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

Used in Cosmetics Industry:
Octadecyl acrylate is used as a film former for [application reason] to help maintain moisture in the skin. Its film-forming properties create a protective barrier that helps to lock in moisture, providing hydration and improving the skin's overall appearance.
Used in Polymer Industry:
Octadecyl acrylate is used as a reagent for [application reason] in the synthesis of comb-like polymers. These polymers are then incorporated into waterborne latexes, improving their barrier properties. The enhanced barrier properties can be beneficial in various applications, such as coatings, adhesives, and sealants, where resistance to water and other environmental factors is desired.

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 
• 79-10-7 acrylic acid 
• 814-68-6 acryloyl chloride 

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.

Preparation method for synthesizing high-carbon alkyl acrylate through catalyzing in-situ acid resin

The invention belongs to the technical field of organic synthesis and in particular relates to a preparation method for synthesizing high-carbon alkyl acrylate through catalyzing in-situ acid resin. The preparation method comprises the following steps: mixing acrylic acid, the in-situ acid resin, acrylic high-carbon alkyl alcohol, hydroquinone and cyclohexane according to a certain ratio; stirringand heating, and controlling reaction time; after reaction is finished, filtering to remove a resin catalyst; carrying out water washing, neutralization and water washing to obtain the high-carbon alkyl acrylate. According the preparation method provided by the invention, the yield of high-carbon alkyl acrylate can be improved; the in-situ acid resin can be repeatedly utilized, resources are saved and the environment is protected.

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.

Continuous Method For Producing Esters Of Aliphatic Carboxylic Acids

The invention relates to a continuous method for producing aliphatic carbonic acid esters by reacting at least one aliphatic carboxylic acid of formula (I) R1—COOH (I), wherein R1 represents hydrogen or an optionally substituted aliphatic hydrocarbon group with 1 to 50 carbon atoms, with at least one alcohol of formula (II) R2—(OH)n (II), wherein R2 represents an optionally substituted hydrocarbon group with 1 to 100 C atoms and n is an integer from 1 to 10, in the presence of at least one transesterification catalyst in a reaction tube the longitudinal axis of which extends in the direction of propagation of the microwaves of a monomode microwave applicator, under microwave irradiation to form the ester.

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.

Designing polymers for biphasic liquid/liquid separations after homogeneous reactions

The phase-selective solubility properties of polymer supports that could be used in thermomorphic and latent biphasic systems useful in synthesis and catalysis were evaluated using polymers tagged with either visible dyes or fluorescent probes. Heptane/DMF, heptane/90% ethanol-water, heptane/ethyl acetate, heptane/ethanol, and heptane/tert-butyl alcohol solvent mixtures were all studied as examples of thermomorphic or latent biphasic systems. A range of polymers including polyisobutylene (PIB), poly(tert-butylstyrene) (PTBS), poly(octadecyl acrylate) (PODA), and poly(octadecyl methacrylate) (PODMA) were tested for hydrophobic phase-selective solubility. The results of these studies are compared to prior work with polar and nonpolar poly(N-alkylacrylamide)s and polystyrene. Together with this prior work, these results show that a wide range of polymers and solvent mixtures can be used for the recycling of soluble polymer-bound catalysts, reagents, and sequestrants using either thermomorphic or latent biphasic separation strategies.

Preparation of preparing substituted indanones

a process for the preparation of indanones of the formula II from, indanones of the formula I or of indanones of the formula IIa from indanones of the formula Ia comprises reacting an indanone of the formula I or Ia with a coupling component.