CN110396437B - Oil antistatic agent and preparation method and application thereof - Google Patents
Oil antistatic agent and preparation method and application thereof Download PDFInfo
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- CN110396437B CN110396437B CN201910784301.0A CN201910784301A CN110396437B CN 110396437 B CN110396437 B CN 110396437B CN 201910784301 A CN201910784301 A CN 201910784301A CN 110396437 B CN110396437 B CN 110396437B
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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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
-
- 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
-
- 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
- C10L1/16—Hydrocarbons
- C10L1/1608—Well defined compounds, e.g. hexane, benzene
-
- 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
- C10L1/188—Carboxylic acids; metal salts thereof
- C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
-
- 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
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
-
- 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
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2462—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds
- C10L1/2475—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon to carbon bonds
Abstract
The invention discloses an oil antistatic agent, which comprises the following raw materials in parts by weight: 30-48 parts of active component, 10-26 parts of synergist and 6-50 parts of cosolvent, wherein the active component is any one of alkyl polysulfone and alkyl polyamine, or a mixture of alkyl polysulfone and alkyl polyamine; the synergist is any one or more of C3-30 acid; the C3-30 acid is alkyl acid with 3-30 carbon atoms or organic acid containing unsaturated double bonds; meanwhile, the invention also provides a preparation method and application of the oil antistatic agent. The oil antistatic agent provided by the invention is green and environment-friendly; after the additive is added into the oil product according to the concentration of 1-5mg/L, the conductivity of the oil product can be improved to more than 300 pS/m, and the conductivity of the oil product is not obviously reduced after the oil product is placed for 3 months at normal temperature and normal pressure; the antistatic agent has good intersolubility and dispersibility with oil products, and the oil products have good stability after being added.
Description
Technical Field
The invention belongs to the technical field of antistatic additives, and particularly relates to an oil antistatic agent, and a preparation method and application thereof.
Background
According to the requirements of GB 6950-2001 light oil safety static conductivity, the jet fuel safety static conductivity value should be 50-600 pS/m, and the gasoline, kerosene and diesel safety static conductivity value should be greater than 50 pS/m, but with the refined processing of oil products, sulfur, nitrogen, acid and the like with conductivity are all removed, and the weak conductivity of the oil products is eliminated. In order to safely transport, store and use hydrocarbon fuels such as gasoline, diesel oil, kerosene and the like and avoid the occurrence of burning accidents, not only the protection measures are strictly strengthened and the operation is standardized according to the general guidelines for preventing static accidents, but also a proper amount of antistatic agent is necessary to be added so that the hydrocarbon fuels have certain conductivity, the static electricity is prevented and the occurrence of safety accidents is avoided.
The existing oil antistatic agent mainly comprises polyamine, polysulfone and a solvent, but the conductivity of the oil is attenuated and reduced in the using process of the oil antistatic agent, and the performance of the oil is unstable after the oil antistatic agent is added into the oil for a long time, so that the performance indexes of the oil such as vapor pressure, distillation range, copper corrosion and the like are influenced.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides an oil antistatic agent, a preparation method and application thereof.
An oil antistatic agent comprises the following raw materials in parts by weight: 30-48 parts of active component, 10-26 parts of synergist, 6-50 parts of cosolvent,
wherein the active component is any one of alkyl polysulfone and alkyl polyamine, or a mixture of alkyl polysulfone and alkyl polyamine;
the synergist is any one or two of C3-30 acid; the C3-30 acid is alkyl acid with 3-30 carbon atoms or organic acid containing unsaturated double bond.
Preferably, the organic acid is a fatty acid.
Preferably, the synergist is any one or two of C3-28 acid.
Preferably, the synergist is any one or two of C3-24 acid.
Preferably, the synergist is at least one of hexadecenoic acid or octadecenoic acid.
Preferably, the active components are alkyl polysulfone and alkyl polyamine according to the mass ratio of 1: (5-9) the resulting mixture.
Preferably, the cosolvent is any one of toluene and xylene.
Preferably, the alkyl polysulfone is prepared by mixing olefin and sulfur dioxide as raw materials, hydrogen peroxide and paraldehyde as initiators, dodecyl mercaptan as a molecular weight regulator, and the mass ratio of the initiators, the molecular weight regulator and the olefin is 1:1.6:8 under the condition of excessive sulfur dioxide, and then reacting at room temperature for 18 hours to obtain the alkyl polysulfone; wherein the olefin is any one of 1-butene, 1-octene, 1-hexene, 1-dodecene, 1-hexadecene, 1-octadecene and cyclohexene.
Preferably, the alkyl polyamine is prepared by mixing any one of n-butylamine, tetradecylamine, hexadecylamine, dihexadecylamine and octadecylamine, epichlorohydrin and sodium hydroxide according to the mass ratio of 1: 2: 1, and reacting for 18 hours at 50-80 ℃ by using dimethylbenzene as a solvent to obtain the alkyl polyamine.
The preparation method of the oil antistatic agent comprises the steps of sequentially adding the active component and the synergist into the cosolvent, and uniformly stirring and mixing.
The application of the oil antistatic agent in oil products is as follows: the oil antistatic agent is added into oil according to the proportion of 1-5mg/L, and the oil is gasoline, kerosene or diesel oil.
The position, cis-structure and trans-structure of the unsaturated double bond of the organic acid containing the unsaturated double bond do not influence the final effect of the invention, and the organic acid containing the unsaturated double bond in the prior art.
The invention has the advantages that:
the oil antistatic agent provided by the invention does not contain heavy metals, and is green and environment-friendly; after the additive is added into the oil product according to the concentration of 1-5mg/L, the conductivity of the oil product can be improved to more than 300 pS/m, and the conductivity of the oil product is not obviously reduced after the oil product is placed for 3 months at normal temperature and normal pressure; the antistatic agent has good intersolubility and dispersibility with oil products, does not influence performance indexes of the oil products such as vapor pressure, distillation range, copper corrosion and the like after being added, and has good oil product stability.
Detailed Description
Example 1
An oil antistatic agent comprises the following raw materials in parts by weight: 40g of active component, 10g of synergist and 6g of cosolvent,
wherein the active component is tetradecylamine polyamine; the tetradecylamine polyamine is prepared from tetradecylamine, epichlorohydrin and sodium hydroxide according to the mass ratio of 1: 2: 1, mixing, taking dimethylbenzene as a solvent, and reacting for 18 hours at 50 ℃ under the action of sodium hydroxide to obtain the catalyst;
the synergist is hexadecenoic acid;
the cosolvent is toluene;
the preparation method of the oil antistatic agent comprises the following steps: and sequentially adding the active component and the synergist into the cosolvent, and stirring and mixing uniformly.
Example 2
An oil antistatic agent comprises the following raw materials in parts by weight: 48g of active component, 26g of synergist and 50g of cosolvent,
wherein the active component is hexadecene polysulfone; the hexadecene polysulfone is prepared by taking 1-hexadecene and sulfur dioxide as raw materials, taking hydrogen peroxide and paraldehyde as initiators and dodecyl mercaptan as a molecular weight regulator, and reacting at room temperature for 18 hours after the initiators, the molecular weight regulator and the 1-hexadecene are mixed according to the mass ratio of 1:1.6:8 under the condition of excessive sulfur dioxide;
the synergist is propionic acid;
the cosolvent is xylene;
the preparation method of the oil antistatic agent is the same as that of example 1.
Example 3
An oil antistatic agent comprises the following raw materials in parts by weight: 42g of active component, 16g of synergist, 23g of cosolvent,
wherein the active component is a dihexadecylamine polyamine; the bis-hexadecylamine polyamine is prepared by reacting bis-hexadecylamine with epoxy chloropropane and sodium hydroxide according to the mass ratio of 1: 2: 1, mixing, taking dimethylbenzene as a solvent, and reacting for 18 hours at 80 ℃ to obtain the catalyst;
the synergist is a mixture of hexadecenoic acid and octadecenoic acid in an amount of 1: 4;
the cosolvent is toluene;
the preparation method of the oil antistatic agent is the same as that of example 1.
Example 4
An oil antistatic agent comprises the following raw materials in parts by weight: 42g of active component, 14g of synergist and 32g of cosolvent,
the active component is a mixture formed by mixing cyclohexene polysulfone and tetradecylamine polyamine according to the mass ratio of 1: 6; the cyclohexene polysulfone is prepared by taking cyclohexene and sulfur dioxide as raw materials, taking hydrogen peroxide and paraldehyde as initiators, and dodecanethiol as a molecular weight regulator, and reacting at room temperature for 18 hours after the initiators, the molecular weight regulator and the cyclohexene are mixed according to the mass ratio of 1:1.6:8 under the condition of excessive sulfur dioxide; the preparation method of the tetradecylamine polyamine is the same as that of example 1;
the synergist is triacontanoic acid;
the cosolvent is toluene;
the preparation method of the oil antistatic agent is the same as that of example 1.
Example 5
An oil antistatic agent comprises the following raw materials in parts by weight: 30g of active component, 25g of synergist and 30g of cosolvent,
the active component is a mixture formed by mixing octadecene polysulfone and octadecylamine polyamine according to the mass ratio of 1: 9; the octadecylene polysulfone is prepared by taking 1-octadecene and sulfur dioxide as raw materials, taking hydrogen peroxide and paraldehyde as initiators and dodecyl mercaptan as a molecular weight regulator, and reacting at room temperature for 18 hours after the initiators, the molecular weight regulator and the 1-octadecene are mixed according to the mass ratio of 1:1.6:8 under the condition of excessive sulfur dioxide; the octadecylamine polyamine is prepared from octadecylamine, epoxy chloropropane and sodium hydroxide according to the mass ratio of 1: 2: 1, mixing, taking dimethylbenzene as a solvent, and reacting for 18 hours at 60 ℃ to obtain the catalyst;
the synergist is acrylic acid;
the cosolvent is xylene;
the preparation method of the oil antistatic agent is the same as that of example 1.
Example 6
An oil antistatic agent comprises the following raw materials in parts by weight: 38g of active component, 13g of synergist and 28g of cosolvent,
the active component is a mixture formed by mixing butene polysulfone and n-butylamine polyamine according to the mass ratio of 1: 7; the butene polysulfone is prepared by taking 1-butene and sulfur dioxide as raw materials, taking hydrogen peroxide and paraldehyde as initiators and dodecanethiol as a molecular weight regulator, and reacting at room temperature for 18 hours after the initiators, the molecular weight regulator and the 1-butene are mixed according to the mass ratio of 1:1.6:8 under the condition of excessive sulfur dioxide; the n-butylamine polyamine is prepared from n-butylamine, epoxy chloropropane and sodium hydroxide according to the mass ratio of 1: 2: 1, mixing, taking dimethylbenzene as a solvent, and reacting for 18 hours at 70 ℃ to obtain the catalyst;
the synergist is a mixture of propionic acid and hexadecenoic acid substances in an amount of 1: 4;
the cosolvent is toluene;
the preparation method of the oil antistatic agent is the same as that of example 1.
Example 7
An oil antistatic agent comprises the following raw materials in parts by weight: 35g of active component, 10g of synergist and 28g of cosolvent,
wherein the active component is the same as in example 6;
the synergist is a mixture of tetracosanoic acid, octacosanoic acid, tetracosenic acid, octacosenoic acid, acrylic acid, propionic acid and the like in a certain ratio;
the cosolvent is toluene;
the preparation method of the oil antistatic agent is the same as that of example 1.
Example 8
An oil antistatic agent comprises the following raw materials in parts by weight: 35g of active component, 10g of synergist and 23g of cosolvent,
wherein the active component is the same as in example 6;
the synergist is a mixture of docosahexaenoic acid and octadecenoic acid in a mass ratio of 1: 9;
the cosolvent is toluene;
the preparation method of the oil antistatic agent is the same as that of example 1.
Example 9
An oil antistatic agent comprises the following raw materials in parts by weight: 40g of active component, 20g of synergist and 40g of cosolvent,
the active component is a mixture formed by mixing octene polysulfone and hexadecylamine polyamine according to the mass ratio of 1: 5; the octene polysulfone is polymerized by 1-octene and sulfur dioxide, and the hexadecylamine polyamine is polymerized by hexadecylamine and epoxy chloropropane; the octene polysulfone is prepared by taking 1-octene and sulfur dioxide as raw materials, taking hydrogen peroxide and paraldehyde as initiators and dodecyl mercaptan as a molecular weight regulator, and reacting at room temperature for 18 hours after the initiators, the molecular weight regulator and the 1-octene are mixed according to the mass ratio of 1:1.6:8 under the condition of excessive sulfur dioxide; the hexadecylamine polyamine is prepared by mixing hexadecylamine, epoxy chloropropane and sodium hydroxide according to the mass ratio of 1: 2: 1, mixing, taking dimethylbenzene as a solvent, and reacting for 18 hours at 80 ℃ to obtain the catalyst;
the synergist is dodecanoic acid;
the cosolvent is xylene;
the preparation method of the oil antistatic agent is the same as that of example 1.
Example 10
An oil antistatic agent comprises the following raw materials in parts by weight: 39g of active component, 10g of synergist and 23g of cosolvent,
wherein the active component is the same as in example 6;
the synergist is tetracosenic acid;
the cosolvent is toluene;
the preparation method of the oil antistatic agent is the same as that of example 1.
Example 11
An oil antistatic agent comprises the following raw materials in parts by weight: 35g of active component, 20g of synergist and 30g of cosolvent,
wherein the active component is cyclohexene polysulfone, and the preparation method is the same as that of the embodiment 4;
the synergist is eicosapentaenoic acid;
the cosolvent is toluene;
the preparation method of the oil antistatic agent is the same as that of example 1.
Performance testing
1. Adding the oil antistatic agent described in example 3 into 93# base gasoline, and detecting the conductivity of the oil antistatic agent; the results are shown in Table 1, using the antistatic agent without the synergist as comparative example 3 and the other examples as example 3.
TABLE 1 Effect of antistatic agent content on gasoline conductivity
Meanwhile, the properties of the gasoline to which the antistatic agent described in example 3 was added were measured at an amount of 1 mg/L, and the results are shown in Table 2.
TABLE 2 analysis of gasoline properties after addition of antistatic agent
2. Adding the oil antistatic agent described in example 4 into 93# base gasoline, and detecting the conductivity of the oil antistatic agent; the results are shown in Table 3, which shows the results of comparative example 4, which is an antistatic agent without the addition of a synergist, and the results of other examples 4.
TABLE 3 Effect of antistatic agent content on gasoline conductivity
3. The oil antistatic agent described in example 7 was added to diesel oil and its conductivity was measured; the results are shown in Table 4, which shows the results of comparative example 7, which is an antistatic agent without the addition of a synergist, and the results of other examples 7.
TABLE 4 Effect of antistatic agent content on Diesel conductivity
4. The oil antistatic agent described in example 11 was added to diesel oil and the conductivity was measured; the results are shown in Table 5, which shows comparative example 11, which is an antistatic agent without the addition of a synergist, and other examples 11.
TABLE 5 Effect of antistatic agent content on Diesel conductivity
Claims (7)
1. An oil antistatic agent is characterized in that: the feed comprises the following raw materials in parts by weight: 30-48 parts of active component, 10-26 parts of synergist, 6-50 parts of cosolvent,
wherein the active component is any one of alkyl polysulfone and alkyl polyamine, or a mixture of alkyl polysulfone and alkyl polyamine;
the synergist is any one or more of C3-30 acid;
the C3-30 acid is alkyl acid with 3-30 carbon atoms or organic acid containing unsaturated double bonds;
the cosolvent is any one of toluene and xylene;
the alkyl polysulfone is prepared by mixing olefin and sulfur dioxide as raw materials, hydrogen peroxide and paraldehyde as initiators, dodecyl mercaptan as a molecular weight regulator, and reacting at room temperature for 18 hours after the initiators, the molecular weight regulator and the olefin are mixed according to the mass ratio of 1:1.6:8 under the condition of excessive sulfur dioxide; wherein the olefin is any one of 1-butene, 1-octene, 1-hexene, 1-dodecene, 1-hexadecene, 1-octadecene and cyclohexene;
wherein the alkyl polyamine is prepared from any one of n-butylamine, tetradecylamine, hexadecylamine, dihexadecylamine and octadecylamine, epichlorohydrin and sodium hydroxide according to the mass ratio of 1: 2: 1, and reacting for 18 hours at 50-80 ℃ by using dimethylbenzene as a solvent to obtain the alkyl polyamine.
2. The oil antistatic agent as claimed in claim 1, characterized in that: the organic acid is a fatty acid.
3. The oil antistatic agent according to claim 1 or 2, characterized in that: the synergist is any one or two of C3-28 acid.
4. The oil antistatic agent according to claim 1 or 2, characterized in that: the synergist is any one or two of C3-24 acid.
5. The oil antistatic agent as claimed in claim 1, characterized in that: the active components are alkyl polysulfone and alkyl polyamine according to the mass ratio of 1: (5-9) the resulting mixture.
6. The process for the preparation of the oil antistatic agent according to claim 1, characterized in that: and sequentially adding the active component and the synergist into the cosolvent, and stirring and mixing uniformly.
7. The use of the oil antistatic agent of claim 1 in oils, characterized by: the application is that the oil antistatic agent is added into oil according to the proportion of 1-5mg/L, and the oil is gasoline, kerosene or diesel oil.
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| CN113528202B (en) * | 2021-07-30 | 2022-10-21 | 东营天喜化工有限公司 | Antistatic agent special for light fuel oil, preparation method and application |
| CN114806657B (en) * | 2022-06-13 | 2023-07-28 | 中国航空油料有限责任公司 | Antistatic additive for jet fuel and preparation method thereof |
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| PT2132284E (en) * | 2007-03-02 | 2010-12-20 | Basf Se | Additive formulation suited for anti-static finishing and improvement of the electrical conductivity of inanimate organic material |
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| US3674450A (en) * | 1971-04-23 | 1972-07-04 | Cities Service Oil Co | Antistatic additive for hydrocarbon fuels |
| CN101974358A (en) * | 2010-10-26 | 2011-02-16 | 陕西科技大学 | Oil antistatic agent and preparation method thereof |
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| CN106190369A (en) * | 2016-07-14 | 2016-12-07 | 西北大学 | A kind of hydrophobic type polyquaternary ammonium salt oil antistatic agent and preparation method thereof |
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