4813-57-4

Basic information

• Product Name: Octadecyl acrylate
• Synonyms: 2-Propenoicacid,octadecylester;Octadecyl2-propenoate;octadecylacrylate(stearylacrylate);STEARYL ACRYLATE;N-OCTADECYL ACRYLATE;OCTADECYL ACRYLATE;Octadecylacrylat;Stearyl Acrylate (stabilized with MEHQ)
• CAS NO: 4813-57-4
• Molecular Formula: C₂₁H₄₀O₂
• Molecular Weight: 324.54
• EINECS: 225-383-3
• Product Categories: Functional Monomer
• Mol File: 4813-57-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 32-34 °C(lit.)
• Boiling Point: 402.85°C (rough estimate)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.8 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.29E-06mmHg at 25°C
• Refractive Index: 1.5344 (estimate)
• Solubility: Insoluble in water
• Water Solubility: 260.9ng/L at 25℃
• CAS DataBase Reference: Octadecyl acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Octadecyl acrylate(4813-57-4)
• EPA Substance Registry System: Octadecyl acrylate(4813-57-4)

Safety Data

• Hazard Codes: Xi,N
• Statements: 41-51/53-36/37/38-43-38
• Safety Statements: 26-39-61-36/37/39
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 2
• Hazardous Substances Data: 4813-57-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 4813-57-4 differently. You can refer to the following data:
1. stearyl acrylate is generally found in combination with other chemicals, it acts as a film former to help maintain moisture in the skin.
2. Octadecyl Acrylate is a reagent used in the synthesis of comb-like polymers which are incorporated into waterborne latexes improving barrier properties.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C21H40O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23-21(22)4-2/h4H,2-3,5-20H2,1H3

Synthetic route

1-octadecanol (112-92-5) + acrylic acid (79-10-7) → octadecylacrylate (4813-57-4)

Conditions	Yield
With 10H-phenothiazine; hydroquinone at 110 - 130℃; for 4.5h; Temperature;	95.7%
With 10H-phenothiazine at 254℃; under 20252 Torr; for 0.0119444h; Microwave Irradiation; Autoclave; Industry scale;	93%
With hydroquinone In cyclohexane at 60 - 140℃; for 6h;

1-octadecanol (112-92-5) + acryloyl chloride (814-68-6) → octadecylacrylate (4813-57-4)

Conditions	Yield
With dmap In dichloromethane Reflux;	95%

1-octadecanol (112-92-5) + acrylic acid methyl ester (292638-85-8) → octadecylacrylate (4813-57-4)

Conditions	Yield
With acid

1-octadecanol (112-92-5) + acetylene (74-86-2) → octadecylacrylate (4813-57-4)

Conditions	Yield
With hydrogenchloride; tetracarbonyl nickel; benzene

1-octadecanol (112-92-5) + acetylene (74-86-2) + carbon monoxide → octadecylacrylate (4813-57-4)

Conditions	Yield
With hydrogenchloride; tetracarbonyl nickel; acetone

octadecylacrylate (4813-57-4) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → C28H57NO7

Conditions	Yield
In 1,4-dioxane; water at 50℃; for 5h;	98%

methanol (67-56-1) + octadecylacrylate (4813-57-4) + carbon monoxide (201230-82-2) → 1,2-dimethyl 1-octadecyl ethane-1,1,2-tricarboxylate

Conditions	Yield
With palladium(II) trifluoroacetate; N,N'-bis(2,6-dimethylphenyl)butane-2,3-diimine; toluene-4-sulfonic acid; p-benzoquinone In tetrahydrofuran at 20℃; under 3000.3 Torr; for 67h; Autoclave;	92%

octadecylacrylate (4813-57-4) + rac-Pro-OH (609-36-9) → C26H49NO4

Conditions	Yield
In ethanol at 75℃; for 15h; Michael Addition;	89.7%

octadecylacrylate (4813-57-4) + tris-(trimethylsilyl)silane (1873-77-4) → octadecyl 3-[tris(trimethylsilyl)silyl]propionate

Conditions	Yield
at 25 - 40℃; for 72h;	87%

3-phenylcumarin (955-10-2) + octadecylacrylate (4813-57-4) → octadecyl (E)-3-(2-(2-oxo-2H-chromen-3-yl)phenyl)acrylate

Conditions	Yield
With dipotassium peroxodisulfate; palladium diacetate In trifluoroacetic acid; trifluoroacetic anhydride at 90℃; for 3h; regioselective reaction;	75%

octadecylacrylate (4813-57-4) + 8-mesityl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (870753-29-0) → 4,4-difluoro-8-(2,4,6-trimethylphenyl)-2,6-bis[(E)-3-octadecyloxy-3-oxoprop-1-en-1-yl]-4-bora-3a,4a-diaza-s-indacene

Conditions	Yield
With silver(I) acetate; palladium diacetate at 80℃; for 10h; regioselective reaction;	70%

2,3,6-tribromo-1-methyl-1H-indole (70063-24-0) + octadecylacrylate (4813-57-4) → (2E,2'E,2''E)-trioctadecyl 3,3',3''-(1-methyl-1H-indole-2,3,6-triyl)triacrylate (1314798-90-7)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 90℃; for 36h; Heck reaction; Inert atmosphere;	64%

2,5-dimethyl-pyrazine 1-oxide (6890-37-5) + octadecylacrylate (4813-57-4) → C27H46N2O3

Conditions	Yield
With potassium acetate; palladium diacetate; silver carbonate; Trimethylacetic acid In 1,4-dioxane at 100℃; for 24h; Sealed tube; regioselective reaction;	62%

octadecylacrylate (4813-57-4) + benzaldehyde (100-52-7) → 3-(hydroxy(phenyl)methyl)-5-phenyldihydrofuran-2(3H)-one

Conditions	Yield
With samarium; copper(l) iodide; potassium iodide In tetrahydrofuran at 20℃; Molecular sieve; diastereoselective reaction;	61%

Quinoline N-oxide (1613-37-2) + octadecylacrylate (4813-57-4) → (E)-octadecyl 3-(quinolin-2-yl)acrylate

Conditions	Yield
With acetic acid In dimethyl sulfoxide at 120℃; for 40h; Sealed tube; regioselective reaction;	53%

octadecylacrylate (4813-57-4) + 8-mesityl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (870753-29-0) → 4,4-difluoro-8-(2,4,6-trimethylphenyl)-2-[(E)-3-octadecyloxy-3-oxoprop-1-en-1-yl]-4-bora-3a,4a-diaza-s-indacene

Conditions	Yield
With palladium diacetate; silver trifluoroacetate at 80℃; for 24h; regioselective reaction;	50%

octadecylacrylate (4813-57-4) + 1-phenyl-1-pentyne (4250-81-1) → octadecyl 2-phenyl-3-propylcyclobut-2-ene-1-carboxylate

Conditions	Yield
With indium tris(trifluoroacetylacetonate); trimethylsilyl bromide In 1,2-dichloro-ethane at 0 - 20℃; for 2h; Inert atmosphere;	13%

poly(methacrylic acid) (79-41-4) + N-Isopropylacrylamide (2210-25-5) + octadecylacrylate (4813-57-4) → poly(NIPA93-co-MAA5-co-ODA2)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In 1,4-dioxane at 65℃; for 5h; Polymerization;

poly(methacrylic acid) (79-41-4) + N-Isopropylacrylamide (2210-25-5) + octadecylacrylate (4813-57-4) → poly(NIPA91-co-MAA5-co-ODA4)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In 1,4-dioxane at 65℃; for 5h; Polymerization;

tert-Butyl acrylate (1663-39-4) + octadecylacrylate (4813-57-4) → polymer, Mn 13680 by SEC, Mw/Mn 1.13, random copolymer; monomer(s): n-octadecyl acrylate; tert-butyl acrylate

Conditions	Yield
With Methyl 2-bromopropionate; copper(I) bromide; 4,4'-di-(5-nonyl)-2,2'-bipyridine; copper(ll) bromide In o-xylene at 100℃; for 10h;

tert-Butyl methacrylate (585-07-9) + octadecylacrylate (4813-57-4) → polymer, Mn 21900 by SEC, Mw/Mn 1.20, gradient copolymer; monomer(s): n-octadecyl acrylate; tert-butyl methacrylate

Conditions	Yield
With ethyl 2-bromoisobutyrate; copper(I) bromide; 4,4'-di-(5-nonyl)-2,2'-bipyridine; copper(ll) bromide In o-xylene at 100℃; for 20h;

polymer, Mn 8300 by SEC, Mw/Mn 1.14; monomer(s): tert-butyl acrylate + octadecylacrylate (4813-57-4) → polymer, Mn 17580 by SEC, Mw/Mn 1.23, diblock copolymer; monomer(s): n-octadecyl acrylate; tert-butyl acrylate

Conditions	Yield
With copper(I) bromide; copper(ll) bromide; 4,4'-di-(5-nonyl)-2,2'-bipyridine In o-xylene at 100℃; for 20h;

octadecylacrylate (4813-57-4) → polymer, Mn 11680 by SEC, Mw/Mn 1.20; monomer(s): n-octadecyl acrylate

Conditions	Yield
With Methyl 2-bromopropionate; copper(I) bromide; 4,4'-di-(5-nonyl)-2,2'-bipyridine; copper(ll) bromide In o-xylene at 90℃; for 30h;

octadecylacrylate (4813-57-4) + 3-(trimethoxysilyl)-1-propanethiol (4420-74-0) → polymer, radical telomerization, polymerization degree: 25; monomer(s): (3-mercaptopropyl)trimethoxysilane, 1 molar part; octadecyl acrylate, 30 molar parts

Conditions	Yield
With azobisisobutyronitrile In ethanol at 80℃; for 6h;

octadecylacrylate (4813-57-4) → poly(octadecyl acrylate)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 59.85℃;

styrene (292638-84-7) + poly(methacrylic acid) (79-41-4) + octadecylacrylate (4813-57-4) + 2,3-Epoxypropyl methacrylate (106-91-2) → Polymer, Mw=8750 (GPC), Tg=66.15 deg C, radical solution copolymerization of methacrylic acid, glycidyl methacrylate, styrene and octadecyl acrylate, 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;

16-methylheptadecanyl methacrylate + octadecylacrylate (4813-57-4) → Reaxys ID: 15742261

Conditions	Yield
With 2,5-dimethyl-2,5-di(2-ethyl hexanoyl peroxy)-hexane In cyclohexane at 80℃;

4-amino-3-tert-butyl-5-methylbenzenethiol (145039-31-2) + octadecylacrylate (4813-57-4) → octadecyl 3-(4-Amino-3-tert-butyl-5-methylphenylthio)propionate

Conditions	Yield
With triethylamine In toluene	8.6 g (72%)

Upstream product

• 112-92-5 1-octadecanol 
• 292638-85-8 acrylic acid methyl ester 
• 74-86-2 acetylene 
• 814-68-6 acryloyl chloride 
• 79-10-7 acrylic acid 

Downstream Products

• 110878-53-0 octadecyl-3-[N,N-dibenzylaminoxy]propanoate 
• 13472-08-7 2,2'-azobis-(2-methylbutyronitrile) 

Relevant articles and documents

Preparation process of long-chain alkyl (meth) acrylate

The invention discloses a preparation process of long-chain alkyl (meth) acrylate, which adopts a polymerization inhibitor composition containing phenothiazine accounting for at least 10% of the totalmass of the composition as a polymerization inhibitor for esterification reaction. The invention solves the problem of self-polymerization in the post-treatment process, can effectively control the acidity of the product to obtain a colorless or white high-purity product, and has the advantages of high yield and expanded application range of the product; in addition, according to the preparationprocess, polymerized excessive (methyl) acrylic acid is recycled, so that a large amount of acid wastewater is prevented from being generated, and the comprehensive benefit is increased.

Synthesis of sialic-acid-group-containing lipid derivatives and application of sialic-acid-group-containing lipid derivatives in pharmaceutical preparations

The invention provides sialic-acid-group-containing lipid derivatives which are widely used for particle preparation modification. The structure is disclosed as Formula (1), wherein R1 represents one of -OH, -HNCOCH3 and -NHCOCH2OH; the HN-R2-S segment is from SH-R2-NH2; SH-R2-NH2 is a compound containing primary amino group and mercapto group; the R3 segment is from compounds containing alpha,beta-unsaturated conjugated carbonyl; and the R4 segment is from R4-H which is a compound containing hydroxy or primary amino group. The sialic-acid-group-containing lipid derivatives provided by the invention can be used for surface modification of multiple particle preparations, and endow the modification preparation with the targeted distribution capacity.

Surface segregation in polymer blends driven by surface freezing

The surface freezing-driven surface segregation in polymer blends was investigated by determining the surface composition and surface temperatures in binary mixtures containing two different lengths of side chains. The chemical attachment of alkyl chains to the backbone was found to lead to considerable differences from the surface freezing in binary alkane mixtures. The surface transition and composition were measured using surface-sensitive infrared-visible sum frequency generation (SFG) spectroscopy and surface tension. The SFG spectra at various blend concentrations were measured as a function of temperature to determine the orientation and concentration of the ordered chains on the surface. The results show that the surface segregation of V22 is sufficient to cover the surface with C22 below Ts22.