DE1151500B - Process for the preparation of nonionic, surface-active monocarbamic acid esters of aliphatic polyhydroxy compounds - Google Patents
Process for the preparation of nonionic, surface-active monocarbamic acid esters of aliphatic polyhydroxy compoundsInfo
- Publication number
- DE1151500B DE1151500B DEU4701A DEU0004701A DE1151500B DE 1151500 B DE1151500 B DE 1151500B DE U4701 A DEU4701 A DE U4701A DE U0004701 A DEU0004701 A DE U0004701A DE 1151500 B DE1151500 B DE 1151500B
- Authority
- DE
- Germany
- Prior art keywords
- active
- nonionic
- acid esters
- preparation
- polyhydroxy compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 5
- 239000002253 acid Substances 0.000 title claims description 3
- 125000001931 aliphatic group Chemical group 0.000 title claims description 3
- 150000002148 esters Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- -1 fatty acid esters Chemical class 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 5
- 229930195725 Mannitol Natural products 0.000 description 5
- 239000000594 mannitol Substances 0.000 description 5
- 235000010355 mannitol Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RFXBSYPBSRSQDU-UHFFFAOYSA-N 1-isocyanatoheptane Chemical compound CCCCCCCN=C=O RFXBSYPBSRSQDU-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- DYQFCTCUULUMTQ-UHFFFAOYSA-N 1-isocyanatooctane Chemical compound CCCCCCCCN=C=O DYQFCTCUULUMTQ-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001461 cytolytic effect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von nichtionogenen grenzflächenäktiven Monocarbaminsäureestern von aliphatischen Polyhydroxyverbindungen Die Erfindung bezieht sich auf ein Verfahren zur Herstellung nichtionogener, grenzflächenaktiver, waschaktiver, netzaktiver und emulgierender Verbindungen.Process for the preparation of nonionic, surface-active monocarbamic acid esters of aliphatic polyhydroxy compounds The invention relates to a method for the production of non-ionic, surface-active, washing-active, wetting-active and emulsifying compounds.
Es ist bekannt, daß die Häufung wasserlöslichmachender OH-Gruppen bei der Synthese nichtionogener, oberflächenaktiver Verbindungen genutzt wird. Zu den bekanntesten und bisher meist verwendeten nichtionogenen, grenzflächenaktiven Verbindungen zählen die Fettsäureester des Sorbits und Mannits. Weiterhin werden bei der partiellen Veresterung der Saccharose mit höhermolekularen Fettsäuren, je nach Wahl der Molverhältnisse, Mono-und Diester gewonnen. Auch sind oberflächenaktive N-Alkyl-carbaminsäureester von Dioxyalkylverbindungen bekanntgeworden.It is known that the accumulation of water-solubilizing OH groups is used in the synthesis of nonionic, surface-active compounds. to the best known and so far most used non-ionic, surface-active Compounds include the fatty acid esters of sorbitol and mannitol. Continue to be in the partial esterification of sucrose with higher molecular weight fatty acids, each obtained according to the choice of molar ratios, mono- and diesters. They are also surface-active N-alkyl-carbamic acid esters of dioxyalkyl compounds become known.
Es wurde gefunden, daß Polyhydroxylverbindungen, wie Glycerin, Erythrit,
Xylit, Sorbit, Dulcit, Mannit, Pentaerythrit, Dipentaerythrit, gegebenenfalls stickstoffhaltige
Polyhydroxylverbindungen, wie Triäthanolamin, mit Alkylisocyanaten mit mehr als
5 C-Atomen in der Kette gemäß nachstehender Formulierung reagieren,
Die erfindungsgemäßen Verbindungen zeichnen sich durch starke Reinigungskraft, Schaumvermögen, hämolytische und cytolytische Wirksamkeit aus.The compounds according to the invention are distinguished by their strong cleaning power, Foaming power, hemolytic and cytolytic effectiveness.
Vergleichende analytische Untersuchungen von N - n - Octyl - carbaminsäure - mannit - ester -1 mit N-Mono-cyclohexyl-carbaminsäure-glykolesterhaben zu folgenden Resultaten geführt: Oberflächenspannung, dyn/cm, 20° (Ringabreißmethode, Lecompte du Nouy) N-n-Octyl-carbaminsäure-mannit-ester-1 0,1 g/100 ccm dest. H20 . . . . . . . . . . . . . . . . 39 N-Mono-cyclohexyl-carbaminsäure-glykolester 0,1 g/100 ccm dest. H20 . . . . . . . . . . . . . . . . 51 Reinigungskraft (Konzentration der Flotte 0,5%, Helligkeit bezogen auf MgO = 100, Mittelwerte aus vier Messungen) N-n-Octyl-carbaminsäure-mannit-ester-1 ...... 10 N-Mono-cyclohexyl-carbaminsäure-glykolester 7 Beispiel 1 a-n-Heptyl-carbaminsäure-glycerinester CHs - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - NH - CO - O - CH2 - CH(OH) - CH2(OH) Zu etwa 3 Mol Glycerin wird 1 Mol n-Heptylisocyanat unter Rückfluß bei 150°C und Wasserausschluß zugetropft. Das erkaltete, teilweise erstarrte Reaktionsprodukt wird in kochendem Wasser aufgenommen und kristallisiert nach dem Erkalten aus der wäßrigen Lösung. Aus Äther umkristallisiert, beginnt der reine a-n-Heptyl-carbaminsäure-glycerinester bei 53'C zu schmelzen und ist erst bei 58'C restlos durchgeschmolzen. Ausbeute, bezogen auf Isocyanat, 95% der Theorie. Beispiel 2 Mono-n-heptyl-carbaminsäure-triäthanolaminester Zu etwa 3 Mol Triäthanolamin läßt man unter Rückfluß bei 150°C und Wasserausschluß 1 Mol n-Heptylisocyanat zutropfen. Die Aufarbeitung des Reaktionsgemisches erfolgt zwecks Isolierung des Mono-n-heptyl-carbaminsäure-triäthanolaminesters in ähnlicher Weise wie im Beispiel 1. Hochviskose Flüssigkeit. Ausbeute, bezogen auf Isocyanat, 95% der Theorie. Beispiel 3 N-n-Octyl-carbaminsäure-mannit-ester-1 73 g = 4/1o Mol Mannit werden in 300 ccm Dimethylformamid heiß gelöst. Danach läßt man bei 150°C langsam 15,5 g = 1/1o Mol n-Octylisocyanat zutropfen. Man hält die Temperatur 3 Stunden lang und läßt dann abkühlen. Dabei scheidet sich der Überschuß des Mannits ab. Er wird abfiltriert und das Filtrat im Vakuum eingedampft. Der Rückstand wird in heißem Wasser gelöst. Bdim Abkühlen erhält ma^ eine Gallerte, die nach Abtrennung des überschüssigen Wassers aus Äthanol umkristallisiert werden kann. Man erhält ein Produkt vom Schmelzpunkt 151,5 bis 153,5°C. Ausbeute 700% der Theorie.Comparative analytical investigations of N - n - octyl - carbamic acid - mannitol - ester -1 with N-mono-cyclohexyl-carbamic acid-glycol ester have led to the following results: surface tension, dyn / cm, 20 ° (ring tearing method, Lecompte du Nouy) Nn-octyl -carbamic acid mannitol ester-1 0.1 g / 100 ccm dist. H20. . . . . . . . . . . . . . . . 39 N-Mono-cyclohexyl-carbamic acid glycol ester 0.1 g / 100 ccm dist. H20. . . . . . . . . . . . . . . . 51 Cleaning power (concentration of the liquor 0.5%, brightness based on MgO = 100, mean values from four measurements) Nn-octyl-carbamic acid-mannitol-ester-1 ...... 10 N-mono-cyclohexyl-carbamic acid-glycol ester 7 Example 1 an-heptyl-carbamic acid glycerol ester CHs - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - NH - CO - O - CH2 - CH (OH) - CH2 (OH) 1 mole of n Heptyl isocyanate was added dropwise under reflux at 150 ° C. with exclusion of water. The cooled, partially solidified reaction product is taken up in boiling water and crystallizes from the aqueous solution after cooling. Recrystallized from ether, the pure an-heptyl-carbamic acid-glycerol ester begins to melt at 53'C and is only completely melted at 58'C. Yield, based on isocyanate, 95% of theory. Example 2 Mono-n-heptyl-carbamic acid triethanolamine ester 1 mole of n-heptyl isocyanate is added dropwise to about 3 moles of triethanolamine under reflux at 150 ° C. with exclusion of water. The reaction mixture is worked up to isolate the mono-n-heptyl-carbamic acid triethanolamine ester in a manner similar to that in Example 1. Highly viscous liquid. Yield, based on isocyanate, 95% of theory. Example 3 Nn-Octyl-carbamic acid-mannitol-ester-1 73 g = 4/10 mol of mannitol are dissolved in 300 ccm of dimethylformamide while hot. Thereafter, 15.5 g = 1/10 mol of n-octyl isocyanate are slowly added dropwise at 150.degree. The temperature is held for 3 hours and then allowed to cool. The excess of mannitol separates out. It is filtered off and the filtrate is evaporated in vacuo. The residue is dissolved in hot water. After cooling, a jelly is obtained which, after the excess water has been separated off, can be recrystallized from ethanol. A product with a melting point of 151.5 to 153.5 ° C. is obtained. Yield 700% of theory.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEU4701A DE1151500B (en) | 1957-08-05 | 1957-08-05 | Process for the preparation of nonionic, surface-active monocarbamic acid esters of aliphatic polyhydroxy compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEU4701A DE1151500B (en) | 1957-08-05 | 1957-08-05 | Process for the preparation of nonionic, surface-active monocarbamic acid esters of aliphatic polyhydroxy compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1151500B true DE1151500B (en) | 1963-07-18 |
Family
ID=7565562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEU4701A Pending DE1151500B (en) | 1957-08-05 | 1957-08-05 | Process for the preparation of nonionic, surface-active monocarbamic acid esters of aliphatic polyhydroxy compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1151500B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002083626A2 (en) * | 2001-04-11 | 2002-10-24 | Cognis Deutschland Gmbh & Co. Kg | Alkyl and/or alkenyl glycerol carbamates |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE552758C (en) * | 1930-12-28 | 1932-06-28 | I G Farbenindustrie Akt Ges | Process for the production of wetting, cleaning and dispersing agents |
| GB689705A (en) * | 1950-09-15 | 1953-04-01 | Saint Gobain | Glycol carbamates and processes for the manufacture thereof |
| DE949947C (en) * | 1953-03-04 | 1956-09-27 | Hoechst Ag | Process for the preparation of basic bis-N-phenyl urethanes |
-
1957
- 1957-08-05 DE DEU4701A patent/DE1151500B/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE552758C (en) * | 1930-12-28 | 1932-06-28 | I G Farbenindustrie Akt Ges | Process for the production of wetting, cleaning and dispersing agents |
| GB689705A (en) * | 1950-09-15 | 1953-04-01 | Saint Gobain | Glycol carbamates and processes for the manufacture thereof |
| DE949947C (en) * | 1953-03-04 | 1956-09-27 | Hoechst Ag | Process for the preparation of basic bis-N-phenyl urethanes |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002083626A2 (en) * | 2001-04-11 | 2002-10-24 | Cognis Deutschland Gmbh & Co. Kg | Alkyl and/or alkenyl glycerol carbamates |
| WO2002083626A3 (en) * | 2001-04-11 | 2003-12-04 | Cognis Deutschland Gmbh | Alkyl and/or alkenyl glycerol carbamates |
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