2424-61-5

Usage

Uses

Used in Rubber Industry:
Dodecyl hydrogen maleate is used as an additive for improving the mechanical properties of vulcanizates of natural rubber bands. Its addition to the rubber formulation leads to enhanced strength, elasticity, and durability of the final product, making it more resistant to wear and tear.

InChI:InChI=1/C16H28O4/c1-2-3-4-5-6-7-8-9-10-11-14-20-16(19)13-12-15(17)18/h12-13H,2-11,14H2,1H3,(H,17,18)/b13-12-

Upstream product

• 108-31-6 maleic anhydride 
• 112-53-8 1-dodecyl alcohol 

Relevant academic research and scientific papers

Epoxidation of monomaleate with hydrogen peroxide catalyzed by [π-C 5H5N(CH2)15CH3] 3PO4(WO3)4

In the study, epoxidation of dodecanol monomaleate, hexadecanol monomaleate, and octadecanol monomaleate were carried out using [π-C 5H5N(CH2)15CH3] 3PO4(WO3)4 as phase-transfer catalyst with 30% hydrogen peroxide as oxidant. The experimental results showed that [π-C5H5N(CH2)15CH 3]3PO4(WO3)4 had excellent catalytic effect on translating C=C double-bond into an epoxy group and had a good yield rate. The synthesized epoxides of decanol monomaleate, hexadecanol monomaleate, and octadecanol monomaleate have enormous potential application in organic synthesis, and they could be readily transformed into various synthetically useful intermediates or final products in many fields of chemistry.

Interfacial properties of novel surfactants based on maleic and succinic acid for potential application in personal care

Hemiesters and Hemiamides of maleic and succinic acid viz. sodium lauryl succinate (C12SE), sodium lauryl maleate (C12ME), sodium lauryl succinamide (C12SA), sodium lauryl maleamide (C12MA), sodium hexadecyl succinate (C16SE) and sodium hexadecyl maleate (C16ME) were synthesized and investigated as surfactants in the pure water and aqueous hydrotrope [sodium p-toluene sulfonate (NaPTs)] solution. The chemical structures of the prepared surfactants were established by FTIR and 1H NMR spectroscopy. The surface tension measurements depicted low CMC and a high adsorption efficiency (pC20) which is highly beneficial for creating personal care formulations. The dynamic light scattering (DLS) technique indicated the formation of larger micelles which was important for skin care as larger micelles cannot penetrate the skin layer. Moreover, these surfactants depicted good foamability and stability attributed to faster monomer adsorption and small bubble size which was preferred for cleansing application. Additionally, low protein/lipid solubilization by these surfactants indicated its mild behaviour on skin as compared to other commonly used conventional anionic [sodium lauryl sulfate (SLS)], zwitterionic [cocamidopropyl betaine (CAPB)] and nonionic [decyl glucoside (DG)] surfactants. Viscosity measurements suggested decent thickening ability of surfactants in the presence of co-surfactant like lauramine oxide. Basis of all the properties discussed, these novel hemiesters and hemiamides seem promising as surfactants for improving various characteristics in potential personal care formulations.

DRUGS AND COMPOSITIONS FOR OCULAR DELIVERY

New prodrugs of therapeutically active compounds, including oligomeric prodrugs of ethacrynic acid, and compositions to treat medical disorders, for example glaucoma, a disorder or abnormality related to an increase in intraocular pressure (IOP), a disorder requiring neuroprotection, age-related macular degeneration, or diabetic retinopathy. Also a method for the controlled administration of timolol to a patient in need thereof, such as a human, comprising administering a prodrug of timolol in a microparticle in vivo, wherein the timolol prodrug containing microparticle exhibits in vitro drug release kinetics in an aqueous solution at a pH between 6-8 at body temperature of a substantially consistent release of at least 60% timolol itself by molar ratio to the prodrug of timolol or an intermediate metabolite thereof over at least 100 days.

Asymmetric sodium benzenesulfonate Gemini surfactant: Synthesis, properties and application

An asymmetric sodium benzenesulfonate Gemini surfactant (ASBGS) designed and prepared by esterification and sulfonation reaction using 4- (dodecyl amide) phenol (4-DAP), dodecanol maleic acid monoester (DMM) and NaHSO3. The structure of the ASBGS characterized by FT-IR and 1H NMR. The surface tension, emulsifying force and aggregation property of the ASBGS tested. The results showed that the critical micelle concentration and γCMC of ASBGS were 0.8 × 10?4 mol/L and 25.1 mN/m, respectively. Thermodynamic parameters results showed that the micellization of this surfactant was a spontaneous process. DLS and TEM results showed that the concentration of 10 CMC surfactant solution aggregated into vesicles, and the average particle size was 85 nm. Then ASBGS was used to emulsify rapeseed oil for lubricating collagen fiber. The emulsification time for rapeseed oil was 283 s, showing that ASBGS has an excellent emulsifying ability. In addition, we prepared collagen fiber lubricating materials (CFLMs) by blending different dosages of the ASBGS with rapeseed oil collagen fiber lubricating material (ROCLM), its emulsifying ability increased from 47.37% to 87.37% in cold water.

DRUGS AND COMPOSITIONS FOR THE TREATMENT OF OCULAR DISORDERS

The present invention provides new prodrugs of therapeutically active compounds, including oligomeric prodrugs, and compositions to treat medical disorders, for example glaucoma, a disorder or abnormality related to an increase in intraocular pressure (IOP), a disorder requiring neuroprotection, age-related macular degeneration, or diabetic retinopathy.

A comparative study of the thermal properties of homologous series of crystallisable n-alkyl maleate and itaconate monoesters

Homologous series of crystallisable C8-C22 even-numbered alkane oligomers with either maleate or itaconate monoesters end-groups were synthesized. Their total phase change enthalpy (ΔHtpce) and entropy (ΔStpce) on melting, determined by DSC, show a linear dependence with the number of carbons of the alkyl chain. A comparison was performed with corresponding succinate derivatives. The influence of the end functions on ΔStpce was examined in view of ΔStpce values estimated by the group additivity approach. A fair agreement between the experimental and the estimated entropy values could be demonstrated. Thermogravimetric analysis (TGA) has shown that the maleate oligomers are less stable than the corresponding succinate and itaconate derivatives. This behaviour could be confirmed by the activation energies of the degradation process.

Isobutylene-rich macromonomers: Dynamics and yields of peroxide-initiated crosslinking

New isobutylene-rich elastomers bearing multiple pendant styrenic, acrylic, maleimidic, vinylic, and allylic functional groups have been prepared and examined in the context of peroxide-initiated crosslinking. Halide displacement from brominated poly(isobutylene-co-isoprene) (BIIR) by the requisite carboxylate nucleophiles in homogeneous toluene solutions provide the desired esters in quantitative yield without complications from dehydrohalogenation or premature crosslinking. Heating the resulting macromonomers with dicumyl peroxide to 160 °C under solvent-free conditions gives thermoset derivatives, with reaction rates and yields depending markedly on functional group structure. In general, high cure extents can only be achieved using highly reactive pendant functional groups, owing to the competitive balance between crosslinking through C=C oligomerization, and degradation through β-scission of backbone macroradical intermediates. Independent control of crosslinking rates and cure extents is gained through the use of nitroxyl radical traps bearing acrylate functionality.

Dicarboxylic acid esters as transdermal permeation enhancers: Effects of chain number and geometric isomers

A series of transdermal permeation enhancers based on dicarboxylic acid esters was studied. Single-chain amphiphiles were markedly more effective than the double-chain ones. Monododecyl maleate, that is a cis derivative, was a more potent enhancer than its trans isomer, while the activity of succinates strongly depended on the donor vehicle. No difference between diastereoisomeric tartaric and meso-tartaric acid derivatives was found.

Synthetic ceramide analogues as skin permeation enhancers: Structure-Activity relationships

The study presents new information about the structure-activity relationships of the skin permeation enhancers. A series of ceramide analogues including eight different polar head groups and six different chain lengths was synthesised. The compounds were evaluated as permeation enhancers in vitro using porcine skin. The physico-chemical parameters of the tested compounds obtained by computer modelling were used to evaluate, by multiple linear regression, the enhancement ratios (ERs) of the compounds. The regression analysis suggests that the hydrogen bonding ability of the compounds is inversely related to the ER values and that the molecular size and lipophilicity must be well balanced. In the studied enhancers having the same chain length, the enhancement activity is dependent only on their permeability coefficients. This finding confirms the Warner's hypothesis that the polar head of an enhancer is responsible for the permeation and anchoring of the molecule into the stratum corneum lipids and that it does not influence the mechanism of action. For the specific action of enhancers, that is disordering of the intercellular lipid packing, the length of the hydrophobic chain(s) and not the lipophilicity is important. Furthermore, the examination of the FTIR spectra indicated that the most active substances possess the most ordered chains. The described relationships could bring more rational approaches in designing new potent enhancers for transdermal formulations.

Process for producing an unsymmetrical diester of α, β-unsaturated dicarboxylic acid

A process for producing a colorless unsymmetrical-diester of maleic acid, useful as a raw material of an emulsifier for emulsion polymerization and as a modifier for a polymer, which comprises: (1) reacting maleic anhydride with a monohydric alcohol in the presence of an inert organic solvent, in a molar ratio of 1:(1.0-1.2) to obtain maleic acid mono ester containing substantially no unreacted maleic anhydride, and (2) reacting said monoester with an alkenyl halide in the presence of a tertiary amine and water, in a molar ratio of said monoester:water of 1:(0.01-0.20).