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1,2,3,4-Tetrahydronaphthalene is a clear, colorless to pale yellow liquid hydrocarbon derived from naphthalene by partial hydrogenation, combining aromatic character with enhanced chemical stability.
1,2,3,4-Tetrahydronaphthalene is valued for its high solvency power, high boiling point, and hydrogen-donor capability, making it useful in solvents, heat transfer fluids, coal liquefaction, petroleum refining, and as a chemical intermediate.
1,2,3,4-Tetrahydronaphthalene dissolves a wide range of natural and synthetic resins, waxes, oils, greases, and polymers, showing superior performance in dissolving high-molecular-weight materials compared to many other solvents.
CAS Number: 119-64-2
EC Number: 204-340-2
Chemical Formula: C10H12
Molecular Weight: 132.20 g/mol
Synonyms: 1,2,3,4-Tetrahydronaphthalene, TETRALIN, 119-64-2, Benzocyclohexane, Tetrahydronaphthalene, Bacticin, Tetraline, Tetranap, Naphthalene, 1,2,3,4-tetrahydro-, Tetralina, Naphthalene, tetrahydro-, Naphthalene 1,2,3,4-tetrahydride, tetralene, UNII-FT6XMI58YQ, NSC 77451, (C4-C5) Alkyltetrahydronaphthalenes, FT6XMI58YQ, Naphthalene, 1,2,3,4-tetrahydro-, C1-4-alkyl derivs., CHEBI:35008, 1,2,3,4-tetrahydro-naphthalene, MFCD00001733, DSSTox_CID_6118, DSSTox_RID_78023, DSSTox_GSID_26118, 68412-24-8, Tetralina [Polish], Caswell No. 842A, CAS-119-64-2, CCRIS 3564, HSDB 127, delta(sup 5,7,9)-naphthantriene, EINECS 204-340-2, 1,2,3,4-Tetrahydronaphthalene, reagent grade, >=97%, EPA Pesticide Chemical Code 055901, AI3-01257, Tetralin solvent, EINECS 270-178-4, bmse000530, EC 204-340-2, NCIOpen2_000650, 1,3,4-Tetrahydronaphthalene, 1,2,3,4-tetrahydronapthalene, 5,6,7,8-tetrahydronaphthalene, CHEMBL1575635, DTXSID1026118, Naphthalene 1,3,4-tetrahydride, WLN: L66 & TJ, 1,2,3,4 Tetrahyclronaphthalene, .delta.(5,7,9)-Naphthantriene, .delta.(sup 5,9)-Naphthantriene, Naphthalene-1,2,3,4-tetrahydride, NSC77451, ZINC8437660, Tox21_201793, Tox21_303325, NSC-77451, STL264224, .delta.(sup 5,7,9)-Naphthantriene, AKOS000121383, LS40429, MCULE-8327072794, NCGC00091744-01, NCGC00091744-02, NCGC00256948-01, NCGC00259342-01, I899, FT-0654145, T0107, T0713, 1,2,3,4-tetrahydronaphthalene, Tetralin, THN, 1,2,3,4-Tetrahydronaphthalene, anhydrous, 99%, Q420416, 1,2,3,4-Tetrahydronaphthalene, analytical standard, W-108503, 1,2,3,4-Tetrahydronaphthalene, ReagentPlus(R), 99%, F1908-0164, 1,2,3,4-Tetrahydronaphthalene, Vetec(TM) reagent grade, 98%, 1,2,3,4-Tétrahydronaphtalène [French] [ACD/IUPAC Name], 1,2,3,4-Tetrahydronaphthalen, 1,2,3,4-Tetrahydronaphthalene [ACD/IUPAC Name], 1,2,3,4-Tetrahydronaphthalin [German] [ACD/IUPAC Name], 119-64-2 [RN], 1446407 [Beilstein], 204-340-2 [EINECS], FT6XMI58YQ, MFCD00001733 [MDL number], Naphthalene, 1,2,3,4-tetrahydro- [ACD/Index Name], tetrahydronaphthalene, Tetralin [Wiki], Tetralin(R) solvent, Tetralina [Polish], Tetraline [Dutch], Tétraline [French], 四氢化萘 [Chinese], [119-64-2] [RN], 1,2,3, 4-Tetrahydronaphthalene, 1,2,3,4-Tetrahydronaphthalene 10 µg/mL in Methanol, 1,2,3,4-tetrahydronaphthalene(tetralin), 1,2,3,4-tetrahydronaphthalene, Tetralin, THN, 1,2,3,4-Tetrahydronaphthalene;Tetralin, 1,2,3,4-TETRHYDRONAPHTHALENE, 204-340-2MFCD00001733, 270-178-4 [EINECS], 68412-24-8 [RN], benzocyclohexane, C095210, EINECS 204-340-2, EINECS 270-178-4, naphthalene 1,2,3,4-tetrahydride, NAPHTHALENE, TETRAHYDRO-, Naphthalene-1,2,3,4-tetrahydride, pWLN: L66 & TJ, teteralin, tetralene, Tetralin(TM) solvent, Tetralin?, Tetralina, Tetralina [Polish], Tetraline, Tetrana, TETRANAP, THN, UNII:FT6XMI58YQ, UNII-FT6XMI58YQ, WLN: L66 & TJ, δ(5,7,9)-Naphthantriene, δ(sup 5,7,9)-naphthantriene, δ(sup 5,7,9)-Naphthantriene, 2'-acetonaphthone, 5',6', 7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-, 2'-acetonaphthone, 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-, acetyl hexamethyl tetralin, 6-acetyl-1,1,2,4,4,7-hexamethyl tetralin, 6-acetyl-1,1,2,4,4,7-hexamethyl-1,2,3,4-tetrahydronaphthalene, 6-acetyl-1,1,2,4,4,7-hexamethyltetralin, 7-acetyl-1,1,3,4,4,6-hexamethyl tetrahydronaphthalene, 7-acetyl-1,1,3,4,4,6-hexamethyl tetralin, 7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene, 7-acetyl-1,1,3,4,4,6-hexamethyltetrahydronaphthalene, 7-acetyl-1,1,3,4,4,6-hexamethyltetralin, 6-acetyl-1,2,3,4-tetrahydro-1,1,2,4,4,7-hexamethyl naphthalene, 6-acetyl-1,2,3,4-tetrahydro-1,1,2,4,4,7-hexamethylnaphthalene, AHMT, ethanone, 1- (5,6,7,8-tetrahydro-3,5,5,6,8, 8-hexamethyl-2-naphthalenyl)-, ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)-, fixolide, 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethanone, 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone, 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone, 1-(3,5,5,6,8,8-hexamethyl-6,7-dihydronaphthalen-2-yl)ethanone, INCI acetyl hexamethyl tetralin, muscofix (A.C.S. International), musk tetralin, musk tonalid, naphthalene, 7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydro-, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)ethan- one, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl) ethan-1-one, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl)ethan-1-one, 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2'-acetonaphthone, tetralide, tonalid (PFW), tonalid II (PFW), tonalide (PFW)
1,2,3,4-Tetrahydronaphthalene is a clear, colorless to pale yellow liquid hydrocarbon belonging to the class of aromatic hydrogenated compounds.
Structurally, 1,2,3,4-Tetrahydronaphthalene is derived from naphthalene by the partial hydrogenation of one of its aromatic rings, resulting in a bicyclic system with one saturated cyclohexane ring fused to an aromatic benzene ring.
1,2,3,4-Tetrahydronaphthalene has a mild aromatic odor, a boiling point of approximately 207 °C, and is insoluble in water but miscible with most organic solvents.
1,2,3,4-Tetrahydronaphthalene is valued for its high solvency power, chemical stability, and low volatility relative to lighter aromatics.
Industrially, 1,2,3,4-Tetrahydronaphthalene is used as a solvent for resins, paints, oils, and waxes; as a heat transfer fluid; as a hydrogen donor in coal liquefaction and petroleum refining; and as an intermediate in the production of certain chemicals such as 1-naphthol and phthalic anhydride.
1,2,3,4-Tetrahydronaphthalene is also employed in laboratory research as a solvent and hydrogenation medium.
While 1,2,3,4-Tetrahydronaphthalene is relatively stable under normal conditions, prolonged exposure to air and light can cause oxidation to form naphthalene and other byproducts.
1,2,3,4-Tetrahydronaphthalene can cause irritation to the skin, eyes, and respiratory tract, and prolonged or high-level exposure may affect the central nervous system, so handling requires proper ventilation and protective measures.
1,2,3,4-Tetrahydronaphthalene is a hydrocarbon having the chemical formula C10H12.
1,2,3,4-Tetrahydronaphthalene is a partially hydrogenated derivative of naphthalene.
1,2,3,4-Tetrahydronaphthalene is a colorless liquid that is used as a hydrogen-donor solvent.
1,2,3,4-Tetrahydronaphthalene is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 to < 10 000 tonnes per annum.
1,2,3,4-Tetrahydronaphthalene is used in formulation or re-packing, at industrial sites and in manufacturing.
1,2,3,4-Tetrahydronaphthalene is a hydrocarbon having the chemical formula C10H12.
1,2,3,4-Tetrahydronaphthalene is similar to the naphthalene chemical structure except that one ring is saturated.
1,2,3,4-Tetrahydronaphthalene can be synthesized in a Bergman cyclization.
In a classic named reaction called the Darzens 1,2,3,4-Tetrahydronaphthalene synthesis derivatives can be prepared by intramolecular ring-closing reaction of an 1-aryl-4-pentene with concentrated sulfuric acid, or simply through the hydrogenation of naphthalene in the presence of a platinum catalyst.
1,2,3,4-Tetrahydronaphthalene is a hydrocarbon having the chemical formula C10H12.
1,2,3,4-Tetrahydronaphthalene is similar to the naphthalene chemical structure except that one ring is saturated.
1,2,3,4-Tetrahydronaphthalene is used as a solvent.
1,2,3,4-Tetrahydronaphthalene is also used for the laboratory synthesis of dry HBr gas.
1,2,3,4-Tetrahydronaphthalenes are found in many bioactive molecules and the potent biological properties of compounds possessing a 1,2,3,4-Tetrahydronaphthalene and an oxindole hybrid core are easy to imagine.
However, to our surprise, very few synthetic methods have been reported for 1,2,3,4-Tetrahydronaphthalene-fused spirooxindoles, especially for a spirooxindole unit at the 2-position of the 1,2,3,4-Tetrahydronaphthalene core.
1,2,3,4-Tetrahydronaphthalene is a clear, colorless to pale yellow liquid hydrocarbon that belongs to the class of partially hydrogenated aromatic compounds.
1,2,3,4-Tetrahydronaphthalene is structurally derived from naphthalene by the selective hydrogenation of one of its benzene rings, producing a bicyclic system composed of one saturated cyclohexane ring fused to an unsaturated benzene ring.
This unique structure gives 1,2,3,4-Tetrahydronaphthalene a combination of aromatic character and enhanced chemical stability compared to fully aromatic hydrocarbons.
1,2,3,4-Tetrahydronaphthalene has a mild, slightly sweet aromatic odor, a molecular weight of 132.20 g/mol, a boiling point of around 207 °C, a melting point of −35 °C, and a density of about 0.97 g/cm³ at 20 °C.
1,2,3,4-Tetrahydronaphthalene is insoluble in water but is completely miscible with most organic solvents, including alcohols, ethers, hydrocarbons, and chlorinated solvents, making it a versatile medium in both laboratory and industrial processes.
1,2,3,4-Tetrahydronaphthalene's most notable industrial applications arise from its high solvency power, relatively high boiling point, and ability to act as a hydrogen donor.
1,2,3,4-Tetrahydronaphthalene is widely used as a solvent for resins, paints, greases, waxes, asphalt, and various synthetic polymers.
In the petroleum and coal industries, 1,2,3,4-Tetrahydronaphthalene serves as an effective hydrogen donor in coal liquefaction, hydrocracking, and petroleum refining processes, where it helps stabilize free radicals and prevent coke formation.
1,2,3,4-Tetrahydronaphthalene is also an important intermediate in chemical manufacturing, used in the production of 1-naphthol, 2-naphthol, and phthalic anhydride, as well as in the synthesis of dyes, plasticizers, and certain pharmaceuticals.
In the plastics and rubber industries, 1,2,3,4-Tetrahydronaphthalene is employed as a processing aid and in heat transfer systems due to its thermal stability.
In the laboratory, 1,2,3,4-Tetrahydronaphthalene is valued as a high-boiling, low-volatility solvent for hydrogenation reactions and as a medium for carrying out chemical transformations that require elevated temperatures.
1,2,3,4-Tetrahydronaphthalene has also been used as a model compound for studying hydrogen transfer mechanisms in organic chemistry.
While generally stable under normal handling conditions, 1,2,3,4-Tetrahydronaphthalene can oxidize upon prolonged exposure to air and light, forming naphthalene, peroxides, and other degradation products, some of which may be hazardous.
Therefore, 1,2,3,4-Tetrahydronaphthalene is often stored under inert atmospheres in sealed containers.
1,2,3,4-Tetrahydronaphthalene appears as a light colored liquid.
1,2,3,4-Tetrahydronaphthalene may be irritating to skin, eyes and mucous membranes.
1,2,3,4-Tetrahydronaphthalene is a potent antagonist of bacterial fatty acid synthase, which is the key enzyme in the biosynthesis of fatty acids.
1,2,3,4-Tetrahydronaphthalene has been shown to be effective against wild-type strains and mutant strains of Escherichia coli, Salmonella typhimurium, and Staphylococcus aureus.
1,2,3,4-Tetrahydronaphthalene has also been shown to be an antihypertensive compound with a kinetic mechanism that is not yet understood.
The chemical reactions involved in the synthesis of 1,2,3,4-Tetrahydronaphthalene are most likely due to 1,2,3,4-Tetrahydronaphthalene chiral nature.
1,2,3,4-Tetrahydronaphthalene can also be synthesized by asymmetric synthesis using a surface methodology.
1,2,3,4-Tetrahydronaphthalene has been shown to have no carcinogenic effects in rodent studies.
1,2,3,4-Tetrahydronaphthalene and benzodioxans:
1,2,3,4-Tetrahydronaphthalene (TET), 1,4-benzodioxan (14BZD), and 1,3-benzodioxan (13BZN) are all analogous to the cyclohexene family of molecules and hence have twisted structures with high barriers to planarity.
Because of their low vapor pressures, they have not been studied by far-infrared spectroscopy, but their S0 vibrational data have been obtained using SVLF spectra of the jet-cooled molecules and high-temperature vapor-phase Raman spectra.
Market Overview of 1,2,3,4-Tetrahydronaphthalene:
1,2,3,4-Tetrahydronaphthalene occupies a specialized but steady niche within the global petrochemical and specialty solvent markets.
1,2,3,4-Tetrahydronaphthalene's demand is primarily driven by applications in coal liquefaction, petroleum refining, specialty solvents, and chemical intermediates.
Although 1,2,3,4-Tetrahydronaphthalene’s total global consumption volume is modest compared to bulk aromatics like toluene or xylene, it remains critical in certain high-value industrial processes due to its unique combination of high boiling point, strong solvency power, and hydrogen-donor capability.
Global Production and Supply:
1,2,3,4-Tetrahydronaphthalene is produced mainly through the catalytic hydrogenation of naphthalene using hydrogen gas in the presence of nickel-, palladium-, or platinum-based catalysts.
Major production hubs are located in regions with strong petrochemical infrastructure, particularly China, India, the United States, Western Europe, and Japan.
Supply is closely tied to naphthalene availability, which is obtained from coal tar distillation and petroleum refining.
Demand Trends:
Energy & Fuels Sector:
1,2,3,4-Tetrahydronaphthalene’s largest market historically has been as a hydrogen donor in coal liquefaction and certain refinery processes.
However, this segment has seen fluctuating demand due to shifts toward cleaner energy sources and changing government policies.
Coatings, Resins & Specialty Chemicals:
Steady demand exists for 1,2,3,4-Tetrahydronaphthalene as a high-performance solvent for alkyd resins, phenolic resins, and other specialty polymers used in industrial coatings.
Chemical Intermediates:
Continued use in the production of 1-naphthol, 2-naphthol, and phthalic anhydride supports baseline consumption in dyes, pigments, agrochemicals, and pharmaceuticals.
R&D and Specialty Applications:
Niche but stable demand in research labs and for specialized high-boiling solvent applications.
Market Drivers:
High Solvency Performance:
Preferred for dissolving high-molecular-weight and resinous materials.
Thermal & Chemical Stability:
Enables use in high-temperature industrial and laboratory processes.
Hydrogen-Donor Functionality:
Critical for certain fuel upgrading and synthetic chemistry processes.
Market Challenges:
Environmental and Health Regulations:
Tightening occupational exposure limits and solvent VOC regulations may affect usage in open-process environments.
Energy Sector Transition:
Reduced emphasis on coal-based energy limits growth in liquefaction applications.
Price Sensitivity:
1,2,3,4-Tetrahydronaphthalene is more expensive than many bulk solvents, limiting its use to cases where performance advantages justify cost.
Outlook:
The global 1,2,3,4-Tetrahydronaphthalene market is expected to see modest, stable growth over the next 5–7 years, supported by specialty chemical production, high-performance coatings, and niche industrial applications.
Emerging opportunities exist in advanced battery solvents, heat transfer fluids, and green hydrogenation technologies, but large-scale expansion is unlikely without a significant new industrial driver.
Uses of 1,2,3,4-Tetrahydronaphthalene:
1,2,3,4-Tetrahydronaphthalene is used as degreasing agent.
Solvent for naphthalene, fats, resins, oils, waxes, used instead of turpentine in lacquers, shoe polishes, floor waxes.
The simultaneous cracking of butylbenzene principally produced benzene.
The reaction rate in the ring-opening of 1,2,3,4-Tetrahydronaphthalene was considerably high on strong Brønsted acid sites in the 12-ring of the *BEA zeolite.
The amount of Brønsted acid sites on the *BEA zeolite increased the 1,2,3,4-Tetrahydronaphthalene conversion but did not affect the selectivity to the products.
In 1,2,3,4-Tetrahydronaphthalene conversion, MOR and FAU zeolites formed more methylindane and naphthalene as by-products, respectively.
Methylindane was produced on weak Brønsted acid sites through ring-contraction of 1,2,3,4-Tetrahydronaphthalene, and naphthalene was formed on Lewis acid sites through dehydrogenation.
The influences of the reaction conditions on the catalytic activity in 1,2,3,4-Tetrahydronaphthalene conversion were also investigated.
The contact time increased the conversion, but hardly affected the selectivities to the products.
The total pressure also improved the catalytic activity.
The pressurized hydrogen decreased the selectivity for methylindane, while 1,2,3,4-Tetrahydronaphthalene increased for benzene and 1,2,3,4-Tetrahydronaphthalene derivatives.
At 573 K, the selectivities to benzene and 1,2,3,4-Tetrahydronaphthalene derivatives were high, but the reaction temperature increased the selectivity to the by-products.
1,2,3,4-Tetrahydronaphthalene is used as a hydrogen-donor solvent, for example in coal liquifaction.
1,2,3,4-Tetrahydronaphthalene functions as a source of H2, which is transferred to the coal.
The partially hydrogenated coal is more soluble.
1,2,3,4-Tetrahydronaphthalene has been used in sodium-cooled fast reactors as a secondary coolant to keep sodium seals around pump impellers solidified.
However 1,2,3,4-Tetrahydronaphthalene use has been superseded by NaK.
1,2,3,4-Tetrahydronaphthalene is also used for the laboratory synthesis of HBr:
C10H12 + 4 Br2 → C10H8Br4 + 4 HBr
The facility of this reaction is in part a consequence of the moderated strength of the benzylic C-H bonds.
Uses at industrial sites:
1,2,3,4-Tetrahydronaphthalene is used in the following products: coating products, leather treatment products, polymers and heat transfer fluids.
1,2,3,4-Tetrahydronaphthalene has an industrial use resulting in manufacture of another substance (use of intermediates).
1,2,3,4-Tetrahydronaphthalene is used for the manufacture of: chemicals, textile, leather or fur, rubber products and .
Release to the environment of 1,2,3,4-Tetrahydronaphthalene can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates) and of substances in closed systems with minimal release.
Industrial Applications:
Hydrogen Donor in Coal Liquefaction and Petroleum Refining
1,2,3,4-Tetrahydronaphthalene acts as a hydrogen transfer medium to stabilize reactive species and prevent coke formation during hydrocracking, hydrodesulfurization, and coal hydrogenation.
Solvent:
Dissolves resins, waxes, greases, asphalt, synthetic polymers, and oils in coatings, varnishes, and industrial cleaning formulations.
1,2,3,4-Tetrahydronaphthalene serves as a carrier solvent in specialty coatings and sealants.
Chemical Intermediate:
1,2,3,4-Tetrahydronaphthalene is used in the synthesis of 1-naphthol, 2-naphthol, phthalic anhydride, dyes, and certain pharmaceutical intermediates.
Heat Transfer Fluid:
Employed in closed-loop heating systems due to high boiling point and good thermal stability.
Plastics, Rubber, and Polymer Processing:
1,2,3,4-Tetrahydronaphthalene acts as a swelling agent and processing aid in rubber compounding.
1,2,3,4-Tetrahydronaphthalene is used as a solvent and carrier in plasticizers and polymer modification.
Paints, Coatings, and Inks:
Solvent for alkyd resins, epoxy esters, phenolic resins, and chlorinated rubber coatings.
1,2,3,4-Tetrahydronaphthalene improves film formation and flow characteristics in industrial paints.
Laboratory and Research Uses:
High-boiling solvent for high-temperature organic reactions.
Reaction medium in hydrogenation and dehydrogenation studies.
Model compound in research on hydrogen transfer mechanisms.
Specialty and Niche Applications:
Component in lubricant formulations for high-temperature equipment.
Solvent in metal cleaning and degreasing operations.
Intermediate for agrochemical synthesis.
Benefits of 1,2,3,4-Tetrahydronaphthalene:
Excellent Solvency Power:
1,2,3,4-Tetrahydronaphthalene dissolves a wide range of natural and synthetic resins, waxes, oils, greases, and polymers.
1,2,3,4-Tetrahydronaphthalene shows superior performance in dissolving high-molecular-weight materials compared to many other solvents.
High Boiling Point & Thermal Stability:
1,2,3,4-Tetrahydronaphthalene’s boiling point (~207 °C) allows safe use in high-temperature processes without excessive evaporation losses.
1,2,3,4-Tetrahydronaphthalene maintains chemical stability under prolonged heating, making it ideal for closed-loop heating systems and high-temperature reactions.
Hydrogen-Donor Capability:
1,2,3,4-Tetrahydronaphthalene has the unique ability to transfer hydrogen atoms in chemical reactions, critical in coal liquefaction, hydrocracking, and stabilization of reactive intermediates.
1,2,3,4-Tetrahydronaphthalene reduces coke formation in refinery processes by stabilizing free radicals.
Versatility Across Industries:
1,2,3,4-Tetrahydronaphthalene is used in paints, coatings, petrochemicals, dyes, pharmaceuticals, lubricants, and research laboratories.
1,2,3,4-Tetrahydronaphthalene acts as a solvent, reaction medium, heat transfer fluid, and chemical intermediate.
Enhanced Safety Compared to Lighter Aromatics:
1,2,3,4-Tetrahydronaphthalene’s lower volatility reduces flammability risk and vapor emissions relative to solvents like toluene or xylene.
1,2,3,4-Tetrahydronaphthalene has a mild odor compared to other aromatic hydrocarbons, improving workplace comfort when properly ventilated.
Long-Term Storage Stability:
1,2,3,4-Tetrahydronaphthalene resists polymerization and degradation under normal conditions.
1,2,3,4-Tetrahydronaphthalene can be stored for extended periods if kept away from air and light to prevent oxidation.
Production of 1,2,3,4-Tetrahydronaphthalene:
1,2,3,4-Tetrahydronaphthalene is primarily produced by the catalytic hydrogenation of naphthalene under controlled temperature and pressure conditions.
The process involves adding hydrogen across one of the aromatic rings of naphthalene, resulting in a partially hydrogenated bicyclic structure consisting of one benzene ring and one cyclohexane ring.
Raw Materials:
Naphthalene (C₁₀H₈):
Derived from coal tar distillation or petroleum reformate streams.
Hydrogen gas (H₂):
Supplied from refinery hydrogen plants or industrial gas production.
Process Steps:
Feed Preparation:
High-purity naphthalene is melted or dissolved in a suitable solvent if required.
The feed is filtered to remove impurities that may poison the catalyst.
Catalytic Hydrogenation:
Reaction:
C10H8+2H2→catalystC10H12
Catalysts:
Typically nickel-based (Raney nickel), palladium on carbon (Pd/C), or platinum-based catalysts.
Operating Conditions:
Temperature:
150–250 °C
Pressure:
2–5 MPa (20–50 bar) hydrogen pressure
Reactor Type:
Fixed-bed or trickle-bed hydrogenation reactors
Reaction Control:
Reaction parameters are carefully controlled to prevent over-hydrogenation of both rings, which would yield decalin (decahydronaphthalene) instead of 1,2,3,4-Tetrahydronaphthalene.
Separation and Purification:
The reaction mixture is cooled and depressurized.
Unreacted hydrogen is separated and recycled back to the reactor.
1,2,3,4-Tetrahydronaphthalene is separated from byproducts (e.g., decalin, unreacted naphthalene) by fractional distillation under reduced pressure.
High-purity grades may undergo further purification via vacuum distillation or recrystallization of starting material before hydrogenation.
Alternative Methods:
Partial hydrogenation of naphthalene in supercritical solvents to improve selectivity and catalyst life.
Hydrogen transfer reactions using hydrogen-rich donor solvents such as cyclohexene in the presence of a catalyst (less common industrially).
Key Production Considerations:
Selectivity Control:
Reaction time and hydrogen partial pressure are adjusted to maximize 1,2,3,4-Tetrahydronaphthalene yield and minimize over-hydrogenation to decalin.
Catalyst Management:
Catalyst deactivation by coke or sulfur impurities requires regeneration or replacement.
Safety:
Hydrogen handling at high pressure requires explosion-proof equipment and rigorous process safety controls.
History of 1,2,3,4-Tetrahydronaphthalene:
The history of 1,2,3,4-Tetrahydronaphthalene is closely tied to the development of aromatic hydrogenation chemistry and the broader petrochemical industry.
Late 19th Century – Discovery of Structure:
The parent compound naphthalene was well known by the late 1800s, having been isolated from coal tar in the early 19th century.
Chemists had begun studying 1,2,3,4-Tetrahydronaphthalene's chemical reactivity, including hydrogenation, which laid the groundwork for producing partially hydrogenated derivatives like 1,2,3,4-Tetrahydronaphthalene.
Early 20th Century – Laboratory Synthesis:
In the early 1900s, advances in catalytic hydrogenation, especially with nickel catalysts pioneered by Paul Sabatier (who was awarded the 1912 Nobel Prize in Chemistry), enabled the controlled hydrogenation of naphthalene.
1,2,3,4-Tetrahydronaphthalene was first synthesized in laboratories during this period by selectively adding hydrogen to only one of the two fused aromatic rings, yielding the partially saturated bicyclic structure.
1920s–1930s – Industrial Interest:
With the expansion of the chemical industry between the World Wars, 1,2,3,4-Tetrahydronaphthalene attracted attention as a high-boiling, stable solvent and as a hydrogen donor in coal hydrogenation processes.
The German coal hydrogenation programs, particularly the Bergius process, explored 1,2,3,4-Tetrahydronaphthalene’s ability to stabilize reactive intermediates.
1940s–1950s – Postwar Applications:
During and after World War II, 1,2,3,4-Tetrahydronaphthalene saw wider industrial adoption.
1,2,3,4-Tetrahydronaphthalene's solvency power made it valuable in paint and varnish formulations, resin processing, and metal cleaning.
In the petroleum sector, 1,2,3,4-Tetrahydronaphthalene was increasingly used in refining processes and as a model compound for hydrocarbon reactivity studies.
1960s–1980s – Diversification of Uses:
1,2,3,4-Tetrahydronaphthalene’s role expanded into chemical intermediates production (e.g., 1-naphthol, phthalic anhydride) and heat transfer fluids.
Research during this time further detailed 1,2,3,4-Tetrahydronaphthalene's hydrogen-donor properties, leading to its use in advanced fuel upgrading and synthetic chemistry.
1990s–Present – Specialty Chemical Role:
As environmental regulations tightened and bulk solvent markets shifted toward less hazardous or less persistent chemicals, 1,2,3,4-Tetrahydronaphthalene’s market narrowed to specialized industrial and research uses.
1,2,3,4-Tetrahydronaphthalene remains important in coatings, specialty resins, petrochemical R&D, and certain high-performance applications where its unique combination of high boiling point, chemical stability, and solvency is essential.
Today, 1,2,3,4-Tetrahydronaphthalene is produced globally in moderate volumes, primarily in regions with integrated coal tar, petroleum refining, and petrochemical facilities.
While no longer a high-volume commodity chemical, 1,2,3,4-Tetrahydronaphthalene continues to play a strategic role in niche industrial processes, especially where hydrogen transfer chemistry is required.
Handling and Storage of 1,2,3,4-Tetrahydronaphthalene:
Handling:
Use only in well-ventilated areas or under local exhaust ventilation.
Avoid inhalation of vapors and contact with skin or eyes.
Keep away from heat, sparks, open flames, and hot surfaces.
Ground/bond containers when transferring liquid to prevent static discharge.
Do not eat, drink, or smoke while handling.
Storage:
Store in tightly closed containers in a cool, dry, well-ventilated area away from direct sunlight.
Keep away from oxidizing agents and strong acids.
Store under inert gas (e.g., nitrogen) if prolonged storage is required to prevent oxidation to naphthalene and peroxides.
Recommended storage temperature: Ambient, away from heat sources.
Stability and Reactivity of 1,2,3,4-Tetrahydronaphthalene:
Chemical Stability:
Stable under recommended storage conditions.
Reactivity:
Can slowly oxidize in air to form naphthalene and peroxides.
Conditions to Avoid:
Prolonged exposure to heat, air, and light.
Incompatible Materials:
Strong oxidizers (e.g., nitric acid, chromic acid), strong acids.
Hazardous Decomposition Products:
Carbon oxides (CO, CO₂), naphthalene, phosphorus oxides (trace from impurities), and peroxides under severe conditions.
First Aid Measures of 1,2,3,4-Tetrahydronaphthalene:
Inhalation:
Remove victim to fresh air.
Keep warm and at rest.
Seek medical attention if symptoms persist.
Skin Contact:
Wash immediately with soap and plenty of water.
Remove contaminated clothing.
Seek medical attention if irritation develops.
Eye Contact:
Rinse immediately with plenty of water for at least 15 minutes, lifting eyelids occasionally.
Seek medical attention.
Ingestion:
Do not induce vomiting.
Rinse mouth with water.
Seek immediate medical attention.
Firefighting Measures of 1,2,3,4-Tetrahydronaphthalene:
Suitable Extinguishing Media:
Foam, dry chemical, carbon dioxide, or water spray (do not use water jet directly on the liquid).
Special Hazards:
Combustible liquid; vapors may form explosive mixtures with air.
Special Protective Equipment for Firefighters:
Wear self-contained breathing apparatus (SCBA) and full protective gear.
Additional Advice:
Cool closed containers with water spray to prevent rupture due to heat.
Accidental Release Measures of 1,2,3,4-Tetrahydronaphthalene:
Personal Precautions:
Remove all ignition sources.
Ventilate the area.
Avoid breathing vapors.
Wear appropriate PPE.
Environmental Precautions:
Prevent entry into drains, watercourses, or soil.
Notify authorities if large spills occur.
Spill Cleanup Methods:
Contain spill with inert absorbent (e.g., vermiculite, sand). Place in suitable labeled container for disposal.
Wash spill area thoroughly.
Exposure Controls / Personal Protective Equipment of 1,2,3,4-Tetrahydronaphthalene:
Occupational Exposure Limits:
OSHA PEL (as naphthalene):
10 ppm (TWA)
ACGIH TLV:
10 ppm (TWA), 15 ppm (STEL) — consult regional regulations.
Engineering Controls:
Provide local exhaust ventilation or process enclosure to control vapor levels.
Use explosion-proof equipment in areas with potential vapor release.
Personal Protective Equipment:
Respiratory Protection:
If exposure limits are exceeded, use a NIOSH-approved organic vapor respirator.
Eye Protection:
Safety goggles or face shield.
Skin Protection:
Chemical-resistant gloves (nitrile, neoprene) and protective clothing.
Hygiene Measures:
Wash hands before eating, drinking, or smoking.
Remove contaminated clothing before reuse.
Identifiers of 1,2,3,4-Tetrahydronaphthalene:
CAS Number: 119-64-2
ChEBI: 35008
ChemSpider: 8097
ECHA InfoCard: 100.003.946
KEGG: C14114
PubChem CID: 8404
UNII: FT6XMI58YQ
CompTox Dashboard (EPA): DTXSID1026118
IUPAC Name: 1,2,3,4-tetrahydronaphthalene
Alternative Names: 1,2,3,4-Tetrahydronaphthalene
Molecular Formula: C10H12
Molar Mass: 132.206 g/mol
InChI: InChI=1S/C10H12/c1-2-6-10-8-4-3-7-9(10)5-1/h1-2,5-6H,3-4,7-8H2
InChI Key: CXWXQJXEFPUFDZ-UHFFFAOYSA-N
Chemical Name: 1,2,3,4-Tetrahydronaphthalene
IUPAC Name: 1,2,3,4-Tetrahydronaphthalene
Chemical Formula: C₁₀H₁₂
Molecular Weight: 132.20 g/mol
CAS Number: 119-64-2
EC Number (EINECS): 204-340-2
PubChem CID: 8467
UN Number: UN 3295 (Hydrocarbons, liquid, n.o.s., for transport classification)
HS Code: 290290 (Cyclic hydrocarbons, other)
RTECS Number: QJ0525000
InChI: InChI=1S/C10H12/c1-2-6-10-8-4-3-7-9(10)5-1/h1-2,6,8H,3-5,7H2
InChI Key: ZYUPYZHZLVLOER-UHFFFAOYSA-N
SMILES: C1CCC2=CC=CC=C2C1
Product Code: FT46025
Synonyms: 1,2,3,4-Tetrahydronaphthalene
CAS Number: 119-64-2
Chemical Formula: C10H12
Molecular Weight: 132.20
Appearance: Colourless to pale yellow liquid
Purity (GC): min 95%
CAS Registry Number: 119-64-2
CAS Name: 1,2,3,4-Tetrahydronaphthalene
Trademarks: Tetranap
Molecular Formula: C10H12
Molecular Weight: 132.20
Percent Composition: C 90.85%, H 9.15%
Properties of 1,2,3,4-Tetrahydronaphthalene:
Chemical formula: C10H12
Molar mass: 132.206 g·mol−1
Appearance: colorless liquid with an odor similar to naphthalene
Density: 0.970 g/cm3
Melting point: −35.8 °C (−32.4 °F; 237.3 K)
Boiling point: 206 to 208 °C (403 to 406 °F; 479 to 481 K)
Solubility in water: Insoluble
Viscosity: 2.02 cP at 25 °C
Physical State: Liquid
Storage: Store at room temperature
Melting Point: -35.8° C
Boiling Point: 309° C
Molecular Weight: 132.20
XLogP3: 3.5
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Rotatable Bond Count: 0
Exact Mass: 132.093900383
Monoisotopic Mass: 132.093900383
Topological Polar Surface Area: 0 Ų
Heavy Atom Count: 10
Complexity: 92.6
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Specification of 1,2,3,4-Tetrahydronaphthalene:
Specific Gravity: 0.970 - 0.975
Appearance: Clear to pale yellow oily liquid
Content: 94.0% max
Naphthalene: 2.0% max
Decalin: 1.0% max
Water: 0.1% max
Boiling Point: 205 - 208 C
Melting Point: -36 ~ -35 C
Vapor Density: 4.6
Autoignition: 385 C
Refractive Index: 1.5410 - 1.5411
Flash Point: 77 C
Stability: 1,2,3,4-Tetrahydronaphthalene is stable under normal conditions.
1,2,3,4-Tetrahydronaphthalene is air sensitive.
Product Line: 1,2,3,4-Tetrahydronaphthalene
Density: 0.973 g/mL (at 25°C)
Linear Formula: C10H12
Percent Purity: ≥99.5% (GC)
Grade: Analytical Standard
Physical Form: Neat
Names of 1,2,3,4-Tetrahydronaphthalene:
CAS names:
Naphthalene
1,2,3,4-tetrahydro-
Regulatory process names:
1,2,3,4-tetrahydronaphthalene
Translated names:
1,2,3,4-tetrahidronaftalen (hr)
1,2,3,4-tetrahidronaftalen (sl)
1,2,3,4-tetrahidronaftalenas (lt)
1,2,3,4-tetrahidronaftaleno (es)
1,2,3,4-tetrahidronaftaleno (pt)
1,2,3,4-tetrahidronaftalin (hu)
1,2,3,4-tetrahidronaftalina (ro)
1,2,3,4-tetrahidronaftalīns (lv)
1,2,3,4-tetrahydronaftaleen (nl)
1,2,3,4-tetrahydronaftaleeni (fi)
1,2,3,4-tetrahydronaftalen (cs)
1,2,3,4-tetrahydronaftalen (no)
1,2,3,4-tetrahydronaftalen (pl)
1,2,3,4-tetrahydronaftalen (sv)
1,2,3,4-tetrahydronaftalén (sk)
1,2,3,4-tetrahydronaphtalen (da)
1,2,3,4-Tetrahydronaphthalin (de)
1,2,3,4-Tetrahüdronaftaleen (et)
1,2,3,4-tetraidronaftalene (it)
1,2,3,4-tétrahydronaphtalène (fr)
1,2,3,4-τετραϋδροναφθαλένιο (el)
1,2,3,4-тeтрахидронафталeн (bg)
tetralina (pl)
Trade names:
tetralinova frakce
tetralín
IUPAC names:
1,2,3,4-tetrahydronaphthalene
1,2,3,4-tetrahydronaphtalene
1,2,3,4-Tetrahydronaphthalene
1,2,3,4-tetrahydronaphthalene
1,2,3,4-tetrahydronaphthalene
1,2,3,4-Tetrahydronaphthalin
Tetrahydronaphthalene
Preferred IUPAC name:
1,2,3,4-Tetrahydronaphthalene
Other names:
1,2,3,4-Tetrahydronaphthalene
Benzocyclohexane
NSC 77451
Tetrahydronaphthalene
Tetranap
Other identifiers:
119-64-2
601-045-00-4
