CN111039899A - Novel plant-based lubricating oil additive and preparation method thereof - Google Patents

Novel plant-based lubricating oil additive and preparation method thereof Download PDF

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CN111039899A
CN111039899A CN201911320189.1A CN201911320189A CN111039899A CN 111039899 A CN111039899 A CN 111039899A CN 201911320189 A CN201911320189 A CN 201911320189A CN 111039899 A CN111039899 A CN 111039899A
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lubricating oil
plant
oil
based lubricating
novel plant
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杨初
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/401—Fatty vegetable or animal oils used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/402—Castor oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)

Abstract

The invention belongs to the technical field of lubricating oil. The invention relates to a novel plant-based lubricant additive and a preparation method thereof, the method takes N, S five-membered heterocycle (A), 1, 4-bis (potassium dithioformate) piperazine (B) and chlorohydrocarbon (D) as raw materials, and the novel plant-based lubricant additive is obtained through multi-step substitution reaction, so that the defects of single function, high-temperature oxidation resistance and poor wear resistance of the conventional plant-based lubricant additive are effectively overcome, the biodegradability is excellent, and the synthetic raw materials are wide and environment-friendly. It is anticipated that the product will have a wide market space.

Description

Novel plant-based lubricating oil additive and preparation method thereof
Technical Field
The invention relates to a novel plant-based lubricating oil additive and a preparation method thereof. The invention belongs to the technical field of lubricating oil.
Background
With the development of science and technology, mechanical equipment is developed towards high load, and in order to meet the development requirements of mechanical equipment, higher requirements are also put on used lubricating oil, and the lubricating oil has higher load-carrying property, high-temperature oxidation resistance and the like. Because of the rigorous requirements of modern processing and production, the abrasion of the staggered parts of the parts is intensified, and the lubricating oil added to the parts is gradually unable to keep pace with the development in performance. Therefore, the research can be carried out in the direction of the lubricating oil additive, and the functions of extreme pressure abrasion resistance, oxidation resistance, rust prevention capability, biodegradability and the like of the additive are improved. The traditional multifunctional lubricating oil additive dialkyl dithiophosphate (ZDDP) has a narrow application range because zinc element and phosphorus element are difficult to meet the ash limit requirement of modern equipment.
The vegetable oil has excellent environmental friendliness, such as self-biodegradability, low ecological toxicity, renewable resource origin, and no generation of volatile organic chemical substances, so that the vegetable oil can play roles of emulsification, plasticization, lubrication, friction reduction and the like, can be used for the visual line of researchers, and can be applied to corresponding fields. Among them, a large amount of scientific research work has been put into vegetable oil-based lubricating oils. Although some lubricating oil markets are mainly developed by using vegetable oil, there is still clear room for further research make internal disorder or usurp in the field of vegetable oil. The vegetable oil with obvious characteristic advantages is not yet a widely used oil of the base oil of the lubricating oil, mainly because most vegetable oils have poor oxidation stability, insufficient high temperature resistance and the like.
In view of the increasingly prominent environmental problems, the requirement for biodegradability of lubricating oils is urgent, and the related technical level of additives is developing in the direction of meeting the requirements of higher quality engine oils and improving global standards, and the biodegradability is also continuously improving. Under the condition of rapid technological development and the premise of non-renewable mineral oil resources, it is important to develop a lubricant additive capable of solving the problems of high-temperature oxidation resistance, wear resistance, biodegradability and the like of the traditional plant-based lubricant additive.
Disclosure of Invention
The invention aims to overcome the defects of poor wear resistance and poor high-temperature oxidation resistance of a plant-based lubricating oil additive in the prior art, and provides a novel plant-based lubricating oil additive and a preparation method thereof. It is anticipated that the product will have a wide market space.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a novel plant-based lubricating oil additive has a structural formula as follows:
Figure BDA0002326930080000021
wherein R is1：C8H17、C9H19Or C10H21。
A preparation method of a novel plant-based lubricating oil additive is characterized by comprising the following steps: comprises the following steps:
(1) substitution reaction to obtain piperazine derivative, which is marked as C;
(2) and (4) carrying out substitution reaction to obtain a novel plant-based lubricating oil additive, which is marked as E.
Preferably, the step (1) is specifically:
dissolving 1mol of five-membered heterocyclic structure (A) and 0.5-0.6mol of 1, 4-bis (potassium dithioformate) piperazine (B) in 30mol of organic solvent containing 0.5-5 wt% of potassium phosphate, stirring for 1-3h at 5 ℃, continuing to react for 1-2h at normal temperature, standing for 12h, performing suction filtration, and washing with water until the solution is clear; and adding the filter cake into the mixed solvent I, soaking, decoloring, washing, performing suction filtration, and drying at 50-60 ℃ to obtain a substance containing the siloxane modified five-membered heterocyclic structure, which is marked as C.
Preferably, the step (2) is specifically:
dissolving 1mol of C and 2-2.2mol of chlorohydrocarbon (D) in 60mol of saturated organic solvent containing potassium iodide and anhydrous potassium carbonate, mechanically stirring for 40min, and heating and refluxing in water bath for 3-8 h; cooling to room temperature, filtering, taking the filtrate, washing with a mixed solvent II, recrystallizing, filtering, and drying to obtain the novel plant-based lubricating oil additive, which is marked as E.
Preferably, the organic solvent is N, N-dimethylformamide, tetrahydrofuran, dioxane or acetone.
Preferably, the mixed solvent I is absolute ethyl alcohol/ethyl acetate/acetone according to a volume ratio of 1-2:1-2: 2-3.
Preferably, the mixed solvent II is water/absolute ethyl alcohol/N, N-dimethylformamide according to the volume ratio of 1:2: 2-3.
A plant-based lubricating oil composition is prepared from the following raw materials in parts by weight: 97-99.8 parts of vegetable oil base oil and 0.2-3 parts of novel additive.
Preferably, the vegetable oil base oil is one or more of cottonseed oil, soybean oil, peanut oil, palm oil, castor oil and sunflower seed oil.
Preferably, the preparation method of the plant-based lubricating oil composition comprises the following steps: mixing the above components at 60-90 deg.C and vacuum degree lower than-0.09 MPa and at 50rps rotation speed for 1h to obtain vegetable lubricating oil product.
The novel plant-based lubricating oil additive provided by the invention has the following preparation process:
Figure BDA0002326930080000031
the invention has the beneficial effects that:
(1) the invention provides a novel plant-based lubricating oil additive, which is prepared by adopting N, S five-membered heterocycle (A), 1, 4-bis (potassium dithioformate) piperazine (B) and chlorohydrocarbon (D) as raw materials, and overcomes the defects of high-temperature oxidation resistance and poor wear resistance of the traditional plant-based lubricating oil additive.
(2) The invention provides a preparation method of a novel plant-based lubricating oil additive, wherein a five-membered heterocycle is used as one of raw materials. Firstly, the existence of the five-membered heterocyclic ring N, S element can form a complex to be adsorbed on the surface of metal to form a molecular protective layer, so that the wear resistance is excellent, and the lubricating effect can be effectively improved; secondly, the N, S five-membered heterocycle is green, environment-friendly and biodegradable, and the existence of N enables the structure to have certain oxygen resistance; finally, the five-membered heterocyclic structure has high temperature resistance.
(3) The invention provides a preparation method of a novel plant-based lubricating oil additive, which adopts 1, 4-bis (potassium dithioformate) piperazine as one of raw materials. On one hand, the existence of the six-membered ring molecular structure of the piperazine ring improves the high temperature resistance of the lubricating oil; on the other hand, N element in piperazine ring can be adsorbed and form a molecular protective layer, and further excellent wear resistance is provided.
(4) The invention provides a preparation method of a novel plant-based lubricating oil additive, which adopts chlorohydrocarbon as one of raw materials. The long chain structure of C8-C10 forms a molecular film by forming chain entanglement with the surrounding molecular structure, and has excellent anti-wear effect.
(5) The invention provides a novel plant-based lubricating oil additive, which solves the problems of single function, poor oxidation resistance and high temperature resistance, excellent biodegradability, wide synthetic raw materials and environmental protection of the conventional plant-based lubricating oil additive. The product has wide market prospect.
The specific implementation mode is as follows:
the present invention will be described in detail with reference to examples. It is to be understood, however, that the following examples are illustrative of embodiments of the present invention and are not to be construed as limiting the scope of the invention.
Example 1
Dissolving 1mol of five-membered heterocyclic structure (A) and 0.5mol of 1, 4-bis (potassium dithioformate) piperazine (B) in 30mol of N, N-dimethylformamide containing 0.5 wt% of potassium phosphate, stirring for 3h at 5 ℃, continuing to react for 1h at normal temperature, standing for 12h, performing suction filtration, and washing with water until the mixture is clear; adding absolute ethyl alcohol/ethyl acetate/acetone into the filter cake, soaking the filter cake in a mixed solvent I with the volume ratio of 1:1:2, decoloring, washing, performing suction filtration, and drying at 60 ℃ to obtain the siloxane modified five-membered heterocyclic structure (IR: 3432 cm)-1、2403cm-1: -SH is present; 1100cm-1: a five-membered heterocycle exists; 1074cm-1: -N-is present; 1670cm-1: piperazine ring-C-N-present), as C.
Dissolving 1mol of C and 2.2mol of chlorooctane (D) in 60mol of saturated N, N-dimethylformamide containing potassium iodide and anhydrous potassium carbonate, mechanically stirring for 40min, and heating and refluxing in a water bath for 8 h; cooling to room temperature, filtering, washing the filtrate with a mixed solvent II of water/absolute ethyl alcohol/N, N-dimethylformamide in a volume ratio of 1:2:2, recrystallizing, and performing suction filtration and drying to obtain the novel compoundVegetable-based lubricating oil additive (IR: 3432 cm)-1、2403cm-1: -SH disappearance; 1100cm-1: a five-membered heterocycle exists; 1074cm-1: -N-is present; 1670cm-1: piperazine ring-C-N-present), as E.
Examples 2-6, otherwise identical to example 1, differ as set forth in the following table:
Figure BDA0002326930080000041
Figure BDA0002326930080000051
the novel plant-based lubricating oil additive obtained in specific example 1 was used as a base material in application examples to prepare a plant-based lubricating oil composition.
Application example 1
A plant-based lubricating oil composition is prepared from the following raw materials in parts by weight: 98 parts of sunflower seed oil base oil and 2 parts of a novel additive.
Stirring the above components at 90 deg.C and vacuum degree less than-0.09 MPa at 50rps for 1hr, and mixing to obtain vegetable lubricating oil product.
Application examples 2 to 6 were conducted in the same manner as in application example 1 except that the following Table was used
Figure BDA0002326930080000052
Practical example comparative example 1
A plant-based lubricating oil composition is prepared from the following raw materials in parts by weight: 100 parts of sunflower seed oil base oil.
Practical example comparative example 2
A plant-based lubricating oil composition is prepared from the following raw materials in parts by weight: 98 parts of sunflower seed oil base oil and 2 parts of antioxidant alkylphenol.
Stirring the above components at 90 deg.C and vacuum degree less than-0.09 MPa at 50rps for 1hr, and mixing to obtain vegetable lubricating oil product.
Practical example comparative example 3
A plant-based lubricating oil composition is prepared from the following raw materials in parts by weight: 98 parts of sunflower seed oil base oil and 2 parts of antiwear agent phosphite ester.
Stirring the above components at 90 deg.C and vacuum degree less than-0.09 MPa at 50rps for 1hr, and mixing to obtain vegetable lubricating oil product.
The physical properties, including oxidation resistance, decomposition temperature, wear resistance, and biodegradation results, of the plant-based lubricant additives prepared in examples 1 to 6 of the present invention and comparative examples 1 to 3 were measured, respectively, as shown in table 1.
Table 1 physical test properties of the examples
Figure BDA0002326930080000061
As can be seen from table 1, the vegetable-based lubricating oil prepared by using the novel vegetable-based lubricating oil additive of the present invention has significant advantages including solubility, heat resistance, wear resistance, biodegradability, etc. in addition to antioxidant stability, compared with conventional vegetable-oil-based lubricating oils.
Secondly, the results in table 1 show that the novel plant-based lubricating oil additive of the invention has the effects of an antioxidant and an anti-wear agent, and the product structure of the invention contains antioxidant and high temperature resistant functional structures such as a five-membered heterocyclic structure and a piperazine structure, so that the novel plant-based lubricating oil additive has excellent performance, the biodegradation index BDI is more than 80%, and the novel plant-based lubricating oil additive is completely suitable for the standard of the plant-based lubricating oil additive.
In summary, the novel plant-based lubricating oil additive provided by the invention can solve the problems of single function and insufficient high-temperature oxidation resistance of the traditional plant-based lubricating oil additive, has excellent wear resistance and biodegradability, meets the use standard of plant-based lubricating oil, and has a wide market prospect.
The test method comprises the following steps:
1) antioxidant stability: the oxidation stability of coal conversion base oil was studied by reference to the article "shoghui, old need. PDSC method [ J ]. lubrication and sealing, 2008,33(4):89-91 ]. The longer the induced oxidation time, the better the oxidation resistance.
2) Solubility: the synthetic additive was added to 100g of vegetable oil in small to large proportions, heated, left to stand, cooled and the dissolution observed until the additive appeared cloudy in the rapeseed oil, at which point the maximum solubility of the test product in the rapeseed oil was obtained.
3) Decomposition temperature (thermogravimetric analysis): and (3) evaluating the thermal stability of the sample by adopting a thermogravimetric analyzer in nitrogen atmosphere, weighing 10mg of the sample to be measured, placing the sample on a tray balance in a furnace body, covering the furnace body, setting the highest heating temperature to be 800 ℃, controlling the heating rate to be 20 ℃/min until the sample is completely weightless, stopping heating, and performing drawing analysis by using Origin software.
4) Wear resistance: and (4) performing tribology performance test by adopting a four-ball friction wear testing machine. The test conditions are as follows: the rotation speed is 1450r/min at room temperature (25 ℃), and the long grinding time is 30 min. The steel balls are standard grade II GCr15 steel balls produced by Chongqing Steel ball factories, the diameter is 12.7mm, and the hardness is 59-61 HRC. The wear scar diameter of the steel ball is measured, each value is measured for 3 times, and the average value is taken.
5) Biodegradation BDI: reference is made to the literature "Wangkun, Fangjianhua, Chenbowashui, et al. investigation of methods for rapid determination of biodegradability of lubricating oils [ J ]. Petroleum institute (Petroleum processing), 2004,20(6):74-78.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.

Claims (10)

1. A novel plant-based lubricating oil additive is characterized in that the structural formula is as follows:
Figure FDA0002326930070000011
wherein R is1：C8H17、C9H19Or C10H21。
2. A preparation method of a novel plant-based lubricating oil additive is characterized by comprising the following steps: comprises the following steps:
(1) substitution reaction to obtain piperazine derivative, which is marked as C;
(2) and (4) carrying out substitution reaction to obtain a novel plant-based lubricating oil additive, which is marked as E.
3. The method for preparing a novel plant-based lubricant additive according to claim 2, wherein: the step (1) is specifically as follows:
dissolving 1mol of five-membered heterocyclic structure (A) and 0.5-0.6mol of 1, 4-bis (potassium dithioformate) piperazine (B) in 30mol of organic solvent containing 0.5-5 wt% of potassium phosphate, stirring for 1-3h at 5 ℃, continuing to react for 1-2h at normal temperature, standing for 12h, performing suction filtration, and washing with water until the solution is clear; and adding the filter cake into the mixed solvent I, soaking, decoloring, washing, performing suction filtration, and drying at 50-60 ℃ to obtain a substance containing the siloxane modified five-membered heterocyclic structure, which is marked as C.
4. The method for preparing a novel plant-based lubricant additive according to claim 2, wherein: the step (2) is specifically as follows:
dissolving 1mol of C and 2-2.2mol of chlorohydrocarbon (D) in 60mol of saturated organic solvent containing potassium iodide and anhydrous potassium carbonate, mechanically stirring for 40min, and heating and refluxing in water bath for 3-8 h; cooling to room temperature, filtering, taking the filtrate, washing with a mixed solvent II, recrystallizing, filtering, and drying to obtain the novel plant-based lubricating oil additive, which is marked as E.
5. The method for preparing a novel plant-based lubricant additive according to claim 3 or 4, wherein: the organic solvent is N, N-dimethylformamide, tetrahydrofuran, dioxane or acetone.
6. The method for preparing a novel plant-based lubricant additive according to claim 3, wherein: the mixed solvent I is absolute ethyl alcohol/ethyl acetate/acetone according to the volume ratio of 1-2:1-2:2-3, preferably 1:1: 2.
7. The method for preparing the novel plant-based lubricating oil additive according to claim 4, wherein the method comprises the following steps: the mixed solvent II is water/absolute ethyl alcohol/N, N-dimethylformamide according to the volume ratio of 1:2:2-3, preferably 1:2: 2.
8. A plant-based lubricating oil composition is prepared from the following raw materials in parts by weight: 97-99.8 parts of vegetable oil base oil and 0.2-3 parts of novel additive.
9. A plant-based lubricating oil composition according to claim 8, wherein: the vegetable oil base oil is one or more of cottonseed oil, soybean oil, peanut oil, palm oil, castor oil and sunflower seed oil.
10. A plant-based lubricating oil composition according to claim 8, prepared by the process of: mixing the above components at 60-90 deg.C and vacuum degree lower than-0.09 MPa and at 50rps rotation speed for 1h to obtain vegetable lubricating oil product.
CN201911320189.1A 2019-12-19 2019-12-19 Novel plant-based lubricating oil additive and preparation method thereof Withdrawn CN111039899A (en)

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Application publication date: 20200421