DE673731C - Process for the preparation of sulfonic acids of the arylides of higher molecular aliphatic carboxylic acids - Google Patents
Process for the preparation of sulfonic acids of the arylides of higher molecular aliphatic carboxylic acidsInfo
- Publication number
- DE673731C DE673731C DEI58616D DEI0058616D DE673731C DE 673731 C DE673731 C DE 673731C DE I58616 D DEI58616 D DE I58616D DE I0058616 D DEI0058616 D DE I0058616D DE 673731 C DE673731 C DE 673731C
- Authority
- DE
- Germany
- Prior art keywords
- higher molecular
- acids
- arylides
- preparation
- carboxylic acids
- 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
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 title claims description 5
- 150000003460 sulfonic acids Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-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
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- -1 aliphatic carboxamides Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- DTFIPEAYVOZSEU-UHFFFAOYSA-N ethyl(phenyl)sulfamic acid Chemical compound CCN(S(O)(=O)=O)C1=CC=CC=C1 DTFIPEAYVOZSEU-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/08—Sulfation or sulfonation products of fats, oils, waxes, or higher fatty acids or esters thereof with monovalent alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Sulfonsäuren der Arylide höher molekularer aliphatischer Carbonsäuren E, s wurde gefunden, daß man Sulfonsäuren höher molekularer aliphatischer Carbonsäureamide von technisch sehr wertvollen Eigenschaften erhält, wenn man aromatische Amine mit am Kern gebundenen Sulfonsäuregruppen mit höher molekularen aliphatischen ungesättigten Carbon#säuren oder deren Derivaten umsetzt.A process for the preparation of sulfonic acids of the arylides of higher molecular weight aliphatic carboxylic acids E, s has been found that sulfonic acids of higher molecular weight aliphatic carboxamides of technically very valuable properties are obtained if aromatic amines with sulfonic acid groups bonded to the core with higher molecular weight aliphatic unsaturated carboxylic acids or theirs Implements derivatives.
Die auf diese Weise erhaltenen echten Stilfonsäuren sind als solche oder in Form ihrer Salze in neutralen, alkalischen, sauren oder Härtebildner enthaltenen Bädern vorteilhaft verwendbar. Sie besitzen insbesondere ein hohes Netz-, Reinigungs-, Dispergier- und Lösevermögen.The true stilfonic acids obtained in this way are as such or in the form of their salts in neutral, alkaline, acidic or hardness constituents Baths can be used advantageously. In particular, they have a high level of network, cleaning, Dispersing and dissolving power.
Im Vergleich zu der schon bekannten Stearoylanilidsulfonsäure haben die aus ungesättigten aliphatischen Carbonsäuren erhältlichen Verbindungen insbesondere ein erheblich besseres Netz- und Waschvermögen.Compared to the already known stearoylanilide sulfonic acid the compounds obtainable from unsaturated aliphatic carboxylic acids in particular a significantly better wetting and washing power.
B ie i s p i -e 1: 2oo Gewichtsteile N-Äthylanilinsulfonsäure werden in schwach sodaalkalischer Lösung mit 25o Gewichtsteilen ölsäurechlorid -umgesetzt, wobei durch fortlaufende Zugabe von Soda die Lösung während der Umsetzung stets schwach alkalisch gehalten wird. Nach Beendigung der Umsetzung wird das Produkt bis zur lakmussauren Reaktion mit Mineralsäur-e versetzt. Nach Abtrennung der nebenbei aus Olsäurechlorid gebildeten ölsäure erhält man durch Aussalzen ein Produkt von gutem Netzvermögen.B ie ispi -e 1: 200 parts by weight of N-ethylanilinesulfonic acid are reacted in a weakly alkaline soda solution with 250 parts by weight of oleic acid chloride, the solution being kept weakly alkaline during the reaction by continuously adding soda. After the reaction has ended, mineral acids are added to the product until it has a lactic acid reaction. After separating off the oleic acid which is also formed from oleic acid chloride, a product of good wetting power is obtained by salting out.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI58616D DE673731C (en) | 1929-07-28 | 1929-07-28 | Process for the preparation of sulfonic acids of the arylides of higher molecular aliphatic carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI58616D DE673731C (en) | 1929-07-28 | 1929-07-28 | Process for the preparation of sulfonic acids of the arylides of higher molecular aliphatic carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE673731C true DE673731C (en) | 1939-03-27 |
Family
ID=7194818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI58616D Expired DE673731C (en) | 1929-07-28 | 1929-07-28 | Process for the preparation of sulfonic acids of the arylides of higher molecular aliphatic carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE673731C (en) |
-
1929
- 1929-07-28 DE DEI58616D patent/DE673731C/en not_active Expired
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