DE1178071B - Process for the preparation of a heterocyclic condensation product from vinyl sulfonamide and formaldehyde. - Google Patents

Process for the preparation of a heterocyclic condensation product from vinyl sulfonamide and formaldehyde.

Info

Publication number
DE1178071B
DE1178071B DE1961B0061293 DEB0061293A DE1178071B DE 1178071 B DE1178071 B DE 1178071B DE 1961B0061293 DE1961B0061293 DE 1961B0061293 DE B0061293 A DEB0061293 A DE B0061293A DE 1178071 B DE1178071 B DE 1178071B
Authority
DE
Germany
Prior art keywords
formaldehyde
preparation
condensation product
vinyl sulfonamide
heterocyclic condensation
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
DE1961B0061293
Other languages
German (de)
Inventor
Dr. Werner Rohland und Dr. Gerhard I.utzel Ludwigshafcn/Rhein Or. Dieter Ludsteck
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik 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
Application filed by BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Priority to DE1961B0061293 priority Critical patent/DE1178071B/en
Priority to BE613866A priority patent/BE613866A/en
Priority to GB578362A priority patent/GB951887A/en
Publication of DE1178071B publication Critical patent/DE1178071B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F28/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Internat. KL: C07d Boarding school KL: C07d

Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:

Deutsche Kl.: 12 ρ-10/05 German class: 12 ρ -10/05

B 61293 IVd/12 ρB 61293 IVd / 12 ρ

16. Februar 1961February 16, 1961

17. September 196417th September 1964

Es ist bekannt, daß α,β-ungesättigte Nitrile, ζ. Β. Acrylnitril, bei der Kondensation mit Formaldehyd ungesättigte Hexahydro-l,3,5-triazinderivate liefern (Ber., 81, 528 [1948]). Acrylsäureamid liefert bei der Kondensation mit Formaldehyd die Bis-acrylamidmethylenverbindung (USA.-Patentschrift 2 475 846). Ferner ist bekannt, daß gesättigte Sulfonsäureamide mit Formaldehyd cyclische Hexahydrotriazinderivate liefern (Am. Soc, 56, 204 [1934]).It is known that α, β-unsaturated nitriles, ζ. Β. Acrylonitrile, on condensation with formaldehyde, give unsaturated hexahydro-1,3,5-triazine derivatives (Ber., 81, 528 [1948]). Acrylic acid amide yields the bis-acrylamide-methylene compound on condensation with formaldehyde (U.S. Patent 2,475,846). It is also known that saturated sulfonic acid amides give cyclic hexahydrotriazine derivatives with formaldehyde (Am. Soc, 56, 204 [1934]).

Es wurde nun überraschenderweise gefunden, daß man ein heterocyclisches Kondensationsprodukt erhält, wenn man Vinylsulfonamid mit etwa molaren Mengen (bezogen auf monomeren Formaldehyd) Paraformaldehyd in Gegenwart geringer Mengen konzentrierter Schwefelsäure auf 70 bis 10O0C erhitzt.It has now surprisingly been found that there is obtained a heterocyclic condensation product by heating vinylsulfonamide with approximately equimolar amounts (based on monomeric formaldehyde) of paraformaldehyde in concentrated sulfuric acid to the presence of small quantities of 70 to 10O 0 C.

Eine Herstellungsmöglichkeit des Vinylsulfonamids wird in Journal org. Chem., 23,729 [1958] beschrieben.A production possibility of the vinyl sulfonamide is in Journal org. Chem., 23,729 [1958].

Nach Beendigung der Kondensation, die etwa V2 bis 2 Stunden dauert, wird das Reaktionsgemisch abgestumpft, neutralisiert oder schwach alkalisch gemacht. Das Kondensationsprodukt dem wahrscheinlich die FormelAfter the end of the condensation, which lasts about V2 to 2 hours, the reaction mixture is blunted, neutralized or made weakly alkaline. The condensation product that probably the formula

H2
/CvH 2
/ Cv

CH2=CH-SO2-N
H2CCH 2 = CH-SO 2 -N
H 2 C

N-SO2-CH = CH2 CH2 N-SO 2 -CH = CH 2 CH 2

SN/ S N /

Verfahren zur Herstellung eines heterocyclischen Kondensationsproduktes aus
Vinylsulfonamid und FormaldehydProcess for the preparation of a heterocyclic condensation product from
Vinyl sulfonamide and formaldehyde

Anmelder:Applicant:

BadischeBadische

Anilin- & Soda-Fabrik Aktiengesellschaft,Aniline & Soda Factory Public Company,

Ludwigshafen/RheinLudwigshafen / Rhine

Als Erfinder benannt:Named as inventor:

Dr. Dieter Ludsteck,Dr. Dieter Ludsteck,

Dr. Werner Rohland,Dr. Werner Rohland,

Dr. Gerhard Lützel, Ludwigshafen/RheinDr. Gerhard Lützel, Ludwigshafen / Rhine

SO2-CH = CH2 SO 2 -CH = CH 2

entspricht, wird abgesaugt und mit Wasser gewaschen. Es ist farblos und zersetzt sich zwischen 130 und 2000C.corresponds, is suctioned off and washed with water. It is colorless and decomposes between 130 and 200 0 C.

Das Produkt kann zur Herstellung von Polymerisaten dienen.The product can be used to produce polymers.

Es war nicht vorauszusehen, daß die sehr reaktionsfähige Vinylgruppe des Vinylsulfonamids unter den Kondensationsbedingungen beständig ist, zumal im selben Molekül, im Gegensatz zum Acrylnitril, zwei alkylierbare Wasserstoffatome vorhanden sind und es bekannt ist, daß die Vinylsulfonylgruppe CH2 = CH2 — SO2 — reaktionsfähiger als die Vinylcarboxylgruppe CH2 = CH2 — CO— ist.It could not be foreseen that the very reactive vinyl group of vinylsulfonamide is stable under the condensation conditions, especially since in the same molecule, in contrast to acrylonitrile, there are two alkylatable hydrogen atoms and it is known that the vinylsulfonyl group CH2 = CH 2 - SO 2 - is more reactive as the vinyl carboxyl group is CH 2 = CH 2 - CO-.

Die in dem Beispiel genannten Teile sind Gewichtsteile. The parts mentioned in the example are parts by weight.

Beispielexample

Teile Vinylsulfonamid werden mit 15 Teilen Paraformaldehyd und 0,8 Teilen konzentrierter Schwefelsäure U/2 Stunden auf 80 bis 85° C erwärmt. Der erhaltene klare, etwas gelbliche Sirup wird anschließend so lange mit 10%iger Natronlauge gerührt, bis alles Produkt fest geworden ist. Man saugt ab und wäscht das Produkt mit Wasser alkalifrei. Man erhält nach dem Trocknen 48 Teile farbloses Produkt (das sind 80% der Theorie). Der Zersetzungspunkt des Produktes variiert je nach Art des Erhitzens in Schmelzpunktröhrchen von bis 2000C.
Analyse:Parts of vinyl sulfonamide are heated to 80 to 85 ° C. with 15 parts of paraformaldehyde and 0.8 part of concentrated sulfuric acid U / 2 hours. The clear, somewhat yellowish syrup obtained is then stirred with 10% sodium hydroxide solution until all of the product has solidified. The product is filtered off with suction and washed alkali-free with water. After drying, 48 parts of colorless product are obtained (that is 80% of theory). The decomposition point of the product varies depending on the type of heating in melting point tubes from up to 200 ° C.
Analysis:

BerechnetCalculated

gefundenfound

C 30,2%, H 4,3%, N 11,7%;
C 29,8%, H 4,6%, N 11,2%.C 30.2%, H 4.3%, N 11.7%;
C 29.8%, H 4.6%, N 11.2%.

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung eines heterocyclischen Kondensationsproduktes, dadurch gekennzeichnet, daß man Vinylsulfonamid mit etwa molaren Mengen (bezogen auf monomeren Formaldehyd) Paraformaldehyd in Gegenwart geringer Mengen konzentrierter Schwefelsäure auf 70 bis 100° C erhitzt.Process for the preparation of a heterocyclic condensation product, characterized in that that vinyl sulfonamide with approximately molar amounts (based on monomeric formaldehyde) paraformaldehyde in the presence small amounts of concentrated sulfuric acid heated to 70 to 100 ° C. In Betracht gezogene Druckschriften:
Chem. Berichte, 81 (1948), S. 529.Considered publications:
Chem. Reports, 81 (1948), p. 529.
DE1961B0061293 1961-02-16 1961-02-16 Process for the preparation of a heterocyclic condensation product from vinyl sulfonamide and formaldehyde. Pending DE1178071B (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE1961B0061293 DE1178071B (en) 1961-02-16 1961-02-16 Process for the preparation of a heterocyclic condensation product from vinyl sulfonamide and formaldehyde.
BE613866A BE613866A (en) 1961-02-16 1962-02-13 Process for the production of condensation products from vinylsulfamide and formaldehyde
GB578362A GB951887A (en) 1961-02-16 1962-02-15 Production of condensation products of vinylsulphonamide and formaldehyde

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1961B0061293 DE1178071B (en) 1961-02-16 1961-02-16 Process for the preparation of a heterocyclic condensation product from vinyl sulfonamide and formaldehyde.

Publications (1)

Publication Number Publication Date
DE1178071B true DE1178071B (en) 1964-09-17

Family

ID=6973148

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1961B0061293 Pending DE1178071B (en) 1961-02-16 1961-02-16 Process for the preparation of a heterocyclic condensation product from vinyl sulfonamide and formaldehyde.

Country Status (3)

Country Link
BE (1) BE613866A (en)
DE (1) DE1178071B (en)
GB (1) GB951887A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3470177A (en) * 1964-07-16 1969-09-30 Albert Ag Chem Werke Hexahydrotriazine derivative

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3470177A (en) * 1964-07-16 1969-09-30 Albert Ag Chem Werke Hexahydrotriazine derivative

Also Published As

Publication number Publication date
GB951887A (en) 1964-03-11
BE613866A (en) 1962-08-13

Similar Documents

Publication Publication Date Title
DE1180372B (en) Process for the preparation of 2,6-dioxopiperazines
DE1178071B (en) Process for the preparation of a heterocyclic condensation product from vinyl sulfonamide and formaldehyde.
DE2429935B2 (en) Process for the preparation of 2,2,6,6-tetramethyl-4-oxopiperidine
DE2049160C3 (en) Process for the preparation of 4,4-dimethyl-5,6-dihydro-13-oxazines
US2778821A (en) Production of compounds of the pyrimidine series
DE1158083B (en) Process for the preparation of basic substituted phenylacetonitriles
DE889157C (en) Process for the preparation of amide-type condensation compounds
DE165561C (en)
DE1205975B (en) Process for the preparation of bases of the diphenylmethane series
DE947610C (en) Process for the preparation of benzimidazoines
DE1000820C2 (en) Process for the preparation of iminodibenzylene
DE909809C (en) Process for the preparation of carboxylic acids containing at least two cyano groups
DE1087594C2 (en) Process for the production of new nitrogen-containing epoxy compounds
AT287710B (en) Process for the preparation of substituted 3-amino-sydnonimines and their salts
DE848043C (en) Process for the preparation of formyl compounds of 2,6-dioxy-4,5-diaminopyrimidine and its methyl derivatives
US2390476A (en) Sulphoaliphatic guanamines
DE1228613B (en) Process for the preparation of 2 ', 6'-disubstituted N-alkylpiperidine-2-monocarboxylic acid anilides
DE810394C (en) Process for the preparation of camphane-2-spiro-hydantoin
DE2010124C (en) Process for the preparation of 2 6 dimethyl 3 amino 6 (beta cyanoathyl) cyclo hexen (2) one
DE819403C (en) Process for the production of cystathionine
DE1795586C3 (en) Process for the preparation of 2,4-diamino-5-benzyl-pyrimidines
DE1806207A1 (en) Water-soluble polyamides
DE964495C (en) Process for the preparation of a new thiosemicarbazide
DE963331C (en) Process for the preparation of p-tolylic acid
DE3515402A1 (en) Process for the stabilisation of concentrated liquid resinous tanning agent solutions