CS200113B3 - Process for preparing betaines of 11-aminoundecanoic acid - Google Patents
Process for preparing betaines of 11-aminoundecanoic acid Download PDFInfo
- Publication number
- CS200113B3 CS200113B3 CS776378A CS776378A CS200113B3 CS 200113 B3 CS200113 B3 CS 200113B3 CS 776378 A CS776378 A CS 776378A CS 776378 A CS776378 A CS 776378A CS 200113 B3 CS200113 B3 CS 200113B3
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- aminoundecanoic acid
- betaines
- acid
- reaction
- preparing
- Prior art date
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- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- IUDGNRWYNOEIKF-UHFFFAOYSA-N 11-bromo-undecanoic acid Chemical compound OC(=O)CCCCCCCCCCBr IUDGNRWYNOEIKF-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- -1 10-carboxydecyl Chemical group 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 206010008674 Cholinergic syndrome Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003551 muscarinic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález sa týká spdsobu přípravy betaínov kyseliny 11-aminoundekánovej obecného vzorce IThe invention relates to a process for the preparation of 11-aminoundecanoic acid betaines of the general formula I
R(CH3)2ř(®-(CH2)10-C0cP HBr (I), kde R značí alkylový reťazec s počtom atómov uhlika 4 až 18. Organické amóniová soli, ktoré vo svojej molekule obsahujú najmenej jeden dlhý alkylový reťazec, najčastejáie Ci4· vykazujú rad zaujímavých vlastnosti. Majú povrchovoaktívne, dezinfekčně vlastnosti, muskarínový a nikotinový účinok a podobné. Tieto ich vlastnosti sa využívájú v áirokej paleto pr ionty se Iných výrobkov. Prípratva týchto zlúčenin vychádza najčastejšie z halogénalkánu a. příslušného terciárneho aminu. Vyššie uvedené zlúčeniny sa dajú připravit pčsobenim kyseliny 11-brómundekánovej na terciárny amin s r6žnou dlžkou alkylového reťazca v prostředí etanolu. Vznikájú však produkty v nizkom>výtažku /40 až 50 %/, znečistěné rozkladnými produktem! reakcie, ktoré sa dajú oddělit len velmi ťažko od finálneho výrobku. Reakčný čas je 24 hodin, teploty kúpela 100 až 110 °C.R (CH 3 ) 2 β ((- (CH 2 ) 10 -COC p HBr (I), wherein R represents an alkyl chain having a carbon number of 4 to 18. Organic ammonium salts containing at least one long alkyl chain in their molecule, most often C i4 · you Kazuya number of interesting properties. they surfactants, disinfectant properties, muscarinic and nicotinic effects and the like. these their properties are used in a wide Paleto pr ions other products. Prípratva these compounds is based on the most common of haloalkanal a. respective tertiary amine. The above compounds can be prepared by treating 11-bromo-decanoic acid with a tertiary amine of varying alkyl chain length in ethanol, but produce low yields (40-50%) contaminated with decomposition products which are difficult to separate. The reaction time is 24 hours, bath temperature 100-110 ° C.
UVedené nevýhody odstraňuje spAsoh podía vynálezu, kde sa pósobi kyselinou 11-brémundekánovou na alkyldimetylamín v prostředí metylkyanidu pri teplota varu rozpúátadla počas hodin. Po podstatné skrátenej reakčnej době vznikajú produkty vo výtažku 90 až 95 % vysokej čistoty.The above drawbacks eliminate the process of the invention wherein 11-bromundecanoic acid is treated with alkyldimethylamine in methyl cyanide at the boiling point of the solvent for hours. After a substantially reduced reaction time, the products are obtained in a yield of 90 to 95% high purity.
200 113200 113
200 113200 113
Na ilustráciu tejto novej metédy přípravy sú uvedené následovně příklady.The following examples are given to illustrate this new method of preparation.
Příklad 1Example 1
Zmes 26,5 g kyseliny 11-brémundekánovej, 11,1 g butyldlmetylamínu a 25 ml metylkyanidu sa zahrieva pod sp&tným tokom 4 hodiny. Po ochladení sa produkt odfiltruje a přečistí kryštalizáciou z aceténu. Výťažok N-(10-karboxydecyl)butyldimetylaméniumbromidu Je 90 X: t.t. 81 až 82 °C; Rp=0,78 /sústava acetén:lN HC1 (1:l), detekcia Dragendorfovým Činidlom/: IČ-apektrálne charakteristiky: V(CO) 1725, (CH) 2935, 2860, fftCHg) 1469 cm1.A mixture of 26.5 g of 11-bromundecanoic acid, 11.1 g of butyldimethylamine and 25 ml of methyl cyanide is heated under reflux for 4 hours. After cooling, the product was filtered off and purified by crystallization from acetene. The yield of N- (10-carboxydecyl) butyldimethylamenium bromide is 90 °: mp 81-82 ° C; Rf = 0.78 / acetén system: 1N HCl (1: l), Dragendorfovým detection reagent /: IR-apektrálne characteristics: W (CO) 1725 (CH) 2935, 2860, fftCHg) 1469 cm 1st
Příklad 2Example 2
Pracovný postup je podobný ako v příklade 1, namiesto butyldimetylaninu sa do reakeie použil dimetyloktadeeylamin. Výťažok N-(10-karboxydecyl)dimqtyloktadecylaméniumbromidu je 95 X; t.t. 102 až 103 ®C; RF«0.19; IČ-spektrálne charakteristiky: S? (CO) 1725, 9(CH) 2920, 2860, S(CH2) 1475 cm'1.The procedure is similar to Example 1, but instead of butyldimethylanine, dimethyloctadeeylamine was used in the reaction. The yield of N- (10-carboxydecyl) dimethyloctadecylamenium bromide is 95%; mp 102-103 ° C; R F 0.1 0.19; IR spectral characteristics: S? (CO) 1725.9 (CH) 2920, 2860, S (CH 2 ) 1475 cm -1 .
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS776378A CS200113B3 (en) | 1978-11-27 | 1978-11-27 | Process for preparing betaines of 11-aminoundecanoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS776378A CS200113B3 (en) | 1978-11-27 | 1978-11-27 | Process for preparing betaines of 11-aminoundecanoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200113B3 true CS200113B3 (en) | 1980-08-29 |
Family
ID=5427315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS776378A CS200113B3 (en) | 1978-11-27 | 1978-11-27 | Process for preparing betaines of 11-aminoundecanoic acid |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS200113B3 (en) |
-
1978
- 1978-11-27 CS CS776378A patent/CS200113B3/en unknown
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