A compound, a method of preparing the same, and a composition containing the same

Abstract

The application provides a compound, a preparation method thereof and a composition containing the compound. A structural formula of the compound is shown as formula I. The preparation method of the compound is as follows: mixing diisopropanolamine and ethylene glycol diglycidyl ether, adding the mixture into a reaction kettle, adding a solvent, and reacting at 80-120 DEG C for 4-8 h, and then distilling at 50-80 DEG C under reduced pressure, collecting the distillation product, and obtaining the compound; mixing the compound and N-methyldiethanolamine in a mass ratio of (1-2):(2-3), and uniformly mixing to obtain a 20-60 wt% aqueous solution, and obtaining the composition.

Description

Technical Field

[0001] This invention belongs to the field of natural gas development technology, and particularly relates to a compound, its preparation method, and compositions containing the compound. Background Technology

[0002] Natural gas, as a valuable resource, has extremely wide applications in production and daily life. With its rising status in the global energy structure, the importance of the natural gas purification industry is also increasing. During natural gas development, natural gas resources are often accompanied by acidic gases such as H2S and CO2. These acidic gases inevitably corrode pipelines and other equipment during extraction, gathering, transportation, and storage, leading to reduced equipment lifespan and safety hazards. Furthermore, hydrogen sulfide, as a toxic substance, along with associated and secondary hydrogen sulfide, poses potential safety hazards to oil well workers and nearby residents. In addition, excessively high concentrations of hydrogen sulfide and other gases in natural gas can significantly impact its sales. After decades of research, my country has made some progress in natural gas desulfurization, but there is still a gap compared to advanced international levels. For the removal of sulfides during oil and gas field extraction and gathering, the most commonly used method in industry is wet desulfurization. This process is simple, highly efficient, and environmentally friendly, making it well-suited for large-scale natural gas production and transportation. However, currently, amine desulfurization technology is the most widely used wet desulfurization method. Among them, MDEA (methyl diethanolamine) has become the most widely used desulfurization solvent in amine desulfurization due to its advantages such as high acid load, good selectivity for H2S, low corrosivity, and low foaming. However, using MDEA alone is difficult to solve various complex engineering problems.

[0003] Although existing technologies for desulfurizing agents based on amines have high absorption rates and certain selective absorption effects on H2S gas, these steric hindrance-based desulfurizing agents are currently unable to meet the increasingly stringent desulfurization requirements in natural gas development. Summary of the Invention

[0004] In view of the fact that conventional alcohol amine desulfurizing agents used in existing wet desulfurization technologies are gradually failing to meet the increasingly stringent desulfurization requirements in natural gas development, this invention provides a compound, its preparation method, and a composition containing the compound.

[0005] One aspect of the present invention provides a compound having the structural formula shown in Formula I.

[0006]

[0007] The second invention provides a method for preparing the compound as described in the first invention, comprising the following steps:

[0008] 1) React diisopropanolamine and ethylene glycol diglycidyl ether to obtain the reactants;

[0009] 2) The reactants are distilled to obtain the compound.

[0010] In one specific embodiment, the molar ratio of diisopropanolamine to ethylene glycol diglycidyl ether is (2 to 3):(1 to 2);

[0011] Preferably, the molar ratio of diisopropanolamine to ethylene glycol diglycidyl ether is 3:2.

[0012] In one specific embodiment, in step 1), diisopropanolamine and ethylene glycol diglycidyl ether are mixed with a first solvent and then reacted;

[0013] Preferably, the total mass of the diisopropanolamine, ethylene glycol diglycidyl ether, and the first solvent is 100%, and the amount of the first solvent is 60 wt% to 80 wt%.

[0014] Preferably, the first solvent is selected from at least one of water, methanol, and ethanol;

[0015] Preferably, the first solvent is methanol.

[0016] In one specific embodiment, in step 1), the reaction temperature is 80 to 120°C; and / or

[0017] The reaction lasts for 4 to 8 hours;

[0018] Preferably, the reaction temperature is 120°C;

[0019] Preferably, the reaction lasts for 8 hours.

[0020] In one specific embodiment, in step 2), the distillation product is collected after distillation to obtain the compound;

[0021] Preferably, the distillation is vacuum distillation;

[0022] Preferably, the distillation temperature is 50 to 80°C;

[0023] Preferably, the distillation temperature is 80°C.

[0024] The third invention provides a composition comprising a compound and N-methyldiethanolamine;

[0025] The compound is either the compound described in one of the present inventions or the compound prepared by the method described in another of the present inventions.

[0026] In one specific embodiment, the mass ratio of the compound to N-methyldiethanolamine is (1 to 2):(2 to 3);

[0027] Preferably, the mass ratio of the compound to N-methyldiethanolamine is 1:3.

[0028] In one specific embodiment, the composition further includes a second solvent;

[0029] Preferably, the second solvent is water;

[0030] The total mass of the composition is 100%, and the total mass of the compound and the N-methyldiethanolamine accounts for 20 wt% to 60 wt% of the composition;

[0031] Preferably, the total mass of the composition is 100%, and the total mass of the compound and the N-methyldiethanolamine accounts for 50 wt% of the composition.

[0032] The application of any one of the compounds described in one of the present inventions, the compounds prepared by the method described in the second of the present invention, and the compositions described in the third of the present invention in desulfurization, particularly in natural gas desulfurization.

[0033] The beneficial effects of this invention are:

[0034] To address the problem that conventional alkanolamine desulfurizers used in existing wet desulfurization technologies cannot meet the increasingly stringent desulfurization requirements in natural gas development, this invention provides a compound, its preparation method, and a composition containing the compound. When the compound is prepared into a 50 wt% aqueous solution, its desulfurization efficiency can reach up to 99.85%, and its selective absorption coefficient for hydrogen sulfide can reach up to 8.77. When the compound is combined with the traditional desulfurizer N-methyldiethanolamine to obtain the composition, the composition's desulfurization efficiency can reach up to 99.9%, and its selective absorption coefficient for hydrogen sulfide can still reach up to 8.85. The desulfurization effect is superior to using the traditional desulfurizer N-methyldiethanolamine alone, and the cost is low. The compound and its composition exhibit fast absorption rate, high absorption capacity, and good selectivity for hydrogen sulfide, demonstrating excellent desulfurization performance. Furthermore, they are simple and convenient to prepare, reusable, and have promising application prospects. Attached Figure Description

[0035] Figure 1 This is the chemical reaction equation for the synthesis of the compound. Detailed Implementation

[0036] The present invention will be further described below with reference to the embodiments. However, the embodiments of the present invention are merely illustrative examples and should not be construed as limiting the present invention under any circumstances.

[0037] Preparation of compounds

[0038] Example 1

[0039] First, 2 mol of diisopropanolamine (i.e., 266.38 g of diisopropanolamine) and 1 mol of ethylene glycol diglycidyl ether (i.e., 174.19 g of ethylene glycol diglycidyl ether) were mixed evenly and added to a reaction vessel. 1321.71 g of methanol was added as a solvent. The reaction was carried out at 120 °C for 8 hours. After cooling, the mixture was poured out and distilled under reduced pressure at 50 °C. The distilled product was collected to obtain the crude compound in solid state.

[0040] Example 2

[0041] First, 3 mol of diisopropanolamine (i.e., 399.57 g of diisopropanolamine) and 1 mol of ethylene glycol diglycidyl ether (i.e., 174.19 g of ethylene glycol diglycidyl ether) were mixed evenly and added to a reaction vessel. 860.64 g of methanol was added as a solvent. The reaction was carried out at 120 °C for 8 hours. After cooling, the mixture was poured out and distilled under reduced pressure at 50 °C. The distilled product was collected to obtain the crude compound in solid state.

[0042] Example 3

[0043] First, 3 mol of diisopropanolamine (i.e., 399.57 g of diisopropanolamine) and 2 mol of ethylene glycol diglycidyl ether (i.e., 348.38 g of ethylene glycol diglycidyl ether) were mixed evenly and added to a reaction vessel. 1121.93 g of methanol was added as a solvent. The reaction was carried out at 120 °C for 8 hours. After cooling, the mixture was poured out and distilled under reduced pressure at 50 °C. The distilled product was collected to obtain the crude compound in solid state.

[0044] Example 4

[0045] First, 3 mol of diisopropanolamine (i.e., 399.57 g of diisopropanolamine) and 2 mol of ethylene glycol diglycidyl ether (i.e., 348.38 g of ethylene glycol diglycidyl ether) were mixed evenly and added to a reaction vessel. 1451.90 g of methanol was added as a solvent. The reaction was carried out at 120 °C for 8 hours. After cooling, the mixture was poured out and distilled under reduced pressure at 80 °C. The distilled product was collected to obtain the crude compound in solid state.

[0046] Example 5

[0047] First, 3 mol of diisopropanolamine (i.e., 399.57 g of diisopropanolamine) and 2 mol of ethylene glycol diglycidyl ether (i.e., 348.38 g of ethylene glycol diglycidyl ether) were mixed evenly and added to a reaction vessel. 1329.69 g of methanol was added as a solvent. The reaction was carried out at 80 °C for 4 h. After cooling, the mixture was poured out and distilled under reduced pressure at 50 °C. The distilled product was collected to obtain the crude compound in solid state.

[0048] Example 6

[0049] First, 3 mol of diisopropanolamine (i.e., 399.57 g of diisopropanolamine) and 2 mol of ethylene glycol diglycidyl ether (i.e., 348.38 g of ethylene glycol diglycidyl ether) were mixed evenly and added to a reaction vessel. 1329.69 g of methanol was added as a solvent. The reaction was carried out at 120 °C for 4 h. After cooling, the mixture was poured out and distilled under reduced pressure at 80 °C. The distilled product was collected to obtain the crude compound in solid state.

[0050] Example 7

[0051] First, 2 mol of diisopropanolamine (i.e., 266.38 g of diisopropanolamine) and 2 mol of ethylene glycol diglycidyl ether (i.e., 348.38 g of ethylene glycol diglycidyl ether) were mixed evenly and added to a reaction vessel. 922.14 g of water was added as a solvent. The reaction was carried out at 100°C for 6 hours. After cooling, the mixture was poured out and distilled under reduced pressure at 65°C. The distilled product was collected to obtain the crude compound in solid state.

[0052] Example 8

[0053] First, 2 mol of diisopropanolamine (i.e., 266.38 g of diisopropanolamine) and 2 mol of ethylene glycol diglycidyl ether (i.e., 348.38 g of ethylene glycol diglycidyl ether) were mixed evenly and added to a reaction vessel. 1434.44 g of ethanol was added as a solvent. The reaction was carried out at 100°C for 6 hours. After cooling, the mixture was poured out and distilled under reduced pressure at 65°C. The distilled product was collected to obtain the crude compound in solid state.

[0054] Example 9

[0055] First, 2 mol of diisopropanolamine (i.e., 266.38 g of diisopropanolamine) and 2 mol of ethylene glycol diglycidyl ether (i.e., 348.38 g of ethylene glycol diglycidyl ether) were mixed evenly and added to a reaction vessel. 2459.04 g of ethanol was added as a solvent. The reaction was carried out at 100°C for 6 hours. After cooling, the mixture was poured out and distilled under reduced pressure at 65°C. The distilled product was collected to obtain the crude compound in solid state.

[0056] Formulation of the composition

[0057] Example 10

[0058] The crude compound obtained in Example 1 and N-methyldiethanolamine were mixed evenly at a mass ratio of 1:3, and water was added to prepare an aqueous solution to obtain the composition; the mass of the composition was 100%, and the total content of the crude compound obtained in Example 1 and N-methyldiethanolamine in the composition was 50 wt%.

[0059] Example 11

[0060] The crude compound obtained in Example 2 and N-methyldiethanolamine were mixed evenly at a mass ratio of 1:2, and water was added to prepare an aqueous solution to obtain a composition. The mass of this composition was 100%, and the total content of the crude compound obtained in Example 2 and N-methyldiethanolamine in the composition was 50 wt%.

[0061] Example 12

[0062] The crude compound obtained in Example 3 and N-methyldiethanolamine were mixed evenly at a mass ratio of 1:2, and water was added to prepare an aqueous solution to obtain a composition. The mass of this composition was 100%, and the total content of the crude compound obtained in Example 3 and N-methyldiethanolamine in the composition was 50 wt%.

[0063] Example 13

[0064] The crude compound obtained in Example 4 and N-methyldiethanolamine were mixed evenly at a mass ratio of 1:3, and water was added to prepare an aqueous solution to obtain a composition. The mass of this composition was 100%, and the total content of the crude compound obtained in Example 4 and N-methyldiethanolamine in the composition was 50 wt%.

[0065] Example 14

[0066] The crude compound obtained in Example 5 and N-methyldiethanolamine were mixed evenly at a mass ratio of 1:3, and water was added to prepare an aqueous solution to obtain a composition. The mass of this composition was 100%, and the total content of the crude compound obtained in Example 5 and N-methyldiethanolamine in the composition was 50 wt%.

[0067] Example 15

[0068] The crude compound obtained in Example 6 and N-methyldiethanolamine were mixed evenly at a mass ratio of 2:3, and water was added to prepare an aqueous solution to obtain a composition. The mass of this composition was 100%, and the total content of the crude compound obtained in Example 6 and N-methyldiethanolamine in the composition was 50 wt%.

[0069] Example 16

[0070] The crude compound obtained in Example 7 and N-methyldiethanolamine were mixed evenly at a mass ratio of 2:2, and water was added to prepare an aqueous solution to obtain the composition. The mass of the composition was 100%, and the total content of the crude compound obtained in Example 7 and N-methyldiethanolamine in the composition was 20 wt%.

[0071] Example 17

[0072] The crude compound obtained in Example 8 and N-methyldiethanolamine were mixed evenly at a mass ratio of 2:2, and water was added to prepare an aqueous solution to obtain the composition. The mass of the composition was 100%, and the total content of the crude compound obtained in Example 8 and N-methyldiethanolamine in the composition was 40 wt%.

[0073] Example 18

[0074] The crude compound obtained in Example 9 and N-methyldiethanolamine were mixed evenly at a mass ratio of 2:2, and water was added to prepare an aqueous solution to obtain a composition. The mass of this composition was 100%, and the total content of the crude compound obtained in Example 9 and N-methyldiethanolamine in the composition was 60 wt%.

[0075] Comparative Example 1

[0076] N-methyldiethanolamine was mixed with water to prepare an aqueous solution to obtain a comparative composition. The mass of the comparative composition was 100%, and the content of N-methyldiethanolamine in the comparative composition was 40 wt%.

[0077] Comparative Example 2

[0078] The ethylene glycol diglycidyl ether in Example 4 was replaced with an equal amount of diethylene glycol monoethyl ether, and everything else was the same as in Example 4, to obtain the crude comparative compound.

[0079] Comparative Example 3

[0080] The crude comparative compound obtained in Comparative Example 2 and N-methyldiethanolamine were mixed evenly at a mass ratio of 1:3, and water was added to prepare an aqueous solution to obtain the comparative composition. The mass of the comparative composition was 100%, and the total content of the crude comparative compound and N-methyldiethanolamine prepared in Comparative Example 2 in the comparative composition was 50 wt%.

[0081] Experimental Evaluation

[0082] 1. Evaluation of the desulfurization performance of compounds and compositions

[0083] 1) Desulfurization rate determination:

[0084] The crude compounds prepared in Examples 1 to 9 were mixed with water to obtain desulfurizing agents 1 to 9 in sequence; the mass of any one of the desulfurizing agents 1 to 9 was taken as 100%, and the mass fraction of the corresponding crude compound in each desulfurizing agent was 50 wt%.

[0085] The crude comparative compound prepared in Comparative Example 2 was mixed with water to obtain desulfurizing agent 10; the mass of desulfurizing agent 10 was 100%, of which the mass fraction of the crude comparative compound was 50 wt%.

[0086] The compositions prepared in Examples 10 to 18, and the comparative compositions prepared in Comparative Examples 1 and 3, were desulfurizing agents 11 to 21, respectively.

[0087] The desulfurization rates of desulfurizing agents 1 to 21 were measured at 298 K, and the specific test methods were as follows:

[0088] i. Hydrogen sulfide gas is prepared by ferrous sulfide and dilute sulfuric acid. The prepared hydrogen sulfide gas is blown into a round-bottom flask pre-filled with desulfurizing agent through a high-pressure nitrogen cylinder. The molar ratio of hydrogen sulfide to desulfurizing agent is 10:1.

[0089] ii. The hydrogen sulfide content in the desulfurizing agent was determined by iodometric titration, and the desulfurization rate was calculated accordingly.

[0090] 2) Selectivity determination:

[0091] Hydrogen sulfide gas and carbon dioxide gas (molar ratio of hydrogen sulfide to carbon dioxide is 1:10) are simultaneously blown into a round-bottom flask pre-filled with desulfurizing agent. The molar flow rates of hydrogen sulfide gas and carbon dioxide gas in the mixed gas before being blown into the round-bottom flask and after being desulfurized by the desulfurizing agent are measured. The selective absorption coefficient is the value of (molar flow rate of hydrogen sulfide gas before absorption / molar flow rate of hydrogen sulfide gas after absorption) / (molar flow rate of carbon dioxide gas before absorption / molar flow rate of carbon dioxide gas after absorption).

[0092] Table 1. Desulfurization rate and selectivity of compounds and compositions

[0093] Serial Number Desulfurizer number Desulfurization rate at 298K / % Selective absorption coefficient Example 1 1 95.10 8.13 Example 2 2 97.40 8.04 Example 3 3 98.90 8.55 Example 4 4 99.85 8.77 Example 5 5 93.90 7.92 Example 6 6 94.80 7.85 Example 7 7 97.10 8.37 Example 8 8 96.80 8.61 Example 9 9 95.60 8.29 Comparative Example 2 10 83.10 4.12 Example 10 11 99.87 8.83 Example 11 12 99.85 8.75 Example 12 13 99.90 8.53 Example 13 14 99.84 7.21 Example 14 15 99.87 7.35 Example 15 16 99.89 8.85 Example 16 17 94.10 6.31 Example 17 18 95.20 6.72 Example 18 19 93.70 6.07 Comparative Example 1 20 99.77 3.78 Comparative Example 3 21 79.60 1.79

[0094] As shown in Table 1, the 50 wt% aqueous solutions of the crude compounds prepared in Examples 1 to 9 (corresponding to desulfurizers 1 to 9 respectively) exhibited desulfurization rates of 93.9% to 99.85% and selective absorption coefficients of 7.85 to 8.77. The compositions prepared in Examples 10 to 18 (corresponding to desulfurizers 11 to 19 respectively) showed desulfurization rates of 93.7% to 99.9% and selective absorption coefficients of 6.07 to 8.85, demonstrating good desulfurization rates and selectivity for hydrogen sulfide. Comparative Example 2, due to the substitution of reactants, showed a desulfurization rate of only 83.10% and a selective absorption coefficient of 4.12 in its 50 wt% aqueous solution of the crude comparative compound (corresponding to desulfurizer 10), indicating significantly poorer desulfurization performance and selectivity for hydrogen sulfide. The comparative composition prepared in Comparative Example 1 (corresponding to desulfurizer 20, i.e., a 40 wt% N-methyldiethanolamine aqueous solution) achieved a desulfurization rate of 99.77%, but its selective absorption coefficient was only 3.78, indicating poor selectivity for hydrogen sulfide. The comparative composition prepared in Comparative Example 3 (corresponding to desulfurizer 21) showed a significantly lower desulfurization rate of only 79.6%, with a selective absorption coefficient of only 1.79, also exhibiting poor selectivity for hydrogen sulfide.

[0095] While the present invention has been described with reference to specific embodiments, those skilled in the art will understand that various changes can be made without departing from the true spirit and scope of the invention. Furthermore, numerous modifications can be made to the subject, spirit, and scope of the invention to suit specific situations, materials, material compositions, and methods. All such modifications are included within the scope of the claims of the present invention.

Claims

1. The application of a composition in natural gas desulfurization, characterized in that, The composition comprises N-methyldiethanolamine and a compound having the structural formula shown in Formula I. Formula I; The method for preparing the compound includes the following steps: 1) React diisopropanolamine and ethylene glycol diglycidyl ether to obtain the reactants; 2) The reactants are distilled to obtain the compound; In step 1), diisopropanolamine and ethylene glycol diglycidyl ether are mixed with the first solvent and then reacted; In step 1), the reaction temperature is 80 to 120°C; the reaction time is 4 to 8 hours. In step 2), the distillation product is collected after distillation to obtain the compound; the distillation is vacuum distillation; the temperature of the vacuum distillation is 50 to 80°C. The mass ratio of the compound to N-methyldiethanolamine is (1 to 2):(2 to 3); The composition further includes a second solvent; the second solvent is water; the total mass of the composition is 100%, and the total mass of the compound and the N-methyldiethanolamine accounts for 20 wt% or 60 wt% of the composition.

2. The application according to claim 1, characterized in that, The molar ratio of diisopropanolamine to ethylene glycol diglycidyl ether is (2 to 3):(1 to 2).

3. The application according to claim 1, characterized in that, The total mass of the diisopropanolamine, ethylene glycol diglycidyl ether, and the first solvent is 100%, and the amount of the first solvent is 60 wt% to 80 wt%.

4. The application according to claim 1, characterized in that, The first solvent is selected from at least one of water, methanol, and ethanol.

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