CS200115B1 - Betaines of 11-aminoundecanoic acid and process for preparing thereof - Google Patents
Betaines of 11-aminoundecanoic acid and process for preparing thereof Download PDFInfo
- Publication number
- CS200115B1 CS200115B1 CS776578A CS776578A CS200115B1 CS 200115 B1 CS200115 B1 CS 200115B1 CS 776578 A CS776578 A CS 776578A CS 776578 A CS776578 A CS 776578A CS 200115 B1 CS200115 B1 CS 200115B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- betaines
- aminoundecanoic acid
- preparing
- carboxydecyl
- bromide
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- -1 10-carboxydecyl Chemical group 0.000 claims description 3
- IUDGNRWYNOEIKF-UHFFFAOYSA-N 11-bromo-undecanoic acid Chemical compound OC(=O)CCCCCCCCCCBr IUDGNRWYNOEIKF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UPUXKBBFYGSMDX-UHFFFAOYSA-N 10-carboxydecyl-decyl-dimethylazanium;bromide Chemical compound [Br-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCCC(O)=O UPUXKBBFYGSMDX-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-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
- FHJIRNQODJKHTH-UHFFFAOYSA-N butyl-(10-carboxydecyl)-dimethylazanium;bromide Chemical compound [Br-].CCCC[N+](C)(C)CCCCCCCCCCC(O)=O FHJIRNQODJKHTH-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 1
- 229950010007 dimantine Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález sa týká betaínov kyseliny 11-aminoundekánovej typu N-(lO-karboxydecyl)alkyldimetylaméniumbromidov obecného vzorca IThe present invention relates to 11-aminoundecanoic acid betaines of the N- (10-carboxydecyl) alkyldimethylamenium bromide of the formula I
R(CH3)2d®-(CH2)lo-COcP HBr , (I), kde R značí alkylový reťazec s počtom atémov uhlíka 4 až 18, a spósobu ich přípravy. Ako je známe, niektoré organické amóniové soli, ktorých molekula obsahuje najmenej jeden dlhý alkylový reťazec, vykazujú okrem iných vlastností aj letálne účinky na rózne kmene mikroorganizmov. U zlúčenín, ktoré sú predmetom vynálezu, sa zistili doteraz neznáme účinky na mikroorganizmy. Ich aktivita /optimálna dlžka reťazca R je C^2 až C^/ je v porovnaní s prostriedkami tohoto typu používanými v súčasnosti vyššia.R (CH 3 ) 2 d - (CH 2 ) 10 -COcP HBr, (I), wherein R represents an alkyl chain having 4 to 18 carbon atoms, and a process for their preparation. As is known, some organic ammonium salts whose molecule contains at least one long alkyl chain exhibit, among other properties, also lethal effects on various strains of microorganisms. The compounds of the invention have previously been found to have unknown effects on microorganisms. Their activity (the optimal chain length of R is C ^ 2 to C ^) is higher than the currently used formulations of this type.
Zlúčeniny, ktoré sú predmetom vynálezu, sa prlpravujú reakciou příslušného alkyldimetylaminu s kyselinou 11-brémundekánovou v prostredíetanolu pri teplote kúpela 100 až 110 °C počas 24 hodin.The compounds of the invention are prepared by reacting the corresponding alkyldimethylamine with 11-bromundecanoic acid in an ethanolic environment at a bath temperature of 100-110 ° C for 24 hours.
Příklady ilustrujú vyššie uvedené zlúčeniny a spósob ich přípravy.The examples illustrate the above compounds and a process for their preparation.
200 115200 115
200 US200 US
Příklad 1Example 1
Ekvimolárna zmes kyseliny 11-brómundekánovej a butyldimetylamínu sa nechá reagovať v 30 ml etanolu pri teplote kúpela 100 až 110 °c počas 24 hodin. Po oddestilování rozpúSťadla a prekryStalizovaní sa ziska N-(10-karboxydecyl)butyldimetylamóniumbromid vo výtažku 42 %; t.t. 81 až 82 °C; Rp=0,78; IČ-spektrálne charakteristiky: 5 (CO) 1725, -9(CH) 2935, 2860, úfCHg) 1470 cm-1 /v KBr tablete/.The equimolar mixture of 11-bromodecanoic acid and butyldimethylamine is reacted in 30 ml of ethanol at a bath temperature of 100-110 ° C for 24 hours. After distilling off the solvent and recrystallizing, N- (10-carboxydecyl) butyldimethylammonium bromide was obtained in a yield of 42%; mp 81-82 ° C; R p = 0.78; IR spectral characteristics: δ (CO) 1725, 99 (CH) 2935, 2860, (CHCl 3) 1470 cm -1 (in KBr tablet).
Příklad 2Example 2
Pracovný postup je ten istý ako v přiklade 1, do reakcie sa vfiak použil decyldimetylamín. Vzniká N-(10-karboxydecyl)decyldimetylamóniumbromid vo výtažku 45 %; t.t. 89 až 90 °C; Rp=0,59; IČ-spektrálne charakteristiky: \?(C0) 1725, (CH) 2935, 2860, 5(CH2) 1475 cm1 /v KBr tablete/.The procedure was the same as in Example 1 except that decyldimethylamine was used in the reaction. N- (10-carboxydecyl) decyldimethylammonium bromide is obtained in a yield of 45%; mp 89-90 ° C; Rf = 0.59; IR spectral characteristics:? (CO) 1725, (CH) 2935, 2860,? (CH 2 ) 1475 cm -1 (in KBr tablet).
Příklad 3Example 3
Pracovný postup je ten istý ako v příklade 1, do reakcie sa použil dimetyloktadecylamin. Vzniká N-(10-karboxydecyl)dimetyloktadecylamóniumbromid vo výtažku 50 %; t.t. 102 až 103 °C; RF=0,19; IČ-spektrálne charakteristiky: Ό(CO) 1725, \>(CH) 2920, 2860, 5(CHg)The procedure is the same as in Example 1, with dimethyloctadecylamine being used in the reaction. N- (10-carboxydecyl) dimethyloctadecylammonium bromide is obtained in a yield of 50%; mp 102-103 ° C; RF = 0.19; IR spectral characteristics: [delta] (CO) 1725, > (CH) 2920, 2860, 5 (CHg)
1475 cm”1 /v KBr tablete/.1475 cm ” 1 / in KBr tablet /.
Všetky zlúčeniny, ktoré sú predmetom vynálezu, sú biele, nehygroskopická krystalické látky, rozpustné v etanole, metanole, chloroforme, málo rozpustné vo vodě, aceténe, nerozpustné v benzéne, étere a petrolétere.All compounds of the invention are white, non-hygroscopic crystalline substances, soluble in ethanol, methanol, chloroform, poorly soluble in water, acetene, insoluble in benzene, ether and petroleum ether.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS776578A CS200115B1 (en) | 1978-11-27 | 1978-11-27 | Betaines of 11-aminoundecanoic acid and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS776578A CS200115B1 (en) | 1978-11-27 | 1978-11-27 | Betaines of 11-aminoundecanoic acid and process for preparing thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200115B1 true CS200115B1 (en) | 1980-08-29 |
Family
ID=5427338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS776578A CS200115B1 (en) | 1978-11-27 | 1978-11-27 | Betaines of 11-aminoundecanoic acid and process for preparing thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS200115B1 (en) |
-
1978
- 1978-11-27 CS CS776578A patent/CS200115B1/en unknown
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