CN102690184B - Method for synthesizing alpha-hydroxycarboxylic acid metallic soap by hydrolysis of alpha-halogenated carboxylic acid - Google Patents
Method for synthesizing alpha-hydroxycarboxylic acid metallic soap by hydrolysis of alpha-halogenated carboxylic acid Download PDFInfo
- Publication number
- CN102690184B CN102690184B CN201110072181.5A CN201110072181A CN102690184B CN 102690184 B CN102690184 B CN 102690184B CN 201110072181 A CN201110072181 A CN 201110072181A CN 102690184 B CN102690184 B CN 102690184B
- Authority
- CN
- China
- Prior art keywords
- acid
- carboxylic acid
- halogenated carboxylic
- metallic soap
- reaction
- 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.)
- Active
Links
Abstract
The invention discloses a method for synthesizing alpha-hydroxycarboxylic acid metallic soap by hydrolysis of an alpha-halogenated carboxylic acid and belongs to the field of organic compound synthesis. The method is characterized in that a cheap and easily available alpha-halogenated carboxylic acid especially such as an alpha-chlorinated fatty acid undergoes a hydrolysis reaction in the presence of a neutral or alkalescent solid acid-binding agent and a catalyst under hydro-thermal conditions so that the corresponding alpha-hydroxycarboxylic acid metallic soap is synthesized. The method has simple and environmentally friendly processes, adopts cheap and easily available raw materials, reduces less side reactions and has a high product yield.
Description
Technical field
The present invention relates to a kind of hydrolysis
α-halogenated carboxylic acid is synthetic
αthe method of-hydroxycarboxylic acid metallic soap, belongs to organic compound synthesis technical field.
Background technology
α-hydroxycarboxylic acid is the moiety of occurring in nature animal brain and nervous tissue, is also the integral part of microorganism and plant simultaneously.Short chain
α-hydroxycarboxylic acid is widely used in the industry such as food, leather, weaving, medicine, makeup, plastics; Long-chain
α-hydroxy fatty acid is also the important industrial chemicals of a class, can as after monomer synthetic polymer for fields such as green building material, wrapping material, also can be used as Chelating Collectors for floatation of iron mineral, can also be directly used in the aspects such as medicine, makeup as additive or emulsified feedstock.Owing to being difficult at present to obtain long-chain
α-hydroxy fatty acid, therefore its application is restricted.
Technology for hydrolyzing is usually used in synthesizing
α-hydroxycarboxylic acid soap or corresponding
α-hydroxycarboxylic acid, as ordinary-pressure hydrolysis Mono Chloro Acetic Acid synthesizing of glycolate calcium or oxyacetic acid barium, but the lower reaction times of condition of normal pressure is long, and productive rate is not high; In high density highly basic (sodium hydroxide, potassium hydroxide etc.) Water Under solution
α, although productive rate improves,, contaminate environment high to equipment requirements, particularly easily there is the side reactions such as autohemagglutination in-halogenated carboxylic acid.Therefore, current hydrolysis
αthere is respectively above-mentioned drawback in the whole bag of tricks of-hydroxycarboxylic acid, causes and can not meet high yield, highly selective, quick, corrosion-free, low impurely synthetic simultaneously
α-hydroxycarboxylic acid, particularly
α-hydroxy aliphatic acid product, to meet the need of market.
Summary of the invention
The object of the invention is to solve the above-mentioned technical problem existing in prior art, provide a kind of with
α-halogenated carboxylic acid particularly
α-chlorinated fatty acid is raw material, under the hydrothermal condition of solid acid binding agent and catalyzer existence, and high yield, highly selective, quick, corrosion-free, low impurely synthetic
α-hydroxycarboxylic acid metallic soap.
For achieving the above object, the technical solution used in the present invention is as follows:
Hydrolysis of the present invention
α-halogenated carboxylic acid is synthetic
αthe method of-hydroxycarboxylic acid metallic soap, with
α-halogenated carboxylic acid particularly
α-chlorinated fatty acid is raw material, hydrolysis under the hydro-thermal reaction of solid acid binding agent and catalyzer existence
α-hydroxycarboxylic acid metallic soap, synthetic route is as follows:
In formula, R is that general formula is C
nh
2n+1straight or branched alkyl, n=0 ~ 28 wherein, preferably n=8 ~ 16; M is alkaline-earth metal and zinc, cadmium, aluminium or lead except radium, the valency that m is M; B is hydroxide radical, carbonate and bicarbonate radical, the valency that b is B.
The present invention is synthetic
αthe concrete technology of the method for-hydroxycarboxylic acid metallic soap is as follows: by raw material
α-halogenated carboxylic acid and solid acid binding agent and the abundant ground and mixed of catalyzer, press
α-halogenated carboxylic acid: solid acid binding agent is 1: 1 ~ 20 mol ratio,
α-halogenated carboxylic acid: the mass ratio that catalyzer is 1: 0.01,
α-halogenated carboxylic acid: water is that 1: 1 ~ 50 mass ratio drops in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 0.5 ~ 15 h under 105 ~ 300 ℃ of hydrothermal conditions, is cooled to room temperature, and the filtering medium that suction filtration is removed after filtrate is
α-alcohol acid metallic soap crude product, crude product dehydrated alcohol thermosol, removes alcohol-insoluble substance while hot, and recrystallization obtains
α-hydroxycarboxylic acid metallic soap sterling.
Described
αthe total number of carbon atoms of-halogenated carboxylic acid is C
2~ C
30, general structure is:
In formula, R is that general formula is C
nh
2n+1straight or branched alkyl, n=0 ~ 28 wherein, preferably n=8 ~ 16; X is Cl, Br or I, preferably Cl.
The general structure of described solid acid binding agent is: (M)
b(B)
m, wherein M is alkaline-earth metal and zinc, cadmium, aluminium or lead except radium, the valency that m is M; B is hydroxide radical, carbonate and bicarbonate radical, the valency that b is B.
Described catalyzer is sodium iodide or potassiumiodide.
Described product
αthe general structure of-hydroxycarboxylic acid metallic soap is:
In formula, R is that general formula is C
nh
2n+1straight or branched alkyl, wherein n=0 ~ 28, are preferably n=8 ~ 16, M is alkaline-earth metal and zinc, cadmium, aluminium or lead except radium, the valency that m is M.
By carboxylic acid metal's soap, preparing corresponding carboxylic acid is the process that industry practitioner knows, can be simply by ion exchange method or directly acidization or other method from
α-hydroxycarboxylic acid metallic soap prepares accordingly
α-hydroxycarboxylic acid.
The present invention adopts cheap and easy to get
α-halogenated carboxylic acid, particularly
α-chlorinated fatty acid is raw material, and neutrality or weakly alkaline solid acid binding agent, catalyzer and hydrothermal condition are combined, synthetic through hydrolysis reaction
α-hydroxycarboxylic acid metallic soap, further processing can obtain highly purified
α-hydroxycarboxylic acid, can reach high yield, highly selective, quick, corrosion-free, low impurely synthetic
αthe object of-hydroxycarboxylic acid.When at hydrothermal condition with while having solid acid binding agent and catalyzer to exist,
α-halogenated carboxylic acid can generate by high productivity through saponification and hydrolysis reaction
α-hydroxycarboxylic acid metallic soap, this be because: (1) neutral or weakly alkaline solid acid binding agent can not cause corrosion to equipment, can, to environment, can not cause the side reactions such as autohemagglutination thereby have highly selective; (2) product
α-hydroxycarboxylic acid metallic soap especially
α-hydroxy fatty acid metallic soap is easily separated out from water, and by product chlorination metal-salt is soluble in water, thereby impels this hydrolysis reaction balance to move right; (3) catalyzer and high hydro-thermal can have been accelerated hydrolysis reaction speed greatly.Therefore the thermodynamic effects that the kinetic effect that the present invention produces at the high hydro-thermal energy that hydrothermal condition is caused, catalyzer and neutrality or alkalescent solid acid binding agent produce organically combines, and uses cheap and simple
α-halogenated carboxylic acid raw material, just can high yield, highly selective, quick, corrosion-free, low impurely synthetic
α-hydroxycarboxylic acid.
The beneficial effect of the invention is as follows:
(1) the present invention replaces the strong acid and strong base in traditional technology with neutral or weakly alkaline solid acid binding agent, has greatly improved selectivity and the equilibrium yield of reaction, has greatly reduced equipment corrosion and problem of environmental pollution.
(2) the present invention adopts catalyzer and hydrothermal condition, has greatly shortened the reaction times, has improved reaction yield simultaneously.
(3) products therefrom of the present invention is easy to separation, purifying.
(4) the present invention makes reaction raw materials with alkaline-earth metal, chloro higher fatty acid, and raw materials cost is cheap, is conducive to the high added value Green Development utilization of a large amount of natural fats and oils.
Embodiment
The present invention is carried out the description of embodiment below, embodiment is as follows:
Embodiment 1
αsynthesizing of-hydroxy octadecadienoic acid calcium
Press
α-chloro stearic acid: the mol ratio that calcium carbonate is 1: 3,
α-chloro stearic acid: the mass ratio that potassiumiodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-chloro stearic acid: the mass ratio that water is 1: 10 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 4 h under 155 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxy octadecadienoic acid calcium is 95.9%.
Comparative example 1: reinforcing body acid binding agent not
Press
α-chloro stearic acid: the mass ratio that potassiumiodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-chloro stearic acid: the mass ratio that water is 1: 10 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 4 h under 155 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxy octadecadienoic acid is only 45.5%.
Comparative example 2: do not add catalyzer
Press
α-chloro stearic acid: the mol ratio that calcium carbonate is 1: 3 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-chloro stearic acid: the mass ratio that water is 1: 10 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 4 h under 155 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxy octadecadienoic acid calcium is 78.9%.
Comparative example 3: ordinary-pressure hydrolysis condition
Press
α-chloro stearic acid: the mol ratio that calcium carbonate is 1: 3,
α-chloro stearic acid: the mass ratio that potassiumiodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs reactor into, presses
α-chloro stearic acid: the mass ratio that water is 1: 10 adds water in reactor reacts after 4 h and finishes reaction under reflux conditions, records
αthe productive rate of-hydroxy octadecadienoic acid calcium is only 29.6%.
Embodiment 2
αsynthesizing of-Hydroxyoctanoic acid magnesium
Press
α-chloro is sad: the mol ratio that magnesiumcarbonate is 1: 20,
α-chloro is sad: the mass ratio that potassiumiodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-chloro is sad: the mass ratio that water is 1: 10 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 4 h under 200 ℃ of hydrothermal conditions, records
αthe productive rate of-Hydroxyoctanoic acid magnesium is 97.3%.
Embodiment 3
αsynthesizing of-hydroxyl dodecanoic acid calcium
Press
α-chloro laurostearic acid: the mol ratio that calcium carbonate is 1: 20,
α-chloro laurostearic acid: the mass ratio that sodium iodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-chloro laurostearic acid: the mass ratio that water is 1: 30 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 9 h under 290 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxyl dodecanoic acid calcium is 99.3%.
Synthesizing of embodiment 4 calcium lactates
Press
α-iodo propionic acid: the mol ratio that calcium carbonate is 1: 3,
α-iodo propionic acid: the mass ratio that potassiumiodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-iodo propionic acid: the mass ratio that water is 1: 4 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 9 h under 150 ℃ of hydrothermal conditions, and the productive rate that records calcium lactate is 99.1%.
Embodiment 5
αsynthesizing of-hydroxyl triacontanoic acid zinc
Press
α-bromo triacontanoic acid: the mol ratio that zinc carbonate is 1: 20,
α-bromo triacontanoic acid: the mass ratio that sodium iodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-bromo triacontanoic acid: the mass ratio that water is 1: 40 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 7 h under 105 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxyl triacontanoic acid zinc is 94.9%.
Embodiment 6
αsynthesizing of-oxyacetic acid lead
By Mono Chloro Acetic Acid: the mol ratio that lead carbonate is 1: 1, Mono Chloro Acetic Acid: the mass ratio that potassiumiodide is 1: 0.01 takes each reaction mass, to the above abundant ground and mixed of each reaction mass and pack hydrothermal reaction kettle into, by Mono Chloro Acetic Acid: the mass ratio that water is 1: 30 adds water in hydrothermal reaction kettle, tighten kettle cover, react 15 h under 250 ℃ of hydrothermal conditions after, finish reaction, the productive rate that records oxyacetic acid lead is 90.8%.
Embodiment 7
αsynthesizing of-hydroxy-palmitic acid calcium
Press
α-iodo palmitic acid: the mol ratio that Calcium hydrogen carbonate is 1: 10,
α-iodo palmitic acid: the mass ratio that potassiumiodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-iodo palmitic acid: the mass ratio that water is 1: 25 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 7 h under 200 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxy-palmitic acid calcium is 97.5%.
Embodiment 8
αsynthesizing of-hydroxy-palmitic acid
Press
α-chloro palmitic acid: the mol ratio that calcium hydroxide is 1: 18,
α-chloro palmitic acid: the mass ratio that sodium iodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-chloro palmitic acid: the mass ratio that water is 1: 40 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 13 h under 280 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxy-palmitic acid calcium is 99.5%.Will
α-hydroxy-palmitic acid calcium is made into 95% aqueous ethanolic solution, through ion-exchange, can obtain
αthe thick product of-hydroxy-palmitic acid, can obtain purity through sherwood oil (60-90 ℃) recrystallization and be greater than 99%
α-hydroxy-palmitic acid.
Embodiment 9
αsynthesizing of-hydroxy tetradecanoic acid cadmium
Press
α-iodo TETRADECONIC ACID: the mol ratio that cadmium carbonate is 1: 10,
α-iodo TETRADECONIC ACID: the mass ratio that potassiumiodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-iodo TETRADECONIC ACID: the mass ratio that water is 1: 50 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 0.5 h under 300 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxy tetradecanoic acid cadmium is 87.5%.
Embodiment 10
αsynthesizing of-hydroxyl tetracosanoic acid magnesium
Press
α-chloro tetracosanoic acid: the mol ratio that magnesiumcarbonate is 1: 10,
α-chloro tetracosanoic acid: the mass ratio that potassiumiodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-chloro tetracosanoic acid: the mass ratio that water is 1: 35 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 10 h under 290 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxyl tetracosanoic acid magnesium is 98.9%.
Embodiment 11
αsynthesizing of-Hydroxyoctanoic acid calcium
Press
α-bromo is sad: the mol ratio that calcium carbonate is 1: 25,
α-bromo is sad: the mass ratio that potassiumiodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-bromo is sad: the mass ratio that water is 1: 1 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 2 h under 300 ℃ of hydrothermal conditions, records
αthe productive rate of-Hydroxyoctanoic acid calcium is 93.5%.
Embodiment 12
αsynthesizing of-hydroxy tetradecanoic acid barium
Press
α-chloro TETRADECONIC ACID: the mol ratio that barium carbonate is 1: 4,
α-chloro TETRADECONIC ACID: the mass ratio that potassiumiodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-chloro TETRADECONIC ACID: the mass ratio that water is 1: 5 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 4 h under 155 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxy tetradecanoic acid barium is 96.9%.
Embodiment 13
αsynthesizing of-hydroxy tetradecanoic acid
Press
α-bromo TETRADECONIC ACID: the mol ratio that Calcium hydrogen carbonate is 1: 2,
α-bromo TETRADECONIC ACID: the mass ratio that sodium iodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-bromo TETRADECONIC ACID: the mass ratio that water is 1: 2 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 2 h under 125 ℃ of hydrothermal conditions, and product obtains through acidifying
αthe thick product of-hydroxy tetradecanoic acid, productive rate reaches 89.7%, can obtain purity and reach 99% purified product after purification.
Embodiment 14
αsynthesizing of-hydroxyl dodecanoic acid lead
Press
α-chloro laurostearic acid: the mol ratio that lead carbonate is 1: 20,
α-chloro laurostearic acid: the mass ratio that sodium iodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-chloro laurostearic acid: the mass ratio that water is 1: 30 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 9 h under 290 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxyl dodecanoic acid lead is 99.0%.
Embodiment 15
αsynthesizing of-hydroxyl dodecanoic acid zinc
Press
α-chloro laurostearic acid: the mol ratio that zinc carbonate is 1: 20,
α-chloro laurostearic acid: the mass ratio that sodium iodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-chloro laurostearic acid: the mass ratio that water is 1: 30 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 9 h under 290 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxyl dodecanoic acid zinc is 99.1%.
Embodiment 16
αsynthesizing of-hydroxyl dodecanoic acid aluminium
Press
α-chloro laurostearic acid: the mol ratio that aluminium carbonate is 1: 20,
α-chloro laurostearic acid: the mass ratio that sodium iodide is 1: 0.01 takes each reaction mass, incites somebody to action the above abundant ground and mixed of each reaction mass and packs hydrothermal reaction kettle into, presses
α-chloro laurostearic acid: the mass ratio that water is 1: 30 adds water in hydrothermal reaction kettle, tightens kettle cover, finishes reaction after reacting 9 h under 290 ℃ of hydrothermal conditions, records
αthe productive rate of-hydroxyl dodecanoic acid aluminium is 99.0%.
Claims (3)
1. a hydrolysis
α-halogenated carboxylic acid is synthetic
αthe method of-hydroxycarboxylic acid metallic soap, is characterized in that: with
α-halogenated carboxylic acid is raw material, and the reaction that is hydrolyzed under the hydrothermal condition of solid acid binding agent and catalyzer existence, obtains
α-hydroxycarboxylic acid metallic soap, concrete steps are: will
α-halogenated carboxylic acid and solid acid binding agent and catalyzer ground and mixed, press
α-halogenated carboxylic acid: solid acid binding agent is 1: 1 ~ 20 mol ratio,
α-halogenated carboxylic acid: the mass ratio that catalyzer is 1: 0.01,
α-halogenated carboxylic acid: water is 1: 1 ~ 50 mass ratio, finishes reaction after reacting 0.5 ~ 15 h under 105 ~ 300 ℃ of hydrothermal conditions, is cooled to room temperature, and the filtering medium after filtering liquid is
α-hydroxycarboxylic acid metallic soap crude product;
The general structure of described solid acid binding agent is: (M)
b(B)
m, wherein M is alkaline-earth metal except radium and any one in zinc, cadmium or lead, the valency that m is M; B is any one in hydroxide radical, carbonate, the valency that b is B;
Described catalyzer is sodium iodide or potassiumiodide.
2. hydrolysis according to claim 1
α-halogenated carboxylic acid is synthetic
αthe method of-hydroxycarboxylic acid metallic soap, is characterized in that: described
αthe general structure of-halogenated carboxylic acid is:
In formula, R is that general formula is C
nh
2n+1straight or branched alkyl, n=0 ~ 28 wherein, X is Cl, Br or I.
3. hydrolysis claimed in claim 1
α-halogenated carboxylic acid is synthetic
αthe method of-hydroxycarboxylic acid metallic soap, is characterized in that: described product
αthe general structure of-hydroxycarboxylic acid metallic soap is:
In formula, R is that general formula is C
nh
2n+1straight or branched alkyl, n=0 ~ 28 wherein, M is alkaline-earth metal and zinc, cadmium or lead except radium, the valency that m is M.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110072181.5A CN102690184B (en) | 2011-03-24 | 2011-03-24 | Method for synthesizing alpha-hydroxycarboxylic acid metallic soap by hydrolysis of alpha-halogenated carboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110072181.5A CN102690184B (en) | 2011-03-24 | 2011-03-24 | Method for synthesizing alpha-hydroxycarboxylic acid metallic soap by hydrolysis of alpha-halogenated carboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102690184A CN102690184A (en) | 2012-09-26 |
| CN102690184B true CN102690184B (en) | 2014-04-30 |
Family
ID=46855940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110072181.5A Active CN102690184B (en) | 2011-03-24 | 2011-03-24 | Method for synthesizing alpha-hydroxycarboxylic acid metallic soap by hydrolysis of alpha-halogenated carboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102690184B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012112A (en) * | 2012-12-06 | 2013-04-03 | 江苏大学 | Method for preparing lactic acid through hydrolysis of alpha-chloropropionic acid |
| CN103724180B (en) * | 2013-12-16 | 2015-10-21 | 江南大学 | A kind of method preparing strange carbon fatty acid metallic soap and strange carbon fatty acid thereof |
| CN106496012B (en) * | 2016-10-08 | 2019-03-22 | 张家港市华昌药业有限公司 | A kind of preparation method of Alpha-hydroxy tetradecylic acid |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101434557A (en) * | 2007-11-13 | 2009-05-20 | 科兹莫弗姆有限公司 | Derivative of short chain 2-hydroxy carboxylic acid of ceramide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4423494B2 (en) * | 2003-07-17 | 2010-03-03 | 東レ・ファインケミカル株式会社 | Method for producing 2-hydroxycarboxylic acid |
-
2011
- 2011-03-24 CN CN201110072181.5A patent/CN102690184B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101434557A (en) * | 2007-11-13 | 2009-05-20 | 科兹莫弗姆有限公司 | Derivative of short chain 2-hydroxy carboxylic acid of ceramide |
Non-Patent Citations (1)
| Title |
|---|
| JP特开2005-35904A 2005.02.10 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102690184A (en) | 2012-09-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102875594B (en) | Continuous synthesis technique of hydroxyethylidenediphosphonic acid | |
| CN1814583A (en) | Method for preparing 2-P-octyl-phenenl-2-amino-propanediol hydrochloride | |
| CN102690184B (en) | Method for synthesizing alpha-hydroxycarboxylic acid metallic soap by hydrolysis of alpha-halogenated carboxylic acid | |
| CN109232178B (en) | Novel method for preparing high-purity hydroxytyrosol | |
| CN101391956B (en) | Method for synthesizing methyl oleate and epoxy methyl oleate in ion liquid medium | |
| CN111393331B (en) | Preparation method of glycocyamine | |
| CN109305912B (en) | Method for preparing 2,2, 4-trimethyl-1, 3-pentanediol monoisobutyrate by condensing isobutyraldehyde | |
| CN109134215B (en) | Production method for preparing trimethyl orthoformate by liquid metal sodium slag method | |
| CN101450895A (en) | Process for producing trifluoro benzene acetic acid | |
| CN101113153A (en) | Process for the preparation of boronic acids and derivatives thereof | |
| CN107814697A (en) | A kind of preparation method of n Propanoic acid chromium | |
| CN110713439A (en) | Preparation method of cyclohexane-1, 2-dicarboxylate environment-friendly plasticizer | |
| CN1317255C (en) | Method for synthesizing high-recovery and high-optical purity L-butyl lactate | |
| CN101973870B (en) | Preparation of glycollic acid from oxalaldehyde by intramolecular disproportionation method | |
| CN101967081B (en) | Process for recovering water-containing methanol solution produced in production of antioxygen 1010 | |
| CN103224444A (en) | Method for synthesizing 3-methyl-3-butenyl-1-ol by two-step process | |
| CN108640813B (en) | Method for synthesizing terpineol/terpinyl acetate from turpentine | |
| CN101333159B (en) | Method for synthesizing alpha, beta-unsaturated fatty acid from alpha-chloro-fatty acid | |
| CN101665426A (en) | Method for preparing 2-alkyl carboxylic acid | |
| CN101402570B (en) | Method of preparing 5-methyl-5-hexenoic acid ethyl ester | |
| CN113943221B (en) | Method for preparing formic acid-2-methyl allyl ester from paraformaldehyde and methacrolein | |
| CN1698942A (en) | Chelated surfacant | |
| CN101716521A (en) | Preparation method of inorganic solid catalyst for synthesizing dimethyl maleate | |
| CN108069897B (en) | Method for synthesizing nicotinic acid by using carbon dioxide | |
| CN113277990A (en) | Synthesis method of 1, 4-bis (p-toluenesulfonyl) triazacyclononane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20120926 Assignee: Jiangsu Prov. Ceramic Research Inst. Co., Ltd. Assignor: Jiangnan University Contract record no.: 2017410000003 Denomination of invention: Method for synthesizing alpha-hydroxycarboxylic acid metallic soap by hydrolysis of alpha-halogenated carboxylic acid Granted publication date: 20140430 License type: Common License Record date: 20170122 |
|
| EE01 | Entry into force of recordation of patent licensing contract |