CN110615738A - Epoxy fatty acid methyl ester hydrogenation modification process and hydroxyl-containing saturated fatty acid methyl ester - Google Patents
Epoxy fatty acid methyl ester hydrogenation modification process and hydroxyl-containing saturated fatty acid methyl ester Download PDFInfo
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- CN110615738A CN110615738A CN201810629212.4A CN201810629212A CN110615738A CN 110615738 A CN110615738 A CN 110615738A CN 201810629212 A CN201810629212 A CN 201810629212A CN 110615738 A CN110615738 A CN 110615738A
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- methyl ester
- fatty acid
- acid methyl
- epoxy
- hydrogenation
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- 235000019387 fatty acid methyl ester Nutrition 0.000 title claims abstract description 71
- 239000004593 Epoxy Substances 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 26
- 150000004671 saturated fatty acids Chemical class 0.000 title claims abstract description 26
- 230000004048 modification Effects 0.000 title claims abstract description 16
- 238000012986 modification Methods 0.000 title claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000035484 reaction time Effects 0.000 claims abstract description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 34
- 239000003549 soybean oil Substances 0.000 claims description 7
- 235000012424 soybean oil Nutrition 0.000 claims description 7
- 239000003921 oil Substances 0.000 claims description 6
- 235000019198 oils Nutrition 0.000 claims description 6
- QYDYPVFESGNLHU-KHPPLWFESA-N Methyl oleate Natural products CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 claims description 5
- 235000019482 Palm oil Nutrition 0.000 claims description 5
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 5
- 239000004359 castor oil Substances 0.000 claims description 5
- 235000019438 castor oil Nutrition 0.000 claims description 5
- 235000012343 cottonseed oil Nutrition 0.000 claims description 5
- 239000002385 cottonseed oil Substances 0.000 claims description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 5
- 239000002540 palm oil Substances 0.000 claims description 5
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 4
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- IMYZYCNQZDBZBQ-SJORKVTESA-N (9S,10R)-epoxyoctadecanoic acid Chemical compound CCCCCCCC[C@H]1O[C@H]1CCCCCCCC(O)=O IMYZYCNQZDBZBQ-SJORKVTESA-N 0.000 claims description 3
- 238000005056 compaction Methods 0.000 claims description 3
- 239000011148 porous material Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 238000003756 stirring Methods 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 238000007046 ethoxylation reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 238000006277 sulfonation reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- VUSHVKUNOXWQTG-KHPPLWFESA-N methyl (Z)-2-oxooctadec-9-enoate Chemical compound O=C(C(=O)OC)CCCCCC\C=C/CCCCCCCC VUSHVKUNOXWQTG-KHPPLWFESA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- -1 unsaturated fatty acid methyl ester Chemical class 0.000 description 2
- 241001550224 Apha Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012668 chain scission Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
Classifications
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
-
- B01J35/31—
-
- B01J35/615—
-
- B01J35/633—
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention discloses a hydrogenation modification process of epoxy fatty acid methyl ester. Carrying out hydrogenation process treatment on epoxy fatty acid methyl ester to obtain saturated fatty acid methyl ester containing hydroxyl; wherein the reaction temperature of the hydrogenation process is 100-150 ℃, the reaction pressure is less than or equal to 4MPa, and the reaction time is 1-4 hours; the catalyst in the hydrogenation process comprises the effective component of metallic nickel, and the carrier component of the catalyst is alumina. The invention also discloses the saturated fatty acid methyl ester containing hydroxyl obtained by the process. Compared with the prior art, the method has the advantages that although saturated fatty acid methyl ester can be obtained only by one more epoxy fatty acid methyl ester synthesis process, the finally obtained saturated fatty acid methyl ester containing hydroxyl has special efficacy, so that higher economic benefit exists in the whole surfactant production process.
Description
Technical Field
The invention belongs to the technical field of oil industrial production, and particularly relates to a hydrogenation modification process of epoxy fatty acid methyl ester and saturated fatty acid methyl ester containing hydroxyl.
Background
At present, anionic surfactant fatty acid methyl ester sulfonate MES and nonionic surfactant fatty acid methyl ester ethoxylate FMEE commonly used in the daily chemical industry are mainly synthesized by adopting saturated fatty acid methyl ester. The saturated fatty acid methyl ester is synthesized by using unsaturated fatty acid methyl ester containing carbon-carbon double bonds as a raw material through hydrogenation reaction, and the oxidation resistance stability of the fatty acid methyl ester is improved while the carbon-carbon double bonds are eliminated.
Epoxy fatty acid methyl esters are generally prepared by reacting unsaturated double bonds in fatty acid methyl esters with peroxy organic acids in the presence of catalysts, and because they contain epoxy groups, they are often used as intermediates for the production of chemicals having a variety of industrial uses. Although the iodine value in the product index of the epoxy methyl ester is reduced and the degree of unsaturation of a carbon chain is also reduced, the ring opening of the epoxy fatty acid methyl ester influences the synthesis of a target product, so that no published research data reports an industrial process for preparing a surfactant product by using the epoxy fatty acid methyl ester as a production raw material.
Disclosure of Invention
The first purpose of the invention is to provide a hydrogenation modification process of epoxidized fatty acid methyl ester, aiming at the defects of the prior art, so that the epoxidized fatty acid methyl ester can be suitable for preparing a surfactant product.
The second purpose of the invention is to provide the saturated fatty acid methyl ester containing hydroxyl prepared by the process.
In order to achieve the first purpose, the invention adopts the following technical scheme:
the hydrogenation modification process of the epoxy fatty acid methyl ester comprises the steps of carrying out hydrogenation process treatment on the epoxy fatty acid methyl ester to obtain saturated fatty acid methyl ester containing hydroxyl; wherein the reaction temperature of the hydrogenation process is 100-150 ℃, the reaction pressure is less than or equal to 4MPa, and the reaction time is 1-4 hours; the catalyst in the hydrogenation process comprises the effective component of metallic nickel, and the carrier component of the catalyst is alumina.
Further, the epoxy fatty acid methyl ester is a fatty acid methyl ester containing an epoxy group having at least one three-membered ring,
preferably, the epoxidized fatty acid methyl ester is any one of epoxidized soybean oil methyl ester, epoxidized palm oil methyl ester, epoxidized cottonseed oil methyl ester, epoxidized rapeseed oil methyl ester, epoxidized oleic acid methyl ester, epoxidized castor oil methyl ester and epoxidized hogwash oil methyl ester, or a combination of at least two of them.
Preferably, the epoxy value of the epoxidized fatty acid methyl ester is 3 to 8%.
Preferably, the BET specific surface area of the catalyst used in the hydrogenation process is 100-200m2The pore volume is 0.4-0.5mL/g, the compaction density is 700-3The average grain diameter is 2.0-3.0 mm; the mass content of the metallic nickel in the catalyst is 15-25%; the average size of the alumina is 1.0-2.0 mm.
In order to achieve the second purpose, the invention adopts the following technical scheme:
saturated fatty acid methyl ester containing hydroxyl is prepared by the hydrogenation modification process of the epoxy fatty acid methyl ester.
Compared with the prior art, the method has the advantages that although saturated fatty acid methyl ester can be obtained only by one more epoxy fatty acid methyl ester synthesis process, the finally obtained saturated fatty acid methyl ester containing hydroxyl has special efficacy, so that higher economic benefit exists in the whole surfactant production process.
Detailed Description
The invention relates to a hydrogenation modification process of epoxy fatty acid methyl ester, which is to carry out hydrogenation process treatment on the epoxy fatty acid methyl ester to obtain saturated fatty acid methyl ester containing hydroxyl.
The epoxy fatty acid methyl ester is a general commercial industrial product, and the product indexes are as follows:
| item | Standard requirements |
| Epoxy value (%) | ≥3.0，≤8.0 |
| Moisture Moisture (%) | ≤0.5 |
| Acid Value (mgKOH/g) | ≤1 |
| Color number color (APHA) | ≤30 |
| Iodine Value Iodine Value (g/150g) | ≤5 |
| Density (e20 ℃/cm3) | 0.92-0.95 |
The epoxy fatty acid methyl ester meeting the product index requirements can be any one of epoxy soybean oil methyl ester, epoxy palm oil methyl ester, epoxy cottonseed oil methyl ester, epoxy rapeseed oil methyl ester, epoxy oleic acid methyl ester, epoxy castor oil methyl ester and epoxy hogwash oil methyl ester, or the combination of at least two of the epoxy soybean oil methyl ester, the epoxy palm oil methyl ester, the epoxy cottonseed oil methyl ester, the epoxy rapeseed oil methyl ester, the epoxy oleic acid methyl ester, the epoxy castor.
The hydrogenation modification process has the following process key points:
1. hydrogenation catalyst:
the catalyst has effective component of metal nickel and carrier component of alumina. Wherein, the metallic nickel is granular, and the mass content in the catalyst is 15-25%, preferably 20%. The alumina is solid particles with an average size of 1.0-2.0 mm.
The BET specific surface area of the catalyst is 100-2The pore volume is 0.4-0.5mL/g, the compaction density is 700-3The average particle diameter is 2.0-3.0 mm.
2. A hydrogenation reactor:
a batch kettle type reactor or a tower type continuous reactor can be adopted.
3. The technological parameters are as follows:
internal pressure of the reactor: 2-4 Mpa.
The temperature of the reaction mass is 100-150 ℃.
The residence time of the reaction mass is 1-4 hours.
In the process, the reaction temperature of the hydrogenation process is low, so that the chain scission of methyl ester in epoxy fatty acid methyl ester can be avoided to generate fatty acid and methanol; the catalyst carrier alumina is an acidic carrier, which is beneficial to ring opening of an epoxy group and improvement of the reaction rate; the obtained saturated fatty acid methyl ester containing hydroxyl has higher saturation, the iodine value of the product is lower than 0.5, and the epoxy value is lower than 0.1%.
The following illustrates an example of the synthesis of a hydroxyl-containing saturated fatty acid methyl ester by the process of hydrogenating and modifying an epoxy fatty acid methyl ester:
example 1
Adding 200 g of epoxy palm oil methyl ester (epoxy value is 3.5%) and 10 g of catalyst into 500ml of high-pressure reaction kettle with an electric stirring device, a measuring thermometer and a measuring kettle in sequence, stirring and heating to 90 ℃, introducing high-purity hydrogen, maintaining the pressure of 3MPa, continuously heating to 145 ℃, reacting for 1.5 hours, stopping, and filtering the catalyst to obtain the refined saturated palm methyl ester containing hydroxyl.
Example 2
200 g of epoxidized soybean oil methyl ester (epoxy value is 3.5%) and 30 g of catalyst are sequentially added into a 500ml high-pressure reaction kettle with an electric stirring device, a measuring thermometer and a measuring kettle, the temperature is raised to 90 ℃ by stirring, high-purity hydrogen is introduced, the pressure is maintained at 3MPa, the temperature is continuously raised to 130 ℃, the reaction is stopped after 2.5 hours, and the catalyst is filtered to obtain the refined saturated soybean oil methyl ester containing hydroxyl.
Example 3
200 g of rapeseed oil methyl ester and epoxy hogwash oil methyl ester 1 are sequentially added into a 500ml reaction kettle with an electric stirring device, a measuring thermometer and a high-pressure reaction kettle: 1 (epoxy value is 5.5 percent) and 30 g of catalyst are stirred and heated to 90 ℃, high-purity hydrogen is introduced, the pressure of 3MPa is maintained, the temperature is continuously raised to 125 ℃, the reaction is stopped after 3.5 hours, and the catalyst is filtered to obtain the refined saturated fatty acid methyl ester containing hydroxyl.
Example 4
Adding 200 g of epoxy methyl oleate raw material (the epoxy value is 7.5%) and 25 g of catalyst into a 500ml high-pressure reaction kettle with an electric stirring device, a measuring thermometer and a measuring thermometer in sequence, stirring and heating to 90 ℃, introducing high-purity hydrogen, maintaining the pressure of 3MPa, continuously heating to 120 ℃, reacting for 4.0 hours, stopping, and filtering the catalyst to obtain the refined saturated fatty acid methyl ester containing hydroxyl.
Example 5
200 g of epoxy castor oil methyl ester (the epoxy value is 5.0%) and 10 g of catalyst are sequentially added into a 500ml high-pressure reaction kettle with an electric stirring device, a measuring thermometer and a measuring device, the temperature is raised to 90 ℃ by stirring, high-purity hydrogen is introduced, the pressure is maintained at 4.0MPa, the temperature is continuously raised to 120 ℃, the reaction is stopped after 2.0 hours, and the catalyst is filtered to obtain the refined saturated castor oil methyl ester containing hydroxyl.
Example 6
200 g of epoxy cottonseed oil methyl ester and epoxy soybean oil 4 are sequentially added into a 500ml autoclave with an electric stirring device, a measuring thermometer and a high-pressure reaction kettle: 1 (epoxy value is 4.5 percent) and 15 g of catalyst are stirred and heated to 90 ℃, high-purity hydrogen is introduced, the pressure of 2.0MPa is maintained, the temperature is continuously raised to 150 ℃, the reaction is stopped after 2.5 hours, and the catalyst is filtered to obtain the refined saturated fatty acid methyl ester containing hydroxyl.
Example 7
200 g of epoxy hogwash oil methyl ester and epoxy methyl oleate 3 are sequentially added into a 500ml reaction kettle with an electric stirring device, a measuring thermometer and a high pressure reaction kettle: 2 (epoxy value is 6.5 percent) and 15 g of catalyst are stirred and heated to 90 ℃, high-purity hydrogen is introduced, the pressure of 4.0MPa is maintained, the temperature is continuously raised to 150 ℃, the reaction is stopped after 2.5 hours, and the catalyst is filtered, thus obtaining the refined saturated fatty acid methyl ester containing hydroxyl.
The saturated fatty acid methyl ester containing hydroxyl obtained by the hydrogenation modification process of the epoxy fatty acid methyl ester has special effect and can promote the reaction rate of synthesizing the surfactant. The following table illustrates:
remarking: sulfonation process: the method refers to a general sulfonation reaction process containing hydroxyl, which is different from a sulfonation process for synthesizing a-sulfo saturated fatty acid methyl ester salt, wherein the saturated fatty acid methyl ester needs a complex sulfonation process such as sulfonation-aging-reesterification-bleaching-neutralization and the like.
Ethoxylation process: the method refers to a general ethoxylation process containing hydroxyl, and is different from a fatty acid methyl ester insertion or mosaic type fatty acid methyl ester ethoxylation compound process, a special catalyst is needed, and only a general ethoxylation catalyst is needed, such as sodium hydroxide, potassium hydroxide, sodium methoxide and the like.
The saturated fatty acid methyl ester containing hydroxyl obtained by the epoxy fatty acid methyl ester hydrogenation modification process can obtain the surfactant with a structure different from the conventional structure by a relatively simple process for synthesizing the surfactant.
Claims (6)
1. The hydrogenation modification process of the epoxy fatty acid methyl ester is characterized in that the epoxy fatty acid methyl ester is subjected to hydrogenation process treatment to obtain saturated fatty acid methyl ester containing hydroxyl; wherein the reaction temperature of the hydrogenation process is 100-150 ℃, the reaction pressure is less than or equal to 4MPa, and the reaction time is 1-4 hours; the catalyst in the hydrogenation process comprises the effective component of metallic nickel, and the carrier component of the catalyst is alumina.
2. The process for hydrogenating and modifying epoxy fatty acid methyl ester according to claim 1, wherein the epoxy fatty acid methyl ester is a fatty acid methyl ester having at least one epoxy group having a three-membered ring.
3. The process for hydrogenation modification of epoxy fatty acid methyl ester according to claim 2, wherein the epoxy fatty acid methyl ester is any one of epoxy soybean oil methyl ester, epoxy palm oil methyl ester, epoxy cottonseed oil methyl ester, epoxy rapeseed oil methyl ester, epoxy oleic acid methyl ester, epoxy castor oil methyl ester and epoxy hogwash oil methyl ester, or a combination of at least two of them.
4. The hydrogenated modification process of epoxidized fatty acid methyl ester according to claim 1, wherein the epoxidized fatty acid methyl ester has an epoxy value of 3-8%.
5. The hydrogenation modification process of epoxidized fatty acid methyl ester according to claim 1, wherein the BET specific surface area of the catalyst used in the hydrogenation process is 100-200m2The pore volume is 0.4-0.5mL/g, the compaction density is 700-3The average grain diameter is 2.0-3.0 mm; the mass content of the metallic nickel in the catalyst is 15-25%; the average size of the alumina is 1.0-2.0 mm.
6. Saturated fatty acid methyl esters containing hydroxyl groups, characterized in that they are prepared by the process for the hydrogenation modification of epoxidized fatty acid methyl esters according to any one of claims 1 to 5.
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| CN201810629212.4A CN110615738A (en) | 2018-06-19 | 2018-06-19 | Epoxy fatty acid methyl ester hydrogenation modification process and hydroxyl-containing saturated fatty acid methyl ester |
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| CN201810629212.4A CN110615738A (en) | 2018-06-19 | 2018-06-19 | Epoxy fatty acid methyl ester hydrogenation modification process and hydroxyl-containing saturated fatty acid methyl ester |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112973697A (en) * | 2021-03-01 | 2021-06-18 | 广东工业大学 | Catalyst for hydrogenation reaction and synthesis method for catalyzing fatty acid methyl ester by using catalyst |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2617839A1 (en) * | 1987-07-06 | 1989-01-13 | Cetiom | Process for the catalytic manufacture of saturated fatty monohydroxy acids or of derivatives of the latter |
| DE4433958A1 (en) * | 1994-09-21 | 1996-03-28 | Henkel Kgaa | Hydroxy gp.-protected ring-opening prods. of epoxidised fats |
| US20090118535A1 (en) * | 2005-08-25 | 2009-05-07 | Takaaki Araki | Process for producing optically active ester |
| CN106467462A (en) * | 2016-09-20 | 2017-03-01 | 江南大学 | A kind of synthesis technique of branched chain fatty acid methyl ester |
-
2018
- 2018-06-19 CN CN201810629212.4A patent/CN110615738A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2617839A1 (en) * | 1987-07-06 | 1989-01-13 | Cetiom | Process for the catalytic manufacture of saturated fatty monohydroxy acids or of derivatives of the latter |
| DE4433958A1 (en) * | 1994-09-21 | 1996-03-28 | Henkel Kgaa | Hydroxy gp.-protected ring-opening prods. of epoxidised fats |
| US20090118535A1 (en) * | 2005-08-25 | 2009-05-07 | Takaaki Araki | Process for producing optically active ester |
| CN106467462A (en) * | 2016-09-20 | 2017-03-01 | 江南大学 | A kind of synthesis technique of branched chain fatty acid methyl ester |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112973697A (en) * | 2021-03-01 | 2021-06-18 | 广东工业大学 | Catalyst for hydrogenation reaction and synthesis method for catalyzing fatty acid methyl ester by using catalyst |
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