Acrolein
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Names | |||
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Preferred IUPAC name
Prop-2-enal | |||
Other names | |||
Identifiers | |||
3D model (
JSmol ) |
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.003.141 | ||
EC Number |
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IUPHAR/BPS |
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KEGG | |||
PubChem CID
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RTECS number
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UNII | |||
UN number | 1092 | ||
CompTox Dashboard (EPA)
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Properties | |||
C3H4O | |||
Molar mass | 56.064 g·mol−1 | ||
Appearance | Colorless to yellow liquid. Colorless gas in smoke. | ||
Odor | Acrid, Foul, Irritating | ||
Density | 0.839 g/mL | ||
Melting point | −88 °C (−126 °F; 185 K) | ||
Boiling point | 53 °C (127 °F; 326 K) | ||
Appreciable (> 10%) | |||
Vapor pressure | 210 mmHg[1] | ||
Hazards[3] | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
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Highly poisonous. Causes severe irritation to exposed membranes. Extremely flammable liquid and vapor. | ||
GHS labelling: | |||
Danger | |||
H225, H300, H311, H314, H330, H410 | |||
P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P273, P280, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | −26 °C (−15 °F; 247 K) | ||
278 °C (532 °F; 551 K) | |||
Explosive limits
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2.8-31%[1] | ||
Lethal dose or concentration (LD, LC): | |||
LC50 (median concentration)
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875 ppm (mouse, 1 min) 175 ppm (mouse, 10 min) 150 ppm (dog, 30 min) 8 ppm (rat, 4 hr) 375 ppm (rat, 10 min) 25.4 ppm (hamster, 4 hr) 131 ppm (rat, 30 min)[2] | ||
LCLo (lowest published)
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674 ppm (cat, 2 hr)[2] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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TWA 0.1 ppm (0.25 mg/m3)[1] | ||
REL (Recommended)
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TWA 0.1 ppm (0.25 mg/m3) ST 0.3 ppm (0.8 mg/m3)[1] | ||
IDLH (Immediate danger) |
2 ppm[1] | ||
Safety data sheet (SDS) | Sigma-Aldrich SDS | ||
Related compounds | |||
Related alkenals
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Crotonaldehyde cis-3-Hexenal (E,E)-2,4-Decadienal
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Acrolein (systematic name: propenal) is the simplest
History
Acrolein was first named and characterized as an aldehyde by the Swedish chemist Jöns Jacob Berzelius in 1839. He had been working with it as a thermal degradation product of glycerol, a material used in the manufacture of soap. The name is a contraction of 'acrid' (referring to its pungent smell) and 'oleum' (referring to its oil-like consistency). In the 20th century, acrolein became an important intermediate for the industrial production of acrylic acid and acrylic plastics.[4]
Production
Acrolein is prepared industrially by oxidation of
- CH3CH=CH2 + O2 → CH2=CHCHO + H2O
About 500,000 tons of acrolein are produced in this way annually in North America, Europe, and Japan. Additionally, all acrylic acid is produced via the transient formation of acrolein.
Propane represents a promising but challenging feedstock for the synthesis of acrolein (and acrylic acid).The main challenge is in fact the overoxidation to this acid.
When glycerol (also called glycerin) is heated to 280 °C, it decomposes into acrolein:
- (CH2OH)2CHOH → CH2=CHCHO + 2 H2O
This route is attractive when glycerol is co-generated in the production of biodiesel from vegetable oils or animal fats. The dehydration of glycerol has been demonstrated but has not proven competitive with the route from petrochemicals.[6][7]
Niche or laboratory methods
The original industrial route to acrolein, developed by Degussa, involves condensation of formaldehyde and acetaldehyde:
- HCHO + CH3CHO → CH2=CHCHO + H2O
Acrolein may also be produced on lab scale by the action of potassium bisulfate on glycerol (glycerine).[8]
Reactions
Acrolein is a relatively
Uses
Military uses
Acrolein was used in warfare due to its irritant and blistering properties. The French used the chemical in their hand grenades and artillery shells[9] during World War I under the name "Papite".[10]
Biocide
Acrolein is mainly used as a contact herbicide to control submersed and floating weeds, as well as algae, in irrigation canals. It is used at a level of 10 ppm in irrigation and recirculating waters. In the oil and gas industry, it is used as a biocide in drilling waters, as well as a scavenger for hydrogen sulfide and mercaptans.[5]
Chemical precursor
A number of useful compounds are made from acrolein, exploiting its bifunctionality. The amino acid
.Acrolein will polymerize in the presence of oxygen and in water at concentrations above 22%. The color and texture of the polymer depends on the conditions. The polymer is a clear, yellow solid. In water, it will form a hard, porous plastic.[citation needed]
Acrolein has been used as a fixative in preparation of biological specimens for
Health risks
Acrolein is toxic and is a strong irritant for the skin, eyes, and nasal passages.[5] The main metabolic pathway for acrolein is the alkylation of glutathione. The WHO suggests a "tolerable oral acrolein intake" of 7.5 μg per day per kg of body weight. Although acrolein occurs in French fries (and other fried foods), the levels are only a few μg per kg.[13] In response to occupational exposures to acrolein, the US Occupational Safety and Health Administration has set a permissible exposure limit at 0.1 ppm (0.25 mg/m3) at an eight-hour time-weighted average.[14] Acrolein acts in an immunosuppressive manner and may promote regulatory cells,[15] thereby preventing the generation of allergies on the one hand, but also increasing the risk of cancer.
Acrolein was identified as one of the chemicals involved in the 2019 Kim Kim River toxic pollution incident.[16]
Cigarette smoke
Connections exist between acrolein gas in the smoke from tobacco cigarettes and the risk of lung cancer.[17] Acrolein is one of seven toxicants in cigarette smoke that are most associated with respiratory tract carcinogenesis.[18] The mechanism of action of acrolein appears to involve induction of increased reactive oxygen species and DNA damage related to oxidative stress.[19]
In terms of the "noncarcinogenic health quotient"[
Chemotherapy metabolite
Cyclophosphamide and ifosfamide treatment results in the production of acrolein.[27] Acrolein produced during cyclophosphamide treatment collects in the urinary bladder and if untreated can cause hemorrhagic cystitis.
Endogenous production
Acrolein is a component of reuterin.[28] Reuterin can be produced by gut microbes when glycerol is present. Microbe-produced reuterin is a potential resource of acrolein.[29]
Analytical methods
The "acrolein test" is for the presence of
4), the glycerol portion of the molecule is dehydrated to form the unsaturated aldehyde, acrolein (CH2=CH–CHO), which has the odor peculiar to burnt cooking grease. More modern methods exist.[13]
In the US, EPA methods 603 and 624.1 are designed to measure acrolein in industrial and municipal wastewater streams.[30][31]
References
- ^ a b c d e f g h i NIOSH Pocket Guide to Chemical Hazards. "#0011". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "Acrolein". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ "Archived copy". Archived from the original on 2015-04-02. Retrieved 2015-03-26.
{{cite web}}
: CS1 maint: archived copy as title (link) - ^ Jan F. Stevens and Claudia S. Maier, "Acrolein: Sources, metabolism, and biomolecular interactions relevant to human health and disease", Mol Nutr Food Res. 2008 Jan; 52(1): 7–25.
- ^ ISBN 978-3527306732.
- .
- S2CID 246853148.
- ; Collected Volumes, vol. 1, p. 15.
- ^ Prentiss, Augustin Mitchell; Fisher, George J. B. (1937). Chemicals in War: A Treatise on Chemical Warfare. McGraw-Hill Book Company, Incorporated. p. 139. Retrieved 21 November 2021.
- ^ Eisler, Ronald (1994). Acrolein Hazards to Fish, Wildlife, and Invertebrates: A Synoptic Review. U.S. Department of the Interior, National Biological Survey. Retrieved 21 November 2021.
- ISBN 978-3527306732.
- ISBN 0-306-47749-1.
- ^ PMID 21898908.
- ^ CDC - NIOSH Pocket Guide to Chemical Hazards
- PMID 28332605.
- ^ Tara Thiagarajan (Mar 15, 2019). "8 Chemicals Have Been Identified in Pasir Gudang's Kim Kim River, Here's What They Are". World of Buzz.
- PMID 17030796.
- PMID 21802474
- PMID 18404534
- PMID 22352345.
- PMID 20161525.
- PMID 26422308.
- PMID 26726281.
- S2CID 26116099.
- ^ McNeill, A, SC (2015). "E - cigarettes: an evidence update A report commissioned by Public Health England" (PDF). www.gov.uk. UK: Public Health England. pp. 76–78. Retrieved 20 August 2015.
{{cite web}}
: CS1 maint: multiple names: authors list (link) - S2CID 31872198.
- PMID 10755368.
- PMID 27819285.
- PMID 29339426.
- ^ Appendix A To Part 136 Methods For Organic Chemical Analysis of Municipal and Industrial Wastewater, Method 603—Acrolein And Acrylonitrile>
- ^ Method 624.1 — Purgables by GC-MS>