DEP0046592DA - Process for the production of quaternary ammonium compounds - Google Patents

Description

JiS is already proposed woröea

acidic, or d @ r «n derivatives on alipäatisohr> ÄÄäa #« inwirke » & « u! & ® © © Ji * di © Titraial by an alky! group substituted uind and of which one aiiidestesna one to the Toresteräug fflit the Hök® 3raolekular @ ii öäure g © la2i ^ ®M # H ^ droxjlgrupp® «athold The v © rbiiiäung © n in dlea® Weis © have & ®tt® & *» -like character, especially ale Ueta · » i> o && im» > ₉ Dii * · pergier- unaulgiermittel teelmiscn © Väemnung obtained «furthermore it is known that thea di @ valuable netstiiöeii property *.

aeer vorwännt © n body in Eritöhitea Hasse b @ i Terbia «

^ are the ± of the above gekennssei £ üm © te & instead eints Alkylsubstituentta aralkyl eiitii®lt®a "It was © ram gefundeng that Y © rbiBduiigen ₉ ai @ string a ·· a Aralk ^ lreet and a OxyaHtylreetf with a higher Fettsäurt n other , rB © it © over noch © inen ηα "ψ®τ ~ Oxyalkjlreet al © Substituentes on the quaternary stiok * ·

have substance, kooiibacteriEide body and _s dl «uiob. borrowed for the Yerwe & du & g ale disinfectants »

Until the invention is achieved, connections are made by the following general formula

⁸ I.

Σ - B

Yes this formula is:

Rn © iß low molecular weight oxyal3 £ ylre0t

acylated oxyalkyl radical with an equal to 6 and 18 el

of at least 6 and a maximum of 18 Eolxleiistoffatomeö. _t a

a low-molecular aliphatic "* * * gegsbeneaf ^ lls Soppelbiaidui ^ aii containing and / oäer interrupted by oxygen or nitrogen Sofaweftl alkyl bsw _e Cllklt

X is any

The production of the new? tertiary amines ,, in which

_ H ₂

is, with which ester makes Ra ~ ^ quaternary, Gd®a? indeia man. on the other hand, tertiary amines in which the

■ I '

iforg® forms lst _? Ult d @ m ester H «X in the ifberfü & Ft * D ^ rsrtige r © action» © fihig «Seter slM w @ is © the hydrogen halide and neutral ester ö @ r alcohol derived from the residues of gk osa E ^

no independent schute is claimed for the production of these tertiary amines »

As a starting point, such tertiary amines are yerwea * »which are aeylated by the content of a higher molecular weight

and an® unesterified Oi ^ alMylreste® are marked. It is displayed on a sweet basis by means of a step-by-step *! Structure of the higher molecular »residue * in that iaaa 2uB“ in amines * those next to the aliphatically bound Eest Β ”R ₄ , two more with suaaifiäiaöÄxahigen. Hydroxyl Ozyalkylreste wear _s a hydroxyl group through work towards a höhermoleicalaren Petteäur © with a "ta Acjlrest subsituiert. and you can si * B. in such a way that such an amine in the mixture is distilled from fatty acid to 80 - 250 ° and the condensation water. the

transesterification reaction can be calibrated speed, wtuaxi one in &&& Heaktionsgemiseh inert Gaee © inleitet or By / or provides by applying a vacuum and by rapid stirring a © accelerated Wegführang of Honöensstionswaesers "You can also the Eeaktionagemiseh solvent gus" tsen _f lie with their Hi the Kxjndensationsw & sser azeotrope afa & estilli & rt "As such solvents are" for example those organic compounds that form ^{asseotropic mixtures with water in the temperature range 1} TOn 80-250 °. In a preferred embodiment of the invention, carbon dioxide is introduced into the reaction mixture »Whereby the duration of the reaction is significantly shortened and, on the other hand, due to the displacement of the aerosols, the reaction product is darkened,

DI® ferbindtmgen obtained are h «lle oils represent You .besitzen the known properties of higher molecular weight tertiary amines, are thus in dilute acids, wi '8" B # formic Kösig- and lactic acid _t phosphoric ₉ Sals * "acid u * like * easy soluble. These solutions foam and have a bactericidal effect.

2 for the representation of the mines suitable as starting materials for the substance-wise formation of the above-mentioned higher aolecal nitrogen compounds _? the next to an aliphatic bond R ^ or H ^ ¹ swei O ^ ralkylreste on the nitrogen

contain, one can secondarily substitute ^ diaik / lolajais on the nitrogen by the best H ^ or R ^. On the other hand, mau rfureii gains the effect of organic al® reducing agents of common acids on oxyalkyl-HQXs & gN »lidia ~ compounds, in good yields tertiary bialkylolamines alfeylated on the nitrogen» For this purpose, equivalent amounts of oxyalkyl ^ xas5olide arid-forming , in ä # r Kalt® amfeiaanöea? act and lead the reaction through Irhitsjöii amf d @ m water bath % u, AIb acids particularly suitable for this purpose have been found to be oxaland formic acid *

But you can also aliphatic hydrogen halide, if necessary one or more Boppelbindujig © a © atfaalt @ nder oa ^ / or through oxygen, Sehwef ©! or allow nitrogen interrupted alkyl or sekoMär® Bialk ^ X © lamines to act in the presence of suitable a & aeptors and get the amines substituted on the nitrogen.

Another MQglieiikeit ®ur ßewinauag the besciiriebeneipwisclienprodtikte ordered that at © £ && primary amines ₉ are either a aliphatiseli Aralh ^ lreet eiaen or aliphatic, in the above formula my R. beaeiohnetea radical on the nitrogen contain ait gebaaden _t Ätnylenosjd can act and In both cases, this elee introduces two oxyalkylene residues into the primary amine group * One can also in stages υ © γ-geaen and in some cases only one molecule of ethylene oxide can act on a molecule of primary amine and it can be connected to it further with eth ^ implement leaoxyd »

Safhalt raan in the above-mentioned manner tertiary® amines, which are begsondera due to the content of a wxd © ines ae ^ lated osyalkyl residue 5 these are in a well-known way mi.% Of the reactive esters B ^ -Z or R ^ X converted into the ^ Ä ^ uaternären monimstTerbiaäimgen allowed to a Geaiseh of the two components in the cold "

or with increased f @ aperEtur under Ymrw & tidwag or

of solvents longer 2ei% on top of each other The compounds obtained would form * Let and soak in water and most organic solvents by being highly soluble

si © a ^ at® @ Netsvermüg «» »by which the penetration Gew ^ beettloke as well as the Ansbreitiwig on Y © r © cluaatsten infected surfaces aua © et * ora «ntlieli promoted wirfi«

Bie # rfiinä \ iögsge ^ .Bsen Ve ^ g Grand ilurerlösungenea b & kterissi & ^ ii proprietary geaeichaet for use as a disinfectant * Stm kÖauejQ. for sicii or locally with aaäerea means, if necessary under £ usats τοιι stretching agents as well as under 2ueat2 ττοχ htit enden- una gerachsverbeseernd «n means to disinfect objects of daily use in all textiles, laundry, various tiles»
and of apparatuses of sufficient and
Find use »

Elctios on ami field of ehirargiseiien hands-disinf make the preparations of these ferbindungefi ®in "r valuable Seut; . τλιι & is iVähr "nd bekanntlieä arrived at d ^ r sent to on par" · * · giscnen hands-Desinfektioii been Bäd ^ r% ax application by the vorseiiriftamäseig © adding an amount of 1 - containing 20 $ quaternary AsuaoniajaTerbindimgeia - $ 2 of 10 otaauapräparates z \ xv washing liquid subereitet were k nn the root preparation according to the present £ a * f £ adung without ^ ny VerdUnÄuagsiaaesnahrae aueh immediately become human © Heat applied mnd © in @ W & Sihung without damage to the skin enter »unnecessary SiOH the troublesome use any equivalence wiard the pesin faction adauaj? as a result of application-centered aee preparations © much verkürst _β Furthermore unfolds the konsentrierte solution of <juaternär @ s üinnoniiomYerbinduiis on the skin in the presence τοη little water a aueserqrdentliehe Eeiiiigußgswlrkunge the Vert of the disinfecting agent "b # d®iitend which increased"

The combined © Aaivenätoarkeit the aeaea

as "disinfection *" and Wa & ehmittel kean & eichn & t your superiority Tor other known products and igt as significant Fortechititt on the & ebiet © OCE Desinfektion® * to view _β

102 ₁ 4 Served «Benfcyl & iätha & oXa & in Tom Boiling Point Kq» 189 - 191 ⁰ S obtained by Kinektiven τ? Οη Χ MoI ₉ Bensyl chloride on 1 mole «Mäthanolaaln {I * 2f ° \ ± _n Q _{e (r} " wart of potassium carbonate and ans ^ Hliesaead Distillation in the Is3mmk ₉ values old 72 ^ 1 filXefi n ~ CaprjlsIare la eiacm glass flask Y €, right. Ansciiliesscad heats the mixture on gentle cooling at normal pressure initially to 160 ° and increases the temperature as it stands _f & m Enöe Ms to 200 ° »The condensate slowly aMestlllierertöe ioaswaeeer is caught in a graded Yorlage a Jf and ends the spray, so 9 g Kendensationawa ^ s ^ r passed © ina _s % vas after about 4 1/2 hours of the pail is"

In regulation aiauesiger design results d © s trial which provides after cooling performed © titrte @ tti © ^ # Eontrolle ά & τ Säureaahl a value <5e which it is evident _t that tTißeetsung is nearly run quantitatiT "Bor get © BensiyldiäthanolsQ & in mono-oapryleäureeeter ®ϊη reddish-colored oil is that in "rerdilnnter ants - ** acetic and""ilchsäure is readily soluble and effervescent © solutions gives _t acting bactericidal"

If 125 ropes of the ester obtained are mixed with 50 parts of dimethyl sulfate and Erwftnat © in an hour's bath on the water bath, 175 parts of a thick oil colored by © © brightrofbraori are obtained, which dissolves to give a clear solution in line® water and its solutions star & sehäuneiu Bas quaternary "salt iat in all organic solutions! smlttel & _t except in ether * soluble"
Example 2;

205 weights parts BenajldiäthaiiolsalJi (E _Q «189« 191 °) obtained by j Umsetsen of Benzjrlchlorid with a technically resulting mixture ύοά about 60 Bi # · 'and 40 ^ of triethanolamine and naehiOlgen e ^ & distillation in an oil pump "

vakouai be with 2OO _t 5 Lauriasäure gat stirred, and in an ordinary tion apparatus while passing in a hydrogen stream at 160 ° erfeitEt * If the Hauptae & ge of Koadensationswassere üTaerg & is addressed, increases to AEIE f © iap © temperature _β at 200 ® of about 8 nm Hg _5! laughing about 3 hours, the theoretical amount of 18 g of condensate is collected ionswasser. * thereon Man breaks the Ee & ction afc and läset aMtüiileiu J) ie Säureaahl the reac "" tionegsiaiscxiea of which is to elongate fert 139 _S 5 after completion üasetsmig 5 ₉ 6 dropped »

The Beasyldiätha! Iolamin "-aos.o" -laurin® acid ester is a light yellow colored oil, size easily dissolves in. Y «* r ~ dtißßter AIAE * sei3.-5 acetic _r flilöh- and fhospliorsäure su strong scftäumendesi! Solutions on welehe iiodibafcteriaid act *

35 parts by weight of the thus obtained £ © tertiary be 12 Nominal s approaches share dimethyl UNAE 20 hone ether Tenaisciit and about; Ilber 50 ⁰ SaeJat are Pas lii QuantitätiYer yield obtained quatornäre bala Ml "det _f a red-brown syrup && τ clearly dissolved in water *

In a corresponding Joise, one obtains from 16 parts by weight Sd fflöthylsulf at durcii about one hour © Erwä2? M © n. old 50 ropes of a Benzyldiathaaolaisiniiestergeiaiscijes, with the Een3ylaiätiianolamin ~ mono- »J ⁱ ettsäurfiefitcrn

(ißLUmi -ine the in the Ko & osölfett ^ gure vorfeoiamendeHTiCett ·

cF «it» a ^ sirapiform accruing ^ q_aateriiareÄ, ö

& V i'C chesaißohen and bacteriological "behavior naefa the Ki ^ necJaaften of the * above and under Example 3, mentioned compounds ia © I united * Example 3: ^ _-

119 ßewichtsteile / Oxy ^ tiiy ^ oxaeolldin from Lj "" 112 ° are gradually verieisclit with 55 parts of 85% AlheiseneSaar "* One waits through every further addition from _s to dsa. Carbon dioxide development caused violent foaming subsides, the reaction is heated for about 2 hours on a water bath and the dark-colored reaction product is then subjected to vacuum distillation © colorless © bi®

yellow colored oil tifc »rg« ht · bite yield feetr & gt 92 jt theojpeti @ elns » _s läregögöÄ on © itigesetatef ^^^ Ö

62.5 # © wick% @ shares HetläjMiätiisnolaäalö are jj & an Olaskolleii with 100 Feilem © laer K-okosöIfettsäure-Fraction von der 'Säsresahl 200 Törmiischt, whereby le "bad warming" is observed we o * Aaeahlitsseni erüitst aaa that

cooler

on 16 © ® _? the E® @ feti0ii to 200 ° * Da © aMestiXliei ^ iaäö KoM © naations «·

starts as »1» a giiaduierfcea Torl ^ ge auf «, ϊϊ & ο & 3. Stand © let di © tlaeor © tische Meng © load ensat ion®-

water (9 g) öb «rgegangea · Msdili ^ ss ^ rao is eaten

Ülal® »* Blue BestiMi ^ mg of Slmreaa

This © as Bad © d®r reaction saf etmm 21 Ab ^ eso & ken iet «Di® esterification outer EoitleaAio ^ a -blttleitea allows the same kind of EeÄtion in example 1 a ©

by 3 X / 2 Sfcondeßg iia Beißpi ©! 2 mm 2 X / Z den «

! © tteslEagen U ^ «0 | * eats © la oil, welefaes sicfe. in irerfilmi i- * Sal * - UBd J? ti ^ # priior © Smr @ leiöht gea dissolves # Derartig® LS © stomach act Bas EstergöBtieeii koxm uhn® further ^ 'cleaning

Subjected to a distillery

Is it tesi E " _Λ - * 155 - 105 Man irermisoht τοη the anxious 150 G« wlotite parts with 60% beazylolilorid and warms about 3 stiaMen Igag eof ISO ⁰ * -Dsaach leaves nan

wotoei a yellow-red thick sifup is obtained »öer sieii nacia eatspreeiie ^ er Beinigaa ^ im federn ferMltai © with Wiassf ^ adLecbt and durable» aqueous ferdößÄ «agea 1 t 5 uad 1 s delivers» Selche köso & gea e »iljieren batirfcerissid like s« B » p-Oiilor-aH ^ esol * Si © can 3ait

Using Teraiseht, «Sejcarte la # se» & tch are arbitrarily ait Säarea or with aaf ®iaea pE «Wert EwiseheB @ tw & 4« ad 8

- 9 -

150 'Ciewieiitsteile lletiiyldiatiianolsaixi {Κ _τ , 10 s = won nacii des? According to Example 3, mixed weight with IGG parts by weight of a hükoöolfettöiixLre fraction from aittleresi I.-oleku.li; weight 160 (iJäiireaahl 3 $ 0) .and 5G ropes of toluene. ^ iiBCiiliesseiid one leads 'flats Ge / üiscii in a l) estilliorai> paratar with ■ iassera'böcheifler and distilled the diircii Voresteni /' ifc ^ esilöete Eonaeiisüvioiiew & sser-seräigung der iiasciVi in the course of »eciie hours 'ie'idariß is the .uest des-Lüaungsmitüels in the Vacu.ujn ontfornt and aaeii Example 3. Suitable detergents kOiOnieri aueßer Soluul in ^ rajie: Benzol _t

nischei'A V "erbinauiig.eB operating in the temperature range of

80 - 250 ° with - barrels aaeotropic mixtures are formed and the active ingredients iuiin and i'ottic acid vuitar Beöin ^ tmgeri. oiißsiisöh not ma

Claims (1)

- 10! Patent claims * 1.) Procedure for the production of quaternary the allgeia @ ixi © n formula H
Σ - I ^ ² where H ^ acylated 2 ^ 0xjalkylrest vlt an acylsabstituenten with «It ** ¹ 6 to 18 carbon atoms * fi-j a / mralkylrest, R * ei & ö * ^. Low molecular weight aliphatic, if there is a double charge, is held @ ade2% and / or by oxygen _f sulfur or nitrogen anterfaroohenexv alkyl tew »Cjrcl © alkyl residue xma X a? ^ elieMgeitSäurexest ^ 4®4i ^« 4e * e ^ Ä® ^ tertiary® Amines of the general formula U <W £ U0 &}> t, _t äf & _y a & if $ H ^a i E ₂ or n £ ^. % φη0 £ && ηα, ^^ a reactive SsterV ^ j '", - the quatgr & ären ^ monitimYerbinduiigen $ \ ") Ferfahren, according to claim! Characterized _s dase mm to secondary Malkjlolamine aliphatiscJie aldehydes © InWe & s can, daraxif with an organic reducing action acid" treated, a Hydroxjl "grappe -rerestert by a higher molecular weight fatty acid, and the resulting product with reactive Esters y © & Aralky! Alcohols make quaternary in the usual white * <&. $ 3 «) Method according to spoke 1 e ^ ea *** ^ characterized j that one ale Amines ¥ _f erwendet in which a hydroxyl group by wi "r ^ ft one höheraolekularen is substituted and aaa. that makes substitution test » - 11 - ΓΙ j * ³ W) ferfaaren nach, AjaöprucBMI * dadareii marked _s the © man, O ^ alk ^ l-oxaSolidia-Terbinduiigea with Acids acting as reducing agents such as 'i treatedj / - - "t ■ introduces a fatty acid residue into the nitrogen aLfeyl species obtained as nitrogen aLfeyl species and makes it auaternary" / u) Method according to claim 2, characterized that halogen waeaeretoff esters aliphatic - or cyeloalkylalkoäol © in the presence of Sä> ir®akaeptore ^ like saux © or neutral carbonates , s * B _e sodium bicarbonate or tertiary amines ^ like iriätJianolamiii, 1-yridine, can act on secondary dialfcylolamines and those on nitrogen isine nacii Introduction of an acyl residue © EU of the quaternary bond umöetat * χ <£ / δ ") Yerfaiiren according Ansxjruchff ^{1 d>»} characterized gekeims € iicßn © t _s that iaaii to primary iijainej either a Arslkylrest or aliph &'tlselnari alkyl or Cycloalkylreet entiialteh on the nitrogen geTsaJÄen, Ithylen * oxide acting leaves _p acylated with higher fatty acids and an oxyalkyl imide containing a correspondingly aeylated oxyal radical containing tert ^; ; ren amines with reactive ^ sterile τοη itlteoholen in the qnaternary. .Aamoniuru enmity Γ L & he cf