trans-Crotonsure

Other Classes -> Organic Acids

Corrosives

Log Kow = 0.72 /isomer not specified/

0.72

0.72

Density = 1.018 at 15 °C/4 °C

Density = 0.9604 g/ cu cm at 77 °C /TRANS ISOMER/

Density = 1.0267 g/ cu cm at 20 °C /CIS ISOMER/

Relative density (water = 1): 1.02

1.018 @ 15°C

MONOCLINIC NEEDLES OR PRISMS (FROM WATER OR PETROLEUM ETHER)

COLORLESS NEEDLE-LIKE CRYSTALS

WHITE CRYSTALLINE SOLID

VERY SOL IN WATER; SOL IN ETHER, ACETONE & IN HOT PETROLEUM ETHER

IN ETHANOL @ 25 °C: 52.5% WT/WT; ACETONE @ 25 °C: 53.0% W/W; IN TOLUENE @ 25 °C: 37.5% WT/WT

Water solubility: 8.6X10+4 mg/l at 25 °C

555 g/l in water at 20 °C

8.60E+04 mg/L @ 25 °C (exp)

190 °F (NFPA, 2010)

190 °F (OPEN CUP)

88 °C o.c.

This chemical does not meet GHS hazard criteria for 0.3% (5 of 1826) of reports.

Danger

H302 (95.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1826 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

This chemical does not meet GHS hazard criteria for 0.4% (1 of 227) of reports.

Chemical: 2-Butenoic acid

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Butenoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butenoic acid 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)

2-Butenoic acid, (2E)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butenoic acid, (2E)- 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)

Status: Active Update: 11-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/10880

2-Butenoic acid, (2E)-: Does not have an individual approval but may be used under an appropriate group standard

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

· Combustible material: may burn but does not ignite readily.

Combustible. Risk of fire and explosion on contact with incompatible substances. See Chemical Dangers. Above 88 °C explosive vapour/air mixtures may be formed.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

A strong tissue irritant; [Hawley] May polymerize on exposure to UV light or moisture; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause pulmonary edema; [ICSC] Emergency treatment: acids; [HSDB]

2823 153

3472 153

CROTONIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

The substance may polymerize under the influence of UV light or moisture. This generates fire and explosion hazard. The solution in water is a weak acid. Reacts violently with strong bases and peroxides. This generates fire and explosion hazard.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Seek medical attention if you feel unwell.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention if skin irritation occurs.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Seek medical attention if you feel unwell.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

General First Aid:

General First Aid:

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.

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.

Evacuate danger area! Remove all ignition sources. Consult an expert! Personal protection: face shield. Do NOT let this chemical enter the environment. Let solidify. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.

If material not on fire and not involved in fire: Keep material out of water sources and sewers. Neutralize spilled material with crushed limestone, soda ash, or lime.

Personnel protection: Avoid breathing vapors. Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. If contact with the material anticipated, wear appropriate chemical protective clothing.

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.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

Immediate precautionary measure

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 59(SRC), determined from a measured log Kow of 0.72(2) and a regression-derived equation(3), indicates that crotonic acid is expected to have high mobility in soil(SRC). Volatilization of trans-crotonic acid is not expected to be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.4X10-7 atm-cu m/mole(SRC), determined from a vapor pressure of 0.18 mm Hg at 20 °C(4) and a measured water solubility of 8.6X10+4 mg/l at 25 °C(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 59(SRC), determined from a measured log Kow of 0.72(2) and a regression-derived equation(3), indicates that crotonic acid is not expected to adsorb to suspended solids and sediment in water(SRC). trans-Crotonic acid is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.4X10-7 atm-cu m/mole(SRC), determined from a vapor pressure of 0.18 mm Hg at 20 °C(4) and a measured water solubility of 8.6X10+4 mg/l at 25 °C(5). According to a classification scheme(6), an estimated BCF value of 2.1(3,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Crotonic acid was biodegraded by anaerobic bacteria to butyrate and acetate(7-9). After a lag period of 2 days, crotonic acid was metabolized, at a rate of 200 mg/l day, by anaerobic bacteria acclimated to acetate culture(9). Crotonic acid reached 44% of its theoretical BOD in 5 days using a sewage inoculum(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trans-crotonic acid, which has a vapor pressure of 0.18 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase trans-crotonic acid 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 17 hours(3,SRC).

Cough. Sore throat.

Redness.

Redness. Pain. Burning sensation. Burns.

Sore throat.

Crotonic acid was identified as an oxygenated organic emission from bench-scale fires using individual components derived from ponderosa pine as fuel(1). Smoldering wood fires emitted crotonic acid at a mean concentration of 0.068 g/kg; smoldering needle fires emitted crotonic acid at a mean concentration of 0.037 g/kg; smoldering bark fires emitted a mean crotonic acid concentration of 0.039 g/kg; self-sustained smoldering bark fires emitted 0.03 g/kg crotonic acid; and smoldering litter (consisting primarily of loose brown needles, with lesser amounts of cones, bark, grass) fires emitted a mean concentration of 0.04 g/kg crotonic acid(1).

The Koc of crotonic acid is estimated as approximately 59(SRC), using a measured log Kow of 0.72(1) and a regression-derived equation(2,SRC). According to a classification scheme(3), this estimated Koc value suggests that crotonic acid is expected to have high mobility in soil(SRC).

Crotonic acid's production and use in the synthesis of resins, polymers, plasticizers, and drugs(1) may result in its release to the environment(SRC). Only the trans form of crotonic acid and its derivatives have industrial importance as monomers in copolymerization reactions and as intermediates in the synthesis of pharmaceuticals or fungicides(2).

Crotonic acid (mixture) was identified as being amenable to anaerobic biodegradation(1). Anaerobic bacteria isolated from mesophilic digester sludge acclimatized with 4-chlorobutyrate tentatively classified in the genus Clostridium, degraded crotonate to butyrate, acetate, and hydrogen(2). Ilyobacter polytropus anaerobically degraded crotonate to butyrate and acetate(2). Crotonate was degraded by an anaerobic bacterium to butyrate and acetate(3). After a lag period of 2 days, crotonic acid (isomer not specified) was metabolized, at a rate of 200 mg/l day, by anaerobic bacteria acclimated to acetate culture(4). Crotonic acid (isomer not specifed) reached 44% of its theoretical BOD in 5 days using a sewage inoculum(5).

An estimated BCF value of 2.1 was calculated for crotonic acid(SRC), using a measured log Kow of 0.72(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

Used to make copolymers (for lacquers, paper sizing, resins, plasticizers, and drugs) and softening agents for synthetic rubber; Also used as a coating, fungicide, and corrosion-resistant additive; [HSDB]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

MFR OF COPOLYMERS WITH VINYL ACETATE USED IN LACQUERS & PAPER SIZING; MFR OF SOFTENING AGENTS FOR SYNTHETIC RUBBER; IN MEDICINAL CHEMISTRY, EG, MFR OF DL-THREONINE, VIT A

Coating, resins, fungicide, corrosion resistance improvement additive. Water-soluble resins and copolymers are suitable for pharmaceuticals, binders, and film

Chemical modifications rendering the surface layers of silicone rubber contact lenses hydrophilic property.

Carboxylated comonomer (polyvinyl acetate latex).

2023: 224,869 lb

2023: 7,040 lb

Monomers

Not Known or Reasonably Ascertainable

Obtained on a commercial scale exclusively by oxygen-air-oxidation of crotonaldehyde.

LAB PROCEDURE USING ALKALINE SILVER OXIDE; FROM ACETALDEHYDE & MALONIC ACID IN PYRIDINE.

Isomerization of vinylacetic acid by warming with 50% sulfuric acid.

GRADE: 97%

Technical grade, 98.5% min

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Cosmetics -> Stabilizing

All Other Basic Organic Chemical Manufacturing

Not Known or Reasonably Ascertainable

2-Butenoic acid: ACTIVE

IT /CROTONIC ACID/ IS PRESENT AS CONSTITUENT OF CROTON OIL.

Only the trans form of crotonic acid and its derivatives have industrial importance as monomers in copolymerization reactions and as intermediates in the synthesis of pharmaceuticals or fungicides.