CH199086A - Process for the preparation of a new ester. - Google Patents
Process for the preparation of a new ester.Info
- Publication number
- CH199086A CH199086A CH199086DA CH199086A CH 199086 A CH199086 A CH 199086A CH 199086D A CH199086D A CH 199086DA CH 199086 A CH199086 A CH 199086A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- new ester
- ester
- disulfophthalic
- preparation
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- UOLRYOJSDBGNMC-UHFFFAOYSA-N 3,5-disulfophthalic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1C(O)=O UOLRYOJSDBGNMC-UHFFFAOYSA-N 0.000 claims description 4
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 4
- 244000060011 Cocos nucifera Species 0.000 claims description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 238000005187 foaming Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MPVPVYVSKMRUGT-UHFFFAOYSA-N 1,3-dioxo-2-benzofuran-4,6-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(=O)(=O)O)=CC2=C1C(=O)OC2=O MPVPVYVSKMRUGT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting 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
- 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)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Description
Verfahren zur Herstellung eines neuen Esters. Es wurde gefunden, dass man einen neuen Ester erhält, wenn man 3,5-Disulfophthal- säure oder ein solches Derivat derselben, das durch Behandeln mit einem Alkohol in einen Carbonsäureester der 3,5-Disulfophthalsäure übergehen kann, mit Kokosfettsäure-N-oxy- äthylamid zu einem Carbonsäuremonoester umsetzt.
Die Veresterung der Carboxylgruppe kann zum Beispiel durch Erhitzen der freien Sulfonsäure bezw. von ,deren Salzen mit dem gokosfettsäure-N-oxyäthylamid erfolgen, ge gebenenfalls in Gegenwart von Lösungsmit teln, wie Pyridin, Chinolin, Dimethyl-p-to- luidin und dergleichen.
Besonders leicht rea giert das Carbonsäureanhydrid oder -chlorid. Carbonsäureester - der 3,5-Disulfophthalsäure lassen sich mit dem Kokosfettsäure-N-oxy- äthylamid umestern. Bei der Veresterung können konzentrierte Schwefelsäure, Chlor wasserstoffgas oder andere, die Veresterung beschleunigende Mittel hinzugefügt werden.
Die Veresterung wird erleichtert, wenn man das bei der Reaktion sich bildende Wasser aus dem Veresterungsgemisch in bekannter Weise entfernt, beispielsweise mit Hilfe sol cher Stoffe, die mit Wasser azeotrope Mi schungen bilden. Das abgespaltene Wasser kann auch durch Arbeiten unter verminder tem Druck entfernt werden.
Der neue Ester stellt nach dem Neutrali sieren und Trocknen eine feste, pulverisier- bare blasse dar, die von Wasser leicht zu einer beim Schütteln stark schäumenden Lö sung aufgenommen wird.
Der gemäss vorliegendem Verfahren her zustellende Ester kann dank seiner kapillar- aktiven Eigenschaften beispielsweise als Netz-, Reinigungs-, Wasch-, Dispergier-, Egalisier- und Weichmachungsmittel, insbe sondere als Schaummittel, z. B. für Feuer- löschzwecke, oder als Waschmittel für leben des Haar Verwendung finden. Der neue Ester kann allein oder zusammen mit andern geeigneten Stoffen, wie Lösungsmitteln, Sal zen ein- oder mehrwertiger Metalle, Seifen oder seifenartigen Stoffen oder Schutzkol loiden Anwendung finden.
Beispiel: 3.5 Gewichtsteile geschmolzenes Kokos- fettsäure-N-oxyäthylamid von etwa 75 bis 80 C werden bei 70 bis 90 unter Rühren allmählich in 5 Gewichtsteile 3,5-Disulfo- phthalsäureanhydrid eingetragen. Man rührt kurze Geit nach, löst nach dem Erkalten in Wasser und neutralisiert mit konzentrierter Kaliumhydroxydlösung. Nach dem Trock nen erhält man eine feste pulverisierbare Masse, die von Wasser leicht zu stark schäu menden Lösungen aufgenommen wird.
Process for the preparation of a new ester. It has been found that a new ester is obtained when 3,5-disulfophthalic acid or such a derivative thereof, which can be converted into a carboxylic acid ester of 3,5-disulfophthalic acid by treatment with an alcohol, with coconut fatty acid-N-oxy - Ethylamide is converted into a carboxylic acid monoester.
The esterification of the carboxyl group can bezw, for example, by heating the free sulfonic acid. of, the salts of which are carried out with the gokosfettsäure-N-oxyäthylamid, if necessary in the presence of solvents, such as pyridine, quinoline, dimethyl-p-toluidine and the like.
The carboxylic acid anhydride or chloride reacts particularly easily. Carboxylic acid esters - 3,5-disulfophthalic acid can be transesterified with coconut fatty acid-N-oxyethylamide. During the esterification, concentrated sulfuric acid, hydrogen chloride gas or other agents which accelerate the esterification can be added.
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 sol cher substances which form azeotropic mixtures with water. The separated water can also be removed by working under reduced pressure.
After neutralization and drying, the new ester is a solid, pulverizable pale that is easily absorbed by water to form a strongly foaming solution when shaken.
The ester to be produced according to the present process can, thanks to its capillary-active properties, for example, as a wetting, cleaning, washing, dispersing, leveling and softening agent, in particular as a foaming agent, e.g. B. for fire extinguishing purposes, or as a detergent for the life of the hair use. The new ester can be used alone or together with other suitable substances, such as solvents, salts of monovalent or polyvalent metals, soaps or soap-like substances or protective colloids.
Example: 3.5 parts by weight of molten coconut fatty acid N-oxyethylamide at about 75 to 80 ° C. are gradually introduced into 5 parts by weight of 3,5-disulfophthalic anhydride at 70 to 90 ° C. with stirring. The mixture is stirred for a short time, after cooling it is dissolved in water and neutralized with concentrated potassium hydroxide solution. After the dry, a solid pulverizable mass is obtained, which is easily absorbed by water to form strongly foaming solutions.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH199086T | 1936-10-17 | ||
| CH195948T | 1936-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199086A true CH199086A (en) | 1938-07-31 |
Family
ID=25722812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199086D CH199086A (en) | 1936-10-17 | 1936-10-17 | Process for the preparation of a new ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199086A (en) |
-
1936
- 1936-10-17 CH CH199086D patent/CH199086A/en unknown
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