2424-01-3

Usage

Uses

Used in Chemical Synthesis:
Methyldiallylamine is used as a key intermediate in the synthesis of various quaternary ammonium compounds, which have a wide range of applications in different industries. These include diallyldimethylammonium iodide, diallylethylmethylammonium bromide, diallylbenzylmethylammonium chloride, and alkyl-substituted diallylmethyl quaternary ammonium salt monomers.
Used in Pharmaceutical Industry:
Methyldiallylamine is used as a building block for the synthesis of pharmaceutical compounds, particularly those with antimicrobial, antifungal, and antiviral properties. The quaternary ammonium compounds derived from methyldiallylamine are known for their biocidal activities and are often used in the formulation of disinfectants and sanitizers.
Used in Agrochemical Industry:
In the agrochemical industry, methyldiallylamine is utilized in the production of biocidal agents for crop protection. The quaternary ammonium compounds synthesized from methyldiallylamine exhibit pesticidal properties, helping to control pests and diseases in agricultural crops.
Used in Cosmetics and Personal Care Industry:
Methyldiallylamine and its derivatives are also used in the cosmetics and personal care industry, where they serve as preservatives and antimicrobial agents. These compounds help maintain the shelf life and safety of cosmetic and personal care products by preventing the growth of harmful microorganisms.
Used in Water Treatment Industry:
In the water treatment industry, methyldiallylamine-derived quaternary ammonium compounds are employed as coagulants and flocculants. They help in the removal of suspended solids and impurities from water, making it suitable for various applications, including drinking, irrigation, and industrial use.
Used in Textile Industry:
Methyldiallylamine is used in the textile industry for the production of cationic dyes and finishing agents. These compounds enhance the colorfastness and durability of textiles, as well as provide antimicrobial properties to fabrics, making them more resistant to microbial degradation and odor formation.

InChI:InChI=1/C7H13N/c1-3-5-7(8)6-4-2/h3-4,7H,1-2,5-6,8H2

Upstream product

• 107-18-6 allyl alcohol 
• 74-89-5 methylamine 
• 107-05-1 3-chloroprop-1-ene 
• 124-38-9 carbon dioxide 
• 124-02-7 diallylamine 
• 50-00-0 formaldehyd 
• 7664-93-9 sulfuric acid 
• 74-88-4 methyl iodide 
• 2568-61-8 N-methyl-N,N-dipropargylamine 
• 106-95-6 allyl bromide 

Downstream Products

• 1344667-71-5 2-allyl-6-methylbenzoic acid 
• 83505-34-4 2-(N-Allyl-N-methylamino)cyclohex-2-enone 

Relevant academic research and scientific papers

Synthesis of high-molecular-weight polyamine by radical polymerization of N,N-diallyl-N-methylamine

The first synthesis of high-molecular-weight poly( N,N-diallyl-N-methylamine) by thermal (at 30 and 50 °C) and photoinduced (at 21 °C) radical polymerization of N,N-diallyl-N-methylamine (DAMA) in aqueous solution in the presence of an equimolar amount of trifluoroacetic acid (TFA) and by polymerization of the newly synthesized equimolar DAMA · TFA salt is reported. Data of 1H NMR spectroscopy indicate that the molecules of the monomer under chosen conditions are in the protonated form. This leads to a decrease in the contribution of the reaction of degradative chain transfer to the monomer and its transformation into effective chain transfer to the monomer. A bimolecular chain termination mechanism was established and the possibility of controlling the polymerization rate and the molecular weight of the polymer was demonstrated.

Scope of sulfur dioxide incorporation into alkyldiallylamine-maleic acid-SO2 tercyclopolymer

Alternate copolymerization of diallylamine derivatives [(CH2CH-CH2)2NR; R = Me, (CH2)3PO(OEt)2, and CH2PO(OEt)2] (I)-maleic acid (MA) and (I·HCl)-SO2 pairs have been carried out thermally using ammonium persulfate initiator as well as UV radiation at a λ of 365 nm. The reactivity ratios of ≈0 for the monomers in each pair I-MA and I·HCl-SO2 ensured their alternation in each copolymer. However, numerous attempted terpolymerizations of I-MA-SO2 failed to entice MA to participate to any meaningful extent. In contrast to reported literature, only 1-2 mol% of MA was incorporated into the polymer chain mainly consisting of poly(I-alt-SO2). Quaternary diallyldialkylammonium chloride [(CH2CH-CH2)2N+R2Cl-; R = Me, Et] (II) also, did not participate in II-MA-SO2 terpolymerizations. Poly((I, R = Me)-alt-SO2) III is a stimuli-responsive polyampholyte; its transformation under pH-induced changes to cationic, polyampholyte-anionic, and dianionic polyelectrolytes has been examined by viscosity measurements. The pKa of two carboxylic acid groups and NH+ in III has been determined to be 2.62, 5.59, and 10.1. PA III, evaluated as a potential antiscalant in reverse osmosis plants, at the concentrations of 5 and 20 ppm, imparted ≈100% efficiency for CaSO4 scale inhibition from its supersaturated solution for over 50 and 500 min, respectively, at 40 °C. The synthesis of PA III in excellent yields from cheap starting materials and its very impressive performance may grant PA III a prestigious place as an environment-friendly phosphate-free antiscalant.

Dynamic Exchange in Intramolecular Lewis Pairs with Multiple Lewis-Acidic Functions

Hydroboration of allyldimethylamine, diallylmethylamine, triallylamine, and diallylmethylphosphane with dimeric 9-BBN yielded the corresponding singly, doubly, and triply Lewis-acid-functionalized intramolecular Lewis pairs. For the singly Lewis-acid-functionalized derivative Me2N(CH2)3-9-BBN no evidence for the existence of an equilibrium involving an open-chain form was found in solution. For the doubly and triply Lewis-acid-functionalized compounds Me3-xE[(CH2)3-9-BBN]x [E = N (x = 2, 3), P (x = 2)] a dynamic exchange of the free Lewis-acid functions with an intramolecular Lewis acid base complex was observed and investigated by variable-temperature NMR spectroscopy. The free energies of activation of the exchange processes were determined by the coalescence method and found to be lower for the Lewis-base component nitrogen than for phosphorus. To further understand the exchange process of the Lewis acids at the central Lewis base, transition states for two different exchange mechanisms were considered and searched for.

Production method of N-methyldiallylamine

The invention discloses a production method of N-methyldiallylamine. The method comprises the following steps: adding monomethylamine and water into a high-pressure reaction kettle, adding a phase transfer catalyst, and dropwise adding chloropropene and an alkali liquor catalyst into the high-pressure reaction kettle to obtain a reaction solution; and layering the reaction solution, wherein the upper oil phase is a N-methyldiallylamine crude product; and pumping the crude product into a rectifying still for refinement. According to the method, the amination reaction is adopted, the reaction speed is high, the raw materials can fully react, the yield is high (99% or above), few byproducts are generated, and meanwhile, the byproduct N-methylallylamine can be repeatedly reacted; through the method, the prepared N-methyldiallylamine is colorless transparent liquid in appearance; when the chromaticity is measured by a colorimeter, the chromaticity is smaller than or equal to 17, the content detected by a GC gas chromatography is larger than or equal to 98.5%, and the moisture is smaller than or equal to 0.1%; the purity of the N-methyldiallylamine is high; and lower-layer wastewater is easy to treat, and the cost of subsequent wastewater treatment is saved.

Preparation method of N-diallylmethylamine and hydrochloride thereof

The invention belongs to the technical field of medical intermediates and particularly relates to a preparation method of N-diallylmethylamine and hydrochloride thereof. The preparation method comprises the following steps: adding monomethylamine and water into an autoclave, adding a catalyst and stirring; then dropwise adding 3-chloropropene into a reaction still, adding sodium hydroxide after dropwise adding is finished, raising the temperature to 50 to 60 DEG C, pressurizing to 0.25 to 0.3 MPa and cooling to below 40 DEG C, thus obtaining reaction liquid; layering the reaction liquid, and obtaining an oil phrase, namely a crude product of N-diallylmethylamine; pumping the crude product into a rectifying still for purifying; firstly, collecting former components; then collecting qualified N-diallylmethylamine, and feeding the former components into the reaction still for reuse. The preparation method for preparing the N-diallylmethylamine and hydrochloride thereof, has the advantagesof easily-purchased raw materials, low production cost and simple process; in addition, the product has the advantages of high output, stable quality and 99 percent or above of the yield.

1,4-Dioxane-Tuned Catalyst-Free Methylation of Amines by CO2 and NaBH4

A catalyst-free reductive functionalization of CO2 with amines and NaBH4 was developed. The N-methylation of amines was carried out with CO2 as a C1 building block and 1,4-dioxane as the solvent. Notably, the six-electron reduction of CO2 to form the methyl group occurred simultaneously with formation of the C?N bond to give the N-methylated amine.

Poly (diallylamines)-based phosphate binders

The present invention relates to a method for lowering the serum phosphate level of a patient. The method comprises the step of administering to the patient a therapeutically effective amount of a polymer characterized by a diallylamine monomer or repeat unit. The amino nitrogen atom of the diallylamine repeat unit can be substituted by one or two substituents independently selected from among substituted and unsubstituted, normal, branched and cyclic alkyl groups, and aryl groups. When the diallylamine repeat unit comprises an ammonium or quaternary ammonium group, the monomer will further comprise a suitable anion, such as a conjugate base of a pharmaceutically acceptable acid.

Process for the synthesis of N-methyl-dialkylamines from secundary amines and formaldehyde

Production of N-methyldialkylamines comprises reacting a dialkylamine with 1.5-3 molar equivalents of formaldehyde at 100-200[deg]C; degassing the reaction product; separating the aqueous phase; and distilling the organic phase.

Poly(diallylamine)-based bile acid sequestrants

The present invention relates to a method for removing bile acids from a patient and certain polymers of use in the method. The method comprises the step of administering to the patient a therapeutically effective amount of a polymer composition which includes a a poly(diallylamine) polymer which is substituted with hydrophobic groups. The hydrophobic groups can be a substituted or unsubstituted, straight chain or branched C3-C24-alkyl group, an aralkyl group or an aryl group.

Tuning the properties of conjugated polyelectrolytes and application in a biosensor platform

The present invention provides a method of detecting a biological agent including contacting a sample with a sensor including a polymer system capable of having an alterable measurable property from the group of luminescence, anisotropy, redox potential and uv/vis absorption, the polymer system including an ionic conjugated polymer and an electronically inert polyelectrolyte having a biological agent recognition element bound thereto, the electronically inert polyelectrolyte adapted for undergoing a conformational structural change upon exposure to a biological agent having affinity for binding to the recognition element bound to the electronically inert polyelectrolyte, and, detecting the detectable change in the alterable measurable property. A chemical moiety being the reaction product of (i) a polyelectrolyte monomer and (ii) a biological agent recognition element-substituted polyelectrolyte monomer is also provided.