DE681338C - Process for the production of sulfonic acid salts - Google Patents
Process for the production of sulfonic acid saltsInfo
- Publication number
- DE681338C DE681338C DEI51249D DEI0051249D DE681338C DE 681338 C DE681338 C DE 681338C DE I51249 D DEI51249 D DE I51249D DE I0051249 D DEI0051249 D DE I0051249D DE 681338 C DE681338 C DE 681338C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- acid salts
- production
- water
- vinyl
- 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
- 150000003460 sulfonic acids Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical class C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- -1 aliphatic vinyl sulfones Chemical class 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- HTAMRUHHHVQRON-UHFFFAOYSA-N 1-ethenylsulfonyldodecane Chemical compound CCCCCCCCCCCCS(=O)(=O)C=C HTAMRUHHHVQRON-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-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
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- LVGQIQHJMRUCRM-UHFFFAOYSA-L calcium bisulfite Chemical compound [Ca+2].OS([O-])=O.OS([O-])=O LVGQIQHJMRUCRM-UHFFFAOYSA-L 0.000 description 1
- 235000010260 calcium hydrogen sulphite Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide 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 sulfonsaurer Salze Es wurde gefunden, daß man wertvolle sulfonsaure Salze erhält, wenn man Viny1sulfone der allgemeinen Formel R (S02 # CH= CH2)" in der R einen: höhermolekularen aliphatischen Rest und x eine ganze Zahl bedeutet, mit Bisulfiten der Leichtmetalle der i. und 2. Gruppe des periodischen Systems umsetzt.Process for the preparation of sulfonic acid salts It has been found that Valuable sulfonic acid salts are obtained if vinyl sulfones of the general formula are used R (S02 # CH = CH2) "in which R one: higher molecular weight aliphatic radical and x one Whole number means with bisulfites of the light metals of the i. and 2nd group of the periodic Systems implements.
Von höheiznolekularen aliphatischen Vinylsulfonen, die für die Umsetzung in Betracht kommen, seien beispielsweise 1-1eptyl-, Dodecyl-, Octod-ecyl- und Oleylvinylsulfone erGvähnt. Vinylsulfone, die die Vinylsulfongruppe mehrfach im Molekül enthalten, z. B. i, i2-Divi:nylsulfonoctodecan,können sich entsprechend oft umsetzen. Die Vinylalkylsulfone können auch verzweigte Ketten aufweisen und noch andere Atome oder Atomgruppen, z. B. Halogenatome oder Hydroxyl-, Alkoxy-, Oxalkyl-, Nitro-, Amino-, Sulfhydryl-, Ca,rboxyl- oder Sulfansäuregruppen enthalten.From Höheiznolekularen aliphatic vinyl sulfones, which are necessary for the implementation come into consideration are, for example, 1-1eptyl, dodecyl, octodecyl and oleyl vinyl sulfones he said. Vinyl sulfones, which contain the vinyl sulfone group several times in the molecule, z. B. i, i2-Divi: nylsulfonoctodecan, can implement accordingly often. The vinyl alkyl sulfones can also have branched chains and other atoms or groups of atoms, z. B. halogen atoms or hydroxyl, alkoxy, oxalkyl, nitro, amino, sulfhydryl, Contain Ca, rboxyl or sulfanic acid groups.
Bei der Umsetzung, die in Gegenwart von unter den Reaktionsbedingungen inerten Lösungs- oder Verdünnungsmitteln, wie Wasser oder wäßrigem Alkohol, und gegebenenfalls unter Druck .erfolgt, lagert sich das Bisulfit an die Vinylsulfangruppe unter Bildung von sulfonsauren Salzen ,an. Die neuen Verbindungen können vor allem in der Textilindustrie als Netz-, Reinigungs:, Dispergier-, Durchfärbe-, Egalisier-, Weichma chungs- und Imprägnierungsmittel verwendet werden.In the reaction carried out in the presence of under the reaction conditions inert solvents or diluents such as water or aqueous alcohol, and if necessary under pressure, the bisulfite attaches itself to the vinylsulane group with the formation of sulfonic acid salts. Above all, the new connections can in the textile industry as wetting, cleaning, dispersing, through-dyeing, leveling, Softening and impregnating agents are used.
Wenn es auch bekannt ist, daß N.atritunbisulfit sich .an (3-Chloräfhylvinyls,ulfon anlagern kann, so ist es doch ,als nicht vorauszusehender technischer Fortschritt gegenüber diesem Stande der Technik anzusehen, daß man nach dem vorstehend beschriebenen Verfahren der Textilindustrie eine neue Klasse von wertvollen Hilfsmitteln erschlossen hat. Beispiel i Eine Mischung von 6o Teilen Dodecylvinylsulfon und 3oo Teilen 38 bis 4oo;oiger Natriumbisulfitlösung wird etwa 7 Stunden lang bei rund ioo° gerührt. Nach dem Abkühlen wird der farblose Kristallbrei von der Mutterlauge abgetrennt und aus Wasser umkristallisiert, wobei man farblose Kristalle erhält, deren Zusammensetzungwahrscheinlichder Formel CH3#(CH2)ü#S02#CH2#CH2#S03Na entspricht. Sie sind in Wasser gut (etwas seifenähnlich) löslich, .schwer löslich in kaltem, leicht in heißem Äthanol.Even though it is known that atrite bisulfite is an (3-chloroethylvinylsulfon can accumulate, it is, as technical progress that cannot be foreseen compared to this prior art to be seen that one after the above-described Process of the textile industry opened up a new class of valuable tools Has. Example i A mixture of 60 parts of dodecyl vinyl sulfone and 300 parts of 38 Up to 4oo; oiger sodium bisulfite solution is stirred for about 7 hours at around 100 °. After cooling, the colorless crystal slurry is separated from the mother liquor and recrystallized from water to give colorless crystals, the composition of which is likely to be Formula CH3 # (CH2) ü # S02 # CH2 # CH2 # S03Na corresponds. They are good in water (somewhat soap-like) soluble, sparingly soluble in cold, slightly in hot ethanol.
Entsprechende Verbindungen .erhält man mit anderen Vinylalkylsulfonen, z. B. mit Octodecyl- oder Oleylvinylsulfon, und .den Gemischen von Vinylalkylsulfonen, wie sie beispielsweise aus den verschiedenen höhermolekular en Alkoholen erhalten werden können,)',' Beispiel 2 53 Teile Octodecylvinyls.ulfon, das z.. B. durch Umsetzung von Octo,decylmercaptanm mit Äfhylen und nachfolgende Oxydation erhalten werden kann, werden mit ioo Teilen Natriumbisulfitlösung q. Stunden lang im Wasserbad unter ,gutem Rühren erhitzt. Nach dem Erkalten werden die ausgeschiedenen Kristalle abgesaugt, mit Äther gewaschen und aus Alkohol umkristallisiert. Die erhaltene Verbindung C18 H37 S 02 C H2 C H2 S 03 Na bildet eine farblose Kristallmasse, die sich oberhalb 225° zersetzt. Sie ist in Wasser gut löslich.Corresponding compounds are obtained with other vinyl alkyl sulfones, z. B. with Octodecyl or oleyl vinyl sulfone, and the mixtures of Vinyl alkyl sulfones, such as those from the various higher molecular weight en alcohols can be obtained,) ',' Example 2 53 parts of octodecylvinylsulfone, for example by reacting octo, decylmercaptanm with Äfhylen and subsequent Oxidation can be obtained with 100 parts of sodium bisulfite solution q. hours Heated for a long time in a water bath, stirring well. After cooling down, the excreted Sucked off crystals, washed with ether and recrystallized from alcohol. The received Compound C18 H37 S 02 C H2 C H2 S 03 Na forms a colorless crystal mass which decomposes above 225 °. It is readily soluble in water.
Verwendet man statt Natriumbisulfit Kalium- oder Calciumbisulfit, so erhält man das entsprechende Kalium bzw. Calciumsalz.If you use potassium or calcium bisulfite instead of sodium bisulfite, in this way the corresponding potassium or calcium salt is obtained.
22 Teile eines Produktes, das zu etwa 9o% aus i, z2-Octodecandivinyldisujfon
besteht (hergestellt ,aus Ricinolsäure über das. i-i2-Octodeca.ndiol ,i-i2-Octodecandibromid,
i-i2-Octodecandithiol, i - 12 - Octodeaandivinyldi-
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI51249D DE681338C (en) | 1934-12-18 | 1934-12-18 | Process for the production of sulfonic acid salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI51249D DE681338C (en) | 1934-12-18 | 1934-12-18 | Process for the production of sulfonic acid salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE681338C true DE681338C (en) | 1939-09-19 |
Family
ID=7193029
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI51249D Expired DE681338C (en) | 1934-12-18 | 1934-12-18 | Process for the production of sulfonic acid salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE681338C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2515120A (en) * | 1950-07-11 | Production of organic compounds |
-
1934
- 1934-12-18 DE DEI51249D patent/DE681338C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2515120A (en) * | 1950-07-11 | Production of organic compounds |
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