phtalosyaninen as metal-free «Phyalogyanin © are produced * which are partially or completely destroyed by the previously known methods of 'sala formation«

Another advantage of this process is a befatoht in the

Ease mid ^ © quejailichlceit, with the ea in teohni, -. ift scale cannot be used «& * B. is an isolation of the crude pigment from the ^ eaktiosiowiiaoiiuixg, in de? eu her *. posed wirae, nielifc erxordorlich. The go ο i gaseous acid can be given directly and the corresponding QaXz isolated directly; be "or it can be hydrolyzed ά &. & tialss formed äaim _s and the resulting .Pigment be isolated. In dor iiorköiiim- borrowed method of Saligfaildung aas raw pigment Iiiteungsiaitteli had in. Which it warde made "duroli be freed filtration and subsequent AMünzten what & a dried had *" ^ as dried Produfct was then ait acid treated. Bie advantages of the new Procedures are evidently a single-stage procedure is apparently made accessible by some Itaboi-atoriuaißsfeafen;

The invention is accomplished in one by the following. Examples described * | & bwo-fetl-- © iii-jaiaiit-ii-sab ₍ & i-eBtigt 4 «-% - f — dea

All parts are weight parts.

30 'üeile, roUaü ifupfer-Pii ^ losyanin (obtained by the procedure ⁰ SSf «Ο'& ΐθη '^ Γϊΐβ'γβ?) And 38! Feil © xylaleulfc ^ acid (produced by adding. Of 22 lines xylene on 23' Filing 9% uffolic acid at? 0 ° - 80 ^l jpi-f were given to 300 parts of Mitrobensjol * the tüisokung vtrurd & 2 btimden stirred, while pigments ia the Salk of the pigment with mikrokristallinischer iitruktor mn "" the ^ eektiousmißchung then warde with Äbhylülkohol v © rdüiint _f filtered by the Saur © sais au hydro lyse and the taiiachung, - ^ ei * cake was dried with alcohol gewascilieii UUED ·

eii'tstandene pigment changed ä> icli _s wejiiii ea ia a fintenm'tüile with!, _s was ground itßögraphenlaok easily in one soft Färbpaste * the excellent structure "a brilliant hue and color strength groöe besaJ3" Sfenn Figment in a iiitroaelluloselack introduced-ix -bqlte ^ was se ige ea good Vjider-atainißbarenJieit Geg & xi ^^

Yes essentially the same wenw daö pigment were iaoliert after the ilydi * oli? Ee dtt3 * ch filtration

and the filter cake was then heated with steam * in order to remove organic particles »

Good results can also be obtained if, in the hydrolysis, instead of the iitfcanole, methyl or alcohol was used.

file tr ο dienes », sour (-aeiÄ- ^ g-ö4 @ i4 · lupffej.

ayanln were added to oiner LödUBg of Ö _S 98 3? eilen ö <Honohydrat in 200 feile »ü itrobenssol. * Me mixture was stirred at 25 ° to 30 °, ίΤ" hour ».

The green pulp that had arisen was filtered and the filter cake was washed in small portions with 250 liters of litrobea oil. ^ QT cake was then go- wash with alcohol! To hydrolyze ά && Sals si and ilaa resulting pigment washed with water »until the acid was free of acid. ! The pigment was at 60-65 ^o i> ^/ 'g © trockriet "

Pigment treated in this way had the same properties as the product from Example 1.

Examples

5 s 67 ropes of dry, acidic copper fh ^ losiyanin were added to a solution. The Misclnmg was 10 hours at 25 ° JLasg bia 3NC ^u> f'gerUhrt ·

The green pulp of the Entötandeaen Piginentfaalaeö was filtered and the cake with Kltrob ^ naol, alcohol with water Gewäsdien »The pigment was fo $ i 60 ° bia efj ^^ gotroelmet.

Pigtiient treated in this way had the same isigenucliafce as the product of Example 1.

Example 4 «

30! 'Hurry raw copper phloayasiin and 114 ropes xylene'.

ure (lisreesteilt duroh Kintrageji of 22 hone xylene in S3 rope © 9B? Üger Sohwef elaäwro hei, 70 ° to BQ ^and SSF parts »Hitrobenaol were added to the 300th Dia Mibellung was 2 iStunden gerührt- The üeaktiontämiechun ^ was dajiB treated with alcohol, around the eaure saig m hydrolyze and _f <i &"Pigmentt as in example 1 ^ eööiirieben _s icoliert-

3The bo received © at Pigiiieat was in its properties

comparable to dee example 1 «

The same results were obtained »? if Henzol-, f or HaphtalinaulföBäure anatafct of the xylölöulföic acid used

30 ropes of copper-ihtkloayanin and 38 l'eile xylenesulphonic acid (manufactured by. Jäin carry from 22! 'Reile xylene generally 23' x'elle Sulfuric acid at 70 ° to 80 ° ^) were given to 30% ohlorbensol, Me üiachung WUrUe 2 Btuaslsü that ϊ-lgiaent sales hydrolyzed and there resulted like ia example 1

The PigjaenteigeaischaXten ä & a eo li @ rgQSt © 12ten were the same as the yrodukteö of Example 1.

6th

30! Ropes copper P & ^ alaayaniii and 20 'üeile monohydrate would mn 300! Files litrobeii & iol gabea. Di® Hi was gerUlirt for 2 hours * the pigment & ala hydrolyzed the resulting £ lgß. @ N% as in. In & xaiel 1 isolated «

The same Ergefeüisee was erialt @ n ₉ when Sohwe £ elsöui * e old acid aur Sal ^ feildmiaen genomiaen "

Example 7.

35 ropes of raw zinc ph $ ilQ «yenln uad 76 files

acid (produced by adding 22 files xylene su 23 plates 98, -Siger Behwefelaäure toöi YO ⁰ · »80 ° X5 'were βα 300 ropes Ii-

given «Until we had guessed 2 hours? whereupon ethyl alcohol verditoni, rushed with 30!

au hydrolyze- 1> hs pigment like * 4e separated by filtration and grown with alcohol. ^ aoli the tUrocknon was sustaining a weieliea I ^J igmentpulTer IAIT same properties © "as the product of Example 1 *

Sleiqhe Jirresults © received »if

or _f wtallfreiö PhMilos ^ aiiine instead? d © & 2iiik use fc

10 folie raw «& upfe3vFhmla ££ tya & in were mn 300

föluol given dryer Ghlorftaa & ei'Btoff was introduced into the process * & is the big, coarse ia the samre ώαΐ », which be a fflikroltristalliBiöelie structure was converted. J3as sour bala became ait

hydrolyzed and the pigment iooled as in Beiapiöl 1

üie properties of ao treated Pigiaoirtö same de '

new of the product iron ßeiapiel 1 *

pale u ^ results w-fden, received * ¹ WeHtI -bengo! » trotaensol or Est.i'g & iütxre are used as lieakfcionsi & ediuia «

5s76 files "troato. © a _g sauapas iCupfex ^ i ^ lialüsj-aniii were added to a solution of 2» 2 parts of dry hydrogen chloride gas 300 files of nitrobenaol «bio mixture was ©"

iJöi · green porridge dee eatotan & enen Pignientsalaeö was filtered and the Xuohen washed with nitrobenaol _for alcohol and water

The pigment obtained in this way wixröö at 60 to 65 / € T getroeic · * net »

-Was & o treated l ^ igment resembled in fine Jäigonschaft

the product of example 1.

10.

5.76! 'Haste £ iipfe3> jph ^ aloByaain were on a "u of" 10 ropes. Ethyl sulphide units in 50 ropes Bitrobenaol ge give · j) The mixture was stirred at 25 * 30 ° -iT for 1 hour.

green Jirei dew entta / id ^ nen Salaee was filtered and the Ituchen with bitrooenaol »ilfcohol and water * dried at 60 ^a -6 $ °> K '

pigment treated in this way has the same leagues

shafts like that of example 1

Corresponding results were obtained with the use of diethionic acid instead of ethylsafleic acid.

5.76 'file Xupfer- "Ph ± fe.löS3raa.in warden Xn 100 file" loiionitro benzene

95 leiXe Äononitrofeenaol, the?, 88 parts lOOjiiee öohweenthielteja "were migextigt and di * i uischen 5 instead taught * Bi @ was then filtered and the RUcJcatand washed with J & onoaitVGlaenjSQl. Bi # Ansljee isolate © inen Qe-

Claims (1)

just 7 »9β üol Üohwefölsäure pr © mole pigment. Example 12 » * Two parts of raw copper plitaloayaine were given on two hundred ropes. A © LbOung vmi 21-5 was added to this pulp ! TelIsii achwefelooure-aaQnoh ^ drat joined in 50 ropes llilroiienacil au. stirs » adds. The treatment was done for 2 hours α ims # ~ l) 6i 10 ° bio 15 ° I) The green pulp was filtered with 200 ropes of ethanol which was saturated with amiaoniategaa ffare-n; and the cake Ijewasüh with Mstlianol free of eäarefrei. The isJuohen then joined and j) The iron clisffeen of the treated f'igmQ.ntß are similar to those of the product of Example 1 « Eäju 20 'l-'elle raw iCupfer-Phmloasyanin are au 200 I4itr-ob @ nsäol gegetoen. Iiiesem% -ei was #ine Lüianng of 27 '5' hone Schwefeliääure-Monohydlrat in i> 0 ΐeilen ütiobeniäol added. The Miaehimg was 2 btimdeiL-laag at 15 ° to 20 ° X "stirred" The green porridge was diluted with 1uu parts of ya ^ idin ₍ filtered and the oil was washed free of oil. The cake was then washed with washing / ash and dried. The own sharks of the bo-treated pigment o resembled denex deiä products β from example 1, bite, above examples emtsprecixonde Lrgobnisee were obtained "if Dimethylanjliix odoi * Miöohungea of pyridine and alliohol or Dimethylanil3n in methyl or ethyl alcohol are used in the dea acidic balaes * ijers bellt? on & alaen de contrary- öind »thereby g @ fceiiii2, eiühnet _s däiS aiii raw or aaf iierköiamliohe kind produced · Ph ^ loayaniiti-Pigwenu with a nonosyäi @ r © jiä € ns teaureaa, Subsijaua in an inert organic«, ii'lüsbigk @ it under possible ~ 4
- if desired - gätggqfeji $ 'ti ^ - ^ weeics & ewxxmu2ig one ent « p, against ϊ ^^^^^^ # «ϋ ^« ^ resistant PlimLos ^ anin-Pigmeiits « 2 ») Method according to claim. 1 _S fiadureh.
that the acidic substance is a strong acidic acid 3 ») Procedure according to i« »ixieprSoiiM 1 or 2? thereby germinating that the Eeaktionsiidsebims "move" 4 *) Procedure naeJa ^ Si address ^. 1 Ms 3 _? because I know that hydrolysis by means of a proton acceptor, which is a sharper ruton acceptor than there ^ ain-Pigiaer-t is, best, in the presence of a niedri mate®. _f aliplaatisclieji alcohol, is effected «