84-69-5

Basic information

• Product Name: Diisobutyl phthalate
• Synonyms: Diisobutylester kyseliny ftalove;Hexaplas M/1B;Isobutyl phthalate;Kodaflex DIBP;Palatinol 1C;Palatinol IC;Uniplex 155;DIISOBUTYL PHTHALATE FOR SYNTHESIS
• CAS NO: 84-69-5
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.34
• EINECS: 201-553-2
• Product Categories: solvent;Functional Materials;Phthalates (Plasticizer);Plasticizer;Plasticizers;Polymer Additives;Polymer Science;C12 to C63;Carbonyl Compounds;Esters
• Mol File: 84-69-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: -64 °C
• Boiling Point: 327 °C(lit.)
• Flash Point: >230 °F
• Appearance: oily colorless liquid with a slight ester odor
• Density: 1.039 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.49(lit.)
• Water Solubility: Insoluble
• BRN: 2054802
• CAS DataBase Reference: Diisobutyl phthalate(CAS DataBase Reference)
• NIST Chemistry Reference: Diisobutyl phthalate(84-69-5)
• EPA Substance Registry System: Diisobutyl phthalate(84-69-5)

Safety Data

• Hazard Codes: N,Xn,T
• Statements: 50/53-63-62-61
• Safety Statements: 60-61-36/37-45-53
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 2
• RTECS: TI1225000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 84-69-5(Hazardous Substances Data)

Usage

Chemical Properties

clear liquid

Uses

Diisobutyl Phthalate is a Dialkyl phthalate ester phthalate plasticizer which can be used as a substitute of dibutyl phthalate. Diisobutyl Phthalate as well as other phthalates have genotoxic effects and studies shown an increase in its monoester metabolite in human urine over the years.

Definition

ChEBI: A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of isobutanol.

Production Methods

Diisobutyl phthalate is manufactured by esterifying phthalic anhydride and isobutanol in the presence of sulfuric acid.

General Description

Oily colorless liquid with a slight ester odor. Denser than water. Insoluble in water. Low toxicity.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Diisobutyl phthalate 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 [Handling Chemicals Safely, 1980. p. 250].

Health Hazard

Vapors from very hot material may irritate eyes and produce headache, drowsiness, and convulsions.

Fire Hazard

Diisobutyl phthalate is combustible.

Safety Profile

Moderately toxic by intraperitoneal route. Mdly toxic by ingestion and skin contact. Experimental teratogenic and reproductive effects. Combustible when exposed to heat or flame. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes.

InChI:InChI=1/C16H22O4/c1-9(2)7-11-5-6-12(15(17)18)14(16(19)20)13(11)8-10(3)4/h5-6,9-10H,7-8H2,1-4H3,(H,17,18)(H,19,20)/p-2

Synthetic route

phthalic anhydride (85-44-9) + 2-methyl-propan-1-ol (78-83-1) → 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5)

Conditions	Yield
Stage #1: phthalic anhydride; 2-methyl-propan-1-ol at 120 - 150℃; for 4h; Stage #2: With calcium oxide at 20℃; for 1h; Reagent/catalyst;	99.5%
With sulfonated graphene In toluene at 112℃; for 4h;	95%
With toluene at 130℃; Erhitzen des vom Toluol befreiten Reaktionsgemisches bis auf 190grad;
With sulfuric acid; toluene
With sulfuric acid at 135 - 140℃; for 8h; Large scale;

2-methyl-propan-1-ol (78-83-1) + benzene-1,2-dicarboxylic acid (88-99-3) → 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5)

Conditions	Yield
With triflic acid on silica-encapsulated superparamagnetic iron oxide nanoparticles In neat (no solvent) at 90℃; for 1.5h; Catalytic behavior; Time; Reagent/catalyst; Flow reactor; Green chemistry;	75%

2-methyl-propan-1-ol (78-83-1) + Diethyl phthalate (84-66-2) → 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5)

Conditions	Yield
With sodium

C16H22O4(1-) → 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5) + CO2 anion radical

Conditions	Yield
With carbon dioxide; tetrabutylammonium perchlorate In N,N-dimethyl-formamide at 25℃; Rate constant; electrochemical reduction;

phthalic anhydride (85-44-9) + 2-Ethylhexyl alcohol (104-76-7) + 2-methyl-propan-1-ol (78-83-1) → (isobutyl)(2-ethylhexyl) phthalate + Di(2-ethylhexyl)phthalate (117-81-7) + 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5)

Conditions	Yield
Stage #1: phthalic anhydride; 2-methyl-propan-1-ol at 130℃; for 1h; Stage #2: 2-Ethylhexyl alcohol; 2-methyl-propan-1-ol; tin oxide at 220℃; under 150.015 Torr; for 7h; Product distribution / selectivity; Dean-Stark trap;

phthalic anhydride (85-44-9) + isononanol (3452-97-9, 140237-84-9, 140237-85-0) + 2-methyl-propan-1-ol (78-83-1) → (isobutyl)(3,5,5-trimethylhexyl) phthalate + 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5) + Di-isononyl phthalate (14103-61-8)

Conditions	Yield
Stage #1: phthalic anhydride; 2-methyl-propan-1-ol at 130℃; for 1h; Stage #2: isononanol; 2-methyl-propan-1-ol; tin oxide at 220℃; under 150.015 Torr; for 7h; Product distribution / selectivity; Dean-Stark trap;

methyl 4-hydroxylbenzoate (99-76-3) → terephthalic acid (100-21-0) + 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5) + phenol (108-95-2) + 4-hydroxy-benzoic acid (99-96-7)

Conditions	Yield
With Ag nanoparticles (NPs) loaded AgBr mesoporous tungsten(VI) oxide composite In water at 20℃; Kinetics; Reagent/catalyst; UV-irradiation;

dichloromethane (75-09-2) + 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5) + titanium tetrachloride (7550-45-0) → tetrachloro(di-iso-butyl o-phthalate)titanium(IV) dichloromethane (130928-30-2)

Conditions	Yield
In hexane (N2); dropwise addn. of di-iso-butyl o-phthalate in n-hexane to TiCl4; stirring; filtn. after 1 h; washed with n-hexane; IR; (1)H NMR;	95%

1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5) → phtalic acid mono-iso-butyl ester (30833-53-5)

Conditions	Yield
With potassium hydroxide In water; dimethyl sulfoxide at 0℃; for 10h; Solvent;	77%
With water; potassium hydroxide In dimethyl sulfoxide at 0℃; for 10h; Solvent;	77%
With Tris-HCl buffer; mouse hepatic microsomal esterase ES46.5K In acetone at 37℃; pH=8.0; Enzyme kinetics; Further Variations:; Reagents; Hydrolysis;

MgCl2. EtOH adduct + 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5) + titanium tetrachloride (7550-45-0) → Reaxys ID: 11558954

Conditions	Yield
at 120℃; for 1.66667h;

MgCl2. EtOH adduct containing water + 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5) + titanium tetrachloride (7550-45-0) → Reaxys ID: 11558955

Conditions	Yield
at 120℃; for 1.66667h;

ethanol (64-17-5) + 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5) + water (7732-18-5) + titanium tetrachloride (7550-45-0) + magnesium chloride (7786-30-3) → Reaxys ID: 11382067

Conditions	Yield
Stage #1: ethanol; water; magnesium chloride at 108℃; for 3h; Stage #2: 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester; titanium tetrachloride at 120℃; for 1.66667h;

phthalic anhydride (85-44-9) + 2-Ethylhexyl alcohol (104-76-7) + 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5) + titanium tetrachloride (7550-45-0) + magnesium chloride → solid catalyst component

Conditions	Yield
Stage #1: 2-Ethylhexyl alcohol; magnesium chloride In decane at 130℃; for 2h; Stage #2: phthalic anhydride In decane at 130℃; for 1h; Stage #3: 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester; titanium tetrachloride more than 3 stages;

1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5) → phtalic acid mono-iso-butyl ester (30833-53-5) + benzene-1,2-dicarboxylic acid (88-99-3)

Conditions	Yield
With recombinant Bacillus subtilis K91 carboxylesterase In methanol; aq. phosphate buffer at 45℃; for 2h; pH=7.5; Kinetics; Enzymatic reaction;

samarium citrate + 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5) → C6H5O7(3-)*Sm(3+)*2C16H22O4

Conditions	Yield
In tetrahydrofuran Reflux;

1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester (84-69-5) + samarium lactate → 3C3H5O3(1-)*Sm(3+)*2C16H22O4

Conditions	Yield
In tetrahydrofuran Reflux;

Upstream product

• 85-44-9 phthalic anhydride 
• 104-76-7 2-Ethylhexyl alcohol 
• 78-83-1 2-methyl-propan-1-ol 
• 3452-97-9 isononanol 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 84-66-2 Diethyl phthalate 

Downstream Products

• 30833-53-5 phtalic acid mono-iso-butyl ester 
• 88-99-3 benzene-1,2-dicarboxylic acid 

Relevant articles and documents

Method for catalyzing esterification reaction of low-carbon alcohol by using ionic liquid

The invention discloses a method for catalyzing low-carbon alcohol esterification reaction by ionic liquid, which comprises the following steps: mixing dianhydride or diacid, fatty alcohol and ionic liquid, heating to 100-160 DEG C by microwave, and reacting for 0.5-2 hours to obtain diester; wherein the ionic liquid is [Ps2TMEDA] [HSO4] 2 and/or [Ps2BPy] [HSO4] 2, the molar ratio of the ionic liquid to the dianhydride or diacid is 0.005-0.04, and the molar ratio of the dianhydride or diacid to the fatty alcohol is 1-5. The method is simple in process, mild in condition, convenient to operate, environment-friendly, high in double esterification degree, high in ionic liquid activity and easy to separate.

Method for preparing diisobutyl phthalate

The invention discloses a method for preparing diisobutyl phthalate. The method comprises the following steps: 1, preparing a magnetic nanoparticle-supported acidic ionic liquid used as a catalyst; and 2, preparing the diisobutyl phthalate: carrying out refluxing dehydration condensation on phthalic anhydride and isobutanol under the catalysis of the magnetic nanoparticle-supported acidic ionic liquid for 3-6 h to obtain a diisobutyl phthalate reaction solution, cooling the reaction solution to room temperature, filtering the cooled reaction solution, adsorbing the obtained filtrate I by a solid alkali, performing filtration to obtain a filtrate II and a filter cake respectively, and carrying out reduced pressure dealcoholysis on the filtrate II to obtain the diisobutyl phthalate. The magnetic nanoparticle-supported acidic ionic liquid is used as the catalyst to achieve catalytic synthesis of the diisobutyl phthalate, so the method has the characteristics of high catalysis efficiency,easiness in recovery and reuse of the catalyst, simple process and less waste water discharge.

Preparation method of diisobutyl phthalate

The invention discloses a preparation method of diisobutyl phthalate. The method comprises the following steps: 1, early stage preparation; 2, esterification reaction; 3, neutralization reaction; 4, dealcoholysis and decolorizing reaction; and 5, press filtration and packaging. In the above technical scheme, phthalic anhydride and isobutanol undergo a reaction with concentrated sulfuric acid as a catalyst to synthesize the diisobutyl phthalate plasticizer. The method has the advantages of simple and controllable process, high reaction efficiency, no byproducts, high output, good economic benefit, short reaction cycle, mild reaction conditions, good industrial application values, satisfactory recycling of wastewater and waste residues, and raw material saving.