CH277196A - Process for the production of a new partial ester of a polybasic sulfide carboxylic acid. - Google Patents
Process for the production of a new partial ester of a polybasic sulfide carboxylic acid.Info
- Publication number
- CH277196A CH277196A CH277196DA CH277196A CH 277196 A CH277196 A CH 277196A CH 277196D A CH277196D A CH 277196DA CH 277196 A CH277196 A CH 277196A
- Authority
- CH
- Switzerland
- Prior art keywords
- partial ester
- new partial
- reaction
- polybasic
- production
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 10
- -1 sulfide carboxylic acid Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 3
- 238000005187 foaming Methods 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 239000004902 Softening Agent Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- WNKQDGLSQUASME-UHFFFAOYSA-N 4-sulfophthalic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1C(O)=O WNKQDGLSQUASME-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001704 evaporation Methods 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
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Verfahren zur Herstellung eines neuen Teilesters einer mehrbasiseben Sulfidearbonsäure. Es wurde gefunden, da.ss man zu einem neuen Teilester einer mehrbasischen Sulfid- carbonsäure gelangt, wenn man Thioglykol- säure mit dem Diester aus Maleinsäure und N-(ss-Oxy-äthyl)-stearinsäureamid und N-(ss- Oxy-äthyl) -palmitinsäureamid umsetzt.
Der neue Teilester entspricht der Formel Die Reaktion kann vorteilhaft in Gegen wart von die Umsetzung beschleunigenden Stoffen und von Lösungsmitteln vorgenom men werden. Dabei tritt eine Addition der Mercaptocarbonsäure an die Lückenbindung des ungesättigten Esters ein.
EMI0001.0018
worin R-C0 den Acylrest der Stearin- bzw. Palmitinsäure bedeutet. Die Umsetzung kann z. B. durch Vermischen bei Raum temperatur, vorteilhafter jedoch in der Wärme, beispielsweise bei 50-100 , vorgenom men werden.
Es kann dabei zweckmässig sein, kleine Mengen von die Umsetzung beschleu nigenden Stoffen, insbesondere von solchen mit alkalischer Reaktion, wie Alkalihy- droxvden, Alkalialkoholaten, organischen Ba sen, z. B. Piperidin, zuzufügen. Falls an Stelle der Mercaptosäure ihre Salze zur Um setzung herangezogen werden, ist es zweck mässig, in Gegenwart eines Lösungsmittels, z. B. unter Zusatz von Alkoholen oder deren Mischungen mit. Wasser, zu arbeiten.
Das Natriumsalz des neuen Teilesters kann als Textilhilfsstoff, z. B. als sehr wirk- saines Weichmachungsmittel für Cellulose- fasern oder für Wolle, verwendet werden; es bildet eine feste Masse, die von heissem Wasser zu einer praktisch klaren, schäumen den Lösung aufgenommen wird. Es kann allein oder zusammen mit andern bei der Ver wendung von Textilhilfsmitteln üblichen Stoffen, z.
B. gemeinsam mit Salzen oder kalkbeständigen Dispergiermitteln, wie mit Salzen von sulfonierten, am 2-Kohlenstoff- atom durch höhere Alkylreste substituierten Benzimidazolen, ferner von hIonocarbonsäure- estern der 4-Sulfophthalsäure mit höheren Fettalkoholen,
weiterhin gemeinsam mit Fett- alkoholsulfonaten oder Kondensationsproduk ten von höheren Fettsäuren mit aliphatischen Oxy- oder Aminosäuren verwendet werden.
Besonders geeignet ist z. B. eine Mischung aus 70 Teilen des Natriumsalzes des neuen Teilesters mit 30 Teilen Dinatriumsalz der N-Benzyl-,u-heptadecy 1-benzimidazol-@disulfon- säure.
Im nachfolgenden Beispiel bedeuten Teile, falls nichts anderes bemerkt wird, Gewichts teile. Das Verhältnis von Gewichtsteilen zu Volumteilen ist. das -leielie wie dasjenige zwischen dem Kilogramm und dem Liter.
Beispiel: 2,2 Teile Thioglykolsäure und 1.4,1 Teile Diester aus Maleinsäure und N=(fl-Oxy- äthyl)-stearinsäiireamid, bergestellt aus techn. Stearinsäure, werden unter Ausschluss von Sauerstoff auf 70=75 erwärmt, bis eine mit Natriumhy droxy d neutralisierte Probe in Wasser praktisch klar löslich ist.
Das aus dem Umsetzungsprodukt durch Lösen in Alkohol, Neutralisieren mit Natriumhydro xydlösung und Eindampfen zur Trockne erhältliche Na triumsalz der Formel
EMI0002.0034
worin R-C/0 den Acylrest der Stea.rin- bzw. Palmitinsäure bedeutet, bildet eine feste, pulverisierbare Masse, die von heissem Wasser zu einer praktisch klaren, schäumenden Lö sung aufgenommen wird.
Der als Ausgangsprodukt verwendete Ma leinsäureester kann wie folgt hergestellt wer den: 9,8 Teile Maleinsäureanhydrid und<B>65</B> Teile N-(l Oxy-äthyl)-stearinsäureamid und N-(l-Oxy-äthyl) -palmitinsäureamid werden unter Rühren während 3 Stunden im sieden den Wasserbad erhitzt. Darauf fügt man 50 Teile Benzol und 0,4 Volumteile konz. Schwe felsäure hinzu und erhitzt zum Sieden des Benzols, bis kein Wasser mehr abgespalten wird.
Das aus dem Rückflusskühler ab fliessende Destillat lässt man über einen in bekannter Weise konstruierten Wasserfänger in das Reaktionsgefäss zurückfliessen. Auf diese Weise kann das bei der Veresterung ab- gespaltene Wasser aus dem Reaktionsgemisch entfernt werden. Nach beendigter Vereste- rung wird das Umsetzungsäut neutralisiert und das Benzol abdestilliert.
Das Natriumsalz des neuen Esters kann als Weichmachungsmittel für Cellulosefasern oder für Wolle verwendet werden.
Process for the preparation of a new partial ester of a multibasic sulfidearboxylic acid. It has been found that a new partial ester of a polybasic sulfide carboxylic acid is obtained if thioglycolic acid is mixed with the diester of maleic acid and N- (ß-oxy-ethyl) -stearic acid amide and N- (ß-oxy-ethyl ) -palmitic acid amide.
The new partial ester corresponds to the formula The reaction can advantageously be carried out in the presence of substances that accelerate the conversion and of solvents. In this case, the mercaptocarboxylic acid is added to the gap bond of the unsaturated ester.
EMI0001.0018
where R-C0 denotes the acyl radical of stearic or palmitic acid. The implementation can e.g. B. by mixing at room temperature, but more advantageous in the heat, for example at 50-100, vorgenom men.
It may be useful to use small amounts of substances that accelerate the reaction, especially those with an alkaline reaction, such as alkali hydroxides, alkali alcoholates, organic bases, e.g. B. piperidine to add. If, instead of the mercapto acid, their salts are used for the implementation, it is advantageous in the presence of a solvent, eg. B. with the addition of alcohols or mixtures thereof. Water to work.
The sodium salt of the new partial ester can be used as a textile auxiliary, e.g. B. can be used as a very effective softening agent for cellulose fibers or for wool; it forms a solid mass which is absorbed by hot water to form a practically clear, foaming solution. It can be used alone or together with other substances common in the use of textile auxiliaries, eg.
B. together with salts or lime-resistant dispersants, such as salts of sulfonated benzimidazoles substituted on the 2-carbon atom by higher alkyl radicals, and also of monocarboxylic acid esters of 4-sulfophthalic acid with higher fatty alcohols,
continue to be used together with fatty alcohol sulfonates or condensation products of higher fatty acids with aliphatic oxy or amino acids.
Particularly suitable is z. B. a mixture of 70 parts of the sodium salt of the new partial ester with 30 parts of the disodium salt of N-benzyl, u-heptadecy 1-benzimidazole @ disulfonic acid.
In the following example, unless otherwise noted, parts mean parts by weight. The ratio of parts by weight to parts by volume is. everything like that between the kilogram and the liter.
Example: 2.2 parts of thioglycolic acid and 1.4.1 parts of diesters from maleic acid and N = (fl-oxyethyl) stearic acid amide, prepared from techn. Stearic acid are heated to 70 = 75 in the absence of oxygen until a sample neutralized with sodium hydroxide is practically clearly soluble in water.
The sodium salt of the formula obtained from the reaction product by dissolving in alcohol, neutralizing with sodium hydroxide solution and evaporating to dryness
EMI0002.0034
where R-C / 0 denotes the acyl radical of stearic or palmitic acid, forms a solid, pulverizable mass which is absorbed by hot water to form a practically clear, foaming solution.
The maleic acid ester used as the starting product can be prepared as follows: 9.8 parts of maleic anhydride and 65 parts of N- (l-oxyethyl) stearic acid amide and N- (l-oxy-ethyl) palmitic acid amide are heated with stirring for 3 hours in the boiling water bath. Then 50 parts of benzene and 0.4 parts by volume of conc. Add sulfuric acid and heat to the boiling point of the benzene until no more water is split off.
The distillate flowing out of the reflux condenser is allowed to flow back into the reaction vessel via a water trap constructed in a known manner. In this way, the water split off during the esterification can be removed from the reaction mixture. When the esterification is complete, the reaction acid is neutralized and the benzene is distilled off.
The sodium salt of the new ester can be used as a softener for cellulose fibers or for wool.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH277196T | 1948-04-16 | ||
| CH273374T | 1948-04-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH277196A true CH277196A (en) | 1951-08-15 |
Family
ID=25731453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH277196D CH277196A (en) | 1948-04-16 | 1948-04-16 | Process for the production of a new partial ester of a polybasic sulfide carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH277196A (en) |
-
1948
- 1948-04-16 CH CH277196D patent/CH277196A/en unknown
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