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아디핀산

아디핀산
아디핀산 구조식 이미지
카스 번호:
124-04-9
한글명:
아디핀산
동의어(한글):
아디프산;1,4-부탄디카르복실산;1,4-부탄디카복실산;1,6-아디프산;안티프닉산;몰텐안디프산HEXANEDIOICACID;아디핀산;아시네텐;아시플록틴;헥산이산;아디픽산;아디픽애씨드;헥센다이오익애씨드,1,6-다이하이드라자이드
상품명:
Adipic acid
동의어(영문):
adipic;Asapic;adipate;NA-9077;Adi-pure;FEMA 2011;Acinetten;ai3-03700;Inipol DS;Acifloctin
CBNumber:
CB0718158
분자식:
C6H10O4
포뮬러 무게:
146.14
MOL 파일:
124-04-9.mol

아디핀산 속성

녹는점
151-154 °C(lit.)
끓는 점
265 °C100 mm Hg(lit.)
밀도
1,36 g/cm3
증기 밀도
5 (vs air)
증기압
1 mm Hg ( 159.5 °C)
굴절률
1.4880
FEMA
2011 | ADIPIC ACID
인화점
385 °F
저장 조건
Store below +30°C.
용해도
methanol: 0.1 g/mL, clear, colorless
산도 계수 (pKa)
4.43(at 25℃)
물리적 상태
Solid
색상
White
수소이온지수(pH)
2.7 (23g/l, H2O, 25℃)
수용성
1.44 g/100 mL (15 ºC)
Merck
14,162
JECFA Number
623
BRN
1209788
안정성
Stable. Substances to be avoided include ammonia, strong oxidizing agents.
InChIKey
WNLRTRBMVRJNCN-UHFFFAOYSA-N
CAS 데이터베이스
124-04-9(CAS DataBase Reference)
NIST
Hexanedioic acid(124-04-9)
EPA
Hexanedioic acid(124-04-9)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xi
위험 카페고리 넘버 36-41
안전지침서 26-39-24/25
유엔번호(UN No.) UN 9077
WGK 독일 1
RTECS 번호 AU8400000
자연 발화 온도 788 °F
TSCA Yes
HS 번호 29171210
유해 물질 데이터 124-04-9(Hazardous Substances Data)
독성 LD50 orally in Rabbit: 5700 mg/kg LD50 dermal Rabbit > 7940 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
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
H372 장기간 또는 반복 노출되면 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴 특정 표적장기 독성 - 반복 노출 구분 1 위험 P260, P264, P270, P314, P501
H402 수생생물에 유해함 수생 환경유해성 물질 - 급성 구분 3
예방조치문구:
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P271 옥외 또는 환기가 잘 되는 곳에서만 취급하시오.
P273 환경으로 배출하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P314 불편함을 느끼면 의학적인 조치·조언을 구하시오.
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.
P405 밀봉하여 저장하시오.
P403+P233 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

아디핀산 MSDS


1,4-Butanedicarboxylic acid

아디핀산 C화학적 특성, 용도, 생산

물성

에탄올에는 쉽게 녹으며, 아세톤에 녹고 에테르에는 거의 녹지 않는다. 금속염이 많은 것은 물에 녹는다.

용도

아디 핀산은 밑창, PU 크기, 나일론 66 및 일부 용제의 기본 용액 생산에 사용할 수 있습니다. 의학에서 Adipic Acid는 산성 매체에서의 방출에 영향을주지 않고 기공 형성 제로서 사용될 수 있습니다.

용도

1) 합성 섬유 특히 66-나일론의 제조 원료로서 중요하다. 2) 알키드 수지, 폴리에스테르의 한 성분. 3) 고급 알코올과의 디에스테르는 가소제. 4) 산의 1차 표준 물질로서 알칼리 표준액의 표준 적정에 사용된다.

용도

유화제, 안정제, pH조정제, 향료고정제로 사용된다. 베이킹파우더의 산제, 치즈, 캔디, 젤리의 산미료, 알코올 음료의 향미증진제로 사용된다. 잼, 젤리의 겔 형성을 위한 pH조절제로 사용된다.

개요

Adipic acid is a white crystalline solid/crystalline granule, and its odour has not been characterised. It is stable and incompatible with ammonia and strong oxidising agents. It may form combustible dust concentrations in air. The likely routes of exposure to workers are by skin contact and inhalation at workplaces. It is used in the manufacture of nylon, plasticisers, urethanes, adhesives, and food additives.

화학적 성질

Adipic acid is a combustible, white, crystalline solid or powder. Odorless.

화학적 성질

Adipic acid occurs as a white or almost white, odorless nonhygroscopic crystalline powder. The crystal structure of adipic acid is monoclinic holohedral.

화학적 성질

Adipic acid, HOCC(CH:04COOH, is also known as hexanedioic acid and 1,4-butanedicarboxylic acid, is a colorless crystalline dicarboxylic acid. It is slightly soluble in water and has a melting point of 152°C. It is used in the manufacture of nylon and urethane rubber.

화학적 성질

Adipic acid is a white crystalline solid/granule; its odor has not been characterized. It is stable and incompatible with ammonia and strong oxidizing agents. It may form combustible dust concentrations in air. The likely routes of exposure to workers are by skin contact and inhalation at workplaces. It is used in the manufacture of nylon, plasticizers, urethanes, adhesives, and food additives.

화학적 성질

Adipic acid is the organic compound with the formula (CH2)4(COOH)2. From the industrial perspective, it is the most important dicarboxylic acid: About 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon. Adipic acid otherwise rarely occurs in nature.

화학적 성질

Adipic acid is a crystalline powder with practically no odor. It has the lowest acidity of any of the acids commonly used in foods and has excellent buffering capacity in the range of pH 2.5 to 3.0. Like succinic and fumaric acid, adipic acid is practically nonhygroscopic. Its addition to foods imparts a smooth, tart taste. In grape-flavored products, it adds a lingering supplementary flavor and gives an excellent set to food powders containing gelatin. As a result, adipic acid has found a wide number of uses as an accidulant in dry powdered food mixtures, especially in those products having delicate flavors and where addition of tang to the flavor is undesirable.
Its aqueous solutions have the lowest acidity of any of the common food acids. For concentrations from 0.5 to 2.4 g/100 mL, the pH of its solution varies less than half a unit. Hence, it can be used as a buffering agent to maintain acidities within the range of 2.5 to 3.0. This is highly desirable in certain foods, yet the pH is low enough to inhibit the browning of most fruits and other foodstuffs.

물리적 성질

Adipic acid is a straight-chain dicarboxylic acid that exists as a white crystalline compound at standard temperature and pressure. Adipic acid is one of the most important industrial chemicals and typically ranks in the top 10 in terms of volume used annually by the chemical industry.

출처

Reported found as a minor constituent in butter, and has been found in other fats as a product of oxidative rancidity. It also occurs in beet juice, pork fat, guava fruit (Psidium guajava L.), papaya (Carica papaya L.) and raspberry (Rubus idaeus L.).

용도

Adipic acid’s main use is in the production of 6,6 nylon. It is also used in resins, plasticizers, lubricants, polyurethanes, and food additives.

용도

Adipic Acid is an acidulant and flavoring agent. it is characterized as stable, nonhygroscopic, and slightly soluble, with a water solubility of 1.9 g/100 ml at 20°c. it has a ph of 2.86 at 0.6% usage level at 25°c. it is used in powdered drinks, beverages, gelatin desserts, loz- enges, and canned vegetables. it is also used as a leavening acidulant in baking powder. it can be used as a buffering agent to maintain acidities within a range of ph 2.5–3.0. it is occasionally used in edi- ble oils to prevent rancidity.

용도

progestin

용도

Adipic Acid is primarily used in the synthesis of nylon. It has been used as a reagent in the solid-state polymerization of nylon analogs.

정의

ChEBI: An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.

생산 방법

Adipic acid can be manufactured using several methods, but the traditional and main route of preparation is by the two-step oxidation of cyclohexane (C6H12). In the first step, cyclohexane is oxidized to cyclohexanone and cyclohexanol with oxygen or air. This occurs at a temperature of approximately 150°C in the presence of cobalt or manganese catalysts. The second oxidation is done with nitric acid and air using copper or vanadium catalysts. In this step, the ring structure is opened and adipic acid and nitrous oxide are formed. Other feedstocks such as benzene and phenol may be use to synthesize adipic acid. Adipic acid production used to be a large emitter of nitrous oxide, a greenhouse gas, but these have been controlled in recent years using pollution abatement technology.

생산 방법

Adipic acid is prepared by nitric acid oxidation of cyclohexanol or cyclohexanone or a mixture of the two compounds. Recently, oxidation of cyclohexene with 30% aqueous hydrogen peroxide under organic solvent- and halide-free conditions has been proposed as an environmentally friendly alternative for obtaining colorless crystalline adipic acid.

제조 방법

Adipic acid is produced from a mixture of cyclohexanol and cyclohexanone called "KA oil", the abbreviation of "ketone-alcohol oil." The KA oil is oxidized with nitric acid to give adipic acid, via a multistep pathway. Early in the reaction the cyclohexanol is converted to the ketone, releasing nitrous acid:
HOC6H11 + HNO3 → OC6H10 + HNO2 + H2O
Among its many reactions, the cyclohexanone is nitrosated, setting the stage for the scission of the C- C bond:
HNO2 + HNO3 → NO+NO3+ H2O
OC6H10 + NO+→ OC6H9-2 - NO + H+
Side products of the method include glutaric and succinic acids.
Related processes start from cyclohexanol, which is obtained from the hydrogenation of phenol.

화학 반응

Adipic acid is a dibasic acid (can be deprotonated twice). Its pKa's are 4.41 and 5.41.
With the carboxylate groups separated by four methylene groups, adipic acid is suited for intramolecular condensation reactions. Upon treatment with barium hydroxide at elevated temperatures, it undergoes ketonization to give cyclopentanone.

생명 공학 생산

Adipic acid is industrially produced by chemical synthesis. However, there are new efforts to develop an adipic acid production process using biorenewable sources. A direct biosynthesis route has not yet been reported. The possible precursors Z,Z-muconic acid and glucaric acid can be produced biotechnologically by fermentation. Z,Z-muconic acid can be made from benzoate with concentrations up to 130 mM with a yield of close to 100 % (mol/mol) by Pseudomonas putida KT2440-JD1 grown on glucose. Alternatively, it can be produced by engineered E. coli directly from glucose at up to 260 mM with a yield of 0.2 mol Z,Zmuconic acid per mole glucose .
The production of the second possible precursor, glucaric acid, by engineered E. coli growing on glucose has been reported. However, the product titers were low (e.g. 4.8 and 12 mM. To overcome the problem of low product concentrations, an alternative synthetic pathway has been suggested but not yet demonstrated .
In a hydrogenation process, Z,Z-muconic acid and glucaric acid could be converted chemically into adipic acid. Therefore, bimetallic nanoparticles or platinum on activated carbon as catalysts have been studied . In particular, nanoparticles of Ru10Pt2 anchored within pores of mesoporous silica showed high selectivity and conversion rates, greater than 0.90 mol adipic acid per mole Z,Zmuconicacid. With platinum on activated carbon, conversion rates of 0.97 mol.mol-1 of Z,Z-muconic acid into adipic acid have been shown. Another possibility would be the production of adipic acid from glucose via the a–aminoadipate pathway ]. Finally, the production of adipic acid from longchain carbon substrates has been suggested. The conversion of fatty acids into dicarboxylic acids by engineered yeast strains has been reported.

일반 설명

Adipic acid is a white crystalline solid. Adipic acid is insoluble in water. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Adipic acid is used to make plastics and foams and for other uses.

공기와 물의 반응

Dust may form explosive mixture with air [USCG, 1999]. Insoluble in water.

반응 프로필

Adipic 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 Adipic 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. Behavior in Fire: Melts and may decompose to give volatile acidic vapors of valeric acid and other substances.

건강위험

Inhalation of vapor irritates mucous membranes of the nose and lungs, causing coughing and sneezing. Contact with liquid irritates eyes and has a pronounced drying effect on the skin; may produce dermatitis.

건강위험

Exposures to adipic acid cause pain, redness of the skin and eyes, tearing or lacrimation. Adipic acid has been reported as a non-toxic chemical. Excessive concentrations of adipic acid dust are known to cause moderate eye irritation, irritation to the skin, and dermatitis.It may be harmful if swallowed or inhaled. It causes respiratory tract irritation with symptoms of coughing, sneezing, and blood-tinged mucous.

화재위험

Behavior in Fire: Melts and may decompose to give volatile acidic vapors of valeric acid and other substances. Dust may form explosive mixture with air.

Pharmaceutical Applications

Adipic acid is used as an acidifying and buffering agent in intramuscular, intravenous and vaginal formulations. It is also used in food products as a leavening, pH-controlling, or flavoring agent.
Adipic acid has been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basicand weakly acidic drugs.It has also been incorporated into the polymeric coating of hydrophilic monolithic systems to modulate the intragel pH, resulting in zero-order release of a hydrophilic drug.The disintegration at intestinal pH of the enteric polymer shellac has been reported to improve when adipic acid was used as a pore-forming agent without affecting release in the acidic media.Other controlled-release formulations have included adipic acid with the intention of obtaining a late-burst release profile.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by other routes. A severe eye irritant. Combustible when exposed to heat or flame; can react with oxidzing materials. When heated to decomposition it emits acrid smoke and fumes.

Safety

Adipic acid is used in pharmaceutical formulations and food products. The pure form of adipic acid is toxic by the IP route, and moderately toxic by other routes. It is a severe eye irritant, and may cause occupational asthma.
LD50 (mouse, IP): 0.28 g/kg
LD50 (mouse, IV): 0.68 g/kg
LD50 (mouse, oral): 1.9 g/kg
LD50 (rat, IP): 0.28 g/kg
LD50 (rat, oral): >11 g/kg

Chemical Synthesis

By oxidation of cyclohexanol with concentrated nitric acid; by catalytic oxidation of cyclohexanone with air.

잠재적 노출

Workers in manufacture of nylon, plasticizers, urethanes, adhesives, and food additives

저장

Adipic acid is normally stable but decomposes above boiling point. It should be stored in a tightly closed container in a cool, dry place, and should be kept away from heat, sparks, and open flame.

저장

Adipic acid should be kept stored in a tightly closed container, in a cool, dry, ventilated area and protected against physical damage. In storage, adipic acid should be isolated from incompatible substances and dust formation and ignition sources should be avoided.

운송 방법

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

Purification Methods

For use as a volumetric standard, adipic acid is crystallised once from hot water with the addition of a little animal charcoal, dried at 120o for 2hours, then recrystallised from acetone and again dried at 120o for 2hours. Other purification procedures include crystallisation from ethyl acetate and from acetone/petroleum ether, fusion followed by filtration and crystallisation from the melt, and preliminary distillation under vacuum. [Beilstein 2 IV 1956.]

비 호환성

Dust may form explosive mixture with air. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates, and dithionites (releasing hydrogen sulfate and oxides of sulfur). Reacts with oxidizers, reducing agents; and strong bases. Dust forms an explosive mixture with air. Frictionfrom stirring, pouring, or pneumatic transfer can form electrostatic charge on dry material. React violently with strong oxidizers, bromine, 90% hydrogen peroxide, phosphorus trichloride, silver powders or dust. Mixture with some silver compounds forms explosive salts of silver oxalate. Incompatible with silver compounds. Corrosive to some metals.

비 호환성

Adipic acid is incompatible with strong oxidizing agents as well as strong bases and reducing agents. Contact with alcohols, glycols, aldehydes, epoxides, or other polymerizing compounds can result in violent reactions.

폐기물 처리

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed

주의 사항

Occupational workers should avoid contact of the adipic acid with the eyes, avoid breathing dust, and keep the container closed. Workers should use adipic acid only with adequate ventilation. Workers should wash thoroughly after handling adipic acid and keep away from heat, sparks, and flame. Also, workers should use rubber gloves and laboratory coats, aprons, or coveralls, and avoid creating a dust cloud when handling, transferring, and cleaning up.

Regulatory Status

GRAS listed. Included in the FDA Inactive Ingredients Database (IM, IV, and vaginal preparations). Accepted for use as a food additive in Europe. Included in an oral pastille formulation available in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

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