DE690563C - Process for the preparation of organic sulfonic acids of amides from aliphatic-aromatic amines and higher molecular weight aliphatic saturated carboxylic acids - Google Patents
Process for the preparation of organic sulfonic acids of amides from aliphatic-aromatic amines and higher molecular weight aliphatic saturated carboxylic acidsInfo
- Publication number
- DE690563C DE690563C DE1930I0061214 DEI0061214D DE690563C DE 690563 C DE690563 C DE 690563C DE 1930I0061214 DE1930I0061214 DE 1930I0061214 DE I0061214 D DEI0061214 D DE I0061214D DE 690563 C DE690563 C DE 690563C
- Authority
- DE
- Germany
- Prior art keywords
- aliphatic
- acids
- molecular weight
- amides
- aromatic amines
- 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
- 150000001735 carboxylic acids Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 150000003460 sulfonic acids Chemical class 0.000 title claims description 5
- 150000001408 amides Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000001931 aliphatic group Chemical group 0.000 title description 5
- 229920006395 saturated elastomer Polymers 0.000 title description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- -1 aliphatic carbonic acids Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- MLGPKWUKOQAAGI-UHFFFAOYSA-N N-benzylhexadecanamide Chemical compound CCCCCCCCCCCCCCCC(=O)NCC1=CC=CC=C1 MLGPKWUKOQAAGI-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the 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
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 organischen Sulfonsäuren von Amiden aus aliphatischaromatischen Aminen und höhermolekularen aliphatischen gesättigten Carbonsäuren Im Patent 673 730 ist ein Verfahren zur Herstellung von Sulfonsäuren aus Amideln beschrieben, bei dem man Sulfonsäuregruppen enthaltende aromatische Amine, die im Kern oder am Stickstoff durch aliphatische oder aliphatisch-aromatische Kohlenwasserstoffreste substituiert sind, mit höhermolekularen aliphatischen gesättigten Carbonsäuren oder deren Derivaten umsetzt oder in Säureamide aus den genannten Aminen, die keine Sulfonsäure,-,ruppen aufweisen, und den erwähnten Carbonsäuren Sulf«nsäuregruppen einführt.A process for the preparation of organic sulfonic acids amides from aliphatic-aromatic amines, and higher molecular weight aliphatic saturated carboxylic acids in patent 673,730 a method for the production of sulfonic acids from Amideln is described, comprising the steps of sulfonic aromatic amines, which in the core or at the nitrogen by aliphatic or aliphatic- aromatic hydrocarbon radicals are substituted, are reacted with higher molecular weight aliphatic saturated carboxylic acids or their derivatives, or sulfonic acid groups are introduced into acid amides from the amines mentioned which have no sulfonic acid groups and the carboxylic acids mentioned.
Es wurde nun gefunden, daß mzneb#enfalls technisch vorteilhaft verwendbare Sulfonsäuren von Anliden höhermolekularer gesättigter aliphatischer Carbonsäuren erhalten kann, wenn man bei dein vorerwälmten Verfahren aEphatisch-a-romatische Amine oder deren Sulfonsäuren verwendet, welche die Aminogruppe an ein-en aliphatischen Rest gebunden enthalten. Beisp iel ioo'Gewichtsteü,e Palmitinsäure werden =-sammen mit i oo Gewichtsteilen Benzylamin so lange zum Sieden erlutzt, bis die Wasserabspaltung beendet ist. Das noch heiße Produkt -wird zur Reinigung in Alkohol eingetragen, aus dem es heim Erkalten auskristallisiert. 115 Gewichtsteile des Palmitinsäurebenzylamids werden in 2oo Gewichtsteilen Schwefelsäur-emon#ohydrat gelöst und -dann- nach Zusatz von i5o Gewichtsteilen Oleum von 23% SO,3-Gehalt bei 35 bis 40' sulfOniert. Nach etwa 2 Stunden ist die Sulfonierung beendet. Das Sulfonier-ungsgemisch wird auf Eis gegossen und die erhaltene Lösung mit Kalilauge neutralisiert. Das dabei -ausgeschiedene Kaliumsalz der gebildeten Sulfonsäure wird von der Sulfatlauge abgetrennt; es besitzt ein ausgezeichnetes Waschvermögen.It has now been found that mzneb # can also be used with technical advantage Sulphonic acids of anlides of higher molecular weight saturated aliphatic carboxylic acids can be obtained if, in your previously mentioned method, one is aEphatic-a-romantic Amines or their sulfonic acids are used which have the amino group on an aliphatic Rest bound included. For example 100 parts of weight of palmitic acid are combined with 100 parts by weight of benzylamine to boil until the elimination of water is finished. The still hot product is added to alcohol for cleaning, from which it crystallizes when it cools down. 115 parts by weight of the palmitic acid benzylamide are dissolved in 2oo parts by weight of sulfuric acid emon # ohydrate and then after addition of 150 parts by weight of oleum with 23% SO.3 content at 35 to 40 'sulfonated. To The sulfonation is complete in about 2 hours. The sulfonation mixture is on Poured ice and neutralized the resulting solution with potassium hydroxide solution. The one that was eliminated The potassium salt of the sulfonic acid formed is separated off from the sulfate liquor; it owns excellent detergency.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1930I0061214 DE690563C (en) | 1930-04-01 | 1930-04-01 | Process for the preparation of organic sulfonic acids of amides from aliphatic-aromatic amines and higher molecular weight aliphatic saturated carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1930I0061214 DE690563C (en) | 1930-04-01 | 1930-04-01 | Process for the preparation of organic sulfonic acids of amides from aliphatic-aromatic amines and higher molecular weight aliphatic saturated carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE690563C true DE690563C (en) | 1940-04-29 |
Family
ID=7195420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1930I0061214 Expired DE690563C (en) | 1930-04-01 | 1930-04-01 | Process for the preparation of organic sulfonic acids of amides from aliphatic-aromatic amines and higher molecular weight aliphatic saturated carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE690563C (en) |
-
1930
- 1930-04-01 DE DE1930I0061214 patent/DE690563C/en not_active Expired
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