DE1097980B - Process for the preparation of organic sulfohalides - Google Patents
Process for the preparation of organic sulfohalidesInfo
- Publication number
- DE1097980B DE1097980B DEH37459A DEH0037459A DE1097980B DE 1097980 B DE1097980 B DE 1097980B DE H37459 A DEH37459 A DE H37459A DE H0037459 A DEH0037459 A DE H0037459A DE 1097980 B DE1097980 B DE 1097980B
- Authority
- DE
- Germany
- Prior art keywords
- sulfochloride
- sulfohalides
- organic
- salts
- isolated
- 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 6
- 238000002360 preparation method Methods 0.000 title description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- WDTBNUITWIDXGJ-UHFFFAOYSA-N 1-chloroprop-1-ene sulfurochloridic acid Chemical compound S(=O)(=O)(O)Cl.ClC=CC WDTBNUITWIDXGJ-UHFFFAOYSA-N 0.000 claims description 4
- XSVKYWGBTGTFLB-UHFFFAOYSA-N 3-hydroxypropane-1,2-disulfonic acid Chemical compound OCC(S(O)(=O)=O)CS(O)(=O)=O XSVKYWGBTGTFLB-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- -1 hydroxyl-substituted carbon atom Chemical group 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- YWHDQEMPDCYNQK-UHFFFAOYSA-N 2,2-dichloropropane sulfurochloridic acid Chemical compound S(=O)(=O)(O)Cl.ClC(C)(C)Cl YWHDQEMPDCYNQK-UHFFFAOYSA-N 0.000 description 1
- WQPMYSHJKXVTME-UHFFFAOYSA-N 3-hydroxypropane-1-sulfonic acid Chemical compound OCCCS(O)(=O)=O WQPMYSHJKXVTME-UHFFFAOYSA-N 0.000 description 1
- DULLVYDQXNKDMS-UHFFFAOYSA-N C(Cl)(Cl)(Cl)Cl.ClS(=O)(=O)O Chemical compound C(Cl)(Cl)(Cl)Cl.ClS(=O)(=O)O DULLVYDQXNKDMS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- DUVWEDHMBXACAE-UHFFFAOYSA-N S(=O)(=O)(O)Cl.ClCCC Chemical compound S(=O)(=O)(O)Cl.ClCCC DUVWEDHMBXACAE-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical class ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000008053 sultones Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von organischen Sulfohalogeniden Es wurde gefunden, daß man durch Einwirkung von Phosphorpentachlorid auf 1 -Hydroxypropan-2,3-disulfonsäure oder deren Salze zu neuartigen Sulfochloriden gelangt, die auf Grund ihrer eigenartigen Konstitution besondere wertvolle Eigenschaften besitzen, welche sie für die Durchführung chemischer Umsetzungen mannigfacher Art geeignet machen. Das erfindungsgemäße Verfahren wird in der Weise durchgeführt, daß man die Disulfonsäure in Form eines Salzes, z. B. des ohne Kristallwasser kristallisierenden Kaliumsalzes, mit Phosphorpentachlorid innig vermischt und mehrere Stunden auf dem Wasserbad erhitzt. Dabei entstehen Gemische, die hauptsächlich Sulfochloride nachstehender Zusammensetzung enthalten: 1,3-Propansulton-2-sulfochlorid der Formel sowie Chlorpropensulfochlorid der Formel neben geringen Mengen von 1,2-Dichlorpropan-3- bzw.Process for the preparation of organic sulphohalides It has been found that the action of phosphorus pentachloride on 1-hydroxypropane-2,3-disulphonic acid or its salts leads to novel sulphochlorides which, due to their peculiar constitution, have particularly valuable properties which they use for implementation make chemical reactions of various kinds suitable. The inventive method is carried out in such a way that the disulfonic acid in the form of a salt, for. B. the potassium salt which crystallizes without water of crystallization, intimately mixed with phosphorus pentachloride and heated for several hours on a water bath. This results in mixtures which mainly contain sulfochlorides with the following composition: 1,3-propanesultone-2-sulfochloride of the formula as well as chloropropene sulfochloride of the formula in addition to small amounts of 1,2-dichloropropane-3- or
1,3-Dichlorpropan-2-sulfochlorid. Aus diesen Gemischen lassen sich die oben bezeichneten Sulfochloride isolieren.1,3-dichloropropane-2-sulfochloride. From these mixtures isolate the sulfochlorides identified above.
Das 1,3-Propansulton-2-sulfochlorid ist ein fester kristallisierender Körper, das 1-Chlorpropensulfochlorid eine ölige Flüssigkeit. Beide Verbindungen zeichnen sich durch hohe Reaktionsfähigkeit aus und gestatten im Hinblick auf ihre bifunktionellen Eigenschaften die stufenweise Durchführung von Umsetzungsreaktionen mannigfacher Art. The 1,3-propanesultone-2-sulfochloride is a solid crystallizing one Body, the 1-chloropropene sulfochloride is an oily liquid. Both connections are characterized by high responsiveness and allow in terms of their bifunctional properties the gradual implementation of conversion reactions of various kinds.
Es ist bekannt, daß 1-Hydroxypropan-3-sulfonsäure in Form ihrer Salze mit Phosphorpentachlorid unter Bildung des 1-Chlorpropan-3-sulfochlorids reagiert (vgl. It is known that 1-hydroxypropane-3-sulfonic acid in the form of its salts reacts with phosphorus pentachloride to form 1-chloropropane-3-sulfochloride (see.
M. S. Kharasch, E. M. May und F. R. Mayo, Journal of organic Chemistry, Bd. 3 [1939], S. 175 ff.). Im Fall der 1-Hydroxypropan-2,3-Disulfonsäure wäre die Bildung des 1-Chlorpropan-2,3-disulfochlorids zu erwarten gewesen. Der tatsächliche Reaktionsverlauf, der statt dessen zu den oben angegebenen Monosulfochloriden führt, war überraschend und neuartig. Insbesondere konnte die Ausbildung eines Sultonringes und damit das Entstehen einer Verbindung, die zwei funktionell verschiedenartige Gruppen besitzt, in keiner Weise vorhergesehen werden. Produkte dieser Art waren unbekannt, sie ermöglichen Umsetzungsreaktionen, die man bisher nicht ausführen konnte. Abgesehen davon, daß diese Produkte eine stufenweise Umsetzung mit organischen Verbin- dungen gestatten, die austauschbare Wasserstoffatome an Kohlenstoff oder auch über Sauerstoff, Schwefel oder Stickstoff gebunden enthalten, kann man sie auch auf natürliche oder synthetische Produkte zur Erzielung besonderer Veredlungseigenschaften, beispielsweise zur Erhöhung der Hydrophylie, einwirken lassen.M. S. Kharasch, E. M. May and F. R. Mayo, Journal of organic Chemistry, Vol. 3 [1939], pp. 175 ff.). In the case of 1-hydroxypropane-2,3-disulfonic acid this would be Formation of 1-chloropropane-2,3-disulfochloride was to be expected. The real one Course of the reaction, which instead leads to the monosulphochlorides given above, was surprising and novel. In particular, the training of a sulton ring and with it the creation of a connection, the two functionally different Groups owns are in no way foreseen. Products of this type were unknown, they enable conversion reactions that have not yet been carried out could. Apart from the fact that these products have a gradual reaction with organic Connecting Allow the interchangeable hydrogen atoms on carbon or they can also be bound via oxygen, sulfur or nitrogen also on natural or synthetic products to achieve special finishing properties, for example to increase the hydrophyly, leave to act.
Das Verfahren ist nicht auf die Verwendung von 1 Hydroxypropandisulfonsäure-(2,3) oder deren Salze als Ausgangsstoffe beschränkt, sondern man kann auch andere Hydroxyalkandisulfonsäuren verwenden. An Stelle des Phosphorpentachlorids sind auch andere halogenierend wirkende Mittel verwendbar, z. B. Phosphorpentabromid. The procedure is not limited to the use of 1 hydroxypropanedisulfonic acid- (2,3) or their salts are limited as starting materials, but other hydroxyalkanedisulfonic acids can also be used use. Instead of phosphorus pentachloride there are also other halogenating agents Means can be used, e.g. B. phosphorus pentabromide.
Beispiel a) 74 Gewichtsteile trocknes, feinpulverisiertes l-hydroxypropan-2,3-disulfonsaures Kalium werden mit 170 Gewichtsteilen Phosphorpentachlorid innig vermischt und dann auf 90 bis 110"C unter Rückfluß erhitzt. Example a) 74 parts by weight of dry, finely powdered l-hydroxypropane-2,3-disulfonic acid Potassium are intimately mixed with 170 parts by weight of phosphorus pentachloride and then heated to 90 to 110 "C under reflux.
Die Reaktion setzt allmählich ein; das Reaktionsgemisch verflüssigt sich, und Chlorwasserstoff wird entbunden.The reaction begins gradually; the reaction mixture liquefies and hydrogen chloride is released.
Nach 4 bis 6 Stunden ist die Reaktion beendet, kenntlich daran, daß eine nur noch wenig feste Bestandteile (Natriumchlorid) enthaltende, kaum gefärbte Flüssigkeit entstanden ist und praktisch kein Chlorwasserstoff mehr entwickelt wird. Zur Aufarbeitung wird das entstandene Phosphoroxychlorid abdestilliert, zweckmäßig unter vermindertem Druck; der Destillationsrückstand wird mit 50 bis 100 Volumteilen Tetrachlorkohlenstoff aufgenommen und unter Rühren mit Eiswasser versetzt, Jo daß die Temperatur 100 C nicht übersteigt. Hierbei erfolgt Hydrolyse noch vorhandener geringer Mengen an Phosphorchloriden und Lösung des Natriumchlorids; gleichzeitig scheidet sich ein weißes feinkristallisiertes, sowohl in Wasser als auch in Tetrachlorkohlenstoff unlösliches Produkt ab, das durch Absaugen und Waschen mit Tetrachlorkohlenstoff von den flüssigen Sulfochloriden befreit wird. Das Produkt stellt das 1,3-Propansulton-2-sulfochlorid dar und wird in einer Ausbeute von 20 Gewichtsteilen, entsprechend 36°/o der Theorie, mit bereits guter Reinheit erhalten.After 4 to 6 hours, the reaction has ended, indicated by the fact that one that contains only a few solid components (sodium chloride) and is hardly colored Liquid has formed and practically no more hydrogen chloride is evolved. For work-up, the phosphorus oxychloride formed is distilled off, expediently under reduced pressure; the distillation residue is 50 to 100 parts by volume Carbon tetrachloride was added and ice water was added while stirring, Jo that the temperature does not exceed 100 C. Here hydrolysis takes place even more present small amounts of phosphorus chlorides and solution of sodium chloride; simultaneously a white finely crystallized precipitate, both in water and in carbon tetrachloride insoluble product removed by suction and washing with carbon tetrachloride of the liquid sulfochlorides is released. The product represents the 1,3-propanesultone-2-sulfochloride and is in a yield of 20 parts by weight, according to 36% of the theory, obtained with already good purity.
Durch Umkristallisieren aus Tetrachlorkohlenstoff erhält man das Sulfochlorid leicht in sehr reiner Form; es bildet lange weiße, ineinander verfilzte Kristallnadeln vom F. = 109 bis 111"C. Die Löslichkeit in den gebräuchlichen organischen Lösungsmitteln ist vor allem in der Kälte nur gering. Gegen kaltes Wasser ist es relativ stabil, wird aber in der Wärme rasch hydrolysiert, wobei erst der Sultonring aufgespalten und dann in zweiter Reaktionsstufe die Sulfochloridgruppe verseift wird. This is obtained by recrystallization from carbon tetrachloride Sulfochloride easily in very pure form; it forms long white, matted together Crystal needles from F. = 109 to 111 "C. The solubility in the common organic Solvents is low, especially in the cold. It is against cold water relatively stable, but is rapidly hydrolysed when heated, with the sultone ring first split and then saponified the sulfochloride group in the second reaction stage will.
Die Analyse des Produktes C3H5O5S2Cl ergab: Berechnet C 16,33, H 2,27, S29,07, Cl 16,10o/o; gefunden C 16,03, H 2,42, S29,18, C116,27°lo. b) Die gemäß Abschnitt a) nach Abtrennung des Propansulton-2-sulfochlorids zurückbleibende gelblichgefärbte, stechend riechende Tetrachlorkohlenstofflösung wird nach dem Trocknen über Natriumsulfat unter vermindertem Druck vom Lösungsmittel befreit und anschließend bei einem Druck von 12 Torr destilliert. The analysis of the product C3H5O5S2Cl resulted in: Calculated C 16.33, H 2.27, S29.07, Cl 16.10o / o; Found C 16.03, H 2.42, S29.18, C 116.27 ° Lo. b) The according to section a) after separation of the propanesultone-2-sulfochloride remaining yellowish colored, pungent smelling carbon tetrachloride solution becomes after drying freed from the solvent over sodium sulfate under reduced pressure and then distilled at a pressure of 12 torr.
Man erhält dabei zwei Fraktionen, deren untere bei Kr.12 = 85 bis 90"C und deren obere bei Kp.12 = 115 bis 120"C übergeht. Bei der niedrigersiedenden Fraktion, die in einer Ausbeute von etwa 400/, der Theorie anfällt, handelt es sich um Chlorpropensulfochlorid, das thermisch verhältnismäßig sehr stabil ist und bei Normaldruck unzersetzt bei 180 bis 183"C destilliert. Die reine Ver- bindung ist farblos und stellt eine stechend riechende und zu Tränen reizende Flüssigkeit dar.Two fractions are obtained, the lower one at Kr.12 = 85 bis 90 "C and its upper transition at Kp.12 = 115 to 120" C. At the lower boiling point Fraction, which is obtained in a yield of about 400 /, of theory, it is to chloropropene sulfochloride, which is relatively thermally stable and at Normal pressure distilled undecomposed at 180 to 183 "C. The pure ver bond is colorless and is a pungent smelling liquid that irritates tears.
Die Analyse des Produktes C3H4CaSCl2 ergab: Berechnet C 20,57, H 2,28, S 18,32, Cl 40,520/v; gefunden C 20,70, H 2,45, S 18,42, C1 40,89 O/o. The analysis of the product C3H4CaSCl2 gave: Calculated C 20.57, H 2.28, S 18.32, Cl 40.520 / v; found C 20.70, H 2.45, S 18.42, C1 40.89 O / o.
Die höhersiedende Fraktion konnte als Dichlorpropansulfochlorid identifiziert werden; sie ist thermisch instabil und geht bei der Destillation unter Normaldruck in Chlorpropansulfochlorid und 1,2,3-Trichlorpropan über. The higher-boiling fraction was identified as dichloropropane sulfochloride will; it is thermally unstable and is distilled under normal pressure in chloropropane sulfochloride and 1,2,3-trichloropropane.
Claims (2)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH37459A DE1097980B (en) | 1959-09-17 | 1959-09-17 | Process for the preparation of organic sulfohalides |
| GB31274/60A GB892788A (en) | 1959-09-17 | 1960-09-12 | Process for the preparation of organic sulphohalides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH37459A DE1097980B (en) | 1959-09-17 | 1959-09-17 | Process for the preparation of organic sulfohalides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1097980B true DE1097980B (en) | 1961-01-26 |
Family
ID=7153329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH37459A Pending DE1097980B (en) | 1959-09-17 | 1959-09-17 | Process for the preparation of organic sulfohalides |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1097980B (en) |
| GB (1) | GB892788A (en) |
-
1959
- 1959-09-17 DE DEH37459A patent/DE1097980B/en active Pending
-
1960
- 1960-09-12 GB GB31274/60A patent/GB892788A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB892788A (en) | 1962-03-28 |
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