WO2021244385A1 - 一种含氮柴油降凝剂组合物及其制备和应用 - Google Patents

一种含氮柴油降凝剂组合物及其制备和应用 Download PDF

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WO2021244385A1
WO2021244385A1 PCT/CN2021/096307 CN2021096307W WO2021244385A1 WO 2021244385 A1 WO2021244385 A1 WO 2021244385A1 CN 2021096307 W CN2021096307 W CN 2021096307W WO 2021244385 A1 WO2021244385 A1 WO 2021244385A1
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pour point
point depressant
diesel
depressant composition
nitrogen
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PCT/CN2021/096307
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English (en)
French (fr)
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蔺华林
殷素雅
李欣
袁铭霞
解麦莹
陈凤飞
杨太顺
韩生
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上海应用技术大学
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Priority to US17/927,696 priority Critical patent/US11999919B2/en
Publication of WO2021244385A1 publication Critical patent/WO2021244385A1/zh

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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
    • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
    • 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
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
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    • 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
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    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
    • C10L10/16—Pour-point depressants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • 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
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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    • 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
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • 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
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • 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
    • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
    • C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
    • C10L2200/0446—Diesel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/34—Applying ultrasonic energy

Definitions

  • the invention belongs to the technical field of diesel pour point depressants, and relates to a nitrogen-containing diesel pour point depressant composition and its preparation and application.
  • Diesel has attracted much attention because of its durability, high efficiency, cleanliness, and storage safety.
  • the low-temperature fluidity of diesel fuel restricts its performance. Therefore, people's demand for low-pour point diesel, especially diesel with low cold filter plugging point, is even more urgent.
  • adding a pour point depressant to produce low-pour point diesel can broaden the diesel distillation range and save resources; at the same time, it has the characteristics of flexible operation, low cost, quick effect and retention of high cetane wax components, which is a kind of increase in production.
  • Diesel pour point depressant also known as low temperature fluidity improver, is an important fuel additive in diesel production. It can significantly change the low temperature fluidity of diesel and reduce the freezing point and cold filter plugging point when the amount of addition is small.
  • the diesel pour point depressants currently on the market have problems such as large additions and insufficient dispersibility.
  • the purpose of the present invention is to provide a nitrogen-containing diesel fuel pour point depressant composition and its preparation and application, which has the advantages of good solubility in diesel oil, small dosage and obvious pour point and filter reduction effects.
  • One of the technical solutions of the present invention provides a nitrogen-containing diesel pour point depressant composition, which is composed of the following components by weight percentage:
  • N-tetradecyl methacrylamide-tetradecyl methacrylate is made of N-tetradecyl methacrylamide and tetradecyl methacrylate in toluene as a solvent, and benzyl peroxide Acyl is obtained by reaction under the condition of initiator. Furthermore, the molar ratio of N-tetradecyl methacrylamide and tetradecyl methacrylate is 1:10. Furthermore, the reaction temperature is 120°C and the time is 8h.
  • Tetradecyl methacrylamide not only provides long alkyl chains, but also has amide groups, so N-hexadecyl methacrylamide-tetradecyl methacrylate polymer has abundant long chains And polar groups provide abundant crystallization sites. Polar groups can delay the precipitation of wax crystals and repel the accumulation of wax crystals.
  • Monoisopropanolamine, cyclohexane, and polyethylene glycol are selected as co-solvents mixed with pour point depressants and added to diesel in a small amount to improve the susceptibility of pour point depressants and diesel.
  • polyethylene glycol is polyethylene glycol 200.
  • the second technical solution of the present invention provides a method for preparing a nitrogen-containing diesel pour point depressant composition.
  • N-tetradecyl methacrylamide-tetradecyl methacrylate and monoisopropanol are weighed according to the metering ratio.
  • the amine, cyclohexane and polyethylene glycol are stirred uniformly and dispersed by ultrasonic to obtain the target product.
  • stirring temperature is 25-30°C
  • ultrasonic dispersion time is 10-20 min.
  • the third technical solution of the present invention provides an application of a nitrogen-containing diesel pour point depressant composition.
  • the nitrogen-containing diesel pour point depressant composition is added to diesel, mixed uniformly and ultrasonically dispersed.
  • the mass ratio of the nitrogen-containing diesel fuel pour point depressant composition to the diesel fuel is 1:100-1000.
  • the mixing temperature is 30-45°C
  • the ultrasonic dispersion time is 30 min.
  • diesel is preferably 0# diesel on the market.
  • the present invention limits the addition amount of other additives and polymer pour point depressants, in which the concentration of one component is reduced, and the concentration of the pour point depressant is affected, and the pour point depressant effect is reduced.
  • the addition amount of N-tetradecyl methacrylamide-tetradecyl methacrylate is very important.
  • the addition amount of pour point depressant is small, there is not enough non-polar long-chain alkanes and diesel fuel in the system. The normal alkanes are eutectic, and there are not enough polar groups to maintain the stability of the wax crystals in the system.
  • the added amount of pour point depressant is too much, the polymer will agglomerate, causing the opposite effect. Therefore, the right amount of polymer can exert the best effect of pour point depressant.
  • the present invention has the following advantages:
  • N-tetradecyl methacrylamide-tetradecyl methacrylate plays the main role of depressing pour point, it accounts for a relatively high proportion, and the crystallization method of diesel is changed through the effects of eutectic, adsorption, etc. , It can effectively improve the low-temperature fluidity of diesel oil.
  • the cyclohexane and polyethylene glycol (200) components contained in it are good pour point depressant additives, so that the pour point depressant composition is evenly dispersed in the diesel oil.
  • N-10 Tetraalkyl methacrylamide-tetradecyl methacrylate and monoisopropanolamine have a synergistic effect, thereby further enhancing the pour point depressing effect.
  • the cold filter plugging point measurement method of the present invention is based on "SH/T0248-2006 Diesel and Civil Heating Oil Cold Filter Filtering Point Measurement Method", and the freezing point measurement method is based on "GB510-83 Petroleum Products Freezing Point Measurement”.
  • N-tetradecyl methacryloyl is obtained by acylation reaction. Under the condition of N,N dimethylformamide as a solvent, the acid binding agent and tetradecyl amine are stirred and dissolved, and then methacryloyl chloride is added. After reacting for 2h, N-tetradecyl methacrylamide is obtained after washing and drying.
  • N-tetradecyl methacrylamide-tetradecyl methacrylate consists of N-tetradecyl methacrylamide and tetradecyl methacrylate in a monomer molar ratio of 1:10, and the reaction temperature is 120°C. Toluene is used as the solvent and benzoyl peroxide is used as the initiator to react for 8 hours.
  • a pour point depressant composition for diesel fuel which is made by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate, monoisopropanolamine, cyclohexane and polyethylene glycol (200), Calculated by mass percentage, the composition and content of its raw materials are as follows:
  • the ratio of diesel pour point depressant composition: diesel is calculated by mass ratio, preferably 1:200, and the diesel pour point depressant composition is 0.1
  • the mass ratio of% is added to 60g Songjiang 0# diesel oil, mixed and stirred uniformly at a temperature of 50° C., and ultrasonically dispersed for 15 minutes to obtain diesel fuel containing the diesel fuel pour point depressant composition.
  • a pour point depressant composition for diesel fuel which is made by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate, monoisopropanolamine, cyclohexane and polyethylene glycol (200), Calculated by mass percentage, the composition and content of its raw materials are as follows:
  • the ratio of diesel pour point depressant composition: diesel is calculated by mass ratio, preferably 1:200, and the diesel pour point depressant composition is 0.1
  • the mass ratio of% is added to 60g Songjiang 0# diesel oil, mixed and stirred uniformly at a temperature of 50° C., and ultrasonically dispersed for 15 minutes to obtain diesel fuel containing the diesel fuel pour point depressant composition.
  • a pour point depressant composition for diesel fuel which is made by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate, monoisopropanolamine, cyclohexane and polyethylene glycol (200), Calculated by mass percentage, the composition and content of its raw materials are as follows:
  • the ratio of diesel pour point depressant composition: diesel is calculated by mass ratio, preferably 1:200, and the diesel pour point depressant composition is 0.1
  • the mass ratio of% is added to 60g Songjiang 0# diesel oil, mixed and stirred uniformly at a temperature of 50° C., and ultrasonically dispersed for 15 minutes to obtain diesel fuel containing the diesel fuel pour point depressant composition.
  • a pour point depressant composition for diesel fuel which is made by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate, monoisopropanolamine, cyclohexane and polyethylene glycol (200), Calculated by mass percentage, the composition and content of its raw materials are as follows:
  • the ratio of diesel pour point depressant composition: diesel is calculated by mass ratio, preferably 1:200, and the diesel pour point depressant composition is 0.1
  • the mass ratio of% is added to 60g Songjiang 0# diesel oil, mixed and stirred uniformly at a temperature of 50° C., and ultrasonically dispersed for 15 minutes to obtain diesel fuel containing the diesel fuel pour point depressant composition.
  • a pour point depressant composition for diesel fuel which is made by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate, monoisopropanolamine, cyclohexane and polyethylene glycol (200), Calculated by mass percentage, the composition and content of its raw materials are as follows:
  • the ratio of diesel pour point depressant composition: diesel is calculated by mass ratio, preferably 1:200, and the diesel pour point depressant composition is 0.1
  • the mass ratio of% is added to 60g Songjiang 0# diesel oil, mixed and stirred uniformly at a temperature of 50° C., and ultrasonically dispersed for 15 minutes to obtain diesel fuel containing the diesel fuel pour point depressant composition.
  • a pour point depressant composition for diesel fuel which is made by mixing N-tetradecyl methacrylamide-tetradecyl methacrylate, monoisopropanolamine, cyclohexane and polyethylene glycol (200), Calculated by mass percentage, the composition and content of its raw materials are as follows:
  • the ratio of diesel pour point depressant composition: diesel is calculated by mass ratio, preferably 1:200, and the diesel pour point depressant composition is 0.1
  • the mass ratio of% is added to 60g Songjiang 0# diesel oil, mixed and stirred uniformly at a temperature of 50° C., and ultrasonically dispersed for 15 minutes to obtain diesel fuel containing the diesel fuel pour point depressant composition.
  • the N-tetradecyl methacrylamide-tetradecyl methacrylate pour point depressant used in Example 1 is not mixed with monoisopropanolamine, cyclohexane and polyethylene glycol (200). Directly add 0.1% of the mass ratio to 60g Songjiang 0# diesel oil, mix and stir uniformly at a temperature of 50°C, and then ultrasonically disperse for 15 minutes. After testing, the freezing point and cold filter plugging point of Songjiang 0# diesel oil after addition are reduced by 19 °C and 7°C.
  • N-tetradecyl methacrylamide-tetradecyl methacrylate, monoisopropanolamine, cyclohexane and polyethylene glycol (200) are mixed
  • the composition of the diesel pour point depressant composition improves the solubility and dispersibility of the pour point depressant in diesel fuel through the solvent, and through the synergistic effect between the pour point depressants, improves the pour point depressant effect and improves Low temperature fluidity of diesel.
  • the commercially available polymethyl acrylate pour point depressant T1804 is used in diesel pour point depressant.
  • the ratio of pour point depressant to diesel oil is calculated by mass ratio, preferably 1:200, and the diesel oil pour point depressant composition is 0.1% of the mass ratio is added to 60 g Songjiang 0# diesel oil and mixed and stirred uniformly at a temperature of 50° C., and ultrasonically dispersed for 15 minutes to obtain diesel oil containing the diesel oil pour point depressant composition.
  • the freezing point and cold filter plugging point of the commercially available 0# diesel fuel containing the diesel fuel pour point depressant composition obtained in the test of the aforementioned comparative example 2 were reduced by 19°C and 6°C, respectively.
  • the diesel pour point depressant composition formed by mixing is more sensitive to diesel and has a better pour point depressant effect.
  • Example 1 Compared with Example 1, most of them are the same, except that the monoisopropanolamine is changed to N-tetradecyl methacrylamide-tetradecyl methacrylate of equal mass.
  • the freezing point and cold filter plugging point of commercial 0# diesel fuel containing the diesel fuel pour point depressant composition obtained by the test of the aforementioned comparative example 3 were reduced by 20°C and 9°C, respectively.
  • the diesel pour point depressant composition formed by mixing is more sensitive to diesel and has a better pour point depressant effect.
  • Example 2 Compared with Example 1, most of them are the same, except that the polyethylene glycol is changed to cyclohexane of equal mass.
  • the freezing point and cold filter plugging point of the commercially available 0# diesel fuel containing the diesel fuel pour point depressant composition obtained in the test of Comparative Example 4 were reduced by 19°C and 8°C, respectively.
  • the diesel pour point depressant composition formed by mixing is more sensitive to diesel and has a better pour point depressant effect.
  • Example 1 Compared with Example 1, most of them are the same, except that the cyclohexane is changed to polyethylene glycol of the same mass.
  • the freezing point and cold filter plugging point of commercial 0# diesel fuel containing the diesel fuel pour point depressant composition obtained in the test of the aforementioned comparative example 5 were reduced by 20°C and 7°C, respectively.
  • the diesel pour point depressant composition formed by mixing is more sensitive to diesel and has a better pour point depressant effect.

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Abstract

本发明涉及一种含氮柴油降凝剂组合物及其制备和应用，该含氮柴油降凝剂组合物由以下重量百分比的组分组成：单异丙醇胺10-40％；环己烷10-40％；聚乙二醇0-20％；N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯40-60％。将所得的柴油降凝剂组合物添加到市售0#柴油中，其冷凝点和冷滤点分别降低21-25℃和9-13℃。

Description

一种含氮柴油降凝剂组合物及其制备和应用 技术领域
本发明属于柴油降凝剂技术领域，涉及一种含氮柴油降凝剂组合物及其制备和应用。
背景技术
柴油因其耐用、高效、清洁、存储安全等特点，而倍受人们的关注。但是柴油的低温流动性能却制约着其使用性能，因此人们对低凝柴油特别是低冷滤点的柴油的需求更是迫切。比起其它工艺，添加降凝剂生产低凝柴油，可拓宽柴油馏程，节约资源；同时具有操作灵活、费用低、见效快和保留高十六烷值蜡组分等特点，是一种增产高品质柴油的有效方法。柴油降凝剂又称低温流动性改进剂，是柴油生产中一种重要的燃料添加剂，它在加入量很少时即能显著改变柴油的低温流动性能，降低凝点和冷滤点。但是，目前市面上的柴油降凝剂都具有添加量大，分散性不足等问题。
发明内容
本发明的目的就是为了提供一种含氮柴油降凝剂组合物及其制备和应用，具有在柴油中溶解性好，用量小且降凝降滤效果明显等优点。
本发明的目的可以通过以下技术方案来实现：
本发明的技术方案之一提供了一种含氮柴油降凝剂组合物，由以下重量百分比的组分组成：
Figure PCTCN2021096307-appb-000001
进一步的，所述的N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯由N-十四烷基甲基丙烯酰胺和甲基丙烯酸十四酯在甲苯做溶剂、过氧化苯甲酰为引发剂的条件下反应得到。更进一步的，N-十四烷基甲基丙烯酰胺和甲基丙烯酸十四酯的摩尔比为1:10。更进一步的，反应温度为120℃，时间为8h。此方法将含氮极性基团引入聚合物中，并通过加入一定比例的助溶剂，使聚合物降凝剂的降凝效果有所提升，且实验过程简单、操作方便。十四烷基甲基丙烯酰胺在提供烷基长链的同时，还带有酰胺基团，因此N-十六烷基甲基丙烯酰胺-甲基丙烯酸十四酯聚合物中具有丰富的长链和极性基团，提供了丰富结晶位点，极性基团可延迟蜡晶的析出并排斥蜡晶的堆积。选择了单异丙醇胺、环己烷、聚乙二醇作为助溶剂与降凝剂混合微量加入到柴油中，提高降凝剂与柴油的感受性。
进一步的，其由以下重量百分比的组分组成：
Figure PCTCN2021096307-appb-000002
进一步的，聚乙二醇为聚乙二醇200。
本发明的技术方案之二提供了一种含氮柴油降凝剂组合物的制备方法，按计量比称取N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇搅拌均匀，超声分散，即得到目的产物。
更进一步的，搅拌的温度为25-30℃，超声分散的时间为10-20min。
本发明的技术方案之三提供了一种含氮柴油降凝剂组合物的应用，使用时，将含氮柴油降凝剂组合物加入到柴油中，混合均匀并超声分散。
进一步的，含氮柴油降凝剂组合物与柴油的质量比为1:100-1000。
进一步的，混合的温度为30-45℃，超声分散的时间为30min。
进一步的，柴油优选为市售0#柴油。
本发明对其他助剂与聚合物降凝剂的添加量做出了限定，其中一组分浓度降低，降凝剂的浓度受到影响，则降凝效果有所下降。N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯的添加量是十分重要的，当降凝剂的添加量较少时，体系内没有足够的非极性长链烷烃与柴油的正构烷烃发生共晶，也没有足够极性基团保持体系内蜡晶的稳定。当降凝剂的添加量过多时，聚合物会发生团聚，造成相反的效果。因此适量的聚合物才能发挥出降凝剂最佳的效果。
与现有技术相比，本发明具有以下优点：
(1)由于所含的N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯起到主要降凝作用，它所占比例较高，通过共晶、吸附等作用改变柴油的结晶方式，能够有效改善柴油的低温流动性，所含环己烷和聚乙二醇(200)组分是良好的降凝剂助剂，使降凝剂组合物均匀分散在柴油中，同时N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯和单异丙醇胺起协同作用，从而进一步增强降凝效果。
(2)只需在超声波处理器上进行超声分散即可，其制备工艺简单、操作方便、效果明显。
(3)可提高降凝剂在市售0#柴油中的分散性，可使其冷凝点降低21-25℃、冷滤点降低9-13℃。
具体实施方式
下面结合具体实施例对本发明进行详细说明。本实施例以本发明技术方案为前提进行实施，给出了详细的实施方式和具体的操作过程，但本发明的 保护范围不限于下述的实施例。
本发明中冷滤点的测量方法依据《SH/T0248-2006柴油和民用取暖油冷滤点测定法》进行，冷凝点的测量方法依据《GB510-83石油产品凝点测定》进行。
本发明所用原料：
Figure PCTCN2021096307-appb-000003
N-十四烷基甲基丙烯酰是通过酰基化反应得到的，在N,N二甲基甲酰胺作为溶剂条件下，将缚酸剂和十四胺搅拌溶解，再加入甲基丙烯酰氯，反应2h，水洗干燥后得到N-十四烷基甲基丙烯酰胺。N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯由N-十四烷基甲基丙烯酰胺和甲基丙烯酸十四酯在单体摩尔比1:10，反应温度为120℃，甲苯做溶剂，过氧化苯甲酰为引发剂反应8小时得到。
其余如无特别说明的原料或处理技术，则表明均为本领域的常规市售原料或常规处理技术。
实施例1：
一种柴油的降凝剂组合物，由N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇(200)混合而成，按质量百分比计算，其原料组成及含量如下：
Figure PCTCN2021096307-appb-000004
上述的柴油的降凝剂组合物在柴油降凝中的应用，柴油的降凝剂组合物：柴油的比例，按质量比计算，优选为1:200，将柴油的降凝剂组合物按0.1％的质量比加入到60g松江0#柴油中50℃的温度下混合搅拌均匀后，超声分散15min，即得含有该柴油降凝剂组合物的柴油。
经测试上述实施例1所得的含有上述柴油降凝剂组合物的市售0#柴油的冷凝点和冷滤点分别降低25℃和13℃。
实施例2
一种柴油的降凝剂组合物，由N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇(200)混合而成，按质量百分比计算，其原料组成及含量如下：
Figure PCTCN2021096307-appb-000005
上述的柴油的降凝剂组合物在柴油降凝中的应用，柴油的降凝剂组合物：柴油的比例，按质量比计算，优选为1:200，将柴油的降凝剂组合物按0.1％的质量比加入到60g松江0#柴油中50℃的温度下混合搅拌均匀后，超声分散15min，即得含有该柴油降凝剂组合物的柴油。
经测试上述实施例2所得的含有上述柴油降凝剂组合物的市售0#柴油的冷凝点和冷滤点分别降低24℃和12℃。
实施例3
一种柴油的降凝剂组合物，由N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇(200)混合而成，按质量百分比计算，其原料组成及含量如下：
Figure PCTCN2021096307-appb-000006
上述的柴油的降凝剂组合物在柴油降凝中的应用，柴油的降凝剂组合物：柴油的比例，按质量比计算，优选为1:200，将柴油的降凝剂组合物按0.1％的质量比加入到60g松江0#柴油中50℃的温度下混合搅拌均匀后，超声分散15min，即得含有该柴油降凝剂组合物的柴油。
经测试上述实施例3所得的含有上述柴油降凝剂组合物的市售0#柴油的冷凝点和冷滤点分别降低23℃和11℃。
实施例4
一种柴油的降凝剂组合物，由N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇(200)混合而成，按质量百分比计算，其原料组成及含量如下：
Figure PCTCN2021096307-appb-000007
上述的柴油的降凝剂组合物在柴油降凝中的应用，柴油的降凝剂组合物：柴油的比例，按质量比计算，优选为1:200，将柴油的降凝剂组合物按0.1％的质量比加入到60g松江0#柴油中50℃的温度下混合搅拌均匀后，超声分散 15min，即得含有该柴油降凝剂组合物的柴油。
经测试上述实施例4所得的含有上述柴油降凝剂组合物的市售0#柴油的冷凝点和冷滤点分别降低22℃和10℃。
实施例5
一种柴油的降凝剂组合物，由N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇(200)混合而成，按质量百分比计算，其原料组成及含量如下：
Figure PCTCN2021096307-appb-000008
上述的柴油的降凝剂组合物在柴油降凝中的应用，柴油的降凝剂组合物：柴油的比例，按质量比计算，优选为1:200，将柴油的降凝剂组合物按0.1％的质量比加入到60g松江0#柴油中50℃的温度下混合搅拌均匀后，超声分散15min，即得含有该柴油降凝剂组合物的柴油。
经测试上述实施例5所得的含有上述柴油降凝剂组合物的市售0#柴油的冷凝点和冷滤点分别降低21℃和10℃。
实施例6
一种柴油的降凝剂组合物，由N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇(200)混合而成，按质量百分比计算，其原料组成及含量如下：
Figure PCTCN2021096307-appb-000009
上述的柴油的降凝剂组合物在柴油降凝中的应用，柴油的降凝剂组合物：柴油的比例，按质量比计算，优选为1:200，将柴油的降凝剂组合物按0.1％的质量比加入到60g松江0#柴油中50℃的温度下混合搅拌均匀后，超声分散15min，即得含有该柴油降凝剂组合物的柴油。
经测试上述实施例5所得的含有上述柴油降凝剂组合物的市售0#柴油的冷凝点和冷滤点分别降低21℃和9℃。
对比例1
将实施例1中所使用的N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯降凝剂不与单异丙醇胺、环己烷和聚乙二醇(200)混合使用，直接按0.1％的质量比加入到60g松江0#柴油中50℃的温度下混合搅拌均匀后，超声分散15min，经测试，加剂后的松江0#柴油的冷凝点和冷滤点分别降低19℃和7℃。
通过上述实施例和对比例1进行对比，可以看出N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇(200)混合而组成的柴油降凝剂组合物，即通过溶剂提高了降凝剂在柴油中的溶解性和分散性并通过降凝剂之间的协同作用，提高了降凝剂的降凝效果，改善了柴油的低温流动性。
对比例2
优选市售的聚甲酯丙烯酸酯类降凝剂T1804在柴油降凝中的应用，降凝剂与柴油的比例，按质量比计算，优选为1:200，将柴油的降凝剂组合物按0.1％的质量比加入到60g松江0#柴油中50℃的温度下混合搅拌均匀后，超声分散15min，即得含有该柴油降凝剂组合物的柴油。
经测试上述对比例2所得的含有上述柴油降凝剂组合物的市售0#柴油的冷凝点和冷滤点分别降低19℃和6℃。
通过上述实施例和应用实施例2进行对比，可以看出N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇(200)混合而组成的柴油降凝剂组合物对柴油的感受性更强，降凝效果更佳。
对比例3：
与实施例1相比，绝大部分都相同，除了将单异丙醇胺改为等质量的N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯。
经测试上述对比例3所得的含有上述柴油降凝剂组合物的市售0#柴油的冷凝点和冷滤点分别降低20℃和9℃。
通过上述实施例和应用实施例1进行对比，可以看出N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇(200)混合而组成的柴油降凝剂组合物对柴油的感受性更强，降凝效果更佳。
对比例4：
与实施例1相比，绝大部分都相同，除了将聚乙二醇改为等质量的环己烷。
经测试上述对比例4所得的含有上述柴油降凝剂组合物的市售0#柴油的冷凝点和冷滤点分别降低19℃和8℃。
通过上述实施例和应用实施例1进行对比，可以看出N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇(200)混合而组成的柴油降凝剂组合物对柴油的感受性更强，降凝效果更佳。
对比例5：
与实施例1相比，绝大部分都相同，除了将环己烷改为等质量的聚乙二醇。
经测试上述对比例5所得的含有上述柴油降凝剂组合物的市售0#柴油的冷凝点和冷滤点分别降低20℃和7℃。
通过上述实施例和应用实施例1进行对比，可以看出N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇(200)混合而组成的柴油降凝剂组合物对柴油的感受性更强，降凝效果更佳。
上述的对实施例的描述是为便于该技术领域的普通技术人员能理解和使用发明。熟悉本领域技术的人员显然可以容易地对这些实施例做出各种修改， 并把在此说明的一般原理应用到其他实施例中而不必经过创造性的劳动。因此，本发明不限于上述实施例，本领域技术人员根据本发明的揭示，不脱离本发明范畴所做出的改进和修改都应该在本发明的保护范围之内。

Claims (10)

  1. 一种含氮柴油降凝剂组合物，其特征在于，由以下重量百分比的组分组成：
    Figure PCTCN2021096307-appb-100001
  2. 根据权利要求1所述的一种含氮柴油降凝剂组合物，其特征在于，所述的N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯由N-十四烷基甲基丙烯酰胺和甲基丙烯酸十四酯在甲苯做溶剂、过氧化苯甲酰为引发剂的条件下反应得到。
  3. 根据权利要求2所述的一种含氮柴油降凝剂组合物，其特征在于，N-十四烷基甲基丙烯酰胺和甲基丙烯酸十四酯的摩尔比为1:10。
  4. 根据权利要求2所述的一种含氮柴油降凝剂组合物，其特征在于，反应温度为120℃，时间为8h。
  5. 根据权利要求1所述的一种含氮柴油降凝剂组合物，其特征在于，其由以下重量百分比的组分组成：
    Figure PCTCN2021096307-appb-100002
  6. 如权利要求1-5任一所述的一种含氮柴油降凝剂组合物的制备方法，其特征在于，按计量比称取N-十四烷基甲基丙烯酰胺-甲基丙烯酸十四酯、单异丙醇胺、环己烷和聚乙二醇搅拌均匀，超声分散，即得到目的产物。
  7. 根据权利要求6所述的一种含氮柴油降凝剂组合物的制备方法，其特 征在于，搅拌的温度为25-30℃，超声分散的时间为10-20min。
  8. 如权利要求1-5任一所述的一种含氮柴油降凝剂组合物的应用，其特征在于，使用时，将含氮柴油降凝剂组合物加入到柴油中，混合均匀并超声分散。
  9. 根据权利要求8所述的一种含氮柴油降凝剂组合物的应用，其特征在于，含氮柴油降凝剂组合物与柴油的质量比为1:100-1000。
  10. 根据权利要求8所述的一种含氮柴油降凝剂组合物的应用，其特征在于，混合的温度为30-45℃，超声分散的时间为30min。
PCT/CN2021/096307 2020-05-30 2021-05-27 一种含氮柴油降凝剂组合物及其制备和应用 WO2021244385A1 (zh)

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