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Phosphinate
Phosphinate
Phosphinate
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Phosphinate
Sodium hypophosphite
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/H3O2P/c1-3-2/h3H2,(H,1,2)/p-1
    Key: ACVYVLVWPXVTIT-UHFFFAOYSA-M
  • [O-][PH2]=O
Properties
H2O2P−
Molar mass 64.988 g·mol−1
Related compounds
Related compounds
 phosphite; phosphine oxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Phosphinates or hypophosphites are a class of phosphorus compounds conceptually based on the structure of hypophosphorous acid. IUPAC prefers the term phosphinate in all cases, however in practice hypophosphite is usually used to describe inorganic species (e.g. sodium hypophosphite), while phosphinate typically refers to organophosphorus species.

Hypophosphites

[edit]

The hypophosphite ion is (H
2PO
2)−
. The salts are prepared by heating white phosphorus in warm aqueous alkali e.g. Ca(OH)2:[1]

P4 + 2 Ca(OH)2 + 4 H2O → 2 Ca(H2PO2)2 + 2 H2

Hypophosphites are reducing agents:[1]

(H
2PO
2)−
 + 3 OH− → (HPO
3)2−
 + 2 H2O + 2 e−

Hypophosphites are used in electroless nickel plating as the reducing agent to deposit for example Ni metal from Ni salts.[1] The hypophosphite ion is thermodynamically unstable, and disproportionates on heating to phosphine and phosphate salts:

2 H
2PO
2−
 → PH3 + HPO
42−

Uses

[edit]

Hypophosphite (usually sodium hypophosphite) acts as a reducing agent to deposit nickel onto surfaces without using electricity. Common in electronics, automotive, and aerospace industries for corrosion resistance and hardness. Some hypophosphite compounds are used in medicines, particularly as sources of phosphorus or as stabilizers in formulations.

In polymer and plastic stabilization, they are used today as antioxidants and thermal stabilizers to prevent degradation during the processing of plastics like PVC. Beyond nickel plating, hypophosphites are used in general chemical synthesis where a mild reducing agent is needed.

Additionally, in wood science, sodium hypophosphite in combination with other agents, such as ammonium-, nitrogen- or aluminium-containing chemicals, has been used for in solid wood and particleboard to improve the fire retarding properties.[2][3]

See also

[edit]

References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Phosphinate

View on Grokipedia
from Grokipedia
Phosphinates are a class of organophosphorus compounds defined by a central pentavalent phosphorus atom bonded to two oxygen atoms—one via a double bond and the other as part of a hydroxy or alkoxy group—with two additional substituents (R¹ and R²) that may be hydrogen atoms or carbon-based groups, yielding the general formula R¹R²P(O)OH for the acids, R¹R²P(O)O⁻ for the anions, or R¹R²P(O)OR³ for the esters (where R³ is typically an alkyl or aryl group). Unlike phosphonates, which feature one C–P bond and three oxygen substituents on phosphorus, phosphinates incorporate two C–P bonds, one C–P bond and one P–H bond, or two P–H bonds, conferring distinct reactivity profiles such as enhanced reducing capabilities when a P–H bond is present. These compounds are notable for their , particularly due to robust P–C bonds in organic derivatives, which resist and metabolic degradation better than P–O bonds in phosphates. In the inorganic case, where R¹ = R² = H, phosphinates correspond to the hypophosphite ion (H₂PO₂⁻), a monovalent oxoanion formed by of phosphinic ( (H₃PO₂), which exhibits a tetrahedral geometry around with approximate C2v . Phosphinates have broad applications across chemistry and industry; for instance, the hypophosphite ion serves as a in electroless metal deposition processes, enabling the catalytic plating of and other metals on non-conductive surfaces without electricity. Organic phosphinates are employed in the synthesis of pharmaceuticals like the fosinopril, herbicides such as phosphinothricin (a inhibitor), and flame-retardant materials, while also acting as ligands in metal complexes due to their versatile coordination modes (monodentate, bidentate, or bridging). Their development has provided safer alternatives to toxic reagents like in organophosphorus manufacturing, highlighting their growing importance in sustainable synthesis.

Definition and Nomenclature

Chemical Structure

Phosphinic acids are organophosphorus compounds characterized by the general formula \ceR2P(O)OH\ce{R2P(O)OH}, where the substituents R can be atoms, alkyl groups, or aryl groups. This structure features a central phosphorus atom bonded to two R groups, a hydroxyl group (-OH), and an oxo group (=O). When R are alkyl or aryl groups (organic phosphinates), phosphorus is in a formal +3 , typical of P(III) oxyacids. When both R are (inorganic phosphinate or ), the oxidation state is +1. The corresponding phosphinate anion, \ceR2PO2−\ce{R2PO2^-}, results from deprotonation of the acidic hydroxyl group. In this ion, the phosphorus oxidation state is +3 for organic derivatives (R = alkyl/aryl) and +1 for the inorganic hypophosphite (R = H), adopting a tetrahedral geometry around the central atom, with bond angles approaching the ideal 109.5° due to the sp³ hybridization. The bonding consists of two single P-R bonds, a P=O double bond (approximately 1.48 Å in length), and a P-O⁻ single bond (about 1.51 Å), satisfying the octet rule on phosphorus through these four attachments. A specific example is , represented as \ceH2P(O)OH\ce{H2P(O)OH} or \ceH3PO2\ce{H3PO2}, where both R groups are , resulting in two distinctive P-H bonds (length ≈1.44 each). This compound exhibits the same tetrahedral at but with a +1 for P due to the two direct P-H linkages, distinguishing it from higher-substituted phosphinates. The depicts the connected to two via single bonds, a to oxygen, and a single bond to the OH group, with no lone pairs on . In comparison, phosphinates \ceR2PO2−\ce{R2PO2^-} differ structurally from phosphonates \ceRPO32−\ce{RPO3^{2-}}, which feature one R group, a P-C bond, and three P-O bonds in a tetrahedral setup with P at +3 , and from phosphates \cePO43−\ce{PO4^{3-}}, which lack any R or C-P bonds, have four equivalent P-O bonds (≈1.54 ), and in the +5 . These differences arise primarily from the number of carbon-phosphorus versus phosphorus-oxygen linkages, influencing reactivity and coordination behavior.

Naming Conventions

According to IUPAC recommendations, the term "phosphinate" designates the anions of the general formula R₂PO₂⁻ and their corresponding salts, where R can be or an organic , derived from phosphinic acids (R₂P(O)OH). This systematic nomenclature applies to both inorganic and organic variants, emphasizing the phosphorus-oxygen framework and substituent groups. For instance, dialkylphosphinates such as dimethylphosphinate ((CH₃)₂PO₂⁻) follow this convention, with the alkyl groups specified as prefixes. The common name "hypophosphite," however, is traditionally reserved for the specific inorganic anion H₂PO₂⁻ and its salts, a distinction rooted in the early 19th-century isolation and characterization of these compounds around –1820. This terminology highlights the reduced of compared to phosphite or ions, reflecting historical efforts to classify oxoacids based on their preparative origins and reactivity. Examples illustrate the naming differences: the inorganic salt NaH₂PO₂ is systematically termed sodium phosphinate but commonly known as . In organic contexts, the name adheres strictly to phosphinate, as seen in diphenylphosphinate ((C₆H₅)₂PO₂Na), where the aryl substituents replace hydrogen without invoking the "hypo" prefix. This dual system ensures clarity between the parent inorganic structure and its substituted derivatives.

Synthesis

Preparation of Hypophosphites

Hypophosphites are primarily synthesized through the alkaline of white , a process that involves the of elemental in the presence of a base to form the hypophosphite , H₂PO₂⁻. The standard laboratory method utilizes white (P₄) reacted with in water, proceeding as follows: P4+2 Ca(OH)2+4 H2O→2 Ca(H2PO2)2+2 H2\mathrm{P_4 + 2\ Ca(OH)_2 + 4\ H_2O \rightarrow 2\ Ca(H_2PO_2)_2 + 2\ H_2} This reaction produces calcium hypophosphite, which can then be converted to (H₃PO₂) by acidification with a strong such as , yielding the free alongside a calcium salt byproduct. On an industrial scale, the synthesis employs alkaline of in stirred reactors maintained at temperatures between 80–100°C to optimize reaction kinetics and minimize side products like . This setup facilitates the direct formation of when or a mixture of and is used as the base, allowing for efficient scaling with controlled . Purification of the resulting hypophosphite salts, particularly (NaH₂PO₂·H₂O), is achieved through from aqueous solutions, which separates the product from impurities such as phosphites and unreacted compounds. Yields for these processes typically range from 70–90% based on the input, with higher efficiencies attainable through optimized reaction conditions and of byproducts. Alternative methods include the electrochemical reduction of (H₃PO₃) on electrodes like in acidic media, providing a route for targeted synthesis under milder conditions.

Synthesis of Organic Phosphinates

Organic phosphinates, represented by the general formula R₂PO₂⁻ where R denotes an organic group such as alkyl or aryl, are synthesized primarily through methods that introduce or adjust the phosphorus-oxygen framework using carbon-substituted precursors. A key route involves the oxidation of secondary phosphines. Secondary phosphines (R₂PH) are converted to secondary phosphine oxides (R₂P(O)H) via mild oxidation with agents like or atmospheric oxygen. For instance, treatment with 30% H₂O₂ in at yields the phosphine oxide in 80-95% efficiency, depending on the substituents. The P-H bond in the resulting R₂P(O)H is then deprotonated using a strong base such as or butyllithium to generate the phosphinate anion R₂PO₂⁻. This two-step process is favored for its simplicity and high selectivity toward the desired . Hydrolysis of phosphinyl chlorides provides another direct pathway. Phosphinyl chlorides (R₂P(O)Cl), often prepared from phosphine oxides and , undergo with to form phosphinic acids (R₂P(O)OH) and HCl gas. The reaction is typically conducted in aqueous dioxane or acetone at 0-25°C with a base like triethylamine to scavenge HCl and drive completion, affording yields above 90% for alkyl-substituted derivatives. Subsequent of the acid with hydroxides yields the corresponding salt. This method is particularly useful for introducing diverse R groups via prior chloride synthesis. As a representative example, dibutylphosphinate is obtained by treating dibutylphosphine with aqueous at 50°C, promoting and exchange to form the sodium salt (Bu₂PO₂Na) in over 85% yield after acidification and basification steps. This approach leverages the acidity of the P-H proton in the oxide precursor. Synthesis challenges center on preventing over-oxidation, where excess oxidant or harsh conditions can convert intermediates to phosphonates (RP(O)(OH)₂) by unintended C-H or P-C cleavage. This is mitigated by employing stoichiometric oxidants, low temperatures ( to 50°C), and inert atmospheres like to limit oxygen exposure, ensuring >95% selectivity for phosphine s in many cases.

Properties

Physical Characteristics

Hypophosphites, the inorganic subclass of phosphinates where both substituents on phosphorus are hydrogen, are characteristically white, hygroscopic solids highly soluble in water. Sodium hypophosphite, the most common example, appears as a colorless to white crystalline powder or chunks and is readily deliquescent in moist air. Its monohydrate form has a reported density of approximately 0.8 g/cm³, while anhydrous material exhibits a higher density of 1.77 g/cm³ at 20°C. The compound is exceptionally water-soluble, with solubilities exceeding 100 g per 100 mL at room temperature (e.g., 909 g/L at 30°C), but it shows limited solubility in organic solvents like ethanol or acetone. Aqueous solutions of sodium hypophosphite, often used at concentrations around 50 wt%, have densities near 1.2 g/cm³. Thermally, hypophosphites lack a distinct melting point; the monohydrate dehydrates around 90°C, and the material decomposes above 200–310°C, releasing phosphine gas and forming phosphite or phosphate residues. Organic phosphinates, featuring at least one carbon-based substituent (R in R₂PO₂⁻), typically present as colorless oils, viscous liquids, or crystalline solids, depending on the nature and size of the R groups. These compounds generally exhibit low solubility in water (often <1 g/100 mL) due to their hydrophobic organic moieties but are highly soluble in polar organic solvents such as ethanol, acetone, or dichloromethane. For instance, phenylphosphinic acid (C₆H₅(H)PO₂H) is a white solid with a melting point of 83–85°C and limited water solubility, dissolving readily in alkaline aqueous solutions or alcohols. Larger derivatives like diphenylphosphinic acid ((C₆H₅)₂PO₂H) are also solids, melting at 193–195°C, with similarly low aqueous solubility but good compatibility with organic media. Organic phosphinates demonstrate greater thermal stability than hypophosphites, often remaining intact up to 300°C before decomposition, which is advantageous in high-temperature applications. Spectroscopic of phosphinates reveals consistent features reflective of their P(V) and bonding. In ³¹P NMR , free phosphinic acids (R₂PO₂H) display chemical shifts in the range of 30–50 ppm (relative to 85% H₃PO₄ at 0 ppm), with values shifting slightly upfield for salts or upon coordination. (IR) spectra exhibit a characteristic strong absorption band for the P=O stretch between 1150 and 1200 cm⁻¹, often accompanied by P–O–H deformations around 900–1000 cm⁻¹ in acidic forms. These signatures aid in structural confirmation and differentiation from related oxyacids like phosphonates (P–OH stretches near 1000–1100 cm⁻¹).

Chemical Reactivity

Hypophosphites exhibit strong reducing properties attributed to the presence of the P-H bond, which facilitates donation in reactions. Hypophosphorous acid undergoes thermal , particularly above 110 °C, according to the reaction: 3H3PO2→2H3PO3+PH33 \mathrm{H_3PO_2} \rightarrow 2 \mathrm{H_3PO_3} + \mathrm{PH_3} This process involves to and reduction to . Similarly, hypophosphite salts decompose upon heating to and higher phosphorus compounds such as phosphites and phosphates. Oxidation of typically proceeds stepwise, involving the cleavage of the P-H bond to form , as represented by: H3PO2+[O]→H3PO3\mathrm{H_3PO_2} + [\mathrm{O}] \rightarrow \mathrm{H_3PO_3} where [O] denotes an ; further oxidation yields . This reactivity is well-documented in kinetic studies with various oxidants. In coordination chemistry, phosphinate ligands coordinate to metal centers primarily through their oxygen atoms, often forming stable chelate complexes with transition metals. For instance, (2,2,2-trifluoroethyl)phosphinate forms mononuclear complexes with divalent late transition metals such as Co²⁺ and Zn²⁺ via O-bound interactions. Hypophosphorous acid behaves as a weak monobasic , with a pKa of approximately 1.2, corresponding to the dissociation of the P-OH proton; the P-H bond does not contribute to acidity. This property, combined with the high aqueous solubility of hypophosphites, enables these reactions to occur effectively in aqueous media.

Specific Compounds

Inorganic Hypophosphites

, with the NaH₂PO₂, represents the most prevalent inorganic hypophosphite compound and is commonly employed in its monohydrate form, NaH₂PO₂·H₂O, due to the variant's hygroscopic nature. This salt is synthesized through the neutralization of (H₃PO₂) with (NaOH), yielding the desired product alongside . The monohydrate exhibits a of 1.77 g/cm³ at 20°C and appears as white, odorless crystals that are highly soluble in (up to 909 g/L at 30°C). Commercial preparations of sodium hypophosphite typically meet purity standards with an assay range of 98-102%, ensuring suitability for industrial and analytical applications. Calcium hypophosphite, formulated as Ca(H₂PO₂)₂, serves as a key intermediate in the synthesis of various hypophosphites and other compounds, often obtained via metathesis reactions involving and calcium salts. It is characterized by lower compared to its sodium counterpart—approximately 16.7 g per 100 g of at —and is utilized in dietary supplements for its content. This white crystalline powder provides a stable source of the hypophosphite anion in formulations requiring reduced . Other notable inorganic hypophosphites include potassium hypophosphite (KH₂PO₂) and ammonium hypophosphite ((NH₄)H₂PO₂), both of which form white, deliquescent solids soluble in and alcohol. These salts share similar reducing properties with their sodium analog. Thermal decomposition of begins around 310°C via , producing (PH₃), (H₂), and various phosphorus oxides like sodium phosphite, hypophosphate, and ultimately tripolyphosphate in multi-step processes. A simplified reaction is 2 NaH₂PO₂ → PH₃ + Na₂HPO₄.

Organophosphinates

Organophosphinates are a class of organic compounds featuring the , where at least one in phosphinic acid is substituted by an alkyl, aryl, or other carbon-containing group, resulting in structures such as R₁R₂P(O)OH or R₁HP(O)OH. These compounds are distinguished by their carbon-phosphorus bonds, which confer greater compared to hypophosphites, particularly resistance to under acidic or basic conditions due to the robust P-C linkage that prevents facile cleavage by phosphatases or nucleophiles. In ³¹P NMR , organophosphinates exhibit characteristic chemical shifts around 40 ppm, reflecting the electronic environment of the atom influenced by the substituents and hydrogen bonding. A prominent alkyl example is dimethylphosphinic acid, (CH3)2P(O)OH(CH_3)_2P(O)OH, which undergoes upon heating and is employed as an extractant for metal ions in hydrometallurgical applications, leveraging its ability to form stable complexes with transition metals. Aryl derivatives include phenylphosphinic acid, C6H5HP(O)OHC_6H_5HP(O)OH, which melts at 83°C and is synthesized via oxidation of phenylphosphine, often using or air as the oxidant to selectively introduce the P=O bond while retaining the P-H functionality. Compounds with mixed substituents, such as methylphenylphosphinic acid, (CH3)(C6H5)P(O)OH(CH_3)(C_6H_5)P(O)OH, demonstrate solubility in alcohols like , facilitating their use in and facilitating crystallization from alcoholic solvents. In commercial contexts, dialkylphosphinic acids, including nonsymmetric variants like those derived from mixed alkyl chains, are key reagents in for the selective extraction and separation of heavy rare earth elements from ores, owing to their tunable and high selectivity for metal coordination. General synthesis of organophosphinates often involves oxidation of the corresponding secondary or primary phosphines with oxidants like .

Applications

Industrial Processes

One of the primary industrial applications of phosphinates, particularly , is in electroless nickel plating, a chemical deposition process that coats substrates with a - alloy without the need for an external . In this autocatalytic reaction, serves as the , facilitating the reduction of nickel ions from the bath solution onto the surface, typically following the simplified : Ni2++H2PO2−+H2O→Ni+H2PO3−+2H+\text{Ni}^{2+} + \text{H}_2\text{PO}_2^- + \text{H}_2\text{O} \rightarrow \text{Ni} + \text{H}_2\text{PO}_3^- + 2\text{H}^+ This process, developed in the 1940s by Abner Brenner and Grace Riddell, produces deposits containing 5-15% phosphorus by weight, which enhances corrosion resistance and hardness. Electroless nickel plating baths are maintained under specific conditions to optimize deposition rates and alloy composition, including a pH of 4-5, temperatures of 80-95°C, and sodium hypophosphite concentrations of 20-30 g/L. These parameters ensure stable plating rates of approximately 10-20 μm per hour while minimizing bath decomposition. The resulting coatings are widely used in the automotive industry for components such as fuel injectors, valves, and piston rings, where uniform coverage on complex geometries and non-conductive surfaces provides superior wear resistance and protection against harsh environments. A key advantage of this process is the ability to achieve uniform thickness across intricate parts, including blind holes and irregular shapes, which is challenging with electrolytic methods. Global production of for the industry supports this demand, with capacities exceeding 20,000 tons annually in major markets like alone. In addition to , hypophosphites find use in treatment as oxygen scavengers, where reacts with dissolved oxygen to prevent of metal surfaces in high-temperature systems. This application leverages the compound's reducing properties to maintain low oxygen levels, typically below 5 ppb, thereby extending equipment life in industrial steam generation.

Material Science and Other Uses

Organophosphinates function as effective additives in matrices, particularly serving as antioxidants and stabilizers in (PVC) formulations. Alkylphosphinates, for instance, contribute to preventing dehydrochlorination during by decomposing hydroperoxides into non-radical products, thereby enhancing stability and extending the material's under oxidative conditions. These compounds are often combined with primary phenolic antioxidants to synergistically protect PVC from degradation, maintaining transparency and color integrity in applications like flexible films and cables. In fire retardancy, hypophosphites such as and ammonium hypophosphite are integrated with nitrogen-containing compounds to treat wood, forming systems that promote char formation and reduce flammability. For example, modification of Scots pine sapwood with and yields a durable that limits release and production during combustion, achieving a 41% reduction in peak heat release rates compared to untreated wood. Ammonium hypophosphite, when combined with expandable graphite in polyurethane foams or applied in wood-polymer composites, enhances and suppresses spread through phosphorus-nitrogen , making it suitable for structural wood treatments in building materials. Phosphinate ligands play a key role in , particularly in complexes for reactions. Rhodium-phosphinate catalysts enable the of enol phosphinates, converting di- and trisubstituted substrates into chiral alkyl phosphinates with high enantioselectivity (up to 99% ), which is valuable for synthesizing optically active intermediates. These ligands provide steric and electronic tuning that stabilizes the metal center, facilitating efficient H2 activation and substrate binding in processes like the reduction of α,β-unsaturated phosphinates. Beyond these areas, phosphinates serve as pharmaceutical intermediates, where phosphinic pseudopeptides act as potent inhibitors of matrix metalloproteinases by mimicking transition-state structures in active sites. Single-point modifications to these phosphinates improve binding affinity and selectivity, supporting for conditions like cancer and . Recent developments highlight bio-based phosphinates for sustainable plastics, with 2023 studies demonstrating their efficacy as halogen-free flame retardants in . Aluminum diethylphosphinate, derived from renewable feedstocks, achieves V-0 UL-94 ratings in bio-based composites while reducing environmental impact through lower lifecycle emissions compared to brominated alternatives. Radiation crosslinking of phosphinate-treated, wood-filled bio- further enhances fire retardancy, promoting char formation and mechanical integrity for eco-friendly plastics.

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