CN117843583A - Preparation method of alkyl benzotriazole fatty amine salt and oil product additive - Google Patents
Preparation method of alkyl benzotriazole fatty amine salt and oil product additive Download PDFInfo
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- CN117843583A CN117843583A CN202311625497.1A CN202311625497A CN117843583A CN 117843583 A CN117843583 A CN 117843583A CN 202311625497 A CN202311625497 A CN 202311625497A CN 117843583 A CN117843583 A CN 117843583A
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- -1 alkyl benzotriazole Chemical compound 0.000 title claims abstract description 140
- 239000012964 benzotriazole Substances 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000000654 additive Substances 0.000 title claims abstract description 13
- 230000000996 additive effect Effects 0.000 title claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 56
- 229930040373 Paraformaldehyde Natural products 0.000 claims abstract description 31
- 229920002866 paraformaldehyde Polymers 0.000 claims abstract description 31
- 150000003335 secondary amines Chemical class 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 14
- 150000001412 amines Chemical class 0.000 claims abstract description 11
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 239000003921 oil Substances 0.000 claims description 34
- 238000004821 distillation Methods 0.000 claims description 26
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 claims description 11
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 claims description 11
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 10
- 125000002091 cationic group Chemical group 0.000 claims description 6
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 4
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003760 tallow Substances 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims 1
- 238000005260 corrosion Methods 0.000 abstract description 13
- 230000007797 corrosion Effects 0.000 abstract description 13
- 239000003960 organic solvent Substances 0.000 abstract description 9
- 230000003647 oxidation Effects 0.000 abstract description 9
- 238000007254 oxidation reaction Methods 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 4
- 238000003756 stirring Methods 0.000 description 30
- 230000000052 comparative effect Effects 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003831 antifriction material Substances 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
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Abstract
The invention relates to the technical field of synthesis, in particular to a preparation method of an alkyl benzotriazole fatty amine salt and an oil product additive. The invention relates to a preparation method of an alkylbenzene triazole fatty amine salt, which comprises the following steps: s1, performing a first reaction on paraformaldehyde, a primary amine cation collector and alkyl benzotriazole to obtain a first reaction solution; s2, carrying out a second reaction on the first reaction liquid, secondary amine and paraformaldehyde to obtain the alkylbenzene triazole fatty amine salt; wherein the primary amine cationic collector and the secondary amine have different numbers of carbon atoms. According to the preparation method of the fatty amine salt of the alkyl benzotriazole, the reaction is carried out step by adopting two different amines, and no organic solvent is added in the reaction process, so that the yield and purity of the product are improved. The alkyl benzotriazole fatty amine salt prepared by the method is added into an oil product, so that the oil product has more excellent oxidation resistance, corrosion resistance and oil-water separation property.
Description
Technical Field
The invention relates to the technical field of synthesis, in particular to a preparation method of an alkyl benzotriazole fatty amine salt and an oil product additive.
Background
The alkyl benzotriazole fatty amine salt has various functions of wear resistance, corrosion resistance, oxidation resistance, rust resistance, metal passivation and the like, can be used in gear oil, wear-resistant hydraulic oil, oil film bearing oil and lubricating grease, and can be used as a rust inhibitor and a vapor corrosion inhibitor in rust-proof grease; is added into natural mineral oil, fuel oil and lubricating oil to be used as antirust agent, antioxidant, metal passivating agent, antifriction agent, preservative and the like.
The existing preparation method of the fatty amine salt of the alkyl benzotriazole generally takes the alkyl benzotriazole, fatty amine and paraformaldehyde as raw materials, and reacts in an organic solvent to generate the fatty amine salt of the alkyl benzotriazole; but has the problems of complex operation, strict control of reaction conditions, low product purity and yield, poor low-temperature oil solubility of the prepared product, and the like.
In view of this, the present invention has been made.
Disclosure of Invention
The first object of the present invention is to provide a method for preparing an alkylbenzene triazole fatty amine salt, which improves the yield and purity of the product by using two different amines to react step by step without adding an organic solvent during the reaction.
The second object of the invention is to provide an oil additive which has more excellent stability, oil solubility, oxidation resistance, corrosion resistance and demulsification.
In order to achieve the above object of the present invention, the following technical solutions are adopted:
the invention provides a preparation method of an alkylbenzene triazole fatty amine salt, which comprises the following steps:
s1, performing a first reaction on paraformaldehyde, a primary amine cation collector and alkyl benzotriazole to obtain a first reaction solution;
s2, carrying out a second reaction on the first reaction liquid, secondary amine and paraformaldehyde to obtain the alkylbenzene triazole fatty amine salt;
wherein the primary amine cationic collector and the secondary amine have different numbers of carbon atoms.
Further, in step S1, the primary amine cationic collector comprises dodecylamine and/or octadecylamine.
Preferably, the primary amine cationic collector is dodecyl amine.
Further, in step S2, the secondary amine includes at least one of diisooctylamine, di-hydrogenated tallow secondary amine, and sec-butylamine.
Further, in step S1, the alkyl benzotriazole includes benzotriazole and/or methylbenzotriazole;
and/or the molar ratio of the polymethane, the amine-based cationic collector and the alkyl benzotriazole is (0.5 to 5): (0.5-5): (0.5-5).
Further, in the step S1, the temperature of the first reaction is 60-80 ℃;
and/or the time of the first reaction is 2-4 h.
Further, in step S1, after the first reaction, a first desolventizing treatment is further included.
Preferably, the first desolventizing treatment includes reduced pressure distillation.
Further, in step S2, the molar ratio of the secondary amine, the paraformaldehyde and the alkylbenzotriazole is (1 to 5): (1-5): (1-5).
Further, in the step S2, the temperature of the second reaction is 60-80 ℃;
and/or the time of the second reaction is 2-4 h.
Further, in step S2, after the second reaction, a second desolventizing treatment is further included;
preferably, the second desolventizing treatment includes reduced pressure distillation.
The invention also provides an oil product additive, which comprises the alkyl benzotriazole fatty amine salt prepared by the preparation method of the alkyl benzotriazole fatty amine salt.
Compared with the prior art, the invention has the beneficial effects that:
1. according to the preparation method of the fatty amine salt of the alkyl benzotriazole, the two different amines are adopted to react step by step, and no organic solvent is added in the reaction process, so that the reaction is fully carried out, the residue of the organic solvent in the product is avoided, and the yield and purity of the product are improved.
2. The alkyl benzotriazole fatty amine salt prepared by the invention is used as an oil product additive, has more excellent stability, oil solubility and demulsification, and can lead the oil product to have more excellent oxidation resistance, corrosion resistance and oil-water separation property when being added into the oil product.
Detailed Description
The technical solution of the present invention will be clearly and completely described in conjunction with the specific embodiments, but it will be understood by those skilled in the art that the examples described below are some, but not all, examples of the present invention, and are intended to be illustrative only and should not be construed as limiting the scope of the present invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
The preparation method of the alkyl benzotriazole fatty amine salt and the oil additive in the embodiment of the invention are specifically described below.
In some embodiments of the present invention, there is provided a method for preparing an alkylbenzene triazole fatty amine salt, comprising the steps of:
s1, performing a first reaction on paraformaldehyde, a primary amine cation collector and alkyl benzotriazole to obtain a first reaction solution;
s2, carrying out a second reaction on the first reaction liquid, the secondary amine and the paraformaldehyde to obtain an alkylbenzene triazole fatty amine salt;
wherein the primary amine cationic collector and the secondary amine have different numbers of carbon atoms.
According to the preparation method of the fatty amine salt of the alkyl benzotriazole, no organic solvent is added in the reaction process, the organic solvent is not needed to dissolve materials, no waste solvent or toxic waste gas is generated, the risk of environmental pollution is reduced, and the requirements of green chemical synthesis are met. The method directly mixes reactants and then carries out reaction, does not need to consume time and energy to heat and remove the organic solvent, greatly shortens the synthesis time, improves the synthesis efficiency, can avoid the residue of the organic solvent in the product, is beneficial to improving the purity of the product, and has purer product with the purity of more than or equal to 98 percent because the solution is not added and the prepared product has no problem of solvent residue.
In the preparation process of the invention, two different amines are used as reaction raw materials; the addition of primary amine cationic collector promotes anion absorption, so that the initial reaction is accelerated forward; the addition of secondary amine with different carbon atoms from primary amine cation collector makes the product structure appear amine with different structures, forms asymmetric structure, and the common use of two amines improves the stability of the product. The invention adopts a two-step method to add materials, and the reaction is carried out step by step, so that the raw materials react more fully, the improvement of the yield of the product is facilitated, and the yield can reach more than 90 percent.
In some embodiments of the invention, in step S1, the primary amine-based cationic collector comprises dodecylamine and/or octadecylamine; preferably, the primary amine cationic collector is dodecamine.
In some embodiments of the invention, in step S1, the secondary amine comprises at least one of diisooctylamine, di-hydrogenated tallow secondary amine, and sec-butylamine.
In some embodiments of the invention, in step S1, the alkylbenzotriazole comprises benzotriazole and/or methylbenzotriazole.
In some embodiments of the invention, in step S1, the molar ratio of the polymethane, the amine-based cationic collector, and the alkylbenzotriazole is (0.5 to 5): (0.5-5): (0.5-5); typical, but not limiting, molar ratios of paraformaldehyde and alkylbenzotriazole may be, for example, 0.5:0.5, 0.5: 1. 0.5: 3. 0.5: 5. 1:0.5, 1: 4. 2: 1. 2: 3. 2: 5. 3: 1. 3: 5. 4: 1. 4: 3. 4: 5. 5:0.5, 5: 2. 5:4 or any two of them; the molar ratio of amine cationic collector to alkyl benzotriazole may be 0.5:0.5, 0.5: 1. 0.5: 3. 0.5: 5. 1:0.5, 1: 4. 2: 1. 2: 3. 2: 5. 3: 1. 3: 5. 4: 1. 4: 3. 4: 5. 5:0.5, 5: 2. 5:4 or any two of them.
In some embodiments of the present invention, in step S1, the molar ratio of the polymethane, the amine-based cationic collector and the alkylbenzotriazole is (1 to 3): (1-3): (1-3).
In some embodiments of the invention, in step S1, the temperature of the first reaction is 60 to 80 ℃; typically, but not by way of limitation, the temperature of the first reaction may be, for example, 60 ℃, 65 ℃,70 ℃, 75 ℃, 80 ℃ or a range of values consisting of any two of these.
In some embodiments of the invention, in step S1, the time of the first reaction is 2 to 4 hours; typically, but not by way of limitation, the time of the first reaction is, for example, 2h, 2.5h, 3h, 3.5h, 4h, or a range of values consisting of any two of these.
In some embodiments of the invention, in step S1, after the first reaction, a first desolventizing treatment is further included; preferably, the first desolventizing treatment includes reduced pressure distillation; more preferably, the time of the first desolventizing treatment is 20 to 40 minutes.
Before the secondary amine is added, the water generated in the first step of reaction is removed, so that the reaction of the secondary amine added for the second time is promoted, and the reaction is fully carried out.
In some embodiments of the present invention, in step S1, after stirring paraformaldehyde and primary amine type cationic collector at 60 to 80 ℃ for 20 to 40min, alkylbenzotriazole is added, reacted at 60 to 80 ℃ for 2 to 4h, and then distilled at 60 to 80 ℃ under reduced pressure for 20 to 40min, to obtain a first reaction system.
In some embodiments of the invention, in step S2, the molar ratio of secondary amine, paraformaldehyde and alkylbenzotriazole is (1 to 5): (1-5): (1-5); typical, but not limiting, for example, the molar ratio of secondary amine to alkylbenzotriazole may be 1: 1. 1: 3. 1: 5. 2: 1. 2: 4. 2: 5. 3: 1. 3: 4. 3: 5. 4: 1. 4: 2. 4: 3. 4: 5. 5: 1. 5: 3. 5:4 or any two of them; the molar ratio of paraformaldehyde to alkyl benzotriazole may be 1: 1. 1: 3. 1: 5. 2: 1. 2: 4. 2: 5. 3: 1. 3: 4. 3: 5. 4: 1. 4: 2. 4: 3. 4: 5. 5: 1. 5: 3. 5:4 or any two of them.
In some embodiments of the invention, in step S2, the molar ratio of secondary amine, paraformaldehyde and alkylbenzotriazole is (1 to 3.5): (1-3.5): (1-3.5).
In some embodiments of the invention, in step S2, the temperature of the second reaction is 60 to 80 ℃; typically, but not by way of limitation, the temperature of the second reaction may be, for example, 60 ℃, 65 ℃,70 ℃, 75 ℃, 80 ℃ or a range of values consisting of any two of these.
In some embodiments of the invention, in step S2, the second reaction time is 2 to 4 hours; typically, but not by way of limitation, the time of the second reaction is, for example, 2h, 2.5h, 3h, 3.5h, 4h, or a range of values consisting of any two of these.
In some embodiments of the invention, in step S2, a second desolventizing treatment is further included after the second reaction; preferably, the second desolventizing treatment includes reduced pressure distillation; more preferably, the second desolventizing treatment is carried out for 20 to 40 minutes.
And after the reaction is finished, removing water generated by the reaction for the second time, and finally obtaining the fatty amine salt of the alkylbenzene triazole.
In some specific embodiments of the present invention, in step S2, the first reaction system, the secondary amine and the paraformaldehyde are reacted at 60 to 80 ℃ for 2 to 4 hours, and then distilled under reduced pressure at 60 to 80 ℃ for 20 to 40 minutes to obtain the alkylbenzene triazole fatty amine salt.
In some embodiments of the invention, there is also provided an oil additive comprising an alkyl benzotriazole fatty amine salt prepared by the process of preparing an alkyl benzotriazole fatty amine salt.
The alkyl benzotriazole fatty amine salt prepared by the invention is used as an oil product additive, and has more excellent stability, oil solubility, oxidation resistance, corrosion resistance and demulsification.
In some embodiments of the invention, an oil product is also provided comprising an alkyl benzotriazole fatty amine salt produced by the process for producing an alkyl benzotriazole fatty amine salt.
In some embodiments of the invention, the content of the fatty amine salt of alkylbenzene triazole in the oil is 0.02 to 0.15 weight percent.
The alkyl benzotriazole fatty amine salt can be added into oil products to ensure that the oil products have more excellent oxidation resistance, corrosion resistance and demulsification.
Example 1
The preparation method of the fatty amine salt of the alkyl benzotriazole provided by the embodiment comprises the following steps:
s1, adding 9g of paraformaldehyde and 55.59g of dodecyl amine into a 500mL round-bottom flask, starting a mechanical stirrer to stir, heating to 70 ℃ until particles are melted, stirring for 30min, adding 105.7g of methylbenzotriazole, continuing stirring for 3h at 70 ℃ after all solids are dissolved, and distilling at 70 ℃ under reduced pressure for 30min; after the reduced pressure distillation is finished, obtaining a first reaction solution;
s2, sequentially adding 9g of paraformaldehyde and 72.3g of diisooctylamine into the first reaction liquid, continuously stirring for 3 hours at 70 ℃ after all solids are dissolved, carrying out reduced pressure distillation for 30 minutes at 70 ℃, and filtering after the reduced pressure distillation is finished to obtain a product (alkylbenzene triazole fatty amine salt), wherein the yield of the product is 94.5%, and the purity of the product is more than 98%.
Example 2
The preparation method of the fatty amine salt of the alkyl benzotriazole provided by the embodiment comprises the following steps:
s1, adding 9g of paraformaldehyde and 55.59g of dodecyl amine into a 500mL round-bottom flask, starting a mechanical stirrer to stir, heating to 70 ℃ until particles are melted, stirring for 30min, adding 35.7g of methylbenzotriazole, continuing stirring for 3h at 70 ℃ after all solids are dissolved, and distilling at 70 ℃ under reduced pressure for 30min; after the reduced pressure distillation is finished, obtaining a first reaction solution;
s2, sequentially adding 9g of paraformaldehyde and 72.3g of diisooctylamine into the first reaction liquid, continuously stirring for 3 hours at 70 ℃ after all solids are dissolved, carrying out reduced pressure distillation for 30 minutes at 70 ℃, and filtering after the reduced pressure distillation is finished to obtain a product (alkylbenzene triazole fatty amine salt), wherein the yield of the product is 95.2%, and the purity of the product is more than 98%.
Example 3
The preparation method of the fatty amine salt of the alkyl benzotriazole provided by the embodiment comprises the following steps:
s1, adding 9g of paraformaldehyde and 55.59g of dodecyl amine into a 500mL round-bottom flask, starting a mechanical stirrer to stir, heating to 70 ℃ and stirring for 30min after particles are melted, adding 105.7g of methylbenzotriazole, and continuing stirring for 3h at 70 ℃ after all solids are dissolved to obtain a first reaction solution;
s2, sequentially adding 9g of paraformaldehyde and 72.3g of diisooctylamine into the first reaction liquid, continuously stirring for 3 hours at 70 ℃ after all solids are dissolved, carrying out reduced pressure distillation for 30 minutes at 70 ℃, and filtering after the reduced pressure distillation is finished to obtain a product (alkylbenzene triazole fatty amine salt), wherein the yield of the product is 94.2%, and the purity of the product is more than 97%.
Example 4
The preparation method of the fatty amine salt of the alkyl benzotriazole provided by the embodiment comprises the following steps:
s1, adding 9g of paraformaldehyde and 110.25g of octadecylamine into a 500mL round-bottomed flask, starting a mechanical stirrer to stir, heating to 70 ℃ until particles are melted, stirring for 30min, adding 105.7g of methylbenzotriazole, continuing stirring for 3h at 70 ℃ after all solids are dissolved, and distilling at 70 ℃ under reduced pressure for 30min; after the reduced pressure distillation is finished, obtaining a first reaction solution;
s2, sequentially adding 9g of paraformaldehyde and 72.3g of diisooctylamine into the first reaction liquid, continuously stirring for 3 hours at 70 ℃ after all solids are dissolved, carrying out reduced pressure distillation for 30 minutes at 70 ℃, and filtering after the reduced pressure distillation is finished to obtain a product (alkylbenzene triazole fatty amine salt), wherein the yield of the product is 94.8%, and the purity of the product is more than 98%.
Example 5
The process for preparing an alkylbenzotriazole fatty amine salt provided in this example is referred to in example 1, except that 72.3g of diisooctylamine is replaced with 50g of a bis-hydrogenated tallow secondary amine.
Example 6
The process for preparing an alkylbenzotriazole fatty amine salt provided in this example is described with reference to example 1, except that 72.3g of diisooctylamine is replaced with 35g of sec-butylamine.
Comparative example 1
The preparation method of the fatty amine salt of the alkyl benzotriazole provided by the comparative example comprises the following steps:
9g of paraformaldehyde and 55.59g of dodecyl amine are added into a 500mL round-bottom flask, a mechanical stirrer is started for stirring, the temperature is raised to 70 ℃ and after particles are melted, stirring is carried out for 30min, 105.7g of methylbenzotriazole is added, after all solids are dissolved, stirring is continued for 3h at 70 ℃, and reduced pressure distillation is carried out for 30min at 70 ℃; and after the reduced pressure distillation is finished, filtering to obtain a product (alkyl benzotriazole fatty amine salt).
Comparative example 2
The preparation method of the fatty amine salt of the alkyl benzotriazole provided by the comparative example comprises the following steps:
9g of paraformaldehyde and 72.3g of diisooctylamine are added into a 500mL round-bottomed flask, a mechanical stirrer is started for stirring, the temperature is raised to 70 ℃ until particles are melted, stirring is carried out for 30min, 105.7g of methylbenzotriazole is added, after all solids are dissolved, stirring is continued for 3h at 70 ℃, and reduced pressure distillation is carried out for 30min at 70 ℃; and after the reduced pressure distillation is finished, filtering to obtain a product (alkyl benzotriazole fatty amine salt).
Comparative example 3
The preparation method of the fatty amine salt of the alkyl benzotriazole provided by the comparative example comprises the following steps:
9g of paraformaldehyde and 110.25g of octadecylamine are added into a 500mL round-bottom flask, a mechanical stirrer is started for stirring, the temperature is raised to 70 ℃ and after particles are melted, stirring is carried out for 30min, 106.8g of methylbenzotriazole is added, after all solids are dissolved, stirring is continued for 3h at 70 ℃, and reduced pressure distillation is carried out for 30min at 70 ℃; and after the reduced pressure distillation is finished, filtering to obtain a product (alkyl benzotriazole fatty amine salt).
Comparative example 4
The preparation method of the fatty amine salt of the alkyl benzotriazole provided by the comparative example comprises the following steps:
s1, adding 9g of paraformaldehyde and 72.3g of diisooctylamine into a 500mL round-bottomed flask, starting a mechanical stirrer to stir, heating to 70 ℃ until particles are melted, stirring for 30min, adding 105.7g of methylbenzotriazole, after all solids are dissolved, continuing stirring for 3h at 70 ℃, and distilling at 70 ℃ under reduced pressure for 30min; after the reduced pressure distillation is finished, obtaining a first reaction solution;
s2, sequentially adding 9g of paraformaldehyde and 55.59g of dodecyl amine into the first reaction liquid, continuously stirring for 3 hours at 70 ℃ after all solids are dissolved, and carrying out reduced pressure distillation at 70 ℃ for 30 minutes, wherein after the reduced pressure distillation is finished, filtering to obtain the product (alkylbenzene triazole fatty amine salt).
Test example 1
The stability of the products obtained in examples 1 to 4 and comparative examples 1 to 4 was measured, and the results are shown in Table 1.
The testing method comprises the following steps: the obtained products were stored at normal temperature, and observed at one week, three weeks, six weeks and twelve weeks in this order, and the change in the final state of the products before and after storage was observed. Table 1 shows the comparison of the states observed at the twelfth week of the product.
TABLE 1
| Product status before storage | Post storage product status | |
| Example 1 | Yellow transparent liquid | Yellow transparent liquid |
| Example 2 | Yellow transparent liquid | Pale yellow transparent liquid |
| Example 3 | Yellow transparent liquid | Yellow crystals |
| Example 4 | Yellow transparent liquid | A small amount of yellow crystals appeared |
| Comparative example 1 | Yellow transparent liquid | Yellow crystals |
| Comparative example 2 | Yellow transparent liquid | Yellow crystals |
| Comparative example 3 | Yellow transparent liquid | Yellow crystals |
| Comparative example 4 | Yellow transparent liquid | A small amount of yellow crystals appeared |
As can be seen from Table 1, the alkyl benzotriazole fatty amine salt prepared by the invention has more excellent stability.
Test example 2
The performance of the oils was tested using example 1, example 2 and the competing products (benzotriazole fatty amine salts, T406E) as oil additives, respectively, and the results are shown in tables 3 and 4.
The components of the oil products (1 # to 3# and the mass percent (wt%) of each component are shown in Table 2.
TABLE 2
| Numbering device | Oil additive | Sulfurized isobutylene | Base oil |
| 1# | 0.1wt％ | 3wt％ | 96.9wt％ |
| 2# | 0.05wt％ | 3wt％ | 96.95wt％ |
| 3# | 0.02wt％ | 3wt％ | 96.98wt％ |
Copper corrosion test method: copper corrosion is determined by referring to GB/T5096 experimental standard, the polished copper sheet is placed in an oil product, the temperature is kept constant for 3 hours at 121 ℃, and the corrosion resistance of the oil product is evaluated according to the color rating of the copper sheet.
Test method of antioxidant: the measurement of the rotary oxygen bomb was performed with reference to the experimental standard of SH/T0193-92, and the oxidation resistance of the oil product was evaluated according to the time rating of the rotary oxygen bomb.
The oil product adopted in the copper corrosion test and the oxidation resistance test is oil product 3#.
TABLE 3 Table 3
| Corrosion resistance (rating level) | Antioxidant (time to spin oxygen bomb) | |
| Example 1 | 1b | 120min |
| Example 2 | 3b | 104min |
| Bidding article | 2a | 116min |
The method for testing the separability of oil products and water comprises the following steps: the demulsifying was measured according to the experimental standard of GB/T7305-2003, and the separation of oil from water was evaluated according to the demulsifying time of different dosages, and the results are shown in Table 4.
The values in brackets in Table 4, e.g., 43-37, represent the volume numbers of oil and water separated, and are the readings of the results of experiments conducted according to the GB/T7305-2003 standard.
TABLE 4 Table 4
It can be seen from tables 3 and 4 that the oil products added with the fatty amine salt of alkylbenzene triazole of the present invention have more excellent oxidation resistance, corrosion resistance and oil-water separation properties.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and not for limiting the same; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some or all of the technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit of the corresponding technical solutions.
Claims (10)
1. The preparation method of the fatty amine salt of the alkylbenzene triazole is characterized by comprising the following steps:
s1, performing a first reaction on paraformaldehyde, a primary amine cation collector and alkyl benzotriazole to obtain a first reaction solution;
s2, carrying out a second reaction on the first reaction liquid, secondary amine and paraformaldehyde to obtain the alkylbenzene triazole fatty amine salt;
wherein the primary amine cationic collector and the secondary amine have different numbers of carbon atoms.
2. The method for producing an alkylbenzene triazole fatty amine salt according to claim 1, wherein in step S1, said primary amine-based cation collector comprises dodecylamine and/or octadecylamine;
preferably, the primary amine cationic collector is dodecyl amine.
3. The method for producing an alkylbenzene triazole fatty amine salt according to claim 1, wherein in step S2, said secondary amine comprises at least one of diisooctylamine, dihydrided tallow secondary amine and sec-butylamine.
4. The method for preparing an alkylbenzotriazole fatty amine salt according to claim 1, wherein in step S1, the alkylbenzotriazole comprises benzotriazole and/or methylbenzotriazole;
and/or the molar ratio of the paraformaldehyde, the amine-based cationic collector and the alkyl benzotriazole is (0.5 to 5): (0.5-5): (0.5-5).
5. The method for preparing an alkylbenzene triazole fatty amine salt according to claim 1 wherein in step S1, the temperature of said first reaction is 60 to 80 ℃;
and/or the time of the first reaction is 2-4 h.
6. The method for preparing an alkylbenzene triazole fatty amine salt according to claim 1, wherein in step S1, after said first reaction, a first desolventizing treatment is further included;
preferably, the first desolventizing treatment includes reduced pressure distillation.
7. The method for producing an alkylbenzene triazole fatty amine salt according to claim 1 wherein in step S2, the molar ratio of said secondary amine, said paraformaldehyde and said alkylbenzene triazole is (1 to 5): (1-5): (1-5).
8. The method for preparing an alkylbenzene triazole fatty amine salt according to claim 1 wherein in step S2, the temperature of said second reaction is 60 to 80 ℃;
and/or the time of the second reaction is 2-4 h.
9. The method for preparing an alkylbenzene triazole fatty amine salt according to claim 1, wherein in step S2, said second reaction is followed by a second desolventizing treatment;
preferably, the second desolventizing treatment includes reduced pressure distillation.
10. An oil additive comprising an alkylbenzene triazole fatty amine salt produced by the process for producing an alkylbenzene triazole fatty amine salt according to any one of claims 1 to 9.
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