1115-20-4

Basic information

• Product Name: NEOPENTYL GLYCOL MONO(HYDROXYPIVALATE)
• Synonyms: NEOPENTYL GLYCOL MONO(HYDROXYPIVALATE);2,2-DIMETHYL-1,3-PROPANEDIOL MONO(HYDROXYPIVALATE);HYDROXYPIVALIC ACID NEOPENTYL GLYCOL ESTER;3-(hydroxypivaloyloxy)-2,2-dimethylpropanol;3-hydroxy-2,2-dimethylpropyl2,2-dimethylhydracrylate;3-hydroxy-2,2-dimethylpropyl3-hydroxy-2,2-dimethylpropionate;3-hydroxy-2,2-dimethylpropylhydroxypivalate;esterdiol204
• CAS NO: 1115-20-4
• Molecular Formula: C₁₀H₂₀O₄
• Molecular Weight: 204.26
• EINECS: 214-222-2
• Mol File: 1115-20-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 46-50°C
• Boiling Point: 292°C
• Flash Point: 292°C
• Appearance: off-white crystals
• Density: 1.01
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.474
• Solubility: Soluble in methanol(almost transparency).
• PKA: 14.15±0.10(Predicted)
• Water Solubility: 239g/L at 25℃
• Sensitive: Hygroscopic
• CAS DataBase Reference: NEOPENTYL GLYCOL MONO(HYDROXYPIVALATE)(CAS DataBase Reference)
• NIST Chemistry Reference: NEOPENTYL GLYCOL MONO(HYDROXYPIVALATE)(1115-20-4)
• EPA Substance Registry System: NEOPENTYL GLYCOL MONO(HYDROXYPIVALATE)(1115-20-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36-41
• Safety Statements: 26-36-39
• TSCA: Yes
• Hazardous Substances Data: 1115-20-4(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H18O5/c1-9(2,5-11)7(13)15-8(14)10(3,4)6-12/h11-12H,5-6H2,1-4H3

Synthetic route

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) → 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + 2,2-Dimethyl-1,3-propanediol (126-30-7)

Conditions	Yield
With sodium hydroxide In water at 30 - 60℃; for 6h; pH=10.5; Reagent/catalyst; Temperature; pH-value; Tishchenko-Claisen Dismutation;	A 80% B 20%

formaline + isobutyraldehyde (78-84-2) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + 2,2-dimethyl-3-hydroxypropyl 2-methylpropionate (5919-84-6) + 2,2-Dimethyl-1,3-propanediol (126-30-7)

Conditions	Yield
With triethylamine at 65 - 90℃; for 0.666667h; Nitrogen atmosphere;	A 62.4% B 2% C 0.26% D 0.64%

ethylmagnesium iodide (10467-10-4) + 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4)

Conditions	Yield
With diethyl ether

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) → 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4)

Conditions	Yield
(i) Et3N, (ii) Ca(OH)2; Multistep reaction;

5,5-dimethyl-2-(1',1'-dimethyl-2'-hydroxyethyl)-4-hydroxy-1,3-dioxane (46329-82-2, 67081-75-8, 67081-77-0, 87194-52-3) → 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4)

Conditions	Yield
barium dihydroxide In various solvent(s) at 32℃; for 0.666667h; Product distribution; Further Variations:; Catalysts; Solvents; Temperatures;

5,5-dimethyl-2-(1',1'-dimethyl-2'-hydroxyethyl)-4-hydroxy-1,3-dioxane (46329-82-2, 67081-75-8, 67081-77-0, 87194-52-3) → 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + C10H19(2)HO4 + C10H19(2)HO4

Conditions	Yield
With monolithio-2,2-dimethyl-1,3-propanediol In tetrahydrofuran at 20℃;

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + 2,2-dimethyl-3-hydroxypropyl 2-methylpropionate (5919-84-6) + 2,2-Dimethyl-1,3-propanediol (126-30-7)

Conditions	Yield
triethylamine at 40 - 90℃; for 0.666667h; Aldol Condensation;

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) → formic acid (64-18-6) + 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + 2,2-Dimethyl-1,3-propanediol (126-30-7)

Conditions	Yield
triethylamine In water Product distribution / selectivity; Aldol Condensation;

formaldehyd (50-00-0) + isobutyraldehyde (78-84-2) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + 2,2-Dimethyl-1,3-propanediol (126-30-7)

Conditions	Yield
With triethylamine In water at 40 - 90℃; for 0.666667h;
With triethylamine In water at 40 - 90℃; for 0.666667h;

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4)

Conditions	Yield
at 40 - 85℃;

2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + nickel (7440-02-0) → neopentylglycol hydroxypivalate carbamate (60653-90-9)

Conditions	Yield
With nitrogen; urea	96%

2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + KOH-solution → 3-Hydroxy-2,2-dimethylpropanoic acid (4835-90-9) + 2,2-Dimethyl-1,3-propanediol (126-30-7)

2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + monolithio-2,2-dimethyl-1,3-propanediol → 3-hydroxy-2,2-dimethyl-propionic acid 3-(3-hydroxy-2,2-dimethyl-propionyloxy)-2,2-dimethyl-propyl ester

Conditions	Yield
In tetrahydrofuran at 25℃; for 24h;

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + Methyl 2,2-dimethyl-3-hydroxypropionate (14002-80-3) + 2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + 2,2-Dimethyl-1,3-propanediol (126-30-7) + isobutyraldehyde (78-84-2) → methyl 3-chloro-2,2-dimethylpropionate (21491-96-3)

Conditions	Yield
With pyridine; calcium hydroxide; formaldehyd; formic acid; thionyl chloride; sodium methylate In methanol

2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate (1115-20-4) + acrylic acid (79-10-7) → C13H22O5

Conditions	Yield
With toluene-4-sulfonic acid; hydroquinone at 80℃; under 300.03 - 450.045 Torr;

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 597-31-9 2,2-dimethyl-3-hydroxypropionaldehyde 
• 50-00-0 formaldehyd 
• 78-84-2 isobutyraldehyde 
• 46329-82-2 5,5-dimethyl-2-(1',1'-dimethyl-2'-hydroxyethyl)-4-hydroxy-1,3-dioxane 

Downstream Products

• 21491-96-3 methyl 3-chloro-2,2-dimethylpropionate 
• 4835-90-9 3-Hydroxy-2,2-dimethylpropanoic acid 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 

Relevant articles and documents

Method for continuously synthesizing neopentyl glycol monoester hydropivalicate by gas phase method

The invention belongs to the field of organic chemistry, and particularly relates to a method for continuously synthesizing neopentyl glycol monoester hydropivalicate by a gas phase method. The methodcomprises the following specific steps: fixing a supported catalyst A on a filler layer of a reaction rectifying tower A, putting formaldehyde and isobutyraldehyde into the reaction rectifying towerA, carrying out heating, and carrying out reacting under catalysis of a catalyst A to generate hydroxyl pivalaldehyde; sending the hydroxyl pivalaldehyde generated in the rectifying tower A to a reaction rectifying tower B from a tower kettle to carry out a reaction to generate a neopentyl glycol monoester hydropivalicate crude product, wherein a supported catalyst B is fixed in the reaction rectifying tower B; and feeding the neopentyl glycol monoester hydropivalicate crude product generated in the rectifying tower B into the rectifying tower C from the tower bottom, carrying out rectification and purification, and extracting the neopentyl glycol monoester hydropivalicate from the tower top. The method improves the yield of the neopentyl glycol monoester hydropivalicate, reduces cost andis worthy of industrial promotion.

Process of producing dioxane glycol

A production method of 2-(5-ethyl-5-hydroxymethyl-1,3-dioxane-2-yl)-2-methylpropane-1-ol (DOG) which includes a step of acetalizing hydroxypivalaldehyde with trimethylolpropane in a solvent in the presence of an acid catalyst. After the acetalization, the reaction product liquid is neutralized and then heated to dissolve the deposited DOG crystals. Then, the reaction product liquid is cooled to recrystallize DOG. DOG produced in such manner has an adequately large particle size. Therefore, DOG is easy to handle and involves little danger of dust explosion.

Method of producing high-purity hydroxypivalaldehyde and/or dimer thereof

The present invention provides a method of producing high-purity hydroxypivalaldehyde and/or dimer thereof, including: reacting isobutyl aldehyde with formaldehyde in a presence of a basic catalyst; distilling a low boiling point component including unreacted isobutyl aldehyde to obtain an aqueous solution; adding a diluent to the aqueous solution; cooling the aqueous solution to crystallize the hydroxypivalaldehyde and/or the dimer thereof; and subjecting the aqueous solution to a solid-liquid separation, followed by washing with an organic solvent and/or water, in which the diluent and a basic compound are added to the aqueous solution containing the hydroxypivalaldehyde and/or the dimer thereof obtained by distilling the low boiling point component off so that a concentration of the hydroxypivalaldehyde and/or the dimer becomes 5 to 23% by mass, the concentration of formaldehyde becomes 0.2 to 2.5% by mass, and a pH value becomes 5.0 or more, the solution is crystallized at a temperature of 20 to 45° C. and subjected to the solid-liquid separation. In this method, handling of a high-viscosity slurry and carrying out any complicated operation such as regeneration of an ion exchange resin are not required, so the high-purity HPA and/or the dimer thereof can be obtained in high yield with an energetically advantageous manner.