CN117924110A - Preparation method of erucamide - Google Patents
Preparation method of erucamide Download PDFInfo
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- CN117924110A CN117924110A CN202410090106.9A CN202410090106A CN117924110A CN 117924110 A CN117924110 A CN 117924110A CN 202410090106 A CN202410090106 A CN 202410090106A CN 117924110 A CN117924110 A CN 117924110A
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- Prior art keywords
- erucamide
- solid catalyst
- erucic acid
- zeolite powder
- producing
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- UAUDZVJPLUQNMU-KTKRTIGZSA-N erucamide Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-KTKRTIGZSA-N 0.000 title claims abstract description 63
- UAUDZVJPLUQNMU-UHFFFAOYSA-N Erucasaeureamid Natural products CCCCCCCCC=CCCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title abstract description 29
- 239000011949 solid catalyst Substances 0.000 claims abstract description 56
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims abstract description 23
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims abstract description 22
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 229910021536 Zeolite Inorganic materials 0.000 claims description 39
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 39
- 239000000843 powder Substances 0.000 claims description 39
- 239000010457 zeolite Substances 0.000 claims description 39
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 28
- 239000006185 dispersion Substances 0.000 claims description 25
- 238000003756 stirring Methods 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 17
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 14
- GICWIDZXWJGTCI-UHFFFAOYSA-I molybdenum pentachloride Chemical compound Cl[Mo](Cl)(Cl)(Cl)Cl GICWIDZXWJGTCI-UHFFFAOYSA-I 0.000 claims description 14
- ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 claims description 14
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 14
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000001132 ultrasonic dispersion Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 abstract description 8
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000007547 defect Effects 0.000 abstract description 2
- 239000012752 auxiliary agent Substances 0.000 description 17
- -1 octadecyl oleamide Chemical compound 0.000 description 16
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 15
- 229940073507 cocamidopropyl betaine Drugs 0.000 description 14
- 239000007791 liquid phase Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a preparation method of erucamide. The preparation method of the erucamide comprises the following steps: adding erucic acid and a solid catalyst into a reaction kettle, heating to 160-180 ℃, then introducing ammonia gas, reacting for 4-8 hours, cooling to 100-130 ℃, and filtering to remove the solid catalyst to obtain the erucic acid amide. The method takes erucic acid and ammonia gas as raw materials, and prepares erucic acid amide by adopting a solid catalyst prepared by a brand new method; the solid catalyst prepared by the brand new method can be added into a reaction kettle together with erucic acid before reaction, and the erucic acid amide can be prepared by reaction under normal pressure. The method avoids the defects that the catalyst is required to be added in the reaction process and the erucic acid amide is required to be prepared by the reaction under high pressure in the prior art, improves the convenience of production, and is beneficial to large-scale industrialized production.
Description
Technical Field
The invention relates to the technical field of compound preparation, in particular to a preparation method of erucamide.
Background
Erucic acid amide is an important derivative of erucic acid, and is an excellent fine chemical product with wide application range; it has a high melting point and good thermal stability, and thus is widely used as an anti-sticking agent and a slip agent for various plastics and resins.
Chinese patent 202111368330.2 discloses a liquid phase catalyst and a method for synthesizing erucamide by liquid phase catalysis, wherein the liquid phase catalyst consists of butyl silicate, polybutyl titanate and polyethylene glycol (PEG 200-800). The synthesis method comprises the following steps: A. heating butyl silicate, adding polybutyl titanate and polyethylene glycol, maintaining the temperature, stirring and mixing in a vacuum state, cooling to room temperature, filtering to obtain the finished product liquid phase catalyst, and sealing and preserving; B. the liquid phase catalyst is continuously and evenly added into a reactor (kettle) for carrying out amidation reaction between erucic acid and ammonia by adopting a metering pump, and the erucic acid amide is prepared. Compared with the existing solid catalyst, the method reduces the reaction temperature and the reaction pressure and shortens the reaction time.
Although, the method for synthesizing erucamide disclosed in Chinese patent 202111368330.2 has a plurality of advantages; however, the catalyst needs to be added after a period of reaction, and the catalyst needs to be continuously added by adopting a metering pump; there are inconveniences in practical industrial production, and further improvements are needed.
Disclosure of Invention
In order to overcome at least one technical problem existing in the prior art, the invention provides a preparation method of octadecyl oleamide.
The technical scheme of the invention is as follows:
A process for the preparation of erucamide comprising the steps of: adding erucic acid and a solid catalyst into a reaction kettle, heating to 160-180 ℃, then introducing ammonia gas, reacting for 4-8 hours, cooling to 100-130 ℃, and filtering to remove the solid catalyst to obtain the erucic acid amide.
The invention provides a brand-new preparation method, which takes erucic acid and ammonia gas as raw materials, and prepares erucic acid amide by adopting a solid catalyst prepared by the brand-new method; the solid catalyst prepared by the brand new method can be added into a reaction kettle together with erucic acid before reaction, and the erucic acid amide can be prepared by reaction under normal pressure.
Preferably, the weight ratio of erucic acid to solid catalyst is 100:1-3.
Further preferably, the weight ratio of erucic acid to solid catalyst is 100:1.5.
Preferably, the flow rate of the ammonia gas is 0.1 to 0.5L/min.
Preferably, the flow rate of the ammonia gas is 0.2 to 0.4L/min.
Preferably, the solid catalyst is prepared by the following method:
(1) Adding zeolite powder into water, and performing ultrasonic dispersion to obtain zeolite powder dispersion;
(2) Adding nickel chloride, neodymium trichloride and molybdenum pentachloride into the zeolite powder dispersion liquid, uniformly stirring, then adding sodium carbonate, stirring for 1-2 h, and separating solid after stirring;
(3) Roasting the solid at 1000-1200 deg.c for 2-3 hr to obtain the solid catalyst.
Preferably, the weight ratio of the zeolite powder to the water in the step (1) is 2-3 kg:10-20L.
Most preferably, the zeolite powder to water dosage ratio in step (1) is 2kg:15L.
Preferably, the dosage ratio of the zeolite powder dispersion liquid to nickel chloride, neodymium trichloride, molybdenum pentachloride and sodium carbonate in the step (2) is 10-20 L:50-70 g:100-130 g:130-150 g:300-400 g.
Most preferably, the zeolite powder dispersion in step (2) is used in an amount ratio of 15L:65g:125g:135g:350g to nickel chloride, neodymium trichloride, molybdenum pentachloride, and sodium carbonate.
Preferably, in step (2) an auxiliary agent is also added;
Wherein the dosage ratio of the zeolite powder dispersion liquid to the auxiliary agent is 10-20 L:100-200 g.
Most preferably, the zeolite powder dispersion and the adjuvant are used in a ratio of 10 to 20L:150g.
Preferably, the auxiliary agent is selected from octadecyl dihydroxyethyl amine oxide or cocamidopropyl betaine.
The inventors have surprisingly found that the addition of the aid octadecyl dihydroxyethyl amine oxide or cocoamidopropyl betaine to the solid catalyst during the solid catalyst preparation step can further increase the erucamide yield.
Further preferably, the auxiliary agent consists of octadecyl dihydroxyethyl amine oxide and cocamidopropyl betaine.
Preferably, the weight ratio of the octadecyl dihydroxyethyl amine oxide to the cocamidopropyl betaine is 1-3:1-3.
Most preferably, the weight ratio of octadecyl dihydroxyethyl amine oxide to cocamidopropyl betaine is 2:1.
The inventor finds that in the preparation step of the solid catalyst, the solid catalyst prepared by adding single octadecyl dihydroxyethyl amine oxide or single cocamidopropyl betaine can further improve the yield of erucamide, but the improvement is not large; the inventors have surprisingly found in further studies that: in the preparation step of the solid catalyst, adding an auxiliary agent consisting of octadecyl dihydroxyethyl amine oxide and cocamidopropyl betaine to prepare the solid catalyst, which can synergistically improve the yield of erucamide; the improvement degree of the yield of the erucamide is greatly higher than that of the solid catalyst prepared by only adding single octadecyl dihydroxyethyl amine oxide or single cocamidopropyl betaine.
Preferably, step (3) is carried out by calcining the solid at 1100 ℃ for 2.5 hours.
The beneficial effects are that: the invention provides a brand-new preparation method, which takes erucic acid and ammonia gas as raw materials, and prepares erucic acid amide by adopting a solid catalyst prepared by the brand-new method; the solid catalyst prepared by the brand new method can be added into a reaction kettle together with erucic acid before reaction, and the erucic acid amide can be prepared by reaction under normal pressure. The method avoids the defects that the catalyst is required to be added in the reaction process and the erucic acid amide is required to be prepared by the reaction under high pressure in the prior art, improves the convenience of production, and is beneficial to large-scale industrialized production.
Detailed Description
The present invention is further explained below with reference to specific examples, which are not intended to limit the present invention in any way.
Example 1
The embodiment provides a preparation method of erucamide, which comprises the following steps: adding erucic acid and a solid catalyst into a reaction kettle, heating to 175 ℃, then introducing ammonia gas at 0.3L/min, cooling to 12 ℃ after reacting for 6 hours, and filtering to remove the solid catalyst to obtain erucamide;
wherein the weight ratio of the erucic acid to the solid catalyst is 100:1.5;
the solid catalyst is prepared by the following steps:
(1) Adding zeolite powder into water, and performing ultrasonic dispersion to obtain zeolite powder dispersion; wherein the dosage ratio of the zeolite powder to the water is 2kg:15L;
(2) Adding nickel chloride, neodymium trichloride and molybdenum pentachloride into the zeolite powder dispersion liquid, uniformly stirring, then adding sodium carbonate, stirring for 1.5h, and separating solid after stirring; wherein the dosage ratio of the zeolite powder dispersion liquid to nickel chloride, neodymium trichloride, molybdenum pentachloride and sodium carbonate is 15L:65g:125g:135g:350g;
(3) And roasting the solid at 1100 ℃ for 2.5 hours, and obtaining the solid catalyst after roasting.
Example 2
The embodiment provides a preparation method of erucamide, which comprises the following steps: adding erucic acid and a solid catalyst into a reaction kettle, heating to 175 ℃, then introducing ammonia gas at 0.3L/min, cooling to 12 ℃ after reacting for 6 hours, and filtering to remove the solid catalyst to obtain erucamide;
wherein the weight ratio of the erucic acid to the solid catalyst is 100:1.5;
the solid catalyst is prepared by the following steps:
(1) Adding zeolite powder into water, and performing ultrasonic dispersion to obtain zeolite powder dispersion; wherein the dosage ratio of the zeolite powder to the water is 2kg:15L;
(2) Adding nickel chloride, neodymium trichloride, molybdenum pentachloride and an auxiliary agent into the zeolite powder dispersion liquid, uniformly stirring, then adding sodium carbonate, stirring for 1.5h, and separating solid after stirring is finished; wherein the dosage ratio of the zeolite powder dispersion liquid to nickel chloride, neodymium trichloride, molybdenum pentachloride and sodium carbonate is 15L:65g:125g:135g:350g; the dosage ratio of the zeolite powder dispersion liquid to the auxiliary agent is 15L:150g; the auxiliary agent is selected from octadecyl dihydroxyethyl amine oxide;
(3) And roasting the solid at 1100 ℃ for 2.5 hours, and obtaining the solid catalyst after roasting.
Example 3
The embodiment provides a preparation method of erucamide, which comprises the following steps: adding erucic acid and a solid catalyst into a reaction kettle, heating to 175 ℃, then introducing ammonia gas at 0.3L/min, cooling to 12 ℃ after reacting for 6 hours, and filtering to remove the solid catalyst to obtain erucamide;
wherein the weight ratio of the erucic acid to the solid catalyst is 100:1.5;
the solid catalyst is prepared by the following steps:
(1) Adding zeolite powder into water, and performing ultrasonic dispersion to obtain zeolite powder dispersion; wherein the dosage ratio of the zeolite powder to the water is 2kg:15L;
(2) Adding nickel chloride, neodymium trichloride, molybdenum pentachloride and an auxiliary agent into the zeolite powder dispersion liquid, uniformly stirring, then adding sodium carbonate, stirring for 1.5h, and separating solid after stirring is finished; wherein the dosage ratio of the zeolite powder dispersion liquid to nickel chloride, neodymium trichloride, molybdenum pentachloride and sodium carbonate is 15L:65g:125g:135g:350g; the dosage ratio of the zeolite powder dispersion liquid to the auxiliary agent is 15L:150g; the auxiliary agent is selected from cocamidopropyl betaine;
(3) And roasting the solid at 1100 ℃ for 2.5 hours, and obtaining the solid catalyst after roasting.
Example 4
The embodiment provides a preparation method of erucamide, which comprises the following steps: adding erucic acid and a solid catalyst into a reaction kettle, heating to 175 ℃, then introducing ammonia gas at 0.3L/min, cooling to 12 ℃ after reacting for 6 hours, and filtering to remove the solid catalyst to obtain erucamide;
wherein the weight ratio of the erucic acid to the solid catalyst is 100:1.5;
the solid catalyst is prepared by the following steps:
(1) Adding zeolite powder into water, and performing ultrasonic dispersion to obtain zeolite powder dispersion; wherein the dosage ratio of the zeolite powder to the water is 2kg:15L;
(2) Adding nickel chloride, neodymium trichloride, molybdenum pentachloride and an auxiliary agent into the zeolite powder dispersion liquid, uniformly stirring, then adding sodium carbonate, stirring for 1.5h, and separating solid after stirring is finished; wherein the dosage ratio of the zeolite powder dispersion liquid to nickel chloride, neodymium trichloride, molybdenum pentachloride and sodium carbonate is 15L:65g:125g:135g:350g; the dosage ratio of the zeolite powder dispersion liquid to the auxiliary agent is 15L:150g; the auxiliary agent consists of octadecyl dihydroxyethyl amine oxide and cocamidopropyl betaine in a weight ratio of 2:1;
(3) And roasting the solid at 1100 ℃ for 2.5 hours, and obtaining the solid catalyst after roasting.
TABLE 1 yield of erucamide prepared by the preparation method of the invention
| Yield of erucamide | |
| Preparation method of erucamide described in example 1 | 72.3％ |
| Preparation method of erucamide described in example 2 | 78.5％ |
| Preparation method of erucamide described in example 3 | 80.6％ |
| Preparation method of erucamide described in example 4 | 95.4％ |
As can be seen from the experimental data in Table 1, the erucamide can be prepared by the method for preparing erucamide described in example 1, but the yield is only 72.3%, which is still to be improved.
As can be seen from the experimental data in Table 1, the yield of erucamide prepared by the preparation methods of erucamide described in examples 2 and 3 is further improved compared with that of erucamide prepared by the preparation method of erucamide described in example 1; this illustrates: in the preparation step of the solid catalyst, the solid catalyst prepared by adding the auxiliary agent octadecyl dihydroxyethyl amine oxide or cocamidopropyl betaine can further improve the yield of erucamide.
As can be seen from the experimental data in Table 1, the yield of erucamide prepared by the preparation method of erucamide described in example 4 is greatly improved compared with that of example 1; the yield is also greatly higher than that of the preparation method of erucamide in the examples 2 and 3; this illustrates: in the preparation step of the solid catalyst, a single octadecyl dihydroxyethyl amine oxide or a single cocamidopropyl betaine is added to prepare the solid catalyst, and although the yield of erucamide can be further improved, the improvement is not large; only the solid catalyst prepared by adding the auxiliary agent consisting of octadecyl dihydroxyethyl amine oxide and cocamidopropyl betaine can further greatly improve the yield of erucamide. In the preparation step of the solid catalyst, adding an auxiliary agent consisting of octadecyl dihydroxyethyl amine oxide and cocamidopropyl betaine to prepare the solid catalyst, which can synergistically improve the yield of erucamide; the improvement degree of the yield of the erucamide is greatly higher than that of the solid catalyst prepared by only adding single octadecyl dihydroxyethyl amine oxide or single cocamidopropyl betaine.
Claims (10)
1. A method for preparing erucamide, which is characterized by comprising the following steps: adding erucic acid and a solid catalyst into a reaction kettle, heating to 160-180 ℃, then introducing ammonia gas, reacting for 4-8 hours, cooling to 100-130 ℃, and filtering to remove the solid catalyst to obtain the erucic acid amide.
2. The method for producing erucamide according to claim 1, wherein the weight ratio of erucic acid to solid catalyst is 100:1-3.
3. The method for producing erucamide according to claim 2, wherein the weight ratio of erucic acid to solid catalyst is 100:1.5.
4. The method for producing erucamide according to claim 1, wherein the flow rate of ammonia gas is 0.1 to 0.5L/min.
5. The method for producing erucamide according to claim 4, wherein the flow rate of the ammonia gas is 0.2 to 0.4L/min.
6. The method for preparing erucamide according to claim 1, wherein the solid catalyst is prepared by the following method:
(1) Adding zeolite powder into water, and performing ultrasonic dispersion to obtain zeolite powder dispersion;
(2) Adding nickel chloride, neodymium trichloride and molybdenum pentachloride into the zeolite powder dispersion liquid, uniformly stirring, then adding sodium carbonate, stirring for 1-2 h, and separating solid after stirring;
(3) Roasting the solid at 1000-1200 deg.c for 2-3 hr to obtain the solid catalyst.
7. The method for producing erucamide according to claim 1, wherein the weight ratio of zeolite powder to water in the step (1) is 2-3 kg:10-20L;
Most preferably, the zeolite powder to water dosage ratio in step (1) is 2kg:15L.
8. The method for producing erucamide according to claim 1, wherein the zeolite powder dispersion liquid in the step (2) is used in an amount ratio of 10 to 20l to 50 to 70g to 100 to 130g to 130 to 150g to 300 to 400g to nickel chloride, neodymium trichloride, molybdenum pentachloride and sodium carbonate.
9. The method for producing erucamide according to claim 1, wherein the zeolite powder dispersion liquid in the step (2) is used in an amount ratio of 15l:65g:125g:135g:350g to nickel chloride, neodymium trichloride, molybdenum pentachloride and sodium carbonate.
10. The method for producing erucamide according to claim 1, wherein the step (3) is to bake the solid at 1100 ℃ for 2.5 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN202410090106.9A CN117924110A (en) | 2024-01-23 | 2024-01-23 | Preparation method of erucamide |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202410090106.9A CN117924110A (en) | 2024-01-23 | 2024-01-23 | Preparation method of erucamide |
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| CN202410090106.9A Pending CN117924110A (en) | 2024-01-23 | 2024-01-23 | Preparation method of erucamide |
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