16887-36-8

Basic information

• Product Name: 1-ADAMANTYL METHACRYLATE
• Synonyms: 1-ADAMANTYL METHACRYLATE;Adamant-1-yl methacrylate;Tricyclo[3.3.1.1~3,7~]dec-1-yl 2-methylprop-2-enoate;Tricyclo[3.3.1.1~3,7~]dec-1-yl 2-methylprop-2-enoate, 1-[(2-Methylacryloyl)oxy]adamantane;AdaMantan-1-yl Methacrylate
• CAS NO: 16887-36-8
• Molecular Formula: C₁₄H₂₀O₂
• Molecular Weight: 220.3074
• Mol File: 16887-36-8.mol

Chemical Properties

• Boiling Point: 289.26 °C at 760 mmHg
• Flash Point: 116.921 °C
• Appearance: /
• Density: 1.08 g/cm³
• Refractive Index: 1.50
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-ADAMANTYL METHACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ADAMANTYL METHACRYLATE(16887-36-8)
• EPA Substance Registry System: 1-ADAMANTYL METHACRYLATE(16887-36-8)

Safety Data

• Hazardous Substances Data: 16887-36-8(Hazardous Substances Data)

Usage

Uses

Used in Polymer Production:
1-Adamantyl methacrylate is used as a monomer in the production of polymers for its ability to be thermally polymerized or crosslinked, resulting in polymers with high resistance to radiation and heat.
Used in Coatings and Adhesives Industry:
1-Adamantyl methacrylate is used as a key component in coatings and adhesives, providing enhanced heat and radiation resistance, which is crucial for applications requiring durability and stability under extreme conditions.
Used in Electronics Industry:
1-Adamantyl methacrylate is used as a material for the fabrication of organic light-emitting diodes (OLEDs) and other device applications such as microelectronic circuits, solar cells, and displays, thanks to its thermal and radiation resistance properties.
Used in Microfabrication and Patterning:
1-Adamantyl methacrylate is used as a patterning material in electron beam lithography or ultraviolet light exposure techniques, allowing for the creation of intricate and precise patterns in various applications.
Used in Chemical Reactions:
The hydroxyl group attached to 1-adamantyl methacrylate allows it to react with aliphatic or alicyclic compounds through palladium-catalyzed reactions, expanding its utility in organic synthesis and chemical processes.

Preparation

The preparation of 1-adamantyl methacrylate is as follows:Stirrer, air inlet tube,Dean-Stark type water separator,Necked flask equipped with a stirrer, a thermometer,1-Adamantanol 100 g(0.657 mol),Methoquinone0.581 g,Hydroquinone0.143 g,Methacrylic acid227 g (2.64 mol) andMethylcyclohexaneWas added.After adding 1.61 g (0.0164 mol) of concentrated sulfuric acid,While blowing air at 10 mL / min, the mixture was stirred at a temperature of 100 to 115 ° C. for 4 hours under azeotropy of methylcyclohexane and water.4 hours laterThe conversion of 1-adamantanol was 95.1%.at this pointMethacrylic anhydride10.1 g (0.0657 mol / 2.0 equivalents to residual 1-adamantanol) was added,The mixture was further stirred for 1 hour,The reaction was terminated.The residual amount of 1-adamantanol after the reaction was 0.2%.The reaction solution was cooled to room temperature,313 g of a 20% by mass sodium hydroxide aqueous solution was added dropwise,The organic phase was washed.further,And washed twice with 100 mL of pure water.After distilling off the solvent with an evaporator, distillation under reduced pressure at 1 torr and 90 ° C.,122 g (yield 84.1%) of a colorless transparent liquid was obtained.This liquid was analyzed by GC and GPC.According to GC analysis1-Adamantyl acrylateThe purity of 99.5%.

Upstream product

• 79-41-4 poly(methacrylic acid) 
• 768-95-6 1-adamanthanol 
• 760-93-0 methacryloyl anhydride 
• 768-90-1 1-Adamantyl bromide 
• 16631-02-0 methacrylic acid silver salt 
• 285128-06-5 diadamantyl 1,1,3,3-tetramethyl-1,3-acetonedicarboxylate 
• 24569-89-9 1,3-dehydroadamantane 

Downstream Products

• 1422369-00-3 C₁₈H₁₅S⁽¹⁺⁾*C₁₆H₂₁F₂O₈S^(1-) 

Relevant articles and documents

Method of manufacturing adamantylmethacrylate

PROBLEM TO BE SOLVED: To provide a method for manufacturing adamantyl methacrylate capable of manufacturing a high-purity adamantyl methacrylate in a high yield.SOLUTION: The provided method for manufacturing adamantyl methacrylate is a method for manufacturing adamantyl methacrylate by reacting adamantanol and methacrylic acid in the presence of an acid catalyst and a polymerization inhibitor including a step of further adding, at a stage where the conversion of the adamantanol has reached a range of 90-99 mol% while the adamantanol is being converted as a result of the reaction thereof with methacrylic acid, 1.5-5.0 equivalents of methacrylic anhydride to the remaining adamantanol.

Method for synthesis of 1-adamantyl esters of unsaturated acids

New method for synthesis of adamantyl esters of acrylic, methacrylic, and cinnamic acids was developed. The reactions carried out under mild conditions in the absence of catalysts provide a high yield. Pleiades Publishing, Ltd., 2012.

Adamantyl ester monomer composition

The present invention discloses an adamantyl ester monomer composition characterized by containing at least an adamantyl ester monomer having at least one polymerizable unsaturated bond in the molecule, and a compound represented by the following general formula (1): (in the formula, R1 is an alkyl group of 1 to 5 carbon atoms, R2 is an alkyl group of 1 to 5 carbon atoms, R3 is a hydrogen atom or an alkyl group of 1 to 5 carbon atoms, and R4 is a hydrogen atom or a methyl group). The composition has high storage stability and, by subjecting it to distillation, an adamantyl ester monomer of high purity can be obtained easily.

ADAMANTYL ESTER MONOMER COMPOSITION

The present invention discloses an adamantyl ester monomer composition characterized by containing at least an adamantyl ester monomer having at least one polymerizable unsaturated bond in the molecule, and a compound represented by the following general formula (1): (in the formula, R1 is an alkyl group of 1 to 5 carbon atoms, R2 is an alkyl group of 1 to 5 carbon atoms, R3 is a hydrogen atom or an alkyl group of 1 to 5 carbon atoms, and R4 is a hydrogen atom or a methyl group). The composition has high storage stability and, by subjecting it to distillation, an adamantyl ester monomer of high purity can be obtained easily.

Engineering reactions in crystalline solids: Photochemical generation of secondary and tertiary enol radical pairs from crystalline ketodiesters

The photochemical decarbonylation of several crystalline 1,3-acetonedicarboxylates has been analyzed in solution and in the solid state. It is shown that the efficiency of the solid-state reaction depends on the stability of the intermediate acyl-alkyl an

Engineering reactions in crystalline solids: Radical pairs in crystals of dialkyl 1,3-acetonedicarboxylates

(Equation presented) Crystalline dialkyl 1,3-acetonedicarboxylates give dialkyl succinates in high chemical yields by combination of α-carbonyl radical pairs produced by photochemical decarbonylation. It is proposed that the solid-state reaction depends on the exothermicity of two consecutive bond cleavage processes. It is also suggested that the efficiency of radical formation in the solid state is determined by the effect of substituents on bond dissociation energies and radical-stabilization abilities.

Synthesis of Thermally Stable Vinyl Polymers from Adamantyl-Containing Acrylic Derivatives

1-Adamantyl and 3,5-dimethyl-1-adamantyl acrylates, methacrylates, and crotonates were polymerized through radical or anionic mechanism.Thermally stable and less-flexible vinyl polymers were obtained, depending on the structure of the repeating monomer units.