CS256557B1 - Method of hexamethylentetraminium quaternary salts preparation - Google Patents
Method of hexamethylentetraminium quaternary salts preparation Download PDFInfo
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- CS256557B1 CS256557B1 CS85271A CS27185A CS256557B1 CS 256557 B1 CS256557 B1 CS 256557B1 CS 85271 A CS85271 A CS 85271A CS 27185 A CS27185 A CS 27185A CS 256557 B1 CS256557 B1 CS 256557B1
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- CS
- Czechoslovakia
- Prior art keywords
- hexamethylenetetramine
- quaternary salts
- formula
- coor
- hexamethylentetraminium
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 10
- 150000003839 salts Chemical group 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 10
- 239000004312 hexamethylene tetramine Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 238000001238 wet grinding Methods 0.000 claims abstract description 3
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract description 2
- 230000000855 fungicidal effect Effects 0.000 abstract description 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000010779 crude oil Substances 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- -1 ester salts Chemical class 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Spósob přípravy hexametyléntetramíniových kvartérnych solí vzorca: N· N CH?COOR X -N Θ reakciou hexametyléntetramínu s halogénacetátmi vzorca: X—CH?—COOR, kde X je Br, CI alebo I a R je alkyl s 1 až 4 atómami uhlíka. Podstatou vynálezu je tá skutočnosť, že pri teplote 0 až 120 °C, v procese mokrého mletia, po dobu 1 až 120 minút sa pósobí na 1 molárny diel kvapalného halogénacetátu, pri absencii rozpúšťadla, 1 molárnym dielom hexametyléntetramínu. Získané produkty sú vhodné ako baktericídne a fungicídne přísady do náterov, latexov, lepidiel, režných olejov a pod.A method for preparing hexamethylenetetramines quaternary salts of formula: N · N CH 2 COOR X -N Θ by reacting hexamethylenetetramine with haloacetates formula: X — CH? —COOR, where X is Br, Cl or I and R is alkyl of 1 to 1 4 carbon atoms. The essence of the invention is that the fact that at 0 to 120 ° C, v wet milling process for 1 to 120 hours minutes to 1 molar liquid haloacetate, in the absence of a solvent 1 molar portion of hexamethylenetetramine. The products obtained are suitable as bactericidal and fungicidal coatings, latexes, adhesives, crude oils and the like.
Description
Uvedené nedostatky rieši tento vynález, podlá ktorého spósob přípravy kvartérnych solí vzorca:The above-mentioned drawbacks are solved by the present invention, according to which method for the preparation of quaternary salts of the formula:
N-Νχ\ V-CHfCOQRX ι V/ <reakciou hexametyléntetramínu s halogénacetátmi vzorca:N-Νχ \ V-CHfCOQRX ι V / <by reaction of hexamethylenetetramine with haloacetates of formula:
X—CH2—COOR, kde , X je Br, Cl alebo I a R je alkyl s 1 až 4 atómami uhlíka, sa uskutočňuje tak, že pri teplote 0° až 120 °C, v procese mokrého mletía, po dobu 1 až 120 minút, sa působí na 1 molárny diel kvapalného halogénacetátu, při absencíi rozpúšťadla, 1 molárnym dielom hexametyléntetramínu.X - CH 2 - COOR, wherein, X is Br, Cl or I and R is alkyl of 1 to 4 carbon atoms, is carried out such that at 0 ° to 120 ° C, in a wet milling process, for 1 to 120 minutes, 1 molar part of liquid haloacetate is treated with 1 molar part of hexamethylenetetramine in the absence of solvent.
Pokrok vynálezu sa prejavuje technickými účinkamí, najmá skrátením reakčného času a odstránením problémov práce s rozpúšťadlami.The progress of the invention is manifested by technical effects, in particular by reducing the reaction time and eliminating the problems of working with solvents.
Hospodářsky pokrok riešenia sa prejavuje znížením výrobných nákladov, zlevněním výrobkov, znížením prácnosti, úsporou surovin, energie atd.The economic progress of the solution is reflected in the reduction of production costs, reduction of products, reduction of labor, saving of raw materials, energy etc.
Z hradiska společenského má význam aj zvýšenie bezpečnosti práce a zlepšenie hygienických podmienok v spojitosti so zamořením pracovného a životného prostredia haloderivátmi.Increasing work safety and hygiene conditions in connection with contamination of work and the environment with haloderivatives are also important from the social point of view.
V tomto tzv. „slurry procese“ je možné podlá povahy halogénacetátu volit malý prebytok jednej zo vstupujúcich reaktans, ktorý sa neprejaví na znížení účinku výrobku.In this so-called. According to the "slurry process", depending on the nature of the haloacetate, a small excess of one of the incoming reactants can be selected which does not result in a reduction in the product's effect.
Příprava kvartérnych solí v zmysle vynálezu je dokumentovaná nasledujúcimi príkladmi, ktoré však v žiadnom případe nevylučujú možnosť variability přípravy předmětných substanci!.The preparation of quaternary salts according to the invention is illustrated by the following examples, which in no way exclude the possibility of variability in the preparation of the subject substances.
Příklad 1Example 1
Do šnekového malaxéru z neiskrivej ocele s objemom 500 cm3 sa nasype 140,0 g hexametyléntetramínu (1 mól). Pri laboratórnej teplote 24 °C za stálého miešania sa postupné dávkuje 167,0 g (1 mól) etylesteru kyseliny brómoctovej cez stádium kaše, ktorá sa ohrieva uvolněným kvarternizačným teplom udržiayaním na hodnotě 70 °C. Po hodině malaxovania sa produkt pomelie. Rezultuje 306,0 g kvartémej soli, to je 99,7 % oproti teórii.140.0 g of hexamethylenetetramine (1 mol) are poured into a 500 cm 3 stainless steel screw malaxer. 167.0 g (1 mol) of ethyl bromoacetate are successively metered in at room temperature 24 ° C with stirring and heated to 70 ° C by the liberated quaternization heat. After an hour of malaxing, the product is ground. This results in 306.0 g of quaternary salt, which is 99.7% of theory.
Poznámka: uvolněné reakčné teplo móže spósobiť zvýšenie teploty, ktorá přesahuje teplotu rozkladu produktu.Note: the released heat of reaction may cause an increase in temperature that exceeds the decomposition temperature of the product.
Pomocou diferenčnej termickej analýzy (DTA), pracujúcej s rýchlosfou lineárneho vzostupu teploty 5 °C. min-1, meracím rozsahom 1 mV na škálu stupnice a navážkami 50 až 70 mg vzorky je najdený počiatok exotermického rozkladu v pevnom skupenstve pri 117,0 °C. Ďalej prvý pík exo-rozkladu pri 142,4 °C; endo-pík při 146,0 °C a druhý pík exo-rozkladu při 150,6 °C. K zmene charakteru rozkladu dochádza pri teplote 135,2 °C.Using differential thermal analysis (DTA), operating at a linear temperature rise rate of 5 ° C. min -1 , with a measuring range of 1 mV per scale scale and weighing 50 to 70 mg of sample, the onset of exothermic solid state decomposition at 117.0 ° C is found. Furthermore, the first peak of exo-decomposition at 142.4 ° C; endo-peak at 146.0 ° C and second exo-decomposition peak at 150.6 ° C. The decomposition pattern changes at 135.2 ° C.
Stanovená teplota topenia vzorky na mikrovýhrevnom stolku „Boetius“ je 142—143 stupňov C.The melting point of the specimen on the "Boetius" micro-heating plate is 142-143 degrees C.
Produkt má v IČ-spektre dvojicu esterových pásov cca 1 740 a 1 290 cm-1 a štvoricu „urotropínových“ pásov (s nepatrnými posunml). Pásy medzi 3 000—2 800 cm-1 patria valenčným vibráciam C—H vázieb, podlá očakávania najsilnejšie sú i>as CH2 pca 2 920 cm-1. V oblosti deformačných vibřácií C—H vázieb je tiež najsilnejší pás S Chi sciccor cca 1 470 cm-1 a přítomný je tiež pás tzv. aktívnych CH2 skupin cca 1 410 cm-1 (aktivně = vedla skupin s — I efektomj. Příklad 2The product has a pair of ester bands of approx. 1,740 and 1,290 cm -1 in the IR spectrum and four "urotropin" bands (with a slight shift). Bands between 3,000-2,800 cm -1 belong to the valence vibrations of the C-H bonds, and as expected, the strongest are i> as CH2 pca of 2,920 cm -1 . In the area of deformation vibrations of the C — H bonds, the strongest belt S Chi sciccor is also approximately 1,470 cm -1 and a belt called so-called. active CH2 groups of about 1410 cm -1 (actively = led to groups with - I effect)
Postupuje sa ako v příklade 1, len s tým rozdielom, že sú použité estery s róznym R. Výsledky sú zhrnuté v tabulke 1.The procedure is as in Example 1, except that esters with different R-values are used. The results are summarized in Table 1.
Tabulka 1Table 1
Pokusattempt
č.no.
Výťažok (%)Yield (%)
Teplota topenia (°C)Melting point (° C)
JJ
251557251557
Za obdobných podmienok s rovnakým účinkom vznikajú kvartérne soli s esterml, v ktorých R je 2,3-dichlórallyl, n-butyl, respektive izobutyl pre X = Cl alebo I.Under similar conditions with the same effect, quaternary ester salts are formed in which R is 2,3-dichloroallyl, n-butyl and isobutyl, respectively, for X = Cl or I.
Získané produkty postupom pódia vynálezu sú vhodné ako bakteriocídne a fungicídne přísady do náterov, latexov, lepidiel, řezných olejov a pod.The products obtained by the process according to the invention are suitable as bacteriocidal and fungicidal additives for coatings, latexes, adhesives, cutting oils and the like.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS85271A CS256557B1 (en) | 1985-01-14 | 1985-01-14 | Method of hexamethylentetraminium quaternary salts preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS85271A CS256557B1 (en) | 1985-01-14 | 1985-01-14 | Method of hexamethylentetraminium quaternary salts preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS27185A1 CS27185A1 (en) | 1987-09-17 |
| CS256557B1 true CS256557B1 (en) | 1988-04-15 |
Family
ID=5334546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS85271A CS256557B1 (en) | 1985-01-14 | 1985-01-14 | Method of hexamethylentetraminium quaternary salts preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS256557B1 (en) |
-
1985
- 1985-01-14 CS CS85271A patent/CS256557B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS27185A1 (en) | 1987-09-17 |
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