DE735096C - Process for the production of sulphonic acids - Google Patents
Process for the production of sulphonic acidsInfo
- Publication number
- DE735096C DE735096C DEI68390D DEI0068390D DE735096C DE 735096 C DE735096 C DE 735096C DE I68390 D DEI68390 D DE I68390D DE I0068390 D DEI0068390 D DE I0068390D DE 735096 C DE735096 C DE 735096C
- Authority
- DE
- Germany
- Prior art keywords
- hydrocarbons
- sulfur dioxide
- production
- acids
- oil
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 title description 8
- 150000007513 acids Chemical class 0.000 title description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 150000003460 sulfonic acids Chemical class 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 description 15
- 150000002430 hydrocarbons Chemical class 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- -1 hydrocarbons salts Chemical class 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- FKOZPUORKCHONH-UHFFFAOYSA-N 2-methylpropane-1-sulfonic acid Chemical compound CC(C)CS(O)(=O)=O FKOZPUORKCHONH-UHFFFAOYSA-N 0.000 description 1
- RUOIPBUNBYUZCK-UHFFFAOYSA-N 2-methylpropane-1-sulfonic acid;sodium Chemical compound [Na].CC(C)CS(O)(=O)=O RUOIPBUNBYUZCK-UHFFFAOYSA-N 0.000 description 1
- YDOBHSAXRNUOFX-UHFFFAOYSA-N 3-ethylheptane-1-sulfonic acid Chemical class CCCCC(CC)CCS(O)(=O)=O YDOBHSAXRNUOFX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical class CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing 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
- C07C303/14—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 by sulfoxidation, i.e. by reaction with sulfur dioxide and oxygen with formation of sulfo or halosulfonyl groups
-
- 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
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
- C23C14/04—Coating on selected surface areas, e.g. using masks
-
- G—PHYSICS
- G04—HOROLOGY
- G04B—MECHANICALLY-DRIVEN CLOCKS OR WATCHES; MECHANICAL PARTS OF CLOCKS OR WATCHES IN GENERAL; TIME PIECES USING THE POSITION OF THE SUN, MOON OR STARS
- G04B37/00—Cases
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G4/00—Fixed capacitors; Processes of their manufacture
- H01G4/28—Tubular capacitors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G4/00—Fixed capacitors; Processes of their manufacture
- H01G4/30—Stacked capacitors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G5/00—Capacitors in which the capacitance is varied by mechanical means, e.g. by turning a shaft; Processes of their manufacture
- H01G5/38—Multiple capacitors, e.g. ganged
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
-
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03J—TUNING RESONANT CIRCUITS; SELECTING RESONANT CIRCUITS
- H03J3/00—Continuous tuning
- H03J3/20—Continuous tuning of single resonant circuit by varying inductance only or capacitance only
Landscapes
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing & Machinery (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Sulfonsäuren
Die bei dein vorliegenden '-erfahren entstehenden Sulfonsä Uren scheiden sich bei Verwendung von niederen Kohlenwasserstoften zum größten Teil als Üle ab und können durch Trennung in Scheidegefäßen in roher Form gewonnen werden. Bei '#,-erwendung von höheren Kohlenwasserstoffeil bleiben die Sulfonsäuren zum Teil in diesen gelöst; sie können dann durch Extraktion mit in Kohlen-#.%-asserstofen unlöslichen Lösungsmitteln, wie z. B. Wasser oder 1lethylalkohol. abgetrennt «-erden. Durch Einengen der Extrakte erhält man die Sulfonsäuren in konzentrierter Form. Durch Neutralisation z. B. init Alkalien und gegebenenfalls Abtrennung der nicht umgesetzten Kohlenwasserstoffe nach bekannten Zerfahren erhält man Salze. Im allgemeinen entstehen vorwiegend Salze von 1lonosulfonsäuren im Gemisch finit Salzen von Disulfonsäuren und Alkalisulfaten.The sulphonic acids that arise during your present experience separate when lower hydrocarbons are used, for the most part turn out to be oils and can be obtained in raw form by separation in separating vessels. When using '#, the sulfonic acids of the higher hydrocarbons remain partially dissolved in them; they can then be extracted with solvents that are insoluble in coal - #.% - such as B. water or 1lethyl alcohol. separated «-earth. By concentrating the extracts the sulfonic acids are obtained in concentrated form. By neutralization z. B. init Alkalis and optionally separation of the unreacted hydrocarbons salts are obtained by known methods. In general, mainly salts are formed of llonosulphonic acids in a mixture of finite salts of disulphonic acids and alkali sulphates.
Die nach dein vorliegenden Verfahren erhältlichen Stoffe finden technisch vielseitig Verwendung, die höhermolekularen besonders als kapillaraktiv e'Mittel.The substances obtainable according to your present process can be found technically versatile use, the higher molecular weight especially as capillary-active e'mittel.
Gegenfiber dem bekannten Verfahren, hohlenwasserstoffe mit Schwefeldioxyd
und Chlor gegebenenfalls unter Belichtung zu Schwefel, Sauerstoff und Chlor enthaltenden
1'erbindungen, im wesentlichen Sulfochloriden, umzusetzen, bietet das vorliegende
Verfahren den Vorteil, daß man unmittelbar zu den freien Sulfonsäuren gelangt und
daß man ohne stark korrodierend wirkende Stoffe, wie Chlor und Chlorwasserstoff,
arbeiten kann. Beispiele
Das abgeschiedene Ü1 enthält in der Hauptsache Cvclolietansulfonsiiure und etwas Schwefelsäure: an feuchter Luft kristallisiert daraus ein Hydrat der C@'cloliexan--tilfotisatirL!. das durch Absaugen in reiner 1#orin gewonn_il werden kann. Zur Aufarbeitung trägt nian das Öl zweckmäßig in %fasser ein, entfernt durch 1?inblasen von Dampf Cyclohexan, Schwefeldioxyd und flüchtige Zer:etzungsprodukte und neutralisiert dann finit Natronlauge. Dampft man die Lösung zur Trockne. so erhält inan ein Pulver, das etlva qo °,'° cvclohexansulfonsaures -Natrium neben io °,,° Natriumsulfat enthält. Durch Unikristallisieren aus Wasser erhält man das evc1ohexansulfonsaure Natrium in glänzenden Blättchen.The separated oil contains mainly Cvclolietansulfonsiiure and a little sulfuric acid: in moist air a hydrate of C @ 'cloliexan - tilfotisatirL! crystallizes from it. that can be obtained by suction in pure 1 # orin. To work up contributes nian the oil expediently in a volume of water, removed by blowing in steam cyclohexane, Sulfur dioxide and volatile decomposition products and then finitely neutralizes sodium hydroxide solution. The solution is evaporated to dryness. so inan receives a powder that is etlva qo °, '° contains cvclohexansulfonsaures -sodium in addition to io ° ,, ° sodium sulfate. By unicrystallizing the evc1ohexanesulphonic acid sodium is obtained in shiny flakes from water.
Gti ähnlichen Ergebnissen gelangt -man, wenn man die Umsetzungen in violgl is-oder Quarzapparaturen durchführt. Hier kommt die Umsetzung, wenn auch langsamer, schon durch Bestrahlung mit einer hochkerzigen Glühlampe in Gang. -Man kann die Herstellung der Cyclohexansulfonsäure aus Cyclohexan, Schwefeldioxyd und `auerstolz auch so durchführen, daß inan die Unisetzung, wie oben beschrieben, durch Bestrahlung in Gang bringt und nach beginnender Ülabscheidung die Lichtquelle ausschaltet. Die Umsetzung läuft ohne Störung im Dunkeln weiter, wobei man praktisch die gleichen Ausbeuten wie bei dauerndem Bestrahlen erhält.Gti similar results can be obtained if one looks at the conversions in violgl is or quartz apparatus carries out. Here comes the implementation, albeit slower, already started by irradiation with a high-candlestick incandescent lamp. -Man can produce cyclohexanesulfonic acid from cyclohexane, sulfur dioxide and `` Perform with pride in such a way that inan the unisposition, as described above, through Bringing irradiation in motion and switching off the light source after the beginning of the deposition of oil. The implementation continues in the dark without any disturbance, practically the same Yields as obtained with continuous irradiation.
2. Ersetzt man im Beispiel r das Cyclohexan durch n-Heptan, so ist-das äußere Bild der 'Unisetzung das gleiche: auch hier läuft die einmal eingeleitete Umsetzung im Dunkeln glatt weiter. Durch Eintragen in Wasser und Behandlung mit Dampf erhält nian eine Lösung, die nach der -Neutralisation finit -Natronlauge und Ein(latnpfen ein halbfest. l'rzetir,ni: ergibt. (las au: einem Gemisch von etwa 8; bis 90 °,'° \Tatriumsalzen von hauptsächlich Heptanniono- und etwas Di:ulfon-#äuren mit 13 bis 1o °`° Natriumsulfat besteht.2. If the cyclohexane is replaced by n-heptane in example r, the external picture of the dissolution is the same: here too, once the conversion has been initiated, it continues smoothly in the dark. By immersing it in water and treating it with steam, a solution is obtained which, after neutralization, finite sodium hydroxide solution and a (latnpfen, results in a semi-solid. L'rzetir, ni:. It consists of sodium salts of mainly heptannionic and some di: ulfonic acids with 13 to 10 ° sodium sulfate.
3. Ersetzt man im Beispiel r (las Cyclollexan (lurch 1letliylcycloliexan. So erhält inan nach (ler Umarbeitung auf die Natriuni:alze ein halbfestes Erzeugnis. in deni eine Mischung Voll etwa 75 bis So'"', der Natriunisalze %-on lIetlivlcvclohexaninoliostilfonsä Uren neben etwas Disultonsauren mit 25 bi: 2o °/o Natriumsulfat vorliegt.. 3. Replacing So obtained in Example r (las Cyclollexan (lurch 1letliylcycloliexan inan by (ler makeover on the Natriuni: Alze a semi-solid product in a mixture full deni about 75 to So ''', the Natriunisalze% -one lIetlivlcvclohexaninoliostilfonsä Uren. in addition to some disultonic acid with 25 bi: 20% sodium sulphate.
In eineng Apparat ähnlich dein in Beispiel i beschriebenen, der mit 8oo Gewichtsteilen Tetrachlorkohlenstoff gefüllt ist, leitet man stündlich ein Gasgemisch von 2o I n-Butan, io 1 Schwefeldioxyd und 3 1 Sauerstoff ein und belichtet mit einer Quecksilberdampfquarzlainpe. 'Nach kurzer Zeit trübt sich der Tetrachlorkohlenstoff und scheidet ein farbloses Öl ab, das spezifisch leichter als das Lösungsmittel ist. 1Iai-1 erhält je Stunde etwa 16 Gewichtsteile Öl.In an apparatus similar to that described in example i, the one with 800 parts by weight of carbon tetrachloride is filled, a gas mixture is passed every hour of 2o I n-butane, 10 1 sulfur dioxide and 3 1 oxygen and exposed to a Mercury vapor quartz glass. 'After a short time, the carbon tetrachloride becomes cloudy and separates out a colorless oil that is specifically lighter than the solvent is. 1Iai-1 receives about 16 parts by weight of oil per hour.
Die obere Ölschicht wird, wie im Beispiel i beschrieben, aufgearbeitet und liefert ein Gemisch Von etwa S; °i, L\Tatriumsalzen der n-Butansulfonsäuren und 13 °,lo Natriumsulfat.The upper oil layer is worked up as described in Example i and provides a mixture of about S; ° i, sodium salts of n-butanesulfonic acids and 13 °, lo sodium sulfate.
Verwendet man statt n-Butans Isobutan, so Verläuft die Reaktion etwas langsamer, das anfallende Öl erstarrt an feuchter Luft zu dem kristallinen Hvdrat einer Isobutansulfonsäure. Nach der Aufarbeitung erhält man ein Gemisch Voll etwa ;7 °@p isobutansulfonsaurem Natriulli und 23 °/o \Tatriumsulfat.If isobutane is used instead of n-butane, the reaction proceeds somewhat slower, the resulting oil solidifies in moist air to form the crystalline substrate an isobutanesulfonic acid. After the work-up, a mixture of approximately full is obtained ; 7% p isobutanesulphonic acid sodium and 23% sodium sulphate.
Verwendet man -an Stelle von n-Butan Propan, so gelangt inan zu ähnlichen Ergebnissen, die Umsetzung Verläuft hier nur langsamer als beim Butan. Statt Tetrachlorkohlenstoffes kann man äuch.andere geeignete Lösungsmittel, wie z.B. 1Ictliylenclilorid, mit gleichem Erfolg anwenden.If propane is used instead of n-butane, similar ones are obtained Results, the implementation is only slower here than with butane. Instead of carbon tetrachloride you can also use other suitable solvents, such as octylene chloride, with the same Apply success.
Ersetzt man im Beispiel i das Cyclohexan durch 3-llethyllieptan, so sind die äußeren Erscheinungen der Umsetzung, die nur wesentlich langsamer Verläuft, ganz ähnliche.' Nach der Aufarbeitung erhält man ein Salzgemisch Von etwa 86 bis SS °r, Natriumsalzen von 3-1lethvlheptansulfonsäuren mit 14 bis I20/0 Natriumsulfat.If in example i the cyclohexane is replaced by 3-llethyllieptane, so are the outward appearances of the implementation, which only proceeds much more slowly, very similar. ' After working up, a salt mixture from about 86 to is obtained SS ° r, sodium salts of 3-1 ethyl heptanesulfonic acids with 14 to 120/0 sodium sulfate.
6. Ersetzt man im Beispiel i das Cyclohexan durch ein Gemisch, das durch Hy drin rung einer Voll 2=o bis 32o° siedenden Fraktion des durch Unisetzung Von Kohlenoxyd mit Wasserstoff erhältlichen Kohlenwasserstoffgemisches gewonnen wird, und behandelt unter Bestrahlung mit einer Quecksilberdampf lampe mit einem Gemisch Von SChwefeldioxyd und Sauerstoff, so beobachtet man eine rasch zunehmende Gelbfärbung des Kohlenwasserstoffgemisches bei gleichzeitiger Ölabscheidung. Durch Extraktion mit wäßrigeni Methylalkohol gewinnt man eine Lösung, die nach Entfernung des Schwefeldioxyds und der angewandten Lösungsmittel neutralisiert und zur Trockne gedampft wird. "Man erhält so ein Genfisch Von 'N atriumsalzen der Sulfonsäuren der angewandten Kohlenwasserstoffe mit Natriumsulfat.6. If in example i the cyclohexane is replaced by a mixture which by hy drin tion of a full 2 = 0 to 32o ° boiling fraction of the by unisposition Obtained from carbon dioxide with hydrogen obtained hydrocarbon mixture is, and treated under irradiation with a mercury vapor lamp with a The mixture of sulfur dioxide and oxygen is observed to increase rapidly Yellowing of the hydrocarbon mixture with simultaneous oil separation. By Extraction with aqueous methyl alcohol gives a solution which, after removal of sulfur dioxide and the solvents used, neutralized and dried is steamed. "You get a gene table of sodium salts of sulfonic acids of the applied hydrocarbons with sodium sulphate.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI0068390 | 1940-12-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE735096C true DE735096C (en) | 1943-05-06 |
Family
ID=7196871
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEI68390D Expired DE735096C (en) | 1940-12-09 | 1940-12-10 | Process for the production of sulphonic acids |
Country Status (4)
Country | Link |
---|---|
BE (8) | BE443658A (en) |
CH (1) | CH228209A (en) |
DE (1) | DE735096C (en) |
FR (1) | FR877672A (en) |
Cited By (53)
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US2503280A (en) * | 1947-10-24 | 1950-04-11 | Du Pont | Azo catalysts in preparation of sulfonic acids |
US2507088A (en) * | 1948-01-08 | 1950-05-09 | Du Pont | Sulfoxidation process |
DE1014067B (en) * | 1953-07-29 | 1957-08-22 | Basf Ag | Wetting agent for mercerising and caustic baths |
DE967238C (en) * | 1953-02-06 | 1957-10-24 | Basf Ag | Easily emulsifiable or colloidally soluble wax products |
DE1139116B (en) * | 1956-02-03 | 1962-11-08 | Exxon Research Engineering Co | Process for the preparation of aliphatic and cycloaliphatic sulfonic acids |
US3507909A (en) * | 1968-01-22 | 1970-04-21 | Phillips Petroleum Co | Production of sulfonate salts of lighter color |
US4518537A (en) * | 1983-02-07 | 1985-05-21 | Hoechst Aktiengesellschaft | Process for isolating paraffinsulfonate from the reaction mixture obtained on sulfoxidating paraffins |
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Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE910165C (en) * | 1943-01-15 | 1954-04-29 | Hoechst Ag | Process for the production of sulphonic acids |
DE872942C (en) * | 1948-10-02 | 1953-04-09 | Krupp Kohlechemie G M B H | Process for the sulfoxidation of oxygen-containing derivatives of saturated aliphatic or cycloaliphatic hydrocarbons |
-
1940
- 1940-12-10 DE DEI68390D patent/DE735096C/en not_active Expired
-
1941
- 1941-11-15 CH CH228209D patent/CH228209A/en unknown
- 1941-12-09 BE BE443658A patent/BE443658A/en unknown
- 1941-12-11 FR FR877672D patent/FR877672A/en not_active Expired
-
1942
- 1942-02-09 BE BE444546A patent/BE444546R/en active
- 1942-04-23 BE BE445312A patent/BE445312R/en active
- 1942-04-27 BE BE445349A patent/BE445349R/en active
-
1943
- 1943-04-09 BE BE450081A patent/BE450081R/en active
-
1944
- 1944-08-17 BE BE457247A patent/BE457247R/en active
- 1944-08-17 BE BE457246A patent/BE457246R/en active
-
1959
- 1959-03-28 BE BE457245A patent/BE457245R/en active
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Also Published As
Publication number | Publication date |
---|---|
BE445349R (en) | 1942-05-30 |
CH228209A (en) | 1943-08-15 |
BE457246R (en) | 1944-09-30 |
BE443658A (en) | 1942-01-31 |
BE450081R (en) | 1943-05-31 |
FR877672A (en) | 1942-12-14 |
BE445312R (en) | 1942-05-30 |
BE457247R (en) | 1944-09-30 |
BE457245R (en) | 1944-09-30 |
BE444546R (en) | 1942-03-31 |
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