CN100999465A - Synthesis method of fatty acid methyl ester - Google Patents
Synthesis method of fatty acid methyl ester Download PDFInfo
- Publication number
- CN100999465A CN100999465A CN 200610154874 CN200610154874A CN100999465A CN 100999465 A CN100999465 A CN 100999465A CN 200610154874 CN200610154874 CN 200610154874 CN 200610154874 A CN200610154874 A CN 200610154874A CN 100999465 A CN100999465 A CN 100999465A
- Authority
- CN
- China
- Prior art keywords
- fatty acid
- methyl ester
- acid methyl
- methanol
- synthetic method
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 235000019387 fatty acid methyl ester Nutrition 0.000 title claims abstract description 18
- 238000001308 synthesis method Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 60
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 13
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000010189 synthetic method Methods 0.000 claims abstract description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005639 Lauric acid Substances 0.000 claims abstract description 5
- 239000005642 Oleic acid Substances 0.000 claims abstract description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000002632 lipids Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 7
- 239000000194 fatty acid Substances 0.000 abstract description 7
- 229930195729 fatty acid Natural products 0.000 abstract description 7
- 150000004665 fatty acids Chemical class 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 6
- -1 ester compound Chemical class 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 238000010992 reflux Methods 0.000 abstract 2
- 238000005516 engineering process Methods 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012809 cooling fluid Substances 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 150000005451 methyl sulfates Chemical class 0.000 description 1
- 229950000081 metilsulfate Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A synthetic method of fatty acid methyl ester, belong to the synthetic technical field of ester compound in organic chemistry, regard fatty acid and methanol as raw materials, characterized by that to carry on the reflux reaction under the influence of catalyst and make fatty acid methyl ester, then distill the surplus methanol; the fatty acid is lauric acid or oleic acid; the catalyst is any one of p-toluenesulfonic acid, sodium methoxide, sodium hydroxide and the like, and the addition amount of the catalyst is 0.2-1.0 percent of the total weight percentage of fatty acid and methanol; the molar ratio of the fatty acid to the methanol can be 1: 5.0-10.0. The invention adopts fatty acid and methanol to directly carry out reflux reaction under the action of the catalyst, has reasonable process, simple operation, mild reaction condition and simple adopted equipment, thereby saving equipment investment and energy consumption and leading the product to have better service performance.
Description
Technical field
The present invention relates to a kind of synthetic method of fatty acid methyl ester, belong to technical field of synthesis of ester compounds in the organic chemistry.
Background technology
Fatty acid methyl ester is a raw material of producing kinds of surface promoting agents such as alkylol amide, metilsulfate, polyol ester type nonionogenic tenside, senior perfumed soap.The higher fatty acid methyl esters can directly be used as the additive of machining oil, cooling fluid, backing oil and boring wet goods finish in senior lubricant additive, the mechanical workout.Be used for the additive of Rubber processing and, under the prerequisite that does not influence efficient, can improve oil product, for petroleum products provides substitute directly as diesel-fuel or diesel-dope.Given this, the whole world increases day by day to the demand of this product.Existing methyl esterification of fatty acid is many to carry out in tower reactor and tank reactor, when carrying out methyl esterification of fatty acid, for fear of interference, usually lipid to be extracted from sample with organic solvent, make the lipid derivatize and generate fatty acid methyl ester under catalyst action, this method complexity and time are long, expense is high.
Summary of the invention
It is reasonable to the purpose of this invention is to provide a kind of technology, simple to operate, and product has the synthetic method of the fatty acid methyl ester of better use properties.
The present invention is the synthetic method of fatty acid methyl ester, is raw material with lipid acid and methyl alcohol, it is characterized in that carrying out back flow reaction obtain fatty acid methyl esters under the effect of catalyzer, distills out unnecessary methyl alcohol then.
Described lipid acid can be lauric acid or oleic acid etc.
Described catalyzer can be tosic acid, sodium methylate, and any of sodium hydroxide etc., its add-on is 0.2～1.0% of lipid acid and a methyl alcohol total weight percent.
The mol ratio of described lipid acid and methyl alcohol can be 1: 5.0～and 10.0.
The temperature of reaction of described back flow reaction can be 70～100 ℃, and the reaction times is 8～15 hours.
Described to distill out unnecessary methyl alcohol be under nitrogen gas stream, and distillation time is 40～100min.
The present invention adopts lipid acid and methyl alcohol directly to carry out back flow reaction under catalyst action, and technology is simple, the reaction conditions gentleness, and employing equipment is simple, thereby facility investment and energy consumption are more saved.
Embodiment
Embodiment 1:
In reactor, add 400 parts of lauric acid by weight, 384 parts of methyl alcohol stir 3.1 parts of sodium methylates of adding down, heat up gradually, back flow reaction is 12 hours under the reaction conditions of 90 ℃ of temperature, change still kettle then over to, under nitrogen gas stream, temperature is under 90 ℃ the condition, to carry out 1 hour distillation reaction, remove methyl alcohol, be cooled to 50 ℃ then, use in the alkali lye and a spot of lauric acid, product content 〉=99.5%.
Its back flow reaction equation is in the foregoing description:
CH
3OH+CH
3(CH
2)
10COOH→CH
3OOC(CH
2)
10CH
3+H
2O
Embodiment 2:
In reactor, add 400 parts of oleic acid by weight, 278 parts of methyl alcohol stir 2.7 parts of sodium methylates of adding down, heat up gradually, back flow reaction is 12 hours under the reaction conditions of 90 ℃ of temperature, change still kettle then over to, under nitrogen gas stream, temperature is under 90 ℃ the condition, carries out distillation in 1 hour, remove methyl alcohol, be cooled to 50 ℃ then, use in the alkali lye and a spot of oleic acid, product content 〉=99.5%
Its back flow reaction equation is in the foregoing description:
CH
3OH+4CH
3(CH
2)
7CH＝CH(CH
2)
7COOH—→
CH
3OOC(CH
2)
7CH＝CH(CH
2)
7CH
3+H
2O
Claims (6)
1, a kind of synthetic method of fatty acid methyl ester is a raw material with lipid acid and methyl alcohol, it is characterized in that carrying out back flow reaction obtain fatty acid methyl esters under the effect of catalyzer, distills out unnecessary methyl alcohol then.
2, by the synthetic method of the described fatty acid methyl ester of claim 1, it is characterized in that described lipid acid is lauric acid or oleic acid.
3, by the synthetic method of claim 1 or 2 described fatty acid methyl esters, it is characterized in that described catalyzer is a tosic acid, sodium methylate, any of sodium hydroxide, its add-on is 0.2～1.0% of lipid acid and a methyl alcohol total weight percent.
4, by the synthetic method of claim 1 or 2 described fatty acid methyl esters, the mol ratio that it is characterized in that described lipid acid and methyl alcohol is 1: 5.0～10.0.
5, by the synthetic method of the described fatty acid methyl ester of claim 1, the temperature of reaction that it is characterized in that described back flow reaction is 70～100 ℃, and the reaction times is 8～15 hours.
6, by the synthetic method of the described fatty acid methyl ester of claim 1, it is characterized in that described to distill out unnecessary methyl alcohol be under nitrogen gas stream, distillation time is 40～100min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610154874 CN100999465A (en) | 2006-11-28 | 2006-11-28 | Synthesis method of fatty acid methyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610154874 CN100999465A (en) | 2006-11-28 | 2006-11-28 | Synthesis method of fatty acid methyl ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN100999465A true CN100999465A (en) | 2007-07-18 |
Family
ID=38258300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200610154874 Pending CN100999465A (en) | 2006-11-28 | 2006-11-28 | Synthesis method of fatty acid methyl ester |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100999465A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102311838A (en) * | 2011-08-08 | 2012-01-11 | 华东理工大学 | Low-sulfur diesel oil lubrication additive and preparation method and application thereof |
| CN102703227A (en) * | 2012-06-11 | 2012-10-03 | 科凯精细化工（上海）有限公司 | Method for synthesizing fatty acid methyl ester |
| KR101782205B1 (en) | 2015-04-28 | 2017-09-28 | 이화여자대학교 산학협력단 | Process for preparing medium chain fatty acids from long chain fatty acids by bioconversion and chemical reaction |
| CN108658767A (en) * | 2018-07-12 | 2018-10-16 | 常州市金坛区维格生物科技有限公司 | A kind of preparation method of methyl oleate |
-
2006
- 2006-11-28 CN CN 200610154874 patent/CN100999465A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102311838A (en) * | 2011-08-08 | 2012-01-11 | 华东理工大学 | Low-sulfur diesel oil lubrication additive and preparation method and application thereof |
| CN102703227A (en) * | 2012-06-11 | 2012-10-03 | 科凯精细化工（上海）有限公司 | Method for synthesizing fatty acid methyl ester |
| KR101782205B1 (en) | 2015-04-28 | 2017-09-28 | 이화여자대학교 산학협력단 | Process for preparing medium chain fatty acids from long chain fatty acids by bioconversion and chemical reaction |
| CN108658767A (en) * | 2018-07-12 | 2018-10-16 | 常州市金坛区维格生物科技有限公司 | A kind of preparation method of methyl oleate |
| CN108658767B (en) * | 2018-07-12 | 2021-01-01 | 常州市金坛区维格生物科技有限公司 | Preparation method of methyl oleate |
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