Furfural is an organic compound derived from plant materials. It is utilized in various industries, including pharmaceuticals, resins, and fuels, due to its versatility and renewable nature.
| IUPAC Name | Furan-2-carbaldehyde |
| Molecular Formula | C5H4O2 |
| CAS Number | 98-01-1 |
| Synonyms | Furfuraldehyde; 2-Furaldehyde; 2-Formylfuran, 2-Furancarboxaldehyde |
| InChi | InChI=1S/C5H4O2/c6-5-1-2-7-4-3-5/h1-4H |
Furfural Properties
Furfural Formula
The chemical formula of furfural or furfuraldehyde is C5H4O2. It represents the specific arrangement of atoms within the molecule, indicating the presence of five carbon atoms, four hydrogen atoms, and two oxygen atoms. This formula is essential in understanding the compound’s composition and molecular structure, aiding in various chemical processes and applications.
Furfural Molar Mass
Furfuraldehyde’s molar mass is calculated by summing up the atomic masses of each element present in its chemical formula. With a molecular formula of C5H4O2, the molar mass of furfuraldehyde is approximately 96.08 grams per mole (g/mol). This information is crucial in determining the amount of furfuraldehyde in a given sample during chemical reactions and industrial processes.
Furfural Boiling Point
Furfuraldehyde has a boiling point of about 161-165°C (321-329°F). This temperature indicates the point at which the liquid substance changes into a vapor state at atmospheric pressure. Understanding the boiling point is vital in applications where furfuraldehyde needs to be vaporized or distilled.
Furfural Melting Point
The melting point of furfuraldehyde is around -36.5°C (-33.7°F). This temperature signifies the point at which the solid form of furfuraldehyde transitions into a liquid. Knowing the melting point is significant for the storage, handling, and processing of the compound in solid-state applications.
Furfural Density g/mL
Furfuraldehyde’s density is approximately 1.159 grams per milliliter (g/mL). Density measures the mass of a substance per unit volume. This value is valuable in determining the space furfuraldehyde occupies and plays a crucial role in its storage, transportation, and usage in various industries.
Furfural Molecular Weight
The molecular weight of furfuraldehyde, also known as the molar mass, is approximately 96.08 g/mol. This value represents the mass of one mole of furfuraldehyde molecules and aids in stoichiometric calculations and determining reactant quantities.
Furfural Structure
Furfuraldehyde features a ring structure known as a furan ring, composed of four carbon atoms and one oxygen atom. The fifth carbon forms an aldehyde group. The arrangement of atoms gives furfuraldehyde its aromatic and aldehyde properties, making it valuable in chemical synthesis.
Furfural Solubility
Furfuraldehyde is sparingly soluble in water. It dissolves better in organic solvents, such as ethanol and diethyl ether. Understanding its solubility is vital for formulating appropriate solutions and controlling its concentration in various applications, including as a solvent and chemical intermediate.
| Appearance | Colorless to yellow liquid |
| Specific Gravity | 1.159 g/mL |
| Color | Colorless to yellow |
| Odor | Aromatic, Almond-like |
| Molar Mass | 96.08 g/mol |
| Density | 1.159 g/mL |
| Melting Point | -36.5°C (-33.7°F) |
| Boiling Point | 161-165°C (321-329°F) |
| Flash Point | 60°C (140°F) |
| Water Solubility | Sparingly soluble |
| Solubility | Soluble in organic solvents such as ethanol and diethyl ether |
| Vapour Pressure | 4.5 mmHg at 25°C |
| Vapour Density | 3.29 (air = 1) |
| pKa | 7.1 |
| pH | 4.5-5.5 |
Furfural Safety and Hazards
Furfuraldehyde poses some safety hazards that require proper handling and precautions. It is a flammable liquid with a flash point of 60°C (140°F), making it susceptible to ignition. Inhalation of vapors may cause respiratory irritation and dizziness. Direct contact with the skin and eyes may lead to irritation and redness. To ensure safety, use adequate ventilation and personal protective equipment when handling furfuraldehyde. Store it away from sources of heat or open flames. In case of spills, promptly clean up using appropriate absorbent materials. Proper training and awareness are essential to minimize the risks associated with furfuraldehyde handling.
| Hazard Symbols | Flammable |
| Safety Description | Flammable liquid. Avoid direct contact. Use in a well-ventilated area. Keep away from heat and open flames. |
| UN IDs | UN 1199 |
| HS Code | 29321100 |
| Hazard Class | Class 3 – Flammable liquids |
| Packing Group | PG II |
| Toxicity | May cause irritation and dizziness on inhalation. Irritating to skin and eyes. |
Furfural Synthesis Methods
In the synthesis of furfuraldehyde, various methods exist.
One such common approach involves catalyzing the acid-induced dehydration of pentoses, such as xylose and arabinose, which originate from agricultural waste materials like corn cobs or bagasse. In this process, the pentose sugars undergo dehydration in the presence of a strong acid catalyst, typically sulfuric acid, at elevated temperatures. The acid removes water from the sugar molecules, leading to the formation of furfuraldehyde.
Another method entails oxidizing furfuryl alcohol in the vapor phase, obtained from reducing furfuraldehyde itself. The vapor-phase oxidation employs air or oxygen as the oxidizing agent and catalysts like metal oxides to convert furfuryl alcohol back into furfuraldehyde.
Furthermore, biomass-based furfuraldehyde production has gained attention, involving the use of various lignocellulosic materials, such as corncobs, rice husks, or sugarcane bagasse. Subsequently, these feedstocks undergo different processes like hydrolysis, solvent extraction, and dehydration, resulting in the production of furfuraldehyde.
Each of these synthesis methods plays a crucial role in harnessing furfuraldehyde’s potential as a renewable and versatile platform chemical, paving the way for sustainable production routes in the chemical industry.
Furfural Uses
Furfuraldehyde finds a wide range of applications due to its versatile nature and unique properties. Here are some common uses:
- Solvent: Furfuraldehyde serves as a solvent in various chemical processes, particularly in the extraction of lubricants, resins, and waxes.
- Pharmaceuticals: It acts as a precursor in the synthesis of several pharmaceutical compounds, contributing to drug development.
- Agricultural Chemicals: It is a key component in producing pesticides, herbicides, and fungicides to protect crops.
- Corrosion Inhibitor: Furfuraldehyde functions as a corrosion inhibitor for metals, preventing their deterioration in various industrial settings.
- Flavoring Agent: Its aromatic properties make it suitable for enhancing flavors in food and beverage products.
- Fuel Additive: It serves as an additive in gasoline and diesel fuels, enhancing their combustion efficiency.
- Resin Production: Furfuraldehyde plays a vital role in manufacturing furan resins, which find applications in adhesives, binding agents, and foundries.
- Rubber Industry: The rubber industry utilizes furfuraldehyde to enhance the vulcanization process and improve the properties of rubber.
- Renewable Resource: Furfuraldehyde, derived from biomass, offers an eco-friendly alternative to petrochemicals for specific applications.
- Plastics: Manufacturers have developed furfuraldehyde-based plastics for various products, including packaging materials.
These diverse applications highlight the importance of furfuraldehyde as a valuable compound across multiple industries, contributing to the development of sustainable and innovative solutions.
Questions:
Q: How to convert lignocellulose to furfural?
A: Lignocellulose can be converted to furfuraldehyde by subjecting it to acid-catalyzed dehydration, where pentose sugars are transformed into furfuraldehyde.
Q: How many dehydration reactions occur in the conversion of a molecule of an aldopentose to furfural?
A: In the conversion of an aldopentose to furfuraldehyde, four dehydration reactions take place.
Q: How much dehydration must occur for furfural to form from a furanose?
A: Two dehydrations are required for a furfuraldehyde to form from a furanose.
Q: Where is furfural found in nature?
A: Furfuraldehyde is found naturally in certain plants, agricultural waste, and various biomass sources.
Q: What is furfural?
A: Furfuraldehyde is an organic compound derived from plant materials, possessing an aromatic and aldehyde nature.
Q: Is furfural a phenol?
A: No, furfuraldehyde is not a phenol. It is an aldehyde compound with a furan ring structure.
Q: Is furfural a tannin?
A: No, furfuraldehyde is not a tannin. Tannins are a different class of compounds found in plants.