Polyethoxylated tallow amine = POEA

CAS Number: 61791-26-2

Polyethoxylated tallow amine (also polyoxyethyleneamine, POEA) refers to a range of non-ionic surfactants derived from animal fats (tallow).
They are used primarily as emulsifiers and wetting agents for agrochemical formulations, such as pesticides and herbicides (e.g. glyphosate).

Polyethoxylated tallowamine (POEA) is a non-ionic surfactant used in herbicide formulations to increase the efficacy of active ingredients.
POEA promotes penetration of herbicide active ingredients into plant cuticles, and in animal species is known to cause alterations in respiratory surfaces.
POEA use has increased recently with the advent of "Roundup-Ready" crops; however, Polyethoxylated tallow amines potential effects on aquatic invertebrates are relatively unknown.

The aquatic macroinvertebrate Thamnocephalus platyurus (Crustacea, Anostraca) was used to assess the acute toxicity of POEA.
Three formulations of POEA consisting of a 5:1, 10:1, and 15:1 average oxide:tallowamine were used in this study.
All POEA formulations were found to be extremely toxic to T. platyurus with 48-h LC50 concentrations as low as 2.01 microg/L for 15:1.
POEA toxicity increased as the tallowamine chain length was reduced, whereas the oxide chain length appeared to only slightly increase toxicity.
Based on these results, POEA has the potential to adversely affect aquatic organisms in areas in which it is used.

POEA (polyoxyethylene tallow amine) is a surfactant with known toxic effects on aquatic organisms.
POEA was added to the original formulation of the herbicide glyphosate to aid in its application and effectiveness at controlling weeds. U.S. Geological Survey (USGS) scientists developing methods to measure POEA in the environment have shown that it’s a complex and variable mixture of related compounds, and that POEA is still a common additive in several newer agricultural and household glyphosate formulations.
Since glyphosate is one of the most widely used pesticides in the United States, the findings could indicate that POEA may be widely available for transport into surface water and groundwater.
Such additives in pesticide formulations are commonly called "inert" ingredients or adjuvants, and little is known about these ingredients and their occurrence and transport in, and effects on, the environment.
This USGS study is the first step in investigating the environmental fate and effects of POEA in herbicide applications.

Polyethoxylated tallow amine (POEA) is a common surfactant used in glyphosate-based herbicide formulations to enhance the bioavailability of the active herbicide ingredient.
Toxic effects of POEA exposure are well documented for aquatic organisms, but despite the widespread occurrence of POEA in soils, the potential effects on soil bacteria have not been investigated.
Here we examined the growth and metabolic effects of POEA in three strains of plant-beneficial soil Pseudomonas species grown on succinate, a common root exudate.
Compared to the rate of growth on only succinate, the addition of POEA resulted in up to 60% reduction in the biomass growth rate.

In the presence of both POEA and glyphosate, the biomass growth rate either remained the same as during exposure to only POEA or decreased by only an additional 5–15%, thus indicating that growth inhibition was primarily caused by POEA.
Metabolomics analysis of POEA-exposed cells identified, relative to control cells, disruption of metabolite levels in key biosynthetic pathways: accumulation of ribonucleotides and depletion of amino acids.
Kinetic 13C flux experiments further revealed delayed de novo biosynthesis of pyrimidine ribonucleotides.
Our findings thus highlight disconnects between carbon metabolism and biomass biosynthesis as potential adverse metabolic outcomes in POEA-exposed soil-beneficial bacteria.

Polyethoxylated tallow amine (POEA) refers to a range of non-ionic surfactants derived from animal fats (tallow).
They primarily find used as emulsifiers and wetting agents for agrochemical formulations, such as pesticides and herbicides (e.g. glyphosate).

Synthesis of Polyethoxylated tallow amine:
Animal fat is hydrolysed to give a mixture of free fatty acids, typically oleic (37–43%), palmitic (24–32%), stearic (20–25%), myristic (3–6%), and linoleic (2–3%).
These are then converted to fatty amines via the nitrile process before being ethoxylated with ethylene oxide; this makes them water-soluble and amphiphilic.
The length of the fatty tail and degree of exothylation will determine the overall properties of the surfactant.
Due to Polyethoxylated tallow amine being synthesized from an impure material POEA is itself a mixture of compounds.

Composition and uses of Polyethoxylated tallow amine:
The polyethoxylated tallow amine used as a surfactant is referred to in the literature as MON 0139 or polyoxyethyleneamine (POEA).
Polyethoxylated tallow amine is contained in the herbicide Roundup.
An ethoxylated tallow amine (CAS No. 61791-26-2), is on the United States Environmental Protection Agency List 3 of Inert Ingredients of Pesticides."

Roundup Pro is a formulation of glyphosate that contains a "phosphate ester neutralized polyethoxylated tallow amine" surfactant; as of 1997 there was no published information regarding the chemical differences between the surfactant in Roundup and Roundup Pro.
POEA concentrations range from <1% in ready-to-use glyphosate formulations to 21% in concentrates.
POEA constitutes 15% of Roundup formulations and the phosphate ester neutralized polyethoxylated tallow amine surfactant constitutes 14.5% of Roundup Pro.
Surfactants are added to glyphosate to allow effective uptake of water-soluble glyphosate across plant cuticles, which are hydrophobic, and reduces the amount of glyphosate washed off plants by rain.

Polyethoxylated tallow amine (POEA) surfactants have been used in many glyphosate-based herbicide formulations for agricultural, industrial and residential weed control.
The potential for release of these compounds into the environment is of increasing concern due to their toxicity towards aquatic organisms.
Current methods for analysis of POEA surfactants require significant time and effort to achieve limits of quantification that are often higher than the concentrations at which biological effects have been observed (as low as 2 ng mL(-1)).
We have developed a rapid and robust method for quantifying the POEA surfactant mixture MON 0818 at biologically relevant concentrations in fresh water, sea water and lake sediment using reversed phase high-performance liquid chromatography and electrospray ionization-tandem mass spectrometry.
Water samples preserved by 1:1 v/v dilution with methanol are analyzed directly following centrifugation.

Sediment samples undergo accelerated solvent extraction in aqueous methanol prior to analysis.
Large volume (100 μL) sample injection and multiple reaction monitoring of a subset of the most abundant POEA homologs provide limits of quantification of 0.5 and 2.9 ng mL(-1) for MON 0818 in fresh water and sea water, respectively, and 2.5 ng g(-1) for total MON 0818 in lake sediment.
Average recoveries of 93 and 75% were achieved for samples of water and sediment, respectively spiked with known amounts of MON 0818.
Precision and accuracy for the analysis of water and sediment samples were within 10 and 16%, respectively based upon replicate analyses of calibration standards and representative samples.
Results demonstrate the utility of the method for quantifying undegraded MON 0818 in water and sediment, although a more comprehensive method may be needed to identify and determine other POEA mixtures and degradation profiles that might occur in the environment.

Definition:
Polyethoxylated tallow amine, also known as tallow fatty amine oxethylate or tallow amine (the basis is beef tallow), is a non-ionic surfactant and a mixture of acylated amine ethoxylate polymers of different lengths.
Polyethoxylated tallow amine belongs to the fatty amines.
Polyethoxylated tallow amine is easily soluble in ethanol and water.
Among others, the substance is used in different compounds in cosmetic products.
Furthermore Polyethoxylated tallow amine is used in herbicides.

There are considerable reservations against the use of tallow fatty amine ethoxethylates.
Among others, they destroy the cell membranes of the gills of aquatic organisms.
In combination with glyphosate and aminomethylphosphonic acid (AMPA) there are synergistic toxic effects on plant and animal cells.

POEA concentrations range from <1% in ready-to-use glyphosate formulations to 21% in concentrates.
POEA constitutes 15% of Roundup formulations and the phosphate ester neutralized polyethoxylated tallow amine surfactant constitutes 14.5% of Roundup Pro.
Surfactants are added to glyphosate to allow effective uptake of water-soluble glyphosate across plant cuticles, which are hydrophobic, and reduces the amount of glyphosate washed off of plants by rain.

What is tallow amine ethoxylate?
Tallow amines are derived from animal fats based fatty acids via the nitrile process.
The main source of tallow amine is from animal fats, but vegetable based tallow is also available and both can be ethoxylated to give non-ionic surfactants having similar properties. …

Is polyethoxylated tallow amine toxic?
Polyethoxylated tallowamine (POEA) is a non-ionic surfactant used in herbicide formulations to increase the efficacy of active ingredients.
All POEA formulations were found to be extremely toxic to T. platyurus with 48-h LC50 concentrations as low as 2.01 microg/L for 15:1.

What is tallow amine used for?
Uses of Polyethoxylated tallow amine: Tallow Amine is widely used in mineral floating agent, waterproof softener of fiber, dyeing assistant, anti-static agent, pigment dispersant, anti-rusting agent, anti-caking agent of fertilizer, additives of lubricating oil, germicide, etc.

What is POEA roundup?
Category: Environment and Wildlife. POEA is an acronym which stands for polyoxyethylene amine.
Polyethoxylated tallow amine is a surfactant mixture that is included in some glyphosate-based herbicides to enhance uptake of the active ingredient (glyphosate) across the waxy layers and membranes of plants.

Is tallow a surfactant?
POEA (polyoxyethylene tallow amine) is a surfactant with known toxic effects on aquatic organisms.

What is tallow alkyl?
Tallow based alkyl amines are used for synthesizing of organic chemicals & cationic and amphoteric surfactants.
Widely used in producing synthetic surfactants.
Tallow amines easily dissolve in alcohols, chloroform, benzene, & ethers.
However Polyethoxylated tallow amine does not dissolve in water.

What is the surfactant in Roundup?
POEA (polyoxyethylene tallow amine) is a surfactant with known toxic effects on aquatic organisms.
POEA was added to the original formulation of the herbicide glyphosate to aid in its application and effectiveness at controlling weeds.

How do you make a tallow amine?
First, ammonia is reacted with animal fat extracts (tallow) to produce a tallow amine.
Then, the tallow amine is ethoxylated to form a polyoxyethylene tallow amine.
This representation of the different chemicals used to synthetize one molecule of polyoxyethylene (15) tallow amine is a simplification.

What is hydrogenated tallow amine?
Hydrogenated Tallow Amine.
Odor of Polyethoxylated tallow amine: characteristic.
Uses of Polyethoxylated tallow amine: Tallow Amines are used for soaps, leather dressings, candles, food, and lubricants.
They are used in producing synthetic surfactants.
Tallow based alkyl amines are widely used in the synthesis of organic chemicals and cationic and amphoteric surfactants.

Environmental effects of Polyethoxylated tallow amine:
The chemical complexity of POEA makes it difficult to study in the environment.

POEA is toxic to aquatic species like fish and amphibians.
Like other surfactants, Polyethoxylated tallow amine can affect membrane transport and can often act as a general narcotic.

In laboratory experiments POEA has a half-life in soils of less than 7 days.
Washout from soil is assumed to be minimal, and the estimated half-life in bodies of water would be about 2 weeks.
Field experiments have shown that the half-life of POEA in shallow waters is about 13 hours, "further supporting the concept that any potential direct effects of formulated products on organisms in natural waters are likely to occur very shortly post-treatment rather than as a result of chronic or delayed toxicity."

A review of the literature provided to the EPA in 1997 found that POEA was generally more potent in causing toxicity to aquatic organisms than glyphosate, and that POEA becomes more potent in more alkaline environments.
(Potency is measured by the median lethal dose (LD50); a low LD50 means that just a little of the substance is lethal; a high LD50 means that it takes a high dose to kill.) Glyphosate has an LD50 ranging from 4.2 times that of POEA for midge larvae at pH 6.5, to 369 times that of POEA for rainbow trout at pH 9.5 (for comparison, at pH 6.5 the LC50 of glyphosate was 70 times that of POEA for rainbow trout).
The pH value of most freshwater streams and lakes is between 6.0 and 9.0; fish species are harmed by water having a pH value outside of this range.

The formulation of glyphosate composed of Isopropylamine salt and Polyethoxylated tallow Amine (Clearweed) is widely used as herbicide to control weeds both in the terrestrial and aquatic environments.
A static bioassay was conducted to examine toxicity of this formulation on juvenile African catfish (Clarias gariepinus).
Catfish juvenile (mean weight 27.97±0.03g) were exposed to glyphosate at concentrations of 0.00mg/l (control), 5.00, 7.50, 10.00, 12.50 and 15.00mg/l.
Each concentration was treated in triplicate and the exposure period lasted for 96 hrs.

Mortality rates and physico-chemical parameters of water were monitored.
Results revealed that fish mortality increased with increasing concentration of glyphosate and time of exposure.
The median lethal concentration (96-hr LC50) value was 8.88mg/l with the upper and lower limits of 9.10mg/l and 7.75mg/l respectively.
Behavioural changes observed the treated fish included: erratic swimming, jerky movement, increased opercula and tail movements, gulping of air, lost of balance and consciousness, cessation of opercula and tail movement signifying eventual death.

Water quality parameters increased significantly (p<0.05) with extract concentration except dissolve oxygen levels which reduced (p<0.05).
However, all values reported were within the permissible limits of the Federal Ministry of Environment (FMEnv) for water samples.
The results of this study indicated that glyphosate formulation has toxic effects on catfish.
Thus, the herbicide should be cautiously used to avoid ecotoxicological hazards particularly on non-target organisms.

Little is known about the occurrence, fate, and effects of the ancillary additives in pesticide formulations.
Polyoxyethylene tallow amine (POEA) is a non-ionic surfactant used in many glyphosate formulations, a widely applied herbicide both in agricultural and urban environments.
POEA has not been previously well characterized, but has been shown to be toxic to various aquatic organisms.

Characterization of technical mixtures using ultra-high performance liquid chromatography (UHPLC) and mass spectrometry shows POEA is a complex combination of homologs of different aliphatic moieties and ranges of ethoxylate units.
Tandem mass spectrometry experiments indicate that POEA homologs generate no product ions readily suitable for quantitative analysis due to poor sensitivity.
A comparison of multiple high performance liquid chromatography (HPLC) and UHPLC analytical columns indicates that the stationary phase is more important in column selection than other parameters for the separation of POEA.
Analysis of several agricultural and household glyphosate formulations confirms that POEA is a common ingredient but ethoxylate distributions among formulations vary.

Human toxicity of Polyethoxylated tallow amine:
A review published in 2000 examining the toxicity of POEA and other components in glyphosate formulations found "no convincing evidence for direct DNA damage in vitro or in vivo, and it was concluded that Roundup and its components do not pose a risk for the production of heritable/somatic mutations in humans.
Glyphosate, AMPA, and POEA were not teratogenic or developmentally toxic.
Likewise there were no adverse effects in reproductive tissues from animals treated with glyphosate, AMPA, or POEA in chronic and/or subchronic studies."

Another review, published in 2004, said that with respect to glyphosate formulations, "experimental studies suggest that the toxicity of the surfactant, polyoxyethyleneamine (POEA), is greater than the toxicity of glyphosate alone and commercial formulations alone.
There is insufficient evidence to conclude that glyphosate preparations containing POEA are more toxic than those containing alternative surfactants.
Although surfactants probably contribute to the acute toxicity of glyphosate formulations, the weight of evidence is against surfactants potentiating the toxicity of glyphosate."

Synonym(s):
POEA
Polyethoxylated tallow amines
Talgamine
Tallow amine
Tallow Fatty Amine Oxethylate