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List of Standard Specifications for Phosphonates
|Molecular Formula||Typically RPO3H2 where 'R' represents an alkyl or aryl group.||Identifies the phosphonate compound.|
|Structure||A phosphorus atom bonded to a carbon atom and three oxygen atoms. Two of these form -PO3H2 group.||The structure impacts the stability and potential applications of the phosphonate.|
|Melting Point||Varies depending on the specific phosphonate compound.||Determines the conditions under which phosphonates can be safely used and stored.|
|Boiling Point||Varies depending on the specific phosphonate compound.||Determines the conditions under which phosphonates can be safely used and stored.|
|Specific Gravity||Depends on the particular composition and structure of the phosphonate.||Helps in identifying the phosphonate and provides insights into its handling and transportation requirements.|
|Solubility in Water||Generally high.||Essential for their use as water treatment chemicals.|
|pH Value||Depends on the concentration of the phosphonate and the specific compound.||Affects the reactivity of the phosphonate and its suitability for various applications.|
|Heat of Vaporization||Specific to each phosphonate compound.||Influences its volatility and safety considerations in storage and use.|
|Flashpoint||Specific to each phosphonate compound.||Crucial for safety considerations in storage and use of phosphonates.|
|Vapor Pressure||Specific to each phosphonate compound.||Influences its volatility and safety considerations in storage and use.|
Please note that the specific values for these parameters can vary widely between different phosphonates due to their molecular structure and composition differences. Always refer to the Material Safety Data Sheet (MSDS) for information about a particular phosphonate compound.
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The Ultimate Guide to Phosphonates
Discover the ultimate guide to phosphonates – the essential resource for choosing the perfect type for your requirements. In this comprehensive guide, we will delve into the details of phosphonates, their suitability for various applications, and their many benefits. With this knowledge, you can confidently navigate the market and select the ideal phosphonate for your project. Empower yourself with the expertise to make an informed purchasing decision.
What are phosphonates?
Phosphonates are chemical compounds containing a phosphonate functional group (-PO3H2) attached to a carbon atom. They are widely used in various industrial applications due to their excellent chelating and sequestering properties.
Definition of Phosphonate
Phosphonates are organic compounds that contain a phosphonate functional group bonded to a carbon atom. These compounds are characterized by their metal-chelating solid ability, making them useful for many industrial applications.
There are several types of phosphonate compounds, including hydroxy ethylidene diphosphonate (HEDP), diethylenetriaminepenta(methylene phosphonic acid) (DTPMP), and ethylenediamine tetra (methylene phosphonic acid) (EDTMP). These compounds are used in various applications, such as water treatment, detergent, oilfield chemicals, and pharmaceuticals.
Synthesis of Phosphonates
Phosphonates are synthesized using different methods, such as the Michaelis-Arbuzov, Kabachnik-Fields, and Mannich reactions. These processes involve the reaction of phosphorus derivatives with other organic compounds to form phosphonate compounds.
Phosphonate analogs are used in various applications where phosphonate compounds are not suitable. These analogs include phosphates, carboxylic acids, and amino acids. These chemical compounds are structurally similar to phosphonates but have different properties that make them more appropriate for specific applications.
Phosphonate degradation is the process by which phosphonates break down in the environment. This process can occur naturally through biodegradation or chemical degradation using specific chemicals or enzymes. In industrial settings, it is essential to manage phosphonate degradation to prevent harmful environmental effects.
Industries That Use Phosphonates
Phosphonates are used in numerous industries, including water treatment, detergent and cleaning products, agriculture, oil and gas, and pharmaceuticals. In water treatment, phosphonates are used to prevent scale formation and corrosion. In detergent and cleaning products, they are used as builders to avoid the appearance of hard water spots. In agriculture, they are used as chelators and as a source of phosphorus. In oil and gas, they are used as corrosion inhibitors and as scale inhibitors. In pharmaceuticals, they are used as bone-resorption inhibitors and in radiopharmaceuticals.
Phosphonates are generally regarded as safe for use in industrial applications. However, exposure to high concentrations can harm human health and the environment. In aquatic environments, the accumulation of phosphonates can cause eutrophication, leading to the growth of toxic algae and oxygen depletion in water bodies. Therefore, appropriately handling, storing, and disposing of these compounds is essential to prevent potential safety concerns. Overall, understanding the properties and applications of phosphonates is essential in various industrial settings and requires proper management to minimize any possible safety risks.
What is the role of phosphonates in biochemistry?
Phosphonates are organic molecules that contain a phosphonic acid group (-PO3H2) as the primary functional group. They have a distinct structural composition compared to phosphates, as they have a carbon atom directly attached to the phosphorus atom instead of an oxygen atom. This chemical difference leads to different properties and functions in biological systems.
The Phosphonate Group in Biochemistry
Phosphonates can be found in many biological systems, including bacteria, fungi, plants, and animals. One of the most well-known phosphonate-containing compounds is fosfomycin, an antibiotic that inhibits bacterial cell wall biosynthesis. Another example is methyl phosphonate, produced by marine microorganisms and plays a role in the global phosphorus cycle.
Phosphonate esters are a type of organic compound that consists of a phosphonate group connected to an organic moiety through an oxygen atom. They are commonly used as synthetic intermediates in organic chemistry and have been shown to have biological activity, including antimicrobial, antiviral, and anticancer properties.
Phosphonate as a Substitute for Phosphate
Phosphonates can substitute for phosphates in biochemical processes such as enzyme catalysis and DNA repair. For example, the enzyme alkaline phosphatase can cleave phosphonate esters similarly to phosphates, indicating that they can serve as substrate analogs. In addition, some organisms can use phosphonates as a source of phosphorus instead of phosphates.
Phosphonate and Phosphonic Acid
Phosphonic acid is another organic phosphorus-containing compound with similar properties to phosphonates. Some people use the terms “phosphonate” and “phosphonic acid” interchangeably. However, they are different, as phosphonic acid contains a hydroxyl group (-OH) instead of an organic moiety connected to the phosphorus atom.
How are phosphonates used in water treatment?
Cooling Water Treatment
Cooling water systems are subject to various contaminants that can damage and corrode equipment. Phosphonates are widely used in cooling water treatment as they effectively prevent scale formation by controlling the precipitation of mineral salts. By reducing scale, phosphonates also prevent corrosion and inhibit bacteria growth. Additionally, phosphonates are compatible with various chemical oxidants, pH levels, and temperatures, making them a practical solution for cooling water treatment.
Phosphonates for Inhibiting Bacterial Growth
One of the most critical aspects of water treatment is ensuring bacteria do not grow in the water supply. Bacteria such as Legionella and Pseudomonas can cause serious health issues, and their growth can be prevented by using phosphonates. Phosphonates disrupt the biofilm that bacteria require to grow, effectively starving them of nutrients. Moreover, phosphonates can penetrate the cell walls of bacteria, thus killing them.
Phosphonates as Corrosion Inhibitors
It is important to prevent corrosion to ensure that water treatment equipment such as pipes, tanks, and reservoirs last long. Corrosion can result in leaks, system failure, and contamination. Phosphonates are widely used as corrosion inhibitors in water treatment. They form a protective layer on metal surfaces, preventing them from reacting with environmental factors such as oxygen and water. This layer also helps to minimize the formation of other impurities in the water.
Phosphonates for Scale Prevention
Scale buildup in water treatment systems can be disastrous for equipment, leading to clogging, reduced efficiency, and system damage. Phosphonates are highly effective in preventing scale formation as they act as crystal growth inhibitors and can even dissolve existing scales. This helps to keep water in the system clean and straightforward while reducing the need for frequent cleaning and maintenance.
What are the uses of phosphonates in medicine?
Phosphonate prodrugs are a type of medication that is administered in an inactive form and then metabolized into an active state. This process often involves using a phosphonate group to modify the drug’s chemical structure. Researchers can improve its stability, solubility, and cell penetration by adding a phosphonate to a drug molecule. These modifications can enhance the drug’s bioavailability and therapeutic efficacy significantly. Examples of phosphonate prodrugs include Fosphenytoin, a medication used to treat seizures, and Tenofovir disoproxil fumarate, a drug used to treat HIV.
Antiviral phosphonates are a class of medication used to treat viral infections. This type of drug works by inhibiting the enzyme responsible for virus replication. The phosphonate group in these drugs is essential in the inhibition process. Some examples of antiviral phosphonates include Cidofovir, a medication used to treat cytomegalovirus (CMV), and Adefovir, used to treat hepatitis B.
Phosphonates for the Treatment of HIV
Researchers have identified several phosphonates that are effective in the treatment of HIV. These drugs are mostly phosphonate prodrugs, and they work by inhibiting the reverse transcriptase enzyme that HIV uses to replicate itself. One such drug is Tenofovir disoproxil fumarate, which is transformed into active form once it enters the cell. Another drug used to treat HIV, Etravirine, contains a phosphonate group that enhances its effectiveness.
Phosphonates for the Treatment of Chronic Hepatitis B
Phosphonates such as Adefovir, Entecavir, and Tenofovir disoproxil fumarate treat chronic hepatitis B. These drugs work by inhibiting the reverse transcriptase enzyme responsible for the virus’s replication. They are particularly effective in reducing viral load and delaying or preventing the progression to liver cirrhosis and hepatocellular carcinoma.
Approved Phosphonates for Medical Use
Over the years, several phosphonates have been approved for medical use. Some notable ones include Etidronate disodium, used to treat Paget’s disease and osteoporosis, and Pamidronate disodium, used to treat bone metastases. However, phosphonates can also have side effects, including fever, hypocalcemia, and renal failure. Therefore, patients need to consult with their healthcare provider before using any phosphonate medication.
In conclusion, phosphonates have found a unique place in modern medicine due to their peculiar chemical properties. From prodrugs that enhance bioavailability and efficacy to antiviral medications that inhibit virus replication, phosphonates have proven to be valuable tools in treating various medical conditions. Despite the side effects, the approved use of phosphonates in medicine provides hope for those suffering from chronic diseases.
What are the characteristics of phosphonate compounds?
Structural Features of Phosphonate Compounds
Phosphonate compounds have a tetrahedral geometry around the phosphorus atom, with three oxygen atoms in a trigonal planar configuration. The fourth bond of the phosphorus is usually attached to a carbon atom, resulting in a C-PO bond. The electronegativity of the phosphorus atom leads to an electron-deficient center, making it highly reactive toward nucleophiles such as amines, hydroxyl groups, and thiols. The presence of acidic protons in the phosphonate group facilitates hydrogen bonding and enables metal chelation.
Functional Groups in Phosphonates
Phosphonate compounds contain several functional groups, including phosphonate esters, phosphonate diesters, and phosphonate amides. Phosphonate esters are formed when the -OH group of alcohol reacts with the phosphorus of a phosphonate diester, resulting in ester formation. Phosphonate amides are formed when the -NH2 group of an amino acid reacts with the phosphorus of a phosphonate diester. Phosphonate diesters are used as leaving groups in synthesizing cyclic phosphonates, which are essential intermediates in the production of bioactive compounds.
Synthesis of Phosphonate Compounds
Phosphonates can be synthesized using various methods, such as the Michaelis-Arbuzov, Kabachnik-Fields, and Horner-Wadsworth-Emmons reactions. One of the most common methods is the Michaelis-Arbuzov reaction, where an alkyl halide reacts with a trialkyl phosphite in the presence of a metal catalyst. The Kabachnik-Fields reaction involves the reaction of an aldehyde or ketone with diethyl phosphite and an amine. In contrast, the Horner-Wadsworth-Emmons reaction employs the response of a phosphonate diester, an aldehyde or ketone, and a base.
Phosphonate Analogues as Enzyme Inhibitors
Phosphonate analogs have gained increasing significance as enzyme inhibitors due to their high affinity and specificity towards enzymes with phosphate esters in their active site. Many well-known drugs, such as bisphosphonates for bone disorders, herbicides, and fungicides, are phosphonate analogs. They can also inhibit enzymes such as HIV protease, phospholipases, and acetylcholine esterase, among others. As enzyme inhibitors, they play a crucial role in developing new drugs targeting various diseases.
Phosphonate Compounds as Amino Acid Esters
Phosphonate compounds have been widely used as amino acid esters in synthesizing peptides and other biomolecules. During peptide synthesis, the phosphonate ester group acts as a temporary protecting group for the amino group. The phosphonate ester can be cleaved off by mild acidic conditions, releasing the peptide chain. This method has synthesized various bioactive peptides, including antibiotics, neuropeptides, and hormones. Additionally, phosphonate amino acid esters have been used to synthesize glycopeptides, essential for developing vaccines and other therapeutic agents.
Frequently Asked Questions
A: The synthesis of phosphonates involves the reaction of a phosphorous compound with an acid, resulting in the formation of a phosphonate compound.
A: Phosphonates differ from phosphates in that they have a carbon atom bonded to the phosphorous atom, whereas phosphates have an oxygen atom bonded to the phosphorous atom.
A: Phosphonates have a variety of uses, including being used as inhibitors in various chemical reactions, as components of detergents and water treatment products, and as flame retardants.
A: Yes, some phosphonate compounds have been approved by the FDA for the treatment of certain medical conditions. For example, acyclic nucleoside phosphonates have been used for the treatment of hepatitis B and HIV infections.
A: Examples of phosphonate compounds used as drugs include acyclic nucleoside phosphonates as potent nucleotide analogues and prodrugs of PMEA, as well as alkoxyalkyl esters of cidofovir for the treatment of viral infections.
A: Phosphonates can work as drugs by inhibiting specific enzymes or receptors in pathogens, interfering with their metabolic pathways, or mimicking the structure of important molecules in the body.
A: Researchers are studying the potential applications of phosphonate compounds in various fields, such as medicine, agriculture, and materials science. They are investigating new synthesis methods, exploring their biological activities, and developing new drug candidates.