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DE736194C - Process for the preparation of acylated alkyleneimines - Google Patents

Process for the preparation of acylated alkyleneimines

Info

Publication number
DE736194C
DE736194C DEI69589D DEI0069589D DE736194C DE 736194 C DE736194 C DE 736194C DE I69589 D DEI69589 D DE I69589D DE I0069589 D DEI0069589 D DE I0069589D DE 736194 C DE736194 C DE 736194C
Authority
DE
Germany
Prior art keywords
alkyleneimines
acylated
preparation
oos
imine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DEI69589D
Other languages
German (de)
Inventor
Dr Ernst Dietl
Dr Ernst Ploetz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI69589D priority Critical patent/DE736194C/en
Application granted granted Critical
Publication of DE736194C publication Critical patent/DE736194C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
    • C07D203/18—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carboxylic acids, or by sulfur or nitrogen analogues thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von acylierten Alkyleniminen C=c-cnstalul des Patents ; ;; ooS ist ein Verfahren zur Herstellung von \ # \-(u .f; @ A1- ky-lcn)-acctamidcii durch 1-msetzcn von Keten mit CC # f Alky-lenlmlnen. Iss wurde nun -efunden, daii man andere aclit:rte r:. ri-Alky-lcliimilic erhält. wenn man . in Stelle von Keten selbst solche hctcne. die mindestens S KOhlenst011atonlc 1I11 Molekül enthalten. mit 4 # /i-Alkyleliimincli umsetzt. Ge- ig Iletc hctctie sind beispielsweise Hexy-1-, De- <-y-i- und 1-ie@ad@#cylkcten sowie Gemische sol- ':i;er lZetene, z. h. solche, die Gemischen I::.turlichcr o(lor synthetischer höhermole- .;;Il.lrcr i%;t@:iurcn ctitsprcchcn. Die hetene i;l bUL'Lliliter Weise durch '111I: tcln @IOIlOC1rl)C>I1Sai11-C11.IlO@CI11dC11, cii,- mindcstcns S I#-olilenstoliatonic im @-Ittil;:i;; ;I, Init starken tertiären Basen her- 1 )ir I-ti:@ctzung der Kctctic mit den Al- ky-lcliiniineti c-rfolgt in Abwesenheit von «-asser, Z@@'e@klliaJ@lg in Gegenwart indifferen- ter 1_ösuli-smittel. Vorteilhaft setzt man das Beten unmittelbar anschließend an seine Her- stellung um. indem man das Alky-lenimin zu der Reaktionslösung, die das Keten und z. B. das Chlorhydrat des verwendeten terti;iren Amins enthält, zulaufen läßt. Das Aminchlor- liydrat wird dann erst nach erfolgter I: m- setzung abgetrennt. Dies bringt u. a. den Vorteil mit sich, daß der Ausschluß der Luft- feuchtigkeit ohne besondere apparative Maß- nahmen gewährleistet ist. Die nach dem Verfahren erhältlichen hoch- moIckularcii acvlicrten AIkvlcnimine sind hall)- feste, wachsartige \Iassen,I die, bcispiclswc.ise in emulgicrter oder dispergicrter Form, als Tc@.tilhilfsmittel, z. B. als waschbeständige UVcichmachungs-und Hydrophobicrtnigsmittcl, dienen können. 13eispiele- i. Iil eine Lösung von 253.g I-Iesadecy-l- ketcll in ; oo ccin Benzol lä13t tnan unter Itüll- rell und unter Einhaltung einer TCnlperatür ': cln Z 5 bis üo langsam 6o ä .1thy-lcnimin tliclkli. Bei der gleichen Temperatur rührt 11);'1l <<eitere 2 Stunden. Dann entfernt man das Lösungsmittel im ni:il.3igen Vakuum bei etwa 5o und i#rliült so N # N-fa # ß-<ltlivlen #- ;learo@-l@imid in einer Ausbeute von etwa 9o1).) ::1s gelbliche. wachsariige 'Masse mit einem 5,'I1mC1"l1)lllllkt t'011 etwa 5 _. I'1 (!in Gemisch voll 253- I-IC\adec)-1- h("ell mit etwa i3- ,g Trllltll%'lamiiichlorllvdrat ,l11(1 -ooo ('c111 Benzol, das durch I. lnsetzün- l'011 Stüarinsaurechlorld mit TrlatllN"Ianl::n in Benzol ,ntstanden ist, läf nian unter den deichen Bedingun-en. «-ic in Beispiel t an- gegeben. langsam 6o- Äthylenimin tlicheli. \ach beendigter L'msetzun- hltricrt man das "I'ri<<thvlaminchlorhvdrat ab, wäscht den -Nie- mit I'c#nzol wid entfernt aus dem Filtrat (las Lösungsmittel durch .11)destiIlicrcn wie im r-cispicl i. I):c Ausbeute an \ # \- (r< . j;-=lthylcn @-stcaro`-lamid bcträt c@r@'@ n. @'er« endet man an Stelle des @c:cadcc@-1- ketens Decclketen, so erll.,ilt man das \ # \- rc der l.aurinsiurc, das ähn- liche 1?i;;ciischatten besitzt. Bei Verwendung von c1, # %J-I'ropylenimin an Stelle von Äthylen- imin erhält man das entsprechende \ # \- r@.;l-r'rop@len< mid der Stcarnisäul-e. Process for the preparation of acylated alkyleneimines C = c-cnstalul of the patent; ;; ooS is a Process for the production of \ # \ - (u .f; @ A1- ky-lcn) -acctamidcii by 1-msetting of ketene with CC # f alkylene linings. Eat has now been found to be different aclit: rte r :. ri-alky-lcliimilic is obtained. if . in In place of ketene themselves, there are such bars. the at least S KOhlenst011atonlc 1I11 molecule contain. with 4 # / i-Alkyleliimincli implemented. Ge ig Iletc hctie are, for example, Hexy-1-, De- <-yi- and 1-ie @ ad @ # cylkcten and mixtures should ': i; he lZetene, zh such, the mixtures I ::. Turlichcr o (l or synthetic higher mol- . ;; Il.lrcr i%; t @: iurcn ctitsprcchcn. The hetene i; l bUL'Lliliter way through '111I: tcln @ IOIlOC1rl) C> I1Sai11-C11.IlO@CI11dC11, cii, - mindcstcns SI # -olilenstoliatonic im @ -Ittil;: i ;; ; I, Init strong tertiary bases produced 1 ) ir I-ti: @ctzung der Kctctic with the Al- ky-lcliiniineti c-r takes place in the absence of «-Asser, Z @@ 'e @ klliaJ @ lg in the present indifferent- ter 1_ösuli-smittel. It is advantageous to use this Immediately afterwards pray to his adjustment. by adding the alkylenimine the reaction solution containing the ketene and z. B. the chlorohydrate of the tertiary used Contains amine. The amine chlorine liydrate is then only after I: m- settlement separated. This brings among other things the This has the advantage that the exclusion of air humidity without special equipment is guaranteed. The high- moIckularcii acvlicrten AIkvlcnimine are hall) - solid, waxy \ Iassen, I die, bcispiclswc.ise in emulsified or dispersed form, as Tc @. Auxiliary tools, e.g. B. as washable UV protection and hydrophobic treatment, can serve. 13examples- i. Iil a solution of 253.g of I-Iesadecy-l- ketcll in; oo ccin benzene can be used under rell and in compliance with a TCnlperatur ': cln Z 5 to uo slow 6o ä .1thy-lcnimin tliclkli. Stir at the same temperature 11); '1l << more than 2 hours. Then you remove the solvent in a low vacuum about 5o and i # rliält so N # N-fa # ß- <ltlivlen # - ; learo @ -l @ imid in a yield of about 9o1).) :: 1s yellowish. waxy 'mass with a 5, 'I1mC1 "l1) lllllkt t'011 about 5 _. I'1 (! In a mixture full 253- I-IC \ adec) -1- h ("ell with about i3, g Trllltll% 'lamiiichlorllvdrat , l11 (1 -ooo ('c111 Benzene, which was released by I. l'011 Stüarinsaurechlorld with TrlatllN "Ianl :: n in Benzene, which has arisen , runs under the dike conditions. «-Ic in example t an- given. slowly 6o- ethylene imine tlicheli. After you have finished implementing it, you do not understand that "I'ri << thvlaminchlorhvdrat, washes the -Nie- with I'c # nzol wid removed from the Distil the filtrate (passed the solvent through 11) as in r-cispicl i. I): c yield of \ # \ - (r <. j; - = lthylcn @ -stcaro`-lamid bcträt c @ r @ '@ n. @ 'er «ends in place of @c: cadcc @ -1- ketens Decclketen, so erll., if the \ # \ - rc the l.aurinsiurc, which is similar liche 1? i ;; ciish shade possesses. Using of c1, #% I-I'ropylenimine instead of ethylene imin you get the corresponding \ # \ - r @ .; l-r'rop @ len <mid der Stcarnisäul-e.

Claims (1)

hA'l'li\1'_1\S1'l:UC11: Verfahren zur I--Ier.z;telltlll" voll act"liel-- ten Allcyleniminen, dadurch @el:ennze@ch- net. clali man in Wciterhildun.- des Ver- fahrens nach Patent ;-35 ooS hier solche Isetene, die mindestens S Iiohlcnstoftatome im Molekül enthalten, auf u.;3-:11klcn- imine in Ahwüsenhcit von Wasser ":n- wirken I@i15t.
hA'l'li \ 1'_1 \ S1'l: UC11: Procedure for I - Ier.z; telltlll "voll act" liel-- ten alkylenimines, thereby @el: ennze @ ch- net. clali man in Wciterhildun.- des Ver driving according to patent; -35 ooS here such Isetenes which contain at least silicon atoms contained in the molecule, on u.; 3-: 11klcn- imine in Ahwüsenhcit von Wasser ": n- work I @ i15t.
DEI69589D 1941-05-15 1941-05-15 Process for the preparation of acylated alkyleneimines Expired DE736194C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI69589D DE736194C (en) 1941-05-15 1941-05-15 Process for the preparation of acylated alkyleneimines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI69589D DE736194C (en) 1941-05-15 1941-05-15 Process for the preparation of acylated alkyleneimines

Publications (1)

Publication Number Publication Date
DE736194C true DE736194C (en) 1943-06-09

Family

ID=7197019

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI69589D Expired DE736194C (en) 1941-05-15 1941-05-15 Process for the preparation of acylated alkyleneimines

Country Status (1)

Country Link
DE (1) DE736194C (en)

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