2-Furancarboxaldehyde (furfural)
2-Furaldehyde
CAS: 98-01-1
Molecular Formula: C5H4O2
2-Furancarboxaldehyde (furfural) - Names and Identifiers
2-Furancarboxaldehyde (furfural) - Physico-chemical Properties
| Molecular Formula | C5H4O2 |
| Molar Mass | 96.08 |
| Density | 1.16 g/mL at 25 °C (lit.) |
| Melting Point | -36 °C (lit.) |
| Boling Point | 162 °C (lit.) |
| Flash Point | 137°F |
| JECFA Number | 450 |
| Water Solubility | 8.3 g/100 mL |
| Solubility | 95% ethanol: soluble1ML/mL, clear |
| Vapor Presure | 13.5 mm Hg ( 55 °C) |
| Vapor Density | 3.31 (vs air) |
| Appearance | Liquid |
| Color | very deep brown |
| Exposure Limit | NIOSH REL: IDLH 100 ppm; OSHA PEL: TWA 5 ppm (20 mg/m3); ACGIHTLV: TWA 2 ppm (adopted). |
| Merck | 14,4304 |
| BRN | 105755 |
| PH | >=3.0 (50g/l, 25℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Substances to be avoided include strong bases, strong oxidizing agents and strong acids. Flammable. |
| Sensitive | Air Sensitive |
| Explosive Limit | 2.1-19.3%(V) |
| Refractive Index | n20/D 1.527 |
| Physical and Chemical Properties | Colorless transparent oily liquid with special odor similar to benzaldehyde. The color changes rapidly to red-brown when exposed to light and air. It is easy to volatilize with vapor. boiling point 161.7 ℃ freezing point -36.5 ℃ relative density 1.1594 refractive index 1.5263 flash point 60 ℃ solubility slightly soluble in water, soluble in ethanol, ether, acetone, chloroform, benzene. |
| Use | Used as raw materials for organic synthesis, but also for the synthesis of resins, varnishes, pesticides, pharmaceuticals, rubber and coatings |
2-Furancarboxaldehyde (furfural) - Risk and Safety
| Risk Codes | R21 - Harmful in contact with skin R23/25 - Toxic by inhalation and if swallowed. R36/37 - Irritating to eyes and respiratory system. R40 - Limited evidence of a carcinogenic effect R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S1/2 - Keep locked up and out of the reach of children. S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | UN 1199 6.1/PG 2 |
| WGK Germany | 2 |
| RTECS | LT7000000 |
| FLUKA BRAND F CODES | 1-8-10 |
| TSCA | Yes |
| HS Code | 2932 12 00 |
| Hazard Note | Irritant |
| Hazard Class | 6.1 |
| Packing Group | II |
| Toxicity | LD50 orally in rats: 127 mg/kg (Jenner) |
2-Furancarboxaldehyde (furfural) - Nature
Open Data Verified Data
colorless or light yellow oily liquid with special odor of benzaldehyde. Dew in the air and light easy to become yellow-brown, and the formation of resin-like, with water vapor volatilization, easily soluble in alcohol and ether, soluble in hot water, acetone, soluble in benzene, chloroform, soluble in 11 water. Flammable. Corrosive. Can stimulate the mucosa, tear, cause Head Pain. In case of open flame, high heat or contact with oxidant, there is a risk of combustion explosion. By high heat decomposition of toxic gases. In case of high fever, the internal pressure of the container increases, and there is a risk of cracking and explosion. An explosive mixture can be formed in the presence of air.
Last Update：2024-01-02 23:10:35
2-Furancarboxaldehyde (furfural) - Preparation Method
Open Data Verified Data
The corncob was crushed and added to the hydrolysate prepared by sulfuric acid and salt, and stirred evenly. A dilute solution of furfural is obtained by heating to boiling. After standing, refined to pure product.
Last Update：2022-01-01 09:30:36
2-Furancarboxaldehyde (furfural) - Use
Open Data Verified Data
Check the drill and determine the sulfate. Reagents for the determination of aromatic amines, acetone, alkaloids, vegetable oils and cholesterols. Determination of pentose and pentose sugar when the standard. Synthetic resin, refined organic matter, nitrocellulose solvent, dichloroethane extractant.
Last Update：2022-01-01 09:30:36
2-Furancarboxaldehyde (furfural) - Safety
Open Data Verified Data
rat oral LD50:127mg/kg. Furfural can stimulate the skin and mucous membranes, the vapor is strongly irritating, and has an anesthetic effect. This product is toxic when inhaled or taken orally. The possibility of irreversible damage to the body. Staff should be protected from contact with eyes and skin. The maximum allowable concentration in air is 5 x 10 6. Store in a cool, ventilated warehouse. Keep away from fire and heat source. Protected from light. Packaging is required to be sealed and not to be in contact with air. Should not be large or long-lived. Should be stored separately from the oxidant, acid, alkali.
Last Update：2022-01-01 09:30:37
2-Furancarboxaldehyde (furfural) - Reference Information
| FEMA | 2489 | FURFURAL |
| freezing point | -36.5 ℃ |
| Henry's Law Constant | 1.52(x 10-6 atm?m3/mol) at 20 °C (approximate - calculated from water solubility and vapor pressure) |
| LogP | 0.41 |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 3 (Vol. 63) 1995 |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Product characteristics | furfural is a colorless and transparent oily liquid produced by hydrolysis and dehydration of pentosan in plant fiber materials, also known as furaldehyde, there is a special flavor, in the light, heat, air oxidation and inorganic acid under the action of color quickly turn yellow-brown, eventually into black-brown, but also prone to polymerization and resin-like. Storage should be protected from light, oxygen, sealing. Furfural and water are partially miscible, but also soluble in alcohol, ether, acetic acid and other solvents. The ability to dissolve aromatic hydrocarbons, olefins, polar substances and certain high molecular compounds is large, and the ability to dissolve saturated substances such as aliphatic hydrocarbons and higher fatty acids is small. A variety of derivatives can be formed by oxidation, hydrogenation, nitration, oxidation, decarbonylation, condensation and the like. The properties were very similar to those of benzaldehyde, and benzoin reaction, polgold reaction and conica Rol reaction could occur. The reaction of furfural with aniline and acetic acid solution is bright red, which is often used as a qualitative reagent for furfural. Quantitative analysis is based on two properties of aldehyde group and furan ring. In addition to Chromatography, there are volumetric methods (hydroxylamine hydrochloride method, tetrabromide method, etc.) and gravimetric methods (phloroglucinol method, barbituric acid method, etc.) finished product analysis was performed, and hydroxylamine hydrochloride method was used for the analysis of finished products in China. furfural is a solvent commonly used in refined petroleum, is an important raw material for synthetic resins, Electrical insulating materials, nylon, coatings, etc., or is a raw material and reagent for the preparation of drugs and a variety of organic synthesis. Mainly used as the production of furan derivatives (such as furfuryl alcohol, tetrahydrofurfuryl alcohol, methyl furan, decarbonylation of furan, oxidation of furoic acid, nitrofuran drugs, etc.), it is also used as a selective solvent for separating unsaturated compounds in saturated aliphatic compounds (such as petroleum-based lubricating oil, gasoline, kerosene and vegetable oil), a decolorizing agent for Rosin and a solvent for resin production, and an extractive distillation solvent for separating butadiene and the like from the C4 fraction. Resins made of furfural and furfuryl alcohol (such as furfuryl alcohol resin, furfural resin, etc.) are collectively referred to as furan resin, mainly used as casting resin, grinding wheel adhesive and anti-corrosion coating, etc. |
| History of discovery | D. W.Doberei-ner) reported the separation of a yellow oily substance from a turbid distillate during the preparation of formic acid by the addition of manganese dioxide and sulfuric acid to sucrose. The identification and nomenclature was not possible due to the small number. embryonic House (J.Stenhouse) with corn cob, oat shell to obtain the same product, and the chemical composition of the study to determine the molecular formula, it is thus concluded that furfural and its related products can be obtained from any plant material. However, its name was first named bran oil by G.Fownes in 1845, and then it was found to have the properties of aldehyde, and was changed to furfural. The industrial production of furfural was first announced by The Quaker Oats Co., USA, until 1922. In 1988, the annual output of the United States was about 60,000 tons, accounting for the first in the world. The main producing countries are Dominican, China, the Soviet Union, France, the Federal Republic of South Africa and other countries, the world's annual output of about 300,000 tons. China has been producing more than 40,000 tons of furfural since the 1943, and has been one of the major exporting countries in the world until 1989. |
| production process | furfural is produced from plant material rich in pentosan. Commonly used are corn cob, oat hull, cottonseed Hull, bagasse, Rice Husk, etc., to the best corn cob. Their average theoretical furfural content (%) was 23.4 for corncob, 22.3 for oat hulls, 18.6 for cottonseed hulls, 17.4 for bagasse, and 11.4 for rice hulls. The reaction process of pentosan conversion to furfural is carried out in two steps: If the above two reactions are carried out in the same equipment at the same time, it is called direct method (or one-step method), called the indirect method (or two-step method). The common direct method has the advantages of simple equipment, high yield, low cost and large production capacity, but the comprehensive utilization of each component in the raw material is poor, so the indirect method is still in the research and improvement. In the reaction process, furfural will further decompose into formic acid and humus. The yield of furfural depends on the formation of furfural and the decomposition of furfural. In addition to the characteristics of the raw materials, the factors affecting the furfural yield include the type and concentration of the catalyst, the solid-liquid ratio, the temperature, the amount of steam and the flow state of steam in the material layer. According to the characteristics of the raw materials, the types of catalysts and other conditions, different reaction equipment, hydrolysis processes and processing methods are used. Such as the United States queger Oat Company Law (including intermittent and continuous two), the French agricultural furan law, etc. China adopts vertical batch hydrolysis pot dilute sulfuric acid hydrolysis process: raw material and dilute sulfuric acid (4 ~ 10%) After mixing according to the liquid ratio of 0.3~0.5, it is put into the hydrolysis Pan, heated with direct steam, and the resulting furfural is taken out of the hydrolysis pan. After the vapor containing 3-6% of furfural is condensed (the secondary vapor is generated by recovering heat energy), it is sent to an initial distillation column for distillation, and the condensate at the top of the column contains about 30% of furfural, and is cooled to about 50 ° C. For stratification. The upper layer is sent to a low boiling point distillation tower, and the low boiling point is removed and then returned to the initial distillation tower to recover furfural; The lower layer is sent to a dehydration tower and a finishing tower to remove low boiling points such as moisture and high boiling points such as methyl furfural, respectively. If the organic acid content in the crude furfural is large, it can be treated by neutralization method or water washing method. The continuous hydrolysis process for furfural production has been applied to industrial production. The by-products such as methanol and acetic acid formed in the furfural production process can be recovered when needed. The hydrolysis residue lignin is mostly used as fuel, and a small amount of lignin is used as pesticide slow release agent, adhesive extender and soil conditioner. |
| assay | analyzed by aldehyde assay (OT-6). The amount of the sample was 1.5g. The equivalence factor (e) in the calculation is taken as 48.05. Or according to GT-10-4 in gas chromatography with non-polar column determination. |
| toxicity | LD50 65mg/kg (rat, oral). ADI is not specified (FAO/WHO,1994). |
| usage limit | FEMA(mg/kg): Soft drink 4.0; Cold drink 13; Candy 12; Baked goods 17; pudding 0.80; Gum 45; Wine 10; Syrup 30. |
| purpose | mainly used as industrial solvent for the preparation of furfuryl alcohol, furoic acid, Tetrahydrofuran, γ-valerolactone, pyrrole, tetrahydropyrrole and so on used as analytical reagent used as raw materials for organic synthesis, also used in the synthesis of resin, varnish, pesticide, medicine, rubber and paint used for tanning leather. Should be stored in a cool, ventilated warehouse, protected from light, to prevent sun exposure, away from fire. furfural is a raw material for the preparation of many drugs and industrial products. Furan can be reduced by electrolysis, and can also be made into butanedial, which is a raw material for the production of atropine. Some derivatives of furfural have strong bactericidal ability and broad antibacterial spectrum. For example, furacilin is obtained by condensation of furfural with semicarbazide hydrochloride via 5-nitrofurfural, which is a Disinfection preservative. Furfural is the raw material of furan acrylic acid, furfurylamine fumaric acid, adipic acid, furfuryl alcohol and other intermediates. It is widely used in the synthesis of fine chemicals such as medicines, pesticides, veterinary drugs, dyes, fragrances, rubber additives, preservatives and so on. The area in which furfural is most consumed is as a solvent and raw material for synthetic resins. In the synthetic resin, furan resin, furfural resin and furfural resin can be produced. Furan resin is also called furfuryl alcohol resin. Furfural is hydrogenated under high pressure to produce furfuryl alcohol, and furfuryl alcohol is polymerized to obtain furfuryl alcohol resin. This resin has a strong alkali resistance, High heat resistance and water resistance, can be used as joint filling resin cement, anti-corrosion lining, Binder. As a solvent, furfural can selectively extract unsaturated components from petroleum and vegetable oils. The aromatic components in lubricating oil and diesel oil were extracted with furfural. To improve the quality of these products. In the production of synthetic rubber, butadiene and isoprene are purified by furfural extraction. Furfural can stimulate the skin and mucous membranes, the maximum allowable concentration of 5ppm in the air. The oral LD50 of rats was 127mg/kg. GB 2760-96 is allowed to use the food flavor; Extraction solvent. Mainly used for the preparation of a variety of heat-processed flavors, such as bread, butter hard candy, coffee and other flavors. furfural is an important organic chemical raw materials, can be used to prepare maleic anhydride, oxalic acid, furfuryl alcohol, Tetrahydrofuran, and can also be used to synthesize furfural resin, furan resin, rubber vulcanization accelerator, rubber antioxidant, preservatives, etc. Mainly used in medicine, pesticides, veterinary drugs and food industry. cobalt was assayed and sulfate was determined. Reagents for the determination of aromatic amines, acetone, alkaloids, vegetable oils and cholesterols. Determination of pentose and pentose as standard. Synthetic resin, refined organic matter, nitrocellulose solvent, dichloroethane extractant. |
| production method | The agricultural wastes rich in pentosan, such as corncob, cottonseed Hull, rice bran and sugar beet residue, are hydrolyzed with dilute acid, dehydrated and distilled. furfural was initially obtained from rice bran, and furfural was produced by hydrolysis and dehydration of polypentose in agricultural products. Many crops of the stem, bark, litter shell contains pentose, so can be used as a raw material for the production of furfural. During production, raw materials such as corncob, cottonseed shell or bagasse are treated with sulfuric acid and steam, and then subjected to steam distillation, stratification and vacuum distillation, and the product with a purity of 99% can be obtained. The recovery of furfural is related to the raw material, the type and concentration of acid and other conditions, and usually differs greatly from the theoretical yield. There are two main methods for the industrial production of furfural. The pressure method is suitable for large-scale production. The raw materials and dilute sulfuric acid are cooked under pressure, and the reaction product is taken out with high pressure or superheated steam, and the sugar aldehyde product is obtained after fractionation; the atmospheric pressure method is to boil the raw materials together with salt and other inorganic salts and dilute sulfuric acid and simultaneously boil off furfural. 0.5 of corncob was crushed into 25kg ~ 1 cm2 of small pieces, 90% of sulfuric acid and 2.5 of salt and water were added to prepare the hydrolysate, so that the volume of the hydrolysate was times of the corncob. After the corncob is homogenized with the hydrolysate, it is heated to boiling, I .e., the dilute solution of furfural is started to be distilled off, and condensed and collected in the separator. The aqueous phase was separated by standing for 1-2H to obtain crude furfural. Purified by steam distillation to obtain pure product. |
| category | toxic substances |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LD50: 65 mg/kg; Oral-mouse LD50: 400 mg/kg |
| stimulation data | Skin-rabbits 20 mg/24 h moderate; eye-rabbit 100 mg/24 h moderate |
| explosive hazard characteristics | explosive when mixed with air |
| flammability hazard characteristics | open flame combustible; High heat emission stimulus gas |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; With oxidant, acid, alkali, separate storage of food additives |
| fire extinguishing agent | water mist, dry powder, foam, carbon dioxide |
| Occupational Standard | TLV-TWA 2 PPM (8 mg/m3); TWA 5 PPM (20 mg/m3) |
| spontaneous combustion temperature | 599 f &_& 599 f |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
| immediate life-and health-threatening concentration | 100 ppm |
Last Update：2024-04-10 20:36:47
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