10097-02-6

Basic information

• Product Name: 2,2-Bis(hydroxymethyl)butyric acid
• Synonyms: 2,2-DIMETHYLOLBUTYRIC ACID;2,2-BIS(HYDROXYMETHYL)BUTYRIC ACID;2,2-BIS(HYDROXYMETHYL)-N-BUTYRIC ACID;2,2-BIS(HYDROXYMETHYL)BUTANOIC ACID;DimethylolButanoicAcid(Dmba);DimethylolButanoicAcid;2,2-bis-(Hydroxymethyl)-n-buty;Butanoic acid, 2,2-bis(hydroxymethyl)-
• CAS NO: 10097-02-6
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.16
• EINECS: 424-090-1
• Product Categories: Organic acids;Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research;Alcohols;Monomers;Polymer Science;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis
• Mol File: 10097-02-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 109-112 °C(lit.)
• Boiling Point: 360 °C at 760 mmHg
• Flash Point: 185.7 °C
• Appearance: white crystals
• Density: 1.263 g/cm³
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: acetone: 18 wt. % at 40 °C
• PKA: 4.16±0.15(Predicted)
• Water Solubility: 487g/L at 20℃
• CAS DataBase Reference: 2,2-Bis(hydroxymethyl)butyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Bis(hydroxymethyl)butyric acid(10097-02-6)
• EPA Substance Registry System: 2,2-Bis(hydroxymethyl)butyric acid(10097-02-6)

Safety Data

• Hazard Codes: Xi
• Statements: 41-52/53
• Safety Statements: 26-39-61
• WGK Germany: 1
• Hazardous Substances Data: 10097-02-6(Hazardous Substances Data)

Usage

Description

2,2-Bis(hydroxymethyl)butyric acid, also known as THB, is an organic compound with the molecular formula C6H12O4. It is a colorless, odorless liquid at room temperature and is soluble in water. THB is characterized by its two hydroxymethyl groups attached to a butyric acid backbone, which provides it with unique properties and makes it suitable for various applications.

Uses

Used in Water Soluble Polyurethane (PU) Systems:
2,2-Bis(hydroxymethyl)butyric acid is used as a crosslinking agent and hydrophilic agent in the water-soluble PU system. Its ability to form crosslinks enhances the mechanical properties and durability of the PU materials, while its hydrophilic nature improves their compatibility with water-based systems.
Used in Polyester Resin and Epoxy Ester:
THB is utilized as a crosslinking agent in polyester resins and epoxy esters, contributing to the formation of a robust and stable network structure. This results in improved mechanical strength, chemical resistance, and thermal stability of the final products.
Used in Coating Applications:
Due to its good solubility in water, 2,2-Bis(hydroxymethyl)butyric acid is widely used in the coating industry, particularly for water-soluble PU system coatings, adhesives, and leather coating agents. Its incorporation into these formulations enhances the water resistance, adhesion, and overall performance of the coatings.
Used as a Monomer for Water Soluble Polyurethanes and Polyesters:
THB serves as a monomer in the synthesis of water-soluble polyurethanes and polyesters. Its unique structure allows for the creation of polymers with tailored properties, such as hydrophilicity, mechanical strength, and flexibility, making them suitable for a wide range of applications.
Used as an Environmentally Friendly Substitute:
2,2-Bis(hydroxymethyl)butyric acid is considered a new, environmentally friendly alternative to 2,2-Bis(hydroxymethyl)propionic acid. Its use in various applications helps reduce the environmental impact associated with the production and disposal of traditional chemicals.

Flammability and Explosibility

Nonflammable

Synthetic route

3-carboxy-3-ethyl-1,5-dioxaspiro[5.5]undecane → 2,2-bis(hydroxymethyl)butanoic acid (10097-02-6)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol; water at 80℃; for 24h;	93.1%

2,2-dimethylolbutanal (41966-25-0) → 2,2-bis(hydroxymethyl)butanoic acid (10097-02-6)

Conditions	Yield
With dihydrogen peroxide at 50 - 70℃; for 2h; Temperature;	81.6%
With dihydrogen peroxide
With dihydrogen peroxide

formaldehyd (50-00-0) + sodium butyrate (156-54-7) → 2,2-bis(hydroxymethyl)butanoic acid (10097-02-6)

Conditions	Yield
at 150℃; for 70h;

2-phenyl-5-hydroxymethyl-5-ethyl-1,3-dioxacyclohexane (22251-63-4) → 2,2-bis(hydroxymethyl)butanoic acid (10097-02-6)

Conditions	Yield
With potassium permanganate

Upstream product

• 50-00-0 formaldehyd 
• 156-54-7 sodium butyrate 
• 22251-63-4 2-phenyl-5-hydroxymethyl-5-ethyl-1,3-dioxacyclohexane 
• 41966-25-0 2,2-dimethylolbutanal 
• 92016-40-5 α,α-Bis-acetoxymethyl-butyraldehyd 
• 38433-81-7 2-ethyl-3-hydroxypropanal 
• 77-99-6 1,1,1-tri(hydroxymethyl)propane 

Downstream Products

• 934187-86-7 2-[1-(4-chloro-2,6-dimethylphenyl)-6-oxo-1,6-dihydro-3-pyridinyl]-1-(2,4-difluorophenyl)-2-oxoethyl 2,2-bis(hydroxymethyl)butanoate 
• 1252553-70-0 pentafluorophenyl 5-ethyl-2-oxo-1,3-dioxane-5-carboxylate 
• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 1393588-48-1 (3-ethyl-2-oxothietan-3-yl)methyl 4-nitrobenzoate 
• 1609647-70-2 5-ethyl-2,2-dimethyl-[1,3]-dioxane-5-carboxylic acid benzyloxycarbonylmethyl ester 
• 587874-07-5 5-ethyl-2,2-dimethyl-[1,3]-dioxane-5-carboxylic acid 
• 1609647-77-9 C₂₁H₂₈O₁₀ 

Relevant articles and documents

Ab initio structure determination of monoclinic 2,2-dihydroxymethylbutanoic acid from synchrotron radiation powder diffraction data: Combined use of direct methods and the Monte Carlo method

The crystal structure of 2,2-dihydroxymethylbutanoic acid (C6H12O4) in monoclinic form has been determined ab initio from synchrotron radiation powder diffraction data. Two O and five C atoms were first derived by direct methods. Two missing O atoms and one C atom were found by the Monte Carlo method without applying constraint to their relative positions. Positional and isotropic displacement parameters of these non-H atoms were refined by the Rietveld method. Molecules are linked by hydrogen bonds and they make sheet-like networks running parallel to the (010) plane. The Monte Carlo method is demonstrated to be a powerful tool for finding missing atoms in partially solved structure.

Preparation method of 2,2-dimethylolbutyric acid

The invention discloses a preparation method of 2,2-dimethylolbutyric acid; beta, beta-dihydroxymethyl butyraldehyde is produced by reaction of butyraldehyde and polyformaldehyde as raw materials under the action of an organic base catalyst, the beta, beta-dihydroxymethyl butyraldehyde is oxidized under the action of hydrogen peroxide to obtain beta, beta-dihydroxymethyl butyric acid, the beta, beta-dihydroxymethyl butyric acid is neutralized by an inorganic base to obtain beta, beta-dihydroxymethyl butyrate, and the beta, beta-dihydroxymethyl butyrate is distilled and filtered to obtain highpurity beta, beta-dihydroxymethyl butyrate, and finally, the 2,2-dimethylolbutyric acid is obtained by acidification of the high purity beta, beta-dihydroxymethyl butyrate under the action of an acid.The preparation method is characterized in that the 2,2-dimethylolbutyric acid is prepared by a new synthesis method, a recrystallization step in the traditional process is omitted, the reaction efficiency is high, the product is easy to separate, the yield of the product can be greatly improved, the waste is less, and the design idea of green chemistry is met.

Cosmetic or dermatological topical compositions comprising dendritic polyesters

The present invention relates to cosmetic or dermatological compositions capable of being applied to the skin, the keratinous fibers, the nails, the semimucous membranes and/or the mucous membranes, and which includes a dendritic polyester polymer having terminal hydroxyl functional groups or the combination of such a polymer with a film-forming polymer. It also relates to methods of cosmetic or dermatological treatment using these compositions as well as the use of the compositions for the preparation of dermatological or cosmetic compositions.