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Diisobutyl phthalate (DIBP) is a phthalate ester having the structural formula C6H4(COOCH2CH(CH3)2)2.
Diisobutyl phthalate (DIBP) is formed by the esterification of isobutanol and phthalic anhydride.
Diisobutyl phthalate (DIBP) and other phthalates are used as plasticizers due to their flexibility and durability.
CAS: 84-69-5
MF: C16H22O4
MW: 278.34
EINECS: 201-553-2
Synonyms
Diisobutylester kyseliny ftalove;Hexaplas M/1B;Isobutyl phthalate;Kodaflex DIBP;Palatinol 1C;Palatinol IC;Uniplex 155;DIISOBUTYL PHTHALATE FOR SYNTHESIS;DIISOBUTYL PHTHALATE;84-69-;DIBP;Palatinol IC;Phthalic Acid Diisobutyl Ester;Isobutyl phthalate;Hexaplas M/1B;Kodaflex DIBP;Di-iso-butyl phthalate;Phthalic acid, diisobutyl ester;Di(i-butyl)phthalate;1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) ester;Diisobutylester kyseliny ftalove;NSC 15316;bis(2-methylpropyl) phthalate;isobutyl-o-phthalate;1,2-Benzenedicarboxylic acid, 1,2-bis(2-methylpropyl) ester;DTXSID9022522;di-2-methylpropyl phthalate;di-l-butyl phthalate (DIBP);IZ67FTN290;CHEBI:79053;NSC-15316;Hatcol DIBP;DTXCID602522;1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester;1,2-Benzenedicarboxylic acid, di(2-methylpropyl) ester;Phthalic acid, bis-isobutyl ester;CAS-84-69-5;SMR000112470;di-isobutyl phthalate;CCRIS 6193;HSDB 5247;AI3-04278 (USDA);EINECS 201-553-2;BRN 2054802;UNII-IZ67FTN290;Diisobutylester kyseliny ftalove [Czech];AI3-04278;bis(2-methylpropyl) benzene-1,2-dicarboxylate;MFCD00026480;Isobutyl phthalate (VAN);EC 201-553-2;Diisobutyl phthalate, 99%;SCHEMBL42787;4-09-00-03177 (Beilstein Handbook Reference);MLS000516002;MLS002152902;BIDD:ER0640;1, bis(2-methylpropyl) ester;CHEMBL1370662;HMS2269D07;NSC15316;Tox21_202429;Tox21_300612;AKOS015837516;Diisobutyl phthalate (ACD/Name 4.0);WLN: 1Y1&1OVR BVO1Y1&1;NCGC00091360-01;NCGC00091360-02;NCGC00091360-03;NCGC00091360-04;NCGC00254487-01;NCGC00259978-01;1ST1119-1000H;NS00010605;P0298;G77491;Q162259;1,2-bis(2-methylpropyl) benzene-1,2-dicarboxylate
;Diisobutyl phthalate Solution in Hexane, 1000ug/mL;J-503794;1,2-benzenedicarboxylic acid di(2-methylpropyl) ester;Phthalic acid, bis-isobutyl ester 10 microg/mL in Cyclohexane;Diisobutyl phthalate, certified reference material, TraceCERT(R)
They are found in many industrial and personal products, such as lacquers, nail polish and cosmetics.
Diisobutyl phthalate (DIBP) can be absorbed via oral ingestion and dermal exposure.
When Diisobutyl phthalate (DIBP) comes to excretion, DIBP is first converted into the hydrolytic monoester monoisobutyl phthalate (MIBP).
The primary excretory route is urine, with biliary excretion being noted in minor amounts.
DIBP has lower density and freezing point than the related compound Diisobutyl phthalate (DIBP).
A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of isobutanol.
Diisobutyl phthalate (DIBP) has been used as a solvent-blender-diluent but is now of little interest since Diisobutyl phthalate (DIBP) is available in an odourless grade and at a very low cost.
Oily colorless liquid with a slight ester odor.
Denser than water.
Insoluble in water.
Low toxicity.
Diisobutyl phthalate (DIBP) is a colorless transparent oily liquid used as an alternative to DBP (Dibutyl Phthalate).
Diisobutyl phthalate (DIBP) is used in nitrocellulose and alkyd resin paints.
Diisobutyl phthalate (DIBP) is prepared by esterification process of isobutanol and phthalic anhydride.
Diisobutyl phthalate (DIBP) is an odorless plasticizer and has excellent heat and light stability.
Diisobutyl phthalate (DIBP) is the lowest cost plasticizer for cellulose nitrate.
Diisobutyl phthalate (DIBP) has lower density and freezing point than DBP.
Diisobutyl phthalate (DIBP) has similar properties as dibutyl phthalate and can be used as a substitute for it.
Diisobutyl phthalate (DIBP) Chemical Properties
Melting point: -64 °C
Boiling point: 327 °C(lit.)
Density: 1.039 g/mL at 25 °C(lit.)
Pour Point: -45
Vapor pressure: 11.2-1470Pa at 100℃
Refractive index: n20/D 1.49(lit.)
Fp: >230 °F
Solubility: Chloroform (Slightly), Methanol (Slightly)
Form: Liquid
Color: Colorless to Light yellow
Odor: Practically odorless when pure
Water Solubility: Insoluble
FreezingPoint: -50℃
BRN: 2054802
InChIKey: MGWAVDBGNNKXQV-UHFFFAOYSA-N
LogP: 4.11-4.45 at 20-30℃
CAS DataBase Reference: 84-69-5(CAS DataBase Reference)
NIST Chemistry Reference: Diisobutyl phthalate (DIBP)(84-69-5)
EPA Substance Registry System: Diisobutyl phthalate (DIBP) (84-69-5)
Uses
Diisobutyl phthalate (DIBP) is a Dialkyl phthalate ester phthalate plasticizer which can be used as a substitute of dibutyl phthalate.
Diisobutyl phthalate (DIBP) as well as other phthalates have genotoxic effects and studies shown an increase in its monoester metabolite in human urine over the years.
Industry use
Diisobutyl phthalate (DIBP) is used as a plasticizer additive in a range of plastic and rubber materials.
Diisobutyl phthalate (DIBP) has low volatility, which makes it ideal for use in products that require long-lasting flexibility, e.g. automotive parts, wire and cable insulation, and flooring.
Diisobutyl phthalate (DIBP) is dense and water-insoluble.
Diisobutyl phthalate (DIBP) has been found to be relatively non-toxic, but high levels of exposure to the compound may cause irritation to the eyes, skin and respiratory tract.
However, in recent years, concerns have been raised about the potential health risks of exposure to phthalates, including DIBP.
Therefore, several countries have restricted or even banned the use of certain phthalates in products.
Diisobutyl phthalate (DIBP) has been detected in various environmental matrices, such as air, water, and sediment.
Diisobutyl phthalate (DIBP) is known to bioaccumulate in certain aquatic species.
Production Methods
Diisobutyl phthalate (DIBP) is manufactured by esterifying phthalic anhydride and isobutanol in the presence of sulfuric acid.
Synthesis
Diisobutyl phthalate (DIBP) is synthesized by reaction of phthalic anhydride with isobutanol.
Various acids are used as a catalyst, such as sulfuric acid, sulfonated graphene, or iron(III) chloride.
Water is a byproduct.
Using sulfuric acid, the yield is 61% yield.
Optimization
Diisobutyl phthalate (DIBP) is a heterogeneous catalyst that has several advantages over traditional liquid acids like sulfuric acid.
Diisobutyl phthalate (DIBP) can be easily separated from the reaction mixture by filtration and can be reused multiple times without reduction in activity.
Furthermore, Diisobutyl phthalate (DIBP) is environmentally friendly, as it does not produce hazardous waste materials that are typically generated during the use of traditional liquid acid catalysts.
This method has a 95% yield.
Lewis acids, such as FeCl3, can also be used as the catalyst.
The Lewis acid catalysis process can be run at lower temperatures (50-100 °C), and gives a yield of 86%.
Environmental reactions
Diisobutyl phthalate (DIBP) can undergo various reactions that may impact the environment.
Examples include:
Hydrolysis: Hydrolyzation of Diisobutyl phthalate (DIBP) can be done by enzymes, bacteria, and other microorganisms in the environment to form phthalic acid and isobutyl alcohol.
Diisobutyl phthalate (DIBP) can lead to the breakdown and the eventual degradation of DIBP in the soil and water supply.
Photodegradation: Diisobutyl phthalate (DIBP) can undergo photodegradation by exposure to the sunlight.
Diisobutyl phthalate (DIBP) can lead to the formation of several degradation products, including phthalic acid, isobutyraldehyde, and other aldehydes.
Biodegradation: Diisobutyl phthalate (DIBP) can be degraded by microorganisms in soil and in the water.
This can transform Diisobutyl phthalate (DIBP) into other compounds such as phthalic acid and various isobutyl alcohol derivatives.
Sorption: Diisobutyl phthalate (DIBP) can adsorb or sorb onto soil and sediment particles, which can limit its mobility and availability for biological or chemical degradations and reactions.
Oxidation: Diisobutyl phthalate (DIBP) can be oxidized in the presence of ozone or other reactive oxygen species.
The formation of various oxidation products, including aldehydes, ketones, and carboxylic acids can be expected.
These reactions can impact the persistence, bioaccumulation, and toxicity in the environment and may have implications for human and ecosystem health.
Reactivity Profile
Diisobutyl phthalate (DIBP) reacts with acids to liberate heat along with isobutyl alcohol and phthalic acid.
May react sufficiently exothermically with strong oxidizing acids to ignite the reaction products.
Heat is also generated by interaction with caustic solutions.
Flammable hydrogen is generated by mixing with alkali metals and hydrides.
Can generate electrostatic charges in handling.
