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Diethylphosphonoacetic acid, as an important organic synthesis reagent, is a transparent, colorless to light yellow viscous liquid. The molecular formula C6H13O5P, CAS 3095-95-2, has a boiling point of approximately 315.9 ° C. Under reduced pressure conditions (such as 0.05 mmHg), its boiling point significantly decreases to around 150 ° C, with a density of approximately 1.220 g/mL (measured at 25 ° C).
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Chemical Formula |
C6H13O5P |
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Exact Mass |
196 |
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Molecular Weight |
196 |
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m/z |
196 (100.0%), 197 (6.5%), 198 (1.0%) |
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Elemental Analysis |
C, 36.74; H, 6.68; O, 40.78; P, 15.79 |
For example, its vapor pressure is relatively low, about 9.07E-05 mmHg at 25 ° C. This low vapor pressure means that the product is not easily volatile at room temperature, which is beneficial for its long-term storage and transportation. In addition, it also has a certain solubility and can dissolve in some common organic solvents such as ethanol, acetone, etc., providing convenience for its application in organic synthesis. For example, its vapor pressure is relatively low, about 9.07E-05 mmHg at 25 ° C. This low vapor pressure means that it is not easily volatile at room temperature, which is beneficial for long-term storage and transportation. In addition, it also has a certain solubility and can dissolve in some common organic solvents such as ethanol, acetone, etc., providing convenience for its application in organic synthesis.
The application of Diethylphosphonoacetic acid in the field of resin synthesis is of significant importance, and its unique chemical properties make it play a crucial role in the preparation and modification of various synthetic resins.
Plasticizers
Plasticizers are an indispensable and important component in the preparation process of synthetic resins. The product, as an efficient plasticizer, has shown good application effects in the preparation of synthetic resins such as polyvinyl chloride (PVC) and polystyrene (PS).
Improving softness and ductility
The product can effectively reduce the glass transition temperature of synthetic resins, allowing them to exhibit good softness and ductility at lower temperatures. This feature makes synthetic resins with added diethyl phosphoacetic acid easier to process and shape during the manufacturing process, such as bending and stretching, without causing brittleness or damage, thus improving the adaptability of resin processing.
Improving processing performance
The addition of diethyl phosphoacetic acid can significantly reduce the viscosity of the synthesized resin, improve its fluidity and processing performance. This allows the resin to be more evenly distributed in the mold during processing such as extrusion and injection molding, reducing waste and defect rates during the production process and further improving the efficiency of industrial production.
Improving durability
The product also has good weather resistance and stability, which can significantly improve the service life and durability of synthetic resins. The synthetic resin with added diethyl phosphoacetic acid is not prone to aging, discoloration, and cracking during long-term outdoor use under natural conditions, stably maintaining its good appearance and basic performance.
Suppression of flame spread
The product can quickly decompose during resin combustion to produce flame retardant substances such as phosphoric acid. These substances can quickly cover the surface of the resin to form a dense protective layer, effectively isolating oxygen and heat, thereby effectively suppressing the spread and diffusion of flames and reducing fire hazards.
Improving flame retardancy
By adding an appropriate amount of diethyl phosphoacetic acid, the flame retardancy of synthetic resins can be significantly improved to meet higher safety standards. This is of great significance for manufacturing products such as wires and cables, building materials, etc. that require high flame retardant performance, effectively ensuring the safety of use in various scenarios.
Reducing toxic gas emissions
Compared with traditional halogenated flame retardants, diethyl phosphoacetic acid produces fewer toxic gases during combustion and has a smaller impact on the environment and human health. This environmental protection advantage makes it have a wider application prospect in the field of flame retardants, adapting to the current green development trend.
Improving wettability and dispersibility
The product can reduce the surface tension of synthetic resins, making them easier to wet and disperse in solvents or media. This is of great significance for the preparation of high-quality coatings, inks and other products, ensuring the uniformity of the product and improving its use effect.
Granting special functions
By adding diethyl phosphoacetic acid, synthetic resins can also be endowed with some special functions, such as anti-static, antibacterial, anti fog, etc. These functionalized synthetic resins have broad application prospects in fields such as electronics, medicine, and automobiles, better meeting the diversified use needs of different industries.
Other applications
In addition to the above applications, diethyl phosphoacetic acid has other applications in the field of resin synthesis. For example, it can be used as a crosslinking agent to form a cross-linked structure by reacting with active groups in the resin, effectively improving the strength and hardness of the resin. In addition, diethyl phosphoacetic acid can also be used as an antioxidant, light stabilizer, and other additives to further improve the stability and durability of synthetic resins.
Diethylphosphonoacetic acid is a phosphorus containing organic compound commonly used in organic synthesis and pesticide industry. This compound can be directly synthesized by selectively oxidizing phosphorus and reacting with certain aldehydes or ketones. The following are detailed reaction steps and corresponding chemical equations.
1.1 Reagent preparation
-Triethyl phosphorus: This is the main source of phosphorus in the reaction.
-Aldehydes or ketones: Commonly used include acetaldehyde (CH3CHO) or acetone (CH3COCH3).
-Oxidants: Generally, hydrogen peroxide (H2O2) or other mild oxidants are used.
-Solvents: Anhydrous toluene, dimethyl sulfoxide (DMSO), etc. can be used.
1.2 Reaction equipment
-Reaction bottle: usually uses corrosion-resistant glassware.
-Magnetic stirrer: used to ensure uniform mixing of reactions.
-Condenser: to prevent volatilization and loss of reactants.
2.1 Preparation of reaction system
(1). Add an appropriate amount of anhydrous toluene as the solvent in a dry reaction bottle.
(2). Add triethyl phosphorus to ensure complete dissolution.
2.2 Adding Aldehydes or Ketones
(1). Slowly add acetaldehyde or acetone, pay attention to controlling the addition speed to avoid violent reactions.
(2). Stir the mixture to make it evenly dispersed.
2.3 Oxidation reaction
(1). Slowly add hydrogen peroxide solution while maintaining stirring.
(2). Control the reaction temperature at room temperature or slightly above room temperature (25-35 ° C) to avoid hydrogen peroxide decomposition failure.
(3). Continue stirring the reaction system, usually requiring several hours of reaction.
3.1 Reaction mechanism
This reaction involves the addition of triethylphosphorus and aldehydes/ketones, as well as subsequent oxidation steps. The specific reaction equation is as follows:
a. Reaction of triethylphosphorus with acetaldehyde:
(C2H5)3P+CH3CHO → (C2H5)3P-CH (OH)CH3
b. Reaction of triethylphosphorus with acetone:
(C2H5)3P+CH3COCH3 → (C2H5)3P-C (OH)(CH3) 2
c. Oxidation steps (using acetaldehyde as an example):
(C2H5)3P-CH(OH)CH3+H2O2 → (C2H5)2P(O)CH(OH)CH3+C2H5OH
(C2H5)2P(O)CH(OH)CH3 → (C2H5)2P(O)CH=CH2+H2O
d. Final product formation (using acetaldehyde as an example):
(C2H5)2P(O)CH=CH2+O2 → (C2H5)2P(O)CH2COOH
4.1 Extraction
After the reaction is completed, pour the reaction mixture into a separating funnel.
2. Wash the reaction mixture multiple times with distilled water and organic solvents to remove inorganic impurities and unreacted oxidants.
4.2 Solvent distillation
1. Use a rotary evaporator to remove organic solvents.
2. Further purify the remaining substances.
4.3 Purification method
1. Recrystallization: Select a suitable solvent for recrystallization based on the solubility of the product.
2. Column chromatography: Further separation and purification of the target product through column chromatography.
5.1 Nuclear Magnetic Resonance (NMR)
Confirm the structure of the product using nuclear magnetic resonance hydrogen spectroscopy (NMR) and phosphorus spectroscopy (NMR).
5.2 Infrared spectroscopy (IR)
Confirm the characteristic absorption peaks of the carbonyl and phosphorus oxygen bonds of the product through infrared spectroscopy analysis.
5.3 Mass spectrometry (MS)
Determine molecular weight and structure using mass spectrometry analysis.
Gradual hydrolysis and calcium ion chelation of The Product under acidic conditions
Diethylphosphonoacetic acid (DPA, CAS number 3095-95-2), as a phosphorus containing organic acid, exhibits unique advantages in metal ion chelation, asymmetric synthesis, and biosensing due to its dual functional groups of phosphoryl (- PO (OEt) ₂) and carboxyl (- COOH) in its molecular structure. In industrial water treatment, paper bleaching, textile printing and dyeing, DPA needs to efficiently chelate with calcium ions (Ca ² ⁺) under acidic conditions (pH 2-6) to prevent equipment scaling or improve process efficiency.
The molecular structure of DPA and its adaptability to acidic environments
Molecular Structure Characteristics and Electronic Distribution
The molecular formula of DPA is C ₆ H ₁ ∝ O ₅ P, and its core structure is composed of a phosphoacetic acid skeleton:
Phosphoryl group (- PO (OEt) ₂): The phosphorus atom adopts sp ³ hybridization to form a tetrahedral configuration, and two ethoxy groups (- OEt) provide electron cloud density, making the phosphorus partially positively charged (δ ⁺) and susceptible to nucleophilic attack.
Carboxyl group (- COOH): The strong electron withdrawing effect of carbonyl oxygen (O=C) makes carboxyl hydrogen (H) easily dissociated (pKa ≈ 3.48), and can still partially dissociate into - COO ⁻ under acidic conditions, providing chelating sites.
The Influence of Acidic Environment on Molecular Stability
The stability of DPA in acidic media with pH 2-6 is regulated by the following factors:
Protonation competition: There is competition between the protonation of carboxyl groups (- COOH ₂⁺) and the protonation of phosphoryl groups (- PO (OH) (OEt) ₂). Calculations show that at pH 3, the proportion of carboxyl protonation is about 15%, while the proportion of phosphoryl matrix protonation is less than 5%, indicating that carboxyl is the main reactive center under acidic conditions.
Hydrolysis sensitivity: The P-O bond of phosphoryl groups (bond energy of approximately 360 kJ/mol) is susceptible to attack by water molecules under acidic conditions, leading to gradual hydrolysis. Experimental data shows that in a pH 3 buffer solution, the half-life of DPA is approximately 12 hours, significantly shorter than under neutral conditions (pH 7, half-life>72 hours).
Gradual hydrolysis mechanism of DPA under acidic conditions
Under acidic conditions, the hydrolysis of DPA begins with the substitution of one ethoxy group (- OEt) of the phosphoryl group by a water molecule, resulting in the formation of monoethyl phosphonoacetic acid (MEPA):
Reaction kinetics: Calculated by density functional theory (DFT) at the B3LYP/6-311+G level, the activation energy (Δ G ‡) for this step is 102.3 kJ/mol, and the reaction rate constant k ₁ is approximately 1.2 × 10 ⁻⁴⁴⁻¹ at 25 ℃.
Solvation effect: Water molecules stabilize negative charges in transition states through hydrogen bonding, reducing activation energy. At pH 3, the concentration of H ⁺ (10 ⁻³ M) increases k ₁ to 2.8 × 10 ⁻⁴ s ⁻¹ through protonation of ethoxy oxygen atoms (enhancing their leaving ability).
MEPA is further hydrolyzed to produce phosphoacetic acid (PA):
Reaction energy barrier: DFT calculations show that the Δ G ‡ of the second step hydrolysis is 115.6 kJ/mol, which is higher than the first step (due to the need to simultaneously break two P-O bonds), resulting in a significantly lower k ₂ (approximately 3.5 × 10 ⁻⁵⁻¹ at 25 ℃) than k ₁.
PH dependence: At pH 2, the H ⁺ concentration (10 ⁻ ² M) protonates two ethoxy groups, increasing k ₂ to 1.2 × 10 ⁻⁴ s ⁻¹. However, at this point, the initial hydrolysis of DPA (k ₁) slows down due to competitive protonation, and the overall hydrolysis rate shows a nonlinear change.
PA is highly stable under acidic conditions, with pKa ₁=1.2 and pKa ₂=6.7 for its phosphoryl group (- PO ∝ H ₂), indicating that PA mainly exists in the form of - PO ∝ H ⁻ and - PO ∝ ² ⁻ within the pH range of 2-6, providing key sites for subsequent calcium ion chelation.
Module title
Diethylphosphonoacetic acid (CAS 3095-95-2), also known as (diethoxyphosphinyl)acetic acid, is an important organophosphorus compound with a carboxyl group and phosphonate structure. Its discovery and development are closely linked to the advancement of organophosphorus chemistry in the 20th century, with its synthesis and application research gradually deepening over decades.
In the mid-20th century, as organophosphorus compounds gained increasing attention in organic synthesis and material science, researchers began exploring phosphonate derivatives with dual functional groups. The product was first synthesized and identified in the late 1960s, initially as a by-product in the synthesis of triethyl phosphonoacetate, a key reagent in the Horner-Wadsworth-Emmons reaction.
Early synthesis methods were relatively cumbersome, with low yields and poor purity. It was not until the 1990s that researchers optimized the synthesis route, establishing a mature method using triethyl phosphonoacetate as the raw material, which undergoes hydrolysis under alkaline conditions and acid neutralization to obtain the target product with a yield of up to 100%. This optimization laid the foundation for its widespread research and application.
Since the late 1990s, its unique chemical properties have been gradually explored. Studies in 1996 revealed its role in synthesizing β-keto phosphonates, an important intermediate in organic synthesis. With the development of synthetic chemistry, it has been further applied as a nucleophile in nucleophilic addition reactions, expanding its application scope. Today, it is widely used in organic synthesis, material modification and other fields, its discovery history reflecting the continuous progress of organophosphorus compound research.
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