DE1150392B - Process for the production of organic sulfite-ammonium compounds - Google Patents

Process for the production of organic sulfite-ammonium compounds

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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
Application number
DEF32017A
Other languages
German (de)
Inventor
Dr Werner Blank
Dr Dietrich Glabisch
Dr Martin Wandel
Dr Josef Witte
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to DEF30243A priority Critical patent/DE1154268B/en
Priority to DEF30242A priority patent/DE1150095B/en
Application filed by Bayer AG filed Critical Bayer AG
Priority to DEF32017A priority patent/DE1150392B/en
Priority to CH1346061A priority patent/CH374704A/en
Priority to CH1421560A priority patent/CH370522A/en
Priority to US79139A priority patent/US3168546A/en
Priority to GB575/61A priority patent/GB965246A/en
Priority to FR848942A priority patent/FR1277234A/en
Priority to BE598917A priority patent/BE598917A/en
Publication of DE1150392B publication Critical patent/DE1150392B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C301/00—Esters of sulfurous acid

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  • 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: Berechnet ... C 59,8, H 10,9, N 4,36; gefunden ... C59,5, H11,1, N4,05, 59,2, 11,2, 4,07. Beispiel 2 Unter den Reaktionsbedingungen des Beispiels 1 erhält man aus 149 Teilen Triäthanolamin und 108 Teilen Glykolsulfit 250 g eines dickflüssigen Öls, das in Wasser löslich ist und reduzierende Eigenschaften zeigt. Für die Summenformel C,H1aOBNS (Molgewicht 257) erhält man folgende Analysenwerte: Berechnet ... C 37,4, H 7,38, N 5,44; gefunden ... C 37,8, H 7,4, N 5,35. 37,7, 7,7, The parts mentioned in the following examples are parts by weight. Example 1 108 parts of glycol sulfite are added dropwise to 213 parts of N-dodecyl-N, N-dimethylamine over 1/3 hour with moderate stirring at 140.degree. After cooling to room temperature, 320 parts of a solid, almost colorless, soap-like substance are obtained, which is soluble in water with strong foaming, potassium permangenate solution and decolorized for the compound of the formula C "H" 03NS (molecular weight = 321) provides the following analysis values: Calculated ... C 59.8, H 10.9, N 4.36; found ... C59.5, H11.1, N4.05, 59.2, 11.2, 4.07. Example 2 Under the reaction conditions of Example 1, from 149 parts of triethanolamine and 108 parts of glycol sulfite, 250 g of a viscous oil which is soluble in water and shows reducing properties are obtained. The following analysis values are obtained for the empirical formula C, H1aOBNS (molecular weight 257): Calculated ... C 37.4, H 7.38, N 5.44; Found ... C 37.8, H 7.4, N 5.35. 37.7, 7.7,

Claims (2)

PATENTANSPRÜCHE: 1. Verfahren zur Herstellung von organischen Sulfit-Ammonium-Verbindungen, dadurch gekennzeichnet, daß man bei erhöhter Temperatur, vorzugsweise bei Temperaturen oberhalb 100°C, ein Glykolsulfit mit tertiären Aminen, deren Substituenten Alkylreste darstellen, die freie, verätherte und/oder veresterte Hydroxylgruppen und/ oder carbocyclische und/oder heterocyclische Reste tragen können, umsetzt. PATENT CLAIMS: 1. Process for the production of organic sulfite-ammonium compounds, characterized in that at elevated temperature, preferably at temperatures above 100 ° C, a glycol sulfite with tertiary amines, whose substituents are alkyl radicals represent, the free, etherified and / or esterified hydroxyl groups and / or can carry carbocyclic and / or heterocyclic radicals, converts. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die Ausgangskomponenten in annähernd äquimolaren Mengenverhältnissen umsetzt.2. Procedure according to claim 1, characterized in that the starting components in approximately converts equimolar proportions.
DEF32017A 1960-01-07 1960-09-01 Process for the production of organic sulfite-ammonium compounds Pending DE1150392B (en)

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
CH1346061A CH374704A (en) 1960-01-07 1960-12-20 Process for the preparation of sulfurous acid esters
CH1421560A CH370522A (en) 1960-01-07 1960-12-20 Process for rendering fibers made of synthetic high polymers antistatic
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)

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