DE893340C - Process for the preparation of alkylarylsulfonic acids and their salts - Google Patents
Process for the preparation of alkylarylsulfonic acids and their saltsInfo
- Publication number
- DE893340C DE893340C DEZ708D DEZ0000708D DE893340C DE 893340 C DE893340 C DE 893340C DE Z708 D DEZ708 D DE Z708D DE Z0000708 D DEZ0000708 D DE Z0000708D DE 893340 C DE893340 C DE 893340C
- Authority
- DE
- Germany
- Prior art keywords
- salts
- acids
- products
- sulfonated
- alkylated
- 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
- 239000002253 acid Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 9
- 150000007513 acids Chemical class 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 title claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 230000029936 alkylation Effects 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 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
- -1 naphthalene Chemical class 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000006277 sulfonation reaction Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 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
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013861 fat-free Nutrition 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- VBMHLJHEUUUOEG-UHFFFAOYSA-N sulfuric acid sulfur trioxide Chemical compound S(O)(O)(=O)=O.S(=O)(=O)=O.S(O)(O)(=O)=O VBMHLJHEUUUOEG-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Description
Verfahren zur Herstellung von .Alkylarylsulfonsäuren bzw. deren Salzen Es wurde gefunden, daß man Alkylarylsulfonsäuren bzw. deren Salze erhalten kann, wenn man aromatische Kohlenwasserstoffe, wie Naphthalin, mit Oxyverbindungen, im folgenden Vorlaufalkohole genannt, die durch Reduktion von sogenannten Vo.rlauffettsäuren nach dem Verfahren des Patents 764 888 gewonnen werden können, alkyliert und die Alkylierungsprodukte sulfoniert und erforderlichenfalls neutralisiert.Process for the production of .Alkylarylsulfonsäuren and their salts It has been found that alkylarylsulfonic acids or their salts can be obtained, if you aromatic hydrocarbons, such as naphthalene, with oxy compounds, im The following initial alcohols are called, which are obtained through the reduction of so-called full-run fatty acids can be obtained by the method of patent 764 888, alkylated and the Sulfonated alkylation products and neutralized if necessary.
Unter Vorlauffettsäuren. werden solche Carbonsäuren verstanden, die als Vorläufe bei der Destillation des verseifbarenAnteils der Oxydationsprodukte von Paraffin. oder sonstigen Kohlenwasserstoffen anfallen. Sie weisen durchschnittlich folgende Kennzahlen auf: Säurezahl 368, Verseifungszahl 385, Hy droxylzahl 56. Die zur Alkylierung nach vorliegendem Verfahren verwendbaren Reduktionsprodukte aus oben näher bezeichneten Carbonsäuren sind im allgemeinen durch Hydroxylzahlen von 36o bis 4q.o gekennzeichnet und haben einen Siedeintervall von 135 bis 24.o°. Außer diesen Reduktionsprodukten können gleichzeitig mit diesen auch noch niedermolekulare n-Alkohole oder deren Isoformen mit weniger als 5 C-Atomen zur Alkylierung mitverwendet werden, z. B. Äthylalkohol, n-Butylalkohol, Isopropylalkohol u. dgl.Under runner fatty acids. those carboxylic acids are understood which as forerunners in the distillation of the saponifiable fraction of the oxidation products of paraffin. or other hydrocarbons. They show average the following indicators: acid number 368, saponification number 385, hydroxyl number 56. The for alkylation by the present process usable reduction products Carboxylic acids described in more detail above are generally characterized by hydroxyl numbers of 36o to 4q.o and have a boiling range of 135 to 24.o °. Except these reduction products can also be low molecular weight at the same time as these n-alcohols or their isoforms with fewer than 5 carbon atoms are also used for the alkylation be e.g. B. ethyl alcohol, n-butyl alcohol, isopropyl alcohol and the like.
Man kann das Verfahren so leiten, daß entweder die aromatischen Kohlenwasserstoffe zunächst alkyliert und danach sulfoniert werden, oder man alkyliert und sulfoniert in einem Arbeitsgang. Als Sulfonierungs- bzw. Alkylierungsmittel können neben Schwefelsäure auch Oleum, Chlorsulfonsäure u. dgl. Verwendung finden. Die Sulfonsäuren werden wahlweise mit anorganischen oder organischen Basen neutralisiert.One can conduct the process in such a way that either the aromatic hydrocarbons first alkylated and then sulfonated, or alkylated and sulfonated in one operation. As sulfonating or alkylating agents, in addition to sulfuric acid oleum, chlorosulfonic acid and the like can also be used. The sulfonic acids are optionally neutralized with inorganic or organic bases.
Die nach vorliegendem Verfahren anfallenden Alkylarylsulfonsäuren bzw. deren Salze sind Hilfsmittel für die Papier-, Leder- und Textilindustrie. Außerdem können sie als fettfreie Waschmittel für den Haushalt und als Handwaschmittel inForm von Pasten, Pulvern oder Stücken benutzt werden.The alkylarylsulfonic acids obtained by the present process or their salts are auxiliaries for the paper, leather and textile industries. aside from that can be used as a fat-free laundry detergent for the household and as a hand wash inForm of pastes, powders or pieces.
Beispiel i 64 g Naphthalin und 8o g Vorlaufalkohol, OH-Zahl 35,6, werden mit 5i: 2g Schwefelsäure 66i°; Be bei io bis i5° sulfoniert und gleichzeitig alkyliert. Nachdem sämtliche Schwefelsäure dem Reaktionsgemisch zugeführt worden ist, erwärmt man 9 Stunden auf 45°. Man läßt absitzen und entfernt die überschüssige Schwefelsäure. Darauf wird das saure Alkylarylsulfonat mit 75 g Eis gewaschen. Das Säurewasser wird abgezogen ünd das saure Sulfonat mit Natronlauge neutralisiert. Man erhält braune, pastenförmige Produkte.Example i 64 g of naphthalene and 80 g of initial alcohol, OH number 35.6, are with 5i: 2g sulfuric acid 66 °; Be sulfonated at 10 to 15 ° and at the same time alkylated. After all the sulfuric acid has been added to the reaction mixture is heated to 45 ° for 9 hours. It is allowed to settle and the excess is removed Sulfuric acid. The acidic alkylarylsulfonate is then washed with 75 g of ice. That Acid water is drawn off and the acid sulphonate is neutralized with sodium hydroxide solution. Brown, paste-like products are obtained.
Beispiel e 64 g ` Naphthalin, 64,2 g Vorlaufalkohol und 345 g Isopropylalkohol werden, wie unter Beispiel i angegeben, mit 512 g Schwefelsäure 66°, Be alkyliert und gleichzeitig sulfoniert. Die Aufarbeitung geschieht, wie unter Beispiel i angegeben. Die Alkylarylsulfonsäure wird mit Triäthanolamin neutralisiert. Man erhält eine bräunlich gefärbte Paste.Example e 64 g of naphthalene, 64.2 g of initial alcohol and 345 g of isopropyl alcohol are, as stated in Example i, alkylated with 512 g of sulfuric acid 66 °, Be and sulfonated at the same time. The work-up is carried out as indicated under Example i. The alkylarylsulfonic acid is neutralized with triethanolamine. You get one brownish colored paste.
Be-ispiel3 64 g Naphthalin, 46.,2 g V'orlaufalkohol mit einer O H-Zahl von 390 und 31,5 g n-Butanol werden mit 5i,21 g Schwefelsäure 66° Be alkyliert und gleichzeitig sulfoniert. Das anfallende Alkylarylsulfonat wird nach Beispiel i oder 2 aufgearbeitet. Es werden bräunlich gefärbte Produkte erhalten.Example3 64 g of naphthalene, 46th, 2 g of first-run alcohol with an OH number of 390 and 31.5 g of n-butanol are alkylated with 51, 21 g of 66 ° Be sulfuric acid and sulfonated at the same time. The resulting alkylarylsulfonate is worked up according to Example 1 or 2. Brownish colored products are obtained.
Die anfallenden neutralen pastenförmigen Alkylarylsulfonate besitzen gute Netz- und Schaumwirkung und können nach bekannten Verfahren der Trocknung unterworfen werden. Man. erhält auf diese Weise auch pulverförmige Produkte. Als Handwaschmittel können sie unter Zugabe vonFüllstoffen zu Stücken geformt werden.The resulting neutral pasty alkylarylsulfonates have good wetting and foaming effect and can be subjected to drying by known methods will. Man. In this way, it also receives products in powder form. As a hand detergent they can be shaped into pieces with the addition of fillers.
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ690D DE908495C (en) | 1940-11-12 | 1940-11-12 | Process for the preparation of alkylarylsulfonic acids and their salts |
| DEZ708D DE893340C (en) | 1940-11-12 | 1940-11-12 | Process for the preparation of alkylarylsulfonic acids and their salts |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ690D DE908495C (en) | 1940-11-12 | 1940-11-12 | Process for the preparation of alkylarylsulfonic acids and their salts |
| DEZ708D DE893340C (en) | 1940-11-12 | 1940-11-12 | Process for the preparation of alkylarylsulfonic acids and their salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE893340C true DE893340C (en) | 1953-10-15 |
Family
ID=32991802
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEZ708D Expired DE893340C (en) | 1940-11-12 | 1940-11-12 | Process for the preparation of alkylarylsulfonic acids and their salts |
| DEZ690D Expired DE908495C (en) | 1940-11-12 | 1940-11-12 | Process for the preparation of alkylarylsulfonic acids and their salts |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEZ690D Expired DE908495C (en) | 1940-11-12 | 1940-11-12 | Process for the preparation of alkylarylsulfonic acids and their salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE893340C (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE525158C (en) * | 1925-12-29 | 1931-06-02 | I G Farbenindustrie Akt Ges | Process for the preparation of substituted aromatic sulfonic acids |
| FR706131A (en) * | 1929-12-10 | 1931-06-19 | Manufacturing process of water soluble sulfonated products and their applications | |
| GB364537A (en) * | 1930-09-22 | 1931-12-22 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of wetting, cleansing and dispersion agents |
| FR718809A (en) * | 1930-09-03 | 1932-01-29 | Ig Farbenindustrie Ag | Process for the production of humectants, detergents, dispersants, etc. |
| DE597034C (en) * | 1930-08-01 | 1934-05-22 | Cie Nat Matieres Colorantes | Process for the preparation of sulfonated condensation products |
| FR825861A (en) * | 1936-08-24 | 1938-03-16 | Houghton Fabrik K G Deutsche | Manufacturing process for products with high surface activity |
-
1940
- 1940-11-12 DE DEZ708D patent/DE893340C/en not_active Expired
- 1940-11-12 DE DEZ690D patent/DE908495C/en not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE525158C (en) * | 1925-12-29 | 1931-06-02 | I G Farbenindustrie Akt Ges | Process for the preparation of substituted aromatic sulfonic acids |
| FR706131A (en) * | 1929-12-10 | 1931-06-19 | Manufacturing process of water soluble sulfonated products and their applications | |
| DE597034C (en) * | 1930-08-01 | 1934-05-22 | Cie Nat Matieres Colorantes | Process for the preparation of sulfonated condensation products |
| FR718809A (en) * | 1930-09-03 | 1932-01-29 | Ig Farbenindustrie Ag | Process for the production of humectants, detergents, dispersants, etc. |
| GB364537A (en) * | 1930-09-22 | 1931-12-22 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of wetting, cleansing and dispersion agents |
| FR825861A (en) * | 1936-08-24 | 1938-03-16 | Houghton Fabrik K G Deutsche | Manufacturing process for products with high surface activity |
Also Published As
| Publication number | Publication date |
|---|---|
| DE908495C (en) | 1954-04-05 |
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