CH155994A - Process for the production of a new ester mixture that is valuable as an auxiliary for the textile industry. - Google Patents
Process for the production of a new ester mixture that is valuable as an auxiliary for the textile industry.Info
- Publication number
- CH155994A CH155994A CH155994DA CH155994A CH 155994 A CH155994 A CH 155994A CH 155994D A CH155994D A CH 155994DA CH 155994 A CH155994 A CH 155994A
- Authority
- CH
- Switzerland
- Prior art keywords
- valuable
- auxiliary
- production
- textile industry
- ester mixture
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 title claims description 10
- 239000004753 textile Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- QJGQOJGPZZZZIZ-UHFFFAOYSA-N 3-sulfonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(S(O)(=O)=O)=CC2=C1 QJGQOJGPZZZZIZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 238000009736 wetting Methods 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 230000001804 emulsifying effect Effects 0.000 claims description 2
- -1 diamylcarboxylic acid ester Chemical class 0.000 claims 1
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- ZXWFVMHYBGMBTG-UHFFFAOYSA-N 4-(3-sulfonaphthalene-1-carbonyl)oxycarbonylnaphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC(C(=O)OC(=O)C=3C4=CC=CC=C4C=C(C=3)S(O)(=O)=O)=C21 ZXWFVMHYBGMBTG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-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
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
- C07C309/58—Carboxylic acid groups or esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Description
Verfahren zur Herstellung eines neuen, als Hilfsmittel für die Textilindustrie wertvollen Estergemisches. Es wurde gefunden; dass man ein neues, als Hilfsmittel für die Textilindustrie wert volles, aus dem Mono- und Diamyloarbon- säureester bestehendes, Estergemisch erhält, wenn man 3-Sulfonaphthalsäure oder ein solches Derivat derselben, das durch Beband- lung mit einem Alkohol in einen Ester der 3-Sulfonaphthalsäure übergehen kann,
wie das Anhydrid oder die Halogenide dieser Säure, mit Gährungsamylalkohol behandelt.
Zur Veresterung kann man beispielsweise 3-Sulfonaphthalsäure, bezw. deren Anhydrid oder Chlorid oder Salze mit Gährungsamyl- alkohol, erhitzen, gegebenenfalls unter Zu satz von Ohlorwasserstoffgas, konzentrierter Schwefelsäure oder anderer, die Veresterung beschleunigender Mittel.;;
, Die Veresterung wird erleichtert, wenn man das bei der Reak tion sich bildende Wasser aus dem Ver- esterungsgemisch in bekannter Weise ent fernt, beispielsweise mit Hilfe solcher Stoffe, die mit Wasser azeotrope Mischungen bilden. Statt von den Säurechloriden auszugehen kann man dieselben auch erst während der Veresterung entstehen lassen, zum Beispiel unter Anwendung von Phosphoroxychlorid und dergleichen.
Der zu veresternde (äährungsamylalkohol braucht weder in hochprozentigem noch in wasserfreiem Zustande zur Anwendung zu gelangen, man kann zum Beispiel von h'uselöl oder Sulfitspritfuselöl ausgehen. Man kann auch einen solchen Amylalkohol verwenden, der mindestens einen Hauptbestandteil des GährungsamylalkoholsinüberwiegenderMenge enthält, zum Beispiel Isoamylalkohol.
Das neue Estergemisch stellt nach dem Neutralisieren und Trocknen ein graues Pul ver dar, das in Wasser leicht löslich ist und ein ausgesprochenes Netz-, Reinigungs- und Emulgierungsvermögen besitzt. Das Ester gemisch kann daher für die mannigfaltigsten industriellen Zwecke Verwendung finden. <I>Beispiel:</I> 5,6 .
Gewichtsteile 3 - Sulfonaphthalsäure- anhydrid werden mit 21 Gewichtsteilen Gährungsamylalkohol (Siedepunkt 128-132o C), welcher 3 % Salzsäuregas enthält, etwa 15 Minuten zum schwachen Sieden erhitzt. Man destilliert den überschüssig angewendeten Amylalkohol ab, was zweckmässig unter ver mindertem Druck erfolgt, und nimmt den öligen Rückstand in Wasser auf.
Nach dem Neutralisieren dampft man zur Trockne zweckmässig unter vermindertem Druck, wo bei man ein graues Pulver erhält, das von Wasser zu einer beim Schütteln stark schäu menden Lösung von starkem Netzvermögen aufgenommen wird.
Process for the production of a new ester mixture that is valuable as an auxiliary for the textile industry It was found; that a new mixture of esters consisting of the mono- and diamyloarboxylic acid esters, valuable as an aid for the textile industry, is obtained if 3-sulfonaphthalic acid or such a derivative thereof is converted into an ester of the 3 rd class by treatment with an alcohol -Sulfonaphthalic acid can pass over,
like the anhydride or halides of this acid, treated with fermentation amyl alcohol.
For esterification, for example, 3-sulfonaphthalic acid, respectively. Heat their anhydride or chloride or salts with fermentation amyl alcohol, if necessary with the addition of hydrogen chloride gas, concentrated sulfuric acid or other agents which accelerate the esterification. ;;
The esterification is facilitated if the water formed in the reaction is removed from the esterification mixture in a known manner, for example with the aid of substances which form azeotropic mixtures with water. Instead of starting from the acid chlorides, they can also only be formed during the esterification, for example using phosphorus oxychloride and the like.
The nutritional amyl alcohol to be esterified does not need to be used in either a highly concentrated or anhydrous state, one can, for example, start from h'usel oil or sulphite fuel oil. One can also use an amyl alcohol that contains at least one main component of the fermentation amyl alcohol in a predominant amount, for example isoamyl alcohol.
After neutralization and drying, the new ester mixture is a gray powder that is easily soluble in water and has excellent wetting, cleaning and emulsifying properties. The ester mixture can therefore be used for a wide variety of industrial purposes. <I> Example: </I> 5.6.
Parts by weight of 3-sulfonaphthalic anhydride are heated to a gentle boil for about 15 minutes with 21 parts by weight of fermentation amyl alcohol (boiling point 128-132o C), which contains 3% hydrochloric acid gas. The excess amyl alcohol used is distilled off, which is advantageously carried out under reduced pressure, and the oily residue is taken up in water.
After neutralization, it is evaporated to dryness, expediently under reduced pressure, where a gray powder is obtained which is absorbed by water to form a strongly foaming solution of strong wetting power when shaken.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH153479T | 1930-03-29 | ||
| CH155994T | 1930-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH155994A true CH155994A (en) | 1932-07-15 |
Family
ID=25716199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH155994D CH155994A (en) | 1930-03-29 | 1930-03-29 | Process for the production of a new ester mixture that is valuable as an auxiliary for the textile industry. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH155994A (en) |
-
1930
- 1930-03-29 CH CH155994D patent/CH155994A/en unknown
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