ニトリロ三酢酸

Other Uses -> Chelating Agents

Carcinogens

greater than 1 at 68 °F (USCG, 1999)

GREATER THAN 1 AT 20 °C /SOLID/

Prismatic crystals from hot water

White crystalline powder

less than 0.1 mg/mL at 73 °F (NTP, 1992)

Slightly soluble in DMSO-d6; soluble in ethanol

1.28 g dissolves in 1 L water at 22.5 °C

Insoluble in most org solvents

In water, 5.91X10+4 mg/L at 25 °C

Solubility in water, g/100ml at 22 °C: 0.128 (poor)

When heated to decomposition it emits toxic fumes of /nitrogen oxides/.

242 °C

475 °F (decomposes) (NTP, 1992)

242 °C dec

This chemical does not meet GHS hazard criteria for 11.6% (58 of 500) of reports.

Warning

H302 (22.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 500 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Chemical: Glycine, N,N-bis(carboxymethyl)-

Hazard Traits - Carcinogenicity

Glycine, N,N-bis(carboxymethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Glycine, N,N-bis(carboxymethyl)- 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: 20-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/12171

Restricted substance: Potassium [N,N-bis(carboxymethyl)glycinato(3-)-N,O,O',O'']cadmate(1-)

Triglycollamic acid: Does not have an individual approval but may be used under an appropriate group standard

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Combustible under specific conditions. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

A skin, eye, and respiratory tract irritant; A possible human carcinogen; [ICSC] An eye irritant; Nephrotoxic in experimental animals; No evidence of teratogenicity in rats, rabbits, or mice; Emergency treatment: Oxalic acid; Oxalic acid is an irritant that, after ingestion, may cause kidney damage, hypocalcemia, and hepatic necrosis; [HSDB] A skin and mild eye irritant; Not sensitizing to 66 volunteers (20% solution); Prolonged exposure causes tumors of the urinary tract at doses greater than those that are nephrotoxic to experimental animals; No evidence of mutagenicity or teratogenicity; [EC] Not teratogenic in mice, rats, or rabbits; Reportedly causes chromosome abnormalities in the germ cells of fruit flies and mice; [REPROTOX]

DHEW/NCI; Bioassays of Nitrilotriacetic Acid (NTA) and Nitrilotriacetic Acid, Trisodium Salt, Monohydrate for Possible Carcinogenicity (1977) Technical Rpt Series No. 6 DHEW Pub No. (NIH) 77-806

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Nitrilotriacetic Acid (139-13-9) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s119nitr.pdf]

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

In case of fire in the surroundings, use appropriate extinguishing media.

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.

Rinse mouth. Give one or two glasses of water to drink.

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.

Store in a refrigerator or in a cool, dry place.

Chelating agents, by their very nature, tend to be corrosive to metals such as copper, zinc, and iron. The alkaline salts corrode aluminum severely, and contact with these salts should be avoided. Stainless steel and most polymers or coatings that are able to withstand dilute alkali are acceptable as construction materials. Solid chelating agents should be stored in a cool, dry place to avoid caking. /Chelating agents/

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

This study used acidity, ethylenediaminetetracetic acid and nitrilotriacetic acid treatment processes to explore the removal efficiencies of heavy metals from urban and industrial sludges. The results indicate that the optimum treatment efficiencies of heavy metals extraction from sludge are related to the species of heavy metals in sludge, dosage of extractants and the reaction time. The removal efficiency of a three stage countercurrent process was higher than those of single stage processes... The cost of the acid treatment process per unit weight of heavy metal extracted was lowest in conditions of high heavy metal concentrations, but the ethylenedinitrilotetraacetic process was the cheapest with low heavy metal concentrations.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with 5% acetic acid, then transfer the dampened material to a suitable container. Use absorbent paper dampened with 5% acetic acid to pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with 5% acetic acid followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for NITRILOTRIACETIC ACID (6 total), please visit the HSDB record page.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/

For more Preventive Measures (Complete) data for NITRILOTRIACETIC ACID (10 total), please visit the HSDB record page.

MICE EXPOSED SC TO CADMIUM CHLORIDE WITH NTA SHOWED HISTOLOGICAL EVIDENCE OF LIVER NECROSIS AFTER 24 HR.

THE ADMIN OF A SINGLE IV DOSE OF LEAD ALONE (50 MG/KG) OR WITH EQUIMOLAR AMOUNTS OF CHELATING AGENTS TO PREGNANT RATS RESULTED IN APPROX A 400% INCREASE IN FETAL LEAD CONTENT WITH LEAD PENICILLAMINE (PBPEN) & LEAD NITRILOTRIACETIC ACID (PBNTA) & A 50% INCREASE WITH LEAD-EDTA BY 4 HR AFTER ADMIN AS COMPARED TO LEAD ALONE.

FOLLOWING INTUBATION OF (14)C-LABELED NTA (68.2 MG/KG) INTO LEAD & NON-LEAD-TREATED RATS, THE LEVELS OF NTA IN ALL TISSUES WERE LOWEST IN LEAD-TREATED RATS. APPARENTLY, LEAD FACILITATED THE ELIMINATION OF NTA.

The effect of single dose of NTA on the removal of radio-manganese in various organs and in plasma has been studied in rats which received single i.v. injection of 54Mn(II). The lowered value of radio-manganese in NTA treated rats as compared to control animal indicates that NTA binds rapidly and forms stable and diffusible complex resulting in the fast excretion of the injected 54Mn(II).

The possible interactions of pairs of carcinogens which act on different organ systems were studied in rats, and recurring design problems of such studies were identified and new statistical methodology tested. Fischer-344 rats were exposed through diet to the six possible pairs of four chemicals. Tested chemicals and their target organs were as follows: N-methyl-N'-nitro-N-nitrosoguanidine, stomach; N-butyl-n-(4-hydroxybutyl) nitrosamine, bladder; dipentylnitrosamine, liver; and nitrilotriacetic acid, kidney, ureter, and bladder. A 4x4 factorial design was used to study each chemical pair. Doses were 0, 20, 40, or 80 ppm N-methyl-N'-nitro-N-nitrosoguanidine, 0, 30, 60, or 120 ppm N-butyl-n-(4-hydroxybutyl) nitrosamine, 0, 50, 150, or 450 ppm dipentylnitrosamine, and 0, 200, 2000, or 20000 ppm nitrilotriacetic acid. The test period was 104 weeks. An independent interaction model was used to compute an index of additivity, which indicated interactions and their types. The endpoints considered were incidence of malignant tumor, time to death from any cause, and time to death with malignant tumor. It was determined that there was no interaction of dipentylnitrosamine with any of the other three carcinogens. Nitrilotriacetic acid in combination with N-methyl-N'-nitro-N-nitrosoguanidine or N-butyl-n-(4-hydroxybutyl) nitrosamine produced antagonism for the target sites of the latter two chemicals, while N-methyl-N'-nitro-N-nitrosoguanidine and N-butyl-n-(4-hydroxybutyl) nitrosamine did not interact with each other. No synergism was noted for any combination or target site. /It was/ concluded that antagonism can occur when these compounds are given in combination to rats, and although combined exposures can be highly carcinogenic, they do not produce more tumors than implied by independent action models.

LC50; Species: Americamysis bahia (Opossum Shrimp) age 7 days; Conditions: saltwater, static, 22.2 °C, pH 7.37-8.01, salinity 14 ppt, dissolved oxygen 5.95-6.13 mg/L; Concentration: 1480000 ug/L for 96 hr

LC50; Species: Americamysis bahia (Opossum Shrimp) age 7 days; Conditions: saltwater, static, 22.2 °C, pH 7.37-8.01, salinity 34 ppt, dissolved oxygen 5.95-6.13 mg/L; Concentration: 464000 ug/L for 96 hr

LC50; Species: Americamysis bahia (Opossum Shrimp) age 7 days; Conditions: saltwater, static, 22.2 °C, pH 7.37-8.01, salinity 24 ppt, dissolved oxygen 5.95-6.13 mg/L; Concentration: 961000 ug/L for 96 hr

LC50; Species: Daphnia magna (Water Flea) age < or = 24 hr; Conditions: freshwater, static, 20-22 °C, pH 7.6-7.7; Concentration: 950000 ug/L for 24 hr /formulation/

For more Ecotoxicity Values (Complete) data for NITRILOTRIACETIC ACID (12 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of <286(SRC), using a measured Kd value of <10 in a creek sediment containing 3.5% organic carbon(2), indicates that nitrilotriacetic acid is expected to have high to moderate mobility in soil(SRC). The pKa1 of nitrilotriacetic acid is 3.03(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of nitrilotriacetic acid from moist soil surfaces is not expected to be an important fate process(SRC) given its pKa1(3). Nitrilotriacetic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation is expected to be the dominant degradation process in soils(6-7). Reviews of biodegradation screening studies have noted that nitrilotriacetic acid is readily biodegradable under aerobic conditions, moderate temperatures and acclimation(6-7). However, degradation under anaerobic conditions or cold temperatures may be slow(6-7). In soil degradation studies in five different soils, nitrilotriacetic acid biodegraded under both aerobic and water logged (presumably anaerobic) conditions; after 7-days of incubation, degradation was 6-30% (average 22.4%) in aerobic soil and 9-34% (average 25.4%) in water logged soil with no degradation in sterilized soil(8).

AQUATIC FATE: Base on a classification scheme(1), an estimated Koc value of <286(SRC), using a measured Kd value of <10 in a creek sediment containing 3.5% organic carbon(2), indicates that nitrilotriacetic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 3.03(3) indicates nitrilotriacetic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), BCFs of <9 to 24 and 109 measured in carp (Cyprinus carpio) exposed for 28 days(5), suggest the potential for bioconcentration in aquatic organisms is low to moderate(SRC). Based upon laboratory photodegradation studies, the photolytic half-life of the Fe(III) complex of nitrilotriacetic acid in the top layer of a water body was calculated to be 42.9 min at a solar spectrum at 60 deg N latitude under max sunlight intensity(6); actual photolysis rates in the environment are expected to be much slower due to various retardation factors(6). Nitrilotriacetic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(7). Nitrilotriacetic acid can be expected to biodegrade in aquatic ecosystems(8). Under optimal conditions (moderate ambient temperatures, low loading concentrations, aerobic systems), it will biodegrade readily(8). Under anaerobic conditions, biodegradation may be very slow(8). Several river die-away studies have measured half-lives ranging from 0.34 to 15 days(9-13). Nitrilotriacetic acid was rapidly biodegraded in stream water (100% in 10 days) but poorly degraded in an estuarine water(14); the degradation was inversely proportional to salinity(14).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nitrilotriacetic acid, which has an estimated vapor pressure of 7X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase nitrilotriacetic acid may be removed from the air by wet or dry deposition(SRC). Nitrilotriacetic acid does not contain chromophores that absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

/PLANTS/ In growth chamber experiments we studied the effect of nitrilotriacetate (NTA) on Cu uptake by tobacco (Nicotiana tabacum L.). Plants were exposed for 6 days to 126 uM Cu and 500 uM NTA in nutrient solutions without and with 10 g/L montmorillonite. Approximately seven times less Cu was dissolved in the montmorillonite solutions than in the nutrient solutions alone. In the absence of NTA, montmorillonite effectively competed with plant roots for Cu, although Cu remained bound to the roots. Nitrilotriacetate increased Cu uptake and translocation into shoots of tobacco by a factor of 3.5 from the nutrient solution and by a factor of 26 from the montmorillonite nutrient solution. Neither growth reduction nor any other visible sign of Cu toxicity was found in the presence of NTA with Cu concentrations of 190 mg/kg in the shoots. In the absence of NTA, high Cu concentrations in root samples led to a brownish discoloration of the roots.

/PLANTS/ In a pot experiment the effects of nitrilotriacetate (NTA) and citric acid applications on Cd extractibility from soil as well as on its uptake and accumulation by Indian mustard (Brassica juncea) were investigated. Plants were grown in a sandy soil with added CdS at four levels ranging from 50 to 200 mg Cd/kg soil. After 30 days of growth, pots were amended with NTA or citric acid at 10 and 20 mmol/kg. Control pots were not treated with chelates. Harvest of plants was performed immediately before and one week after chelate addition. Soil water-, NH(4)NO(3)- and EDTA-extractable Cd fractions increased constantly with both increasing soil metal application and chelate concentration. Shoot dry weights did not suffer significant reductions with increasing Cd addition to the soil except for both NTA treatments in which at 200 mg Cd/kg a 30% decrease in dry matter was observed. Generally, following NTA and citric acid amendments, Cd concentration in shoots increased with soil Cd level. However, due to Cd toxicity, at the highest metal application rate both NTA treatments lowered Cd concentration in the above-ground parts. Compared to the control, at 10 mmol/kg citric acid did not change Cd concentration in shoots, whereas NTA-treated plants showed an about 2-fold increase. The addition of chelates at 20 mmol/kg further enhanced Cd concentration in shoots up to 718 and 560 ug/g dry weight in the NTA and citrate treatments, respectively.

Cough. Sore throat.

Redness.

Redness. Pain.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=139-13-9]

Monitoring of wastewater effluents from 4 treatment plants in the Indianapolis, IN area between 1979 and 1983 had reported nitrilotriacetic acid concentrations of 0.003-0.639 mg/L(1); concentrations between 1979-81 (before nitrilotriacetic acid use in laundry detergents was permitted) were 0.003-0.036 mg/L while concentrations between 1981-83 (after starting use) were 0.021-0.639 mg/L(1). Concentrations of nitrilotriacetic acid in 1980 at four sewage treatment plants in the Netherlands were 37-113 ug/L in influent samples and 6-21 ug/L in effluent samples(2). In a monitoring program carried out between 1971 and 1975 at 13 Canadian sewage treatment plants, mean influent concentrations during 1971-1972 were 1.09-2.14 mg/L, effluent concentrations were 0.40-1.27 mg/L(3); mean influent concentrations during 1973-1975 were 1.75-5.16 mg/L, effluent concentrations were 0.60-3.22 mg/L(3).

Environmental fate studies show NTA biodegrades in wastewater treatment plants... Studies on the environmental effects of NTA indicate that no adverse effects occur in treatment plants or receiving waters at anticipated levels. Monitoring programs have established that only low steady-state concentrations of NTA occur in natural waters as a result of NTA usage.

PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/

The Koc of nitrilotriacetic acid is estimated as <286(SRC), using a measured Kd value of <10 in a creek sediment containing 3.5% organic carbon(1). According to a classification scheme(2), this Koc suggests that nitrilotriacetic acid is expected to have high to moderate mobility in soil(SRC). Soil Rf values of 0.33-0.41 that were measured by thin-layer chromatography also suggest moderate to high soil mobility of nitrilotriacetic acid(3). Nitrilotriacetic acid had a reported Kd of 0.3 giving a half-life of 5 days(4). The pKa1 of nitrilotriacetic acid is 3.03(5), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(6).

A positive synergistic action was produced by nitrilotriacetic acid in combination with soluble chromium(VI) as potassium dichromate in the induction of gene mutations in Salmonella typhimurium and Drosophila melanogaster. The possibility that this action depended on an effect of nitrilotriacetic acid on chromium(VI) reduction by cellular proteins was demonstrated. Gene mutations were detected by the Ames plate incorporation test on strains (TA-100), (TA-92), (TA-104) and (TA-103) of Salmonella typhimurium. In both the Salmonella and Drosophila systems, the nitrilotriacetic acid synergistically increased the mutagenicity of subtoxic doses of chromium(VI) while at higher chromium(VI) dose levels a decline of mutation frequency was noted in the presence of nitrilotriacetic acid, probably as a result of toxicity. Both effects may be referred to enhanced availability of the final genotoxic agent in the presence of nitrilotriacetic acid. The interaction was particularly evident in strains (TA-100) and (TA-104) which carried mutations affecting cell wall permeability and DNA repair. In these strains, the uptake of chromium(VI) and nitrilotriacetic acid was increased and the resulting DNA damage repaired less efficiently or by error prone mechanisms. Nitrilotriacetic acid may facilitate chromate uptake by the anion carriers of the cell membrane. Other mechanisms linked to its chelating action may also be important as suggested by the significant synergistic effect on chromium(VI) mutagenicity produced by ethylenedinitrilotetraacetic acid at very low doses, which do not modify chromium(VI) reduction by Salmonella proteins in cell free conditions.

WASHED CELL SUSPENSION OF PSEUDOMONAS SP, ISOLATED FROM SEWAGE EFFLUENT, DEGRADED ALL NTA-NITROGEN TO AMMONIUM PRIOR TO TOTAL CONVERSION OF NTA TO CO2 AND WATER. SMALL AMOUNT OF NITRITE WERE ALSO FORMED. STUDY TENDED TO SUPPORT CONTENTION THAT NTA DEGRADATION PROCEEDED THROUGH AMINODIACETIC ACID AND GLYCINE ... .

In mammalian systems, NTA is not metabolized and is excreted rapidly by filtration in the kidney.

AFTER ORAL ADMIN OF 180 MG/KG OR 45 MG/KG IV TO RATS, RELATIVELY HIGH CONCN OF NTA WERE FOUND IN LUNGS, INTESTINE, & MUSCLE. PATTERN OF DISTRIBUTION DEPENDED ON ROUTE OF ADMIN. APPROX 99% OF SINGLE ORAL DOSE ELIM IN 24 HR; 96% OF THIS WAS ELIM IN URINE.

NTA-(14)C ADMIN ORALLY TO RATS. 95% WAS EXCRETED IN URINE. LESS THAN 1% ... AS CO2. ABSORPTION OF NTA FROM GI TRACT VARIED: DOG GREATER THAN RAT GREATER THAN RABBIT & MONKEY ... DEPOSITED IN SKELETON. CONCN ... INCR WITH NUMBER OF ADMIN DOSES. MOST ACTIVE AREAS FOR ACCUMULATION ... @ SITES OF VERY ACTIVE BONE FORMATION. ALTHOUGH CONCN /NTA/ DECR RAPIDLY WITH CESSATION OF INTAKE, A SMALL AMT WAS RETAINED IN BONE AFTER EACH DOSE ... .

DOGS ADMIN 10, 20, & 50 MG NITRILOTRIACETIC ACID/KG EXCRETED MATERIAL IDENTIFIED AS CHONDROITIN A SULFATE &/OR CHONDROITIN C SULFATE.

The kidney attains concentrations of NTA greater than that in the plasma in rats with steady state plasma NTA levels. The relatively high kidney concentrations of NTA can be attributed to high concentrations of NTA in small volumes of urine. NTA is not metabolized in mammals and is excreted rapidly by filtration in the kidney ... .

A capsule containing 10 mg [1 14C]NTA in gelatin was given orally in fruit juice to each of eight male volunteers who had received no drugs for two weeks before entering the study. Twelve % of the admin radioactivity was excreted in the urine & 77% in the feces as unchanged NTA within 120 h of admin. A peak in the blood concn (6.5 ng/g serum) occurred 12 h after dosing ... .

Used as a sequestering agent, eluting agent (purification of rare-earth elements), boiler feed-water additive, and chelating agent (cleaning and separation of metals); Also used in textile processing, soaps, rubber, emulsion polymerization, water treatment, and pulp and paper processing; [HSDB]

Pulp and Paper Processing [Category: Industry]

Builder in synthetic detergents

Synthesis, chelating agent, eluting agent in purification of rare-earth elements.

CHELATING AGENT IN CLEANING & SEPARATION OF METALS, TEXTILE PROCESSING, SOAPS, RUBBER, & EMULSION POLYMERIZATION

Boiler feedwater additive; water treatment; pulp and paper processing

2023: 144,245 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4231]

Alkaline Process: ... In a typical process, aqueous NaCN solution is fed into a cascade reactor system along with formaldehyde solution. Ammonia is liberated during the synthesis and need not be supplied. The reaction takes place at 80 - 100 °C. Because of the high pH (ca. 14), triscyanomethylamine N(CH2CN)3 is hydrolyzed in situ to Na3NTA. This process generates three times as much ammonia as it consumes and the ammonia concentration must be limited to suppress the production of substances with low degrees of carboxymethylation (glycine, iminodiacetic acid). This is largely achieved by continuously distilling off the ammonia with steam or air throughout the process. However, formation of byproducts (chiefly glycolic acid, hexamethylenetetramine, and the above-mentioned amino acids) cannot be completely prevented. The resulting solution is sold directly as a 40-wt% solution, or used in the production of Na3NTA.H2O in powder form, or acidified to pH 1-2 to yield the acid (H3NTA).

Acid Process: ... In the first stage, ammonia is reacted with formaldehyde to give hexamethylenetetramine, which is then reacted with hydrogen cyanide in sulfuric acid solution to yield triscyanomethylamine. The solid triscyanomethylamine is sparingly soluble in the acidic solution and is filtered off, washed, and saponified with NaOH to give Na3NTA. The resulting solution has a far lower byproduct content than the solution from the alkaline method. It is also sold as 40% product or used in the production of Na3NTA.H2O or H3NTA.

/In the Singer synthesis process/ the cyanomethylation step is separate from the hydrolysis. Hydrogen cyanide and formaldehyde react with ethylenediamine to form insoluble (ethylenedinitrilo)tetraacetonitrile (EDTN), 2,2',2'',2'''-(1,2-ethanediyldinitrilo)tetrakis(acetonitrile), in high yield (>96%). The intermediate nitrile is separated, washed, and subsequently hydrolyzed with sodium hydroxide to tetrasodium EDTA, with liberation of byproduct ammonia. Carrying out the synthesis in two stages eliminates most of the impurity-forming reactions and yields a very pure form of chelating agent. ... This two-step reaction is also particularly well-suited to synthesizing pure NTA in high yield from ammonia as the parent compound.

REACTION OF AMMONIA WITH FORMALDEHYDE AND HYDROGEN CYANIDE, FOLLOWED BY SAPONIFICATION AND ACIDIFICATION

Agriculture, Forestry, Fishing and Hunting

Glycine, N,N-bis(carboxymethyl)-: ACTIVE

Cadmate(1-), [N,N-bis[(carboxy-.kappa.O)methyl]glycinato(3-)-.kappa.N,.kappa.O]-, potassium (1:1), (T-4)-: INACTIVE

In 1971, the use of NTA was discontinued. The possibility of resumed use arose in 1980

The Consumer Product Safety Commission stated that NTA is now used in laundry detergents in two states where phosphates are banned