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Propanamide

Propanamide, also known as propionamide, is the IUPAC name for the primary amide derived from propanoic acid, with the molecular formula C₃H₇NO and structural formula CH₃CH₂C(O)NH₂.^[1] It features a polar amide functional group that enables hydrogen bonding. This compound, known since the early days of organic chemistry, appears as a white to off-white crystalline solid at room temperature, with a molecular weight of 73.09 g/mol.^[2] Propanamide is classified as harmful if swallowed and an eye irritant.^[1] Naturally occurring traces have been identified in the plant Bongardia chrysogonum.^[1]

Introduction and Nomenclature

Chemical Identity

Propanamide is the preferred IUPAC name for this organic compound, with other common names including propionamide.^[1]^[3] It is classified as a primary aliphatic amide, specifically a monocarboxylic acid amide obtained by the formal condensation of propanoic acid with ammonia.^[1] The molecular formula of propanamide is \ce{C3H7NO}, and its structural formula is \ce{CH3CH2C(O)NH2}.^[1]^[3] The molar mass is 73.09 g/mol.^[1] Key identifiers include the CAS Registry Number 79-05-0 and the IUPAC International Chemical Identifier (InChI) InChI=1S/C3H7NO/c1-2-3(4)5/h2H2,1H3,(H2,4,5).^[1]^[3]

Historical Background

The synthesis of simple aliphatic primary amides like propanamide emerged in the early 19th century amid broader advancements in organic chemistry. This approach paralleled the preparation of other primary amides from ammonium carboxylates and was influenced by foundational work on amide formation, including Friedrich Wöhler's groundbreaking 1828 synthesis of urea from ammonium cyanate, which demonstrated the feasibility of laboratory production of organic compounds previously thought exclusive to living organisms.^[4] Wöhler's achievement spurred investigations into related nitrogen-containing functionalities, establishing dehydration of ammonium salts as a standard route for simple amides. By the mid-19th century, propanamide gained recognition as a distinct compound in organic chemistry literature, often cited as a prototypical example of an aliphatic amide in texts exploring functional group behavior. Its simplicity made it a valuable model for studying amide properties without the complexities of aromatic or substituted variants, though specific milestones tied to its isolation remain sparse due to the routine nature of its preparation. Early empirical analyses focused on its composition, aligning with the era's emphasis on elemental determination in organic substances. The understanding of organic compounds like propanamide advanced significantly in the 1850s with the development of structural organic chemistry. August Kekulé's 1858 proposal of tetravalent carbon and linked-atom chains provided a theoretical framework that transitioned descriptions from mere empirical formulas to defined structural representations.^[5]

Physical Properties

Appearance and Phase Behavior

Propanamide is a white to off-white crystalline solid at room temperature, often appearing as flakes or powder.^[1]^[2] Its melting point ranges from 76 to 79 °C, with a literature value of 78–79 °C reported by NIST.^[6]^[7] This elevated melting point relative to hydrocarbons of similar molecular weight arises from strong intermolecular hydrogen bonding between amide groups.^[8] The compound has a boiling point of 213 °C (486 K) at standard pressure, with literature values ranging from 213–222 °C.^[6]^[2]^[9] Propanamide exhibits thermal stability under ambient conditions but decomposes upon prolonged heating or in fire, releasing carbon oxides and nitrogen oxides.^[6] The density is 1.04 g/cm³ at 20–25 °C.^[6]^[2]

Solubility and Spectroscopic Data

Propanamide demonstrates high solubility in water, exceeding 720 g/L at 20 °C, primarily due to extensive hydrogen bonding involving its amide functionality. It is freely soluble in polar organic solvents including ethanol, methanol, acetone, diethyl ether, and chloroform, reflecting its ability to interact via dipole-dipole forces and hydrogen bonding in these media. In contrast, propanamide shows negligible solubility in nonpolar solvents such as hexane, consistent with its polar molecular structure lacking compatibility with apolar environments.^[8] The infrared (IR) spectrum of propanamide features distinctive bands characteristic of primary amides, with N-H stretching vibrations appearing as twin peaks between 3350 and 3180 cm⁻¹, a strong C=O stretching absorption at approximately 1670 cm⁻¹, and an N-H bending mode around 1640 cm⁻¹.^[11] These signatures arise from the conjugated amide system and are useful for confirming the presence of the -CONH₂ group.^[12] In nuclear magnetic resonance (NMR) spectroscopy, propanamide's ¹H NMR spectrum (in CDCl₃) reveals three main signals: a triplet at δ 1.15 (3H, CH₃), a quartet at δ 2.25 (2H, CH₂), and a broad singlet at δ 6.5–7.5 (2H, NH₂), where the NH₂ protons are deshielded due to hydrogen bonding and exhibit broadening from exchange.^[13] The ¹³C NMR spectrum displays three distinct resonances at δ 9.5 (CH₃), 27.5 (CH₂), and 174.5 (C=O), corresponding to the ethyl chain carbons and the carbonyl carbon, respectively, with the latter shifted downfield by the electronegative oxygen.^[14] Mass spectrometry of propanamide under electron ionization conditions shows the molecular ion [M]⁺ at m/z 73, with the base peak at m/z 44 resulting from the loss of NH₃ via alpha-cleavage, a common fragmentation pathway for amides that aids in structural elucidation.^[1]

Synthesis

Laboratory Methods

Propanamide can be synthesized in laboratory settings through the thermal dehydration of ammonium propionate, a classical method for preparing primary amides from carboxylic acid ammonium salts. This involves heating ammonium propionate (CH₃CH₂COONH₄) to temperatures between 150–200 °C, typically for several hours under anhydrous conditions to drive off water and form the amide. The reaction proceeds according to the equation:

\text{CH}_3\text{CH}_2\text{COONH}_4 \rightarrow \text{CH}_3\text{CH}_2\text{CONH}_2 + \text{H}_2\text{O}

This approach requires careful control of temperature to avoid side reactions such as charring, and it is often conducted in a round-bottom flask equipped with a reflux condenser or under reduced pressure to facilitate water removal.^[15] An alternative and commonly employed laboratory method is the ammonolysis of propanoyl chloride with ammonia, which proceeds rapidly at room temperature or with mild cooling due to the high reactivity of acid chlorides toward nucleophilic acyl substitution. Propanoyl chloride (CH₃CH₂COCl) is reacted with excess anhydrous ammonia, often dissolved in an inert solvent like diethyl ether, to form propanamide and neutralize the hydrochloric acid byproduct as ammonium chloride. The stoichiometry requires excess ammonia (typically two equivalents: one for substitution and one for acid scavenging), and the reaction equation is:

\text{CH}_3\text{CH}_2\text{COCl} + 2\text{NH}_3 \rightarrow \text{CH}_3\text{CH}_2\text{CONH}_2 + \text{NH}_4\text{Cl}

The mixture is stirred until gas evolution ceases, followed by filtration to remove the salt precipitate. This method is favored in educational and research labs for its simplicity and speed, often achieving yields of 70–90% after purification.^[16] In both procedures, the crude propanamide is purified by recrystallization from hot water or ethanol, exploiting its moderate solubility in these solvents at elevated temperatures and low solubility upon cooling, which yields white crystalline solids with melting points around 79–82 °C. Safety precautions are essential: the ammonolysis reaction must be performed in a fume hood to handle the evolution of HCl gas and ammonia vapors, while wearing appropriate protective equipment; the dehydration step requires ventilation to manage potential ammonia release and heating hazards.^[15]^[17]

Industrial Production

An industrial method for producing propanamide involves the reaction of propanoic acid with urea at elevated temperatures of 150–180 °C, typically catalyzed by acids to enhance efficiency. The balanced equation for this process is:

(\ce{NH2})2\ce{CO} + 2 \ce{CH3CH2COOH} \rightarrow 2 \ce{CH3CH2CONH2} + \ce{CO2} + \ce{H2O}

This approach yields over 80% propanamide based on propanoic acid, with the reaction proceeding via initial formation of an acylurea intermediate that decomposes to release ammonia for amidation while generating gaseous byproducts.^[18] Another method employs the direct reaction of propanoic acid with ammonia at 180–250 °C, often in the gas phase over catalysts, achieving yields up to 92%. Ammonium propanoate, formed by neutralizing propanoic acid with ammonia, can also be dehydrated at high temperatures in continuous flow reactors to produce propanamide, with optimization to minimize side reactions such as formation of nitriles.^[19] Due to propanamide's niche applications, commercial production remains limited in scale, primarily integrated into facilities deriving propanoic acid from petrochemical feedstocks like ethylene or propylene oxidation.^[1] Commercial grades of propanamide achieve purity levels exceeding 98%, achieved through distillation or recrystallization, with byproducts such as CO₂ captured via scrubbing systems to meet environmental standards.^[15]

Chemical Properties and Reactions

Hydrolysis Reactions

Hydrolysis of propanamide proceeds under either acidic or basic conditions to yield propanoic acid and ammonia or its derivatives, reflecting the general reactivity of primary amides. In acidic hydrolysis, propanamide reacts with water in the presence of hydrochloric acid to form propanoic acid and ammonium chloride, typically requiring reflux for 4–6 hours to achieve quantitative yields.^[20]^[21] Under basic conditions, propanamide undergoes hydrolysis with sodium hydroxide at elevated temperatures, producing sodium propanoate and ammonia gas; this process is slower than the acidic variant and often necessitates prolonged heating compared to ester hydrolysis.^[22]^[20] The mechanism for both acidic and basic hydrolysis follows a nucleophilic addition-elimination pathway at the carbonyl carbon. In the acidic route, protonation of the carbonyl oxygen enhances electrophilicity, enabling water addition to form a tetrahedral intermediate, followed by proton transfers and elimination of the ammonium group. Basic hydrolysis involves direct nucleophilic attack by hydroxide on the carbonyl, forming a similar intermediate before expulsion of the amide nitrogen as ammonia. Amides like propanamide hydrolyze more slowly than analogous esters due to resonance stabilization of the carbonyl group by the nitrogen lone pair, which imparts partial double-bond character to the C–N bond and reduces the electrophilicity of the carbonyl carbon.^[21]^[20] In analytical chemistry, hydrolysis of propanamide serves to confirm the presence of an amide functional group, as the liberation of ammonia upon heating with sodium hydroxide produces a detectable odor or turns damp red litmus paper blue.^[22]

Rearrangement and Reduction Reactions

Propanamide undergoes the Hofmann rearrangement when treated with bromine and excess base such as potassium hydroxide (typically 4 equivalents), converting the primary amide to ethylamine with one fewer carbon atom via an isocyanate intermediate.^[23] The reaction proceeds through formation of an N-bromoamide, followed by deprotonation and migration of the ethyl group to nitrogen, yielding the isocyanate CH₃CH₂N=C=O, which hydrolyzes to the amine; typical yields for this transformation range from 60% to 80%.^[23] The overall equation is:

\ce{CH3CH2CONH2 + Br2 + 4 KOH -> CH3CH2NH2 + 2 KBr + K2CO3 + 2 H2O}

^[23] This method is particularly useful for preparing primary amines from carboxylic amides, preserving stereochemistry at the migrating carbon.^[24] Reduction of propanamide with lithium aluminum hydride (LiAlH₄) in ether solvent transforms the amide to n-propylamine by reducing the carbonyl group and cleaving the C-N bond, adding two hydrogens to the carbon chain./Amides/Reactivity_of_Amides/Conversion_of_Amides_into_Amines_with_LiAlH4) The mechanism involves stepwise hydride addition to the carbonyl, forming an iminium intermediate that is further reduced, followed by workup with water to liberate the amine.^[25] The balanced equation, representing the net reduction, is:

\text{CH}_3\text{CH}_2\text{CONH}_2 + 4 [\text{H}] \rightarrow \text{CH}_3\text{CH}_2\text{CH}_2\text{NH}_2 + 2 \text{H}_2\text{O}

This reduction is selective for primary amides, yielding primary amines without affecting other functional groups under controlled conditions./Amides/Reactivity_of_Amides/Conversion_of_Amides_into_Amines_with_LiAlH4) Dehydration of propanamide to propionitrile (CH₃CH₂CN) can be achieved under harsh conditions using dehydrating agents such as phosphorus pentoxide (P₂O₅) or thionyl chloride (SOCl₂), removing the elements of water from the amide functionality.^[26] The reaction typically requires heating and proceeds via activation of the hydroxyl group in an intermediate, followed by elimination, often in low to moderate yields due to side reactions.^[27] This transformation shortens the functional group but retains the carbon skeleton, providing a route to nitriles for further synthetic elaboration.^[27] The carbonyl carbon in propanamide is less electrophilic toward nucleophilic attack compared to esters, owing to resonance donation from the amino group that delocalizes electron density into the C=O π* orbital, stabilizing the amide and reducing its reactivity in non-reductive transformations./Amides/Properties_of_Amides)

Applications

Role in Organic Synthesis

Propanamide serves as a model compound in organic chemistry education to illustrate the reactivity and properties of primary amides, particularly their hydrogen bonding capabilities and resistance to hydrolysis compared to other carbonyl derivatives. In instructional contexts, it exemplifies amide reduction and spectroscopic characteristics, aiding in the understanding of functional group interconversions without the complexity of larger substituents.^[28] As a synthetic intermediate, propanamide undergoes Hofmann rearrangement to yield ethylamine, a key precursor in pharmaceutical synthesis for compounds like antihistamines and local anesthetics.^[24] Reduction of propanamide with lithium aluminum hydride produces n-propylamine, which is utilized in the preparation of pharmaceutical agents such as certain antidepressants and agrochemical intermediates. These transformations highlight propanamide's role in generating short-chain amines essential for medicinal chemistry applications.^[29] N-substituted derivatives of propanamide, such as N-aryl-3-(indol-3-yl)propanamides, are employed in studies of short-chain amide mimics for peptide analogs, particularly in evaluating immunosuppressive and enzyme inhibitory activities.^[30] These modifications allow researchers to probe amide bond stability and biological interactions in simplified peptide-like structures, contributing to the design of falcipain-2 inhibitors for antimalarial research.^[31] A notable application involves the dehydration of propanamide to propionitrile, serving as a building block in agrochemical synthesis, including pyrethroid pesticides for crop protection.^[32] This process underscores propanamide's utility in accessing nitrile intermediates for further derivatization in pest control agents.^[33]

Industrial and Other Uses

Derivatives such as 3-{N-[2-(N',N'-dimethylamino ethoxy)ethyl]-N-methylamino}propionamide act as catalysts in the production of polyurethane foams, enhancing processing efficiency in industrial manufacturing.^[34] In the agrochemical sectors, derivatives of propanamide, such as propanil, are used for weed control in rice cultivation.^[35] Related derivatives, like 2-hydroxy-N,N-dimethylpropanamide, are approved as inert solvents or co-solvents in pesticide formulations, aiding in the application of herbicides on crops while minimizing environmental residue concerns.^[36] Propanamide is employed in pharmaceutical research as a precursor for synthesizing drug candidates, including enzyme inhibitors such as propanamide-sulfonamide hybrids that exhibit dual activity against urease and cyclooxygenase-2, offering potential for anti-inflammatory and antimicrobial therapies.^[37] Beyond these areas, propanamide acts as a solvent in niche industrial formulations, supporting specialized chemical processes due to its polar properties and solubility characteristics.^[38]

Safety and Environmental Considerations

Health and Toxicity Profile

Propanamide exhibits low acute toxicity, with an oral LD50 greater than 2,000 mg/kg in female rats, indicating it is not highly toxic by this route.^[6] Inhalation toxicity data are limited, with an LCLo of 8,000 ppm reported in rats, suggesting minimal acute hazard under typical exposure conditions.^[1] The compound causes serious but reversible eye irritation, classified under GHS Category 2A, though it does not produce skin irritation in standardized tests.^[6] As a solid, propanamide dust may act as a mild irritant to mucous membranes upon contact.^[6] Chronic toxicity data for propanamide are limited, with the RTECS code UE2975000 reflecting minimal investigated hazards and no established long-term effects in available studies.^[6] Inhalation of dust may cause respiratory irritation, but no specific chronic respiratory or systemic effects have been documented.^[6] Propanamide shows no evidence of mutagenicity, testing negative in the Ames bacterial reverse mutation assay.^[6] It is not classified as a carcinogen by the International Agency for Research on Cancer (IARC).^[39] In the environment, propanamide is readily biodegradable, achieving 89% degradation over 28 days in standard tests, and exhibits low bioaccumulation potential with a log Kow of approximately -0.7.^[6]

Handling Precautions

Propanamide should be stored in a cool, dry place below 30 °C in tightly sealed containers to prevent moisture absorption, which can lead to hydrolysis.^[6] Well-ventilated storage areas are recommended to minimize dust accumulation, and the material should be kept away from incompatible substances such as strong oxidizing agents.^[40] When handling propanamide, appropriate personal protective equipment (PPE) is essential, including nitrile rubber gloves with a minimum thickness of 0.11 mm, safety goggles or glasses compliant with NIOSH or EN 166 standards, a laboratory coat or protective clothing, and respiratory protection such as a P2 filter mask in areas where dust may be generated.^[6] Operations should be conducted in well-ventilated fume hoods or areas to control dust exposure and avoid inhalation or skin contact.^[41] In the event of a spill, personnel should evacuate the area, ensure adequate ventilation, and wear appropriate PPE before approaching. The spill should be contained to prevent entry into drains or waterways, absorbed using an inert material such as vermiculite or sand, and collected into suitable containers for disposal; any hydrolyzed residues may require neutralization with water followed by thorough rinsing.^[6]^[40] Propanamide is not classified as a hazardous material for transport under the U.S. Department of Transportation (DOT), International Maritime Dangerous Goods (IMDG), or International Air Transport Association (IATA) regulations, as it is neither flammable nor corrosive.^[41] Under the Globally Harmonized System (GHS), it is classified as an eye irritant (H319), warranting a warning label for handling.^[6] For disposal, propanamide and any contaminated materials should be incinerated at a licensed facility or, if suitable, diluted and treated as non-hazardous aqueous waste in accordance with local, national, and international regulations to avoid environmental release.^[40] Contaminated packaging must be disposed of similarly to the product itself.^[41]

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