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에틸렌다이아민테트라아세트산

에틸렌다이아민테트라아세트산
에틸렌다이아민테트라아세트산 구조식 이미지
카스 번호:
60-00-4
한글명:
에틸렌다이아민테트라아세트산
동의어(한글):
(에틸렌디니트릴로)사아세트산;베르센산;에데틱산;N,N$$@@-1,2-에탄디일비스(N-(카르복시메틸)글리신(N,N$$@@-1,2-ETHANEDIYLBIS;베르세닉산;에틸렌다이아민테트라아세트산;에틸렌디아민테트라초산;이디티에이;이디티에이산
상품명:
Ethylenediaminetetraacetic acid
동의어(영문):
yd30;EDTA;EdtaAr;EdtaGr;celona;Edetic;seq100;Trilon;VERSENE;Celon A
CBNumber:
CB9853940
분자식:
C10H16N2O8
포뮬러 무게:
292.24
MOL 파일:
60-00-4.mol

에틸렌다이아민테트라아세트산 속성

녹는점
250 °C (dec.)(lit.)
끓는 점
434.18°C (rough estimate)
밀도
0,86 g/cm3
증기압
<0.013 hPa (20 °C)
굴절률
n20/D 1.363
인화점
>400°C DIN 51758
저장 조건
2-8°C
용해도
3  M NaOH: 100 mg/mL
물리적 상태
crystalline
산도 계수 (pKa)
pKa 2 (Uncertain);10.26 (Uncertain)
색상
White to almost white
수소이온지수(pH)
2.5 (10g/l, H2O, 23℃)(slurry)
수용성
0.5 g/L (25 ºC)
최대 파장(λmax)
λ: 280 nm Amax: ≤0.25
Merck
14,3517
BRN
1716295
안정성
Stable. Incompatible with copper, copper alloys, nickel, aluminium, strong oxidizing agents, strong bases
CAS 데이터베이스
60-00-4(CAS DataBase Reference)
NIST
N,N'-1,2-Ethane diylbis-(N-(carboxymethyl)glycine)(60-00-4)
EPA
Glycine, N,N'-1,2-ethanediylbis[ N-(carboxymethyl)-(60-00-4)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xi
위험 카페고리 넘버 36-52/53-36/37/38-36/38
안전지침서 26-61-37/39-36
유엔번호(UN No.) UN 3077 9 / PGIII
WGK 독일 2
RTECS 번호 AH4025000
F 고인화성물질 3
자연 발화 온도 >200 °C
TSCA Yes
HS 번호 2922 49 85
유해 물질 데이터 60-00-4(Hazardous Substances Data)
독성 LD50 orally in Rabbit: 2580 mg/kg
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
예방조치문구:
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P337+P313 눈에 대한 자극이 지속되면 의학적인 조치· 조언를 구하시오.

에틸렌다이아민테트라아세트산 C화학적 특성, 용도, 생산

물성

냉수, 알코올 및 일반 유기 용제에는 녹지 않으며 뜨거운 물에는 약간 용해되지만 수산화 나트륨, 탄산나트륨 및 암모니아 용액에는 용해되는 백색 결정 분말 융점 240℃(분해).

개요

EDTA는 칼슘과 같은 다양한 다가 양이온을 격리하는 킬레이트 제입니다. 그것은 제약 제조 및 식품 첨가제로 사용됩니다.주로 금속 이온 complexing 및 금속 분리에 적용; 수처리제 및 탈지제로 사용되는 첨가제; 물에서 금속 이온으로 인한 생산에 대한 유해한 영향을 방지 할 수있는 것; 사진, 제지 및 오일 필드 용 화학 물질. 화학 분석에서 보더 샌드 시약을 청소할 때도 사용됩니다.

용도

EDTA는 욕조세제의 첨가물이기도 한데, 이는 EDTA가 비누의 음이온 성분과 반응하여 욕조에 끼는 때의 주성분인 침전을 형성하는 Ca2+이온과 반응하기 때문에 침전의 용해도를 증가시켜 때가 씻겨질 수 있게 하기 때문이다. EDTA는 물 속에 들어있는 금속 이온을 제거하는 데도 이용된다. EDTA는 Pb2+이온과 강한 친화성을 가지기 때문에 납중독의 치료제로도 사용되어 왔다. EDTA와 철 이온의 착물은 식물에 철 성분을 공급하는 데 이용되기도 한다. EDTA로 식용유에 존재하는 산화반응의 촉매인 금속 이온을 제거하여 식용유가 썩는 것을 방지할 수 있다. 생화학이나 분자생물학에서는 DNA나 단백질에 관련된 실험을 할 때, 시료가 효소로 인하여 손상되는 것을 막기 위해 효소가 필요로 하는 금속 이온을 제거할 목적으로 EDTA를 사용한다. EDTA는 혈액의 응고방지제로도 이용된다. 분석화학에서는 EDTA를 주로 금속 이온의 분석, 분리, 제거 등에 활용한다. EDTA는 완충용액의 성분으로 사용될 수 있다.

개요

Ethylenediaminetetraacetic Acid (EDTA) is a common polydentate ligand. In EDTA, the hydrogen atoms are easily removed in solution to produce anionic EDTA4-. In its anionic form Ethylenediaminetetraacetic Acid (EDTA) has six binding atoms, two nitrogen and four oxygen.
Ethylenediaminetetraacetic Acid (EDTA) binds to a metal ion at the six binding sites, wrapping itself around the metal ion, forming a very stable complex.the strong grasp of Ethylenediaminetetraacetic Acid (EDTA) on the metal ion is analogous to a crab or lobster clamping down on an object with its claw, hence the name chelation. Ethylenediaminetetraacetic Acid (EDTA) is such an effective chelating agent because it can deactivate a metal at up to six sites.

화학적 성질

Edetic acid occurs as a white crystalline powder.

화학적 성질

white crystals or powder

화학적 성질

EDTA is a white, odorless, crystalline material or white powder

역사

Ethylenediaminetetraacetic Acid (EDTA) was first synthesized in the early 1930s by the German chemist Ferdinand Münz working for I. G. Farben. Münz, who was looking for a substitute for citric acid to use with dye solutions in the textile industry, was the first to patent a process for Ethylenediaminetetraacetic Acid (EDTA) synthesis in Germany in 1935. Münz subsequently applied for United States patents in 1936 and 1937 (U.S. Patent Number 2130505); his method involved reacting monochloroacetic acid (C2H3ClO2) and ethylene diamine (C2H8N2). Concurrent with Münz’s work, Frederick C. Bersworth in the United States synthesized Ethylenediaminetetraacetic Acid (EDTA) using different methods that gave greater yields and made EDTA’s commercial production economically viable. Bersworth syntheses involved reacting formaldehyde, amines, and hydrogen cyanide. Bersworth and Münz obtained patents for Ethylenediaminetetraacetic Acid (EDTA) production in the 1940s (U.S. Patent Numbers 2407645 and 2461519).

용도

EDTA, also known as editic acid, is a colorless crystalline substance widely used to chelate metal ions.
Ethylenediaminetetraacetic Acid (EDTA) is marketed in its salt forms such as sodium Ethylenediaminetetraacetic Acid (EDTA) or calcium EDTA. Ethylenediaminetetraacetic Acid (EDTA) hasindustrial and medical uses as a chelating agent. Much of its utility is related to the fact that metals and metal compounds are important catalysts in numerous reactions. By chelatingmetals, Ethylenediaminetetraacetic Acid (EDTA) prevents the metal from catalyzing reactions, thereby limiting degradation, oxidation,and other undesirable reactions.the major industries using Ethylenediaminetetraacetic Acid (EDTA) and other chelatingagents are paper and pulp, cleaning products, chemicals, agriculture, and water treatment.The paper and pulp industry is the major user of EDTA, where it is used to stabilize bleachesby sequestering metals that catalyze the degradation of bleaches. EDTA’s ability to stabilizebleaches also makes them useful in laundry detergents and various other cleaning products.In addition to improving bleaching effi ciency, Ethylenediaminetetraacetic Acid (EDTA) use in detergents and cleansers alsosoftens hard water by tying up divalent metal ions responsible for water hardness, primarilyCa2+ and Mg2+. Its softening ability helps Ethylenediaminetetraacetic Acid (EDTA) reduce scale formation and improves foamingproperties in cleaning formulations. Ethylenediaminetetraacetic Acid (EDTA) is applied in general water treatment to softenwater, helping to prevent scale and corrosion. Ethylenediaminetetraacetic Acid (EDTA) has low toxicity and is used in the foodand beverage industry. Foods naturally contain small traces of metals and small quantities areadded during food processing. Ethylenediaminetetraacetic Acid (EDTA) is used with foods to preserve color and preserve flavor,prevent odors, maintain nutrient content, and extend shelf life. When used in beverages,Ethylenediaminetetraacetic Acid (EDTA) preserves color and stabilizes other ingredients such as citric acid and benzoates. In thechemical industry, Ethylenediaminetetraacetic Acid (EDTA) is used to control metal catalytic processes during reactions. EDTAsalts are used in agriculture to provide metal micronutrients in fertilizers.

용도

EDTA is helps boost a formulation’s preservative system and is also a chelating agent.

용도

Ethylenediaminetetraacetate (EDTA) is a sequestrant and chelating agent that functions in water but not in fats and oils. It is used to control the reaction of trace metals with some organic and inorganic components to prevent deterioration of color, texture, and development of precipitates, as well as to prevent oxidation which results in rancidity. The reactive sites of the metal ions are blocked, which prevents their normal reactions. The most common interfering metal ions in food products are iron and copper. It can be used in combination with the antioxidants bht and propyl gallate. It is used in margarine, mayonnaise, and spreads to prevent the vegetable oil from going rancid. It is used in canned corn prior to retorting to prevent discoloration caused by trace quantities of copper, iron, and chromium. It also inhibits copper-catalyzed oxidation of ascorbic acid. It occurs as disodium calcium and disodium dihydrogen . Its use is approved in specified foods, with an average usage level being in the range of 100–300 ppm.

용도

antispasmodic

용도

Ethylenediamine-N,N,N’N’tetraacetic Acid (EDTA) is a powerful chelating agent; EDTA forms stable complexes with most metal ions. EDTA is used in treatment of lead and heavy metal poisoning of farm a nimals.

정의

An organic chelating agent.

정의

A compound with the formula (HOOCCH2)2N(CH2)2N(CH2COOH)2 It is used in forming chelates of transition metals.

생산 방법

Edetic acid may be prepared by the condensation of ethylenediamine with sodium monochloroacetate in the presence of sodium carbonate. An aqueous solution of the reactants is heated to about 90°C for 10 hours, then cooled, and hydrochloric acid is added to precipitate the edetic acid.
Edetic acid may also be prepared by the reaction of ethylenediamine with hydrogen cyanide and formaldehyde with subsequent hydrolysis of the tetranitrile, or under alkaline conditions with continuous extraction of ammonia.

상표명

Versene Acid (Dow Chemical).

일반 설명

Ethylenediamine tetraacetic acid is a colorless crystalline solid. Ethylenediaminetetraacetic acid is slightly soluble in water. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Ethylenediaminetetraacetic acid is used in chemical analysis, to make detergents and cleaning compounds, and for many other uses.

공기와 물의 반응

Slightly soluble in water.

반응 프로필

Behaves as a weak organic 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 Ethylenediaminetetraacetic acid 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

농업용

EDTA is short for ethylenediamhetetraacetic acid, an amino polycarboxylic acid. It is a tetraprotic acid and is represented as H4Y with four carboxyl groups and two nitrogen atoms acting as ligand sites. Thus the compound is a hexadentate ligand. Ligands include ions such as Cl-, NO2-and CN- or neutral molecules like NH3 and H2O, which possess a lone pair of electrons that can be shared with a metal cation in coordinate covalent bonds.
The water solubility of EDTA is very low and, therefore, its di-sodium salt Na2H2Y.2H2O is commonly used in titrations. The Y4- forms very stable, one-to-one complexes with practically every metal ion in the Periodic Table. The reactions are carried out in a neutral or alkaline medium as the complex decomposes in acidic medium.
(and hence deterioration) of the food product, (d) to increase the storage life of whole blood by removing free calcium ions (Ca2+) to inhibit clotting, and (e) for extracting trace elements, especially copper. EDTA metal complexes, such as NaFeEDTA, MnEDTA, ZnEDTA and CuEDTA are used as fertilizers and foliar sprays.

Pharmaceutical Applications

Edetic acid and edetate salts are used in pharmaceutical formulations, cosmetics, and foods as chelating agents. They form stable water-soluble complexes (chelates) with alkaline earth and heavy metal ions. The chelated form has few of the properties of the free ion, and for this reason chelating agents are often described as ‘removing’ ions from solution; this process is also called sequestering. The stability of the metal–edetate complex depends on the metal ion involved and also on the pH. The calcium chelate is relatively weak and will preferentially chelate heavy metals, such as iron, copper, and lead, with the release of calcium ions. For this reason, edetate calcium disodium is used therapeutically in cases of lead poisoning.
Edetic acid and edetates are primarily used as antioxidant synergists, sequestering trace amounts of metal ions, particularly copper, iron, and manganese, that might otherwise catalyze autoxidation reactions. Edetic acid and edetates may be used alone or in combination with true antioxidants, the usual concentration employed being in the range 0.005–0.1% w/v. Edetates have been used to stabilize ascorbic acid; corticosteroids; epinephrine; folic acid; formaldehyde; gums and resins; hyaluronidase; hydrogen peroxide; oxytetracycline; penicillin; salicylic acid, and unsaturated fatty acids. Essential oils may be washed with a 2% w/v solution of edetate to remove trace metal impurities.
Edetic acid and edetates possess some antimicrobial activity but are most frequently used in combination with other antimicrobial preservatives owing to their synergistic effects. Many solutions used for the cleaning, storage, and wetting of contact lenses contain disodium edetate. Typically, edetic acid and edetates are used in concentrations of 0.01–0.1% w/v as antimicrobial preservative synergists.
Edetic acid and disodium edetate may also be used as water softeners since they will chelate the calcium and magnesium ions present in hard water; edetate calcium disodium is not effective. Many cosmetic and toiletry products, e.g. soaps, contain edetic acid as a water softener.

생물학적 활성

Chelating agent; sequesters di- and trivalent metal ions.

Safety Profile

Poison by intraperitoneal route. Experimental teratogenic and reproductive effects. Mutation data reported. A general-purpose chelaung and complexing agent. When heated to decomposition it emits toxic fumes of NOx.

Safety

Edetic acid and edetates are widely used in topical, oral, and parenteral pharmaceutical formulations. They are also extensively used in cosmetics and food products.
Edetic acid is generally regarded as an essentially nontoxic and nonirritant material, although it has been associated with doserelated bronchoconstriction when used as a preservative in nebulizer solutions. It has therefore been recommended that nebulizer solutions for bronchodilation should not contain edetic acid.
Edetates, particularly disodium edetate and edetate calcium disodium, are used in a greater number and variety of pharmaceutical formulations than the free acid.
Disodium edetate, trisodium edetate, and edetic acid readily chelate calcium and can, in large doses, cause calcium depletion (hypocalcemia) if used over an extended period or if administered too rapidly by intravenous infusion. If used in preparations for the mouth, they can also leach calcium from the teeth. In contrast, edetate calcium disodium does not chelate calcium. Edetate calcium disodium is nephrotoxic and should be used with caution in patients with renal impairment.
The WHO has set an estimated acceptable daily intake for disodium edetate in foodstuffs at up to 2.5 mg/kg body-weight.
LD50 (mouse, IP): 0.25 g/kg
LD50 (rat, IP): 0.397 g/kg

잠재적 노출

EDTA is a white, odorless, crystalline material or white powder

저장

Although edetic acid is fairly stable in the solid state, edetate salts are more stable than the free acid, which decarboxylates if heated above 150°C. Disodium edetate dihydrate loses water of crystallization when heated to 120°C. Edetate calcium disodium is slightly hygroscopic and should be protected from moisture.
Aqueous solutions of edetic acid or edetate salts may be sterilized by autoclaving, and should be stored in an alkali-free container.
Edetic acid and edetates should be stored in well-closed containers in a cool, dry place.

운송 방법

UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

Purification Methods

Dissolve EDTA in aqueous KOH or ammonium hydroxide, and precipitate it twice with dilute HCl or HNO3. Boil it twice with distilled water to remove mineral acid, then recrystallise it from water or dimethylformamide. Dry it at 110o. It also recrystallises from boiling 1N HCl; wash the crystals with distilled H2O and dry them in vacuo. [Ma & Ray Biochemistry 19 751 1980, Beilstein 4 IV 2449.]

비 호환성

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, copper, copper alloys, and nickel

비 호환성

Edetic acid and edetates are incompatible with strong oxidizing agents, strong bases, and polyvalent metal ions such as copper, nickel, and copper alloy.
Edetic acid and disodium edetate behave as weak acids, displacing carbon dioxide from carbonates and reacting with metals to form hydrogen.
Other incompatibilities include the inactivation of certain types of insulin due to the chelation of zinc, and the chelation of trace metals in total parenteral nutrition (TPN) solutions following the addition of TPN additives stabilized with disodium edetate. Calcium disodium edetate has also been reported to be incompatible with amphotericin and with hydralazine hydrochloride in infusion fluids.

Regulatory Status

Included in the FDA Inactive Ingredients Database (oral, otic, rectal, and topical preparations; submucosal injection preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

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