56927-66-3

Basic information

• Product Name: 2-Propenoic acid, 2-methyl-, 10-hydroxydecyl ester
• Synonyms: 10-Hydroxydecylmethacrylat;2-Propenoic acid,2-methyl-,10-hydroxydecyl ester
• CAS NO: 56927-66-3
• Molecular Formula: C14H26O3
• Molecular Weight: 242.359
• Mol File: 56927-66-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 2-methyl-, 10-hydroxydecyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 2-methyl-, 10-hydroxydecyl ester(56927-66-3)
• EPA Substance Registry System: 2-Propenoic acid, 2-methyl-, 10-hydroxydecyl ester(56927-66-3)

Safety Data

• Hazardous Substances Data: 56927-66-3(Hazardous Substances Data)

Usage

General Description

2-Propenoic acid, 2-methyl-, 10-hydroxydecyl ester, also known as hydroxylated decyl methacrylate, is a chemical compound commonly used in the production of acrylic polymers and resins. It is a clear, colorless liquid with a characteristic odor, and is insoluble in water but soluble in organic solvents. It is primarily used in the manufacturing of adhesives, coatings, dental materials, and as a reactive diluent in UV-curable coatings. 2-Propenoic acid, 2-methyl-, 10-hydroxydecyl ester is known for its ability to improve adhesion, flexibility, and impact resistance in various polymer applications. It is considered to be an important building block in the chemical industry for creating high-performance materials.

Synthetic route

1,10-Decanediol (112-47-0) + poly(methacrylic acid) (79-41-4) → 10-hydroxydecyl methacrylate (56927-66-3)

Conditions	Yield
With toluene-4-sulfonic acid at 85℃; for 10h; Temperature;	60%
With silica gel supported sodium hydrogen sulfate; hydroquinone at 80℃; for 0.333333h; Concentration;

1,10-Decanediol (112-47-0) + poly(methacrylic acid) (79-41-4) → 1,10-decamethylene glycol dimethacrylate (6701-13-9) + 10-hydroxydecyl methacrylate (56927-66-3)

Conditions	Yield
With toluene-4-sulfonic acid; 4-methoxy-phenol In hexane for 15h; Reflux;	A n/a B 52%
With 2,6-di-tert-butyl-4-methyl-phenol; toluene-4-sulfonic acid at 85℃; for 4h;

10-hydroxydecyl methacrylate (56927-66-3) + phosphorous acid trimethyl ester (121-45-9) → methacryloyloxydecyl dimethoxy phosphate

Conditions	Yield
With pyridine; carbon tetrabromide at 20℃; for 7h; Time; Cooling with ice; Inert atmosphere;	63.5%

10-hydroxydecyl methacrylate (56927-66-3) → 10-methacryloyloxydecyl dihydrogen phosphate (85590-00-7)

Conditions	Yield
Stage #1: 10-hydroxydecyl methacrylate With triethylamine; trichlorophosphate In tetrahydrofuran at -40℃; for 3h; Stage #2: With water In tetrahydrofuran at -40℃; for 0.25h;
With triethylamine; trichlorophosphate In diethyl ether; water at -40 - 0℃; Inert atmosphere;	64.8 g

10-hydroxydecyl methacrylate (56927-66-3) → 10-(phosphono)oxydecyl methacrylate (255043-14-2)

Conditions	Yield
Stage #1: 10-hydroxydecyl methacrylate With triethylamine; trichlorophosphate In tetrahydrofuran at -4℃; for 3h; Inert atmosphere; Stage #2: With water In tetrahydrofuran for 5h; Inert atmosphere;

Upstream product

• 112-47-0 1,10-Decanediol 
• 79-41-4 poly(methacrylic acid) 
• 53463-68-6 1-bromo-10-decanol 
• 6900-35-2 potassium methacrylate 

Downstream Products

• 85590-00-7 10-methacryloyloxydecyl dihydrogen phosphate 

Relevant articles and documents

METHOD FOR PRODUCING (METH)ACRYLATE COMPOUND CONTAINING HYDROXYL GROUP AND METHOD FOR PRODUCING (METH)ACRYLATE COMPOUND CONTAINING PHOSPHORIC ACID GROUP

PROBLEM TO BE SOLVED: To provide a method for producing a (meth)acrylate compound containing a hydroxyl group, which, when producing a (meth)acrylate compound containing a hydroxyl group, can suppress formation of by-products. SOLUTION: Provided is a method for producing a (meth)acrylate compound (A) which is a (meth)acrylate compound containing a hydroxyl group, comprising a step of reacting an alcohol compound containing a halogen atom and a (meth)acrylic acid salt to obtain the (meth)acrylate compound (A). SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Oral adhesive methacryloyl decyl dihydro phosphorus acid ester synthetic method

The invention provides a synthetic method of 10-methacryloyloxydecyl dihydrogen phosphate. The method comprises the steps of preparing an intermediate 10-hydroxyldecanoyl methacrylate, preparing 10-methacryloyloxydecyl dimethoxy phosphate, and preparing the above target product. In the monoester synthesis process, a solvent-free reduced pressure distillation technology is adopted for the first time, so the environmental pollution problem caused by the use of an organic solvent is avoided, the cost is reduced, and unreacted raw materials can be recycled; in the phosphorylation process, trimethyl phosphite is adopted as an acylation reagent for the first time, and the reaction is carried out at room temperature under mild conditions, so the energy consumption is reduced, the environmental pollution problem caused by phosphorous oxychloride and other acylating agents is avoided, and the unreacted raw material 10-hydroxyldecanoyl methacrylate can be recycled; and a freeze-drying technology adopted in hydrolysis post-treatment avoids complicated operation of column chromatography and the mass use of an organic solvent, realizes low cost, environmental protection, mild reaction conditions, high product yield reaching 87.0% and high product purity, and is suitable for industrial production.

SELF-ETCHING DENTAL COMPOSITIONS AND METHODS

The present invention is directed to dental compositions that can be used as adhesives for bonding a dental material to a dental structure surface and/or as a dental restorative material. The dental composition is preferably applied to a dental structure surface under conditions effective to etch the dental structure surface.