DE721054C - Process for the preparation of alkylated aromatic sulfonic acids - Google Patents
Process for the preparation of alkylated aromatic sulfonic acidsInfo
- Publication number
- DE721054C DE721054C DEZ22695D DEZ0022695D DE721054C DE 721054 C DE721054 C DE 721054C DE Z22695 D DEZ22695 D DE Z22695D DE Z0022695 D DEZ0022695 D DE Z0022695D DE 721054 C DE721054 C DE 721054C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acids
- alkylated aromatic
- aromatic sulfonic
- preparation
- sulfuric acid
- 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
- -1 alkylated aromatic sulfonic acids Chemical class 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000008233 hard water Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- WHHKAGDFPQFXLL-QPLCGJKRSA-N (Z)-tetratriacont-9-en-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC\C=C/CCCCCCCCO WHHKAGDFPQFXLL-QPLCGJKRSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- HGWAKQDTQVDVRP-OKULMJQMSA-N butyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCCC HGWAKQDTQVDVRP-OKULMJQMSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C07C303/04—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 substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—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 substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
Description
Verfahren zur Darstellung von alkylierten aromatischen Sulfonsäuren Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung von alkylierten aromatischen Sulfonsäuren, das darin besteht, daß man aromatische Kohlenwasserstoffe in Mischung mit aliphatischen Oxyverbindungen mit mehr als acht Kohlenstoffatomen mit konzentrierter Schwefelsäure, und zwar in Gegenwert von Natriumpyrosulfat, behandelt: Die .erhaltenen alkylierten aromatischen Sulfonsäuren bzw. deren Alkalisalze dienen als -Hilfsmittel in der Textil- und Lederindustrie, insbesondere als Netz-, Reinigungs= und Dispergiermittel.Process for the preparation of alkylated aromatic sulfonic acids The present invention is a process for the preparation of alkylated aromatic sulfonic acid, which consists in having aromatic hydrocarbons in a mixture with aliphatic oxy compounds with more than eight carbon atoms treated with concentrated sulfuric acid in the equivalent of sodium pyrosulphate: The alkylated aromatic sulfonic acids or their alkali metal salts obtained are used as -Auxiliaries in the textile and leather industry, especially as a net, cleaning = and dispersants.
Beispiel r j,o6 Teile Xylol, 24o Teile eines Cetyloleylalkoholgemisches mit der Jodzahl 5 5 und 25o Teile Natriumpyrosulfat werden bei 45 bis 5o° unter Rühren allmählich mit 650 Teilen konzentrierter Schwefelsäure versetzt. Nach Verlauf von z bis 3 Stunden wäscht man das Gerrüsch mit Eiswasser und neutralisiert anschließend mit Alkälilauge. Die erhaltene weißlichgelbe Paste ist in Wasser klar löslich.Example rj, 06 parts of xylene, 24o parts of a cetyl oleyl alcohol mixture with an iodine number of 5.5 and 250 parts of sodium pyrosulfate are gradually admixed with 650 parts of concentrated sulfuric acid at 45 ° to 50 ° with stirring. After z to 3 hours, the framework is washed with ice water and then neutralized with alkali. The whitish yellow paste obtained is clearly soluble in water.
Beispiel 2 -35 Teile Toluol, 38 Teile Natriumpyrosulfat und 12o Teile Ricinolsäurebutylester werden bei 2o bis 30° allmählich unter Rühren mit Zoo Teilen konzentrierter Schwefelsäure versetzt. Nach Beendigung der Sulfonierung wäscht man das Reaktionsgemisch mit Eiswasser und neutralisiert anschließend.-Die :erhaltene helle Paste löst sich klar in Wasser.Example 2 -35 parts of toluene, 38 parts of sodium pyrosulphate and 120 parts Ricinoleic acid butyl ester at 2o to 30 ° gradually with stirring with zoo parts concentrated sulfuric acid. After the sulfonation has ended, it is washed the reaction mixture with ice water and then neutralized.-The: obtained light-colored paste dissolves clearly in water.
Es ist bereits bekannt, alkylierte aromatische Sulfonsäuren aus aromatischen Kohlenwasserstoffen, aliphatischen Oxyverbindungen und konzentrierter Schwefelsäure allein herzustellen. Diese Arbeitsweise führt zwar bei Verwendung niedrigmolekulaxer aliphatischer Oxyverbindungen zu einwandfreien Er-" gebnissen,- bei Verwendung höhermolekularer aUphatischer Oxyvexbindungen sinkt jedoch die Ausbeute beträchtlich. Versucht man in diesem Falle; die Ausbeute durch Amvendung stärker wirkender Sulfonierungsmittel, wie Oleum oder Chlorsulfonsäure, zu erhöhen, so sind die erhaltenen alkylierten aromatischen Sulfonsäuren dunkel gefärbt und können im allgemeinen erst nach entsprechender Reinigung Verwendung finden. Demgegenüber werden bei dem erfindungsgemäßen Vierfahren ohne Schwierigkeiten und in ,guter Ausbeute helle Erzeugnisse verhalten, die eine unmittelbare Verwendung gestatten.It is already known to alkylated aromatic sulfonic acids from aromatic Hydrocarbons, aliphatic oxy compounds and concentrated sulfuric acid to manufacture alone. This procedure leads to a low molecular weight when used aliphatic oxy compounds to perfect results, - when using higher molecular weight However, the yield of phosphatic oxyvex bonds decreases considerably. One tries in this case; the yield by using stronger sulfonating agents, such as oleum or chlorosulfonic acid, the obtained are alkylated aromatic sulfonic acids darkly colored and can generally only be used after appropriate Cleaning find use. In contrast, the four-wheel drive according to the invention without difficulty and in good yield bright products behave the one allow immediate use.
Die. erfindungsgemäß erhältlichen alkylierten aromatischen Sulfonsäuren zeichnen sich weiterhin dadurch aus, daß sie in. @lestilli@ertem Wasser, sowie in 20%iger Schwefelsäure klar löslich@-sind und in hartem Wasser riur zu einer ganz schwachen Trübung Anlag' geben. Auch nach 30 Minuten langem Koch=en zeigen die Lösungen der Sulfonsäuren @Jn" destilliertem Wasser oder in 20° harteril-. Wasser noch die gleichen Eigenschaften.The. Alkylated aromatic sulfonic acids obtainable according to the invention are furthermore distinguished by the fact that they are clearly soluble in distilled water and in 20% sulfuric acid and give rise to a very slight cloudiness in hard water. Even after boiling for 30 minutes, the solutions of the sulfonic acids in distilled water or in 20 ° hard water still show the same properties.
Die günstigen Eigenschaften der erfindungsgemäß erhältlichen Sulfonsäuren sind um so überraschender, als Sulfonate, die aus aromatischen Kohlenwasserstoffee und höhermolekularen aliphatischen Oxyverbindungenstatt mit konzentrierter Schwefelsäure und Natriumpyrosulfat mit Hilfe von Oleum mit einem entsprechenden Gehalt an Schwefieltrioxyd gewonnen sind, keine klaren Lösungen geben, weder in 20%iger Schwefelsäure noch in hartem Wasser und auch nicht in destilliertem Wasser .und erst recht nicht nach 30 Minuten langem Kochen. . Das-erfindungsgemäße Verfahren konnte auch .nicht aus dem bekannten Verfahren entnommen werden, bei welchem unsulfo-'- eierte alkylierte aromatische Verbindungen mit Hilfe von Schwefelsäuremonohydrat und Alkalipyrosulfat aus aromatischen Kohlen-*asserstoffen und niedrigmolekularen Alko-=holen hergestellt werden.The favorable properties of the sulfonic acids obtainable according to the invention are all the more surprising as sulfonates, which are obtained from aromatic hydrocarbons and higher molecular weight aliphatic oxy compounds instead of concentrated sulfuric acid and sodium pyrosulfate with the help of oleum with a corresponding content of sulfur trioxide, do not give clear solutions, neither in 20%. iger sulfuric acid in hard water and not in distilled water, and certainly not after 30 minutes of boiling. . The process according to the invention could also not be taken from the known process in which unsulfonated alkylated aromatic compounds are produced from aromatic carbons and low molecular weight alcohols with the aid of sulfuric acid monohydrate and alkali pyrosulfate.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ22695D DE721054C (en) | 1935-08-22 | 1935-08-22 | Process for the preparation of alkylated aromatic sulfonic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ22695D DE721054C (en) | 1935-08-22 | 1935-08-22 | Process for the preparation of alkylated aromatic sulfonic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE721054C true DE721054C (en) | 1942-05-27 |
Family
ID=7625711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEZ22695D Expired DE721054C (en) | 1935-08-22 | 1935-08-22 | Process for the preparation of alkylated aromatic sulfonic acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE721054C (en) |
-
1935
- 1935-08-22 DE DEZ22695D patent/DE721054C/en not_active Expired
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