CH219929A - Process for the preparation of a condensation product. - Google Patents

Process for the preparation of a condensation product.

Info

Publication number
CH219929A
CH219929A CH219929DA CH219929A CH 219929 A CH219929 A CH 219929A CH 219929D A CH219929D A CH 219929DA CH 219929 A CH219929 A CH 219929A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
condensation product
ethylene urea
ethyleneimine
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
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
Publication of CH219929A publication Critical patent/CH219929A/en

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
    • C07D203/20—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 carbonic acid, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
    • 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
    • C07D203/02—Preparation by ring-closure

Landscapes

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

Description

  

  Verfahren zur Darstellung eines Kondensationsproduktes.         N-substituierte        Monoäthylenharnstoffe    von  der allgemeinen Formel:  
EMI0001.0003     
    können durch Umsetzung der entsprechenden       Isocyanate        mitÄthyleniminhergestellt    werden.

    Es wurde nun gefunden, dass     N-substituierte          Monoäthylenharnstoffe    oder ihre Derivate auch  durch Umsetzung der     N-Halogenverbindungen     von     Monocarbonsäureamiden    mit a,     @-Alkylen-          iminen,    insbesondere     Äthyleniminen    oder seinen  Homologen, bei Gegenwart von     Alkalien    her  gestellt werden können.  



  Gegenstand der vorliegenden Anmeldung  ist ein Verfahren zur Herstellung von     N'-          Heptadecyl-N        #        N-äthylenharnstoff     
EMI0001.0018     
    wobei man     Äthylenimin    in Gegenwart von  Alkali auf die     N-Halogenverbindung    von Stea-         rinsäureamid    einwirken lässt. Beispielsweise  setzt man     Äthylenimin    in Gegenwart von  Natronlauge mit     Stearinsäurechloramid    um.  



  Der     N'-Heptadecyl-N        #        N-äthylenharnstoff          fällt        in        einer        Ausbeute        von        90-95        %        an        und          schmilzt    bei 60-63 0. Das Produkt kann als  Textilhilfsmittel Verwendung finden.  



  <I>Beispiel:</I>  57     Gewichtsteile    feuchtes 55,7     o/oiges        Stea-          rinsäurechloramid    (F. P. 68 0) werden in 70  Gewichtsteilen feingemahlenem Eis zu einem  feinen Brei angerührt. Dazu gibt man 4,5  Gewichtsteile     Äthylenimin    und     rührt    die Paste  gut durch. Bei 10-15 o werden 12,6 Gewichts  teile 32,3     o/oiger    Natronlauge langsam hinzu  getropft, so dass die Temperatur 20 o nicht  übersteigt. Bei langsamem     Rühren    wird die  Paste     immer    fester. Das Rühren wird nach  Zugabe der Natronlauge fortgesetzt und be  endet, wenn die Temperatur bis 30 o gestiegen  ist.

   Die Temperatur steigt nach     Aufhören    des    
EMI0002.0001     
  
    Rührens <SEP> noch <SEP> bis <SEP> 40-45 <SEP>  . <SEP> Beginnt <SEP> die <SEP> Tempe  ratur <SEP> zu <SEP> fallen, <SEP> erhitzt <SEP> man <SEP> noch <SEP> 15 <SEP> -Minuten <SEP> in
<tb>  einem <SEP> Wasserbad <SEP> von <SEP> <B>50'.</B> <SEP> Die <SEP> Paste <SEP> begin t
<tb>  bei <SEP> langsamem <SEP> Rühren <SEP> wieder <SEP> zu <SEP> fliessen <SEP> und
<tb>  kann <SEP> zum <SEP> Gebrauch <SEP> mit <SEP> Wasser <SEP> auf <SEP> eine
<tb>  beliebige <SEP> Konzentration <SEP> eingestellt <SEP> werden.
<tb>  



  Zur <SEP> Reinigung <SEP> löst <SEP> man <SEP> eine <SEP> bestimmte
<tb>  Menge <SEP> in <SEP> reichlich <SEP> Äther, <SEP> trennt <SEP> die <SEP> wiIssi@ige
<tb>  Schicht <SEP> und <SEP> geringe <SEP> Mengen <SEP> äthei@unlüsliclier
<tb>  Substanz <SEP> ab. <SEP> Nach <SEP> dem <SEP> Abdampfen <SEP> des <SEP> Äthers
<tb>  und <SEP> dem <SEP> Nachwaschen <SEP> finit <SEP> Wasser <SEP> erliült
<tb>  man <SEP> durch <SEP> Trocknen <SEP> im <SEP> Vakuum <SEP> den <SEP> reinen
<tb>  Heptadecyläthylenliarnstoff <SEP> in <SEP> einer <SEP> Ausbeute
<tb>  von <SEP> 90-95"/o. <SEP> F. <SEP> P. <SEP> <B>60-631'.</B>



  Process for the preparation of a condensation product. N-substituted monoethylene ureas of the general formula:
EMI0001.0003
    can be prepared by reacting the corresponding isocyanates with ethyleneimine.

    It has now been found that N-substituted monoethylene ureas or their derivatives can also be made in the presence of alkalis by reacting the N-halogen compounds of monocarboxamides with a, @ -alkylene imines, in particular ethylene imines or its homologues.



  The present application relates to a process for the preparation of N'-heptadecyl-N # N-ethylene urea
EMI0001.0018
    whereby ethyleneimine is allowed to act on the N-halogen compound of stearic acid amide in the presence of alkali. For example, ethyleneimine is reacted with stearic acid chloramide in the presence of sodium hydroxide solution.



  The N'-heptadecyl-N # N-ethylene urea is obtained in a yield of 90-95% and melts at 60-630. The product can be used as a textile auxiliary.



  <I> Example: </I> 57 parts by weight of moist 55.7% stearic acid chloramide (F.P. 68 0) are mixed in 70 parts by weight of finely ground ice to form a fine paste. To this are added 4.5 parts by weight of ethyleneimine and the paste is stirred thoroughly. At 10-15 o, 12.6 parts by weight of 32.3 o / o sodium hydroxide solution are slowly added dropwise so that the temperature does not exceed 20 o. With slow stirring, the paste becomes more and more solid. Stirring is continued after the sodium hydroxide solution has been added and ends when the temperature has risen to 30 o.

   The temperature rises after the
EMI0002.0001
  
    Stirring <SEP> or <SEP> to <SEP> 40-45 <SEP>. <SEP> If <SEP> starts <SEP> the <SEP> temperature <SEP> falls to <SEP>, <SEP> heats <SEP> <SEP> for <SEP> 15 <SEP> minutes <SEP> in
<tb> a <SEP> water bath <SEP> by <SEP> <B> 50 '. </B> <SEP> The <SEP> paste <SEP> begin t
<tb> with <SEP> slow <SEP> stirring <SEP> again <SEP> to <SEP> flow <SEP> and
<tb> can <SEP> for <SEP> use <SEP> with <SEP> water <SEP> on <SEP> one
<tb> any <SEP> concentration <SEP> can be set <SEP>.
<tb>



  For <SEP> cleaning <SEP> <SEP> one <SEP> releases a specific <SEP>
<tb> Amount of <SEP> in <SEP> plenty of <SEP> ether, <SEP> separates <SEP> the <SEP> knowledgeable
<tb> Layer <SEP> and <SEP> small <SEP> amounts <SEP> äthei @ unlüsliclier
<tb> substance <SEP> off. <SEP> After <SEP> the <SEP> evaporation <SEP> of the <SEP> ether
<tb> and <SEP> the <SEP> rewashing <SEP> finite <SEP> water <SEP> fulfilled
<tb> man <SEP> by <SEP> drying <SEP> in <SEP> vacuum <SEP> the <SEP> pure
<tb> Heptadecyläthylenliarnstoff <SEP> in <SEP> a <SEP> yield
<tb> from <SEP> 90-95 "/ o. <SEP> F. <SEP> P. <SEP> <B> 60-631 '. </B>

Claims (1)

EMI0002.0002 PATENTANSPRUCH: <tb> Verfahren <SEP> zur <SEP> Herstellung <SEP> von <SEP> N'-Heptade e5-1-N <SEP> # <SEP> N-üthylenharnstoff, <SEP> dadurch <SEP> gekenn zeichnet, <SEP> dalman <SEP> Äthylemmin <SEP> in <SEP> Gegenwart <tb> von <SEP> Alkali <SEP> auf <SEP> die <SEP> N-Halogenverbindung <SEP> von <tb> Stearinsäureaniid <SEP> einwirken <SEP> lässt. <tb> Der <SEP> N'-Heptadecyl-N <SEP> . <SEP> N-ätliylenharnstoff <tb> fällt <SEP> in <SEP> einer <SEP> Ausbeute <SEP> von <SEP> 90-95 <SEP> ;'o <SEP> an <SEP> und <tb> schmilzt <SEP> bei <SEP> <B>60--63'.</B> <SEP> Das <SEP> Produkt <SEP> kann <SEP> als <tb> Textilhilfsmittel <SEP> Verwendung <SEP> finden. EMI0002.0002 PATENT CLAIM: <tb> Process <SEP> for <SEP> production <SEP> of <SEP> N'-heptade e5-1-N <SEP> # <SEP> N-ethylene urea, <SEP> marked with <SEP>, < SEP> dalman <SEP> Ethylemmin <SEP> in <SEP> present <tb> from <SEP> alkali <SEP> to <SEP> the <SEP> N-halogen compound <SEP> from <tb> allows stearic aniide <SEP> to act <SEP>. <tb> The <SEP> N'-Heptadecyl-N <SEP>. <SEP> N-ethylene urea <tb> <SEP> falls into <SEP> a <SEP> yield <SEP> of <SEP> 90-95 <SEP>; 'o <SEP> to <SEP> and <tb> <SEP> melts at <SEP> <B> 60--63 '. </B> <SEP> The <SEP> product <SEP> can <SEP> as <tb> Textile auxiliaries <SEP> find use <SEP>.
CH219929D 1940-07-24 1941-07-11 Process for the preparation of a condensation product. CH219929A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF3906D DE864867C (en) 1940-07-24 1940-07-24 Process for the preparation of N-substituted monoethylene ureas or their homologues

Publications (1)

Publication Number Publication Date
CH219929A true CH219929A (en) 1942-03-15

Family

ID=5832144

Family Applications (1)

Application Number Title Priority Date Filing Date
CH219929D CH219929A (en) 1940-07-24 1941-07-11 Process for the preparation of a condensation product.

Country Status (5)

Country Link
BE (1) BE443279A (en)
CH (1) CH219929A (en)
DE (1) DE864867C (en)
FR (1) FR874148A (en)
NL (1) NL57084C (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3250674A (en) * 1965-04-22 1966-05-10 Stauffer Chemical Co Method for controlling insects

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE681520C (en) * 1935-08-16 1939-09-25 I G Farbenindustrie Akt Ges Process for the production of nitrogen-containing products from alkyleneimines

Also Published As

Publication number Publication date
FR874148A (en) 1942-07-29
BE443279A (en) 1941-12-31
DE864867C (en) 1953-01-29
NL57084C (en) 1946-03-15

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