CN112480990B - Preparation method of diesel antiwear agent with low freezing point - Google Patents

Preparation method of diesel antiwear agent with low freezing point Download PDF

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CN112480990B
CN112480990B CN202011385577.0A CN202011385577A CN112480990B CN 112480990 B CN112480990 B CN 112480990B CN 202011385577 A CN202011385577 A CN 202011385577A CN 112480990 B CN112480990 B CN 112480990B
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antiwear agent
low
diesel antiwear
freezing point
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CN112480990A (en
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潘龙
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Dalian Daping Oil Chemistry Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
    • B01J35/51—Spheres
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/12—Inorganic compounds
    • C10L1/1233—Inorganic compounds oxygen containing compounds, e.g. oxides, hydroxides, acids and salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/20—Air quality improvement or preservation, e.g. vehicle emission control or emission reduction by using catalytic converters

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

The invention relates to a preparation method of a diesel antiwear agent with a low freezing point, belonging to the technical field of diesel antiwear agents. The preparation method comprises the following steps: adding oleic acid, polyalcohol and the catalyst in claim 5 into a solvent, reacting at 140-145 ℃ for 0.5-1h, then heating to 225-230 ℃ for reaction for 10-20min, cooling to room temperature, then cooling to-25-20 ℃, and filtering to obtain the diesel antiwear agent with low freezing point. The low-freezing point diesel antiwear agent prepared by the invention has a freezing point of-50 ℃ to-40 ℃, and can be used in extremely cold regions.

Description

Preparation method of diesel antiwear agent with low freezing point
Technical Field
The invention relates to a preparation method of a diesel antiwear agent with a low freezing point, belonging to the technical field of diesel antiwear agents.
Background
With the increasing attention of countries in the world to the environmental protection problem, the production of high-quality clean diesel oil for reducing the emission pollution of diesel vehicles has become the development direction of the modern oil refining industry. The diesel oil generally has the characteristics of low sulfur content, low aromatic hydrocarbon content, high cetane number, light fraction and the like. Research shows that sulfur is the most harmful element for increasing HC and CO in diesel engine emissions, especially inhalable particulate matters, so that reducing the sulfur content in diesel is especially important for improving atmospheric pollution. European diesel standard EN590-2009 states that the mass fraction of sulfur does not exceed 0.0010%, and American diesel standard ASTM D975-11 requires that the mass fraction of sulfur in low sulfur diesel does not exceed 0.0015%; the mass fraction of sulfur specified by the national automotive diesel standard GB/T19147-2013 is not more than 0.0050%. The ultra-low sulfur diesel oil standard with the sulfur mass fraction not more than 0.0010 percent has been implemented in Beijing, Shanghai and other areas. Because a harsh hydrodesulfurization process is generally adopted in the production of low-sulfur diesel oil, the contents of polar oxygen-containing compounds, nitrogen-containing compounds, polycyclic aromatic hydrocarbons and bicyclic aromatic hydrocarbons in the diesel oil are reduced, so that the natural lubricating property of the diesel oil is reduced, and the abrasion of fuel injection pumps, such as rotary pumps and distribution pumps, which rely on the diesel oil to lubricate, is caused, and the service life of the fuel injection pumps is greatly reduced.
The addition of lubricity additives, i.e. antiwear agents, to low sulfur diesel is the simplest and widely used method to improve the lubricity of diesel at present. The development of diesel antiwear agents began in the early 90's of the last century by the world's various petroleum companies and additives companies. However, the diesel oil antiwear agent produced by using oleic acid as a raw material has a high freezing point (above-30 ℃), and cannot meet the use requirement at an extremely low temperature.
Disclosure of Invention
The invention solves the problems by improving the preparation method of the diesel antiwear agent.
The invention provides a preparation method of a catalyst for preparing a low-freezing-point diesel antiwear agent, which comprises the following steps: and (3) soaking the porous ceramic microspheres in the suspension of the nano cerium oxide, stirring, taking out, drying, roasting at the temperature of 800-900 ℃ for 5-6h, and cooling to room temperature to obtain the catalyst for preparing the low-freezing-point diesel antiwear agent.
The invention preferably selects the particle size of the porous ceramic microsphere to be 0.5-0.8 mm.
The porosity of the porous ceramic microspheres is 70-90%.
The invention preferably provides that the stirring time is 5-8 h.
The invention also aims to provide a catalyst prepared by the method for preparing the low-freezing-point diesel antiwear agent.
The invention also aims to provide a preparation method of the low-freezing-point diesel antiwear agent, which comprises the following steps: adding oleic acid, polyalcohol and the catalyst into a solvent, reacting at the temperature of 140-145 ℃ for 0.5-1h, then heating to the temperature of 225-230 ℃ for reaction for 10-20min, cooling to room temperature, then cooling to the temperature of-25 ℃ to-20 ℃, and filtering to obtain the low-freezing-point diesel antiwear agent.
The oleic acid, the polyhydric alcohol and the mass ratio of the catalyst to the solvent are preferably 100: 45-60: 0.1-0.5: 20-30.
In the present invention, preferably, the polyhydric alcohol is at least one of ethylene glycol, 1, 2-propylene glycol, glycerol and pentaerythritol.
Preferably, the solvent is xylene.
The invention further aims to provide the diesel anti-wear agent with the low freezing point, which is prepared by the method.
The invention has the beneficial effects that:
the low-freezing point diesel antiwear agent prepared by the invention has a freezing point of-50 ℃ to-40 ℃, and can be used in extremely cold regions.
The diesel antiwear agent with low freezing point prepared by the invention is added into diesel, and has no adverse effect on various indexes of the diesel.
The method for preparing the low-freezing-point diesel antiwear agent is simple, does not discharge acid-base wastewater, and meets the requirement of environmental protection.
The catalyst prepared by the invention has high activity, is not easy to inactivate, and can be repeatedly used for 15-25 times.
Detailed Description
The following non-limiting examples are presented to enable those of ordinary skill in the art to more fully understand the present invention and are not intended to limit the invention in any way.
The particle size of the porous ceramic microspheres is 0.55-0.70mm, and the porosity of the porous ceramic microspheres is 80-90%.
Example 1
A preparation method of a catalyst for preparing a low-freezing-point diesel antiwear agent comprises the following steps: and (3) soaking the porous ceramic microspheres in the suspension of the nano cerium oxide, stirring for 6h, taking out, drying, roasting at 850 ℃ for 5h, and cooling to room temperature to obtain the catalyst for preparing the diesel antiwear agent with the low solidification point.
Example 2
A preparation method of a low-freezing point diesel antiwear agent comprises the following steps: 100g of oleic acid, 45g of ethylene glycol and 0.2g of the catalyst prepared in the example 1 are added into 25g of dimethylbenzene, reacted at 142 ℃ for 45min, heated to 225 ℃ for reaction for 15min, cooled to room temperature, cooled to-25 ℃ and filtered to obtain the low-freezing-point diesel antiwear agent, wherein the yield is 92.9%.
The freezing points of the low freezing point diesel antiwear agent are shown in table 1 below.
The storage stability of the low freezing point diesel antiwear agent is shown in table 2 below.
The low-freezing-point diesel antiwear agent is added into diesel oil, and the diameter of wear spots can be ensured not to be more than 320 mu m after 1 month.
Example 3
A preparation method of a low-freezing point diesel antiwear agent comprises the following steps: 100g of oleic acid, 50g of ethylene glycol and 0.2g of the catalyst prepared in the example 1 are added into 30g of dimethylbenzene, reacted at 143 ℃ for 40min, heated to 228 ℃ for reaction for 17min, cooled to room temperature, cooled to-25 ℃ and filtered to obtain the low-freezing-point diesel antiwear agent, wherein the yield is 93.1%.
The freezing points of the low freezing point diesel antiwear agent are shown in table 1 below.
The storage stability of the low freezing point diesel antiwear agent is shown in table 2 below.
The diesel antiwear agent with the low freezing point is added into diesel, and the diameter of the wear scar can still be ensured to be not more than 320 mu m after 1 month.
Example 4
A preparation method of a low-freezing point diesel antiwear agent comprises the following steps: 100g of oleic acid, 60g of ethylene glycol and 0.25g of the catalyst prepared in the embodiment 1 are added into 25g of dimethylbenzene, reacted for 45min at 142 ℃, heated to 227 ℃ for reaction for 15min, cooled to room temperature, cooled to-25 ℃ and filtered to obtain the low-freezing-point diesel antiwear agent, wherein the yield is 92.1%.
The freezing points of the low freezing point diesel antiwear agent are shown in table 1 below.
The storage stability of the low freezing point diesel antiwear agent is shown in table 2 below.
The diesel antiwear agent with the low freezing point is added into diesel, and the diameter of the wear scar can still be ensured to be not more than 320 mu m after 1 month.
Example 5
A preparation method of a low-freezing point diesel antiwear agent comprises the following steps: the preparation method comprises the following steps: 100g of oleic acid, 55g of 1, 2-propylene glycol and 0.4g of the catalyst prepared in the example 1 are added into 22g of xylene, reacted at 143 ℃ for 40min, heated to 226 ℃ for reaction for 18min, cooled to room temperature, cooled to-25 ℃ and filtered to obtain the diesel antiwear agent with the low freezing point, wherein the yield is 91.1%.
The freezing points of the low freezing point diesel antiwear agent are shown in table 1 below.
The storage stability of the low freezing point diesel antiwear agent is shown in table 2 below.
The diesel antiwear agent with the low freezing point is added into diesel, and the diameter of the wear scar can still be ensured to be not more than 320 mu m after 1 month.
Example 6
A preparation method of a low-freezing point diesel antiwear agent comprises the following steps: the preparation method comprises the following steps: 100g of oleic acid, 58g of 1, 2-propylene glycol and 0.3g of the catalyst prepared in the example 1 are added into 25g of xylene, reacted at 143 ℃ for 40min, heated to 227 ℃ for reaction for 17min, cooled to room temperature, cooled to-25 ℃ and filtered to obtain the low-freezing-point diesel antiwear agent, wherein the yield is 93.8%.
The freezing points of the low freezing point diesel antiwear agent are shown in table 1 below.
The storage stability of the low freezing point diesel antiwear agent is shown in table 2 below.
The diesel antiwear agent with the low freezing point is added into diesel, and the diameter of the wear scar can still be ensured to be not more than 320 mu m after 1 month.
Example 7
A preparation method of a low-freezing point diesel antiwear agent comprises the following steps: the preparation method comprises the following steps: 100g of oleic acid, 47g of 1, 2-propylene glycol and 0.4g of the catalyst prepared in the example 1 are added into 25g of xylene, reacted at 142 ℃ for 42min, heated to 225 ℃ for reaction for 15min, cooled to room temperature, cooled to-25 ℃ and filtered to obtain the low-freezing-point diesel antiwear agent, wherein the yield is 95.2%.
The freezing points of the low freezing point diesel antiwear agent are shown in table 1 below.
The storage stability of the low freezing point diesel antiwear agent is shown in table 2 below.
The diesel antiwear agent with the low freezing point is added into diesel, and the diameter of the wear scar can still be ensured to be not more than 320 mu m after 1 month.
Example 8
A preparation method of a low-freezing point diesel antiwear agent comprises the following steps: 100g of oleic acid, 50g of glycerol and 0.2g of the catalyst prepared in the example 1 are added into 28g of dimethylbenzene, reacted for 50min at 143 ℃, heated to 228 ℃ for reaction for 12min, cooled to room temperature, cooled to-25 ℃ and filtered to obtain the low-freezing-point diesel antiwear agent, wherein the yield is 94.4%.
The freezing points of the low freezing point diesel antiwear agent are shown in table 1 below.
The storage stability of the low freezing point diesel antiwear agent is shown in table 2 below.
The diesel antiwear agent with the low freezing point is added into diesel, and the diameter of the wear scar can still be ensured to be not more than 320 mu m after 1 month.
Example 9
A preparation method of a low-freezing point diesel antiwear agent comprises the following steps: 100g of oleic acid, 52g of glycerol and 0.2g of the catalyst prepared in the example 1 are added into 25g of dimethylbenzene, reacted at 141 ℃ for 55min, heated to 227 ℃ for reaction for 15min, cooled to room temperature, cooled to-25 ℃ and filtered to obtain the low-freezing-point diesel antiwear agent, wherein the yield is 94.7%.
The freezing points of the low freezing point diesel antiwear agent are shown in table 1 below.
The storage stability of the low freezing point diesel antiwear agent is shown in table 2 below.
The diesel antiwear agent with the low freezing point is added into diesel, and the diameter of the wear scar can still be ensured to be not more than 320 mu m after 1 month.
Example 10
A preparation method of a low-freezing point diesel antiwear agent comprises the following steps: 100g of oleic acid, 51g of glycerol and 0.3g of the catalyst prepared in the example 1 are added into 25g of xylene, reacted at 144 ℃ for 40min, heated to 227 ℃ for reaction for 13min, cooled to room temperature, cooled to-25 ℃ and filtered to obtain the low-freezing-point diesel antiwear agent, wherein the yield is 94.2%.
The freezing points of the low freezing point diesel antiwear agent are shown in Table 1 below.
The storage stability of the low freezing point diesel antiwear agent is shown in table 2 below.
The diesel antiwear agent with the low freezing point is added into diesel, and the diameter of the wear scar can still be ensured to be not more than 320 mu m after 1 month.
Example 11
A preparation method of a low-freezing point diesel antiwear agent comprises the following steps: 100g of oleic acid, 49g of pentaerythritol and 0.32g of the catalyst prepared in the example 1 are added into 24g of xylene, reacted at 140 ℃ for 42min, heated to 228 ℃ for reaction for 17min, cooled to room temperature, cooled to-25 ℃ and filtered to obtain the low-freezing-point diesel antiwear agent, wherein the yield is 93.5%.
The freezing points of the low freezing point diesel antiwear agent are shown in table 1 below.
The storage stability of the low freezing point diesel antiwear agent is shown in table 2 below.
The diesel antiwear agent with the low freezing point is added into diesel, and the diameter of the wear scar can still be ensured to be not more than 320 mu m after 1 month.
Example 12
A preparation method of a low-freezing point diesel antiwear agent comprises the following steps: 100g of oleic acid, 53g of pentaerythritol and 0.3g of the catalyst prepared in the example 1 are added into 25g of xylene, reacted at 141 ℃ for 41min, heated to 227 ℃ for reaction for 15min, cooled to room temperature, cooled to-25 ℃ and filtered to obtain the low-freezing-point diesel antiwear agent, wherein the yield is 94.0%.
The freezing points of the low freezing point diesel antiwear agent are shown in table 1 below.
The storage stability of the low freezing point diesel antiwear agent is shown in table 2 below.
The diesel antiwear agent with the low freezing point is added into diesel, and the diameter of the wear scar can still be ensured to be not more than 320 mu m after 1 month.
Example 13
A preparation method of a low-freezing point diesel antiwear agent comprises the following steps: 100g of oleic acid, 55g of pentaerythritol and 0.35g of the catalyst prepared in the example 1 are added into 25g of xylene, reacted at 144 ℃ for 45min, heated to 228 ℃ for reaction for 15min, cooled to room temperature, cooled to-25 ℃ and filtered to obtain the low-freezing-point diesel antiwear agent, wherein the yield is 93.5%.
The freezing points of the low freezing point diesel antiwear agent are shown in table 1 below.
The storage stability of the low freezing point diesel antiwear agent is shown in table 2 below.
The low-freezing-point diesel antiwear agent is added into diesel oil, and the diameter of wear spots can be ensured not to be more than 320 mu m after 1 month.
TABLE 1
Figure BDA0002810897500000081
TABLE 2
Figure BDA0002810897500000091

Claims (6)

1. A preparation method of a catalyst for preparing a low-freezing-point diesel antiwear agent is characterized by comprising the following steps: the preparation method comprises the following steps: soaking the porous ceramic microspheres in the suspension of the nano cerium oxide, stirring, taking out, drying, roasting at 900 ℃ for 5-6h, and cooling to room temperature to obtain a catalyst for preparing the diesel antiwear agent with the low solidification point;
the particle size of the porous ceramic microspheres is 0.5-0.8 mm;
the porosity of the porous ceramic microspheres is 70-90%.
2. The preparation method of the catalyst for preparing the low-freezing-point diesel antiwear agent according to claim 1, wherein the catalyst comprises the following components in percentage by weight: the stirring time is 5-8 h.
3. A catalyst prepared by the method of claim 1 or 2 for use in the preparation of a low freezing point diesel antiwear agent.
4. A preparation method of a low-freezing point diesel antiwear agent is characterized by comprising the following steps: the preparation method comprises the following steps: adding oleic acid, polyalcohol and the catalyst in claim 3 into a solvent, reacting at 140-145 ℃ for 0.5-1h, then heating to 225-230 ℃ for reaction for 10-20min, cooling to room temperature, then cooling to-25-20 ℃, and filtering to obtain the diesel antiwear agent with low freezing point;
the oleic acid, the polyol, the catalyst of claim 3 and the solvent are present in a mass ratio of 100: 45-60: 0.1-0.5: 20-30 parts of;
the polyalcohol is at least one of ethylene glycol, 1, 2-propylene glycol, glycerol and pentaerythritol.
5. The preparation method of the low freezing point diesel antiwear agent according to claim 4, characterized in that: the solvent is xylene.
6. A low freezing point diesel antiwear agent prepared by the method of claim 4 or 5.
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CN106824165A (en) * 2017-04-17 2017-06-13 中国科学技术大学 The preparation method of CeO 2 supporting high-dispersion nano catalyst
CN108947570A (en) * 2018-09-07 2018-12-07 长沙理工大学 A kind of porous ceramics microballoon and preparation method thereof

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陶瓷微球制备工艺的研究进展;朱洪龙;《中国科技信息》;20080615(第12期);第129、131页 *

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Denomination of invention: Preparation method of a low freezing point diesel anti-wear agent

Effective date of registration: 20231116

Granted publication date: 20220705

Pledgee: China Construction Bank Corporation Dalian Jinpu New Area Branch

Pledgor: Dalian Daping Oil Chemistry Co.,Ltd.

Registration number: Y2023980065975

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