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Send EmailDibutyl Maleate, DBM, 105-76-0
DIBUTYL MALEATE (DBM)
Dibutyl (Z)-but-2-enedioate - Maleic Acid Dibutyl Ester
CAS: 105-76-0
| Product Name | Dibutyl Maleate (DBM) |
| CAS Number | 105-76-0 |
| EC Number | 203-328-4 |
| Chemical Class | Dicarboxylic Acid Ester |
| Synonyms | Dibutyl Maleate, DBM, Maleic Acid Dibutyl Ester, Dibutyl (Z)-but-2-enedioate |
| Parameter | Description |
|---|---|
| IUPAC Name | Dibutyl (Z)-but-2-enedioate |
| Chemical Formula | C₁₂H₂₀O₄ |
| Molecular Weight | 228.28 g/mol |
| CAS Number | 105-76-0 |
| EC Number | 203-328-4 |
| Synonyms | Dibutyl Maleate, DBM, Maleic Acid Dibutyl Ester, Di-n-butyl Maleate, Dibutylmaleat |
| HS Code | 2917.19.00.00.00 |
| REACH Status | Registered and compliant |
Description: Dibutyl Maleate (DBM) is a diester of maleic acid and butanol. It is a colorless to pale yellow liquid with a mild ester-like odor. It is widely used as a comonomer in vinyl and acrylic emulsion polymerization for paints and adhesives, and as an intermediate and additive in plastics, pigments, pharmaceuticals, and agricultural products.
| Parameter | Description |
|---|---|
| Chemical Family | Dicarboxylic Acid Ester |
| Structure | Maleic acid dibutyl ester (cis-isomer) |
| Functional Groups | Two ester groups (-COO-) |
| C=C Bond | Cis-configured double bond (Z-isomer) |
| SMILES | CCCCOC(=O)C=CC(=O)OCCCC |
| InChI Key | ZWZJZHBIPLOQPP-HWKANZROSA-N |
Structural Formula:
text
O O
|| ||
C₄H₉-O-C-CH=CH-C-O-C₄H₉
Description: Dibutyl Maleate is the dibutyl ester of maleic acid, characterized by a cis-configured carbon-carbon double bond between the two ester groups. This double bond makes DBM a reactive monomer capable of undergoing polymerization reactions. The molecule contains two butyl groups (C₄H₉), giving it good solubility in organic media.
| Parameter | Specification | Test Method |
|---|---|---|
| Appearance | Clear, colorless to pale yellow liquid | Visual Inspection |
| Physical Form | Liquid | Visual Inspection |
| Odor | Mild ester-like odor | Organoleptic |
| Clarity | Clear, free from sediment | Visual Inspection |
Description: Dibutyl Maleate is a clear, colorless to pale yellow liquid with a mild, characteristic ester-like odor. It is supplied as a free-flowing liquid with high purity (>99.0%).
| Property | Specification / Value | Test Method |
|---|---|---|
| Density (20°C) | 0.993 – 0.997 g/cm³ | ASTM D4052 |
| Refractive Index (20°C) | 1.445 – 1.447 | ASTM D1218 |
| Viscosity (25°C) | ~5.0 cP | – |
| Surface Tension | ~30 dyn/cm | – |
Description: DBM is a low-viscosity liquid with density slightly below that of water. Its refractive index and viscosity are typical for dicarboxylic acid esters, making it easy to handle and process in various applications.
| Property | Specification / Value | Test Method |
|---|---|---|
| Melting Point | -85 °C | DSC |
| Freezing Point | -85 °C | DSC |
| Boiling Point | 280 °C | – |
| Boiling Point (760 mmHg) | 280 – 285 °C | – |
| Flash Point (Closed Cup) | > 110 °C | ASTM D93 |
| Auto-ignition Temperature | ~315 °C | – |
| Vapor Pressure (20°C) | < 0.1 mmHg | – |
Description: DBM has a very low freezing point (-85°C) and remains liquid over a wide temperature range. Its high boiling point (280°C) indicates low volatility, making it suitable for high-temperature processing. The flash point above 110°C means it is a combustible liquid but not readily flammable.
| Solvent / Medium | Solubility / Miscibility |
|---|---|
| Water | Insoluble |
| Acetone | Completely miscible |
| Alcohols | Partially miscible |
| Aromatic Solvents | Completely miscible |
| Aliphatic Hydrocarbons | Completely miscible |
| Esters | Completely miscible |
| Ketones | Completely miscible |
| Chlorinated Solvents | Completely miscible |
Description: DBM is insoluble in water but completely miscible with most organic solvents including acetone, aromatic hydrocarbons, aliphatic hydrocarbons, esters, ketones, and chlorinated solvents. This solubility profile allows DBM to be easily incorporated into organic formulations.
| Parameter | Specification | Typical Value | Test Method |
|---|---|---|---|
| Purity (GC) | ≥ 99.0% | 99.5% | GC |
| Water Content (Karl Fischer) | ≤ 0.10% | 0.05% | Karl Fischer |
| Color (APHA) | ≤ 50 | 20 | ASTM D1209 |
| Acid Value (mg KOH/g) | ≤ 0.50 | 0.20 | Titration |
| Di-n-butyl maleate content | ≥ 98.5% | – | – |
| Maleic acid (free) | ≤ 0.02% | – | HPLC |
Description: Dibutyl Maleate is supplied with high purity (>99.0%), low color, and low acid value. Low water content and acid value indicate high quality and product stability. Tight specifications ensure consistent performance in polymerization and synthesis applications.
| Parameter | Description |
|---|---|
| Chemical Stability | Stable under normal conditions |
| Polymerization | Can polymerize with vinyl monomers (styrene, acrylics, vinyl acetate) |
| Hydrolysis | Slow hydrolysis in presence of water/acid (forms maleic acid) |
| Esterification | Reactive with hydroxyl groups (alcohols) |
| Heat Stability | Stable up to ~200°C |
| Polymerization Inhibitors | Typically contains inhibitor (e.g., hydroquinone) to prevent premature polymerization |
Description: DBM is chemically stable under normal conditions but contains a reactive C=C double bond. This makes it an effective comonomer in free-radical polymerization reactions. The product is typically stabilized with small amounts of inhibitor to prevent spontaneous polymerization. Hydrolysis is slow under neutral conditions but is accelerated by acids or bases.
| Reaction Type | Description | Application |
|---|---|---|
| Copolymerization | Copolymerization with vinyl and acrylic monomers | Paints, adhesives, coatings |
| Polymerization | Chain-growth polymerization | Plastic modifiers, elastomers |
| Ester Exchange | Transesterification with other alcohols | Specialty esters |
| Hydrolysis | Hydrolysis to maleic acid and butanol | Intermediate synthesis |
| Michael Addition | Nucleophilic addition to C=C bond | Organic synthesis, fine chemicals |
Description: DBM's primary chemical utility is its ability to undergo polymerization and copolymerization reactions. The reactive double bond and ester functionality allow a wide range of chemical transformations.
| Application | Description / Function |
|---|---|
| Vinyl Emulsion Polymerization | Comonomer for vinyl chloride, vinyl acetate copolymers |
| Acrylic Emulsion Polymerization | Comonomer for acrylic emulsions |
| Automotive Coatings | Improves flexibility and adhesion |
| Industrial Coatings | Provides internal plasticization |
| Architectural Paints | Enhances film flexibility and durability |
| Wood Coatings | Improves adhesion and impact resistance |
| UV-Curable Coatings | Reactive diluent |
Description: DBM is widely used as a comonomer in emulsion polymerization for paints and coatings. It imparts internal plasticization, improving film flexibility, adhesion, and impact resistance without the need for external plasticizers. In UV-curable formulations, it acts as a reactive diluent.
| Application | Description / Function |
|---|---|
| Pressure-Sensitive Adhesives (PSA) | Provides tack and adhesion properties |
| Hot Melt Adhesives | Modifies glass transition temperature |
| Construction Adhesives | Enhances flexibility |
| Packaging Adhesives | Improves adhesion to various substrates |
| Water-Based Adhesives | Comonomer in emulsion polymers |
Description: In adhesive formulations, DBM is used to modify polymer properties. It contributes to improved tack, adhesion to difficult substrates, and enhanced flexibility. Its use in emulsion-based adhesives helps achieve better film formation and bonding strength.
| Application | Description / Function |
|---|---|
| PVC Modification | Internal plasticizer for polyvinyl chloride |
| Vinyl Copolymers | Used in vinyl chloride, vinyl acetate copolymers |
| Acrylic Copolymers | Modifier for acrylic polymers |
| Elastomer Modification | Comonomer for synthetic elastomers |
| Polymer Blends | Improves compatibility |
Description: DBM is used as an internal plasticizer in polymer modification. When copolymerized with vinyl chloride or vinyl acetate, it imparts flexibility, low-temperature performance, and improved processability to the resulting polymers. Unlike external plasticizers, internal plasticizers are chemically bound and cannot migrate.
| Application | Description / Function |
|---|---|
| Pigment Dispersions | Medium for pigment preparation |
| Printing Inks | Modifier for ink resins |
| Pigment Synthesis | Intermediate for pigment production |
| Ink Binders | Comonomer in ink resin formulations |
Description: DBM is used as an intermediate in pigment synthesis and as a modifier in printing ink formulations. It contributes to improved pigment wetting, dispersion, and film properties in ink applications.
| Application | Description / Function |
|---|---|
| Pharmaceutical Intermediates | Synthesis of active pharmaceutical ingredients |
| Drug Delivery | Polymer coatings and excipients |
| Agrochemical Formulations | Solvent and intermediate |
| Pesticide Synthesis | Intermediate for crop protection chemicals |
Description: DBM serves as a versatile chemical intermediate in the pharmaceutical and agricultural industries. Its reactive double bond and ester groups allow further chemical transformations to produce active compounds.
| Application | Description / Function |
|---|---|
| Fine Chemicals | Intermediate for specialty chemicals |
| Michael Reactions | Substrate for nucleophilic additions |
| Diels-Alder Reactions | Dienophile for cycloaddition reactions |
| Polymer Chemistry | Monomer for specialty polymers |
| Flavor and Fragrance | Ester precursor |
Description: In organic synthesis, DBM is a valuable intermediate for fine chemicals, pharmaceuticals, and agrochemicals. Its reactivity as a dienophile in Diels-Alder reactions and as a Michael acceptor makes it useful for constructing complex molecules.
| Certificate / Standard | Status |
|---|---|
| REACH (EC 1907/2006) | Registered and compliant |
| TSCA (USA) | Listed |
| EINECS (EU) | 203-328-4 |
| FDA 21 CFR | Compliant for specific food contact applications |
| GMP | Available upon request |
| Halal / Kosher | Available upon request |
Description: Dibutyl Maleate is registered and compliant with major chemical regulations worldwide including REACH and TSCA. It is listed in EINECS under number 203-328-4. Food contact compliance is available for specific applications.
| Parameter | Description |
|---|---|
| Acute Oral Toxicity (LD50) | ~ 1500 – 2000 mg/kg (rat) |
| Acute Dermal Toxicity | Low – Medium |
| Skin Irritation | Mild irritant |
| Eye Irritation | Moderate irritant |
| Skin Sensitization | Not expected to be sensitizing |
| Inhalation | Mist may cause respiratory irritation |
| Carcinogenicity | Not classified |
| Mutagenicity | Not classified |
| Reproductive Toxicity | Not classified |
Description: Dibutyl Maleate has moderate acute toxicity. It may cause skin and eye irritation upon contact. Inhalation of mist or vapor should be avoided through proper ventilation. It is not classified as a carcinogen or mutagen under standard classifications.
| Parameter | Recommendation |
|---|---|
| Skin Contact | Wash with soap and water |
| Eye Contact | Rinse with plenty of water for 15 minutes; seek medical attention |
| Inhalation | Use in well-ventilated area; organic vapor mask |
| Ingestion | Seek medical attention if large amounts are swallowed |
| Ventilation | Adequate general or local exhaust |
| Gloves | Nitrile or neoprene gloves |
| Eye Protection | Safety goggles |
| Protective Clothing | Chemical-resistant apron |
Description: Standard industrial hygiene practices should be followed when handling Dibutyl Maleate. Good ventilation and appropriate PPE should be used to minimize exposure.
| Parameter | Description |
|---|---|
| Storage Temperature | 10 – 30°C |
| Storage Conditions | Cool, dry, well-ventilated area |
| Container Type | Original sealed containers |
| Materials of Construction | Steel, HDPE, stainless steel |
| Shelf Life | 24 months (unopened, recommended conditions) |
| Stability | Stable under normal conditions |
| Materials to Avoid | Strong oxidizers, bases, acids (heat generation) |
| Inhibitor | Contains inhibitor to prevent polymerization |
| Signs of Degradation | Color darkening, viscosity increase, acid value increase |
Description: Dibutyl Maleate should be stored in cool, dry, well-ventilated areas, away from heat and ignition sources. The product is typically stabilized with an inhibitor to prevent polymerization. Exposure to extreme temperatures should be avoided to prevent quality degradation.
| Parameter | Description |
|---|---|
| Standard Packaging | 200 kg steel drums |
| Bulk Packaging | 1000 kg IBC (available) |
| Small Packaging | 25 kg containers (available upon request) |
| UN Number | Not regulated (typically) |
| Transport Classification | Not classified as dangerous goods |
| Transport Temperature | Ambient temperature |
| Name | Description |
|---|---|
| Dibutyl Maleate | Most common name |
| DBM | Abbreviation |
| Maleic Acid Dibutyl Ester | Systematic name |
| Dibutyl (Z)-but-2-enedioate | IUPAC name |
| Di-n-butyl Maleate | Chemical name |
| Staflex DBM | Trade name |
| RC Comonomer DBM | Trade name |
| Bisomer DBM | Trade name |
| Octomer DBM | Trade name |
| Certificate / Standard | Status |
|---|---|
| ISO 9001:2015 | Certified manufacturing sites |
| REACH (EC 1907/2006) | Registered and compliant |
| TSCA (USA) | Listed |
| EINECS (EU) | 203-328-4 |
Disclaimer: This Technical Data Sheet provides typical values for reference purposes only. All values are based on standard laboratory measurements and do not constitute a binding specification. For binding properties, please request the Certificate of Analysis (COA) for each specific batch. The user is solely responsible for determining product suitability for their intended application and for compliance with all applicable regulations. Safety Data Sheet (SDS) must be requested from the supplier before use.