Basic information
- CAS
27813-02-1- Standard SMILES
C=C(C)C(=O)OC(C)CO- InChIKey
ZMARGGQEAJXRFP-UHFFFAOYSA-N- Molecular formula
- C7H12O3
- Average molar mass
- 144.17 g/mol
- Monoisotopic mass
- 144.07864424
Overview
Hydroxypropyl methacrylate appears as white liquid with a light unpleasant odor. May float or sink in water. (USCG, 1999)
Names & identifiers
- Preferred name
- Hydroxypropyl Methacrylate
- IUPAC
- 1-hydroxypropan-2-yl 2-methylprop-2-enoate
- English name
- 2-Hydroxypropyl methacrylate
- Molecular formula
- C7H12O3
- Molecular weight
- 144.17
Names & synonyms
Show more names
Database identifiers
- CAS
27813-02-1、4664-49-7- PubChem CID
- 34023
- DTXSID
DTXSID40867417- UNII
- BC693EJ6V3
- EC Number
- 225-109-2、248-666-3
- Nikkaji
- J175.473D
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 140
Experimental & physicochemical properties
Density
1.06 at 68 °F (USCG, 1999) - Denser than water; will sink
1.066 @ 25 °C/16 °C
Flash Point
250 °F (USCG, 1999)
250 °F (open cup)
121 °C (Cleveland open cup)
Boiling Point
Boiling point: 87 °C @ 0.67 kPa; Specific gravity: 1.028 @ 25 °C /2-Hydroxypropyl methacrylate/
Boiling point: 96 °C @ 1.3 kPa /2-Hydroxypropyl methacrylate/
Polymerization
Compound may polymerize when hot and burst container. May polymerize ... when exposed to ultraviolet light and free-radical catalysts.
METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/
Physicochemical properties
- Melting point
- -58 °C · -58°C
- Boiling point
- 57 °C/0.5 · 57 °C/0.5 mmHg (lit.)
- Density
- 1.066 g/mL · 1.066 g/mL at 25 °C (lit.)
- vapor density
- 1 · >1 (vs air)
- vapor pressure
- 0.05 mm · 0.05 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.447(lit.)
- Flash point
- 206 °F · 206 °F
- storage temp.
- 2 · 2-8°C
- solubility
- 107 g/l · 107g/l
- form
- Liquid
- Specific Gravity
- 1.066 · 1.066
- color
- Clear
- PH
- 6 · 6 (50g/l, H2O, 20℃)
- Viscosity
- 8.88 mm2/s · 8.88mm2/s
- Water Solubility
- Soluble in water.
- BRN
- 1752228 · 1752228
- Cosmetics Ingredients Functions
- FILM FORMING
- InChIKey
- GNSFRPWPOGYVLO-UHFFFAOYSA-N
- LogP
- 0.97 at · 0.97 at 20℃
- CAS DataBase Reference
- 27813 · 27813-02-1(CAS DataBase Reference)
- Indirect Additives used in Food Contact Substances
- HYDROXYPROPYL METHACRYLATE
- FDA 21 CFR
- 175.105 · 175.105; 177.1010
- FDA UNII
- 89 XAX2X · UKW89XAX2X
- EPA Substance Registry System
- Hydroxypropyl methacrylate (27813-02-1)
- UNSPSC Code
- 12162002 · 12162002
- NACRES
- 23 · NA.23
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 315 · H315-H317-H319-H335-H340-H350
- Precautionary statements
- 201 · P201-P202-P280-P302+P352-P305+P351+P338-P308+P313
- Hazard Codes
- Xi,T
- Risk Statements
- 36 · 36/37/38-43-36-46-45
- Safety Statements
- 26 · 26-36/37-37/39-24/25-45-53
- WGK Germany
- 1 · 1
- RTECS
- 3442500 · UD3442500
- TSCA
- TSCA listed
- HS Code
- 29161490 · 29161490
- Hazardous Substances Data
- 27813 · 27813-02-1(Hazardous Substances Data)
- Toxicity
- 50 · rat,LD50,oral,11200mg/kg (11200mg/kg),LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMAGASTROINTESTINAL: OTHER CHANGESLUNGS, THORAX, OR RESPIRATION: DYSPNEA,National Technical Information Service. Vol. OTS0544834,
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.8% (12 of 1419) of reports.
Warning
H317 (97%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1419 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
Hazard information
Regulatory Information
Chemical: 2-Propenoic acid, 2-methyl-, 2-hydroxy-1-methylethyl ester
Chemical: 2-Propenoic acid, 2-methyl-, monoester with 1,2-propanediol
2-Propenoic acid, 2-methyl-, monoester with 1,2-propanediol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, monoester with 1,2-propanediol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: Methacrylic acid, monoester with propane-1,2-diol (EC: 248-666-3)
2-Propenoic acid, 2-methyl-, monoester with 1,2-propanediol: Does not have an individual approval but may be used under an appropriate group standard
Health Hazards
Inhalation causes coughing and irritation of nose and throat; lung injury may occur. Ingestion causes irritation and burning of mouth and stomach. Contact of vapor with eyes causes irritation. Liquid may cause severe eye burns and irritation of skin. (USCG, 1999)
Hazards Summary
Allergic contact dermatitis reported in dental technicians; [Kanerva, p. 1743] An eye, nose, and throat irritant; [HSDB] May polymerize; A skin, eye, nose, and throat irritant; May cause injury to lungs and eyes; [CAMEO] May polymerize on exposure to light or heat; An irritant; May cause skin sensitization; [MSDSonline] See ACRYLIC RESINS (MONOMERS).
Hazard Classes and Categories
Skin Sens. 1 (97%)
Eye irritation - category 2A
Serious eye damage/eye irritation - Category 2
Safety & protection
Storage Conditions
Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for the polyfunctional methacrylates. ... The methacrylate monomers should not be stored for longer than one year. Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months. Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark. The methacrylic esters may be stored in mild steel, stainless steel, or aluminum. /Methacrylic acid & derivatives/
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Preventive Measures
... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Personal Protective Equipment (PPE)
Goggles or face shield; rubber gloves (USCG, 1999)
SUITABLE PROTECTIVE CLOTHING & SELF-CONTAINED RESP PROTECTIVE APPARATUS SHOULD BE AVAILABLE FOR USE OF THOSE WHO MAY HAVE TO RESCUE OF PERSONS OVERCOME BY FUMES. /ACRYLIC ACID & DERIVATIVES/
Goggles or face shield; rubber gloves.
Toxicology
Toxicity Summary
Based on available data, the CIR Expert Panel concluded that ...Hydroxypropyl Methacrylate is safe as used in nail enhancement products when skin contact is avoided. Products containing these ingredients should be accompanied with directions to avoid skin contact, because of the sensitizing potential of Methacrylates.
Safe for use in cosmetics, with qualifications
Antidote and Emergency Treatment
Basic treatment: Establish a patent airway. Suction if necessary. Encourage patient to take deep breaths. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Irritating materials/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation at the first sign of upper airway obstruction may be necessary. Positive-pressure ventilation techniques with a bag-valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Irritating materials/
Safety data
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- UD3442500
- hs_code
- 29161490
- Toxicity
- rat,LD50,oral,11200mg/kg (11200mg/kg),LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMAGASTROINTESTINAL: OTHER CHANGESLUNGS, THORAX, OR RESPIRATION: DYSPNEA,National Technical Information Service. Vol. OTS0544834,
- risk_code
- 36/37/38-43-36-46-45
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xi,T
- safety_code
- 26-36/37-37/39-24/25-45-53
- Hazard statements
- H315-H317-H319-H335-H340-H350
- REACH Registrations
- Active
- Precautionary statements
- P201-P202-P280-P302+P352-P305+P351+P338-P308+P313
- Hazardous Substances Data
- 27813-02-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
CIR ingredient: Hydroxypropyl Methacrylate
Used as monomer (i.e. acrylic resins, nonwoven fabric binders, and detergent lube oil additives) and in elastomers, laminating resins, and dental filling materials; [HSDB]
Textiles (Fiber & Fabric Manufacturing) [Category: Industry]
COMONOMER IN CROSS-LINKED-THERMOSET-ACRYLIC COATING RESINS; FOR ELASTOMERS, FOR LAMINATING RESINS; MONOMER FOR NONWOVEN FABRIC BINDER
IN DENTAL FILLING MATERIAL
Monomer for acrylic resins, detergent lube oil additives; nonwoven fabric binders
Methods of Manufacturing
ADDITION OF PROPYLENE OXIDE TO METHACRYLIC ACID WITH A BASE AS CATALYST
Hydroxyalkyl methacrylates are prepared by the addition of methacrylic acid to the epoxide ring of alkylene oxides to form hydroxyalkyl methacrylates, ie, beta-hydroxyethyl and hydroxypropyl methacrylate. Oxides other than ethylene oxide give isomeric products; commercial hydroxypropyl methyacrylate has about a 2-to-1 ratio of 2-hydroxypropyl methacrylate to 1-methyl-2-hydroxyethyl methacrylate. Effective catalysts include tertiary amines, anion-exchange resins, ferric chloride, and lithium methacrylate.
The methacrylates can be synthesized by catalytic oxidation of isobutylene and subsequent esterification with the appropriate alcohol, or by reacting acetone with hydrocyanic acid and subsequent esterification in sulfuric acid with the appropriate alcohol. /Methacrylic esters/
Formulations/Preparations
Inhibitior of polymerization: 200 ppm hydroquinone
Grades of purity: Commercial, 95+%
Typical inhibitor level: 1200 ppm monomethyl ether hydroquinone
General Manufacturing Information
Electrical Equipment, Appliance, and Component Manufacturing
2-Propenoic acid, 2-methyl-, monoester with 1,2-propanediol: ACTIVE
METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/
Applications
DescriptionHydroxypropyl methacrylate(HPMA) is a clear, colorless liquid with a pungent, sweet odor. The product contains low levels of a polymerization inhibitor along with small amounts of methacrylic acid, and propylene oxide. HPMA is used in the manufacture of acrylic polymers for adhesives, inks, and coatings for automotive, appliance and metal applications. The added hydroxyl groups improve adhesion to surfaces, incorporate cross-link sites, and impart corrosion, fogging, and abrasion resistance.
UsesMonomer for acrylic resins, nonwoven fabric binders, detergent lubricating-oil additives.
UsesHydroxypropyl methacrylate is a functional monomer for the preparation of hot solid acrylic coatings, styrene-butadiene latex modifiers, acrylic modified polyurethane coating ,water-soluble plating coatings , adhesives ,textile finishing agent ,paper coating , photosensitive paint and polyurethane vinyl resin modified agent. Mainly used in the manufacture are active groups of hydroxyl acrylic resin. Used in reactive diluent and cross-linking agent in the UV curing system.
General DescriptionWhite liquid with a light unpleasant odor. May float or sink in water.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers5 total
Additional notes
DefinitionChEBI: 2-hydroxypropyl methacrylate is an enoate ester that is the 1-methacryloyl derivative of propane-1,2-diol. It has a role as a polymerisation monomer. It is functionally related to a propane-1,2-diol and a methacrylic acid.
Related reactions
Compound notes
Loading…