CN1145063A - Synthesis of polyhydroxy fatty acid amides from triglycerides - Google Patents
Synthesis of polyhydroxy fatty acid amides from triglycerides Download PDFInfo
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- CN1145063A CN1145063A CN95192460.5A CN95192460A CN1145063A CN 1145063 A CN1145063 A CN 1145063A CN 95192460 A CN95192460 A CN 95192460A CN 1145063 A CN1145063 A CN 1145063A
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- fatty acid
- reaction
- polyhydroxy
- reaction product
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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Abstract
Fats and oils such as hardened palm kernel oil are reacted directly with N-substituted polyhydroxy amines to provide high yields of N-substituted polyhydroxy fatty acid amide surfactants having improved odors and low fatty acid content. Hardened palm kernel oil is reacted with N-methylglucamine in the presence of an ethoxylated alcohol, but in the absence of methanol solvent, using sodium propylene glycolate catalyst to provide the mixed corresponding fatty acid amide of N-methylglucamine.
Description
FIELD OF THE INVENTION
The present invention relates to a kind of preparation method of surfactant for washing.
Related application
This application is that the sequence number of submission on February 17th, 1994 is 08/198,008 part continuation application.
Background of invention
Technical scale synthesis of polyhydroxy fatty acid amides tensio-active agent is considerable.This class nonionic surface active agent is widely used in to be washed and starched and the dishwashing prescription.Polyhydroxy fatty acid amide surfactant has shown removes ability by force to greasy and smeary, to skin and fabric gentleness, and can be produced by non-petrochemicals resource.
The synthetic of polyhydroxy fatty acid amide is not a nothing the matter.This class material is heat-labile, and can generate undesirable band look thing in building-up process.And their undesirably cyclisation of many hydroxyls substituting group generates unwanted by product.In addition, also form some ester-acid amide material.But, these synthetic difficult problems can be solved by adopting alcoholic solvent and suitable selecting catalyst and temperature of reaction usually.These methods are described in United States Patent (USP) U.S.Patent5, in 194,639.
Yet, the preparing in the polyhydroxy fatty acid amide surfactant process prepared reaction product by polyhydroxy amine and fatty acid methyl ester and can be polluted of significant by free fatty acids or " new life " lipid acid.As United States Patent (USP) U.S.Patent5,188,769 is described, and these fatty acid materials can change into their acid amides in other reactions steps.Not generate free fatty acids in the principal reaction product of polyhydroxy fatty acid amide building-up process will be ideal if can manage to make, because the environment of polyhydroxy fatty acid amide smell is concerned about the prescription teacher very much, though very a spot of lipid acid impurity produce smell flavor and also very can detest.
The present invention has determined tri-glyceride, can generate needed polyhydroxy fatty acid amide surfactant with the polyhydroxy amine direct reaction such as those tri-glycerides that constitute natural fats and oils, but in the total reaction product, generate a spot of lipid acid, improving one's methods of this place narration allows the prescription teacher directly to use these grease work, and need not to convert it in advance methyl ester, this will save a lot of times and expense, and United States Patent (USP) U.S.Patent.5,188,769 described lipid acid are removed step and also can be cancelled.Importantly, this improves one's methods and provides high yield production to be suitable for washing and the high quality of other purposes does not have the approach of the polyhydroxy fatty acid amide of smelling.
Technical background
United States Patent (USP) 5,338,487,5,338,486,5,334,764,5,194,639,5,188,769,1,985,424,2,016,962,2,653,932,2,703,798, EPO91917936.6, European patent 558,515,556,348, Japanese publication-Ping-3[1991]-246265 and German Patent 4,235,783 and 4,235,784 all relate to all respects of polyhydroxy fatty acid amide.
Brief summary of the invention
The present invention includes: by fatty acid ester and N-alkyl, a kind of method of N-alkoxyl group or N-aryloxy polyhydroxy amine prepared in reaction polyhydroxy fatty acid amide surfactant reaction product.Its improvement comprises with fatty acid triglyceride as fatty acid ester, in the presence of no monobasic alcoholic solvent, react, fatty acid content in the reaction product is reduced to and is not higher than about 1% of this reaction product weight, generally be not higher than about 0.2%, in addition, this reaction product also will contain the polyhydroxy amine reagent that is low to moderate about 1-4% even is lower than 0.1% weight.In a preferable methods, reaction product will contain and be lower than approximately 0.2%, preferably be lower than the lipid acid of about 0.1% weight and be lower than approximately 0.2%, preferably be lower than the unreacted polyhydroxy amine of about 0.1% weight.
Common alcoholic solvent is not adopted in reaction, and carries out to facilitate reaction with a kind of alcohol alcoxylates (preferably NEODOL) or alkoxylated alkyl phenol.In addition, reaction preferably adopts alkoxide to make catalyzer, and alkoxide is selected from an alkali metal salt of polyvalent alcohol, ethylene glycol, 1 especially, 2-or 1, an alkali metal salt of ammediol or glycerol.
Except as otherwise noted, all percentage, ratio and ratio all refer to weight.The relevant part of all references is all enrolled in this, for your guidance.
The detailed description of invention
The N-alkyl polyhydroxy fatty acid amide surfactant that is made by present method comprises the material of following chemical formula:
The material that N-alkoxyl group that is made by present method or N-aryloxy polyhydroxy fatty acid amide surfactant comprise following chemical formula:
In molecular formula (I) with (II), R
3Be C
5-C
31Alkyl, preferably C
9-C
17Alkyl comprises straight chain and branched-chain alkyl and alkenyl or its mixture; R
1Be C
2-C
8Alkyl comprises straight chain, side chain and cyclisation (containing aryl) alkyl, preferably C
2-C
4Alkylene (alkylene), promptly-CH
2-CH
2-,-CH
2CH
2CH
2-and-CH
2(CH
2)
2CH
2-; R
2Be C
1-C
8Straight chain, side chain and cyclisation alkyl comprise aryl and oxidation alkyl, preferably C
1-C
4Alkyl, particularly methyl and phenyl.In the compound of formula (I), R
4Be typically C
1-C
8Alkyl or hydroxyalkyl comprise methyl (preferably), ethyl, propyl group, sec.-propyl, butyl, amyl group, hexyl, heptyl, octyl group, 2-hydrocarbon ethyl, 3-hydrocarbon propyl group and analogue.Z is the part of hydroxyl alkyl more than, has one and has at least 2 (under the Glycerose situations) or 3 (under other reducing sugar situation) hydroxyls directly are connected to the linear hydrocarbon chain on the chain, or its alkoxy derivative (preferably ethoxylate or propoxylated glycerine).Z is preferably made by the reducing sugar in the reductive amination process; Most preferred Z is the sugar alcohol base section.Suitable reducing sugar comprises: glucose, fructose, maltose, lactose, semi-lactosi, seminose and wood sugar and Glycerose.As a kind of raw material, high dextrorotation cereal syrup, HFCS and high malt sugar cereal syrup and each above-listed sugar all can adopt.These cereal syrup can be made the mixture of the sugar component of Z, but must understand, this does not mean that has got rid of other starting material that are fit to.Z preferably is selected from-CH
2(CHOH)
n-CH
2OH ,-CH (CH
2OH)-(CHOH)
N-1-CH
2OH ,-CH
2-(CHOH)
2-(CHOR ＇) (CHOH)-CH
2OH, n is the integer that comprises 1-5 in addition, R ＇ is H or the monobasic of cyclisation or polybasic carbohydrate and their alkoxy derivative.As pointing out that most preferably n is 4 sugar alcohol base, especially-CH
2-(CHOH)
4-CH
2OH.
In the compound of above-mentioned formula (II), amine substituting group-R
1-O-R
2The indefiniteness example be: for example the 2-methoxy ethyl-, the 3-methoxy-propyl-, 4-methoxyl group butyl-, 5-methoxyl group amyl group-, 6-methoxyl group hexyl-, the 2-ethoxyethyl group-, the 3-ethoxycarbonyl propyl-, the 2-methoxy-propyl-, methoxy-benzyl-, 2-isopropoxy ethyl-, the 3-isopropoxide propyl-, 2-(tert.-butoxy) ethyl-, 3-(tert.-butoxy) propyl group-, 2-(isobutoxy) ethyl-, 3-(isobutoxy) propyl group-, 3-butoxy propyl group-, the 2-butoxyethyl group-, 2-phenoxy group ethyl-, the methoxyl group cyclohexyl-, the methoxyl group cyclohexyl methyl-, the tetrahydrochysene glycosyl-, tetrahydropyrans oxo ethyl-, the 3-[2-methoxy ethoxy] propyl group-, the 2-[2-methoxy ethoxy] ethyl-, the 3-[3-methoxy propoxy] propyl group-, the 2-[3-methoxy propoxy] ethyl-, 3-[methoxyl group polyethyleneoxy] propyl group-, 3-[4-methoxyl group butoxy] propyl group-, 3-[2-methoxyl group isopropoxy] propyl group-, CH
3O-CH
2CH (CH
3)-and CH
3OCH
2CH (CH
3) CH
2-O-(CH
2)
3-.
In above-mentioned formula (I) and compound (II), R
3-CO-N＜can be: for example coconut monoethanolamide, stearic amide, amine hydroxybenzene, lauric amide, tetradecanoic acid acid amides, capric acid acidamide, Palmiticacid acid amides, tallow acid amides etc.
As comprehensive narration, the improvement synthetic method of these tensio-active agents comprises corresponding N-replacement polyhydroxy amine and fatty acid triglyceride is existed but the most handy second hydroxylation alcohol at no monobasic alcoholic solvent, as NEODOL, adopt a kind of alkoxide catalysis of particular type, under about 50-140 ℃ temperature, react with batch mode, obtain the high yield of 90-98%.Product not only has the low levels lipid acid of hope, and has (preferably the being lower than 1%) esteramides and the cyclisation by product of low levels, and has improved color and colour stability, and for example: the Gardner colour code is lower than about 4, between the preferred 0-2.To continuous mode production, used temperature can reach about 180 ℃.If need, can remain in any unreacted polyhydroxy amine in the product by the acid anhydrides acidylate.Acid anhydrides can be used for example diacetyl oxide, maleic anhydride (MALEIC ANHYDRIDE) or analogue, and acidylate in 50-80 ℃ water is to reduce this class residual amine total amount in the product as far as possible.But the advantage of present method is that unreacted polyhydroxy amine can be low to moderate 0.1% in final product, and therefore, this additional step often can.
As if " cyclisation by product " herein is meant the byproduct of reaction in undesirable those initial reaction, and wherein the poly-hydroxy group in the polyhydroxy fatty acid amide can form ring texture.Technician in the chemical field knows, use disaccharide and more high-grade carbohydrate (as maltose) prepare herein polyhydroxy fatty acid amide, the result will form its line style substituting group Z (containing the poly-hydroxy substituting group) naturally by the polyhydroxy fatty acid amide of poly-hydroxy ring structure " end-blocking ", and these materials are not defined herein cyclisation by products.
If want to improve the water-soluble of solid polyhydroxy fatty acid amide surfactant, its melt can be handled by quench.If do not want to be limited by theory, seem this quick cooling to make melt be solidified into metastable solid again, it has higher water-soluble than the polyhydroxy fatty acid amide of pure crystalline form.Cooling (quench) can adopt any method easily to finish fast, as using cooling roller (0-10 ℃); With melt cold surface such as cold steel plate on curtain coating; Or it is medium that the refrigeration coil pipe is immersed melt.This additional processing step is particularly useful in N-alkoxyl group polyhydroxy fatty acid amide.But the application of aforesaid method also is not limited thereto.
In tri-glyceride reagent-present method used tri-glyceride can be any known grease, use as food as those routines or use as fatty acid source.The example of indefiniteness comprises: CRISCO
Oil; Plam oil; High oleoyl Trisun Oil R 80 and high euricic rape seed oil; Palm-kernel oil; Semen Maydis oil; Oleum gossypii seminis; Soybean oil; Tallow; Lard; Canola oil; Rape seed oil; Peanut oil; Tung oil; Sweet oil; Pilchardine; Oleum Cocois; Viscotrol C; Oleum Helianthi; Palm oil fatty acid methyl ester oil; With corresponding " hardened " is hydrogenated oils.If need, can pass through stripping, vacuum distilling, handle with gac or " Fuller's earth " (diatomite), or cold temper, will hang down molecule and volatile matter by removing in the oil, further reduce with the stench by product in the tensio-active agent of present method preparation.
Used N-alkyl, N-alkoxyl group or N-aryloxy polyhydroxy amine all can be buied on market in polyhydroxy amine reagent-present method that N-replaces, also can in the presence of hydrogen and nickel catalyzator, react typically and make by corresponding N-replacement amine and reducing sugar, disclosed as this area.The indefiniteness example of this class material comprises: N-methylglucosamine (preferably); N-(3-methoxycarbonyl propyl) glycosamine; N-(2-methoxyethyl) glycosamine; N-propyl group glycosamine; N-butyl Fructus Hordei Germinatus amine; N-hexyl glycosamine and analogue thereof.
Catalyzer-preferred herein catalyzer is an alkali metal salt with polyvalent alcohol of at least 2 hydroxyls, and sodium, potassium or lithium salts all can adopt (particular certain cancers).An alkali metal salt of monohydroxy-alcohol (as: sterically hindered monohydroxy-alcohol also is preferential the selection as sodium tert-butoxide etc. for sodium methylate, sodium ethylate) also can adopt, but is not preferential the selection, because might generate the short chain methyl ester and the analogue of foul smell.On the contrary, having found to use the polyhydric alcohol an alkali metal salt is favourable to avoid this problem.The non-limiting example of this class catalyzer commonly used comprises: ethylene glycol sodium; Glycerol sodium and propylene glycol salt, as propylene glycol sodium (1,3-and 1,2-propylene glycol sodium all can adopt; 1, the 2-isomer is preferred) and the 2-methyl isophthalic acid, ammediol salt, the sodium salt of NEODOL-type ethoxylated alcohol also can adopt.
Reaction medium-this reaction is not preferably carried out in the presence of monohydroxy-alcohol (as methyl alcohol), because it can generate cacodorous acid esters.Reaction is preferably carried out in the presence of the alcohol alcoxylates of surfactant types or alkoxylate phenol, and this class tensio-active agent has the work of consisting of phase-transferring agent in order to uniform basically polyhydroxy amine and tri-glyceride reactant admixture to be provided.The exemplary of this class material comprises: NEODOL10-8, NEODOL23-3, NEODOL25-12 and NEODOL11-9 and GENAPOL26-L-5.Formula (I) and prefabricated quantification compound (II) also can be used for this purpose, and in typical pattern, reaction medium will comprise about the 10%-25% of total reactant weight.
Reaction conditions-this reaction is preferably in molten state and carries out, it is in about 30 minutes of 120-140 ℃ of congruent melting under vacuum that N-replaces polyhydroxy amine, consisting of phase-transferring agent (preferred NEODOL) and triglyceride oil, in reaction mixture, add catalyzer (preferred propylene glycol sodium) with respect to about 5 mol % of polyhydroxy amine, in seconds reactant becomes homogeneous, reaction mixture to 85 ℃ at once, this moment, reaction is near finishing.Reaction mixture was kept under vacuum one hour again and was finished reaction.
In another pattern, with NEODOL, oil, catalyzer and polyhydroxy amine at room temperature mix, and heated mixt becomes homogeneous phase to 85-90 ℃ at about 75 minutes internal reaction things under vacuum, reaction mixture was kept 2 hours for about 90 ℃ under vacuum again, and this moment, reaction was finished.
In above-mentioned reaction, triglyceride oil: the mol ratio of polyhydroxy amine is generally 1: 2-1: in 3 scopes.
The product arrangement: present method products therefrom will contain polyhydroxy fatty acid amide and glycerol, if need, glycerol can be removed by distillation method.
Below more at large describe and illustrate this building-up process.
The preparation of low smelly light polyhydroxy fatty acid amide
With perhydro-palm-kernel oil (773.8 grams, 1.0418 moles, 1.0 molar equivalents) fusion, and under 70-100 ℃ and vacuum, place 0.5-1 hour to remove any volatile component.The time with also placing 0.5-1 hour to remove volatile component with NEODOL25-12 (320 gram) fusion and under 70-100 ℃ and vacuum.At 60 ℃, above-mentioned palm-kernel oil and NEODOL25-12 joined in three mouthfuls of round-bottomed flasks of logical nitrogen of one 3 liters, flask is equipped with machinery disturbs and mixes device, thermometer and gas inlet and outlet.The interior mixture of blender jar also adds Powdered N-methylglucosamine (E Merck, 521.6 grams, 2.6720 moles, 2.56 molar equivalents).After adding, be positioned over reactant under the vacuum and be heated to 85 ℃, add 1,2-propylene glycol solution (24% propylene glycol solutions of 54.73 grams, 0.1336 mole, 5 moles of % are with respect to the N-methylglucosamine) is made catalyzer.Reaction mixture is placed vacuum, and this slurry became in 1-2 hour clearly, 85 ℃ of stirred reaction mixtures totally 4 hours, removed by filter unreacted N-methylglucosamine small shreds, and the reaction mixture bottling is also solidified.The N-methylglucosamine generates, and the transformation efficiency of fatty acid amide is generally 95-99%, and depends on that the ratio of reaction conditions and used oil can be up to 99.95%.Product has low stink, contains the lipid acid pollutent that is lower than about 0.2% weight content usually, and the latter measures with gc analysis.
Above-mentioned steps can replace the N-methylglucosamine to carry out with N-(3-methoxy-propyl) glycosamine, makes corresponding fatty acid amide surfactant.
The below industrial application explanation of the polyhydroxy fatty acid amide surfactant that makes for the inventive method, but also be not limited thereto, with particulate state, strip, sheet, liquid and gelatinously variously wash and starch, dishwashing and bathing be with all adopting the tensio-active agent that provides here in the prescription.
Example I
A kind of liquid is washed and starched washing composition and is made up of following component:
Component % (weight)
C
12-14EO2.25 vitriol 15.0
C
12-14Alkyl-sulphate 6.0
Lipid acid N-methylglucosamine
*6.0
Trisodium Citrate 6.0
Monoethanolamine 2.5
Water/1,2-propylene glycol/ethanol (100: 1: 1) remaining sum
* make by the hard palm kernel fatty acid.
In above-mentioned prescription, the glycosamine tensio-active agent can be replaced by the hard palm kernel fatty acid acid amides of N-(3-methoxy-propyl) glycosamine of equivalent to guarantee the better inhibition of dye transfer between fiber.
Present method is described as follows further, and usually, operating parameters must be considered following four aspects:
1, N-methylglucosamine (NMG) is heated to 120 ℃, is being lower than under the vacuum of 100mmHg dehydration 30 minutes again.
2, add pretreated sclerosis palm-kernel oil (70 ℃) to N-methylglucosamine solution, extract additional water, maintain under 120 ℃ and the micro-vacuum about 30 minutes.
3, make the slip (5 mole %s, preferably 8-10 mole %) of sodium methylate powder in NEODOL or propylene glycol, it is added in the reaction mixture, this will reduce the temperature of reaction mixture; Optimal reaction temperature is 100-105 ℃, is reflected under the 200-300mmHg to carry out, or carries out under nitrogen protection.
4, the reaction times is about 3-4 hour, after reaction is carried out 2 hours, adds (as 1%-2%) catalyzer, can obtain higher transformation efficiency.
Example II
The frit reaction of H-PKO glycosamine and NEOD OL11-9
To internal thermometer is housed, vacuum pipeline adds Powdered N-methylglucosamine (245.98 grams, 1.26 moles) in 1000 milliliters of three mouthfuls of round-bottomed flasks of nitrogen pipeline and mechanical stirrer.The N-methylglucosamine is in 130-140 ℃ of fusion and dry under vacuum.Be equipped with at another and add sclerosis palm-kernel oil (305 grams in 1000 milliliters of round-bottomed flasks of internal thermometer and vacuum pipeline, 0.434 mole) and NEODOL11-9 (102.36 gram), palm-kernel oil (the H-PKO)/NEODOL11-9 that will harden is heated to 130-140 ℃ and dry under vacuum.In exsiccant N-methylglucosamine, add exsiccant (H-PKO)/NEODOL11-9 mixture while mixing, under 136 ℃, add sodium methylate (3.4 grams to this mixture, mole) 0.063 (the methanol solution form with 25% weight adds), and take out sufficient vacuum at once to remove methyl alcohol.This mixture became homogeneous phase in 1 minute, this moment is cooling slowly, and mixture is at 27 minutes internal cooling to 95 ℃, and kept reaction at 95-100 ℃, and in the time of 60 minutes, inclining mixture, and gc analysis points out that residual N-methylglucosamine is lower than 1%.
EXAMPLE III
100 1b H-PKO glucamides
To internal thermometer is housed, add sclerosis palm-kernel oil (15.357 kilograms, 21.804 moles) and NEODOL25-12 (6.803 kilograms) in three mouthfuls of round-bottomed flasks of 72 liters of vacuum pipeline, nitrogen pipeline (removing vacuum uses) and mechanical stirrer.Add the back and be about to mixture heating up to 50 ℃ and dry under vacuum, in dry mixture, add (11.067 kilograms of pulverous N-methylglucosamines while mixing, 56.69 mole), and then add (1.111 kilograms in propylene glycol sodium, 2.8345 mole), and with mixture heating up to 70-80 ℃ and place (about 5 ＂ Hg) under the vacuum.Mixture became homogeneous phase in 1 hour.Hypsokinesis in 3 hours goes out mixture, and gc analysis points out that residual N-methylglucosamine is lower than 1%.
EXAMPLE IV
H-PKO glucamide low temperature slip
To internal thermometer is housed, vacuum pipeline adds sclerosis palm-kernel oil (126.60 grams, 0.17973 mole) and NEODOL11-9 (51.14 gram) in 500 milliliters of three mouthfuls of round-bottomed flasks of nitrogen pipeline and mechanical stirrer.Add the back and be about to mixture heating up to 100 ℃ and dry under vacuum.Dry mixture is cooled to 50-60 ℃ and to wherein adding sodium methylate (1.38 gram, 0.02561 mole) (adding with 25% methanol solution form).Heated mixt is to 90-95 ℃ and remove methyl alcohol under vacuum.At 90-95 ℃, add pulverous N-methylglucosamine (100.00 grams, 0.51224 mole) and vacuumize to the mixture of separating methanol, mixture became homogeneous phase in 1 hour, and after 4 hours, inclining mixture, analyzes with vapor-phase chromatography.
EXAMPLE V
H-PKO glucamide and propylene glycol frit reaction
To internal thermometer is housed, vacuum pipeline adds Powdered N-methylglucosamine (127.45 grams, 0.67285 mole) in 500 milliliters of three mouthfuls of round-bottomed flasks of nitrogen pipeline and mechanical stirrer.The N-methylglucosamine is in 130-140 ℃ of fusion and dry under vacuum.Be equipped with to another and add sclerosis palm-kernel oil (156.41 grams, 0.22206 mole) in 500 milliliters of round-bottomed flasks of internal thermometer and vacuum pipeline, the palm-kernel oil that will harden be heated to 130-140 ℃ and under vacuum drying.In exsiccant N-methylglucosamine, add exsiccant sclerosis palm-kernel oil and propylene glycol (31.54 gram) while mixing, add sodium methylate (1.76 grams, 0.03264 mole) (form with the methanol solution of 25% weight adds) and vacuumize (15 ＂ Hg) at once to this mixture at 120 ℃ to remove methyl alcohol.Mixture became homogeneous phase in 15 minutes, cool off this moment.Mixture was chilled to 90 ℃ in 7 minutes, and kept reaction at about 90 ℃.In the time of 85 minutes, incline and mixture and with gc analysis.
Observe, after H-PKO adds to NMG, adopt vacuum technique can further reduce the water-content (the NMG tool is not emitted the trend of water) of system, in total reactant, reduce last 1-5% water-content until bottom line (being lower than about 0.1%), then the generation of lipid acid also can reduce (1% or still less significantly, generally can be lower than about 0.5% lipid acid), and the usefulness of catalyzer can improve significantly.
Claims (8)
1, a kind of method with fatty acid ester and N-alkyl, N-alkoxyl group or N-aryloxy polyhydroxy amine prepared in reaction polyhydroxy fatty acid amide surfactant reaction product, its characteristics are that its usefulness tri-glyceride is as fatty acid ester, and reaction is not carried out in monoalcohol solvent, thereby has reduced the content of lipid acid in the reaction product to greatest extent.
2, the method for claim 1 is reflected in the water that is lower than 0.1% weight and carries out.
3, the method for claim 1, its improvement also comprise under being reflected at alkoxide catalysis exists carries out, and this alkoxide catalysis is selected from an alkali metal salt of polyhydroxy-alcohol.
4, the method for claim 3, wherein alkoxide catalysis is selected from an alkali metal salt of ethylene glycol, propylene glycol and glycerol.
5, the process of claim 1 wherein that reaction is to carry out in the presence of alcohol alcoxylates or ethoxylated alkyl phenols.
6, the process of claim 1 wherein that the fatty acid content in the reaction product is lower than 1% (weight).
7, the method for claim 2, wherein the fatty acid content in the reaction product is lower than 1% (weight).
8, the process of claim 1 wherein that polyhydroxy amine and fatty acid content all are lower than 1% (weight) in the reaction product.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19800894A | 1994-02-17 | 1994-02-17 | |
| US33430594A | 1994-11-04 | 1994-11-04 | |
| US08/334,305 | 1994-11-04 | ||
| US08/198,008 | 1994-11-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1145063A true CN1145063A (en) | 1997-03-12 |
Family
ID=26893387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95192460.5A Pending CN1145063A (en) | 1994-02-17 | 1995-02-10 | Synthesis of polyhydroxy fatty acid amides from triglycerides |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPH09509416A (en) |
| CN (1) | CN1145063A (en) |
| MX (1) | MX9603509A (en) |
| WO (1) | WO1995022519A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101260064B (en) * | 2008-04-18 | 2012-03-21 | 江门市江海区嘉诺化工发展有限公司 | Technique for producing N.N-ethylene bisoleamide |
| CN102907418A (en) * | 2012-10-24 | 2013-02-06 | 深圳诺普信农化股份有限公司 | Pesticide solvent using jatropha curcas source, and preparation method and application for pesticide solvent |
| CN103004756A (en) * | 2012-12-28 | 2013-04-03 | 深圳诺普信农化股份有限公司 | Pesticide solvent and preparation method and applications thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8853433B2 (en) * | 2011-07-28 | 2014-10-07 | Conopco, Inc. | General method for preparing fatty acyl amido based surfactants |
| US8822711B2 (en) * | 2011-07-28 | 2014-09-02 | Conopco, Inc. | Method for preparing fatty acyl amido carboxylic acid based surfactants |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2703798A (en) * | 1950-05-25 | 1955-03-08 | Commercial Solvents Corp | Detergents from nu-monoalkyl-glucamines |
| US3395162A (en) * | 1963-08-26 | 1968-07-30 | Lever Brothers Ltd | Process for the preparation of amides |
| JP2991775B2 (en) * | 1990-09-28 | 1999-12-20 | ザ、プロクター、エンド、ギャンブル、カンパニー | Preparation of glucamide detergent assisted by phase change agent |
| US5188769A (en) * | 1992-03-26 | 1993-02-23 | The Procter & Gamble Company | Process for reducing the levels of fatty acid contaminants in polyhydroxy fatty acid amide surfactants |
| DE69409391T2 (en) * | 1993-09-09 | 1998-10-29 | Procter & Gamble | AUTOMATIC DISHWASHING WITH ALKOXY OR ARYLOXYAMIDTENSIDE |
-
1995
- 1995-02-10 MX MX9603509A patent/MX9603509A/en unknown
- 1995-02-10 WO PCT/US1995/001687 patent/WO1995022519A1/en active Application Filing
- 1995-02-10 JP JP7521849A patent/JPH09509416A/en active Pending
- 1995-02-10 CN CN95192460.5A patent/CN1145063A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101260064B (en) * | 2008-04-18 | 2012-03-21 | 江门市江海区嘉诺化工发展有限公司 | Technique for producing N.N-ethylene bisoleamide |
| CN102907418A (en) * | 2012-10-24 | 2013-02-06 | 深圳诺普信农化股份有限公司 | Pesticide solvent using jatropha curcas source, and preparation method and application for pesticide solvent |
| CN102907418B (en) * | 2012-10-24 | 2014-10-01 | 深圳诺普信农化股份有限公司 | Pesticide solvent using jatropha curcas source, and preparation method and application for pesticide solvent |
| CN103004756A (en) * | 2012-12-28 | 2013-04-03 | 深圳诺普信农化股份有限公司 | Pesticide solvent and preparation method and applications thereof |
| CN103004756B (en) * | 2012-12-28 | 2015-04-22 | 深圳诺普信农化股份有限公司 | Pesticide solvent and preparation method and applications thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1995022519A1 (en) | 1995-08-24 |
| MX9603509A (en) | 1997-03-29 |
| JPH09509416A (en) | 1997-09-22 |
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