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| HS Code | 441524 |
| Iupac Name | 2-Ethylhexan-1-ol |
| Common Name | 2-Ethylhexanol |
| Synonym | 2-EH |
| Chemical Formula | C8H18O |
| Molecular Weight | 130.23 g/mol |
| Cas Registry Number | 104-76-7 |
| Ec Number | 203-234-3 |
| Appearance | Colorless liquid |
| Odor | Mild alcoholic odor |
| Boiling Point | 184.6 °C |
| Melting Point | -76 °C |
| Density | 0.832 g/cm³ at 20 °C |
| Vapor Pressure | 0.03 kPa at 20 °C |
| Flash Point | 73 °C closed cup |
| Autoignition Temperature | 245 °C |
| Solubility In Water | 1.1 g/L at 20 °C |
| Logp | 2.9 |
| Refractive Index | 1.431 at 20 °C |
| Viscosity | 6.2 mPa·s at 20 °C |
As an accredited 2-Ethylhexanol 2-EH factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
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At a phthalate esterification unit, 2-ethylhexanol and phthalic anhydride are combined in a glass-lined stirred reactor fitted with a packed rectification column, a water-cooled total condenser, and a decanter for the water–2-ethylhexanol heteroazeotrope. The esterification charge is maintained at a molar ratio of 2.20–2.60 mol 2-ethylhexanol per mole of phthalic anhydride, equivalent to 1.94–2.28 kg/kg of phthalic anhydride, to drive equilibrium toward di-2-ethylhexyl phthalate while retaining sufficient alcohol reflux for water removal. The reactor is heated to 150–220 °C and held under reduced pressure in the final stage, typically 50–200 mbar, using steam ejectors or liquid-ring vacuum pumps. Tetrabutyl titanate or sulfuric acid is dosed as catalyst; production plants adjust catalyst loadings until the acid value is below 0.07 mg KOH/g by DIN EN ISO 2114:2000. Column flooding or decanter temperatures below 90 °C cause water retention in the reactor, and acid value excursions above 0.10 mg KOH/g have been recorded on steam-heated batch lines with undersized overhead condensers. Neutralization with dilute sodium carbonate solution, water washing, and diatomaceous earth filtration remove catalyst residues before flash evaporation and nitrogen stripping reduce moisture below 0.1% by weight. In flexible PVC compounding, the resulting DEHP is added at 30–50 phr for calendered flooring, 40–60 phr for extruded profiles and tubing, and 50–70 phr for wire and cable jackets. The dry blend is mixed in a hot-cool high-speed mixer at 110–140 °C, then melt-compounded in a counter-rotating twin-screw extruder with an L/D ratio of 25:1–30:1 and barrel temperatures of 160–190 °C. Terminal finished products include flexible PVC cable sheathing, tarpaulins, flexible hoses, coated textiles, and vinyl flooring. Export compliance screens DEHP-containing articles against EU RoHS Directive 2011/65/EU Annex II as amended by (EU) 2015/863, with DEHP restricted to 0.1% by weight in homogeneous materials, and against REACH Annex XVII entry 51 for toys and childcare articles. Where OEM purchase specifications exclude ortho-phthalate plasticizers, DOTP is selected as the replacement, and the operating window changes because terephthalic acid is more difficult to suspend than molten phthalic anhydride.
Terephthalate plasticizer production is less tolerant of residual moisture than ortho-phthalate esterification because purified terephthalic acid is a high-melting solid that is suspended in 2-ethylhexanol rather than melted. The feed ratio is set at 2.20–2.80 mol 2-ethylhexanol per mole of PTA, equivalent to 1.72–2.20 kg/kg, so that water of reaction can be removed without excessive alcohol carry-over. Esterification is carried out at 190–245 °C with tetrabutyl titanate or titanium tetraisopropoxide as catalyst; published data for specific plant-scale catalyst loadings is limited, but the working range is typically 0.05–0.15 wt% based on PTA charge. Water entering with wet PTA above 0.5% hydrolyzes the titanium catalyst to dispersed oxide fines, causing turbidity and raising the finished ester acid value. The reactor train includes a packed column and a heated decanter; final esterification is driven under vacuum at 20–50 mbar, followed by steam stripping at 160–190 °C and neutralization with sodium carbonate. Acid value after filtration is normally held below 0.05 mg KOH/g by DIN EN ISO 2114:2000, and moisture is below 0.05%. In PVC compounding, DOTP is added at 40–70 phr in automotive cable insulation, 35–50 phr in automotive interior films and synthetic leather, and 30–50 phr in general flexible PVC extrusion. High-intensity mixing at 110–120 °C is followed by twin-screw compounding at 160–185 °C; low-shear melt pumps and screen changers are used on cable extrusion lines to reduce gel counts. Finished articles include automotive harness insulation, instrument panel skins, vinyl flooring, and sealant strips. Automotive OEM standards impose fogging limits according to DIN 75201-A and VOC limits according to VDA 277; although DOTP is not listed in RoHS Directive 2011/65/EU Annex II as a restricted phthalate, substance-level compliance under REACH Annex XVII and Article 33 communication must be verified for the final article.
A seeded semi-continuous emulsion polymerization train receiving 2-ethylhexyl acrylate as the dominant low-glass-transition monomer operates with a monomer mixture in which 2-EHA constitutes 80–95 wt% of total monomer, butyl acrylate 0–10 wt%, methyl methacrylate 0–5 wt%, and acrylic acid or methacrylic acid 1–4 wt%. The chain transfer agent tert-dodecyl mercaptan is added at 0.02–0.20 phr to control molecular weight and peel-force build; anionic surfactant at 0.8–2.0 phr and nonionic surfactant at 0.2–0.8 phr stabilize the pre-emulsion. The initial reactor charge is 10% of the total pre-emulsion and is polymerized at 75–85 °C under a nitrogen blanket with ammonium persulfate at 0.2–0.5 phr. Remaining pre-emulsion is fed over 3–5 h through a dosing pump into a stirred glass-lined or stainless-steel reactor; high-shear rotors are avoided during feed addition because shear-induced coagulum increases when the polymer fraction exceeds 45%. After feed completion, the latex is held for 1–2 h and chased with tert-butyl hydroperoxide and sodium metabisulfite at 50–60 °C to reduce residual 2-EHA. Plant lines producing pressure-sensitive labels frequently target residual 2-EHA below 100 mg/kg, while medical adhesive lines target 50 mg/kg or lower. The finished latex may be direct-coated or transfer-coated onto silicone release liners and face stocks. Terminal products include pressure-sensitive tapes, graphic films, label stock, and medical wound dressings. Peel adhesion is measured by ASTM D3330/D3330M-04 or PSTC-101; food-contact pressure-sensitive adhesives are evaluated for compliance with 21 CFR 175.125, and medical skin-contact adhesives are screened under ISO 10993-5 for cytotoxicity and ISO 10993-10 for irritation. Process deviations in seed particle size distribution produce batch-to-batch viscosity drift and peel force variation; production-scale dialing of pre-emulsion feed rate changes latex viscosity and shear resistance more than monomer ratio alone.
2-Ethylhexyl nitrate is produced by mixed acid nitration of 2-ethylhexanol in a continuous jacketed tubular reactor equipped with static-mixer elements and refrigerated brine coolant. The reaction is maintained below 30 °C because nitrate ester decomposition accelerates with temperature; the organic layer is then separated, washed with dilute caustic and demineralized water, and dried under vacuum at 40 °C or lower. The resulting product is handled as a low-viscosity liquid and is not blended into diesel fuel until the final terminal dosing step. In diesel formulation, 2-EHN is added at 500–1,500 mg/kg (0.05–0.15 wt%), with the selection within this range determined by the base fuel natural cetane and the target engine ignition delay. The cetane number gain is measured by ASTM D613, and for tighter refinery monitoring the derived cetane number is checked by ASTM D6890. Commercial compounds are formulated as additive packages rather than neat 2-EHN, and the product is injected after filtration and before final product certification; terminal lines use positive-displacement dosing pumps with internal relief set at low pressure, static mixers, and sample points for EN 590 conformance. Above 1,500 mg/kg, incremental cetane response decreases in most middle-distillate fuels, and bulk fuel properties such as storage stability can be affected by nitrate ester decomposition products. Storage vessels are designed for product temperatures below 50 °C; heat tracing, immersion heaters, and tight-clearance centrifugal pumps can create hot spots that darken the product and release nitrogen oxides. Terminal finished fuels include automotive diesel conforming to EN 590, marine gas oil, and off-road diesel. Published data for exact cetane response curves vary with fuel aromatic content, sulfur level, and paraffin distribution; plant evaluation is therefore run as a dose-response matrix before fixed dosing is established.
Di-2-ethylhexyl sebacate and di-2-ethylhexyl adipate are produced in multi-batch esterification vessels by reacting sebacic acid or adipic acid with 2-ethylhexanol in a molar ratio of 2.00–2.40 mol 2-EH per mole of dibasic acid. On a mass basis, the alcohol charge is 1.29–1.55 kg/kg of sebacic acid or 1.78–2.14 kg/kg of adipic acid. Esterification is run at 170–230 °C under nitrogen with a xylene or toluene azeotrope water-removal loop, then finished under vacuum below 20 mbar to strip excess alcohol. Titanate or stannous oxalate catalysts are used; after neutralization and clay filtration, the diester is steam-stripped and dried to moisture below 100 mg/kg for lubricant applications. The resulting diesters are combined with antioxidant, antiwear, and corrosion-inhibitor packages in finished lubricant formulations; ester content is typically 10–40 wt% in synthetic compressor oils and 5–20 wt% in metalworking fluid concentrates. Viscosity data are reported according to ASTM D7042 for dynamic viscosity and ASTM D2270 for viscosity index; hydraulic fluid formulations are classified under ISO 6743-4 and may be tested for rust inhibition according to ASTM D665. Terminal products include polyol-ester refrigeration compressor lubricants, synthetic hydraulic fluids, and soluble metal cutting fluids. For refrigerant compressor applications, water content above 100 mg/kg or acid-value drift above 0.1 mg KOH/g during service accelerates hydrolysis of the ester basestock, especially in the presence of strong acid contaminants; ester basestock blending equipment is therefore dedicated and purged with nitrogen.
2-Ethylhexyl palmitate is produced by direct esterification of palmitic acid with 2-ethylhexanol at a molar ratio of fatty acid to alcohol of 1:1.10–1.30, corresponding to 0.56–0.66 kg 2-EH per kilogram of palmitic acid. The reaction is run at 180–220 °C under inert nitrogen with p-toluenesulfonic acid or stannous oxalate as catalyst and a vacuum of 20–40 mbar in the final hold to shift equilibrium. After neutralization with sodium carbonate, adsorption bleaching with activated clay, and steam deodorization at 140–160 °C, the ester is filtered to an acid value below 2 mg KOH/g and residual 2-EH below 50 mg/kg for low odor. In finished cosmetic formulations, 2-ethylhexyl palmitate is incorporated at 1–10 wt% in leave-on skin creams, 2–8 wt% in sunscreen emulsions, and 1–3 wt% in color cosmetics such as foundations and lip products. The ester is added during the oil phase before high-shear homogenization at 3,000–5,000 rpm, with emulsion pH buffered to 5.0–6.5 to reduce ester hydrolysis. Finished products include moisturizers, sun care lotions, tinted lip balms, and anhydrous makeup. Compliance is assessed under EC 1223/2009 for cosmetic products and manufacturing is controlled under ISO 22716; product safety reports include residual alcohol and acid value data. Long-term storage at temperatures above 35 °C or in unlined steel drums can raise acid value and develop odor; bulk storage vessels should be stainless steel or lined carbon steel with closed-loop nitrogen blanketing.
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2-Ethylhexanol 2-EH is a primary branched oxo alcohol with CAS Registry Number 104-76-7, EINECS number 203-234-3, molecular formula C8H18O, and molar mass 130.23 g/mol. Commercial production proceeds through liquid-phase rhodium-catalyzed hydroformylation of propylene to n-butyraldehyde, alkali-catalyzed aldol condensation to 2-ethylhex-2-enal, and hydrogenation over fixed-bed copper or nickel catalysts. The product is supplied as a clear, high-boiling liquid with a characteristic mild alcohol odor. Industrial supply is commonly segregated into standard 2-EH, high-purity 2-EH, and reduced-carbonyl 2-EH grades. Reduced-carbonyl material is specified for continuous esterification lines where aldehyde content above 0.05 wt% can poison titanium-based esterification catalysts or introduce color bodies into plasticizer esters. Standard 2-EH is used for bulk DOP, DOTP, and 2-ethylhexyl acrylate production; high-purity material is reserved for monomer-grade acrylate synthesis and lubricant ester applications where residual catalyst poisons and color precursors must be minimized.
Table 1 lists the specification envelope used for high-purity 2-EH in bulk transfer. Density and viscosity permit unheated transfer in temperate climates, but cold-weather terminals often apply low-pressure steam tracing to maintain storage above 10°C, because viscosity rises as temperature approaches the pour point. Water ingress is a primary specification concern because dissolved water consumes titanium tetrabutoxide and tetra-2-ethylhexyl titanate catalysts in direct esterification, reducing reaction rate and increasing acid number of the crude ester before neutralization.
| Property | Typical specification | Test method |
|---|---|---|
| 2-EH purity | ≥99.5 wt% | ASTM D5008 |
| Acidity as acetic acid | ≤0.01 wt% | ASTM D1613 |
| Water content | ≤0.10 wt% | ASTM E203 |
| Color | ≤10 Pt-Co | ASTM D1209 |
| Specific gravity at 20/20°C | 0.832–0.835 | ASTM D4052 |
| Distillation range at 101.3 kPa | 182–186°C | ASTM D1078 |
| Refractive index nD at 20°C | 1.431–1.433 | ASTM D1218 |
| Hydroxyl number | 429–431 mg KOH/g | ASTM D1957 |
The solubility of water in 2-EH is limited, but even 0.10 wt% water can hydrolyze ester product under acid catalysis and shift equilibrium. Acid number is controlled because residual acidity accelerates downstream ester darkening and increases neutralization demand. Carbonyl content is regulated because unsaturated aldehyde can undergo aldol condensation in the esterification reactor and generate high-boiling color bodies. The narrow distillation range reduces heavy alcohol oligomers that would otherwise increase plasticizer haze. Viscosity at 20°C is approximately 9.8 mPa·s; density at 20°C is approximately 0.8337 g/cm³. The closed-cup flash point is reported near 73°C, which places 2-EH within combustible liquid storage requirements.
2-EH is a primary alcohol with a C2 branching point. This structural feature distinguishes it from linear 1-octanol and from secondary 2-octanol. In direct esterification with phthalic anhydride, 2-EH reacts at the primary hydroxyl site with faster conversion than 2-octanol, which is sterically hindered and forms esters with lower thermal stability. Branching at the C2 position reduces the pour point of derived esters and improves low-temperature flexibility of PVC compounds, but slightly increases plasticizer volatility relative to linear octyl esters. Linear 1-octanol yields adipate and phthalate esters with lower viscosity and higher oxidative stability, but its plasticizers show poorer low-temperature flex and higher melting point. Isononanol, a C9 branched oxo alcohol, generates esters with higher molecular weight and lower volatility, but the additional side-chain branching slows esterification and raises plasticizer melt viscosity.
In PVC, DOP from 2-EH has a molecular weight of approximately 390.56 g/mol; diisononyl phthalate from isononanol has a molecular weight of approximately 418.61 g/mol. This difference corresponds to lower plasticizer loss under ASTM D1203 accelerated volatility conditions for DINP, but higher fusion temperature and dry-blend absorption time in planetary mixers. DOTP derived from 2-EH is selected where ortho-phthalate restrictions apply under European Union Regulation 1907/2006, Annex XVII entry 51; it provides comparable plasticizing efficiency to DOP but requires slightly higher processing temperatures. Published data for direct substitution ratios in high-speed compounding lines indicate that DOTP may require an increase in mixer set point of 5–10°C to reach equivalent dry blend absorption.
Plant-scale hydroformylation for 2-EH production operates with propylene feed purified to remove sulfur and oxygen compounds that poison the rhodium-triphenylphosphine catalyst. The n-butyraldehyde to iso-butyraldehyde ratio is held above 10:1 by maintaining excess triphenylphosphine and low reactor temperature; iso-butyraldehyde is separated and diverted to neopentyl glycol or other oxo derivatives. The aldol condensation loop uses diluted sodium hydroxide as a homogeneous catalyst. The aldehyde mixture and aqueous caustic are contacted in a stirred reactor with external cooling because the reaction is exothermic and self-condensation to high-molecular-weight aldol resins occurs above 130°C. Plant data indicate that caustic carryover into the hydrogenation section raises acid number of the crude alcohol and accelerates nickel catalyst deactivation; coalescers and water washes are therefore maintained after the aldol separator.
Hydrogenation of 2-ethylhexenal is carried out in a fixed-bed trickle reactor over copper-zinc or nickel-on-silica catalysts. Liquid hourly space velocity and hydrogen-to-aldehyde ratio are balanced to keep catalyst bed temperature below 230°C, above which dehydrogenation and aldol oligomerization increase. Product leaving the hydrogenation section is distilled in a two-column sequence; light ends are withdrawn overhead and heavy aldol dimers are removed as bottoms. The final product column is operated under reduced pressure to limit thermal degradation of the alcohol; a reboiler temperature above 175°C is avoided to suppress ester formation from residual acid. Reactor pressure drop, water content in hydrogen feed, and sodium leakage from the aldol section are the primary production bottlenecks monitored by plant laboratories.
In PVC compounding, 2-EH-derived DOTP and DOP are added at 40–70 phr in flexible formulations, depending on Shore A hardness and application. Dry-blending in a high-speed mixer typically proceeds until the plasticizer is absorbed into the PVC grain at 120–160°C; branched 2-EH esters penetrate faster than isononanol esters of equivalent molecular weight. Film and sheet lines use 2-EH plasticizers because the balance between solvation and permanence gives a useful processing window, but migration under ASTM D1203 becomes limiting when plasticizer content exceeds 80 phr in high-humidity service. Tensile properties of fused PVC measured according to ASTM D638 show lower tensile strength and higher elongation at break as plasticizer concentration increases; low-temperature flexibility measured according to ASTM D1043 improves as the branched alkyl chain disrupts crystallites. In automotive interior compounds, 2-EH-derived TOTM is used where lower volatility and improved heat aging are required; the trimellitate ester has a molecular weight of approximately 546.78 g/mol and is processed at higher line temperatures than DOP.
2-Ethylhexyl acrylate is produced by direct esterification of 2-EH with acrylic acid using methanesulfonic acid or sulfonic acid resin catalysis. The reaction is highly exothermic and polymerization-prone; hydroquinone monomethyl ether or phenothiazine inhibitor is fed with the acrylic acid stream. Esterification water is removed by azeotropic distillation with cyclohexane or toluene. The crude ester is washed with caustic to remove unreacted acid and then vacuum-stripped to a residual 2-EH content below 0.05 wt%. In emulsion polymerization, 2-EHA imparts a glass transition temperature below -50°C to the homopolymer, but commercial pressure-sensitive adhesives typically copolymerize 2-EHA with butyl acrylate, methyl methacrylate, or acrylic acid to balance tack, cohesion, and shear. Reactor systems for 2-EHA emulsion polymerization use stainless steel jackets and monomer pre-emulsion feed because the monomer has water solubility below 0.01 wt% and requires surfactant stabilization. Residual alcohol in the monomer acts as a chain-transfer agent and broadens molecular weight distribution; manufacturer specifications therefore limit alcohol content in monomer-grade 2-EH.
2-EH is combustible; commercial safety data sheets list a closed-cup flash point near 73°C and an autoignition temperature near 231°C. Storage tanks are fabricated from carbon steel or 304L stainless steel. Copper and copper-bearing alloys are excluded from long-term product contact because trace copper catalyzes color formation and aldehyde condensation. Nitrogen blanketing at 0.005–0.020 MPa gauge is applied to fixed-roof tanks to exclude oxygen. Peroxide formation is slow but can occur during prolonged oxygen exposure under ultraviolet light; transfer lines and pumps are grounded and inerted. Water accumulation in tank heels is drained routinely because water accelerates acid formation through ester hydrolysis and can support microbial growth at the water-hydrocarbon interface. 2-EH reacts with strong oxidizing agents and acid chlorides; blending with isocyanates or anhydrides is avoided unless reaction is intended. Harmonized classification under Regulation (EC) No 1272/2008 includes H315, H319, and H335. Spill control includes alcohol-resistant foam systems because 2-EH floats on water but is not readily miscible; the theoretical chemical oxygen demand of the alcohol is approximately 2.95 g O₂/g. Biological treatment of wastewater containing 2-EH requires acclimated biomass and sufficient dissolved oxygen to avoid foaming and sludge bulking.
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