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Methyl propionate

Methyl propionate structure

Methyl propionate 

structure
  • CAS No:

    554-12-1

  • Formula:

    C4H8O2

  • Chemical Name:

    Methyl propionate

  • Synonyms:

    Propanoic acid,methyl ester;Propionic acid,methyl ester;Methyl propionate;Methyl propanoate;Methyl propylate;NSC 9375

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

colourless liquid Methyl propionate is colorless liquid with a sweet, fruity, rum-like odor. Methyl propionate has a fruity odor reminiscent of rum with a sweet flavor suggestive of black currant. May be prepared by direct esterification of the acid with methanol in the presence of concentrated H2S04. Methyl propionate has a fruity odor reminiscent of rum. It has a sweet flavor suggestive of black currant


Methyl propionate appears as a clear colorless liquid. Flash point 28°F. Density about the same as water. Vapors heavier than air. May irritate skin, eyes, and mucous membranes. Used for flavoring and as a solvent.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.|colourless to pale yellow liquid with a fruity, rum odour


Methyl propionate appears as a clear colorless liquid. Flash point 28°F. Density about the same as water. Vapors heavier than air. May irritate skin, eyes, and mucous membranes. Used for flavoring and as a solvent.|Methyl propionate is a carboxylic ester.

Methyl propionate Basic Attributes

88.11

88.11

1737628

209-060-4

NB21C0D33W

1029

9375

1248

DTXSID7027201

Colorless liq

2915509000

Characteristics

26.3

0.82

Clear colorless Liquid

0.915 g/cm3 @ Temp: 20 °C

-87.5 °C

79.8 °C

43 °F

1.373

H2O: 5 g/100 mL at 20 ºC

Flammables area

40 mm Hg ( 11 °C)

3 (vs air)

Oral-Rat LD50: 5000 mg/kg; Oral-Mouse LD50: 3460 mg/kg

Inflammable in case of open flame, high temperature, oxidant; burning produces irritating smoke

2.5-13%(V)

SWEET, FRUITY, RUM-LIKE ODOR

SWEET, RUM TASTE

1.00e-12 cm3/molecule*sec

1.74e-04 atm-m3/mole|Henry's Law constant= 1.74X10-4 atm cu m/mole @ 25 °C

When heated to decomposition it emits acrid smoke and irritating fumes.

Highly flammable. Soluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Highly Flammable

METHYL PROPIONATE reacts 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 with caustic solutions. Flammable hydrogen is generated with alkali metals and hydrides.

873 °F (NTP, 1992)|876 °F (469 °C)|469 °C

Lower Flammable Limit: 2.5% by volume; Upper Flammable Limit: 13% by volume

The vapour is heavier than air and may travel along the ground; distant ignition possible. As a result of flow, agitation, etc., electrostatic charges can be generated.

Safety Information

II

3

UN 1248 3/PG 2

1

11-20-2017/11/20

16-24-29-33

UF5970000

F,Xn

Treasury is ventilated, low temperature and dry; stored separately from oxidant

Explosive when mixed with air

Stable. Highly flammable. Incompatible with strong oxidizing agents, acids, bases. Readily forms explosive mixtures with air. Moisture sensitive.

P210

H225-H332

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.

Methyl propionate is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient. Synthetic flavoring substances and adjuvants /incl methyl propionate/ may be safely used in foods.

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)|Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.|Flammable - 3rd degree

|Danger|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P312, P304+P340, P312, P370+P378, P403+P235, and P501|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|Aggregated GHS information provided by 1616 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)

Flammable, dangerous fire risk ...|A very dangerous fire hazard when exposed to heat, flame, or oxidizers.

EXPLOSIVE LIMITS IN AIR: 2.5%-13%|Explosive in the form of vapor when exposed to heat or flame.|Explosive limits , vol% in air: 2.5-13.0

WATER MAY BE INEFFECTIVE.|To fight fire, use foam, carbon dioxide, dry chemical.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.|For more DOT Emergency Guidelines (Complete) data for METHYL PROPIONATE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

A skin irritant.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Remove all ignition sources. Collect leaking and spilled liquid in covered containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

Fireproof. Cool. Separated from oxidants.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the respiratory tract, skin and eyes.

NO open flames, NO sparks and NO smoking. NO contact with oxidizing agents. Closed system, ventilation, explosion-proof electrical equipment and lighting. Prevent build-up of electrostatic charges (e.g., by grounding). Use non-sparking handtools.

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety goggles or eye protection in combination with breathing protection.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Methyl propionate was one of the volatile compounds identified, not quantified, from kitchen waste exudate and in stored food exudates in a study conducted in Denmark(1). It was also detected in the liquid exudate from garden waste(2).

Toxicity

moderately toxic

LD50 RAT ORAL 5 G/KG|LD50 Rabbit oral 2.02 g/kg|LD50 Mouse oral 3460 mg/kg

PROBABLY OCCURRING IN CALIFORNIA ORANGE (VARIETY VALENCIA) JUICE & HONEY.|Occurs naturally ... in fermented egg, and in several fruits including apple, banana, melon, pineapple, and strawberry.|Methyl propionate has been detected as a volatile component of kiwi fruit(1) and Sivetta variety strawberries(2).

Methyl propionate's production and use as an solvent and flavoring agent(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 66(SRC), determined from a log Kow of 0.82(2) and a regression-derived equation(3), indicates that methyl propionate is expected to have high mobility in soil(SRC). Volatilization of methyl propionate from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.74X10-4 atm-cu m/mole(4). The potential for volatilization of methyl propionate from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 84 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation in soil is expected based upon aqueous biodegradation studies; methyl propionate was 100% degraded in 5 days under anaerobic conditions with aquifer slurries(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 66(SRC), determined from a log Kow of 0.82(2) and a regression-derived equation(3), indicates that methyl propionate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.74X10-4 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7 hrs and 5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 2.5(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation in aquatic environments may be an important fate process(7,8). Aqueous hydrolysis will be important only in very alkaline environmental waters with an estimated half-life of 74 days at pH 8(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl propionate, which has a vapor pressure of 84 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl propionate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 24 days(SRC), calculated from its rate constant of 0.6744X10-12 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3). Physical removal from air via wet deposition (dissolution into clouds, rainfall, etc) is likely since it is relatively soluble in water(4).

The rate constant for the vapor-phase reaction of methyl propionate with photochemically-produced hydroxyl radicals is 1.0X10-12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 24 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.108 L/mol-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 2 yrs and 74 days at pH values of 7 and 8, respectively(SRC). The rate constant for the reaction between photochemically produced hydroxyl radicals in water and methyl propionate is 4.5X10+8 L/mole-sec(3); assuming that the concn of hydroxyl radicals in brightly sunlit natural water is 1X10-17 M(4), the half-life would be about 1780 days of continuous (24 hr/day) sunlight(SRC).

An estimated BCF of 2.5 was calculated for methyl propionate(SRC), using a log Kow of 0.82(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

The Koc of methyl propionate is estimated as 66(SRC), using a log Kow of 0.82(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that methyl propionate is expected to have high mobility in soil.

The Henry's Law constant for methyl propionate is 1.74X10-4 atm-cu m/mole(1). This Henry's Law constant indicates that methyl propionate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 7 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 5 days(SRC). Methyl propionate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of methyl propionate from dry soil surfaces may exist(SRC) based upon a vapor pressure of 84 mm Hg(3).

Methyl propionate concns of 0.2-0.9% were detected in the volatile components of mature and ripe kiwi fruit collected in New Zealand and Australia(1). The compound was also detected, not quantified, in headspace analyses of Sivetta variety strawberry samples held in a closed system(2).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,821 workers (273 of these are female) are potentially exposed to methyl propionate in the US(1). Occupational exposure to methyl propionate may occur through inhalation of this compound at workplaces where methyl propionate is produced or used(SRC). The general population may be exposed to methyl propionate via ingestion of certain fruits(2,3) and shellfish(4), and use of solvent products(5) containing methyl propionate.

Drug Information

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


Fresh air, rest.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Basic treatment: Establish a patent airway. Suction if necessary. 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 ... 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. Administer activated charcoal ... /Esters and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. 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. For hypotension with signs of hypovolernia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... Consider drug therapy for pulmonary edema ... Use proparacaine hydrochloride to assist eye irrigation ... /Esters and related compounds/

BY ORAL ADMIN TO ANIMALS METHYL PROPIONATE APPEARS TO BE SLIGHTLY MORE TOXIC THAN ETHYL PROPIONATE, BUT NO TOXIC EFFECTS IN HUMAN BEINGS HAVE BEEN REPORTED.

Cough. Sore throat.


Redness.


Redness. Pain.

Methyl propionate Use and Manufacturing

Methods of Manufacturing

Derived from the esterification of propionic acid and methanol. Mix 5kg propionic acid, 3kg methanol and 300g sulfuric acid, heat to reflux for 6-8h, separate the sulfuric acid layer, and cool the ester layer. The ester layer was washed with brine of the same volume as the crude ester, and washed with sodium carbonate solution until it was acid-free. After drying, fractionation was conducted to obtain 3.5 L of methyl propionate.

Uses

In organic synthesis.

Production

(1981) PROBABLY GREATER THAN 4.54X10+5 G|(1982) PROBABLY GREATER THAN 4.54X10+5 G

USE IN FRAGRANCES IN THE USA AMOUNTS TO LESS THAN 1000 POUNDS PER YEAR.

Grade: Technical

Propanoic acid, methyl ester: ACTIVE|FLAVORS USEFUL IN: RUM, BLACK CURRANT, FRUIT BLENDS

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty esters [FA07] -> Wax monoesters [FA0701]|Fire Hazards -> Flammable - 3rd degree

Flavoring Agents

Computed Properties

Molecular Weight:88.11
XLogP3:0.8
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:88.052429494
Monoisotopic Mass:88.052429494
Topological Polar Surface Area:26.3
Heavy Atom Count:6
Complexity:49.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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