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Solketal is an organic chemical compound used mainly as a solvent, intermediate, and protecting-group reagent.
Solketals systematic name is 2,2-dimethyl-1,3-dioxolane-4-methanol, and it is commonly derived from glycerol.
Solketal is considered a value-added glycerol derivative.
CAS Number: 100-79-8
Molecular Formula: C6H12O3
Molecular Weight: 132.16
EINECS Number: 202-888-7
Synonyms: Solketal, 100-79-8, 2,2-Dimethyl-1,3-dioxolane-4-methanol, Glycerolacetone, Glycerol dimethylketal, Dioxolan, Isopropylidene glycerol, Glycerol acetonide, 2,3-Isopropylideneglycerol, 1,3-Dioxolane-4-methanol, 2,2-dimethyl-, Acetone monoglycerol ketal, Acetone glycerol, Glycerinisopropylidene ether, 2,3-O-Isopropylideneglycerol, 2,2-Dimethyl-4-hydroxymethyl-1,3-dioxolane, Acetone, cyclic (hydroxymethyl)ethylene acetal, 3XK098O8ZW, NSC-59720, DTXSID9021845, 2,3-Isopropylidene-sn-glycerol, RefChem:441233, DTXCID901845, 202-888-7, (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol, DL-1,2-Isopropylideneglycerol, 1,2-O-Isopropylideneglycerol, 1,2-Isopropylideneglycerol, 2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxacyclopentane, 1,2-Isopropylideneglycerin, 2,3-(Isopropylidenedioxy)propanol, 2,2-Dimethyl-1,3-dioxolan-4-ylmethanol, 2,2-Dimethyl-4-hydroxymethyldioxolane, 1,2-O,O-Isopropylideneglycerin, Glycerol, 1,2-O-isopropylidene, Glycerolacetonide, 2,2-Dimethyl-5-hydroxymethyl-1,3-dioxolane, 4-Hydroxymethyl-2,2-dimethyl-1,3-dioxolane, MFCD00063238, NSC 59720, (+/-)-2,2-Dimethyl-1,3-dioxolane-4-methanol, 2,2-Dimethyl-4-oxymethyl-1,3-dioxolane, 36543-79-0, 2,2-Dimethyl-1,3-dioxolan-4-yl methanol, GIE, .alpha.,.beta.-Isopropylideneglycerol, 1,2-Isopropylidene-rac-glycerol, R-(-)-Sollketal, (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol, (r,s)-2,2-dimethyl-1,3-dioxolane-4-methanol, (+/-)-2,2-Dimethyl-4-hydroxymethyl-1,3-dioxolane, D-Acetone glycerol, Glycerol acetonide (VAN), alpha,beta-Isopropylideneglycerol, EINECS 202-888-7, 1,2-isopropylidene glycerol, BRN 0104465, UNII-3XK098O8ZW, AI3-03547, Racemic solketal, Glycasol/solketal, (RS)-Solketal, 2,3-dioxacyclopentane, 1,3-Dioxolane-4-methanol, 2,2-dimethyl-, (S)-, 1,O-Isopropylideneglycerin, EC 202-888-7, Glycerol,2-O-isopropylidene, SCHEMBL23556, ACETONE GLYCERIN KETAL, 2,3-dioxolan-4-yl methanol, 5-19-02-00362 (Beilstein Handbook Reference), DL-1,2-isoproylideneglycerol, SCHEMBL589481, 1,2-o-isopropylidene glycerol, 2,2-Dimethyl-1,3-dioxolan-4-yl methanol [IUPAC], 4-Hydroxymethyl-2,3-dioxolane, 1.2-isopropylidene-rac-glycerol, CHEMBL3342436, dimethyl-1,3-dioxolane-4-methanol, NSC59720, ISOPROPYLIDENE GLYCEROL [MI], (.+/-.)-Glycerol 1,2-acetonide, AC-364, BBL012719, STK803305, WLN: T5O COTJ B1 B1 D1Q, AKOS000120075, AKOS022060550, CS-W018546, MI03369, 2,2-dimethyl-1,3-dioxolan-4-methanol, 2,2-dimethyl-1,3-dioxolane4-methanol, Dimethyl-4-hydroxymethyl-1,3-dioxolane, 2,3-(dimethylmethylenedioxy)-1-propanol, dl-.alpha.,.beta.-Isopropylideneglycerol, (.+/-.)-1,2-O-Isopropylideneglycerol, AS-46670, BP-14103, SY010573, (2,2-dimethyl-1,3-dioxolan-4yl)methanol, 2,2-dimethyl-[1,3]dioxolane-4-methanol, DB-011643, DL-1,2-Isopropylideneglycerol, >=97.0%, (2,2-dimethyl[1,3]dioxolan-4-yl)methanol, 2,2-Dimethyl-4-hydroxymethyl-1,3-dioxolan, 4-hydroxymethyl-2,2-dimethyl-1,3-dioxolan, D0710, NS00001386, ST50998271, (2,2-dimethyl-[1,3]dioxolan-4-yl)methanol, EN300-20586, (-)-2,2-Dimethyl-1,3-dioxolane-4-methanol, 2,2-Dimethyl-4-hydroxymethyl-1,3-dioxolane, (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol, (2,2-dimethyl-1,3-dioxolan-4-yl)methan-1-ol, (4RS)-2,2-dimethyl-1,3-dioxolane-4-methanol, (4RS)-2,2-Dimethyl-1,3-dioxolane-4-methanol, (rac)-2,2-dimethyl-[1,3]-dioxolane-4-methanol, 2,2-dimethyl-1,3-dioxolane-4-methanol (solketal), 2,2dimethyl-1,3-dioxolane-4-methanol (solketal), F095006, rac-(2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol, rac-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol, (R)-(?)-2,2-Dimethyl-1,3-dioxolane-4-methanol, (S)-(+)-2,2-Dimethyl-1,3-dioxaolane-4-methanol, Q2968854, [(4R/S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methanol, F0001-0027, Z104479028, DL-ALPHA,BETA-ISOPROPYLIDENEGLYCEROL;LABOTEST-BB LT00233172;ISOPROPYLIDENGLYCEROL;ISOPROPYLIDENEGLYCEROL;GLYCEROL DIMETHYLKETAL;2,3-O-ISOPROPYLIDENEGLYCEROL;(+/-)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL;2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL
Solketal is a cyclic acetal (ketal) formed by the reaction of glycerol with acetone.
This structure protects two hydroxyl groups of glycerol, leaving one free hydroxyl group available for further reactions.
Because of this, solketal is widely used in organic synthesis.
Solketal is a colorless to pale yellow liquid with low viscosity.
Solketal has a mild, slightly sweet odor.
It is miscible with water and many organic solvents.
Solketal is chemically stable under neutral and basic conditions, but it can be hydrolyzed back to glycerol and acetone under acidic conditions.
This reversible behavior makes it useful as a temporary protecting group.
Solketal is considered relatively non-volatile and easy to handle.
Industrially, solketal is valued as a bio-based chemical, since glycerol is a renewable raw material.
It is often highlighted in green chemistry and sustainable chemistry contexts.
Its production adds value to glycerol streams from biodiesel manufacturing.
In formulation and materials science, solketal shows good solvency and compatibility with polar and semi-polar systems.
It can improve solubility of certain compounds.
This makes it useful beyond laboratory synthesis.
Solketal is best described as a glycerol-derived cyclic ketal used as a solvent, intermediate, and protecting group.
Its importance lies in its chemical versatility and renewable origin.
Solketal is a protected form of glycerol with an isopropylidene acetal group joining two neighboring hydroxyl groups.
Solketal contains a chiral center on the center carbon of the glycerol backbone, and so can be purchased as either the racemate or as one of the two enantiomers.
Solketal has been used extensively in the synthesis of mono-, di- and triglycerides by ester bond formation.
The free hydroxyl group of solketal can be esterified with a carboxylic acid to form the protected monoglyceride.
The isopropylene group can then be removed using an acid catalyst in aqueous or alcoholic medium.
The unprotected diol can then be esterified further to form either the di- or triglyceride.
Solketal is increasingly explored as a green solvent alternative in organic synthesis and formulation science.
Solketals renewable origin and relatively benign safety profile make it attractive for replacing traditional dipolar aprotic solvents in certain reactions.
This supports efforts to reduce reliance on petroleum-based chemicals.
In organic synthesis, solketal is commonly used as a glycerol protecting group.
By masking two hydroxyl groups, it allows selective reactions at the remaining alcohol function.
After synthesis, the protecting group can be removed under mild acidic conditions.
Solketal shows good miscibility behavior in multicomponent systems.
Solketal blends well with alcohols, esters, ketones, and water.
This makes it useful in solvent blends and reaction media requiring tunable polarity.
In materials chemistry, solketal has been investigated as a building block for polymers and resins.
Its hydroxyl functionality enables incorporation into polymer backbones or side chains.
This allows production of bio-based or partially renewable materials.
Solketal has also been studied in electrochemistry and battery research as a solvent or co-solvent.
Its polarity and stability can support ion transport in certain electrolyte systems.
These applications are still largely experimental.
From a processing perspective, solketal is appreciated for its low vapor pressure.
This reduces solvent loss and operator exposure during handling.
It also contributes to safer and more controllable industrial processes.
In environmental chemistry, solketal is considered readily biodegradable under appropriate conditions.
This contributes to its favorable environmental profile.
It is often cited as an example of value-added utilization of renewable feedstocks.
Overall, solketal is regarded as a flexible and sustainable chemical intermediate.
Its importance spans green chemistry, synthesis, formulation, and materials research.
Its continued development reflects growing demand for renewable and multifunctional chemicals.
Molecular weight: 132.16 g/mol
Melting point: −27 °C
Boiling point: 189–191 °C
Density: 1.066 g/mL (20 °C)
Vapor pressure: 34 Pa (20 °C)
Refractive index: n20/D 1.434
Flash point: 176 °F
Storage temperature: Sealed in dry conditions; 2–8 °C
Solubility: 172 g/L; miscible with water
Water solubility: Miscible
Form: Liquid
Color: Clear, colorless
pKa: 14.20 ± 0.10 (predicted)
pH: 4.0–7.5 (in H2O)
Optical activity: +4.1° (C=1.00 g/100 mL, EtOH, 20 °C, 589 nm)
Merck index: 14,5213
BRN: 104465
Cosmetics ingredients functions: Hair conditioning
InChI: 1S/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3
InChIKey: RNVYQYLELCKWAN-UHFFFAOYSA-N
SMILES: CC1(C)OCC(CO)O1
LogP: 0.3 (20 °C)
Solketal has attracted attention as a platform molecule in sustainable chemistry.
Because it is derived from glycerol, it helps valorize surplus glycerol generated in biodiesel production.
This aligns it with renewable and circular-chemistry strategies.
From a reactivity standpoint, the free hydroxyl group on solketal allows further functionalization.
Solketal can undergo esterification, etherification, or oxidation reactions.
This makes solketal a versatile intermediate for synthesizing fine chemicals and specialty materials.
Solketal exhibits good thermal and chemical stability under normal handling conditions.
It does not readily decompose at moderate temperatures.
This stability supports its use as a solvent and process aid.
In solvent applications, solketal shows intermediate polarity.
Solketal can dissolve a wide range of polar organic compounds while remaining compatible with water.
This dual affinity is useful in mixed solvent systems.
Solketal is often described as having low toxicity and favorable safety characteristics compared to many petroleum-derived solvents.
This has increased interest in replacing traditional solvents with solketal in certain applications.
Such substitution supports greener formulation design.
In fuel and energy research, solketal has been studied as a fuel additive.
It can improve cold-flow properties and oxygen content of fuels.
These properties are of interest in alternative fuel development.
Solketal also shows plasticizing behavior in some polymer systems.
It can improve flexibility and processing of certain materials.
This expands its relevance beyond laboratory chemistry.
Solketal is valued as a multifunctional, renewable, and adaptable chemical.
Its combination of stability, reactivity, and sustainability makes it important in research and industrial contexts.
Solketal is also investigated in reaction engineering and process optimization.
Its stability and miscibility allow it to be used in continuous-flow reactors.
This supports safer and more efficient chemical processing.
In catalysis research, solketal is used both as a solvent and as a reactant.
Its acetal structure can interact favorably with acid or metal catalysts.
This makes it useful in studying catalyst selectivity and recyclability.
Solketal shows low corrosiveness compared with many conventional solvents.
This reduces wear on equipment and extends reactor lifetime.
It is advantageous in pilot-scale and industrial systems.
In formulation science, solketal can act as a co-solvent to improve solubility of active ingredients.
It helps stabilize formulations containing both hydrophilic and moderately hydrophobic components.
This is useful in coatings, inks, and specialty liquids.
Solketal is explored in fuel-blending and combustion studies beyond additive research.
Its oxygen-rich structure can influence combustion behavior.
These studies aim to improve efficiency and reduce emissions.
In pharmaceutical research, solketal is used as an intermediate for synthesizing drug candidates and excipients.
Its glycerol-derived backbone offers biocompatibility advantages.
These applications focus on molecular design rather than direct use.
Solketal has been examined as a cryoprotective or stabilizing agent in certain experimental systems.
Its hydrogen-bonding capacity can influence freezing behavior.
These uses remain largely at the research stage.
Solketal is increasingly viewed as a strategic renewable platform molecule.
Its versatility allows adaptation across many scientific and industrial domains.
This breadth of applicability underlines its growing importance in sustainable chemistry.
Uses:
Solketal is useful for synthesis of mono-, di- and triglycerides.
Solketal is used as the starting reagent for synthesis of tulipaline derivatives.
Solketal acts as a fuel additive in gasoline.
Solketal is an inhibitor of Methyl ethyl ketone .
Solketal is used in organic synthesis as a protecting group for glycerol.
It temporarily masks two hydroxyl groups, enabling selective reactions at the remaining alcohol.
After synthesis, it can be removed under mild acidic conditions.
In green solvent applications, solketal is used as a bio-based solvent or co-solvent.
It helps dissolve polar and semi-polar compounds while remaining compatible with water.
This supports replacement of petroleum-derived solvents in sustainable formulations.
Solketal is applied as a chemical intermediate in the production of fine chemicals and specialty materials.
Its free hydroxyl group allows further functionalization by esterification or etherification.
In fuel and energy research, solketal is studied as a fuel additive.
Solketal can improve cold-flow properties and oxygen content of fuels.
These effects are relevant in alternative and biofuel development.
Solketal is used in polymer and materials science as a reactive intermediate or plasticizing component.
It can be incorporated into bio-based polymers and resins.
This improves flexibility and supports renewable material design.
In formulation science, solketal serves as a co-solvent to enhance solubility and stability.
It helps bridge hydrophilic and moderately hydrophobic ingredients.
Applications include coatings, inks, and specialty liquids.
Solketal is applied in pharmaceutical and biomedical research as a synthesis intermediate.
It is used in the preparation of drug candidates and excipients derived from glycerol chemistry.
These uses focus on molecular construction rather than direct administration.
In electrochemical and battery research, solketal is explored as a solvent or additive.
Its polarity and stability can support ion transport in experimental electrolyte systems.
These applications are mainly research-driven.
Solketal is used where renewable origin, chemical versatility, and solvent functionality are required.
Solketal is used in process chemistry and continuous manufacturing.
Its stability and miscibility make it suitable for flow reactions and scalable processes.
This supports safer, more efficient production routes.
In coatings and inks, solketal is used as a co-solvent to improve film formation and ingredient compatibility.
Solketal helps dissolve resins and additives while maintaining manageable viscosity.
This improves application uniformity and finish quality.
Solketal is applied in adhesives and sealants as a formulation aid.
It can enhance solubility of functional additives and adjust rheology.
These effects support consistent bonding performance.
In agrochemical formulations, solketal is explored as a solvent or carrier for active ingredients.
Its water miscibility and moderate polarity help stabilize complex mixtures.
These uses focus on formulation efficiency and sustainability.
Solketal is used in cleaning and specialty solvents where low volatility and renewability are desired.
It can replace harsher solvents in niche industrial cleaning tasks.
This reduces operator exposure and environmental impact.
In flavor, fragrance, and aroma chemistry research, solketal serves as a synthesis intermediate.
It enables controlled modification of glycerol-derived structures.
These applications are research-oriented rather than direct sensory use.
Solketal is applied in nanomaterials and dispersion research as a medium to stabilize particles.
Its hydrogen-bonding capacity can aid dispersion of certain solids.
This supports development of functional suspensions.
In academic and industrial R&D, solketal is used as a model renewable molecule.
Solketal helps evaluate catalytic systems, solvent effects, and green chemistry metrics.
This role supports method development and sustainability assessment.
Solketal is used across applications that prioritize renewable sourcing, solvent flexibility, and chemical adaptability.
Safety Profile:
A poison by intravenous route.
Mutation data reported a very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials.
Solketal is generally considered to have low to moderate hazard potential under normal industrial and laboratory use.
Solketal is less hazardous than many traditional organic solvents but still requires standard chemical safety precautions.
Skin contact may cause mild irritation, particularly with prolonged or repeated exposure.
Symptoms can include redness or dryness.
Protective gloves are recommended during handling of the concentrated liquid.
Eye contact may result in temporary irritation, such as redness or stinging.
Immediate rinsing with plenty of water is advised if exposure occurs.
Eye protection should be worn in laboratory and industrial settings.
Inhalation risk is relatively low due to its low volatility.
However, inhalation of vapors or aerosols at elevated temperatures may cause mild respiratory irritation.
Adequate ventilation is recommended during processing.
Ingestion of significant amounts may cause gastrointestinal discomfort, including nausea or irritation.
It is not intended for direct consumption.
Medical advice should be sought in case of accidental ingestion.
Solketal is combustible and should be kept away from open flames, sparks, and strong oxidizing agents.
Thermal decomposition at high temperatures may produce irritating fumes.
Standard precautions for handling organic liquids should be followed.
