142-90-5

Basic information

• Product Name: Dodecyl 2-methylacrylate
• Synonyms: DODECYL METHACRYLATE;DODECYL 2-METHYL-2-PROPENOATE;DODECYL 2-METHYLPROPENOATE;LAURYL METHACRYLATE;METHACRYLIC ACID DODECYL ESTER;METHACRYLIC ACID N-DODECYL ESTER;METHACRYLIC ACID LAURYL ESTER;2-METHYL-2-PROPENOIC ACID DODECYL ESTER
• CAS NO: 142-90-5
• Molecular Formula: C₁₆H₃₀O₂
• Molecular Weight: 254.41
• EINECS: 205-570-6
• Product Categories: Functional Monomer;Pyridines
• Mol File: 142-90-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: −7 °C(lit.)
• Boiling Point: 142 °C4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear light yellow/Liquid
• Density: 0.873 g/mL at 20 °C
• Vapor Pressure: 0.000274mmHg at 25°C
• Refractive Index: n20/D 1.445(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: insoluble
• BRN: 1708160
• CAS DataBase Reference: Dodecyl 2-methylacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Dodecyl 2-methylacrylate(142-90-5)
• EPA Substance Registry System: Dodecyl 2-methylacrylate(142-90-5)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 26-28-60-61-28B
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 2
• RTECS: OZ4300000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 142-90-5(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellowish liquid

Uses

Miniemulsion polymerization of laurel methacrylate has been reported. Atom transfer radical polymerization and consecutive block copolymerization with methyl methacrylate has been investigated. Preparation of LMA based monolithic columns for CEC has been reported. LMA is used as a co-stabilizer to retard Ostwald ripening effect.

General Description

Liquid. Floats on water.

Reactivity Profile

Dodecyl 2-methylacrylate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Tends to polymerize. Oxidizing and reducing agents may initiate polymerization. Reaction may also occur when heated [USCG, 1999].

Health Hazard

Inhalation temporarily reduces blood pressure from 5 to 25%, increases respiratory rate, decreases heart rate, and causes some EKG changes. Liquid may cause irritation of eyes and skin. May be harmful if swallowed.

Fire Hazard

Behavior in Fire: Heat can induce polymerization with rapid release of energy. Sealed containers may rupture explosively.

Flammability and Explosibility

Nonflammable

Purification Methods

Purify the ester by fractional distillation in a high vacuum. Add 0.05% of hydroquinone monomethyl ether as stabilizer. [Rehberg & Fischer Ind Eng Chem 40 1430 1948, Beilstein 2 III 1290, 2 IV 1528.]

InChI:InChI=1/C16H30O2/c1-4-5-6-7-8-9-10-11-12-13-14-18-16(17)15(2)3/h2,4-14H2,1,3H3

Synthetic route

poly(methacrylic acid) (79-41-4) + 1-dodecyl alcohol (112-53-8) → n-dodecyl methacrylate (142-90-5)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;	86%
With phosphoric acid; (p-tolueneslfonic acid, sulfosalicylic acid, resin KU-2x8); hydroquinone In toluene Heating;

1-dodecyl alcohol (112-53-8) + 3-(2-methylpropenoyl)-oxazolidin-2-one (31978-13-9) → n-dodecyl methacrylate (142-90-5)

Conditions	Yield
With ytterbium(III) triflate In acetonitrile at 90℃; for 48h; Sealed tube; Inert atmosphere;	79%

1-dodecyl alcohol (112-53-8) + methacrylic acid methyl ester (80-62-6) → n-dodecyl methacrylate (142-90-5)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; dibutyltin dilaurate; zirconium(IV) acetylacetonate Reagent/catalyst; Autoclave; Reflux; Large scale;	70.99%
at 60 - 70℃;
Stage #1: 1-dodecyl alcohol; methacrylic acid methyl ester With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy for 1h; Heating / reflux; Stage #2: titanium tetramethoxide at 111 - 129℃; for 3 - 6.5h; Product distribution / selectivity;	96 - 98.5 %Chromat.
With sulfuric acid at 110 - 150℃;

α-hydroxy-isobutyric acid dodecyl ester → n-dodecyl methacrylate (142-90-5)

Conditions	Yield
With phosphorus pentoxide; 1,2-dichloro-ethane

n-dodecyl methacrylate (142-90-5) → dodecyl isobutyrate (6624-71-1)

Conditions	Yield
With Dimethylphenylsilane; copper(l) chloride In various solvent(s) for 6h; Ambient temperature;	95%
With hydrogen In water; toluene for 3h; pH=3 - 7;	>= 99 %Chromat.

n-dodecyl methacrylate (142-90-5) → dodecyl methacrylate-d5

Conditions	Yield
With platinum on carbon; water-d2; hydroquinone; isopropyl alcohol at 120℃; for 24h; Sealed tube;	69%

n-dodecyl methacrylate (142-90-5) + dansyl iodide (622837-75-6) → lauryl 2-(dansylmethyl)acrylate

Conditions	Yield
Stage #1: n-dodecyl methacrylate; dansyl iodide In tetrachloromethane at 20℃; for 24h; Stage #2: With triethylamine In tetrachloromethane for 24h; Heating;	60%

n-dodecyl methacrylate (142-90-5) → Sodium; 2-dodecyloxycarbonyl-propane-1-sulfonate (85557-24-0)

Conditions	Yield
With sodium hydrogensulfite In ethanol at 80 - 100℃; under 1520 - 2280 Torr; Yield given;

4-vinylpyridine (100-43-6) + n-dodecyl methacrylate (142-90-5) + EDMA (97-90-5) → polymer; monomer(s): dodecyl methacrylate; 4-vinylpyridine; ethylene dimethacrylate

Conditions	Yield
at 20℃; for 72h; Irradiation;

n-dodecyl methacrylate (142-90-5) + poly(methacrylic acid) (79-41-4) + EDMA (97-90-5) → polymer; monomer(s): dodecyl methacrylate; methacrylic acid; ethylene dimethacrylate

Conditions	Yield
at 20℃; for 72h; Irradiation;

n-dodecyl methacrylate (142-90-5) + EDMA (97-90-5) + 2-Methacryloyloxyethyl-1-sulfonic acid (10595-80-9) + methacrylic acid methyl ester (80-62-6) → polymer; monomer(s): dodecyl methacrylate; methyl methacrylate; sulfoethyl methacrylate; ethylene dimethacrylate

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 72h; Irradiation;

styrene (292638-84-7) + n-dodecyl methacrylate (142-90-5) → polymer; Monomer(s): styrene; n-dodecyl methacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 60℃; Product distribution; Further Variations:; concentrarions;
With 2,2'-azobis(isobutyronitrile) In toluene at 60℃;

n-dodecyl methacrylate (142-90-5) + N-Isopropylacrylamide (2210-25-5) + sodium dodecyl-sulfate (151-21-3) → cross-linked poly[N-isopropylacrylamide]-co-[dodecyl methacrylate]/sodium dodecyl sulfate complex; MW: 226,000 g/mol

Conditions	Yield
With N,N'-Methylenebisacrylamide; 2,2-diethoxyacetophenone; 2-propenamide In water; triethylamine at 35℃; for 4h; UV-irradiation;

n-dodecyl methacrylate (142-90-5) + acrylic acid methyl ester (292638-85-8) → polymer: monomer(s): dodecyl methacrylate; methyl acrylate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone at 40℃; under 750060 Torr; Kinetics; Irradiation;

n-dodecyl methacrylate (142-90-5) + N-Isopropylacrylamide (2210-25-5) + trimethoxy(7-octen-1-yl)silane (52217-57-9) → polymer; Monomer(s): N-isopropylacrylamide; dodecyl methacrylate

Conditions	Yield
at 120℃;

n-dodecyl methacrylate (142-90-5) + poly(oligo-oxyethylene methacrylate), MW: 100 g/mol, polydispersity 1.3 → poly(oligo-oxyethylene methacrylate)-block-poly(lauryl methacrylate), composition 53:47 (v/v), MW: 65 g/mol, polydispersity 1.1, anionic polymerization

Conditions	Yield
With (diphenylmethyl)potassium In tetrahydrofuran

n-dodecyl methacrylate (142-90-5) + EDMA (97-90-5) → ethylene glycol dimethacrylate dodecyl methacrylate copolymer, radical polymerisation, Mn: 1450, Mw: 2900, Mw/Mn: 2.0; monomer(s): ethylene glycol dimethacrylate; dodecyl methacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); Co(II) tetramethylhematoporphyrin-IX In N,N-dimethyl-formamide at 60℃;

n-dodecyl methacrylate (142-90-5) → poly(dodecyl methacrylate); monomer(s): dodecyl methacrylate

Conditions	Yield
With 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one at 40℃; under 750060 Torr; Kinetics; Irradiation;

hydroxylated polybutadiene-based polyurethane; R-45HT, Atofina + n-dodecyl methacrylate (142-90-5) → Polymer, graft; Monomer(s): telechelic polybutadiene, dodecyl methacylate

Conditions	Yield
With potassium peroxomonosulphate; sodium dodecyl-sulfate; sodium hydrogencarbonate In water at 50℃;

n-dodecyl methacrylate (142-90-5) → poly(lauryl methacrylate), syndiotacticity/atacticity/isotacticity 65 percent/31 percent/14 percent by 13C NMR; monomer(s): lauryl methacrylate

Conditions	Yield
With (2-hydroxycyclohexyl)(phenyl)methanone at 25℃; UV-irradiation;

styrene (292638-84-7) + n-dodecyl methacrylate (142-90-5) + poly(methacrylic acid) (79-41-4) + 2,3-Epoxypropyl methacrylate (106-91-2) → Polymer, Mw=7210 (GPC), Tg=63.38 deg C, radical solution copolymerization of methacrylic acid, glycidyl methacrylate, styrene and lauryl methacrylate, with a total content of 15:20:45:20 wt/wt percent, respectively

Conditions	Yield
With 2,2'-azobis-(2,4-dimethylvaleronitrile) In various solvent(s) at 70℃; for 8h;

11-dimethylaminodecyl methacrylate + n-dodecyl methacrylate (142-90-5) → Reaxys ID: 15742651

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide

n-dodecyl methacrylate (142-90-5) + 2-methacryloyloxyethyl phosphorylcholine (67881-98-5) → polymer, obtained by copolymerization initiated with AIBN; monomer(s): 2-methacryloyloxyethylphosphorylcholine, 33 mol%; lauryl methacrylate, 67 mol%

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 62℃;

n-dodecyl methacrylate (142-90-5) + 2-hydroxypropyl methacrylate (923-26-2) + [3-(methacryloyloxy)propyl]trimethoxysilane (2530-85-0) + 2-methacryloyloxyethyl phosphorylcholine (67881-98-5) → polymer, obtained by copolymerization initiated with AIBN; monomer(s): 2-methacryloyloxyethylphosphorylcholine, 23 mol%; lauryl methacrylate, 47 mol%; 2-hydroxypropyl methacrylate, 25 mol%; trimethoxysilylpropyl methacrylate, 5 mol%

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 62℃;

n-dodecyl methacrylate (142-90-5) + 2-hydroxypropyl methacrylate (923-26-2) + [3-(methacryloyloxy)propyl]trimethoxysilane (2530-85-0) + 2-methacryloyloxyethyl phosphorylcholine (67881-98-5) → polymer, obtained by copolymerization initiated with AIBN; monomer(s): 2-methacryloyloxyethylphosphorylcholine, 47 mol%; lauryl methacrylate, 23 mol%; 2-hydroxypropyl methacrylate, 25 mol%; trimethoxysilylpropyl methacrylate, 5 mol%

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 62℃;

n-dodecyl methacrylate (142-90-5) + 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → polymer, radical polymerization, degree of polymerization 160; monomer(s): 2,2-dimethoxy-2-phenyl-acetophenone; dodecyl methacrylate + polymer, radical polymerization, degree of polymerization 5190; monomer(s): 2,2-dimethoxy-2-phenyl-acetophenone; dodecyl methacrylate

Conditions	Yield
Stage #1: n-dodecyl methacrylate; 2,2-dimethoxy-2-phenylacetophenone at 25℃; UV-irradiation; Stage #2: n-dodecyl methacrylate at 25℃; Further stages. Title compound not separated from byproducts.;

n-dodecyl methacrylate (142-90-5) + 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → polymer, radical polymerization, degree of polymerization 190; monomer(s): 2,2-dimethoxy-2-phenyl-acetophenone; dodecyl methacrylate + polymer, radical polymerization, degree of polymerization 7550; monomer(s): 2,2-dimethoxy-2-phenyl-acetophenone; dodecyl methacrylate

Conditions	Yield
Stage #1: n-dodecyl methacrylate; 2,2-dimethoxy-2-phenylacetophenone at 25℃; UV-irradiation; Stage #2: n-dodecyl methacrylate at 25℃; Further stages. Title compound not separated from byproducts.;

n-dodecyl methacrylate (142-90-5) + 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → polymer, radical polymerization, degree of polymerization 150; monomer(s): 2,2-dimethoxy-2-phenyl-acetophenone; dodecyl methacrylate + polymer, radical polymerization, degree of polymerization 2950; monomer(s): 2,2-dimethoxy-2-phenyl-acetophenone; dodecyl methacrylate

Conditions	Yield
Stage #1: n-dodecyl methacrylate; 2,2-dimethoxy-2-phenylacetophenone at 25℃; UV-irradiation; Stage #2: n-dodecyl methacrylate at 25℃; Further stages. Title compound not separated from byproducts.;

Upstream product

• 112-53-8 1-dodecyl alcohol 
• 760-93-0 methacryloyl anhydride 
• 31978-13-9 3-(2-methylpropenoyl)-oxazolidin-2-one 
• 79-41-4 poly(methacrylic acid) 
• 80-62-6 methacrylic acid methyl ester 

Downstream Products

• 6624-71-1 dodecyl isobutyrate 

Relevant articles and documents

Novel bioactive imidazole-containing polymeric surfactants as petroleum-collecting and dispersing agents: Synthesis and surface-active properties

Novel series of imidazole-containing polymers and polymeric surfactants have been synthesized via an efficient procedure. It included copolymerization of 1-vinyl-imidazole (VIM) with lauryl methacrylate (LMA) initiated by benzoyl peroxide and the 1H NMR spectroscopic data was utilized to estimate the monomer reactivity ratio. Conversion of polymers to surfactants was achieved through quaternization of the imidazole nitrogen with dimethyl sulphate. Spectroscopic techniques were used to elucidate the chemical structures of all synthesized compounds. The surface-active properties of polymeric surfactants beside their activities against various microbes were investigated. In addition, petroleum-collecting and dispersing properties of surfactants in diluted and undiluted form in varying waters were evaluated.

Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides

An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.

Process for producing methacrylic ester

A method of producing a methacrylic acid ester which comprises carrying out an ester-exchange reaction between methyl methacrylate and an alcohol or a phenol while removing by-product methanol as an azeotropic mixture with methyl methacrylate from the reaction system under reflux conditions, by the use of a reaction apparatus equipped with a distillation column. A methacrylic acid ester is produced with a good productivity by controlling the reflux ratio.