CN103724180B - A kind of method preparing strange carbon fatty acid metallic soap and strange carbon fatty acid thereof - Google Patents
A kind of method preparing strange carbon fatty acid metallic soap and strange carbon fatty acid thereof Download PDFInfo
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- CN103724180B CN103724180B CN201310691104.7A CN201310691104A CN103724180B CN 103724180 B CN103724180 B CN 103724180B CN 201310691104 A CN201310691104 A CN 201310691104A CN 103724180 B CN103724180 B CN 103724180B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
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Abstract
The present invention relates to a kind of with the strange carbon fatty acid metallic soap of the even carbon fatty acid metallic soap of Alpha-hydroxy for a minimizing carbon atom of raw material preparation ratio and the synthetic method of strange carbon fatty acid thereof.Described method is from the even carbon fatty acid of abundant natural fats and oils, preparing on the basis of alpha-hydroxy fatty acid metallic soap through chloro, hydrolysis reaction in advance, invent a kind of prepare than the strange carbon fatty acid metallic soap of a minimizing carbon atom and the synthetic method of lipid acid, process and product.Raw material sources of the present invention are in biomass, cheap and easy to get, good economy performance; Reaction time is short, productive rate is high, selectivity is good; Technological process is corrosion-free, low stain, environmental friendliness; This method is conducive to high added value Green Development and utilizes a large amount of natural fats and oils, and the strange carbon fatty acid metallic soap providing product line complete and strange carbon fatty acid thereof, fill up natural blank.
Description
[technical field]
The present invention relates to a kind of novel method preparing strange carbon fatty acid metallic soap and strange carbon fatty acid thereof, belong to organic compound synthesis technical field.
[background technology]
Along with petroleum and natural gas resource is day by day deficient and price rises steadily, human society is constantly seek can the non-renewable resource such as petroleum replacing, and therefore the development & application of grease chemical article becomes global study hotspot gradually.Lipid acid composition mainly even carbon fatty acid homologue in natural fats and oils, and strange carbon fatty acid homologue kind is seldom and natural abundance is minimum.But strange carbon fatty acid and metallic soap thereof all have larger application potential in fields such as organic synthesis, lubricant, tensio-active agent, washing composition, medicine intermediates, the preparation method therefore developing strange carbon fatty acid and metallic soap thereof to lifting traditional industries and development of new applications field all significant.
The method of the strange carbon fatty acid of conventional synthesis and metallic soap thereof is all subject to various restriction, and the method product as petroleum fractions isolated strange carbonic acid after oxicracking is complicated, and serious three wastes, is abandoned in worldwide; Metal-organic carbon-to-carbon is utilized to extend reaction method then expensive reagents, severe reaction conditions, the method non-friendly pattern of a kind of environment be especially hydrolyzed after the even carbon alkanol of long-chain and derivative thereof and the addition of high toxicity nitrile compounds, only should small-scale preparative chemistry reagent; The unique channel obtaining strange carbon fatty acid from natural even carbon fatty acid resource is the oxidative cracking reaction utilizing unsaturated fatty acids, as oleic acid oxidation prepare nonane diacid while by-product n-nonanoic acid, methyl ricinolcic acid cracking is for undecylenic acid etc., but poor selectivity, complex steps, environmental pollution, and the series product that can not obtain strange carbon fatty acid.Therefore, there is no the large-scale production of the strange carbon fatty acid of series and metallic soap thereof at present, therefore its application is limited.
Present inventor has developed by the method for natural acid α-monochloro generation synthesis alpha-chloro-fatty acid series product and obtained Chinese invention patent (ZL200810021288.5) early stage, is Material synthesis alpha-hydroxy fatty acid metallic soap again subsequently and has applied for Chinese invention patent (201110072181.5) with alpha-chloro-fatty acid.The application just with the even carbon fatty acid metallic soap of Alpha-hydroxy for raw material, utilize decarboxylic reaction, obtain thus and reduce the strange carbon fatty acid metallic soap of a carbon atom or the series product of corresponding strange carbon fatty acid than the even carbon fatty acid metallic soap of raw material Alpha-hydroxy.
[summary of the invention]
[technical problem that will solve]
The object of this invention is to provide a kind of method preparing strange carbon fatty acid metallic soap.
Another object of the present invention is to provide a kind of method preparing strange carbon fatty acid.
Another object of the present invention is to provide the strange carbon fatty acid metallic soap that described method prepares.
Another object of the present invention is to provide the strange carbon fatty acid that described method prepares.
Another object of the present invention be to provide described using even for Alpha-hydroxy carbon fatty acid metallic soap as the purposes of raw material for the preparation of the strange carbon fatty acid metallic soap and strange carbon fatty acid thereof that reduce by a carbon atom than raw material.
[technical scheme]
The alpha-hydroxy fatty acid metallic soap that the object of the invention is to prepare through chloro, hydrolysis reaction with natural even carbon fatty acid is for raw material, there is provided a kind of prepare than the strange carbon fatty acid metallic soap of a minimizing carbon atom or the synthetic method of its corresponding lipid acid, the present invention develops the new way of an efficiency utilization biomass lipid acid.Described alpha-hydroxy fatty acid metallic soap is according to Chinese invention patent ZL200810021288.5, and the method recorded in the Chinese invention patent file of application number CN201110072181.5 prepares.
Main chemical reactions formula of the present invention is as follows:
Namely at high temperature there is carboxylic acid metal's soap that oxidative decarboxylation reaction generates a minimizing carbon atom in alpha-hydroxy carboxylic acid compounds metallic soap.
The present invention is achieved through the following technical solutions:
A kind of synthetic method reducing the strange carbon fatty acid metallic soap of a carbon atom with the even carbon fatty acid metallic soap of Alpha-hydroxy for raw material preparation than this raw material, by the even carbon fatty acid metallic soap of raw material Alpha-hydroxy reacting by heating 1 ~ 5h under 200 ~ 300 DEG C of conditions, obtain the strange carbon fatty acid metallic soap reducing by a carbon atom than raw material thus, wherein the carbonatoms of the even carbon fatty acid metallic soap of Alpha-hydroxy is the even number in 4 ~ 24.
According to the embodiment of the present invention, the even carbon fatty acid metallic soap of described raw material Alpha-hydroxy is the mixture of one or more homologues with following general structure:
In formula, R is general formula is C
nh
2n+1straight chained alkyl, wherein n is the even number of 2 ~ 22; In formula, M is the metallic element in the first main group element, the metallic element in the second main group element except radium, any one in aluminium and the chromium in the period 4, manganese, iron, cobalt, nickel, copper, zinc metallic element; In formula, m is the valency of metallic element M.
According to the embodiment of the present invention, described product strange carbon fatty acid metallic soap is the mixture of one or more homologues with following general structure:
(RCOO)
mM
In formula, R is general formula is C
nh
2n+1straight chained alkyl, wherein n is the even number of 2 ~ 22; In formula, M is the metallic element in the first main group element, the metallic element in the second main group element except radium, any one in aluminium and the chromium in the period 4, manganese, iron, cobalt, nickel, copper, zinc metallic element; In formula, m is the valency of metallic element M.
According to another kind of preferred implementation of the present invention, the even number in n=10 ~ 16.
According to another kind of preferred implementation of the present invention, described temperature of reaction is 220 ~ 280 DEG C.
According to another kind of preferred implementation of the present invention, the described reaction times is 2 ~ 4h.
The invention still further relates to a kind of method preparing strange carbon fatty acid, prepare strange carbon fatty acid metallic soap according to the method described above, then adopt ion exchange method or direct acidization to prepare corresponding strange carbon fatty acid by strange carbon fatty acid metallic soap.
The strange carbon fatty acid metallic soap obtained according to described method.
The strange carbon fatty acid obtained according to described method.
Using even for Alpha-hydroxy carbon fatty acid metallic soap as raw material for the preparation of the purposes of strange carbon fatty acid metallic soap reducing by a carbon atom than raw material.
The invention provides strange carbon fatty acid metallic soap obtained by aforesaid method and strange carbon fatty acid thereof, the few and problem that kind is incomplete of natural strange carbon fatty acid quantity can be solved, for market provides new high-quality oiling product.
Preparing corresponding lipid acid by fatty acid metal soap is the process that industry practitioner knows, and therefore can prepare corresponding strange carbon fatty acid simply by methods such as ion exchange method or direct acidizations from strange carbon fatty acid metallic soap.
The implication of the even carbon fatty acid metallic soap of Alpha-hydroxy described in present specification refers to that carbon atom number is the alpha-hydroxy fatty acid metallic soap of even number, and the implication of corresponding strange carbon fatty acid metallic soap refers to that carbon atom number is the fatty acid metal soap of odd number.
[beneficial effect]
Compared with the method for the strange carbon fatty acid metallic soap of existing preparation and lipid acid thereof, beneficial effect of the present invention is as follows:
(1) the even carbon fatty acid metallic soap of raw material Alpha-hydroxy derives from biomass natural fats and oils, cheap and easy to get, sustainable, and the high added value Green Development being conducive to a large amount of natural fats and oils utilizes;
(2) method of the present invention short period, high yield, highly selective under catalyst-free condition prepares strange carbon fatty acid metallic soap, the simple also easy handling of reaction;
(3) the strange carbon fatty acid metallic soap of product of the present invention and strange carbon fatty acid thereof, product line is complete, fills up natural blank;
(4) corrosion-free, the low stain of the inventive method technological process, environmental friendliness;
(5) raw material of the inventive method and production cost low, good economy performance.
[accompanying drawing explanation]
Accompanying drawing 1 is gas chromatographic analysis figure after the thick product methyl esters of undeeanoic acid that embodiment 2 prepares;
Accompanying drawing 2 is gas-chromatography gas chromatographic analysis figure after the thick product methyl esters of tridecylic acid that embodiment 3 prepares.
[embodiment]
Below in conjunction with specific embodiment, the present invention is further illustrated, but limited the present invention never in any form, and any conversion done based on training centre of the present invention or replacement, all belong to protection scope of the present invention.
Embodiment 1:
1g Alpha-hydroxy capric acid manganese is ground and is evenly distributed in watch-glass, terminates reaction heat 5h at 200 DEG C after, be cooled to room temperature, obtain n-nonanoic acid manganese crude product.Crude product is with gc analysis after esterification is derivative, and n-nonanoic acid manganese productive rate is 50.3%.
Embodiment 2:
10g Alpha-hydroxy sodium laurate ground and is evenly distributed in culture dish, terminating reaction heat 2.5h at 240 DEG C after, be cooled to room temperature, obtain undeeanoic acid sodium crude product.Crude product is with gc analysis after esterification is derivative, and undeeanoic acid sodium productive rate is 78.4%.Crude product dilute hydrochloric acid solution neutralizes, esterification, rectifying, obtains undeeanoic acid sterling after hydrolysis, purity 99.0%, and gas chromatographic analysis figure is shown in accompanying drawing 1.
Embodiment 3:
100g Alpha-hydroxy TETRADECONIC ACID sodium is ground and is placed in 1000ml beaker bottom, passes into air with conduit and help to stir, terminate reaction heat 2h at 250 DEG C after, be cooled to room temperature, obtain tridecylic acid sodium crude product.Crude product is with gc analysis after esterification is derivative, and tridecylic acid sodium productive rate is 76.2%.Crude product dilute hydrochloric acid solution neutralizes, esterification, rectifying, obtains tridecylic acid sterling after hydrolysis, purity 99.0%, and gas chromatographic analysis figure is shown in accompanying drawing 2.
Embodiment 4:
1g Alpha-hydroxy palmitic acid beryllium is ground and is evenly distributed in watch-glass, terminates reaction heat 1.5h at 280 DEG C after, be cooled to room temperature, obtain pentadecanoic acid beryllium crude product.Crude product is with gc analysis after esterification is derivative, and pentadecanoic acid beryllium productive rate is 65.7%.
Embodiment 5:
20g Alpha-hydroxy sodium stearate ground and is placed in 200ml test tube, stirring with mesh-like raker stirrer, terminating reaction heat 2h at 260 DEG C after, be cooled to room temperature, obtain margaric acid sodium crude product.Crude product is with gc analysis after esterification is derivative, and margaric acid sodium productive rate is 77.8%.Crude product dilute hydrochloric acid solution neutralizes, esterification, rectifying, obtains margaric acid sodium pure product after hydrolysis, purity 98.0%.
Embodiment 6:
The Alpha-hydroxy coconut oil sodium prepared with industrial coconut oil is raw material, 200g Alpha-hydroxy coconut oil sodium is ground and is placed in 1000ml stainless steel cauldron, stir with mesh-like raker stirrer, and it is auxiliary to pass into air, reaction is terminated heat 3h at 245 DEG C after, be cooled to room temperature, obtain the corresponding strange sodium carbonate mixture crude product reducing by a carbon atom than component each in coconut oil.Crude product is with gc analysis after esterification is derivative, and wherein the productive rate of main component undeeanoic acid sodium is 56.1%, and the productive rate of tridecylic acid sodium is 7.5%.
Embodiment 7:
The Alpha-hydroxy sclerosis calcium palmitate prepared with industrial hardened palmitinic acid (stearic/palmitic acids is 60:40) is raw material, 2g Alpha-hydroxy sclerosis calcium palmitate is ground and is evenly distributed in culture dish, reaction is terminated heat 1h at 300 DEG C after, be cooled to room temperature, obtain the crude mixture based on margaric acid calcium and pentadecanoic acid calcium product.Crude product is with gc analysis after esterification is derivative, and wherein the productive rate of main component margaric acid sodium is 46.1%, and the productive rate of pentadecanoic acid sodium is 31.9%.
Embodiment 8:
The Alpha-hydroxy industry aluminum stearate prepared with industrial stearic acid (stearic/palmitic acids is 80:20) is raw material, 5g Alpha-hydroxy industry aluminum stearate is ground and is evenly distributed in culture dish, reaction is terminated heat 5h at 220 DEG C after, be cooled to room temperature, obtain the crude mixture based on margaric acid aluminium and pentadecanoic acid aluminium product.Crude product is with gc analysis after esterification is derivative, and wherein the productive rate of main component margaric acid aluminium is 64%, and the productive rate of pentadecanoic acid aluminium is 15%.
Embodiment 9:
1g alpha-hydroxybutyric acid copper ground and is evenly distributed in watch-glass, terminating reaction heat 3h at 280 DEG C after, be cooled to room temperature, obtain propionic acid copper crude product.Crude product is with gc analysis after esterification is derivative, and propionic acid copper productive rate is 74.7%.
Embodiment 10:
3g Alpha-hydroxy caproic acid barium is ground and is evenly distributed in culture dish, terminates reaction heat 3h at 250 DEG C after, be cooled to room temperature, obtain valeric acid barium crude product.Crude product is with gc analysis after esterification is derivative, and valeric acid barium productive rate is 79.6%.
Embodiment 11:
1g Alpha-hydroxy zinc octoate ground and is evenly distributed in watch-glass, terminating reaction heat 2h at 270 DEG C after, be cooled to room temperature, obtain Zinc Heptylate crude product.Crude product is with gc analysis after esterification is derivative, and Zinc Heptylate productive rate is 72.8%.
Embodiment 12:
Sour for 2g Alpha-hydroxy 20 lithium ground and is evenly distributed in culture dish, terminating reaction heat 3h at 260 DEG C after, be cooled to room temperature, obtain nonadecanoic acid lithium crude product.Crude product is with gc analysis after esterification is derivative, and nonadecanoic acid lithium productive rate is 80%.
Embodiment 13:
1g Alpha-hydroxy behenic acid strontium is ground and is evenly distributed in watch-glass, terminates reaction heat 3h at 260 DEG C after, be cooled to room temperature, obtain heneicosoic acid strontium crude product.Crude product is with gc analysis after esterification is derivative, and heneicosoic acid strontium productive rate is 80%.
Embodiment 14:
5g Alpha-hydroxy tetracosanoic acid potassium is ground and is evenly distributed in culture dish, terminates reaction heat 2.5h at 255 DEG C after, be cooled to room temperature, obtain tricosanic acid potassium crude product.Crude product is with gc analysis after esterification is derivative, and tricosanic acid potassium productive rate is 69.8%.
Embodiment 15:
1g Alpha-hydroxy cobalt decanoate ground and is evenly distributed in watch-glass, terminating reaction heat 4h at 235 DEG C after, be cooled to room temperature, obtain n-nonanoic acid cobalt crude product.Crude product is with gc analysis after esterification is derivative, and n-nonanoic acid cobalt productive rate is 70.6%.
Embodiment 16:
1g Alpha-hydroxy palmitic acid magnesium is ground and is evenly distributed in culture dish, terminates reaction heat 5h at 255 DEG C after, be cooled to room temperature, obtain pentadecanoic acid magnesium crude product.Crude product is with gc analysis after esterification is derivative, and pentadecanoic acid magnesium productive rate is 75.3%.
Embodiment 17:
After strongly acidic styrene's type Zeo-karb being carried out the process in conventional early stage such as pickling and washing, dress post is for subsequent use.Getting margaric acid sodium that 10g embodiment 8 prepares, to be dissolved in 150mL volume percent be in 95% ethanol, stirs 3h make dissolving complete at 55 DEG C of lower magnetic force agitators.Cross cationic exchange coloum by after the cooling of the ethanolic soln of above-mentioned margaric acid sodium, effluent liquid is through rotary evaporation, and residue obtains the thick product of 8.9g margaric acid again after vacuum-drying.
Embodiment 18:
Pentadecanoic acid potassium is prepared according to embodiment 7.Get 15g pentadecanoic acid potassium 50mL massfraction be 5% hydrochloric acid be adjusted to about pH=2 acidifying 3h, then three extractions are divided with the ether of 50mL, merge the ether layer that separatory obtains, after vacuum-drying, obtain the thick product of 10.1g pentadecanoic acid again through Distillation recovery ether, residue.
The Alpha-hydroxy used in embodiment even carbon fatty acid metallic soap raw material is all according to Chinese invention patent ZL200810021288.5, and the method recorded in the Chinese invention patent file of application number 201110072181.5 prepares.
Claims (8)
1. one kind to be reduced the synthetic method of the strange carbon fatty acid metallic soap of a carbon atom and a hydroxyl than this raw material for raw material preparation with the even carbon fatty acid metallic soap of Alpha-hydroxy, it is characterized in that the even carbon fatty acid metallic soap of raw material Alpha-hydroxy reacting by heating 1 ~ 5h under 200 ~ 300 DEG C of conditions, obtain the strange carbon fatty acid metallic soap reducing by a carbon atom than raw material thus, wherein the carbonatoms of the even carbon fatty acid metallic soap of Alpha-hydroxy is the even number in 4 ~ 24; The metallic element of described metallic soap is selected from the metallic element in the first main group element, the metallic element in the second main group element except radium, any one in aluminium and the chromium in the period 4, manganese, iron, cobalt, nickel, copper, zinc metallic element.
2. method according to claim 1, is characterized in that the even carbon fatty acid metallic soap of described raw material Alpha-hydroxy is the mixture of one or more homologues with following general structure:
In formula, R is general formula is C
nh
2n+1straight chained alkyl, wherein n is the even number of 2 ~ 22; In formula, M is metallic element; In formula, m is the valency of metallic element M.
3. the general structure of the even carbon fatty acid metallic soap of raw material Alpha-hydroxy according to claim 2, is characterized in that the even number in n=10 ~ 16.
4. method according to claim 1, is characterized in that described temperature of reaction is 220 ~ 280 DEG C.
5. method according to claim 1, is characterized in that the described reaction times is 2 ~ 4h.
6. method according to claim 1, is characterized in that described product strange carbon fatty acid metallic soap is the mixture of one or more homologues with following general structure:
(RCOO)
mM
In formula, R is general formula is C
nh
2n+1straight chained alkyl, wherein n is the even number of 2 ~ 22; In formula, M is metallic element; In formula, m is the valency of metallic element M.
7. prepare a method for strange carbon fatty acid, it is characterized in that preparing strange carbon fatty acid metallic soap in accordance with the method for claim 1, then adopt ion exchange method or direct acidization to prepare corresponding strange carbon fatty acid by strange carbon fatty acid metallic soap.
8. using even for Alpha-hydroxy carbon fatty acid metallic soap as the purposes of raw material for the preparation of the strange carbon fatty acid metallic soap and strange carbon fatty acid thereof that reduce a carbon atom and a hydroxyl than raw material, the carbonatoms of the even carbon fatty acid metallic soap of described Alpha-hydroxy is the even number in 4 ~ 24; The metallic element of described metallic soap is selected from the metallic element in the first main group element, the metallic element in the second main group element except radium, any one in aluminium and the chromium in the period 4, manganese, iron, cobalt, nickel, copper, zinc metallic element.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1839111A (en) * | 2003-07-25 | 2006-09-27 | 普罗米蒂克生物科学公司 | Preparation of metal salts of medium-chain fatty acids |
| CN101810595A (en) * | 2009-02-25 | 2010-08-25 | 中国中化股份有限公司 | Preparation method of calcium alginate microcapsule |
| CN101991975A (en) * | 2010-12-13 | 2011-03-30 | 南京四新科技应用研究所有限公司 | Mineral oil defoaming agent and preparation method thereof |
| CN102690184A (en) * | 2011-03-24 | 2012-09-26 | 江南大学 | Method for synthesizing alpha-hydroxycarboxylic acid metallic soap by hydrolysis of alpha-halogenated carboxylic acid |
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- 2013-12-16 CN CN201310691104.7A patent/CN103724180B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1839111A (en) * | 2003-07-25 | 2006-09-27 | 普罗米蒂克生物科学公司 | Preparation of metal salts of medium-chain fatty acids |
| CN101810595A (en) * | 2009-02-25 | 2010-08-25 | 中国中化股份有限公司 | Preparation method of calcium alginate microcapsule |
| CN101991975A (en) * | 2010-12-13 | 2011-03-30 | 南京四新科技应用研究所有限公司 | Mineral oil defoaming agent and preparation method thereof |
| CN102690184A (en) * | 2011-03-24 | 2012-09-26 | 江南大学 | Method for synthesizing alpha-hydroxycarboxylic acid metallic soap by hydrolysis of alpha-halogenated carboxylic acid |
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