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CAS #: 25265-77-4
EC Number: 246-771-9
IUPAC Name: (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate
Formula: C12H24O3
Molecular mass: 216.4 g/mol
DESCRIPTION:
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate is a mixture of several chemical compounds from the group of ester alcohols.
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate is also an ester of isobutyric acid .
The mixture of substances was brought onto the market in 1961 by Eastman Chemical under the brand name "Texanol".
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate can be prepared starting from isobutanal
2,2,4-Trimethyl-1,3-pentanediolmono(2-methylpropanoate) is a volatile organic compound (VOC) being useful in paints and printing inks.
As coalescent for latex paints, 2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate finds applications in various fields including coatings, nail care, Printing inks, Solvents for cosmetics and personal care, plasticizers.
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate is also utilized as a coalescing agent to reduce the minimal film forming temperature (MFFT) during latex film preparation.
Study using coupled capillary gas chromatography-mass spectrometry (HRGC-MS) has confirmed its detection in polypropylene packed food samples1.
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate is also employed in pharma industry.
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate may be further used in the prepare carbon nanotube (CNT) paste employed in field emission displays (FED).
Structural Isomerism and Stereoisomers:
Since Texanol is a monoester of racemic 2,2,4-trimethyl-1,3-pentanediol with isobutyric acid , apart from minor impurities (2,2,4-trimethyl-1,3-pentanediol and its diisobutyric acid ester ) it contains a total of four different ones ester.
The ( RS )-(±)-ester [1:1 mixture of two substances, the ( R )-enantiomer and the ( S )-enantiomer] - is obtained by esterification of the primary hydroxy group of the diol .
There is also a second ( RS )-(±)-ester [1:1 mixture of two substances, the ( R )-enantiomer and ( S )-enantiomer] - obtained by esterification of the secondary hydroxy group of the diol
Usage of 2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate:
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate is used as a coalescing agent (film-forming agent) for latex paints .
The annual production volume in 1995 was just under 100,000 t.
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate is used as Intermediate in the manufacture of plasticizers, surfactants, pesticides, and resins.
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate is Employed In pharma industry.
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate is used as Coalescent for latex paints.
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate is used for applications in Coatings, Nail care, Printing inks, Solvents for cosmetics and personal care, plasticizers.
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate (texanol) may be used in the prepare carbon nanotube (CNT) paste employed in field emission displays (FED).
Household & Commercial/Institutional Products
Information on 417 consumer products that contain Texanol in the following categories is provided:
• Auto Products
• Commercial / Institutional
• Home Maintenance
• Inside the Home
• Landscaping/Yard
Industry Processing Sectors:
All other basic organic chemical manufacturing
All other chemical product and preparation manufacturing
Construction
Oil and gas drilling, extraction, and support activities
Paint and coating manufacturing
Printing ink manufacturing
2,2,4-trimethyl-1,3-pentanediol monoisobutyrate, also known as texanol, is an alcohol ester majorly used as a coalescing agent in latex paints.
2,2,4-trimethyl-1,3-pentanediol is commercially manufactured by the self-condensation process of dry, acid-free isobutyraldehyde in the presence of sodium isobutoxide as a catalyst in an enclosed vessel.
The mixture is then washed with water to remove other chemicals formed during the reaction and the remaining liquid is almost a 99% pure form of texanol.
Isobutyraldehyde is the primary raw material used in the production of texanol.
2,2,4-trimethyl-1,3-pentanediol is generally produced as a by-product during the manufacturing of propene.
2,2,4-trimethyl-1,3-pentanediol is used in a wide range of applications such as the production of pharmaceuticals, chemical intermediates, plasticizers, and paints and coatings solvents.
Its demand for the production of other products tends to hamper the manufacturing cycle of texanol, leading to price fluctuations.
The latex paint application segment dominated the global consumption of the product mainly due to its non-yellowing and non-chipping properties.
They are also termed as acrylics with water-soluble bases, which can be easily cleaned from any surface.
These properties have collectively resulted in high demand of 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate across various industries such as construction, DIY (Do-It-Yourself), and automotive aftermarket.
The rising demand from latex paints from these industries is anticipated to encourage the manufacturers across the globe to develop sustainable products.
Texanol has been regarded as a non-VOC emitting solvent in U.S., China, and European Union.
The preference for green certification ingredients is thus anticipated to propel the consumption of low VOC solvents such as texanol.
2,2,4-trimethyl-1,3-pentanediol monoisobutyrate is compliant with major regulatory authorities present across the globe such as U.S. EPA, EU commission, China Environmental United Certification Co. Ltd. (CEC), California Consumer Products Regulations, and State Environmental Protection Administration of China (SEPA).
Moreover, it has been awarded the Green Label Type II certificate by China Environmental United Certification Co. Ltd. (CEC), which is anticipated to generate a positive impact on market growth.
CAS #: 25265-77-4
EC Number: 246-771-9
IUPAC Name: (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate
Formula: C12H24O3
Molecular mass: 216.4 g/mol
Application Insights
The major applications of trimethyl pentanediol monoisobutyrate include its utilization as a coalescing agent in the production of latex paint, as a solvent in the manufacturing of cosmetics, polishes, pesticide additives, and chemical intermediate.
In 2019, latex paint production accounted for 73.5% of market share, in terms of volume.
Increasing demand for water-based low VOC products in the construction industry along with the launch of several high-quality resins is expected to drive the demand for 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate over the forecast period.
Globally, water-based formulations are replacing solvent-based painting product counterparts, due to their environment compliant properties, especially in the construction industry.
These are used in the exterior as well as interiors of residential and commercial buildings.
The rapidly growing construction industry followed by rising redevelopment trend is anticipated to boost the demand for 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate over the forecast period.
Paint manufacturers are also developing new products with latex paints such as aerosol or spray cans that are further anticipated to witness high demand from the automotive, advertising, and DIY industries.
Due to their safe usage, these products are also readily available directly to the customers through e-commerce platforms and local stores.
Such advancements in the industry are expected to propel the growth of 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate market across the globe.
However, other applications include oil-drilling muds, wood preservative carriers, ore flotation/ frothing, and floor polishes.
It is also permitted by the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) for the usage in pesticide formulations for non-food crops.
The chemical is anticipated to gain wide acceptance as a pesticide additive, owing to its biodegradable properties.
The chemical is thus anticipated to gain significant demand from turf and gardening use pesticide manufacturers.
PHYSICAL & CHEMICAL INFORMATION OF 2,2,4-TRIMETHYL-1,3-PENTANEDIOL MONOISOBUTYRATE
Physical State;
Appearance: LIQUID
Formula: C12H24O3
Molecular mass: 216.4 g/mol
Boiling point: 255-260°C
Melting point: -50°C
Relative density (water = 1): 0.95
Solubility in water, g/100ml: 2
Vapour pressure, Pa at 20°C: 1.3
Relative vapour density (air = 1): 7.5
Relative density of the vapour/air-mixture at 20°C (air = 1): 1.00
Flash point: 120°C o.c.
Auto-ignition temperature: 393°C
Explosive limits, vol% in air: 0.6-4.2
Octanol/water partition coefficient as log Pow: 3.47
Specific Gravity: 0.95
Density: 0.9500g/mL
Assay: 99%
Form: liquid
technique(s): GC/MS: suitable
Impurities: ≤0.10% (water)
refractive index: n20/D 1.441 (lit.)
Molecular Weight: 216.32
XLogP3-AA: 3.1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Coun: 6
Exact Mass: 216.17254462
Monoisotopic Mass: 216.17254462
Topological Polar Surface Area: 46.5 Ų
Heavy Atom Count: 15
Formal Charge: 0
Complexity: 207
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Evaporation Rate:
(n-butyl acetate = 1) : 0.002
(ether = 1) : 6051
Refractive Index @ 20°C: 1.4423
Vapor Density (air = 1): 7.5
Vapor Pressure
@ 25°C
0.013 mm Hg
1.73 Pa
@ 20°C
0.01 mm Hg
1.33 Pa
@ 55°C
3.3 KPa
Boiling Point @ 760 mm Hg: 255-260.5°C (491-501°F)
Freezing Point: -50°C (-58°F)
Flash Point Cleveland Open Cup: 120°C (248°F)
Autoignition Temperature. 393°C (739°F)
Hansen Solubility Parameters:
Nonpolar: 7.4
Polar: 3
Hydrogen Bonding : 4.8
Total: 9.3
Surface Tension @ 20°C: 28.9 dynes/cm
Electrical Resistance: >20 Megohms
Expansion Coefficient, per °C @ 20°C: 0.001
Critical Temperature: 391.9°C
Critical Pressure: 19.9 ATM
Critical Volume: 718.6 ml/g•mol
Heat of Vaporization: 15196 cal/g•mol
Heat of Combustion: -1607.7 kcal/g•mol
Liquid Heat Capacity @ 25°C :110.74 cal/(g*mol)(°C)
Liquid Viscosity @ 20°C :13.5 cP (mPa•s)
Nitrocellulose Solubility: Active
CAS #: 25265-77-4
EC Number: 246-771-9
IUPAC Name: (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate
Formula: C12H24O3
Molecular mass: 216.4 g/mol
SAFETY INFORMATION:
Yellow triangle Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues.
Specifically, a chemical with this code is not associated with a low level of hazard concern for all human health and environmental endpoints.
While it is a best-in-class chemical and among the safest available for a particular function, the function fulfilled by the chemical should be considered an area for safer chemistry innovation.
Health Hazards :
Exposure can cause mild irritation of eyes, nose and throat.
Fire Hazards:
Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire.
Combustible.
Safety and Hazard Properties:
Lower Explosive Limit (LEL): 0.62 % at 300°F
Upper Explosive Limit (UEL): 4.24 % at 393°F
Explosive Limits and Potential
Explosive limits , vol% in air: 0.6-4.2
First Aid Measures:
Get medical attention.
INHALATION: Remove to fresh air.
EYES: Flush with water for at least 15 min., lifting lids occasionally.
SKIN: Remove contaminated clothing and shoes.
Wash with soap and water.
Skin First Aid:
Rinse and then wash skin with water and soap.
Eye First Aid:
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Fire Fighting:
Fire Extinguishing Agents Not to Be Used: Since material is lighter than water and insoluble, fire could be spread by using water in an uncontained area.
Fire Extinguishing Agents: Dry chemical, alcohol foam, or carbon dioxide.
Use powder, AFFF, foam, carbon dioxide.
Accidental Release Measures:
Spillage Disposal:
Do NOT let this chemical enter the environment.
Collect leaking and spilled liquid in sealable containers as far as possible.
Absorb remaining liquid in sand or inert absorbent.
Then store and dispose of according to local regulations.
Exposure Control and Personal Protection:
Inhalation Risk:
Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly on spraying.
Effects of Short Term Exposure:
The substance is irritating to the eyes and skin.
Personal Protective Equipment (PPE):
Where splashing is possible wear full face shield or chemical safety goggles.
Fire Prevention :
NO open flames.
Skin Prevention :
Protective gloves.
Eye Prevention :
Wear safety spectacles.
Ingestion Prevention:
Do not eat, drink, or smoke during work.
Stability and Reactivity:
Air and Water Reactions:
No rapid reaction with air No rapid reaction with water
Reactive Group:
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Reactivity Profile:
1-ISOBUTYRATE is an ester.
Esters react with acids to liberate heat along with alcohols and acids.
Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products.
Heat is also generated by the interaction of esters with caustic solutions.
Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire .
CAS #: 25265-77-4
EC Number: 246-771-9
IUPAC Name: (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate
Formula: C12H24O3
Molecular mass: 216.4 g/mol
Synonyms:
MeSH Entry Terms:
2,2,4-trimethyl-1,3-pentanediol monoisobutyrate
Texanol
Depositor-Supplied Synonyms:
Texanol
25265-77-4
77-68-9
3-Hydroxy-2,2,4-trimethylpentyl isobutyrate
2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate
Propanoic acid, 2-methyl-, 3-hydroxy-2,2,4-trimethylpentyl ester
2,2,4-Trimethyl-1,3-pentanediolmono(2-methylpropanoate)
2,2,4-Trimethylpentane-1,3-diol monoisobutyrate
(3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate
Propanoic acid, 2-methyl-, monoester with 2,2,4-trimethyl-1,3-pentanediol
2,2,4-TRIMETHYL-1,3-PENTANEDIOL 1-ISOBUTYRATE
1,3-Pentanediol, 2,2,4-trimethyl-, 1-isobutyrate
Isobutyric Acid 3-Hydroxy-2,2,4-trimethylpentyl Ester
3-Hydroxy-2,2,4-trimethylpentyl 2-methylpropanoate
Isobutyraldehyde trimer
Texanolesteralcohol
EINECS 201-049-2
component of Texanol
Texanol Ester Alcohol
Haltanol Ester Alcohol
DSSTox_CID_7857
DSSTox_RID_78592
DSSTox_GSID_27857
SCHEMBL56321
CHEMBL3184970
DTXSID10872295
Tox21_200148
MFCD00148967
AKOS015900105
NCGC00164419-01
NCGC00248541-01
NCGC00257702-01
LS-14159
O919
CAS-25265-77-4
FT-0699920
I0405
3-hydroxy-2,2,4-trimethylpentyl 2-methylpropionate
J-506772
Q27272708
2-Methyl-propanoic Acid 3-Hydroxy-2,2,4-trimethylpentyl Ester
3-Hydroxy-2,2,4-trimethylpentyl Isobutyrate (contains ca. 40% 2,2,4-Trimethyl-1,3-pentanediol 3-monoisobutyrate)
