DE764807C - Process for the preparation of sulfinic acids - Google Patents
Process for the preparation of sulfinic acidsInfo
- Publication number
- DE764807C DE764807C DEZ26800D DEZ0026800D DE764807C DE 764807 C DE764807 C DE 764807C DE Z26800 D DEZ26800 D DE Z26800D DE Z0026800 D DEZ0026800 D DE Z0026800D DE 764807 C DE764807 C DE 764807C
- Authority
- DE
- Germany
- Prior art keywords
- sulfinic acids
- preparation
- sulfochlorides
- sulfonic acid
- carbon atoms
- 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 8
- 150000003455 sulfinic acids Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- -1 sulfonic acid chlorides Chemical class 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
- C07C313/04—Sulfinic acids; Esters thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Description
Verfahren zur Darstellung von Sulfinsäuren Es wurde gefunden, daB sich technisch wertvolle Sulfinsäuren nach an sich bekannten Verfahren herstellen lassen, wenn man als Ausgangsmaterial solche Sulfochloride bzw. Sulfochloridgeinische verwendet, die bei der Behandlung von gesättigten Kohlenwasserstoffen mit einer mittleren Kohlenstoffzahl von 18 Kohleristoffatomen mittels Schwefeldioxyd und Chlor erhalten werden.Process for the preparation of sulfinic acids It has been found that Technically valuable sulfinic acids can be produced by processes known per se let, if you use such sulfochlorides or sulfochloride mixtures as the starting material used in the treatment of saturated hydrocarbons with a average carbon number of 18 carbon atoms using sulfur dioxide and chlorine can be obtained.
Es ist bereits bekannt, nieder- und höhermolekulare Sulfinsäuren'durch Reduktion von Sulfochloriden herzustellen und insbesondere solche mit höhermolekularen Resten als Seifenersatz zu verwenden. Bei dem bisherigen Verfahren werden aber, soweit es sich um aliphatisches Ausgangsgut handelt, nur solche Sulfochloride umgesetzt, bei denen die Sulfogruppe am a-Kohlenstoffatom steht (vgl. z. I3. die deutsche Patentschrift 671827). Ferner war es bekannt, die durch Behandlung von gesättigten Kohlenwasserstoffen mit $ bis 12 Kohlenstoffatomen mittels SO, und Chlor hergestellten Sulfochloride in Sulfinsäuren überzuführen (vgl. z. B. die TJSA.-Patentschrift 2 174 507. It is already known to produce low and higher molecular weight sulfinic acids by reducing sulfochlorides and, in particular, to use those with higher molecular weight residues as a soap substitute. In the previous process, however, insofar as the starting material is aliphatic, only those sulfochlorides are converted in which the sulfo group is on the a-carbon atom (cf. z. I3. German patent 671827). Further, it was known, the sulfonyl chlorides produced by the treatment of saturated hydrocarbons having $ to 12 carbon atoms by means of S O, and chlorine in sulfinic acids convert (see. Eg. As the TJSA. Patent 2,174,507.
Die nach der Erfindung erhaltenen Sulfinsäuren weisen gegenüber diesen bekannten Produkten wertvolle Eigenschaften auf, und zwar dahingehend, daß sie sich infolge ihrer öligen Beschaffenheit sehr leicht mit 'Mineralölen kombinieren lassen und daher auch ein hohes Emulgierungsvermögen für diese hesitzen.The sulfinic acids obtained according to the invention have compared to these well-known products have valuable properties, and to the effect that that because of their oily nature they combine very easily with mineral oils and therefore have a high emulsifying power for them.
Die Herstellung der Sulfinsäuren aus den Sulfochloriden kann nach den bekannten Verfahren erfolgen. z. B. durch Reduktion mittels Zink oder anderer Metalle, wie Eisen; Aluminium, Magnesium, wobei diese am besten in 'feinpulveriger Form zur - Anwendung kommen. . Auch - N atriumamalgam oder Natriumsulfit sind für die Reduktion geeignet. Beispiel i 6o Teile eines Sulfochlorierungsgemisches, das aus einem technischen Kohlenwassersfioffgemi.sch mit einer mittleren Kohlenstoffanzahl von iS C-Atomen (VZ. = 35o) durch Behandlung mit Cl., und S 02 hergestellt wurde, werden auf 6o bis 70° erwärmt und nach und nach-öoTeile -Zinkstaub und 6o Teile Wasser unter dauerndem Rühren eingetragen. Durch Kühlung wird dabei die Temperatur auf etwa So' gehalten. Nach Beendigung des Eintragens wird noch 2 bis 3 Stunden bei der gleichen Temperatur nachgerührt. Die entstandene zähe graue Masse wird dann langsam in iooo Teile ioo/oiger Sodalösung bei So' eingerührt und so lange erwärmt, bis die Zerlegung der Zinksalze vollständig ist. Nach 1# ihration wird sler h;üekstand nochmals reit ;oo Teilen ioo/oigerodah>aung lx#handelt. Aus Neiden Filtraten wird tnit Salzs@iure. gegebenenfalls unter Zugabe von Kochsalz oder Natriumsulfat, die Sulfinsäure abgeschieden. Sie wird in einer Ausbeute von ' etwa ioo Teilen erhalten und stellt ein viskoses Ö1 dar. In Sodalösung, Ammoniak oder Laugen ist die Säure klar löslich; die Lösungen, auch die verdünnten, haben eine starke Schaum-und Netzkraft.The sulfinic acids can be prepared from the sulfochlorides by the known processes. z. B. by reduction using zinc or other metals such as iron; Aluminum, magnesium, whereby these are best used in fine powder form. . N atrium amalgam or sodium sulfite are also suitable for the reduction. EXAMPLE I 6o parts of a sulfochlorination mixture which was produced from a technical hydrocarbon mixture with an average carbon number of iS carbon atoms (VZ. = 35o) by treatment with Cl. And S 02 are heated to 60 to 70 ° and after and after-öo parts zinc dust and 60 parts water entered with constant stirring. The temperature is kept at about 50 ' by cooling. After the end of the entry, the mixture is stirred for a further 2 to 3 hours at the same temperature. The resulting viscous gray mass is then slowly stirred into 1000 parts 100% soda solution at So 'and heated until the decomposition of the zinc salts is complete. After 1 # heration, sler h; üekstand will ride again; oo parts ioo / oigerodah> aung lx # acts. Envy turns into filtrates with hydrochloric acid. optionally with the addition of common salt or sodium sulfate, the sulfinic acid is deposited. It is obtained in a yield of about 100 parts and is a viscous oil. The acid is clearly soluble in soda solution, ammonia or alkalis; the solutions, even the diluted ones, have a strong foaming and wetting power.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ26800D DE764807C (en) | 1941-12-16 | 1941-12-16 | Process for the preparation of sulfinic acids |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ26800D DE764807C (en) | 1941-12-16 | 1941-12-16 | Process for the preparation of sulfinic acids |
| DEZ739D DE912389C (en) | 1942-03-13 | 1942-03-13 | Smelting agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE764807C true DE764807C (en) | 1952-06-26 |
Family
ID=26003294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEZ26800D Expired DE764807C (en) | 1941-12-16 | 1941-12-16 | Process for the preparation of sulfinic acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE764807C (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE671827C (en) * | 1933-11-15 | 1939-02-14 | Henkel & Cie Gmbh | Soap substitutes |
| US2174507A (en) * | 1938-06-30 | 1939-09-26 | Du Pont | Reaction of liquid n-alkanes with sulphur dioxide and chlorine and products thereof |
-
1941
- 1941-12-16 DE DEZ26800D patent/DE764807C/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE671827C (en) * | 1933-11-15 | 1939-02-14 | Henkel & Cie Gmbh | Soap substitutes |
| US2174507A (en) * | 1938-06-30 | 1939-09-26 | Du Pont | Reaction of liquid n-alkanes with sulphur dioxide and chlorine and products thereof |
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