CS195360B1 - Method of producing n,n'-dimethyl-1,2-propandiamine - Google Patents
Method of producing n,n'-dimethyl-1,2-propandiamine Download PDFInfo
- Publication number
- CS195360B1 CS195360B1 CS484878A CS484878A CS195360B1 CS 195360 B1 CS195360 B1 CS 195360B1 CS 484878 A CS484878 A CS 484878A CS 484878 A CS484878 A CS 484878A CS 195360 B1 CS195360 B1 CS 195360B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dimethyl
- propanediamine
- propandiamine
- producing
- distilled
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- -1 benzylidene methylene salt Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XFNJYAKDBJUJAJ-UHFFFAOYSA-N 1,2-dibromopropane Chemical compound CC(Br)CBr XFNJYAKDBJUJAJ-UHFFFAOYSA-N 0.000 description 1
- RDHNFSNXWLWMIX-UHFFFAOYSA-N 1-n,2-n-dimethylpropane-1,2-diamine Chemical compound CNCC(C)NC RDHNFSNXWLWMIX-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- OVQABVAKPIYHIG-UHFFFAOYSA-N n-(benzenesulfonyl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NS(=O)(=O)C1=CC=CC=C1 OVQABVAKPIYHIG-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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
Vynález sa týka spôsobu prípravy N,N’--dimetyl-1,2-propándiamínu vzorca
Táto zlúčenina má využitie v priemysle napr. ako senzitív do fotografických emulzií, ale aj ako východisková surovina pre prípravy jej ďalších derivátov, ktoré vykazujú výrazné biologické účinky, medzi iným aj na rôzne kmene mikroorganizmov'. V súčasnosti je známych níekolko metód prípravy tejto zlúčeniny, ktoré však dávajú relatívne nízke výtažky, prípadne pri reakcii vznikajú nejednotné produkty /napr. pôsobením metylamínu na 1,2-dibrompropán, zahrievaním roztoku glukózy alebo sacharózy s metylamínom v metanole za prítomnosti vodíka na niklovom katalyzátore pri 100 až 200 °C a tlaku 10 až 20 MPa, redukciou príslušného dibenzénsulfónamidu s LÍAIH4/.
Uvedené nevýhody odstraňuje spôsob podlá vynálezu, ktorého podstatou je, že sa v jednom stupni cestou troch medziproduktov pripravených reakciou 1,2-propándiaminu s benzaldehydora a následnou alkyláciou dimetylsulf átom vzniknutá amóniová sol bis/benzylidénmetyl/-1,2-propándiaminu hydrolyzuje koncentrovanou kyselinou sírovou. Výsledný produkt vzniká vo výtažku až 80 % teór ie .
Príklad ->K 0,5 mol 1 , 2-propándiamínu rozpusteného v 200 ml benzénu sa za laboratórnej teploty prileje 1,2 mol benzaldehydu. Zmes sa zahrieva pod spätným tokom 30 min, potom sa benzén vákuové oddestiluje. K odparku sa za miešania pridá 1,2 mol dimetylsulfá-tu v 400 ml benzénu. Zahrieva sa pod spätným tokom 1 h, za vákua sa oddestiluje nezreago-vaný dimetylsulfát a benzén a k zbytku sa pridá 400 ml vody a 1 mol 98% H2SO4. Povarí sa 1 h a destiluje sa s vodnou parou. Po ochladení sa za miešania pridá pevný NaOH, amin sa extrahuje éterom a po vysušení éterických extraktov sa rozpúšťadlo oddestílu-je a produkt sa predest iluj e. Získa sa produkt vo výtažku 80 % teórie, t.v. 42 až 44 °C/2,4 kPa, η$θ= 1 , 4310.IČ-spektrá lne charakteristiky: V /NH/ Široký pás s maximom pri 3 280 cm“1, <T/NH/ široký intenzívny pás s maximom pri 780 cm”1, V /CN/ dublet ostrých pásov 1W0 a 1145 cm“1.
Claims (1)
- PREDMET VYNÁLEZU Spôsob prípravy N,N*-dimetyl-1,2-propán· diamínu vyznačujúci sa tým, že sa nechá zreagovať 1,2-propándiamín s benzaldehydom a následnou alkyláciou dimetylsulfátom vznikajúca araóniová sol b i s/benzylidénmety1/--1,2-propándiamínu sa za varu hydrolyzuje koncentrovanou kyselinou sírovou.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS484878A CS195360B1 (en) | 1978-07-20 | 1978-07-20 | Method of producing n,n'-dimethyl-1,2-propandiamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS484878A CS195360B1 (en) | 1978-07-20 | 1978-07-20 | Method of producing n,n'-dimethyl-1,2-propandiamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195360B1 true CS195360B1 (en) | 1980-01-31 |
Family
ID=5392139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS484878A CS195360B1 (en) | 1978-07-20 | 1978-07-20 | Method of producing n,n'-dimethyl-1,2-propandiamine |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS195360B1 (cs) |
-
1978
- 1978-07-20 CS CS484878A patent/CS195360B1/cs unknown
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