CH198705A - Process for the preparation of a water-soluble aromatic series compound. - Google Patents
Process for the preparation of a water-soluble aromatic series compound.Info
- Publication number
- CH198705A CH198705A CH198705DA CH198705A CH 198705 A CH198705 A CH 198705A CH 198705D A CH198705D A CH 198705DA CH 198705 A CH198705 A CH 198705A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- preparation
- aromatic series
- series compound
- soluble aromatic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 aromatic series compound Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 5
- 229920002678 cellulose Polymers 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 238000006277 sulfonation reaction 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)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
Verfahren zur Herstellung einer wasserlöslichen Verbindung der aromatischen Reihe. Es wurde gefunden, dass man neue, was serlösliche Abkömmlinge der aromatischen Reihe erhält, wenn man Verbindungen von folgendem schematischem Aufbau
EMI0001.0002
wobei unter Ar aromatische Reste verstanden werden, g in der ms-Stellung einen aliphati- schen oder alicyclischen Substituenten mit mehr als 5 C-Atomen bedeutet und die freien Stellen der aromatischen Kerne beliebig, vor nehmlich aber durch organische Reste substi tuiert sein können,
mit sulfonierenden Mitteln behandelt.
Als Ausgangsmaterialien für die Sulfonie- rung kommen die in der ms-Stellung durch aliphatische oder alicyelische Gruppen mit mehr als 5 C-Aromen substituierten Desoxy- benzoine in Frage. Zu diesen zum Teil neuen Verbindungen gelangt man leicht nach be kannten Verfahren (siehe z. B. Ber. d. Deut- sehen Chem. Gesellschaft Bd. 21, Seite 1299 und Bd. 25, Seite 2239.
Die nach der Sul- fierung dieser substituierten Desoxybenzoine erhaltenen Körper stellen in Form ihrer lös lichen Metallsalze wertvolle Netz-, Disper- gier- und Emulgiermittel dar, insbesondere ist ihre Weichmachungswirkung interessant.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung des Natron salzes der ms-Octodecyl-p-methyl-desoxyben- zoinsulfonsäure, das man durch Sulfönierung des ms-Octodecyl-p-methyl-desoxybenzoins und Neutralisierung der entstandenen Sulfon- säure erhält.
Die neue Verbindung wird als helles Pul ver erhalten, das in Wasser lehr leicht lös lich ist und dessen Lösungen Zelluloseregene- raten und nativenZellulosenvorzüglicbeWeich- heit verleihen; wertvoll ist dabei die Eigen schaft der neuen Verbindung, Farbstofflösun- gen unbeein$usst zu lassen, so dass ihre Au- weudung im Färbebad erfolgen kann.
Beispiel: In 40 Teile Monohydrat werden, unter Rühren bei<B>10'</B> C 20 Teile ms-Octodecyl-p- rnethyl - desogybenzoin eingetragen, darauf langsam bei 0-5 C 40 Teile Oleum (26 /oig) zugetropft. Nach vierstündigem Rühren unter 10 o C erweist sich eine in Wasser gegebene Probe vollständig löslich. Sobald dies der Fall ist, wird die Reaktionsmasse auf Eis gegos sen, die ausgeschiedene freie Sulfonsäure ab getrennt und durch Zusatz von Natronlauge neutralisiert.
Durch Eindampfen gewinnt man das Natronsalz als helles Pulver, das in Was ser sehr leicht löslich ist und dessen Lösun gen Zelluloseregeneraten und nativen Zellu losen vorzügliche Weichheit verleihen.
Process for the preparation of a water-soluble aromatic series compound. It has been found that new, water-soluble derivatives of the aromatic series are obtained if compounds of the following schematic structure are used
EMI0001.0002
where Ar is understood to mean aromatic radicals, g in the ms position denotes an aliphatic or alicyclic substituent with more than 5 carbon atoms and the free positions of the aromatic nuclei can be substituted as desired, but primarily by organic radicals,
treated with sulfonating agents.
The deoxybenzoins substituted in the ms position by aliphatic or alicyelic groups with more than 5 carbon aromas are suitable as starting materials for the sulfonation. These compounds, some of which are new, can easily be obtained using known processes (see, for example, Ber. D. Deut- see Chem. Gesellschaft Vol. 21, page 1299 and Vol. 25, page 2239.
The bodies obtained after the sulfation of these substituted deoxybenzoins are valuable wetting agents, dispersing agents and emulsifying agents in the form of their soluble metal salts, and their softening effect is of particular interest.
The subject of the present patent is a process for the preparation of the sodium salt of ms-octodecyl-p-methyl-deoxybenzoinsulfonic acid, which is obtained by sulfonating ms-octodecyl-p-methyl-deoxybenzoins and neutralizing the sulfonic acid formed.
The new compound is obtained as a pale powder which is very easily soluble in water and whose solutions give cellulose regenerates and native cellulose excellent softness; What is valuable here is the property of the new compound of leaving dye solutions unaffected so that they can be thickened in the dye bath.
Example: 20 parts of ms-octodecyl-p-methyl-desogybenzoin are introduced into 40 parts of monohydrate with stirring at 10 ° C., then 40 parts of oleum (26%) are slowly added dropwise at 0-5 ° C. . After four hours of stirring below 10 o C, a sample placed in water proves to be completely soluble. As soon as this is the case, the reaction mass is poured onto ice, the precipitated free sulfonic acid is separated off and neutralized by adding sodium hydroxide solution.
The sodium salt is obtained as a pale powder by evaporation, which is very easily soluble in water and whose solutions give regenerated cellulose and native cellulose excellent softness.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH198705T | 1937-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH198705A true CH198705A (en) | 1938-07-15 |
Family
ID=4441465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH198705D CH198705A (en) | 1937-05-29 | 1937-05-29 | Process for the preparation of a water-soluble aromatic series compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH198705A (en) |
-
1937
- 1937-05-29 CH CH198705D patent/CH198705A/en unknown
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