CN106008206A - Method for dodecylamine phosphotungstate catalyzed synthesis of long-chain carboxylate - Google Patents
Method for dodecylamine phosphotungstate catalyzed synthesis of long-chain carboxylate Download PDFInfo
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- CN106008206A CN106008206A CN201610376026.5A CN201610376026A CN106008206A CN 106008206 A CN106008206 A CN 106008206A CN 201610376026 A CN201610376026 A CN 201610376026A CN 106008206 A CN106008206 A CN 106008206A
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- acid
- lauryl amine
- higher fatty
- phosphotungstic acid
- fatty ester
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0237—Amines
- B01J31/0238—Amines with a primary amino group
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/34—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of chromium, molybdenum or tungsten
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/49—Esterification or transesterification
Abstract
The invention provides a method for dodecylamine phosphotungstate catalyzed synthesis of long-chain carboxylate. The long-chain carboxylate is synthesized from carboxylic acid and long-chain fatty alcohol under the catalysis of dodecylamine phosphotungstate, the structural formula of the dodecylamine phosphotungstate is (C12H25NH3)XH3-XPW12O40, X is not smaller than 0.5 and not greater than 1, and the dodecylamine phosphotungstate is loaded on a carrier. The carboxylic acid is adipic acid, pimelic acid, citric acid or acetylpropionic acid preferably, and the long-chain fatty alcohol is C4-C12 linear or branched alcohol preferably. The method has the advantages of realization of good dispersion, high effective utilization and difficult loss of an active component in the above catalyst, high product yield, easy separation of the catalyst and the product, and excellent reuse performance of the catalyst.
Description
Technical field
The present invention relates to catalyze and synthesize the method for higher fatty ester, catalyze and synthesize particularly to a kind of phosphotungstic acid lauryl amine salt
The method of higher fatty ester.
Background technology
Esterification is the unit process that the class in organic synthesis is important.In traditional method, often with sulphuric acid, phosphoric acid
Being catalyst with liquid acid such as p-methyl benzenesulfonic acid, there is catalyst separates difficulty with product, and energy consumption is higher, etching apparatus and pollution
The problems such as environment.At present, the solid acid catalyst being applied to esterification of document report includes: metal-oxide, solid are super
Strong acid, acidic resins, molecular sieve and heteropoly acid etc..Wherein, heteropoly acid has green non-poisonous, the acid strong and high spy of selectivity
Point, the catalyst as esterification the most industrially obtains application.But, heteropoly acid there is also and is soluble in polar reaction Jie
The problem such as matter, specific surface area be low and heat stability is poor.Therefore, research worker develops following two solution: 1, may be used
The loaded by heteropoly acid of dissolubility on the catalytic carrier of high-specific surface area (CN103586056, CN103586057, CN103586058,
CN103586059, CN103586076, CN103586077 and CN102962084)；2, the heteropoly acid of solubility is changed into not
The heteropoly acid saline catalyst of dissolubility (CN105061204, CN100430319 and Wang Wei, Master's thesis, Qingdao University of Science and Technology,
2013).The catalyst of employing scheme 1 preparation has the advantages such as specific surface area is high, active component is uniformly dispersed, catalytic efficiency is high,
But the problem that the active component that there is solubility is easy to run off；The catalyst of employing scheme 2 preparation has Stability Analysis of Structures, active component
The advantage not easily runed off, but there is the problem that specific surface area is little and catalytic efficiency is relatively low.
For the advantage of association scheme 1 with scheme 2, heteropoly acid salt active component is supported on high-ratio surface by research worker
On long-pending carrier, and it is applied in catalytic esterification.But, insoluble due to heteropolyacid salt used, loading
Cheng Zhong, is difficult to be highly dispersed at the surface of catalytic carrier, makes the effective rate of utilization of active component still need to further and promote.Cause
This, improve the active component heteropolyacid salt dispersibility at carrier surface, it is thus achieved that has high activity and the load of excellent stability energy
Type heteropoly acid saline catalyst, to improve yield and the efficiency of synthesis higher fatty ester, remains those skilled in the art anxious
Need to solve the technical problem that.
Summary of the invention
It is an object of the invention to provide a kind of method that phosphotungstic acid lauryl amine salt catalyzes and synthesizes higher fatty ester, the method
Having yield high, catalyst amount is few, and catalyst is easily isolated and can stable realization reuse.
The method that the phosphotungstic acid lauryl amine salt that the present invention provides catalyzes and synthesizes higher fatty ester, with carboxylic acid and long-chain fatty alcohol
Synthesize under the catalytic action of phosphotungstic acid lauryl amine salt for raw material and obtain higher fatty ester, wherein, described phosphotungstic acid lauryl amine salt
Skeleton symbol be: (C12H25NH3)XH3-XPW12O40, 0.5≤X≤1, described phosphotungstic acid lauryl amine salt is carried on carrier.
Further, described carboxylic acid is adipic acid, 1,5-pentanedicarboxylic acid., citric acid or levulic acid, and described long-chain fatty alcohol is
C4—C12Straight or branched alcohol.
Further, described carrier is MCM-41, SBA-15, Al2O3Or SiO2。
Further, the preparation process of phosphotungstic acid lauryl amine salt catalyst includes step:
(1) solution of lauryl amine is mixed with the solution of phosphotungstic acid；
(2) carrier is mixed with step (1) gained solution；
(3) solvent is removed, and by gained solid roasting.
Further, during described step (1) is specially the aqueous solution that the ethanol solution of lauryl amine drops to phosphotungstic acid.
Further, in described step (1), the ratio of described lauryl amine and the amount of the material of described phosphotungstic acid be 0.5:1～
1:1.
Further, described phosphotungstic acid is 0.3:1～1:1 with the mass ratio of described carrier.
Further, in described step (3), sintering temperature is 150～250 DEG C.
Phosphotungstic acid lauryl amine salt (C involved in the present invention12H25NH3)XH3-XPW12O40, 0.5≤X≤1, have solubility concurrently
Characteristic with insoluble heteropolyacid salt: the phosphotungstic acid lauryl amine salt containing absorption water with water of crystallization of fabricated in situ dissolves in ethanol
In equal solvent so that it is be prone to be highly dispersed at carrier surface in loading process；After fired removal absorption water and water of crystallization,
The phosphotungstic acid lauryl amine salt arrived is then insoluble in organic solvents such as methanol, ethanol, butanol and isooctanol so that it is can be stable in the presence of
Carrier surface, will not occur solution-off in catalytic reaction process.Additionally, containing oleophylic in the molecular structure of phosphotungstic acid lauryl amine salt
The preferable dodecyl group of property, has preferable affinity to long-chain fatty alcohol.Therefore, the technical scheme tool that the present invention provides
Having the advantage that the good dispersion of active component in catalyst, effective rate of utilization is high and not easily runs off, and product yield is high, catalysis
Agent is easily separated with product, and the repeat performance of catalyst is excellent.
Detailed description of the invention
Below the detailed description of the invention of the present invention is described in further detail.For those of skill in the art
For Yuan, from detailed description of the invention, the above and other objects, features and advantages of the present invention will be apparent to.
Embodiment 1
The preparation of catalyst: under conditions of room temperature is continuously stirred, slowly will drip containing the ethanol solution of 0.0005mol lauryl amine
Enter containing 0.001 mol phosphotungstic acid (H3PW12O40) aqueous solution in, add 5 g MCM-41, continuously stirred, at 80 DEG C
Evaporative removal etoh solvent and water, at 200 DEG C of roasting 4 h, gained solid is MCM-41 load phosphotungstic acid lauryl amine salt.
Embodiment 2
The preparation of catalyst: under conditions of room temperature is continuously stirred, slowly will drip containing the ethanol solution of 0.001mol lauryl amine
Enter containing 0.001 mol phosphotungstic acid (H3PW12O40) aqueous solution in, add 5 g SiO2, continuously stirred, steam at 80 DEG C
Sending out and remove etoh solvent and water, at 200 DEG C of roasting 4 h, gained solid is SiO2Load phosphotungstic acid lauryl amine salt.
Embodiment 3
The preparation of catalyst: under conditions of room temperature is continuously stirred, will be slowly dropped into containing the methanol solution of 0.0005mol lauryl amine
Containing 0.001 mol phosphotungstic acid (H3PW12O40) aqueous solution in, add 10 g SBA-15, continuously stirred, at 80 DEG C steam
Sending out and remove etoh solvent and water, at 200 DEG C of roasting 4 h, gained solid is SBA-15 load phosphotungstic acid lauryl amine salt.
Embodiment 4
The preparation of catalyst: under conditions of room temperature is continuously stirred, slowly will drip containing the ethanol solution of 0.0005mol lauryl amine
Enter containing 0.001 mol phosphotungstic acid (H3PW12O40) aqueous solution in, add 3.1 g Al2O3, continuously stirred, at 80 DEG C
Evaporative removal etoh solvent and water, at 200 DEG C of roasting 4 h, gained solid is MCM-41 load phosphotungstic acid lauryl amine salt.
Embodiment 5
The preparation of catalyst: under conditions of room temperature is continuously stirred, slowly will drip containing the ethanol solution of 0.0005mol lauryl amine
Enter containing 0.001 mol phosphotungstic acid (H3PW12O40) aqueous solution in, add 5 g MCM-41, continuously stirred, at 80 DEG C
Evaporative removal etoh solvent and water, at 150 DEG C of roasting 4 h, gained solid is MCM-41 load phosphotungstic acid lauryl amine salt.
Embodiment 6
The preparation of catalyst: under conditions of room temperature is continuously stirred, slowly will drip containing the ethanol solution of 0.0005mol lauryl amine
Enter containing 0.001 mol phosphotungstic acid (H3PW12O40) aqueous solution in, add 5 g MCM-41, continuously stirred, at 80 DEG C
Evaporative removal etoh solvent and water, at 250 DEG C of roasting 4 h, gained solid is MCM-41 load phosphotungstic acid lauryl amine salt.
Embodiment 7
By 0.05mol adipic acid, 0.15mol isooctanol, 5mL water entrainer hexamethylene is negative with the MCM-41 of 0.2g embodiment 1 preparation
Carry phosphotungstic acid lauryl amine salt catalyst to add in 100 mL there-necked flasks, assemble thermometer, condensing tube and water knockout drum, be heated to
165 DEG C, after reacting 1.5 h, cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is according to GB/T
1668-2008 is carried out, and esterification yield is 99.0%.
Embodiment 8
By 0.05mol adipic acid, 0.15mol isooctanol, the SiO that 5mL water entrainer hexamethylene is prepared with 0.2g embodiment 22Load
Phosphotungstic acid lauryl amine salt catalyst adds in 100 mL there-necked flasks, assembles thermometer, condensing tube and water knockout drum, is heated to
165 DEG C, after reacting 1.5 h, cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is according to GB/T
1668-2008 is carried out, and esterification yield is 96.8%.
Embodiment 9
By 0.05 mol adipic acid, 0.15 mol isooctanol, 5 mL water entrainer hexamethylene and the SBA-of 0.2 g embodiment 3 preparation
15 load phosphotungstic acid lauryl amine salt catalysts add in 100 mL there-necked flasks, assemble thermometer, condensing tube and water knockout drum, add
Heat is to 165 DEG C, and after reacting 1.5 h, cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is according to GB/T
1668-2008 is carried out, and esterification yield is 90.5%.
Embodiment 10
By 0.05 mol adipic acid, 0.15 mol isooctanol, 5 mL water entrainer hexamethylene and the Al of 0.2 g embodiment 4 preparation2O3
Load phosphotungstic acid lauryl amine salt catalyst adds in 100 mL there-necked flasks, assembles thermometer, condensing tube and water knockout drum, heating
To 165 DEG C, after reacting 1.5 h, cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is according to GB/T
1668-2008 is carried out, and esterification yield is 99.8%.
Embodiment 11
By 0.05 mol adipic acid, 0.15 mol isooctanol, 5 mL water entrainer hexamethylene and the MCM-of 0.2 g embodiment 5 preparation
41 load phosphotungstic acid lauryl amine salt catalysts add in 100 mL there-necked flasks, assemble thermometer, condensing tube and water knockout drum, add
Heat is to 165 DEG C, and after reacting 1.5 h, cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is according to GB/T
1668-2008 is carried out, and esterification yield is 98.5%.
Embodiment 12
By 0.05 mol adipic acid, 0.15 mol isooctanol, 5 mL water entrainer hexamethylene and the MCM-of 0.2 g embodiment 6 preparation
41 load phosphotungstic acid lauryl amine salt catalysts add in 100 mL there-necked flasks, assemble thermometer, condensing tube and water knockout drum, add
Heat is to 165 DEG C, and after reacting 1.5 h, cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is according to GB/T
1668-2008 is carried out, and esterification yield is 99.2%.
Embodiment 13
By 0.05 mol adipic acid, 0.15 mol n-butyl alcohol and the MCM-41 load phosphotungstic acid lauryl amine of 0.2 g embodiment 1 preparation
Salt catalyst adds in 100 mL there-necked flasks, assembles thermometer, condensing tube and water knockout drum, is heated to 140 DEG C, reacts 2 h
After, cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is carried out according to GB/T 1668-2008, esterification
Rate is 95.6%.
Embodiment 14
By 0.05 mol adipic acid, 0.15 mol n-octyl alcohol, 5 mL water entrainer hexamethylene and the MCM-of 0.2 g embodiment 1 preparation
41 load phosphotungstic acid lauryl amine salt catalysts add in 100 mL there-necked flasks, assemble thermometer, condensing tube and water knockout drum, add
Heat is to 165 DEG C, and after reacting 1 h, cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is according to GB/T
1668-2008 is carried out, and esterification yield is 99.2%.
Embodiment 15
By 0.05 mol adipic acid, 0.15 mol lauryl alcohol, 5 mL water entrainer hexamethylene and the MCM-of 0.2 g embodiment 1 preparation
41 load phosphotungstic acid lauryl amine salt catalysts add in 100 mL there-necked flasks, assemble thermometer, condensing tube and water knockout drum, add
Heat is to 190 DEG C, and after reacting 2 h, cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is according to GB/T
1668-2008 is carried out, and esterification yield is 96.5%.
Embodiment 16
By 0.05 mol 1,5-pentanedicarboxylic acid., 0.15 mol isooctanol, 5 mL water entrainer hexamethylene and the MCM-of 0.2 g embodiment 1 preparation
41 load phosphotungstic acid lauryl amine salt catalysts add in 100 mL there-necked flasks, assemble thermometer, condensing tube and water knockout drum, add
Heat is to 170 DEG C, and after reacting 1.5 h, cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is according to GB/T
1668-2008 is carried out, and esterification yield is 99.1%.
Embodiment 17
By 0.1 mol citric acid, 0.4 mol n-butyl alcohol and the MCM-41 load phosphotungstic acid lauryl amine salt of 0.2 g embodiment 1 preparation
Catalyst adds in 100 mL there-necked flasks, assembles thermometer, condensing tube and water knockout drum, is heated to 150 DEG C, after reacting 3 h,
Cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is carried out according to GB/T 1668-2008, esterification yield
It is 97.1%.
Embodiment 18
By 0.1 mol citric acid, 0.4 mol lauryl alcohol, 5 mL water entrainer hexamethylene and the MCM-41 of 0.2 g embodiment 1 preparation
Load phosphotungstic acid lauryl amine salt catalyst adds in 100 mL there-necked flasks, assembles thermometer, condensing tube and water knockout drum, heating
To 190 DEG C, after reacting 3 h, cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is according to GB/T
1668-2008 is carried out, and esterification yield is 95.6%.
Embodiment 19
By 0.1 mol levulic acid, 0.2 mol n-butyl alcohol and the MCM-41 load phosphotungstic acid lauryl amine of 0.2 g embodiment 1 preparation
Salt catalyst adds in 100 mL there-necked flasks, assembles thermometer, condensing tube and water knockout drum, is heated to 120 DEG C, reacts 2 h
After, cooling, centrifugal, liquid product uses acid number method to calculate esterification yield, and acid number analysis is carried out according to GB/T 1668-2008, esterification
Rate is 99.0%.
Embodiment 20
Catalyst after using in embodiment 7, without any process after centrifugation, for the reaction of next batch, instead
Answering condition and detection method with embodiment 7, after catalyst reuses 4 times, esterification yield is 98.1%.
Although should be appreciated that the present invention has carried out understanding explanation by above example, but without departing substantially from the present invention
Spirit and essence in the case of, person of ordinary skill in the field when can according to the present invention make various corresponding change and
Revise, but these corresponding variations and modifications all should belong to the scope of the claims of the present invention.
Claims (8)
1. the method that phosphotungstic acid lauryl amine salt catalyzes and synthesizes higher fatty ester, with carboxylic acid and long-chain fatty alcohol for raw material at phosphorus
Under the catalytic action of wolframic acid lauryl amine salt, synthesis obtains higher fatty ester, it is characterised in that the knot of described phosphotungstic acid lauryl amine salt
Structure skeleton symbol is: (C12H25NH3)XH3-XPW12O40, 0.5≤X≤1, described phosphotungstic acid lauryl amine salt is carried on carrier.
The method catalyzing and synthesizing higher fatty ester the most according to claim 1, it is characterised in that described carboxylic acid be oneself two
Acid, 1,5-pentanedicarboxylic acid., citric acid or levulic acid, described long-chain fatty alcohol is C4—C12Straight or branched alcohol.
The method catalyzing and synthesizing higher fatty ester the most according to claim 1, it is characterised in that described carrier is MCM-
41、SBA-15、Al2O3Or SiO2。
4. according to the method catalyzing and synthesizing higher fatty ester described in any one of claim 1-3, it is characterised in that phosphotungstic acid ten
The preparation process of diamine salts catalyst includes step:
(1) solution of lauryl amine is mixed with the solution of phosphotungstic acid；
(2) carrier is mixed with step (1) gained solution；
(3) solvent is removed, and by gained solid roasting.
The method catalyzing and synthesizing higher fatty ester the most according to claim 4, it is characterised in that described step (1) is concrete
For the ethanol solution of lauryl amine being dropped in the aqueous solution of phosphotungstic acid.
The method catalyzing and synthesizing higher fatty ester the most according to claim 4, it is characterised in that in described step (1), institute
The ratio stating the lauryl amine amount with the material of described phosphotungstic acid is 0.5:1～1:1.
The method catalyzing and synthesizing higher fatty ester the most according to claim 4, it is characterised in that described phosphotungstic acid is with described
The mass ratio of carrier is 0.3:1～1:1.
The method catalyzing and synthesizing higher fatty ester the most according to claim 4, it is characterised in that in described step (3), roasting
Burning temperature is 150～250 DEG C.
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| CN201610376026.5A CN106008206B (en) | 2016-05-31 | 2016-05-31 | A kind of method that phosphotungstic acid lauryl amine salt catalyzes and synthesizes higher fatty ester |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107188804A (en) * | 2017-07-09 | 2017-09-22 | 邵阳学院 | A kind of method that compound phosphotungstate catalyzes and synthesizes methyl oleate |
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| CN102641746A (en) * | 2012-04-05 | 2012-08-22 | 中国科学院青岛生物能源与过程研究所 | Heteropolyacid modified catalyst, and preparation and catalyst catalytic hydrolysis reaction system thereof |
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| CN1541991A (en) * | 2003-04-29 | 2004-11-03 | 中国石油化工股份有限公司 | Hydrolysis method of esters |
| CN101574667A (en) * | 2009-06-08 | 2009-11-11 | 南京工业大学 | Solid acid catalyst, preparation thereof and application thereof in esterification reaction |
| CN102641746A (en) * | 2012-04-05 | 2012-08-22 | 中国科学院青岛生物能源与过程研究所 | Heteropolyacid modified catalyst, and preparation and catalyst catalytic hydrolysis reaction system thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107188804A (en) * | 2017-07-09 | 2017-09-22 | 邵阳学院 | A kind of method that compound phosphotungstate catalyzes and synthesizes methyl oleate |
| CN107188804B (en) * | 2017-07-09 | 2021-01-26 | 邵阳学院 | Method for catalytically synthesizing methyl oleate by using composite phosphotungstate |
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| CN106008206B (en) | 2018-10-23 |
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