CH207657A - Process for the preparation of an aromatic sulfonic acid substituted in the nucleus. - Google Patents
Process for the preparation of an aromatic sulfonic acid substituted in the nucleus.Info
- Publication number
- CH207657A CH207657A CH207657DA CH207657A CH 207657 A CH207657 A CH 207657A CH 207657D A CH207657D A CH 207657DA CH 207657 A CH207657 A CH 207657A
- Authority
- CH
- Switzerland
- Prior art keywords
- nucleus
- sulfonic acid
- aromatic sulfonic
- preparation
- acid substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 3
- 229910015900 BF3 Inorganic materials 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000003518 caustics Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001035 methylating effect Effects 0.000 claims description 2
- -1 p-dodecylphenylmethyl ether Chemical compound 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LADIVRBRZUFJDV-UHFFFAOYSA-N 1-methoxy-4-octadecylbenzene Chemical compound CCCCCCCCCCCCCCCCCCc1ccc(OC)cc1 LADIVRBRZUFJDV-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer im Kern substituierten aromatischen Sulfonsäure. Im Hauptpatent ist ein Verfahren zur Herstellung einer im Kern substituierten aro matischen Sulfonsäure beschrieben, welches darin besteht, dass man auf p-Octadecylphenyl- methyläther Chlorsulfonsäure einwirken lässt.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung einer im Kern substituierten aromatischen Sulfonsäure, dadurch gekennzeichnet, dass man auf den durch Kondensation von Phenol mit durch Polymerisation von Propylen hergestelltem Dodecylen in Gegenwart von Borfluorid und durch Methylieren des Kondensationsproduk tes erhaltenen p-Dodecylphenylmethyläther Chlorsulfonsäure zur Einwirkung bringt.
Die durch Umsetzung mit Ätzalkalien, z. B. Natronlauge, Kalilauge, entstehenden Alkalisalze sind wasserlöslich und hervor ragend kapillaraktiv. Sie sind besonders als Wasch- und Netzmittel zu verwenden.
Beispiel: In 276 Gewichtsteile eines Alkylphenol- methyläthers, der durch in Gegenwart von Borfluorid erfolgte Kondensation von Phenol mit durch Polymerisation von Propylen er haltenem Dodecylen und anschliessende Me- thylierung erhalten wurde, werden 128 Ge wichtsteile Chlorsulfonsäure eingetragen, so dass die Temperatur 40 nicht übersteigt.
So bald das Reaktionsprodukt in Wasser klar löslich geworden ist, was nach etwa einer Stunde erreicht ist, wird mit der gleichen Menge Wasser versetzt und mit Natronlauge neutralisiert. Nach dem Eindampfen erhält man ein pulverförmiges Produkt. von schwach gelblicher Farbe von hervorragender Schaum-, Wasch- und Netzwirkung.
Process for the preparation of an aromatic sulfonic acid substituted in the nucleus. The main patent describes a process for the production of an aromatic sulfonic acid with a substituted core, which consists in allowing chlorosulfonic acid to act on p-octadecylphenyl methyl ether.
The present invention relates to a process for the preparation of an aromatic sulphonic acid with a substituted nucleus, characterized in that chlorosulphonic acid is used on the p-dodecylphenylmethyl ether obtained by condensation of phenol with dodecylene produced by polymerisation of propylene in the presence of boron fluoride and by methylating the condensation product Brings influence.
The reaction with caustic alkalis, z. B. caustic soda, potassium hydroxide, resulting alkali salts are water-soluble and outstanding capillary-active. They are particularly useful as detergents and wetting agents.
Example: 128 parts by weight of chlorosulfonic acid are introduced into 276 parts by weight of an alkylphenol methyl ether obtained by the condensation of phenol in the presence of boron fluoride with dodecylene obtained by polymerization of propylene and subsequent methylation, so that the temperature does not exceed 40 .
As soon as the reaction product has become clearly soluble in water, which is achieved after about an hour, the same amount of water is added and the mixture is neutralized with sodium hydroxide solution. After evaporation, a powdery product is obtained. of a pale yellowish color with an excellent foam, washing and wetting effect.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE207657X | 1937-05-08 | ||
| CH206178T | 1938-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH207657A true CH207657A (en) | 1939-11-15 |
Family
ID=25724279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH207657D CH207657A (en) | 1937-05-08 | 1938-05-06 | Process for the preparation of an aromatic sulfonic acid substituted in the nucleus. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH207657A (en) |
-
1938
- 1938-05-06 CH CH207657D patent/CH207657A/en unknown
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