2-Ethylhexanol
2-Ethyl-1-hexanol
CAS: 104-76-7
Molecular Formula: C8H18O
2-Ethylhexanol - Names and Identifiers
| Name | 2-Ethyl-1-hexanol |
| Synonyms | FEMA 3151 octan-3-ol ISOOCTANOL ALCOHOL C8 2-ETHYLHEXANOL 2-Ethylhexanol 2-ethyl hexanol ISOOCTYL ALCOHOL 2-Ethylhexan-1-ol 2-Ethyl-1-hexanol 'ISOOCTYL ALCOHOL' ETHYL-1-HEXANOL, 2- 1-ETHYL-N-AMYLCARBINOL (2R)-2-ethylhexan-1-ol (2S)-2-ethylhexan-1-ol titanium(4+) tetrakis(2-ethylhexan-1-olate) |
| CAS | 104-76-7 |
| EINECS | 203-234-3 |
| InChI | InChI=1/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3/t8-/m0/s1 |
| InChIKey | YIWUKEYIRIRTPP-UHFFFAOYSA-N |
2-Ethylhexanol - Physico-chemical Properties
| Molecular Formula | C8H18O |
| Molar Mass | 130.23 |
| Density | 0.833g/mLat 25°C(lit.) |
| Melting Point | −76°C(lit.) |
| Boling Point | 183-186°C(lit.) |
| Flash Point | 171°F |
| JECFA Number | 267 |
| Water Solubility | 1 g/L (20 ºC) |
| Solubility | water: solubleg/L at 20°C |
| Vapor Presure | 0.2 mm Hg ( 20 °C) |
| Vapor Density | 4.49 (vs air) |
| Appearance | Liquid |
| Color | Clear |
| Odor | sweet. |
| Merck | 14,3808 |
| BRN | 1719280 |
| pKa | 15.05±0.10(Predicted) |
| PH | 7 (1g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, strong acids. |
| Explosive Limit | 0.88%, 104°F |
| Refractive Index | n20/D 1.431(lit.) |
| MDL | MFCD00004746 |
| Physical and Chemical Properties | Colorless to light yellow oily liquid, with sweet taste and light floral fragrance. Soluble in 720 times water, miscible in most organic solvents. Boiling point 183 °c, melting point -70 °c. |
| Use | Used in the production of plasticizers, defoamers, dispersants, mineral dressing agents and oil additives, also used in printing and dyeing, paint, film and other aspects |
2-Ethylhexanol - Risk and Safety
| Risk Codes | R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes R36 - Irritating to the eyes R21 - Harmful in contact with skin R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36/37/38 - Irritating to eyes, respiratory system and skin. R20 - Harmful by inhalation |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/39 - S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S36 - Wear suitable protective clothing. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| WGK Germany | 2 |
| RTECS | MP0350000 |
| TSCA | Yes |
| HS Code | 29339990 |
| Toxicity | LD50 orally in Rabbit: 3730 mg/kg LD50 dermal Rat > 3000 mg/kg |
2-Ethylhexanol - Upstream Downstream Industry
| Raw Materials | Propylene |
| Downstream Products | 2-Ethylhexanoic Acid 2-Ethylhexyl acrylate tris(2-ethylhexyl) phosphate Adipic acid di-n-octyl ester Dioctyl phthalate Dioctyl sebacate dioctyl terephthalate |
2-Ethylhexanol - Nature
Open Data Verified Data
Colorless transparent flammable liquid with special odor. Soluble in about 720 times of water, miscible with most organic solvents. In case of high heat, open flame or contact with oxidant, there is a risk of combustion. In case of high fever, the internal pressure of the container increases, and there is a risk of cracking and explosion. Can form an explosive mixture with air. Can accumulate static electricity, ignition its vapor.
Last Update：2024-01-02 23:10:35
2-Ethylhexanol - Preparation Method
Open Data Verified Data
acetaldehyde condensation method is the first two molecules of ethanol condensation to produce butanol aldehyde, and then dehydration to produce crotonaldehyde (crotonaldehyde), butenal by hydrogenation of N-butyraldehyde; N-butyl alcohol; in the case of dehydration by condensation, 2-ethylhexenal is formed, and further hydrogenation is carried out to obtain the final product 2-ethylhexanol. Alternatively, n-butyraldehyde and isobutyraldehyde can be synthesized by high pressure carbonyl synthesis using propylene, carbon monoxide and hydrogen as raw materials and cobalt tetracarbonyl hydrogen as catalyst. The hydrogenation of N-butyraldehyde and isobutyraldehyde takes copper or nickel as catalyst. N-butyl aldehyde is hydrogenated in gas phase or solid phase to produce n-butyl alcohol. After initial distillation, n-butyl alcohol is purified in two-column distillation system. Using sodium hydroxide as a catalyst to make n-butanol condensation, dehydration of 2 ethyl hexenal. 2 ethyl hexenal hydrogenation in the presence of nickel catalyst, under certain temperature and pressure hydrogenation of iso2 ethyl hexanol.
Last Update：2022-01-01 09:27:51
2-Ethylhexanol - Use
Open Data Verified Data
used as a defoamer for drilling fluid. It is also used to prepare dioctyl phthalate, dioctyl azelate and other plasticizers.
Last Update：2022-01-01 09:27:51
2-Ethylhexanol - Safety
Open Data Verified Data
rat oral LD50: 12.46 ml/kg. Ingestion, inhalation or absorption through the skin is harmful to the body, can cause allergic reactions in the skin. Has a strong stimulating effect on the eyes, eyes contact with this product, can damage the eyes; Stored in a cool, ventilated warehouse. Keep away from fire and heat source. Protection from direct sunlight. Keep the container sealed. Should be stored separately from oxidants and acids.
Last Update：2022-01-01 09:27:51
2-Ethylhexanol - Reference Information
| FEMA | 3151 | 2-ETHYL-1-HEXANOL |
| olfactory threshold (Odor Threshold) | 0.013ppm |
| LogP | 2.9 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| preparation | 1. butyraldehyde (30g,0.42 mol),5% sodium hydroxide aqueous solution (15 mL) and ethanol (50 mL) were added into a 250 mL 3-mouth bottle of 2-ethyl -2-enhexal, stirred in a water bath at 40 ℃ overnight, TLC detection reaction, spin evaporation to remove ethanol, and extraction with 100mL ethyl acetate in three times, combine organic layers, wash purified water, wash brine, dry anhydrous magnesium sulfate, filter and spin to obtain light yellow transparent liquid (13.8g, yield 52%). 2. synthesize 2-ethyl -2-enhexanol. add 2-ethyl -2-enhexal (5g,40 mmol), sodium borohydride (3g,80 mmol), anhydrous methanol (20mL), stirring reaction at room temperature for 3 hours, add 10mL of purified water under ice bath condition, extract ethyl acetate, combine organic layers, wash purified water, wash saturated salt water, dry anhydrous magnesium sulfate, filter, rotation drying, column chromatography purification, colorless transparent liquid 4.36g, yield: 85%. 3. Synthesize (S)-2-ethylhexanol in nitrogen atmosphere, add bisphosphorous ligand ChenPhos(3.28mg, 0.0021 mmol), Rh(NBD)2BF4,( 1.50 mg, 0.002 mmol) and dichloromethane (2 mL) to 10ml of reaction inner tube, stir for 30 minutes, and obtain yellow clarified liquid, which is the catalyst. Add 2-ethyl-2-enhexanol (25.6mg, 0.2 mmol), then place the inner tube in a hydrogenation reactor, replace the system with hydrogen atmosphere through three hydrogenation and deflation operations, and finally pressurize to 50 atm, and stir at room temperature for 20 hours. Stop the reaction, release gas, rotate the reaction system to concentrate, and filter through silica gel column to obtain colorless oily liquid (25.2 mg) with 97% yield and 98.3% ee. |
| content analysis | determined by gas chromatography (GT-10). The conditions are: column length 30m, inner diameter 0.32mm. Carrier gas helium, pressure 62.3kPa, flow rate 95 ml/min, purification 3 ml/min. Detector, FID type, temperature 275 ℃. Sample quantity 1pl. The inlet temperature is 250 ℃, the column temperature is 80~250 ℃,IO ℃/min. The content is then calculated as a percentage of the standardized area. Or by gas chromatography (GT-10-4) with non-polar column method. |
| toxicity | LD503200~7600 mg/kg. Adl 0~0.5(FAO/WHO,1994). |
| use limit | FEMA: drinks, ice cream, candy, gum candy, all 10 mg/kg. |
| use | GB 2760-1996 allowed edible spices. Used in the production of plasticizers, defoamers, dispersants, mineral concentrators and petroleum additives, and also used in printing and dyeing, paints, films, etc. Used in the production of plasticizers, defoamers, dispersants, mineral concentrators and petroleum additives, and also used in printing and dyeing, paints, films, etc. 2-ethylhexanol is customarily called octanol in the plasticizer neighborhood, and it is an important chemical raw material. In addition to the production of plasticizers, foreign octanol also produces octyl acrylate or used as surfactants, etc., which can mainly be used to produce: dioctyl phthalate (DOP), dioctyl oxalate (DOA), trioctyl trimellitic acid (TOTM), other plasticizers, octyl acrylate, surfactants, moisturizing oil additives, mining, diesel fuel additives, solvents and dispensing, rust inhibitor esters, and other chemicals. Octanol itself is a useful solvent, defoamer, dispersant, lubricant, its series of products are mainly plasticizers such as dioctyl phthalate and octyl acrylate. Dioctyl phthalate produced from octanol is the main plasticizer of PVC, and the consumption of PVC accounts for about 95% of its total consumption. Solvents for dyes, resins and oils. Organic synthesis. Plasticizer. Defoaming agent. Fabric mercerization. |
| Production method | 1. The carbonyl synthesis method uses propylene and synthesis gas as raw materials to generate butyraldehyde through the carbonyl synthesis reaction, and the two molecules of butyraldehyde are condensed and dehydrated to obtain 2-ethyl (-2-) hexenal, and then hydrogenated to obtain 2-ethyl (-1-) hexanol. 2. The acetaldehyde condensation method uses acetaldehyde to synthesize butanol aldehyde, dehydration to obtain crotonaldehyde, hydrogenation to obtain n-butyraldehyde, and then two molecules of n-butyraldehyde are condensed and dehydrated to obtain 2-ethyl (-2-) hexenal, and then hydrogenated to obtain 2-ethyl (-1-) hexanol. Synthesis of butanol aldehyde from acetaldehyde, dehydration to obtain crotonaldehyde, hydrogenation to obtain n-butyraldehyde, condensation and dehydration to obtain 2-ethyl-2-hexenal, and then hydrogenation to obtain. |
| category | flammable liquid |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 3730 mg/kg; Oral-mouse LD50: 2500 mg/kg |
| stimulation data | skin-rabbit 500 mg/24 hours moderate; Eye-rabbit 20 mg/24 hours moderate |
| Explosive hazard characteristics | Explosive when mixed with air |
| flammability hazard characteristics | combustible in case of open flame, high temperature and strong oxidant; Combustion emission stimulates smoke |
| storage and transportation characteristics | complete packaging, light and light; warehouse ventilation, away from open flames, high temperature, separate storage from oxidant |
| fire extinguishing agent | foam, carbon dioxide, dry powder |
| auto-ignition temperature | 550 °F |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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Raw Materials for 2-Ethylhexanol
Downstream Products for 2-Ethylhexanol