CS200112B3 - Process for preparing ammonium salts of esteres of 11-aminoundecanoic acid - Google Patents
Process for preparing ammonium salts of esteres of 11-aminoundecanoic acid Download PDFInfo
- Publication number
- CS200112B3 CS200112B3 CS776278A CS776278A CS200112B3 CS 200112 B3 CS200112 B3 CS 200112B3 CS 776278 A CS776278 A CS 776278A CS 776278 A CS776278 A CS 776278A CS 200112 B3 CS200112 B3 CS 200112B3
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- ammonium salts
- esteres
- aminoundecanoic acid
- preparing ammonium
- methyl
- Prior art date
Links
- 150000003863 ammonium salts Chemical class 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 title 1
- 125000004185 ester group Chemical class 0.000 title 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- IUDGNRWYNOEIKF-UHFFFAOYSA-N 11-bromo-undecanoic acid Chemical compound OC(=O)CCCCCCCCCCBr IUDGNRWYNOEIKF-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- -1 hexyl ester Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- HSRFXYHFPDYLPW-UHFFFAOYSA-M CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCC(OC)=O.[Br-] Chemical compound CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCC(OC)=O.[Br-] HSRFXYHFPDYLPW-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(54) Spósob přípravy amóniových solí ésterov kyseliny 11-amínoundekánovej(54) A process for the preparation of ammonium salts of 11-aminoundecanoic esters
Vynález sa týká spósobu přípravy amóniových solí esterov kyseliny 11-amlnoundekánovej typu N-dodecyl-(10-alkoxykarbonyldecyl)dimetylamóniumbromidóv obecného vzorca I C12H25(CH3)2I^-(CH2)1O-CO()R Bi® (I).The invention relates to a process for preparing ammonium salts of esters of 11-amlnoundekánovej of the N-dodecyl (10 alkoxykarbonyldecyl) dimethyl ammonium of the formula I, C 12 H 25 (CH 3) 2 I ^ - (C H 2) 1 O - CO () R Bi ® (I).
kde R značí: metyl, etyl, propyl, izopropyl, butyl, pentyl, izopentyl, hexyl a benzyl. 0r: ganické amóniové soli, ktoré obsahujú vo svojej molekule najihenej jeden dlhý alkylový reťazec, vykazujú například povrchovoaktlvne, dezinfekčně vlastnosti, pósobia na biologické systémy a podobné. Tieto ich vlastnosti sa využívajú v mnohých prieoyselných odvetviach. Příprava týchto katiónových látok vychádza najčastejšie z halogénalkánu a terciárneho aminu. Vyššie uvedené zlúčeniny sa dajú pripraviť pósobením'esterov kyseliny 11-brómundekánovej na terciárny amin s róznou dlžkou alkylového reťazca v prostředí etanolu, připadne vo vodě. Reakčné časy sa pohybujú okolo 24 hodin, reakčné teploty sú závislé na teplote varu ; rozpúSťadla, teplota kúpela bývá 100 až 110 °C. Produkty však vznikajú v nízkom výťažku, znečistěné a izolácia je velmi obtiažna, pretože tieto zlúčeniny sú hygroskopické a výborné rozpustné v polárných rozpúšťadlách, ako je etanol.wherein R represents: methyl, ethyl, propyl, isopropyl, butyl, pentyl, isopentyl, hexyl and benzyl. Organic ammonium salts containing one long alkyl chain in their molecule exhibit, for example, surface-active, disinfectant, biological system effects and the like. These properties are used in many industries. The preparation of these cationic substances is most often based on a haloalkane and a tertiary amine. The above compounds can be prepared by reacting 11-bromo-decanoic acid esters to form a tertiary amine with a different alkyl chain length in ethanol or water. Reaction times are about 24 hours, reaction temperatures are dependent on boiling point; the temperature of the bath is 100-110 ° C. However, the products are produced in low yield, contaminated and isolation is very difficult because these compounds are hygroscopic and excellent soluble in polar solvents such as ethanol.
UVedené nevýhody odstraňuje spósob podía vynálezu, kde sa pósobi esterom kyselinyThe above drawbacks overcome the process of the invention wherein the acid ester is treated
11-brómundekánovej na doecyldimetylamín v prostředí metylkyanidu pri teplote varu rozpúšťadla počas 4 hodin. Vznikajú produkty vo výťažku 80 až 83 % teórie vysokej čistoty.11-bromodecanoic acid to doecyldimethylamine in methyl cyanide at the boiling point of the solvent for 4 hours. The products are obtained in a yield of 80-83% of high purity theory.
200 112200 112
200 112200 112
Na ilustráciu tejto novej metády přípravy sú uvedené následovně příklady.The following examples are given to illustrate this new preparation method.
Příklad 1Example 1
Zmes 8,5 g dodecyldimetylamínu a 11,2 g metylesteru kyseliny 11-brámundekánovej sa nechá reagovat v 20 ml suchého metylkyanidu pri teplote varu rozpúšťadla počas 4 hodin. Po tomto čase sa rozpúSťadlo oddestiluje a surový produkt sa prekrystalizuje zo suchého sestánu. Vzniká N-dodecyl-(10-metoxykarbonyldecyl)dimetylamóniumbromid vo výtažku 80 X; t.t.A mixture of 8.5 g of dodecyldimethylamine and 11.2 g of 11-bromo-decanoic acid methyl ester is reacted in 20 ml of dry methyl cyanide at the boiling point of the solvent for 4 hours. After this time, the solvent was distilled off and the crude product was recrystallized from a dry assembly. N-dodecyl- (10-methoxycarbonyldecyl) dimethylammonium bromide is obtained in a yield of 80%; mp
až 43 °C; Rp=0,54; IČ-spektrálne charakteristiky: -9 (CO) 1736, 9(C0C) 1177, 9(CN) 1105 cm1.up to 43 ° C; R p = 0.54; IR spectral characteristics: -9 (CO) 1736.9 (CO) 1177.9 (CN) 1105 cm @ -1 .
Příklad 2Example 2
Pracovný postup je podobný ako v příklade 1, namiesto metylesteru kyseliny 11-brámundekánovej sa použil do reakoie hexylester. Výťažok N-dodecyl-(10-hexyloxykarbonyldecyl)dimetylaméniumbromidu je 83 X; t.t. 53 až 55 °C; Rp«0,50; IČ-spektrálne charakteristiky:The procedure is similar to that of Example 1, instead of methyl 11-bromo-decanoate, hexyl ester was used in the reaction. The yield of N-dodecyl (10-hexyloxycarbonyldecyl) dimethylamenium bromide is 83%; mp 53-55 ° C; Rp = 0.50; IR spectral characteristics:
9(C0) 1735, 9(COC) 1184, 9(CN) 1119 cm“1. ”9 (C0) 1735, 9 (COC) 1184, 9 (CN) 1119 cm -1 . "
Příklad 3Example 3
Pracovný postup je podobný ako v přiklade 1, do reakoie sa vSak použil benzylester kyseliny 11-brámundekánovej. N-dodecyl-(lO-benzyloxykarbonyldecyl)dimetylamániumbromid vzniká volvýtažku 80 X; t.t. 44 až 46 °C; Rp=0,55; IČ-spektrálne charakteristiky:9(CO) 1735. 9(C0C) 1171, 9(CN) 1116 cm1.The procedure is similar to Example 1 except that the benzyl ester of 11-bromo-decanoic acid was used. N-dodecyl- (10-benzyloxycarbonyldecyl) dimethylamanumbromide is obtained in yield 80%; mp 44-46 ° C; R p = 0.55; IR spectral characteristics: 9 (CO) 1735.9 (CO) 1171.9 (CN) 1116 cm @ -1 .
VSetky takto připravené zlúčeniny sú biele, mimoriadne hygroskopické látky, rozpustné v polárných rozpúSťadlách, nerozpustné v petrolétere.All the compounds thus prepared are white, particularly hygroscopic substances, soluble in polar solvents, insoluble in petroleum ether.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS776278A CS200112B3 (en) | 1978-11-27 | 1978-11-27 | Process for preparing ammonium salts of esteres of 11-aminoundecanoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS776278A CS200112B3 (en) | 1978-11-27 | 1978-11-27 | Process for preparing ammonium salts of esteres of 11-aminoundecanoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200112B3 true CS200112B3 (en) | 1980-08-29 |
Family
ID=5427305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS776278A CS200112B3 (en) | 1978-11-27 | 1978-11-27 | Process for preparing ammonium salts of esteres of 11-aminoundecanoic acid |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS200112B3 (en) |
-
1978
- 1978-11-27 CS CS776278A patent/CS200112B3/en unknown
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