CN104741032A - Method for preparing fatty acyl sodium methionine and composition comprising surfactant - Google Patents
Method for preparing fatty acyl sodium methionine and composition comprising surfactant Download PDFInfo
- Publication number
- CN104741032A CN104741032A CN201510047028.5A CN201510047028A CN104741032A CN 104741032 A CN104741032 A CN 104741032A CN 201510047028 A CN201510047028 A CN 201510047028A CN 104741032 A CN104741032 A CN 104741032A
- Authority
- CN
- China
- Prior art keywords
- acid methyl
- fatty acid
- sodium
- methioninate
- surfactant
- 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
Landscapes
- Detergent Compositions (AREA)
Abstract
The invention discloses a method for preparing fatty acyl sodium methionine and a composition comprising the surfactant, and belongs to the technical field of fine chemical engineering. The technology for synthesis of the fatty acyl sodium methionine surfactant provided by the invention is characterized in that the fatty acyl sodium methionine surfactant is synthesized by taking fatty acid methyl ester from a natural grease source as a raw material, namely, fatty acyl sodium methionine and the composition comprising the surfactant are prepared from the fatty acid methyl ester and the sodium methionine in the presence of a phase transfer catalyst PEG 1500. According to the method disclosed by the invention, the raw material utilization rate is high, the yield is high, the product can be directly used without being separated and purified, the active substance content is high, the surface activity is high, the synthetic route is simple, the environment is not polluted, and therefore, the method is a clean production technology. The invention further discloses a surfactant composition comprising the fatty acyl sodium methionine.
Description
Technical field
The present invention relates to the method for the composition prepared fatty acyl group Sodium L-methioninate and comprise this surfactant; specifically under phase transfer catalyst polyethylene glycol 1500 (PEG1500) existence condition; utilize fatty acid methyl ester and Sodium L-methioninate Reactive Synthesis fatty acyl group Sodium L-methioninate class surfactant, belong to technical field of fine.
Background technology
Surfactant is a kind of important functional fine chemicals, owing to having special function, is widely used in each industrial department and field.Fatty acid acylamino acid class surfactant is the mild anion surfactant by carrying out structure of modification and an obtained protein species to common soaps, it is except having the emulsification of surfactant, washing, dispersion, foaming, infiltration, outside the key propertys such as solubilising, compared with common soaps surfactant, owing to introducing amide group and amino acid moiety, thus have more excellent anti-water hardness tolerance, low irritant, hypotoxicity, good biodegradability properties and to advantages such as the good compatibilities of human body, washing agent can be widely used in, cosmetics, medicine, food, biological, material, the fields such as environmental protection.Along with people more and more pay close attention to the security of surfactant product, mildness and the raising to environmental protection requirement; such surfactant will more and more be subject to people's attention; application can be more and more extensive, has good researching value and application prospect.
The synthetic method of fatty acid acylamino acid class surfactant mainly contains chloride method, fatty acid anhydride method, Arneel SD Hydrolyze method, amide carbonylation method, enzyme process etc.Although these the four kinds of method researchs of fatty acid anhydride method, Arneel SD Hydrolyze method, amide carbonylation method, enzyme process comparatively early, all do not obtain industrial application for various reasons.The method industrially applied at present is chloride method, adopt Schotten-Baumann reaction, but this method subject matter uses in synthesis to have severe corrosive and irritating raw material, as phosphorus trichloride, thionyl chloride or phosgene and fat acyl chloride, there is problem of environmental pollution, very high to acyl chlorides quality requirement when amidation process, moisture storage must be completely cut off, to reduce its hydrolysis, otherwise after hydrolysate introduces product, remove very difficult, and also have that salt content is high, accessory substance is many, product color is poor and have the shortcomings such as peculiar smell.
The technology improved chloride method deposits at organic solvent to be prepared in case, as acetone, isopropyl alcohol, isobutanol or the tert-butyl alcohol etc., needs to reclaim organic solvent, the method cost can be made to improve.
A kind of method that methyl esters prepares fatty acid acylamino acid class surfactant is described in patent ZL 200110162146.2.But the shortcoming of the method described in ZL 200110162146.2 is, does not use cheap fatty acid methyl ester, therefore still there is the economic possibility improved.In addition, the character of gained surfactant still requires further improvement.
Therefore the object of this invention is to provide for the preparation of fatty acyl group Sodium L-methioninate and the method for composition comprising this surfactant; tool has the following advantages: described method can use cheap and commercially available fatty acid methyl ester; as the fatty acid methyl ester that commercially available natural oil is originated; and not with an organic solvent, and provide the preparation method of the fatty acyl group Sodium L-methioninate with high active content and high surface and the composition comprising this surfactant.
Summary of the invention
Order of the present invention be with fatty acid methyl ester and Sodium L-methioninate for raw material, prepare fatty acyl group Sodium L-methioninate class surfactant.The chemical structural formula of fatty acyl group Sodium L-methioninate class surfactant of the present invention is as follows:
In formula: R is C
4~ C
24the alkyl of the aliphatic acid of saturated or unsaturated, straight or branched, as capric acid, laurate, myristic acid, palmitic acid, stearic acid, oleic acid, the alkyl of linoleic acid etc.;
Object of the present invention reaches by following technical scheme:
Synthetic method of the present invention utilizes fatty acid methyl ester and Sodium L-methioninate to react under catalysts conditions to generate fatty acyl group Sodium L-methioninate surfactant.Synthetic route is as follows:
Methyl esters provided by the invention is the fatty acid methyl ester in various natural oil source, comprises coconut oil fatty acid methyl ester, palm kernel fatty acid methyl esters, palm oil fatty acid methyl esters, cottonseed oil fatty acid methyl esters, rapeseed oil fatty acid methyl esters, methyl soyate, corn oil fatty acid methyl esters, Rice oil fatty acid methyl ester, peanut oil fatty acid methyl esters, tallow acid methyl esters, hydrogenated tallow methyl esters, pig fat fatty acid methyl esters etc.
Catalyst provided by the invention is PEG1500.
Technology synthctic fat acyl group Sodium L-methioninate surfactant provided by the invention; product is the composition of different carbon chain fatty acyl group Sodium L-methioninate homologue; meet surfactant compound principle; synergistic function can be played; have that product property excellence, active matter content are high, surface-active advantages of higher; and the impurity content of toxic side effect can be reduced, make product have the security of better biocompatibility and Geng Gao.
The phase transfer catalyst PEG1500 that technology provided by the invention adopts is base starting material and the active components such as washing agent, cosmetics, medicine, play the effects such as adjusting viscosity, stable, emulsification, moisturizing, at this particularly advantageously, the composition that method according to the present invention obtains, product can directly use without the need to separating-purifying.
Another theme of the present invention relates to prepared according to the methods of the invention composition, and composition is containing the different carbon chain fatty acyl group Sodium L-methioninate homologue of 75-85wt%, 15-25wt%PEG1500,0.2-2wt% Sodium L-methioninate and 0.2-3wt% sodium soap.
Synthetic technology of the present invention overcomes in chloride method and produces that a large amount of spent acid needs that process, operating procedure are complicated, raw material phosphorus trichloride or thionyl chloride and fat acyl chloride excitant large, there is the shortcomings such as environmental pollution; the fatty acid methyl ester that the present invention originates with natural oil is for raw material; directly prepare fatty acyl group Sodium L-methioninate surfactant; reactions steps is few; be conducive to improving atom utilization and Atom economy; meeting Green Chemistry principle, is a kind of clearer production technology.
Detailed description of the invention
In a preferred embodiment of the invention, the mol ratio of fatty acid methyl ester and Sodium L-methioninate is: 1: 2 ~ 2: 1, preferably 1: 1 ~ 1.5: 1.
In a preferred embodiment of the invention, reaction temperature is 60 ~ 220 DEG C, preferably 130 ~ 190 DEG C.
In a preferred embodiment of the invention, catalyst charge is the 15-30wt% of reaction-ure mixture, preferred 20-25wt%.
In a preferred embodiment of the invention, 3 ~ 15 hours reaction time, preferably 5 ~ 10 hours.
Methyl alcohol as product removes preferably by decompression, obtains fatty acyl group Sodium L-methioninate surface activator composition.
Embodiment 1:
Is being furnished with stirring, thermometer, water knockout drum, 0.1mol Rice oil fatty acid methyl ester and 11.2gPEG1500 is added in the reaction bulb of reflux condensing tube, be warming up to after 100 DEG C of stirrings are melted and add 0.1mol Sodium L-methioninate, be heated to 170 DEG C, steady temperature reacts 5 hours, separate the methyl alcohol of generation, myristoyl Sodium L-methioninate content 0.2%, palmitoleoyl Sodium L-methioninate content 0.2%, palmityl Sodium L-methioninate content 14.5%, sub-oleoyl Sodium L-methioninate content 33.2%, oleoyl Sodium L-methioninate content 27.6%, stearyl Sodium L-methioninate content 1.3%, peanut enoyl-Sodium L-methioninate content 0.5%, peanut acyl group Sodium L-methioninate content 0.5%, 22 carbonic acyl radical Sodium L-methioninate content 0.1%, Sodium L-methioninate content 0.5%, sodium soap content 0.7%, the rice acyl group Sodium L-methioninate surface activator composition of PEG1500 content 20.7%.
Embodiment 2:
Is being furnished with stirring, thermometer, water knockout drum, 0.1mol palm kernel methyl oleate and 11.2gPEG1500 is added in the reaction bulb of reflux condensing tube, be warming up to after 100 DEG C of stirrings are melted and add 0.1mol Sodium L-methioninate, be heated to 160 DEG C, steady temperature reacts 7 hours, separate the methyl alcohol of generation, obtain caproyl Sodium L-methioninate content 0.1%, caprylyl Sodium L-methioninate content 1.7%, capryl Sodium L-methioninate content 2.2%, lauroyl Sodium L-methioninate content 33.8%, myristoyl Sodium L-methioninate content 13.8%, palmityl Sodium L-methioninate content 7.7%, sub-oleoyl Sodium L-methioninate content 1.7%, oleoyl Sodium L-methioninate content 13.5%, stearyl Sodium L-methioninate content 1.7%, peanut acyl group Sodium L-methioninate content 0.1%, Sodium L-methioninate content 0.5%, sodium soap content 0.6%, the palm-kernel oil acyl group Sodium L-methioninate surface activator composition of PEG1500 content 22.6%.
Embodiment 3:
A kind of method preparing soybean oil based acyl Sodium L-methioninate surfactant, it is characterized in that being furnished with stirring, thermometer, water knockout drum, 0.1mol methyl soyate and 11.2gPEG1500 is added in the reaction bulb of reflux condensing tube, be warming up to after 100 DEG C of stirrings are melted and add 0.1mol Sodium L-methioninate, be heated to 150 DEG C, steady temperature reacts 9 hours, separate the methyl alcohol of generation, obtain palmityl Sodium L-methioninate content 9.4%, sub-oleoyl Sodium L-methioninate content 43.8%, oleoyl Sodium L-methioninate content 21.7%, stearyl Sodium L-methioninate content 3.4%, Sodium L-methioninate content 0.5%, sodium soap content 0.7%, the soybean oil acyl group Sodium L-methioninate surface activator composition of PEG1500 content 20.5%.
Embodiment 4:
Is being furnished with stirring, thermometer, water knockout drum, 0.1mol hydrogenated methyl tallowate and 11.2gPEG1500 is added in the reaction bulb of reflux condensing tube, be warming up to after 100 DEG C of stirrings are melted and add 0.1mol Sodium L-methioninate, be heated to 150 DEG C, steady temperature reacts 9 hours, separate the methyl alcohol of generation, obtain mace oil acyl group Sodium L-methioninate content 0.2%, myristoyl Sodium L-methioninate content 2.4%, 15 carbonic acyl radical Sodium L-methioninate content 0.8%, palmitoleoyl Sodium L-methioninate content 1.7%, palmityl Sodium L-methioninate content 21.6%, heptadecene acyl group Sodium L-methioninate content 0.3%, 17 carbonic acyl radical Sodium L-methioninate content 1.6%, sub-oleoyl Sodium L-methioninate content 2.2%, oleoyl Sodium L-methioninate content 27.8%, stearyl Sodium L-methioninate content 19.6%, Sodium L-methioninate content 0.6%, sodium soap content 0.8%, the h-tallow acyl group Sodium L-methioninate surface activator composition of PEG1500 content 20.4%.
Comparative example:
0.1mol methyl laurate and 0.25g potassium oxide and 4A zeolite is added in the four mouthfuls of round-bottomed flasks being furnished with stirring, thermometer, water knockout drum, reflux condensing tube; 0.15mol Sodium L-methioninate is added after being warming up to 120 DEG C after abundant stirring; be heated to 150 DEG C; steady temperature reacts 5 hours; separate a small amount of methyl alcohol, obtain the lauroyl Sodium L-methioninate of active matter content 78.5%.
Comparative example corresponds to the prior art of patent ZL 200110162146.2, and methyl ester feedstocks is that the laurate that obtains based on natural acid fractionation is further through strand methyl laurate prepared by esterification.
The determination of surface activity of composition of the present invention: surface-active adopts the full-automatic surface tension instrument of DCAT11, measure at 25 DEG C, list the surface tension (γ under the critical micelle concentration (cmc) of product and critical micelle concentration in Table 1
cmc).
Surface tension under table 1 critical micelle concentration and critical micelle concentration
The comparing result display listed in table 1, fatty acyl group Sodium L-methioninate surface activator composition according to the present invention can realize cmc and γ more significantly lower than the lauroyl Sodium L-methioninate of comparative example
cmc, show have the capillary efficiency of higher reduction and usefulness, namely have higher surface-active.
Claims (8)
1. the preparation method of a fatty acyl group Sodium L-methioninate and fatty acyl group methionine surface activator composition; it is characterized in that reacting under catalysts conditions with the fatty acid methyl ester in natural oil source and Sodium L-methioninate generating fatty acyl group Sodium L-methioninate surfactant, after removing methyl alcohol, obtain fatty acyl group methionine surface activator composition.
2. method according to claim 1, it is characterized in that the fatty acid methyl ester that natural oil is originated, comprise coconut oil fatty acid methyl ester, palm kernel fatty acid methyl esters, palm oil fatty acid methyl esters, cottonseed oil fatty acid methyl esters, rapeseed oil fatty acid methyl esters, methyl soyate, corn oil fatty acid methyl esters, Rice oil fatty acid methyl ester, peanut oil fatty acid methyl esters, tallow acid methyl esters, hydrogenated tallow methyl esters, pig fat fatty acid methyl esters.
3. method according to claim 1, is characterized in that catalyst is PEG1500.
4. method according to claim 1, is characterized in that the mol ratio of fatty acid methyl ester and Sodium L-methioninate is: 1: 2 ~ 2: 1.
5. method according to claim 1, is characterized in that reaction temperature is 60 ~ 220 DEG C.
6. method according to claim 1, is characterized in that catalyst charge is the 15-30wt% of reaction-ure mixture.
7. method according to claim 1, is characterized in that the reaction time is 3 ~ 15 hours.
8. method according to claim 1, is characterized in that the different carbon chain fatty acyl group Sodium L-methioninate homologue of composition containing 75-85wt% of preparation, 15-25wt%PEG1500,0.2-2wt% Sodium L-methioninate and 0.2-3wt% sodium soap.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510047028.5A CN104741032A (en) | 2015-01-30 | 2015-01-30 | Method for preparing fatty acyl sodium methionine and composition comprising surfactant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510047028.5A CN104741032A (en) | 2015-01-30 | 2015-01-30 | Method for preparing fatty acyl sodium methionine and composition comprising surfactant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104741032A true CN104741032A (en) | 2015-07-01 |
Family
ID=53581625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510047028.5A Pending CN104741032A (en) | 2015-01-30 | 2015-01-30 | Method for preparing fatty acyl sodium methionine and composition comprising surfactant |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104741032A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105126698A (en) * | 2015-07-24 | 2015-12-09 | 华南理工大学 | Amino acid-type surfactant containing sulfoxide group, preparation method and application thereof |
| CN109248633A (en) * | 2018-02-06 | 2019-01-22 | 广州大学 | A kind of amino acid surfactant and its preparation method and application |
| CN114380711A (en) * | 2021-12-30 | 2022-04-22 | 广州花语精细化工有限公司 | Preparation method of amino acid surfactant |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005126740A (en) * | 2003-10-21 | 2005-05-19 | Meltex Inc | Electroplating method |
| CN101773802A (en) * | 2010-01-06 | 2010-07-14 | 苏州元素集化学工业有限公司 | Non-ionic surface active agent and manufacturing method thereof |
| CN102266737A (en) * | 2011-06-16 | 2011-12-07 | 北京工商大学 | Method for preparing N-fatty acyl amino acid type surfactant by fat |
| CN102311359A (en) * | 2011-06-16 | 2012-01-11 | 北京工商大学 | Method for preparing N-fatty acyl amino acid surfactant from methyl ester |
| CN103649043A (en) * | 2011-07-28 | 2014-03-19 | 荷兰联合利华有限公司 | Method for preparing fatty acyl amido carboxylic acid based surfactants |
| CN103772227A (en) * | 2014-01-13 | 2014-05-07 | 石家庄菠莉亚日用化工有限公司 | Preparation method for grease-based amino acid salt-series surfactant |
| CN103857653A (en) * | 2011-07-28 | 2014-06-11 | 荷兰联合利华有限公司 | General method for preparing fatty acyl amido based surfactants |
-
2015
- 2015-01-30 CN CN201510047028.5A patent/CN104741032A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005126740A (en) * | 2003-10-21 | 2005-05-19 | Meltex Inc | Electroplating method |
| CN101773802A (en) * | 2010-01-06 | 2010-07-14 | 苏州元素集化学工业有限公司 | Non-ionic surface active agent and manufacturing method thereof |
| CN102266737A (en) * | 2011-06-16 | 2011-12-07 | 北京工商大学 | Method for preparing N-fatty acyl amino acid type surfactant by fat |
| CN102311359A (en) * | 2011-06-16 | 2012-01-11 | 北京工商大学 | Method for preparing N-fatty acyl amino acid surfactant from methyl ester |
| CN103649043A (en) * | 2011-07-28 | 2014-03-19 | 荷兰联合利华有限公司 | Method for preparing fatty acyl amido carboxylic acid based surfactants |
| CN103857653A (en) * | 2011-07-28 | 2014-06-11 | 荷兰联合利华有限公司 | General method for preparing fatty acyl amido based surfactants |
| CN103772227A (en) * | 2014-01-13 | 2014-05-07 | 石家庄菠莉亚日用化工有限公司 | Preparation method for grease-based amino acid salt-series surfactant |
Non-Patent Citations (1)
| Title |
|---|
| 徐宝财等: "以脂肪酸甲酯为原料制备N-酰基谷氨酸的工艺研究", 《表面活性剂工业》, no. 4, 31 December 1994 (1994-12-31) * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105126698A (en) * | 2015-07-24 | 2015-12-09 | 华南理工大学 | Amino acid-type surfactant containing sulfoxide group, preparation method and application thereof |
| CN109248633A (en) * | 2018-02-06 | 2019-01-22 | 广州大学 | A kind of amino acid surfactant and its preparation method and application |
| CN114380711A (en) * | 2021-12-30 | 2022-04-22 | 广州花语精细化工有限公司 | Preparation method of amino acid surfactant |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102311359B (en) | Method for preparing N-fatty acyl amino acid surfactant from methyl ester | |
| CN1040112C (en) | Process for preparing N-alkyl polyhydroxy amines and fatty acid amides therefrom in hydroxy solvents | |
| EP2888226B2 (en) | Method to produce n-acyl amino acid surfactants using n-acyl amino acid surfactants or the corresponding anhydrides as catalysts | |
| US9714399B2 (en) | Preparation of lactylates directly from oil | |
| EP1449577B1 (en) | Imidazoline derived amphoacetates surfactants of higher purity. | |
| CN102266737B (en) | Method for preparing N-fatty acyl amino acid type surfactant by fat | |
| CA2839047A1 (en) | General method for preparing fatty acyl amido based surfactants | |
| ES2900329T3 (en) | Amphoteric ester sulfonates | |
| EA023748B1 (en) | Method for preparing fatty acyl amido carboxylic acid based surfactants | |
| BR112016003494B1 (en) | process for the preparation of n-acylamino acid salts | |
| CN103772227B (en) | Preparation method of grease-based amino acid salt series surfactant | |
| CN104741032A (en) | Method for preparing fatty acyl sodium methionine and composition comprising surfactant | |
| CN100404117C (en) | Preparation method of alpha-alkyl betaine amphoteric surfactant | |
| EA025795B1 (en) | Fatty acyl amido based surfactant concentrates | |
| CN104607096A (en) | Method for preparing grease acyl sodium alanine and surfactant composition comprising grease acyl sodium alanine | |
| CN104607098A (en) | Method for preparing grease acyl sodium leucine and surface active agent composition containing grease acyl sodium leucine in phase-transfer catalysis way | |
| WO2023093677A1 (en) | Synthesis process for fatty acyl taurate | |
| CN104741033A (en) | Method for preparing fatty acyl potassium glycine and composition containing surfactant | |
| CN104741031B (en) | A kind of fatty acyl group sodium sarcosinate and comprise the preparation method of compositions of this surfactant | |
| CN104607097B (en) | A kind of phase transfer catalysis prepares oils and fats acyl L-Lysine sodium salt and the method for the compositions comprising this surfactant | |
| JPH02218657A (en) | Production of surfactant in high concentration | |
| CN104607095A (en) | Method for preparing sodium fatty-acyl threonine and composition containing surfactant | |
| CN112812031B (en) | Preparation method of N-acyl amino acid type surfactant | |
| CN104741034A (en) | Method for preparing lipidic sodium acyl valinate and surface active agent composition comprising same | |
| JP4137494B2 (en) | Method for producing weakly acidic transparent solid detergent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150701 |