DE1150392B - Process for the production of organic sulfite-ammonium compounds - Google Patents
Process for the production of organic sulfite-ammonium compoundsInfo
- Publication number
- DE1150392B DE1150392B DEF32017A DEF0032017A DE1150392B DE 1150392 B DE1150392 B DE 1150392B DE F32017 A DEF32017 A DE F32017A DE F0032017 A DEF0032017 A DE F0032017A DE 1150392 B DE1150392 B DE 1150392B
- Authority
- DE
- Germany
- Prior art keywords
- ammonium compounds
- production
- sulfite
- organic sulfite
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 5
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical class [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- -1 alkyl radicals Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical class CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- TZVYDYIDLQCRHV-UHFFFAOYSA-N 3-[ethyl(methyl)amino]propan-1-ol Chemical compound CCN(C)CCCO TZVYDYIDLQCRHV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical class CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- WOLFCKKMHUVEPN-UHFFFAOYSA-N n-ethyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CC WOLFCKKMHUVEPN-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C301/00—Esters of sulfurous acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von organischen Sulfit-Ammonium-Verbindungen Es ist bekannt, Äthylglykolsulfit als Oxäthylierungsagenz zu verwenden. So erhält man durch Umsatz von primären bzw. sekundären Aminen mit Glykolsulfit unter SO2-Abspaltung die entsprechenden Aminoäthanole.Process for the production of organic sulfite-ammonium compounds It is known to use ethyl glycol sulfite as an Oxäthylierungsagenz. So get by conversion of primary or secondary amines with glycol sulfite with splitting off of SO2 the corresponding aminoethanols.
Es wurde nun gefunden, daß ein Glykolsulfit überraschenderweise auch mit tertiären Aminen reagiert. Dabei entstehen nach dem folgenden Schema Betaine von Halbestern der schwefligen Säure (1): In den allgemeinen Formeln bedeuten die Reste R1, R2 und R3 Alkylreste, die freie, verätherte und/oder veresterte Hydroxylgruppen und/oder carbocyclische bzw. heterocyclische Reste tragen können; jeweils zwei der Reste R1, R2 bzw. R3 können auch unter Ausbildung eines heterocyclischen Ringes miteinander verknüpft sein; R steht für Wasserstoff oder einen niederen Alkyl- oder einen Arylrest.It has now been found that, surprisingly, a glycol sulfite also reacts with tertiary amines. This results in betaines from half-esters of sulphurous acid (1) according to the following scheme: In the general formulas, the radicals R1, R2 and R3 denote alkyl radicals which can carry free, etherified and / or esterified hydroxyl groups and / or carbocyclic or heterocyclic radicals; in each case two of the radicals R1, R2 or R3 can also be linked to one another to form a heterocyclic ring; R stands for hydrogen or a lower alkyl or aryl radical.
Geeignete Amine der Formel sind unter anderem Trialkyl- oder -isoalkylamine, Hydroxalkylalkylamine oder Trihydroxalkylamine, wie Trimethylamin, Triäthylamin, Isopropyldimeihylamin, Butyläthylmethylamin, Dihydroxäthylrnethylamin, ß- oder y-Hydroxypropylmethyläthylamin, Trihydroxäthylamin, ferner Ester, wie Carbonsäureester der Hydroxalkylamine, und Äther, wie Methyl-, Äthyl- und Propyläther der Hydroxalkylamine; als Aralkylamine sind beispielsweise Benzyldimethylamin, Benzylhydroxäthylmethylamin oder Benzyldihydroxäthylarnin zu nennen. Tertiäre Amine, in denen einer der Substituenten Al, R. oder R3 einen heterocyclischen Rest enthält, sind unter anderem 2-(Dimethyl- oder Methyläthylaminomethylen)-tetrahydrofuran; in Verbindungen, wie N-Methylpiperidin, N-Äthylpiperazin oder N-methyl- oder -äthylmorpholin, sind jeweils zwei der Substituenten R1, R2 bzw. R3 zu einem heterocyclischen Ring verknüpft.Suitable amines of the formula are inter alia trialkyl or isoalkylamines, hydroxyalkylalkylamines or trihydroxalkylamines, such as trimethylamine, triethylamine, isopropyldimeihylamine, butylethylmethylamine, dihydroxäthylmethylamine, β- or γ-hydroxypropylmethylethylamine, trihydroxyethylamine, and esters such as carboxylic acid esters of the hydroxyalkylamines and propyl ethers of the hydroxyalkylamines; as aralkylamines, for example, benzyldimethylamine, benzylhydroxäthylmethylamin or Benzyldihydroxäthylarnin are to be mentioned. Tertiary amines in which one of the substituents Al, R. or R3 contains a heterocyclic radical are, inter alia, 2- (dimethyl- or methylethylaminomethylene) tetrahydrofuran; in compounds such as N-methylpiperidine, N-ethylpiperazine or N-methyl- or -äthylmorpholine, two of the substituents R1, R2 and R3 are linked to form a heterocyclic ring.
Die Reaktion verläuft bei erhöhter Temperatur, vorzugsweise bei Temperaturen oberhalb 100°C, glatt und mit ausgezeichneter, häufig quantitativer Ausbeute. Die Umsetzung kann in Gegenwart oder in Abwesenheit von inerten Lösungsmitteln vorgenommen werden.The reaction takes place at an elevated temperature, preferably at temperatures above 100 ° C, smooth and with excellent, often quantitative, yield. the The reaction can be carried out in the presence or absence of inert solvents will.
Die verfahrensgemäß erhältlichen Sulfit-Ammonium-Verbindungen besitzen eine Reihe wertvoller Eigenschaften, beispielsweise gute Emulgator- oder desinfizierende Wirkung.The sulphite-ammonium compounds obtainable according to the process have a number of valuable properties, such as good emulsifying or disinfecting properties Effect.
Die in den folgenden Beispielen genannten Teile sind Gewichtsteile.
Beispiel 1 Zu 213 Teilen N-Dodecyl-N,N-dimethylamin tropft man innerhalb 1/3 Stunde
unter mäßigem Rühren bei 140°C 108 Teile Glykolsulfit. Nach dem Abkühlen auf Zimmertemperatur
erhält man 320 Teile einer festen, fast farblosen seifenartigen Substanz, die in
Wasser unter starker Schaumbildung löslich ist, Kaliumpermangenatlösung entfärbt
und für die Verbindung der Formel
C"H"03NS (Molgewicht = 321) folgende Analysenwerte liefert:
Claims (2)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30243A DE1154268B (en) | 1960-01-07 | 1960-01-07 | The prevention of electrostatic charges in synthetic high polymers |
| DEF30242A DE1150095B (en) | 1960-01-07 | 1960-01-07 | Process for the production of organic ammonium compounds |
| DEF32017A DE1150392B (en) | 1960-09-01 | 1960-09-01 | Process for the production of organic sulfite-ammonium compounds |
| CH1421560A CH370522A (en) | 1960-01-07 | 1960-12-20 | Process for rendering fibers made of synthetic high polymers antistatic |
| CH1346061A CH374704A (en) | 1960-01-07 | 1960-12-20 | Process for the preparation of sulfurous acid esters |
| US79139A US3168546A (en) | 1960-01-07 | 1960-12-29 | Organic ammonium sulfite ester compounds and method of preparation |
| GB575/61A GB965246A (en) | 1960-01-07 | 1961-01-05 | Organic ammonium compounds |
| FR848942A FR1277234A (en) | 1960-01-07 | 1961-01-06 | Organic ammonium compounds |
| BE598917A BE598917A (en) | 1960-01-07 | 1961-01-09 | Organic ammonium compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF32017A DE1150392B (en) | 1960-09-01 | 1960-09-01 | Process for the production of organic sulfite-ammonium compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1150392B true DE1150392B (en) | 1963-06-20 |
Family
ID=7094455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF32017A Pending DE1150392B (en) | 1960-01-07 | 1960-09-01 | Process for the production of organic sulfite-ammonium compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1150392B (en) |
-
1960
- 1960-09-01 DE DEF32017A patent/DE1150392B/en active Pending
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