Examples of DICARBOXYLIC ESTERS
-DEHYLUB® 4039 Di(2-Ethylhexyl) Azelate ( Cas No: 103-24-2)
-DEHYLUB® 4005 Di(2-Ethylhexyl) Sebacate ( Cas No: 122-62-3)
-DEHYLUB® 4045 Di-isodecyl Adipate ( Cas No: 27178-16-1)
-DEHYLUB® 1337 Di-isotridecyl Adipate ( Cas No: 26401-35-4)
Dicarboxylic acids and their derivatives (esters and anhydrides) have been used as acylating agents in lipase-catalyzed reactions in organic solvents.
The synthetic outcomes have been dimeric or hybrid derivatives of bioactive natural compounds as well as functionalized polyesters.
A dicarboxylic ester is an organic compound containing two carboxyl functional groups (−COOH).
The general molecular formula for dicarboxylic esters can be written as HO2C−R−CO2H, where R can be aliphatic or aromatic.
In general, dicarboxylic esters show similar chemical behavior and reactivity to monocarboxylic acids.
Dicarboxylic esters are also used in the preparation of copolymers such as polyamides and polyesters.
Dicarboxylic esters are organic compounds containing two carboxylic acid functional groups.
Dicarboxylic esters generally show the same chemical behavior and reactivity as monocarboxylic acids.
The ionization of the second carboxyl group occurs less readily than the first one, because more energy is required to separate a positive hydrogen ion from the anion than from the neutral molecule.
Dicarboxylic ester has the potential alternative as plasticizer which environmentally friendly in polymeric formulation especially for poly (vinyl chloride) (PVC).
Dicarboxylic ester compounds were synthesized via esterification between dicarboxylic acid and 2-ethyl-1-hexanol by using sulfuric acid as catalyst.
The effects of reaction parameters were studied by optimizing temperature, mole ratio of reactants, amount of catalyst and reaction to obtain highest ester conversion.
The optimum results showed Dicarboxylic ester successfully converted to the dicarboxylate ester at parameters; 4 hours; 120 °C; catalyst amount: 2%
Dicarboxylic esters are organic compounds that are substituted with two carboxylic ester functional groups.
In molecular formulae for dicarboxylic esters, these groups are often written as HOOC-R-COOH, where R is usually an alkyl, alkenyl, or akynyl group.
Dicarboxylic esters can be used to prepare copolymers such as nylon and polyethylene terephthalate.
Dicarboxylic esters do not occur in appreciable amounts as components of animal or vegetal lipids, they are in general important metabolic products of fatty acids since they originate from them by oxidation.
Dicarboxylic esters are suitable substrates for preparation of organic acids for the pharmaceutical and food industries.
Furthermore, they are useful materials for the preparation of fragrances, polyamides, adhesives, lubricants, and polyesters.
The dicarboxylic ester glutarate is an important building-block gaining interest in the chemical and pharmaceutical industry.
First aid measures of DICARBOXYLIC ESTERS
Provide fresh air.
In all cases of doubt, or when symptoms persist, seek medical advice.
Following skin contact
After contact with skin, wash immediately with plenty of water.
Immediate medical treatment required because corrosive injuries that are not treated are hard to cure.
Following eye contact
In case of contact with eyes flush immediately with plenty of flowing water for 10 to 15 minutes holding eyelids apart and consult an ophthalmologist.
Protect uninjured eye.
Rinse mouth immediately and drink plenty of water.
Call a physician immediately.
If swallowed danger of perforation of the esophagus and the stomach (strong corrosive effects).
Handling and storage of DICARBOXYLIC ESTERS
Precautions for safe handling
Handle and open container with care.
Avoid dust formation.
Clear contaminated areas thoroughly.
Measures to prevent fire as well as aerosol and dust generation
Removal of dust deposits.
Advice on general occupational hygiene
Wash hands before breaks and after work.
Keep away from food, drink and animal feedingstuffs.
Conditions for safe storage, including any incompatibilities
Store in a dry place.
Keep in a cool place.
Incompatible substances or mixtures
Observe hints for combined storage.
Consideration of other advice:
Use local and general ventilation.
Dicarboxylic esters are crystalline solids.
Solubility in water and melting point of the α,ω- compounds progress in a series as the carbon chains become longer with alternating between odd and even numbers of carbon atoms, so that for even numbers of carbon atoms the melting point is higher than for the next in the series with an odd number.
These compounds are weak dibasic acids with pKa tending towards values of ca. 4.5 and 5.5 as the separation between the two carboxylate groups increases.
Thus, in an aqueous solution at pH about 7, typical of biological systems, the Henderson–Hasselbalch equation indicates they exist predominantly as dicarboxylate anions.
The dicarboxylic esters, especially the small and linear ones, can be used as crosslinking reagents.
Dicarboxylic esters where the carboxylic groups are separated by none or one carbon atom decompose when they are heated to give off carbon dioxide and leave behind a monocarboxylic acid.
Blanc's Rule says that heating a barium salt of a dicarboxylic ester, or dehydrating it with acetic anhydride will yield a cyclic acid anhydride if the carbon atoms bearing acid groups are in position 1 and (4 or 5).
So succinic acid will yield succinic anhydride.
For acids with carboxylic groups at position 1 and 6 this dehydration causes loss of carbon dioxide and water to form a cyclic ketone, for example, adipic acid will form cyclopentanone.
Dicarboxylic esters having an alkyl side chain and an itaconate core have been isolated from lichens and fungi, itaconic acid (methylenesuccinic acid) being a metabolite produced by filamentous fungi.
Among these compounds, several analogues, called chaetomellic acids with different chain lengths and degrees of unsaturation have been isolated from various species of the lichen Chaetomella.
These molecules were shown to be valuable as basis for the development of anticancer drugs due to their strong farnesyltransferase inhibitory effects.
Dicarboxylic esters are polar.
Because they are both hydrogen-bond acceptors (the carbonyl –C=O) and hydrogen-bond donors (the hydroxyl –OH), they also participate in hydrogen bonding.
Together, the hydroxyl and carbonyl group form the functional group carboxyl.
Dicarboxylic esters usually exist as dimers in nonpolar media due to their tendency to "self-associate".
Smaller carboxylic acids (1 to 5 carbons) are soluble in water, whereas bigger dicarboxylic esters have limited solubility due to the increasing hydrophobic nature of the alkyl chain.
These longer chain acids tend to be soluble in less-polar solvents such as ethers and alcohols.
Aqueous sodium hydroxide and dicarboxylic esters, even hydrophobic ones, react to yield water-soluble sodium salts.
Dicarboxylic esters tend to have higher boiling points than water, because of their greater surface areas and their tendency to form stabilised dimers through hydrogen bonds.
For boiling to occur, either the dimer bonds must be broken or the entire dimer arrangement must be vaporised, increasing the enthalpy of vaporization requirements significantly.
Most Dicarboxylic esters can be reduced to alcohols by hydrogenation, or using hydride transferring agents such as lithium aluminium hydride.
Strong alkyl transferring agents, such as organolithium compounds but not Grignard reagents, will reduce Dicarboxylic esters to ketones along with transfer of the alkyl group.
The most widely practiced reactions convert Dicarboxylic esters into acids, amides, carboxylate salts, acid chlorides, and alcohols.
Dicarboxylic esters react with bases to form carboxylate salts, in which the hydrogen of the hydroxyl (–OH) group is replaced with a metal cation. ,
Dicarboxylic esters often have strong sour odours.
Esters of carboxylic acids tend to have fruity, pleasant odours, and many are used in perfume.
The solubility of Dicarboxylic esters containing the carboxyl functional group in water depends on the size of the compound.
The smaller the Dicarboxylic esters (the shorter the R group), the higher the solubility.
The boiling point of aDicarboxylic esters are generally higher than that of water.
They generally have a strong sour smell.
However, their esters have pleasant odours and are therefore used in perfumes.
Dicarboxylic esters are widespread in nature, often combined with other functional groups.
Simple alkyl Dicarboxylic esters, composed of four to ten carbon atoms, are liquids or low melting solids having very unpleasant odors.
Dicarboxylic esters belong to a class of organic compounds in which a carbon (C) atom is bonded to an oxygen (O) atom by a double bond and to a hydroxyl group (−OH) by a single bond.
A fourth bond links the carbon atom to a hydrocarbon group (R).
The carboxyl (COOH) group is named after the carbonyl group (C=O) and hydroxyl group.
Esters are derived when a carboxylic acid reacts with an alcohol.
Esters containing long alkyl chains (R) are main constituents of animal and vegetable fats and oils.
Many esters containing small alkyl chains are fruity in smell, and are commonly used in fragrances.
Dicarboxylic esters are compounds which contain a -COOH group.
For the purposes of this page we shall just look at compounds where the -COOH group is attached either to a hydrogen atom or to an alkyl group.