6846-50-0

Basic information

• Product Name: 2,2,4-TRIMETHYL-1,3-PENTANEDIOL DIISOBUTYRATE
• Synonyms: TEXANOL ISOBUTYRATE;PROSOLVE DE;2,2,4-TRIMETHYL-1,3-PENTANEDIOL BIS(ISOBUTYRATE);2,2,4-TRIMETHYL-1,3-PENTANEDIOL DIISOBUTYRATE;2,2,4-TRIMETHYL-1,3-PENTANEDIOL-ISOBUTYRATE;2,2,4-TRIETHYL-1,3-PENTANEDIOL DIISOBUTYRATE;1,3-Pentanediol, 2,2,4-trimethyl-, diisobutyrate;2,2,4-Trimethylpentanediol-1,3-diisobutyrate
• CAS NO: 6846-50-0
• Molecular Formula: C₁₆H₃₀O₄
• Molecular Weight: 286.41
• EINECS: 229-934-9
• Product Categories: Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks
• Mol File: 6846-50-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: −70 °C(lit.)
• Boiling Point: 280 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless/Liquid
• Density: 0.941 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00388mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Explosive Limit: 0.48%, 172°F
• Water Solubility: 13mg/L at 25℃
• Merck: 14,9251
• CAS DataBase Reference: 2,2,4-TRIMETHYL-1,3-PENTANEDIOL DIISOBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,4-TRIMETHYL-1,3-PENTANEDIOL DIISOBUTYRATE(6846-50-0)
• EPA Substance Registry System: 2,2,4-TRIMETHYL-1,3-PENTANEDIOL DIISOBUTYRATE(6846-50-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• RTECS: SA1420000
• Hazardous Substances Data: 6846-50-0(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLORLESS LIQUID

Uses

Different sources of media describe the Uses of 6846-50-0 differently. You can refer to the following data:
1. Plasticizer.
2. 2,2,4-Trimethyl-1,3-pentanediol Diisobutyrate is a plastic additivea and was found to associate with newly diagnosed asthma.
3. In manufacture of vinyl flooring, toys and other vinyl products.

General Description

2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate (TMPD-MIB), a volatile organic compound (VOC), is an important component found in water-based paints, printing inks, and anti-freeze agents. TMPD-MIB is a non-phthalate alternate plasticizer used in polyvinyl chloride plastics. Its detection in polystyrene and polypropylene cups used for food packing has been investigated.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C16H30O4/c1-10(2)13(20-15(18)12(5)6)16(7,8)9-19-14(17)11(3)4/h10-13H,9H2,1-8H3/t13-/m1/s1

Synthetic route

2,2,4-trimethylpentan-1,3-diol (144-19-4) + isobutyryl chloride (79-30-1) → 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0)

Conditions	Yield
With zinc(II) chloride In dichloromethane at 0 - 40℃; Molecular sieve;	85.2%

texanol (77-68-9) + isobutyric Acid (79-31-2) → 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0)

Conditions	Yield
Stage #1: texanol; isobutyric Acid With dmap; thionyl chloride In acetonitrile at -15 - -5℃; for 1h; Stage #2: at 100℃; for 1h; Reagent/catalyst;	90%
With sulfuric acid; 3-(3-sulfonic acid propyl)benzothiazole dihydrogen phosphate In dichloromethane at 50℃; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Microwave irradiation;	89%
With sodium hydrogen sulfate In toluene at 120℃; for 5h; Reagent/catalyst; Temperature; Industrial scale;
With sodium hydroxide at 110 - 165℃; for 2h; Reagent/catalyst;

texanol (77-68-9) → 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0)

Conditions	Yield
With benzothiazole-nitrate ionic liquid at 140℃; for 2h; Reagent/catalyst;	88.1%

texanol (77-68-9) + isobutyraldehyde (78-84-2) → 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0)

Conditions	Yield
With CrO2.SO3 at 180℃; for 8h; Reagent/catalyst;	95%

texanol (77-68-9) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0)

Conditions	Yield
With Cr2O3/SO42 solid acid catalyst at 160℃; for 6h; Reagent/catalyst; Temperature;	A n/a B 93%

2,4-diisopropyl-5,5-dimethyl-1,3-dioxane (3494-76-6) + isobutyric Acid (79-31-2) → 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0)

Conditions	Yield
at 110℃; Temperature; Industrial scale;	92%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + isobutyric Acid (79-31-2) → 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0)

Conditions	Yield
With toluene-4-sulfonic acid In chloroform
at 110℃; for 5h; Concentration; Temperature;

isobutyraldehyde (78-84-2) → texanol (77-68-9) + 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0) + 2-methylpropionic acid 3-hydroxy-2,2-dimethyl-1-(1-methylethyl)propyl ester (18491-15-1)

Conditions	Yield
O2W(1-)*Li(1+) In tetrahydrofuran at 40℃; for 24h; variation of temperature; Yields of byproduct given;	A n/a B 38% C n/a
O2W(1-)*Li(1+) In tetrahydrofuran at 40℃; for 24h; Product distribution; Mechanism; variation of temperature;	A n/a B 38 % Chromat. C n/a

isobutyraldehyde (78-84-2) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + texanol (77-68-9) + 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0) + 2-methylpropionic acid 3-hydroxy-2,2-dimethyl-1-(1-methylethyl)propyl ester (18491-15-1) + isobutyric Acid (79-31-2)

Conditions	Yield
With sodium hydroxide In water at 60℃; for 4h; Concentration; Overall yield = 63.6 %Chromat.;

2,2,4-trimethylpentan-1,3-diol (144-19-4) + isobutyraldehyde (78-84-2) → texanol (77-68-9) + 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0) + 2-methylpropionic acid 3-hydroxy-2,2-dimethyl-1-(1-methylethyl)propyl ester (18491-15-1)

Conditions	Yield
Stage #1: 2,2,4-trimethylpentan-1,3-diol With n-butyllithium In tetrahydrofuran Inert atmosphere; Stage #2: isobutyraldehyde In tetrahydrofuran for 0.533333h; Solvent; Reagent/catalyst; Inert atmosphere;

2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0) → 2,2,4-trimethyl-pent-3-en-1-ol (5842-53-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 500 °C 2: NaOH / ethane-1,2-diol View Scheme
Multi-step reaction with 2 steps 1: 500 °C 2: aq. NaOH / methanol View Scheme

2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0) → isobutyric acid-(2,2,4-trimethyl-pentyl ester) (36679-74-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 500 °C 2: H2 / Raney-Ni / dioxane View Scheme

2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0) → 2,2,4-trimethylpentan-1,3-diol (144-19-4)

Conditions	Yield
With sodium hydroxide In methanol

2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0) → 5-isobutyryloxy-2,4,4-trimethyl-pent-2-ene (3494-69-7)

Conditions	Yield
at 500℃;

2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0) → 1,3-diacetoxy-2,2,4-trimethyl-pentane (4100-09-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / methanol 2: TsOH*H2O / CHCl3 View Scheme

2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0) → 2,2,4-trimethyl-1,3-pentanediol, diformate (5451-59-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / methanol 2: TsOH*H2O / CHCl3 View Scheme

Upstream product

• 144-19-4 2,2,4-trimethylpentan-1,3-diol 
• 79-30-1 isobutyryl chloride 
• 77-68-9 texanol 
• 78-84-2 isobutyraldehyde 
• 79-31-2 isobutyric Acid 
• 3494-76-6 2,4-diisopropyl-5,5-dimethyl-1,3-dioxane 

Downstream Products

• 5451-59-2 2,2,4-trimethyl-1,3-pentanediol, diformate 
• 4100-09-8 1,3-diacetoxy-2,2,4-trimethyl-pentane 
• 36679-74-0 Isobuttersaeure-<2,2,4-trimethyl-pentyl-(1)>-ester 
• 5842-53-5 2,2,4-trimethyl-pent-3-en-1-ol 
• 3494-69-7 5-isobutyryloxy-2,4,4-trimethyl-pent-2-ene 
• 144-19-4 2,2,4-trimethylpentan-1,3-diol 

Relevant articles and documents

Di-esterification synthesis method of 1,3-glycol

The invention relates to a di-esterification synthesis method of 1,3-glycol. The synthesis method comprises the following steps: in the presence of a catalyst, performing a transesterification reaction on a 1,3-glycol monoester at 120-170 DEG C for 1-3 hours so as to prepare a 1,3-glycol diester and 1,3-glycol; and separating the 1,3-glycol diester from the 1,3-glycol, so as to obtain a 1,3-glycoldiester, wherein the catalyst is a benzothiazole ionic liquid. The benzothiazole ionic liquid is selected from one or more of benzothiazole disulfate, benzothiazole dihydric phosphate, benzothiazoleperchlorate, benzothiazole nitrate, 3-(3-sulfonic acid) propylbenzene benzothiazole disulfate, 3-(3-sulfonic acid) propyl benzothiazole perchlorate and 3(3-sulfonic acid) propyl benzothiazole dihydricphosphate. As a benzothiazole particle liquid is adopted as the catalyst of the transesterification reaction, the method has a very good catalysis effect, and the catalyst is simple and efficient toseparate.

Method for synthesizing 1,3-diol diester by microwave reaction

The invention relates to a method for synthesizing 1,3-diol diester by a microwave reaction. The synthetic method comprises the following steps: allowing 1,3-diol monoester to generate a transesterification reaction at 120 to 170 DEG C in the presence of a catalyst for 1 to 3 hours so as to prepare the 1,3-diol diester and 1,3-diol; and separating the 1,3-diol diester from the 1,3-diol so as to obtain the 1,3-diol diester; wherein the catalyst is a benzothiazole ionic liquid which is one or more selected from the group consisting of benzothiazole hydrogen sulfate, benzothiazole dihydrogen phosphate, benzothiazole perchlorate, benzothiazole nitrate, 3-(3-sulfonic acid)propyl benzothiazole hydrogen sulfate, 3-(3-sulfonic acid)propyl benzothiazole perchlorate and 3-(3-sulfonic acid)propyl benzothiazole dihydrogen phosphate. According to the invention, by adoption of the benzothiazole ionic liquid as the catalyst for the transesterification reaction, good catalytic effect is achieved; meanwhile, the catalyst is simple and highly-efficient to separate.

Method for preparing 2,2,4-trimethyl-1,3-pentanediol bisisobutyrate

The invention discloses a method for preparing 2,2,4-trimethyl-1,3-pentanediol bisisobutyrate. The method is characterized by using 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate and isobutyric acid as raw materials through an esterification reaction under an alkaline condition. The method has the advantages of easily controllable reaction process, less catalyst usage amount, short reaction time, high reactant conversion rate, and applicability to industrial production.