CS200992B1 - Method of preparing n,n-dimethyl-1,3-propanediamine - Google Patents
Method of preparing n,n-dimethyl-1,3-propanediamine Download PDFInfo
- Publication number
- CS200992B1 CS200992B1 CS175579A CS175579A CS200992B1 CS 200992 B1 CS200992 B1 CS 200992B1 CS 175579 A CS175579 A CS 175579A CS 175579 A CS175579 A CS 175579A CS 200992 B1 CS200992 B1 CS 200992B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- propanediamine
- dimethyl
- preparing
- bis
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 title 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 8
- 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
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-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
- UQUPIHHYKUEXQD-UHFFFAOYSA-N n,n′-dimethyl-1,3-propanediamine Chemical compound CNCCCNC UQUPIHHYKUEXQD-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- -1 bis (benzylidenemethyl) -1,3-propanediamine Chemical compound 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- RXLUOFXICZSZIB-UHFFFAOYSA-N n,n'-dibenzylpropane-1,3-diamine Chemical compound C=1C=CC=CC=1CNCCCNCC1=CC=CC=C1 RXLUOFXICZSZIB-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález sa týká spósobu přípravy N,N'-dimetyl-l,3-propándiamínu vzorca ch3-nh-(ch2)3-nh-ch3 The present invention relates to a process for the preparation of N, N'-dimethyl-1,3-propanediamine of the formula ch 3 -nh- (ch 2 ) 3 -nh-ch 3
Táto zlúčenina sa využívá v priemysle napr. ako monomér pri kopolymerizáciách, ako antioxidant, stabilizátor do fotoemulzií, ale aj ako východisková surovina pri príprave dalších jej derivátov, ktoré vykazujú medzi iným aj účinky na živé organizmy, predovšetkým letálne účinky na mikroorganizmy. V súčasnosti je známých niekofko metód přípravy tejto zlúčeniny, ktoré však majú tú nevýhodu, že buď dóvajú nízké výtažky, alebo sa jedná o viacstupňovú syntézu spojená s niekolkonásobnou izoláciou medziproduktov. Takto sa například připravuje z N,N'-bis(fenylmetyl)-l,3-propándiamínu diazotáciou s NáNOg a HC1, připadne z 1,3-dibrómpropánu a vodno-etanolického roztoku metylamínu. V oboch prípadoch vznikajú produkty nízkej čistoty a. v nízkých výťažkoch.This compound is used in industry e.g. as a monomer in copolymerizations, as an antioxidant, a stabilizer for photoemulsions, but also as a starting material in the preparation of other derivatives thereof which exhibit inter alia effects on living organisms, in particular lethal effects on microorganisms. Several methods for the preparation of this compound are currently known, but have the disadvantage of either yielding low yields or a multi-step synthesis associated with multiple isolation of intermediates. Thus, for example, it is prepared from N, N'-bis (phenylmethyl) -1,3-propanediamine by diazotization with NaNO2 and HCl, optionally from 1,3-dibromopropane and an aqueous-ethanolic solution of methylamine. In both cases, low purity products are produced and. in low yields.
Uvedené nevýhody odstraňuje spósob podlá vynálezu, ktorého podstatou je, že sa v jednej aparatúre cestou troch medziproduktov, ktoré sa neizolujú, hydrolýzou amóniovej soli bis(benzylidénmetyl)-l,3-propándiamlnu,' pripravenej z 1,3-propándiamínu a benzaldehydu s následnou alkyláciou dimetylsulfátom, koncentrovanou kyselinou sírovou připraví produkt vo výtažku až 85 % teórie.The above-mentioned disadvantages are overcome by the method according to the invention, which consists in the fact that in one apparatus by way of three non-isolated intermediates, hydrolysis of the ammonium salt of bis (benzylidenemethyl) -1,3-propanediamine prepared from 1,3-propanediamine and benzaldehyde followed by alkylation with dimethyl sulphate, concentrated sulfuric acid affords the product in up to 85% of theory.
200 992200 992
200 092200 092
PříkladExample
0,5 mol 1,3-propándiaminu sa v 200 ml suchého benzénu zmieša s 1,2 mol benzaldehydu. Zmes sa povarí 30 minút, potom sa reakčná voda a benzém oddestilujú. K takto vzniknutej Schiffovej zásadě sa přidá 1,2-mol dimetylsulfátu v 400 ml benzénu. Po přidaní všetkého alkylačného činidla sa reakčná zmes povarí 1 hodinu. Po tomto čase sa benzén a nezreagovaný dimetylsulfát oddestiluje a k reakčnému zvyšku, ktorým je amóniová sol bis(benzylidénmetyl)-l,3-propándiamínu, sa přidá 400 ml vody a 1 mol koncentrovanej kyseliny sírovej. Povarí sa 1 hodinu a reakčná zmes sa podrobí destilácii s vodnou parou. K zvyšku po destilácii sa priďá pevný NaOH a po oddělení vrstiev sa amin extrahuje éterom. Po vysušení extraktov a. oddestilovaní éteru sa amin predestiluje. Získá sa produkt vo výtažku 85 % teórie /počítané na východiskový 1,3-propándiamln/. T.v. 142 až 145 °C/101,3 kPa; n^~ 1,4428; IČ-spektrálne charakteristiky; 1?(NH) intenzívny pás 3280 cm1, <f{NH) intenzívny pás T40 cm1, 9 (If-CHO) 2690 cm“1, ÝfC-N) intenzívny dublet pásov 1140,1120 cm-1 /namerané v pdvodnora stave ako film/.0.5 mol of 1,3-propanediamine is mixed with 1.2 mol of benzaldehyde in 200 ml of dry benzene. The mixture was boiled for 30 minutes, then the reaction water and benzene were distilled off. To the Schiff base thus formed was added 1,2-mol dimethyl sulfate in 400 ml benzene. After all the alkylating agent had been added, the reaction mixture was boiled for 1 hour. After this time, benzene and unreacted dimethyl sulfate are distilled off and 400 ml of water and 1 mol of concentrated sulfuric acid are added to the reaction residue, which is the ammonium salt of bis (benzylidenemethyl) -1,3-propanediamine. Boil for 1 hour and distill the reaction mixture with steam. Solid NaOH was added to the distillation residue and after separation of the layers, the amine was extracted with ether. After drying the extracts and. distilling off the ether distilled the amine. The product is obtained in a yield of 85% of theory (calculated on the starting 1,3-propanediamine). Mp 142-145 ° C / 101.3 kPa; n = 1.4428; IR spectral characteristics; 1? (NH) 3280 cm intense band 1, <f {NH) intense band T40 cm 1 9 (If CH-O) 2690 cm "1, N-YFC) intense doublet bands 1140.1120 cm -1 / measured in status as a film.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS175579A CS200992B1 (en) | 1979-03-16 | 1979-03-16 | Method of preparing n,n-dimethyl-1,3-propanediamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS175579A CS200992B1 (en) | 1979-03-16 | 1979-03-16 | Method of preparing n,n-dimethyl-1,3-propanediamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200992B1 true CS200992B1 (en) | 1980-10-31 |
Family
ID=5352725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS175579A CS200992B1 (en) | 1979-03-16 | 1979-03-16 | Method of preparing n,n-dimethyl-1,3-propanediamine |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS200992B1 (en) |
-
1979
- 1979-03-16 CS CS175579A patent/CS200992B1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2818433A (en) | Process for making methylenedianilines | |
| Buc et al. | An improved synthesis of β-alanine | |
| CA1099272A (en) | Process for preparing 2,2,6,6-tetramethyl-4- piperidone | |
| US2974168A (en) | Process for making methylenedianiline | |
| US2850519A (en) | Process for the production of alpha-monocyanethylated ketones | |
| SU686616A3 (en) | Method of producing derivatives of 3-fluro-6-piperazyl-morphanthridine or their salts | |
| CS200992B1 (en) | Method of preparing n,n-dimethyl-1,3-propanediamine | |
| RU2017726C1 (en) | Method of imidodiacetonitrile synthesis | |
| US3413309A (en) | Process for preparing nitriles of cycloaliphatic or heterocyclic acids | |
| ES477114A1 (en) | Process for the preparation of ortho-isomer-rich polyamines of the diphenyl methane series. | |
| RU2155186C1 (en) | Method of preparing didecyl dimethyl ammonium bromide | |
| US2526517A (en) | N-methylol maleimide | |
| US4552699A (en) | Process for the preparation of 3-acylaminoanilines | |
| SU426362A3 (en) | METHOD FOR OBTAINING DICHLORBENZYLTHYOETHYLAMINES | |
| US4150054A (en) | N-akylation of aromatic amines in the presence of an aliphatic amino compound | |
| US5457233A (en) | Process for the preparation of amines | |
| JPS58206576A (en) | Manufacture of cis-2,6-dimethylmorpholine | |
| SU1664787A1 (en) | Method of producing 9,9-bis(4-amninophenyl)fluorene | |
| US3130218A (en) | Process for the preparation of 4-nitrostilbene carbonitriles | |
| US2785175A (en) | Imidazolidinethiones | |
| US4774358A (en) | Cyclopropylamines containing trifluoromethyl groups | |
| US2505682A (en) | Amides of alpha: beta-unsaturated carboxylic acids and a process of making same | |
| CS195215B1 (en) | Method of producing n,n'-dimethyl-1,2-ethandiamine | |
| CS198969B1 (en) | Process for preparing n,n'-dimethyl-1,5-pentandiamine | |
| SU455939A1 (en) | The method of obtaining the monoamine salts of fumaric or maleic acid |