Dibutyl maleate

Dibutyl maleate

Dibutyl maleate

Dibutyl maleate = DBM = Maleic acid dibutyl ester

Preferred IUPAC name: Dibutyl (2Z)-but-2-enedioate

CAS Number: 105-76-0
EC Number: 203-328-4
Mol. formula: C12H20O4

SYNONYMS
di-n-butyl maleate; maleic acid, di-n-butyl ester; maleic acid dibutyl ester; 2-butenedioic acid (cis) di-n-butyl ester; 2-butenedioic acid (cis) dibutyl ester; 2-butenedioic dibutyl ester; butyl maleate

IUPAC names
1,4-dibutyl (2Z)-but-2-enedioate
2-Butenedioic acid (Z)-,dibutyl ester
Di-n-butyl maleate
dibutyl (E)-but-2-enedioate
dibutyl (Z)-but-2-enedioate
dibutyl but-2-enedioate
Dibutyl maleate
dibutyl maleate
Dibutyl Maleate
dibutyl maleate

Trade names
2-Butendisaeure (Z)-
2-Butenedioic acid (Z)-, dibutyl ester
DBM
Di-n-butyl maleinate
Dibutyl maleate
Dibutyl-ester
Dibutylmaleinat
Maleic acid, dibutyl ester
Maleinsaeure-di-n-butylester
Maleinsaeuredibutylester

Maleic acid dibutyl ester (DBM) is a suitable intermediate for use in the production of paints and adhesives, copolymers and films.
As co-monomer used with Vinyl acetate (VAM) in emulsion polymers (latexes) DBM leads to the following performance improvements:

Lower the glass transition temperature (Tg) and the minimum film forming temperature (MFFT)
Reduce the excessive hardness and brittleness of VAM homopolymers
Improve flexibility of the final films
Improve the hydrolytic stability
To reduce the Tg of a VAM based latex to 7°C, about 25 % of DBM related to VAM is used. DBM can be a substitute for Acrylates Estes or VeoVa esters as co-monomers.
Maleic acid dibutyl ester permits the addition reactions normally possible with compounds having olefinic double bonds and is suitable, for example, as a dienophile for diene syntheses using the Diels-Alder reaction.
By hydrogenation or acetylation, valuable intermediates can be obtained, e.g. derivatives of succinic acid, which are employed in many different areas of organic synthesis.

Dibutyl maleate is a colorless liquid with a characteristic “ester” odor.
Dibutyl maleate is used as a comonomer in vinyl and acrylic emulsion polymerization for paints and adhesives.
Dibutyl maleate is also a suitable intermediate for use in organic synthesis, e.g. in the production of derivatives of succinic acid.

Dibutyl Maleate (DBM) is a colorless, liquid plasticizer for vinyl resins, and is used for copolymers applications involving PVC and vinyl acetates.
Dibutyl Maleate is an unsaturated ester which is used for creating sulfosuccinate surfactants in detergents and paints.
Dubutyl Maleate is also used as a comonomer in paints and adhesives for vinyl and acrylic emulsion polymerization.
Other applications of DBM include use in plastisols, dispersions, coatings, adhesives, and synthetic lubricants.

Dibutyl Maleate is used as an additive and intermediate for plastics, pigments, pharmaceuticals,and agricultural products manufacturing.
Dibutyl Maleate is an intermediate for the production of paints, adhesives and copolymers.
Dibutyl Maleate is used in many organic synthesis including as a dienophile for diene syntheses

Dibutyl maleate is an organic compound with the formula (CHCO2Bu)2 (Bu = butyl).
Dibutyl maleate is the diester of the unsaturated dicarboxylic acid maleic acid.
Dibutyl maleate is a colorless oily liquid, although impure samples can appear yellow.

Dibutyl Maleate (DBM) is also known as Maleic Acid or Dibutylester. It is a colorless, oily and liquid substance. It has a characteristic ester-like odor. Dibutyl Maleate is insoluble in water and is considered combustible.

DBM is commonly used in the paint industry as a comonomer in vinyl and acrylic emulsion polymerization for various adhesives and paints.
DBM is also used as an intermediate in organic synthesis, for example in the production of derivatives of succinic acid.
Another common application is DBM’s use as a plasticizer in water resistant films.
Other applications of DBM include use in plastisols, dispersions, coatings, adhesives, and synthetic lubricants.

MARKET INFORMATION OF DIBUTYL MALEATE:
Dibutyl Maleate is also called as Maleic Acid or Dibutyl ester is a colorless liquid with an ester-like odor.
Dibutyl Maleate is used as an intermediate for the production of inks and coatings application.
Dibutyl Maleate is used in the manufacturing of paints to give it high flexibility, stability to water and ultra-violate light, besides a higher adherence.
Growing construction activities in developing countries has been boosting the demand of Dibutyl Maleate for paints and coatings in recent times.
This increasing demand for coatings is expected to boost the demand for Dibutyl Maleate in coatings applications in coming years.

Preparation
Dibutyl maleate can be prepared by the reaction of maleic acid anhydride and 1-butanol in presence of p-toluenesulfonic acid.

Uses
Dibutyl maleate is mainly used as a plasticizer for aqueous dispersions of copolymers with vinyl acetate and as an intermediate in the preparation of other chemical compounds.
With the invention of polyaspartic technology the material found another use.
In this situation, an amine is reacted with a dialkyl maleate – usually diethyl maleate but also dibutyl maleate may be used- utilizing the Michael addition reaction.
The resulting products, polyaspartic esters products are then used in coatings, adhesives, sealants and elastomers.

DBM is used in various resins and in the preparation of emulsions for the paper industry, textile and lubricant additives.

DBM is also a suitable intermediate for use in organic synthesis, in the production of derivatives of succinic acid.

Dibutyl Maleate is used for creating sulfosuccinate surfactants in detergents and paints.

DBM offers excellent rheological properties, and it can improve adhesion, flexibility and waterproofing in inks and paints. It also improves the UV filtration power.

Hydrophobicity and water resistance of the PVAc latex films were increased by using DBM as comonomer.

It is used in synthesis resin and dope material, and is used in petroleum industry, fabric, plastic, and paper industrial dipping agent, dispersive agent, adhesive, accelerant, pesticide, surface active agent and others.

Market Segmentation by Application, the market is categorized into:

Inks & Coatings
Chemical Intermediate
Plasticizers
Adhesives
Others (Synthetic Lubricants etc.)

Properties
Chemical formula: C12H20O4
Molar mass: 228.288 g·mol−1
Appearance: Colorless to yellowish liquid with a characteristic odor
Density: 0.99 g·cm−3
Melting point: −85 °C (−121 °F; 188 K)
Boiling point: 280 °C (536 °F; 553 K)
Solubility in water: Very hardly soluble (0.17 g·l−1 at 20 °C)
Vapor pressure: 0.0027 hPa (20 °C)
Refractive index (nD): 1.445 (20 °C)

Industry Uses:
Adhesives and sealant chemicals
Corrosion inhibitors and anti-scaling agents
Finishing agents
Fuels and fuel additives
Intermediates
Paint additives and coating additives
Surface active agents

Dibutyl maleate is widely used as a plasticizer in vinyl resins.
About 90% of the global plasticizers produce are used for the manufacturing of PVC as plasticizers improve flexibility and durability.
Dibutyl maleate is used in paints to improve the stability of paint towards water & ultraviolet light.
The demand for DBM from the paints & coating industry is expected to grow as demand for water-resistant paints & coatings is increasing.
The construction projects in developing economies will also further increase the demand for such paints & coatings.

Dibutyl maleate is now being used in the cosmetic industry as well. It acts as an SPF enhancer in skincare products and hair flexibility & gloss enhancer in hair products.
Dibutyl maleate is used as a co-monomer with vinyl acetate monomer in polymer emulsion to improve the properties. It reduces the hardness and brittleness in resulting polymers.

Dibutyl maleate is used as a co-monomer in acrylic emulsions for the manufacturing of various adhesives and resins including food-grade additives.
Dibutyl maleate is also used as an intermediate in the production of derivatives of succinic acid, whose global production is expected to grow over 10% annually.
Dibutyl maleate is also used as an intermediate in the pharmaceutical industry.

Hazards
GHS pictograms
GHS07: Exclamation mark
GHS08: Health hazard
GHS09: Environmental hazard
GHS hazard statements    H317, H373, H411
GHS precautionary statements    P273, P280, P302+P352, P314
Flash point: 141 °C (286 °F; 414 K)
Autoignition temperature: 265 °C (509 °F; 538 K)
Explosive limits
Lower limit: 0.5 vol-%
Upper limit: 3.4 vol-%
Lethal dose or concentration (LD, LC):
LD50 (median dose): 3700 mg·kg−1 (rat, oral) 10000 mg·kg−1 (rabbit, dermal)

Synonyms:
2-butene dioic acid dibutyl ester
2-butenedioic acid (2Z)-, dibutyl ester
2-butenedioic acid (Z)-, dibutyl ester
(Z)-2-butenedioic acid dibutyl ester
2-butenedioic acid, dibutyl ester, (2Z)-
2-butenedioic acid, dibutyl ester, (Z)-
dibutyl (2Z)-2-butenedioate
dibutyl (2Z)-but-2-enedioate
dibutyl (Z)-but-2-enedioate
dibutylmaleate
maleic acid dibutyl ester
maleic acid, dibutyl ester

DIBUTYL MALEATE
105-76-0
Butyl maleate
Staflex DBM
RC Comonomer DBM
dibutyl (Z)-but-2-enedioate
Maleic acid, dibutyl ester
Maleic Acid Dibutyl Ester
di-n-Butyl maleate
2-Butenedioic acid (Z)-, dibutyl ester
2-Butenedioic acid, dibutyl ester
2-Butenedioic acid (2Z)-, dibutyl ester
UNII-4X371TMK9K
Dibutylmaleate
PX-504
Dibutylester kyseliny maleinove
MFCD00009447
4X371TMK9K
2-Butenedioic acid (2Z)-, 1,4-dibutyl ester
Dibutyl maleate, 97%
DBM (VAN)
CCRIS 4136
NSC 6711
EINECS 203-328-4
Dibutylester kyseliny maleinove [Czech]
BRN 1726634
Bibutyl maleate
AI3-00644
dibutyl (2Z)-but-2-enedioate
Bisomer DBM
Octomer DBM
Maleic acid dibutyl
maleic acid-dibutylester
Dibutyl maleate, 96%
Di-n-butylmaleate (DBM)
DSSTox_CID_6724
bis-(2-Ethylhexyl)maleate
EC 203-328-4
DSSTox_RID_78199
DSSTox_GSID_26724
SCHEMBL28153
maleic acid di-n-butyl ester
MLS000515953
WLN: 4OV1U1VO4-C
METHYL10-BROMODECANOATE
DBM, Maleic acid dibutyl ester
CHEMBL1466826
DTXSID3026724
Dibutyl (2Z)-2-butenedioate #
NSC6711
HMS2270N17
ACN-S002423
NSC-6711
Tox21_200779
SBB060326
dibutyl (2Z)but-2-ene-1,4-dioate
AKOS015950672
ZINC100004209
2-Butenedioic acid, dibutyl ester, cis-
NCGC00164013-01
NCGC00164013-02
NCGC00258333-01
CAS-105-76-0
I806
SMR000112422
2-Butenedioic acid, dibutyl ester, (2Z)-
M0009
W-108779
Q27260622
2-Butenedioic acid (2Z)-, 1,4-dibutyl ester, homopolymer
29014-72-0

Dibutyl maleate
EC Inventory: dibutyl maleate

CAS names: 2-Butenedioic acid (2Z)-, 1,4-dibutyl ester

(2Z)-2-Butènedioate de dibutyle [French] [ACD/IUPAC Name]
105-76-0 [RN]
203-328-4 [EINECS]
2-Butenedioic acid, dibutyl ester, (2Z)- [ACD/Index Name]
Dibutyl (2Z)-2-butenedioate [ACD/IUPAC Name]
Dibutyl (2Z)-but-2-enedioate
Dibutyl maleate
Dibutyl-(2Z)-2-butendioat [German] [ACD/IUPAC Name]
MFCD00009447 [MDL number]
ON0875000
(E)-2-Butenedioic acid dibutyl ester
(Z)-2-Butenedioic acid dibutyl ester
(Z)-but-2-enedioic acid dibutyl ester
[105-76-0]
105-75-9 [RN]
2-Butenedioic acid (2Z)-, 1,4-dibutyl ester
2-Butenedioic acid (2Z)-, dibutyl ester
2-Butenedioic acid (Z)-, dibutyl ester
2-Butenedioic acid, dibutyl ester, (Z)-
2-Butenedioic acid, dibutyl ester, cis-
Bibutyl maleate
bis-(2-Ethylhexyl)maleate
Bisomer DBM
Butyl maleate
dbm
DBM, Maleic acid dibutyl ester
dibutyl (2Z)but-2-ene-1,4-dioate
dibutyl (Z)-but-2-enedioate
dibutyl maleate, 97%
dibutyl maleate,99%
Dibutyl(2Z)-2-butenedioate
Dibutylester kyseliny maleinove
Dibutylmaleate
di-n-Butyl maleate
di-n-butyl maleate, 96%
Di-n-butylmaleate (DBM)
Jsp000537
maleic acid dibutyl ester
MALEIC ACID, DIBUTYL ESTER
NCGC00164013-01
Octomer DBM
RC Comonomer DBM
Staflex DBM
WLN: 4OV1U1VO4-C
马来酸二丁酯

Other names: Maleic acid, dibutyl ester; Butyl maleate; Dibutyl maleate; DBM; RC Comonomer DBM; Staflex DBM; di-n-Butyl maleate; Bibutyl maleate; 2-Butenedioic acid, dibutyl ester, cis-; Dibutylester kyseliny maleinove; Bisomer DBM; Octomer DBM; PX-504; 2-Butenedioic acid (2Z)-, 1,4-dibutyl ester; 2-Butenedioic acid (2Z)-, dibutyl ester; Dibutyl (2z)-2-butenedioate

DBM is miscible with methanol, ethanol, acetone, diethyl ether, N,N-dimethyl formamide and toluene.

DBM is not miscible with aliphatic hydrocarbons and is slightly miscible with water.

Butyl maleates are ester compounds with a wide range of properties.
There are 5 main derivatives of butyl maleate :
Monobutyl maleate, Di isobutyl maleate, Allyl Butyl maleate, Di-n-butyl Maleate, and Di-tert-butyl maleate.
These derivatives have a wide range of applications, not limiting to, from the polymer industry to the pharmaceutical industry.

Dibutyl maleate popularly known as DBM is the most widely used compound among butyl maleates.
It is a synthetic colorless organic chemical with a characteristic odor.
Dibutyl maleate is mainly used in the manufacturing of adhesives, paints, copolymers & films, finishing agents, and cosmetics.
The global market is expected to increase as the production of polymers & other derivatives of dibutyl maleate are increasing.

The global demand for dibutyl maleate is expected to increase, with the paints and coatings industry contributing to the maximum growth.
There is a significant increase in heat-resistant paints as global temperature levels are rising due to a number of reasons including global warming.
The demand for dibutyl maleate from Southeast Asia is expected to grow rapidly for the production of paints and polymers due to the increase in construction projects.
The implementation of strict rules relating to the use of VOCs in the production of paints will further result in rising demand for the production of dibutyl maleate.

The increasing production of plasticizers will also drive the demand in the global market.
The demand from the cosmetic industry is also increasing as dibutyl maleate when mixed with other chemical agents in appropriate proportions is finding new applications in skin & hair care.
Contrary, the demand from pharmaceutical industries is not expected to rise much as dibutyl maleate has limited application in the pharmaceutical industry.
There are very few international players in the market. However, China dominates the market of dibutyl maleate in the Asia Pacific region.

Dibutyl maleate (DBM) Market: Segmentation
On the basis of derivatives of dibutyl maleate (DBM), the market can be categorized into:

Di-n-butyl Maleate (Di(n-butyl) itaconate)
Di- isobutyl maleate (maleic acid diethyl ester)
Di-tert-butyl maleate
On the basis on applications, the market can be segmented into:

Polymer industry
Cosmetic industry
Pharmaceutical industry
Paints and coating industry
Healthcare
On the basis of physical nature, the market is segmented into:

Dry powdered Dibutyl maleate
Liquid Dibutyl Maleate
On the basis of product grades, the market is segmented into:

Technical grade
Industrial grade
Pharmaceutical grade