6846-50-0

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

Downstream Products

• 144-19-4 2,2,4-trimethylpentan-1,3-diol 
• 3494-69-7 5-isobutyryloxy-2,4,4-trimethyl-pent-2-ene 
• 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 

Relevant academic research and scientific papers

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.

Synthesis method for preparing 1,3-diol diester from 1,3-diol monoester

The invention relates to a synthesis method for preparing a 1,3-diol diester from a 1,3-diol monoester. The synthesis method comprises the following steps: in the presence of a catalyst, carrying outa transesterification reaction of the 1,3-diol monoester for 1-3 h at 120-170 DEG C to prepare the 1,3-diol diester and a 1,3-diol, and separating the 1,3-diol diester and the 1,3-diol to obtain the 1,3-diol diester. The catalyst is a benzothiazole ionic liquid, and the benzothiazole ionic liquid is one or more selected from a benzothiazole bisulfate, a benzothiazole phosphate dihydrogen salt, a benzothiazole perchlorate, a benzothiazole nitrate, a 3-(3-sulfonic acid) propyl benzothiazole bisulfate, a 3-(3-sulfonic acid) propyl benzothiazole perchlorate, and a 3-(3-sulfonic acid) propyl benzothiazole phosphate dihydrogen salt. The method adopts the benzothiazole ionic liquid as the catalyst of the transesterification reaction, the catalytic effect is good, and separation of the catalyst issimple and efficient.

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.

Synthetic method of 2, 2, 4-trimethylpentanediol diester

The invention relates to a synthetic method of 2, 2, 4-trimethylpentanediol diester. The synthetic method includes following steps: at presence of a catalyst, allowing 2, 2, 4-trimethylpentanediol monoester to be in transesterification at 120-170 DEG C for 1-3h to obtain 2, 2, 4-trimethylpentanediol diester and 1, 3-diol; separating 2, 2, 4-trimethylpentanediol diester and 1, 3-diol to obtain 2, 2, 4-trimethylpentanediol diester, wherein the catalyst is benzothiazole ion liquid which is selected from one or multiple of benzothiazole hydrosulfate, benzothiazole dihydric phosphate, benzothiazoleperchlorate, benzothiazole nitrate, 3-(3-sulfonic acid) propyl benzothiazole hydrosulfate, 3-(3-sulfonic acid) propyl benzothiazole perchlorate and 3-(3-sulfonic acid) propyl benzothiazole dihydric phosphate. The benzothiazole ion liquid is adopted as the catalyst of transesterification, so that catalytic effect is good; the catalyst is simple and efficient in separation.

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.

Method for directly synthesizing 2,2,4-trimethyl-1,3-pentanediol diisobutyrate from isobutyraldehyde

The invention belongs to the field of fine chemical engineering, and particularly relates to a method for directly synthesizing 2,2,4-trimethyl-1,3-pentanediol diisobutyrate from isobutyraldehyde. According to the method, isobutyraldehyde, as a by-product of an industrial butanol-octanol production process, is taken as a raw material, and 2,2,4-trimethyl-1,3-pentanediol diisobutyrate is directly synthesized. The method comprises the following steps: firstly, conducting aldol condensation and disproportionation-esterification on part of isobutyraldehyde to obtain 2,2,4-trimethyl-1,3-pentanediol isobutyrate; then, conducting oxidization on the remaining unreacted isobutyraldehyde to generate isobutyric acid, wherein separation and purification are not needed; finally, carrying out an esterification reaction to obtain 2,2,4-trimethyl-1,3-pentanediol diisobutyrate. The method has the following advantages: the raw material is cheap and easy to obtain, and can be recycled for several times; the intermediate product needs not be separated and can be directly synthesized into the final product, so as to simplify the technical operation process for generation of the final product; and the raw material conversion rate is high, that is, the isobutyraldehyde conversion rate exceeds 92%.

Preparation method of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate

The invention discloses a preparation method of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate. The preparation method includes the steps that isobutyraldehyde serves as the raw material and is converted into 2,2,4-trimethyl-1,3-pentanediol with a base catalyst, and then, 2,4-trimethyl-1,3-pentanediol is converted into 2,2,4-trimethyl-1,3-pentanediol diisobutyrate with an acid catalyst. The preparation method of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate has the advantages that the material source is wide, the technological process is simple, the conversion rate is high, the product purity is high, and the cost is low.

Method for simultaneous synthesis of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate and 2,2,4-trimethyl-1,3-pentanediol

The present invention relates to the field of fine chemicals, and in particular relates to a method for simultaneous synthesis of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate and 2,2,4-trimethyl-1,3-pentanediol. The 2,2,4-trimethyl-1,3-pentanediol diisobutyrate and the 2,2,4-trimethyl-1,3-pentanediol can be obtained by transesterification of 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate under the effect of an acidic catalyst according to the method. A new method for synthesis of the 2,2,4-trimethyl-1,3-pentanediol diisobutyrate and the 2,2,4-trimethyl-1,3-pentanediol is provided, and according to the situation, product separation can be performed by ordinary distillation or reactive distillation. When the ordinary distillation is used for the product separation, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate conversion rate is 45 to 60%. When the reactive distillation is used for the product separation, the 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate conversion rate is high and can reach 98 to 99%.

Method for preparing 2, 2, 4-trimethyl-1, 3-pentanediol double isobutyric acid ester

The invention discloses a method for preparing 2, 2, 4-trimethyl-1, 3-pentanediol double isobutyric acid ester. The method includes the steps that 1, an alkali metal hydroxide, a phase transfer catalyst and water are mixed in a certain proportion, and isobutyraldehyde is dropwise added slowly; the temperature is raised to 30-50 DEG C after the isobutyraldehyde is dropwise added completely, and heat preservation is conducted for 1-5 hours; 2, the temperature is lowered to room temperature, a water phase is removed, the alkali metal hydroxide is added to an organic phase in a certain proportion, the temperature is raised to 60-70 DEG C, and a heat preservation reaction is conducted for 6-12 hours; 3, the temperature is lowered to the room temperature, the alkali metal hydroxide is removed, and the remaining organic phase is reserved; 4, a certain quantity of isobutyric acid, a solid sulfate catalyst and a water-carrying agent are added to the remaining organic phase, the mixture is heated to 120-150 DEG C, and a heat preservation reaction is conducted for 2-5 hours; after the reaction is completed, filtering is conducted to remove the solid sulfate catalyst, water washing is conducted to remove isobutyric acid which does not participate in the reaction, the water-carrying agent is removed through rotary evaporation, reduced pressure distillation is conducted, and a target product is obtained. Compared with the prior art, by means of the preparation method, the target product is high in yield, the operation process is simple and safe, and industrialized production is achieved easily.

Method for preparing 2,2,4-trimethyl-1,3-pentanediol diisobutyrate from green oxane

The present invention relates to a 2,2,4-trimethyl-1,3-pentanediol diisobutyrate preparation method, particularly to a method for preparing 2,2,4-trimethyl-1,3-pentanediol diisobutyrate from green oxane. According to the present invention, green oxane (2,4-diisopropyl-5,5-dimethyl-1,3-dioxane) and isobutyric acid are adopted as raw materials, a fixed bed continuous catalytic cracking and esterification reaction is performed by using a solid acid catalyst, the generated water and the generated isobutyraldehyde are subjected to azeotropic distillation removal, the unreacted green oxane and the unreacted isobutyric acid light component are removed and recovered through a light removal tower, and rectification is performed through a rectification tower to obtain the 2,2,4-trimethyl-1,3-pentanediol diisobutyrate. According to the present invention, with the method, the continuous production of the 2,2,4-trimethyl-1,3-pentanediol diisobutyrate through catalytic cracking and esterification of green oxane is achieved, the process is simple, the process is clean, the yield is high, and the great large-scale industrial application value is provided.