CN115594578B - Method for purifying erucic acid by adopting steam stripping mode - Google Patents
Method for purifying erucic acid by adopting steam stripping mode Download PDFInfo
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- CN115594578B CN115594578B CN202211253731.8A CN202211253731A CN115594578B CN 115594578 B CN115594578 B CN 115594578B CN 202211253731 A CN202211253731 A CN 202211253731A CN 115594578 B CN115594578 B CN 115594578B
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- erucic acid
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- steam
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- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 title claims abstract description 94
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 title claims abstract description 94
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 title claims abstract description 94
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000004821 distillation Methods 0.000 claims abstract description 32
- 238000001953 recrystallisation Methods 0.000 claims abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 111
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 230000004907 flux Effects 0.000 claims description 23
- 238000003756 stirring Methods 0.000 claims description 15
- 238000001816 cooling Methods 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 239000011259 mixed solution Substances 0.000 claims description 9
- 230000007547 defect Effects 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 238000005516 engineering process Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 22
- 238000010438 heat treatment Methods 0.000 description 14
- 239000002994 raw material Substances 0.000 description 11
- 230000001105 regulatory effect Effects 0.000 description 7
- 230000006837 decompression Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- UAUDZVJPLUQNMU-UHFFFAOYSA-N Erucasaeureamid Natural products CCCCCCCCC=CCCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UAUDZVJPLUQNMU-KTKRTIGZSA-N erucamide Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-KTKRTIGZSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000008041 oiling agent Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
- C07C51/445—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation by steam distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation technology of erucic acid, in particular to a method for purifying erucic acid by adopting a steam stripping mode. The method has the advantages of low reaction temperature, low distillation vacuum degree requirement and low recrystallization frequency, and solves the defects of high energy consumption, high equipment requirement and high solvent requirement for erucic acid purification.
Description
Technical Field
The invention relates to a preparation technology of erucic acid, in particular to a method for purifying erucic acid by adopting a steam stripping mode.
Background
Erucic acid, colorless needle crystals. Is very soluble in diethyl ether, ethanol and methanol, and insoluble in water. The method is mainly used for producing erucamide, and can also be used for preparing various surfactants, cosmetics, chemical fiber oiling agents and the like. The method comprises hydrolyzing vegetable oil or leftovers with conventional method (saponification acidolysis, acidification hydrolysis or pressure hydrolysis) to obtain vegetable oil fatty acid, and separating erucic acid from vegetable oil fatty acid. Freezing, squeezing, preliminary separating, and vacuum rectifying to obtain pure erucic acid. The method is characterized in that the erucic acid crude product is subjected to repeated recrystallization and then reduced pressure distillation to obtain the erucic acid product, and the method has the advantages of large solvent amount, low vacuum degree of about 100pa, high equipment requirement, high distillation temperature of 250 ℃, high energy consumption, and deep color of the product with overhigh distillation temperature; in addition, the purity of the product obtained by the method is 90-95%, and the product with higher purity is difficult to obtain.
Disclosure of Invention
The invention mainly aims at the defects of the existing erucic acid purification process, and discloses a novel erucic acid purification process which improves the quality content of erucic acid and reduces the cost.
It is an object of the present invention to address at least the above problems and/or disadvantages and to provide at least the advantages described below.
To achieve these objects and other advantages and in accordance with the purpose of the invention, there is provided a method for purifying erucic acid by steam stripping, distilling crude erucic acid by steam stripping, distilling with nitrogen steam stripping to obtain high erucic acid content, and recrystallizing with methanol to obtain erucic acid with content of more than 96wt%.
Preferably, the vacuum of the steam stripping distillation is 400-600 pa, the temperature is 200-230 ℃, the steam flux is 80-120 g/h, and the time is 0.5-2 hours.
Preferably, the vacuum of the steam stripping distillation is 450-500 pa, the temperature is 210-220 ℃, the steam flux is 90-110 g/h, and the time is 1-1.5 hours.
Preferably, the steam stripping distillation is performed under a vacuum of 450pa at a temperature of 215 ℃ and a steam flux of 100g/h for 1 hour.
Preferably, the vacuum of the nitrogen stripping distillation is 400-600 pa, the temperature is 220-250 ℃, the nitrogen flux is 2-4L/min, and the time is 1-5 hours.
Preferably, the vacuum of the nitrogen stripping distillation is 450-500 pa, the temperature is 225-240 ℃, the nitrogen flux is 2.5-3.5L/min, and the time is 1-5 hours.
Preferably, the vacuum of the nitrogen stripping distillation is 450pa, the temperature is 230 ℃, the nitrogen flux is 3L/min, and the time is 1-5 hours.
Preferably, the crude erucic acid has an erucic acid content of 60 to 80wt%; the methanol recrystallization process comprises the following steps: adding erucic acid obtained through nitrogen stripping distillation into methanol with the temperature of 15-25 ℃ to be stirred and completely dissolved, then cooling the mixed solution to the temperature of minus 15-minus 5 ℃ at constant speed, stirring for 1-3 h, filtering to obtain erucic acid, and drying under negative pressure to remove the methanol; the methanol adding amount in the methanol recrystallization is 1-4 times of the erucic acid mass.
Preferably, the methanol is added in an amount of 2 to 3 times the mass of erucic acid in the methanol recrystallization.
Preferably, the methanol is added in an amount of 2.5 times the mass of erucic acid in the methanol recrystallization.
The invention at least comprises the following beneficial effects: the method for purifying the erucic acid comprises the steps of removing low-boiling impurities from crude erucic acid through steam stripping distillation, obtaining high-purity erucic acid (about 95%) through nitrogen steam stripping distillation, and finally recrystallizing with methanol to obtain the erucic acid with the purity of more than 96wt%, thereby solving the defects of large consumption of recrystallization solvent, low distillation vacuum degree, high requirement on equipment, high distillation temperature, deep color of products and the like in the traditional method.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
The specific embodiment is as follows:
the present invention is described in further detail below with reference to examples to enable those skilled in the art to practice the same by referring to the description.
It will be understood that terms, such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
Example 1:
500g of erucic acid raw material with the content of 70wt%; adding erucic acid raw material into a steam stripping decompression device (decompression distillation device), regulating the vacuum to about 450Pa, heating to 200 ℃, introducing superheated steam (120 ℃) with the steam flux of 80g/h for 1h of stripping distillation, replacing the steam with nitrogen with the nitrogen flux of 2L/min, heating to 220 ℃, and receiving the fraction distilled at the moment; the distillation time is 4 hours, and the color of the product collected in the later stage is light yellow; 330g of erucic acid product with the content of 92.36 weight percent is obtained; adding the erucic acid into 330g of methanol with the temperature of 20 ℃ to be stirred and completely dissolved, cooling the mixed solution to the temperature of minus 10 ℃ at constant speed, stirring for 2 hours, filtering to obtain the erucic acid, drying under negative pressure, and removing the methanol to finally obtain 323.8g of erucic acid product with the content of 96.25wt% and the yield of 64.76wt%.
Example 2:
500g of erucic acid raw material with the content of 70wt%; adding erucic acid raw material into a steam stripping and decompressing device, regulating vacuum to about 450Pa, heating to 230 ℃, introducing superheated steam (120 ℃) with steam flux of 120g/h, stripping and distilling for 1h, replacing the steam with nitrogen flux of 4L/min, heating to 250 ℃, and receiving the distilled fraction; the distillation time is 1.5h, and the product color is light yellow; 268g of erucic acid product with a content of 91.53wt% is obtained; adding 1072g of erucic acid into 20 ℃ methanol, stirring to dissolve completely, cooling the mixed solution to-10 ℃ at constant speed, stirring for 2 hours, filtering to obtain erucic acid, drying under negative pressure, removing methanol, and finally obtaining 203g of erucic acid product with the content of 96.47wt% and the yield of 40.6wt%.
Example 3:
500g of erucic acid raw material with the content of 70wt%; adding erucic acid raw material into a steam stripping and decompressing device, regulating vacuum to about 450pa, heating to 215 ℃, introducing superheated steam (120 ℃) with steam flux of 100g/h, stripping and distilling for 1h, replacing the steam with nitrogen flux of 4L/min, heating to 230 ℃, and receiving the distilled fraction; the distillation time is 2.5h, 310g of erucic acid product is obtained, and the content is 93.74wt%; adding 775g of erucic acid into 20 ℃ methanol, stirring to dissolve completely, cooling the mixed solution to-10 ℃ at constant speed, stirring for 2 hours, filtering to obtain erucic acid, drying under negative pressure, removing methanol, and finally obtaining 297.4g of erucic acid product with the content of 97.41wt% and the yield of 59.48wt%.
Example 4:
500g of erucic acid raw material with the content of 70wt%; adding erucic acid raw material into a steam stripping and decompressing device, regulating vacuum to about 450Pa, heating to 230 ℃, introducing superheated steam (120 ℃) with steam flux of 100g/h, stripping and distilling for 1h, replacing the steam with nitrogen flux of 3L/min, heating to 230 ℃, and receiving the distilled fraction; the distillation time is 2.5h, 285g of erucic acid product is obtained, and the content is 96.33wt%; adding the erucic acid into 712.5g of methanol with the temperature of 20 ℃ to be fully dissolved by stirring, cooling the mixed solution to the temperature of minus 10 ℃ at constant speed, stirring for 2 hours, filtering to obtain 273.1g of erucic acid product, drying under negative pressure, removing the methanol, and finally obtaining the erucic acid product with the content of 98.25wt% and the yield of 54.62wt%.
Example 5
500g of erucic acid raw material with the content of 70wt%; adding erucic acid into a steam stripping and decompressing device, regulating the vacuum to about 450pa, heating to 215 ℃, introducing superheated steam (120 ℃), changing the steam into nitrogen with the steam flux of 100g/h and the steam stripping and distilling time of 1h, heating to 230 ℃ and receiving the distilled fraction; the distillation time is 2.5h, and 304g of erucic acid product with the content of 96.42wt% is obtained; adding 760g of erucic acid into 20 ℃ methanol, stirring to completely dissolve the erucic acid, cooling the mixed solution to-10 ℃ at constant speed, stirring for 2 hours, filtering to obtain 294.8g of erucic acid product, drying under negative pressure, and removing methanol, wherein the content is 98.83wt% and the yield is 58.96wt%.
Comparative example 1:
500g of erucic acid raw material with the content of 70wt%; adding erucic acid into a steam stripping decompression device, regulating the vacuum to about 450pa, heating to 215 ℃, introducing superheated steam (120 ℃), heating to 230 ℃ for 1h in steam flux of 100g/h, receiving the fraction distilled at the moment, and separating an organic phase in the fraction to obtain 321g of erucic acid product with the content of 91.48wt%; adding 760g of erucic acid into 20 ℃ methanol, stirring to completely dissolve the erucic acid, then uniformly cooling the mixed solution to-10 ℃ and stirring for 2 hours, filtering to obtain the erucic acid, drying under negative pressure to remove the methanol, and finally obtaining 312.1g of the erucic acid product with the content of 95.31wt% and the yield of 62.42wt%.
Comparative example 2:
500g of erucic acid raw material with the content of 70wt%; adding erucic acid into a nitrogen stripping decompression device, regulating the vacuum to about 450pa, heating to 215 ℃, introducing nitrogen with nitrogen flux of 3L/min, stripping for 1h, heating to 230 ℃, receiving the fraction at the time, and stripping for 2.5h to obtain 296.5g of erucic acid product with the content of 94.37wt%; adding 760g of erucic acid into 20 ℃ methanol, stirring to completely dissolve the erucic acid, then uniformly cooling the mixed solution to-10 ℃ and stirring for 2 hours, filtering to obtain the erucic acid, drying under negative pressure to remove the methanol, and finally obtaining 280.3g of the erucic acid product, wherein the content is 96.12wt% and the yield is 56.06wt%.
Table 1 shows the data of the stripping distillation and methanol recrystallization and the erucic acid purity and erucic acid yield of examples 1 to 5 and comparative examples 1 to 2.
TABLE 1
Although embodiments of the present invention have been disclosed above, it is not limited to the details and embodiments shown, it is well suited to various fields of use for which the invention is suited, and further modifications may be readily made by one skilled in the art, and the invention is therefore not to be limited to the particular details and examples shown and described herein, without departing from the general concepts defined by the claims and the equivalents thereof.
Claims (8)
1. A method for purifying erucic acid by adopting a stripping mode is characterized in that crude erucic acid is firstly subjected to steam stripping distillation, then is subjected to nitrogen stripping distillation to obtain high-content erucic acid, and finally is recrystallized by using methanol to obtain the erucic acid with the content of more than 96 wt%;
the vacuum of the steam stripping distillation is 400-600 pa, the temperature is 200-230 ℃, the steam flux is 80-120 g/h, and the time is 0.5-2 hours;
the vacuum of the nitrogen stripping distillation is 400-600 pa, the temperature is 220-250 ℃, the nitrogen flux is 2-4L/min, and the time is 1-5 hours.
2. The method for purifying erucic acid by steam stripping according to claim 1, wherein the steam stripping distillation is performed under vacuum of 450-500 pa, at a temperature of 210-220 ℃, and a steam flux of 90-110 g/h for 1-1.5 hours.
3. The method for purifying erucic acid by steam stripping according to claim 1, wherein the steam stripping distillation is performed under vacuum of 450pa at 215 ℃ with a steam flux of 100g/h for 1 hour.
4. The method for purifying erucic acid by adopting a stripping mode according to claim 1, wherein the vacuum of nitrogen stripping distillation is 450-500 pa, the temperature is 225-240 ℃, the nitrogen flux is 2.5-3.5L/min, and the time is 1-5 hours.
5. The method for purifying erucic acid by adopting a stripping mode according to claim 1, wherein the vacuum of nitrogen stripping distillation is 450pa, the temperature is 230 ℃, the nitrogen flux is 3L/min, and the time is 1-5 hours.
6. The method for purifying erucic acid by adopting a steam stripping mode according to claim 1, wherein the erucic acid content of the crude erucic acid is 60-80wt%; the methanol recrystallization process comprises the following steps: adding erucic acid obtained through nitrogen stripping distillation into methanol with the temperature of 15-25 ℃ to be stirred and completely dissolved, then cooling the mixed solution to the temperature of minus 15-5 ℃ at constant speed, stirring for 1-3 hours, filtering to obtain erucic acid, and drying under negative pressure to remove the methanol; the methanol adding amount in the methanol recrystallization is 1-4 times of the erucic acid mass.
7. The method for purifying erucic acid by adopting a stripping mode according to claim 1, wherein the methanol adding amount in the methanol recrystallization is 2-3 times of the erucic acid mass.
8. The method for purifying erucic acid by steam stripping according to claim 1, wherein the methanol is added in an amount which is 2.5 times the mass of erucic acid in the methanol recrystallization.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202211253731.8A CN115594578B (en) | 2022-10-13 | 2022-10-13 | Method for purifying erucic acid by adopting steam stripping mode |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4680092A (en) * | 1982-10-06 | 1987-07-14 | Hermann Stage | Process for degassing, dehydrating and precut separation in straight-run distillation of crude fatty acids |
| CN1649653A (en) * | 2002-03-18 | 2005-08-03 | Ip控股有限公司 | Methods for treating deodorizer distillate |
| CN102659560A (en) * | 2012-05-04 | 2012-09-12 | 上海晶纯实业有限公司 | Method for purifying erucic acid |
| CN103710146A (en) * | 2013-12-25 | 2014-04-09 | 南海油脂工业(赤湾)有限公司 | Removing method of free fatty acid in fully-hydrogenated high erucic acid rapeseed oil |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9365801B2 (en) * | 2013-02-04 | 2016-06-14 | Technochem International, Inc. | Process of converting low and high free fatty acid containing oils into no free fatty acid containing oils |
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- 2022-10-13 CN CN202211253731.8A patent/CN115594578B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4680092A (en) * | 1982-10-06 | 1987-07-14 | Hermann Stage | Process for degassing, dehydrating and precut separation in straight-run distillation of crude fatty acids |
| CN1649653A (en) * | 2002-03-18 | 2005-08-03 | Ip控股有限公司 | Methods for treating deodorizer distillate |
| CN102659560A (en) * | 2012-05-04 | 2012-09-12 | 上海晶纯实业有限公司 | Method for purifying erucic acid |
| CN103710146A (en) * | 2013-12-25 | 2014-04-09 | 南海油脂工业(赤湾)有限公司 | Removing method of free fatty acid in fully-hydrogenated high erucic acid rapeseed oil |
Non-Patent Citations (5)
| Title |
|---|
| 吴关庭 ; 郎春秀 ; 陈锦清 ; .芥酸的生产及其衍生产品开发.中国油脂.2007,(06),27-31. * |
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