The effect of methacrylate ternary polymer on the low-temperature flowability of coal-based diesel

doi:10.21203/rs.3.rs-4817062/v1

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The effect of methacrylate ternary polymer on the low-temperature flowability of coal-based diesel

https://doi.org/10.21203/rs.3.rs-4817062/v1

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In this study, tetradecyl methacrylate-maleic anhydride-benzylidene acetone (C₁₄MC-MA-MCA) terpolymers were synthesized via free radical polymerization and evaluated as pour point depressants (PPDs) for coal-based diesel. The findings indicate that the C₁₄MC-MA-MCA (3:1:1) terpolymer exhibited the most effective inhibition of the solid point (SP) at 1500 ppm concentration. Specifically, it reduced the SP of coal-based diesel from − 4 ℃ to -42 ℃, marking a significant decrease of 38 ℃. Furthermore, the crystallization behavior and SP reduction mechanism of C₁₄MC-MA-MCA in coal-based diesel were investigated using viscosity analysis and polarized optical microscopy (POM).

word

Coal-based diesel

Low temperature fluidity

Terpolymers

Solid Point

Three-dimensional net structure

Coal-based diesel is produced through the catalytic hydrogenation liquefaction of coal at high temperatures and pressures, resulting in a liquid hydrocarbon fuel. However, this diesel contains a high concentration of n-paraffins, which are distributed unevenly and contribute to poor low-temperature fluidity. At colder temperatures, these high-melting-point paraffins precipitate from the diesel due to van der Waals forces ^[1], forming wax crystals. As temperature decreases, the accumulation of these crystals intensifies, eventually creating a complex network structure that impedes the flow of diesel ^[2–3]. This solidification process poses significant challenges for agricultural production and transportation in our daily life ^[4–6]. One effective solution to enhance the low-temperature flow properties of coal-based diesel is the addition of Pour Point Depressants (PPDs), which remains the simplest and most efficient method.

Currently, the most commonly used PPDs to improve the low-temperature fluidity of diesel include ethylene vinyl acetate copolymers ^[7], maleic anhydride copolymers ^[8–9], and α-alkenes polymers ^[10–11]. However, these PPDs may suffer from limitations such as uneven dispersion and poor solubility, which can restrict their effectiveness in enhancing diesel's low-temperature fluidity ^[12–16]. In contrast, methacrylate copolymers are known for their excellent dispersion and solubility, offering significant improvements in diesel ^[17–18]. Han et al ^[19] examined the impact of methacrylic acid ester-maleic anhydride copolymers on diesel's low-temperature fluidity, demonstrating a 19°C reduction in Solid Point (SP) with the addition of 500 ppm. Similarly, Song et al ^[20] introduced C₁₄MC-MA aniline as a PPD, achieving a 16°C SP reduction with 2000 ppm added to diesel.

Currently, PPDs are widely employed to enhance the low-temperature fluidity of petroleum-based diesel, yet there is a notable lack of research on their effectiveness for coal-based diesel. Addressing this gap, this study focuses on synthesizing a range of C₁₄MC-MA-MCA (methyl methacrylate tetradecyl terpolymers) specifically tailored for coal-based diesel. The research evaluates their impact on improving the low-temperature fluidity of coal-derived diesel. Additionally, the study investigates the crystallization behavior and crystal morphology of diesel both with and without these PPDs using viscosity analysis and polarized optical microscopy (POM).

2.1. Materials

Tetradecyl ester (C₁₄MC) and C₁₄MC-MA-MCA were synthesized and purified in the laboratory. 1-tetradecanol, methacrylic acid, maleic anhydride (MA), benzylidene acetone (MCA), p-toluenesulfonic acid (PTSA), hydroquinone, toluene and benzoyl peroxide (BPO) are all analytical grade reagents and purchased from Aladdin Chemical Reagent Co. without further purification. Coal-based diesel was selected from Xuanli Company.

2.2. Synthesis and characterization of C₁₄MC-MA-MCA terpolymers

Firstly, tetradecyl methacrylate (C₁₄MC) was synthesized by esterification of methacrylic acid and 1-tetradecanol, the molar ratio of methacrylic acid to 1-tetradecanol was 1.2:1, toluene was used as solvent, hydroquinone was used as inhibitor, PTSA was used as catalyst, and water was separated by azeotrope in Dean-Stark apparatus. Then, C₁₄MC, MA, and MCA were prepared by a free radical polymerization reaction at the indicated molar ratios to produce C₁₄MC-MA-MCA ternary copolymers. The resulting polymer is called C₁₄MC-MA-MCA(1:1:1)、C₁₄MC-MA-MCA(2:1:1)、C₁₄MC-MA-MCA(3:1:1)、C₁₄MC-MA-MCA(4:1:1)、C₁₄MC-MA-MCA(5:1:1)、C₁₄MC-MA-MCA(6:1:1). The synthesis process of C₁₄MC-MA-MCA is shown in Fig. 1. A further detail is provided in the Supplemental File.

2.3. Analysis of Coal-based diesel

Table 1

Physicochemical characteristics of coal-based diesel
Test	Method	Coal-based diesel	petroleum diesel
Cold filter plugging point (℃)	SH/T 0248	4	-2
Solid point (℃)	GB/T 510	-4	-7
Kinematic viscosity at 20 ℃ (mm² s)	GB/T 265	4.24	3.23
Acid value (mg of KOH/100 ml)	GB/T 258	0.5	1.81
N-paraffins hydrocarbon (wt. %)	GC-MS	84.18	89.2
Iso-paraffins hydrocarbon (wt. %)	GC-MS	15.82	10.8

The physical and chemical characteristics of coal-based and petroleum-based diesel, along with their respective test methods, are illustrated in Fig. 2 and Table 1. Compared to petroleum-based diesel, coal-based diesel exhibits approximately 5% lower saturated alkane content ^[23]. However, it has higher Cold Filter Plugging Point (CFPP) and SP, indicating poorer low-temperature fluidity. Figure 4 illustrates that the distribution range of n-alkanes in coal-based diesel and petroleum-based diesel is broad, spanning from 8 to 24 carbons. Notably, the n-alkane distribution in coal-based diesel is uneven, predominantly falling between 11 to 16 and 20 to 23 carbons. In contrast, the distribution in petroleum-based diesel is more uniform, primarily between 11 and 22 carbons. This disparity likely contributes to the higher CFPP and SP values observed in coal-based diesel compared to petroleum-based diesel. Specifically, coal-based diesel contains the highest proportion of C₁₄ n-alkanes, at 9.86%. Therefore, adhering to the principle of carbon chain compatibility, the alkyl ester chain length is determined as C₁₄ during the synthesis of the ternary polymer.

2.4. Tests of cold flow properties

SP is the highest temperature at which diesel sample loses fluidity, and it is the most important index to evaluate the cold flow performance of diesel. 500, 1000, 1500 and 2000 ppm C₁₄MC-MA-MCA were mixed with the coal-based diesel and sonicated at 50 ℃ for 45 min. According to GB/T510 standard method, the SP of diesel samples before and after C₁₄MC-MA-MCA treatment was measured by A1121S automatic pour point measuring instrument (Delite, Beijing).

2.5. Viscosity and POM measurements

Viscosity is an important rheological parameter that mainly affects the flow characteristics of diesel. According to the GB/T265 standard method, the viscosity of diesel samples before and after C₁₄MC-MA-MCA treatment was measured by A1010 kinematic viscosity tester (Delite, Beijing), and draw its temperature viscosity curve.

DM2500P polarizing optical microscopy (Leica, Germany) was used to observe the change of crystal behavior of diesel samples before and after C₁₄MC-MA-MCA treatment at low temperature at 100× magnification. The cooling rate was 2 ℃/min.

3.1. Characterization of the chemical structures of the PPDs

The chemical structure of C₁₄MC-MA-MCA trimer were analyzed using FT-IR and ¹H NMR spectroscopy (Figure S4 and S5; detailed spectra are provided in the Supplemental File). The molecular weight and polydispersity index of C₁₄MC-MA-MCA were determined through gel permeation chromatography (GPC), as shown in Table 2. The weight-average molecular weight (Mw) of C₁₄MC-MA-MCA ranged from 2.35×10⁴ to 3.50×10⁴ g/mol, with a number-average molecular weight (Mn) ranging from 0.85×10⁴ to 1.24×10⁴ g/mol. Previous studies suggest that molecular weights between 0.40×10⁴ and 10×10⁴ g/mol exhibit excellent performance ^{[21, 23]}. Furthermore, the polydispersity index (Mw/Mn) ranged from 2.296 to 3.809, showing an increasing trend with higher proportions of monomers. This indicates that as the monomer ratio increases, the polymer's molecular weight distribution widens and its polydispersity increases.

Table 2

Molecular weight of C₁₄MC-MA-MCA
Copolymer	Mw (g/mol)	Mn (g/mol)	Mw/Mn
C₁₄MC-MA-MCA(1:1:1)	26011	11331	2.296
C₁₄MC-MA-MCA(2:1:1)	23469	9103	2.578
C₁₄MC-MA-MCA(3:1:1)	34973	12407	2.819
C₁₄MC-MA-MCA(4:1:1)	28594	8507	3.361
C₁₄MC-MA-MCA(5:1:1)	32346	8492	3.809
C₁₄MC-MA-MCA(6:1:1)	31322	11885	2.635

3.2. Effect of C14MC-MA-MCA on the cold flow properties of diesel

The changes in SP of coal-based diesel before and after treatment with C₁₄MC-MA-MCA at different dosages are illustrated in Fig. 3. ΔSP denotes the difference in SP of the diesel before and after treatment with C₁₄MC-MA-MCA. As depicted in Fig. 6, across the range of 500–2000 ppm, all variants of C14MC-MA-MCA exhibited significant reductions in SP, with ΔSP values exceeding 25℃. Initially, the reduction in SP increased with increasing additive concentration, peaking at C₁₄MC-MA-MCA (3:1:1) at 1500 ppm, where SP decreased from − 4℃ to -42℃, a decrease of 38℃. However, beyond 1500 ppm, the SP reduction effect weakened. This is attributed to the optimal dosage of PPDs preventing the formation of a network structure of wax crystals, thereby lowering the diesel's SP. Yet, excessive PPDs can lead to more crystallization points, facilitating the formation of a layered network that diminishes the SP-lowering effect.

Moreover, the monomer ratio of C₁₄MC-MA-MCA significantly influences its effectiveness in reducing diesel SP. At 1500 ppm, C₁₄MC-MA-MCA (5:1:1) and C₁₄MC-MA-MA (2:1:1) lowered SP from − 4℃ to -37℃, a reduction of 33℃, which was notably less effective than C₁₄MC-MA-MCA (3:1:1). This difference arises because lower monomer ratios result in fewer side-chain alkyl esters in PPDs, reducing their adsorption on n-alkanes and allowing larger wax crystals to form and precipitate more easily. Conversely, higher proportions of alkyl esters provide more crystallization sites,enhancing adsorption of n-alkanes and promoting the bonding of wax crystals into a three-dimensional network structure resembling diesel wax crystals, thereby weakening the SP-lowering effect. Hence, C₁₄MC-MA-MCA (3:1:1) is optimal based on these findings.

3.3. Viscosity analysis

At the same temperature, diesel exhibits better fluidity with lower viscosity. A temperature-viscosity curve serves to illustrate diesel's fluidity across different temperatures. Figure 4 displays these curves for coal-based diesel before and after treatment with C₁₄MC-MA-MCA. As depicted, the addition of PPDs shows no impact on diesel viscosity above 5 ℃, indicating excellent dispersibility of C₁₄MC-MA-MCA in diesel. Generally, diesel viscosity increases as temperature decreases. However, the addition of C₁₄MC-MA-MCA notably mitigates this viscosity rise. Particularly, C₁₄MC-MA-MCA (3:1:1) demonstrates the most effective viscosity reduction, reducing diesel viscosity at -7 ℃ from 17.56 mPa·s to 7.53 mPa·s—a 57.12% decrease when added at 1500 ppm. This outcome aligns with C₁₄MC-MA-MCA's inhibitory effect on wax crystal formation. The long-chain alkyl side of C₁₄MC-MA-MCA efficiently adsorbs n-alkanes in diesel, while MA and MCA enhance wax crystal dispersion and inhibit crystal growth, significantly enhancing diesel's low-temperature fluidity by reducing viscosity

3.4. DSC analysis

Table 3

Data Analysis of the DSC Curves
Samples	T _onset (°C)	T _peak (°C)	T _endset (°C)	ΔH (J/g)
Untreated diesel	7.68	2.68	-43.39	15.21
Diesel + C₁₄MC-MA-MCA(3:1:1)1500ppm	8.19	3.19	-43.15	13.79
Diesel + C₁₄MC-MA-MCA(5:1:1)1500ppm	8.19	3.19	-43.26	14.31
Diesel + C₁₄MC-MA-MCA(5:1:1)500ppm	7.19	2.69	-43.85	14.35

The DSC curves and analysis of diesel before and after treatment with C₁₄MC-MA-MCA are presented in Fig. 5 and Table 3. T_onset indicates the onset temperature of the peak, marking the temperature at which wax crystals begin to precipitate. The slope of the peak reflects the rate of wax crystal deposition in diesel, while ΔH represents the enthalpy of the liquid-solid phase transition, indicating wax crystals dispersion stability in low-temperature conditions.

The results show that the T_onset and T_peak of untreated coal-based diesel are 7.68 ℃ and 2.68 ℃, diesel treated with C₁₄MC-MA-MCA shows minimal change in T_onset (ranging from 7.19 ℃ to 8.19 ℃) and T_peak (ranging from 2.69 ℃ to 3.19 ℃). Furthermore, C₁₄MC-MA-MCA treatment does not alter the slope of the diesel DSC curve. This suggests that the addition of PPDs has negligible influence on the temperature at which wax crystals initiate precipitation in diesel, so does it affect the rate of wax crystal precipitation. The ΔH of treated coal-based diesel is significantly lower than that of untreated diesel, indicating improved dispersion stability post C₁₄MC-MA-MCA treatment. Specifically, the ΔH of C₁₄MC-MA-MCA (3:1:1) treated diesel is notably lower than that of C₁₄MC-MA-MCA (5:1:1). Among these, the diesel treated with 1500 ppm of C₁₄MC-MA-MCA (3:1:1) exhibits the lowest ΔH (13.79 J/g), highlighting wax crystals superior dispersion stability in coal-based diesel ^[23–24]. These findings are consistent with the analyses presented in Fig. 4.

3.5. POM analysis

POM can visually observe the crystal shape, size, dispersion, and their changes with external temperature of diesel wax. Figure 6 presents POM images of coal-based diesel before and after treatment with 1500 ppm of C₁₄MC-MA-MCA (3:1:1) at -10 ℃ and − 20 ℃. In Fig. 6a, at -10 ℃, untreated diesel shows large-scale layered wax structures with particle sizes around 30 µm. When the temperature drops to -20 ℃, particle sizes increase to approximately 40–50 µm, with thicker layered wax crystals forming a dense three-dimensional network. This contributes to reduced fluidity in coal-based diesel. In Fig. 6b, after treatment with 1500 ppm of C₁₄MC-MA-MCA (3:1:1), notable changes are observed in the shape, size, and quantity of wax crystals. Larger wax crystals (> 20 µm) are seldom seen. At -10 ℃, wax crystals are smaller and more numerous, exhibiting a rice-like structure measuring about 30 µm in length and 5 µm in width. Upon further cooling to -20°C, there are no significant changes in shape and size, but there is a marked increase in the quantity of wax crystals. This suggests that after C₁₄MC-MA-MCA (3:1:1) treatment, wax crystals struggle to form a continuous layered network structure. Consequently, the treatment notably enhances the low-temperature fluidity of coal-based diesel. These findings align with the analysis results depicted in Figs. 3–4.

3.6. Mechanism analysis

According to the experimental results, the molecular mechanism of C₁₄MC-MA-MCA was examined, as illustrated in Fig. 7. At lower temperatures, n-alkanes present in coal-based diesel tend to precipitate into layered structures that stack together, forming a three-dimensional network and ultimately causing solidification of the diesel. Upon adding C₁₄MC-MA-MCA to coal-based diesel, several effects are observed: firstly, C₁₄MC-MA-MCA provides numerous alkyl ester side chains which act as nucleation sites for wax crystals. Secondly, the lone electron pairs on the oxygen atom of the MA group contribute to a higher electron cloud density within the wax crystal and these lone pairs also have the capacity to alter the direction of wax crystal growth. Additionally, the MCA group exhibits pronounced steric effects, hindering wax crystal contact. Consequently, the wax crystals within the system become uniformly charged and repel each other, increasing the interfacial tension of the wax crystals/oil phase ^[22]. This leads to reduced wax crystal volume and dispersed structure, thereby enhancing the dispersion capability within coal-based diesel. Ultimately, these effects significantly improve the low-temperature fluidity of coal-based diesel.

A series of C₁₄MC-MA-MCA terpolymers was prepared using C₁₄MC, MA, and MCA as raw materials, and characterization by FT-IR and ¹H NMR. Among these, C₁₄MC-MA-MCA (3:1:1) exhibited the most significant enhancement in low-temperature fluidity of coal-based diesel, reducing the SP from − 4 ℃ to -42 ℃, a decrease of 38 ℃. Viscosity, DSC and POM analyses indicate that C₁₄MC-MA-MCA provides numerous alkyl ester side chains that act as nucleation sites for wax crystals. Additionally, the lone pair electrons in the MA group of C₁₄MC-MA-MCA influence the growth direction of wax crystals, while the MCA groups introduce significant steric hindrance effects that impede wax crystal contact. As a result, treatment with C₁₄MC-MA-MCA reduces the volume of wax crystals in coal-based diesel and disperses their structure more effectively throughout the fuel. This dispersion significantly improves the low-temperature fluidity of coal-based diesel.

Acknowledgements

This study was funded by the Major Science and Technology Project of Xinjiang Uygur Autonomous Region, China (2021A01002-1), and the author thanks Xinjiang Xuanli Environmental Protection Energy Co., Ltd. for providing the coal-based diesel.

Disclosure of interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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You are reading this latest preprint version

The effect of methacrylate ternary polymer on the low-temperature flowability of coal-based diesel

Status:

Version 1

Abstract

Figures

1. Introduction

2. Experimental

2.1. Materials

2.2. Synthesis and characterization of C₁₄MC-MA-MCA terpolymers

2.3. Analysis of Coal-based diesel

2.4. Tests of cold flow properties

2.5. Viscosity and POM measurements

3. Results and discussion

3.1. Characterization of the chemical structures of the PPDs

3.2. Effect of C14MC-MA-MCA on the cold flow properties of diesel

3.3. Viscosity analysis

3.4. DSC analysis

3.5. POM analysis

3.6. Mechanism analysis

4. Conclusions

Declarations

References

Additional Declarations

Supplementary Files

Status:

Version 1

The effect of methacrylate ternary polymer on the low-temperature flowability of coal-based diesel

Status:

Version 1

Abstract

Figures

1. Introduction

2. Experimental

2.1. Materials

2.2. Synthesis and characterization of C14MC-MA-MCA terpolymers

2.3. Analysis of Coal-based diesel

2.4. Tests of cold flow properties

2.5. Viscosity and POM measurements

3. Results and discussion

3.1. Characterization of the chemical structures of the PPDs

3.2. Effect of C14MC-MA-MCA on the cold flow properties of diesel

3.3. Viscosity analysis

3.4. DSC analysis

3.5. POM analysis

3.6. Mechanism analysis

4. Conclusions

Declarations

References

Additional Declarations

Supplementary Files

Status:

Version 1

2.2. Synthesis and characterization of C₁₄MC-MA-MCA terpolymers