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말레인산

말레인산
말레인산 구조식 이미지
카스 번호:
110-16-7
한글명:
말레인산
동의어(한글):
말레인산;말레산;말레익애씨드;시스-부텐이산;시스-1,2-에틸렌디카르복시산;시스-에틸렌-1,2-디카르복시산;말레인산;(z), 1,2-에틸렌다이카복실산;(Z)-2-부텐이산;(z)-부텐이산;1,2-에틸렌 다이카복실산;2-부텐이산(z);말레인 산;말렌 산;시스-1,2-에틸렌다이카복시산;시스-2-부텐이산;시스-에틸렌-1,2-다이카복시산;시스-에틸렌다이카복시산;톡실릭 산
상품명:
Maleic acid
동의어(영문):
NA 2215;eic acid;Maleicaci;malenicacid;MALEIC ACID;maleinicacid;Malenic acid;MaleicAcidGr;MaleicAcidBp;TOXILIC ACID
CBNumber:
CB2852803
분자식:
C4H4O4
포뮬러 무게:
116.07
MOL 파일:
110-16-7.mol

말레인산 속성

녹는점
130-135 °C (lit.)
끓는 점
275°C
밀도
1.59 g/mL at 25 °C (lit.)
굴절률
1.5260 (estimate)
인화점
127 °C
저장 조건
Store below +30°C.
용해도
478.8g/l
물리적 상태
Powder/Solid
산도 계수 (pKa)
1.83(at 25℃)
색상
White
Specific Gravity
1.59
수소이온지수(pH)
1.3 (100g/l, H2O, 20℃)
수용성
790 g/L (25 ºC)
Merck
14,5703
BRN
605762
안정성
Stable. Combustible. Incompatible with strong oxidizing agents, bases.
InChIKey
VZCYOOQTPOCHFL-OWOJBTEDSA-N
CAS 데이터베이스
110-16-7(CAS DataBase Reference)
NIST
2-Butenedioic acid (Z)-(110-16-7)
EPA
Maleic acid (110-16-7)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn
위험 카페고리 넘버 22-36/37/38-43
안전지침서 26-28-37-28A-46-24
유엔번호(UN No.) 3261
WGK 독일 1
RTECS 번호 OM9625000
TSCA Yes
위험 등급 8
포장분류 III
HS 번호 29173990
유해 물질 데이터 110-16-7(Hazardous Substances Data)
기존화학 물질 KE-13657
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H317 알레르기성 피부 반응을 일으킬 수 있음 피부 과민성 물질 구분 1 경고 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H318 눈에 심한 손상을 일으킴 심한 눈 손상 또는 자극성 물질 구분 1 위험 P280, P305+P351+P338, P310
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
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P405 밀봉하여 저장하시오.
NFPA 704
1
2 1

말레인산 C화학적 특성, 용도, 생산

용도

공업용 용도로는 ① 주택용 욕조, 세면대 및 자동차관련 용도의 불포화폴리에스테르수지 ② 푸마르산, 호박산 등의 식품용 ③ THF 및 PBT수지용 1.4 BDO(부탄디올)의 원료, 세정제 및 2차전지용 GBL(감마 부티로락탐)의 원료 ④ 기타 종이사이징제, 잉크, 도료, 수지의 개질제 등에 사용한다.
시약용 용도로는 화학적 방법에 의한 물질의 검출이나 정량을 위한 R&D용으로 사용한다.  

개요

Maleic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO2CCHCHCO2H. Maleic acid is the cis-isomer of butenedioic acid, where as fumaric acid is the trans-isomer. It is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, maleic acid has few applications.

화학적 성질

Maleic acid, HOOCCH:CHCOOH, also known as maleinic acid and toxilic acid,is a colorless crystalline dibasic acid. It is soluble in water and alcohol. Maleic acid is used in manufacturing synthetic resins, in textile processing, and in preserving oils and fats.

화학적 성질

Maleic acid is a white crystalline solid. Faint, acid like odor.

화학적 성질

Maleic acid occurs as a white crystalline (monoclinic) powder and possesses a faint acidulous odor and an astringent taste.
Fumaric acid and maleic acid are the simplest unsaturated carboxylic diacids. These acids experience two-step dissociation in aqueous solutions.They have the same structural formula but different spatial configurations. Fumaric acid is the trans and maleic acid the cis isomer. The physical properties of maleic acid and fumaric acid are very different. The cis isomer is less stable. Maleic acid is used in the preparation of fumaric acid by catalytic isomerization.

물리적 성질

Maleic acid is a less stable molecule than fumaric acid. The difference in heat of combustion is 22.7 kJ·mol?1. The heat of combustion is -1355 kJ / mole. Maleic acid is more soluble in water than fumaric acid. The melting point of maleic acid (135 °C) is also much lower than that of fumaric acid (287 °C). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place in maleic acid at the expense of intermolecular interactions, and that are not possible in fumaric acid for geometric reasons.

용도

Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis.
Maleic acid may be used to form acid addition salts with drugs to make them more stable, such as indacaterol maleate.

용도

manufacture of artificial resins; to retard rancidity of fats and oils in 1:10,000 (these are said to keep 3 times longer than those without the acid); dyeing and finishing wool, cotton, and silk; preparing the maleate salts of antihistamines and similar drugs.

정의

ChEBI: A butenedioic acid in which the double bond has cis- (Z)-configuration.

생산 방법

Maleic anhydride is the main source of maleic acid produced by hydration. Maleic anhydride is prepared commercially by the oxidation of benzene or by the reaction of butane with oxygen in the presence of a vanadium catalyst.

화학 반응

Although not practised commercially, maleic acid can be converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation (ethanol / palladium on carbon). It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid, being electrophilic, participates as a dienophile in many Diels - Alder reactions.

Synthesis Reference(s)

Journal of the American Chemical Society, 86, p. 4603, 1964 DOI: 10.1021/ja01075a017
The Journal of Organic Chemistry, 60, p. 6676, 1995 DOI: 10.1021/jo00126a013
Organic Syntheses, Coll. Vol. 2, p. 302, 1943

일반 설명

Maleic acid is a colorless crystalline solid having a faint odor. Maleic acid is combustible though Maleic acid may take some effort to ignite. Maleic acid is soluble in water. Maleic acid is used to make other chemicals and for dyeing and finishing naturally occurring fibers.

공기와 물의 반응

Soluble in water.

반응 프로필

Maleic acid is a colorless to white crystalline solid. Moderately toxic. When heated to decomposition Maleic acid emits irritating fumes and acrid smoke [Lewis, 3rd ed., 1993, p. 790].

위험도

Toxic by ingestion.

건강위험

Inhalation causes irritation of nose and throat. Contact with eyes or skin causes irritation.

화재위험

Special Hazards of Combustion Products: Irritating smoke containing maleic anhydride may form in fire.

Pharmaceutical Applications

Maleic acid is used in the pharmaceutical industry as a pH modifier and a buffering agent.It is also used to prevent rancidity of oils and fats; a ratio of 1 : 10 000 is usually sufficient to retard rancidity. Maleic acid is commonly used as a pharmaceutical intermediate to form the maleate salts of several categories of therapeutic agents, such as salts of antihistamines and other drug substances.

Safety Profile

Moderately toxic by ingestion and skin contact. Passes through intact skin. A skin and severe eye irritant and a corrosive. Believed to be more toxic than its isomer, fumeric acid. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes.

Safety

Maleic acid is generally regarded as a nontoxic and nonirritant material when used at low levels as an excipient. Maleic acid is used in oral, topical, and parenteral pharmaceutical formulations in addition to food products.
LD50 (mouse, oral): 2.40g/kg(7)
LD50 (rabbit, skin): 1.56g/kg
LD50 (rat, oral): 0.708g/kg

잠재적 노출

Maleic acid is used to make artificial resins, antihistamines, and to preserve (retard rancidity) of fats and oils

Carcinogenicity

In chronic feeding studies, 12 Osborne–Mendel rats per group were fed 0.5, 1.0, or 1.5% maleic acid in their diets for 2 years. Concentrations of 1.0 and 1.5% maleic acid retarded the growth rate of rats, and all concentrations of maleic acid increased mortality rate; no tumorigenesis was reported. Toxicological differences from controls were not marked, and the pathology was nonspecific.

저장

Maleic acid converts into the much higher-melting fumaric acid (mp: 287°C) when heated to a temperature slightly above its melting point.
Maleic acid is combustible when exposed to heat or flame. The bulk material should be stored in airtight glass containers and protected from light. It is recommended not to store it above 25°C.

운송 방법

UN2215 Maleic acid, Hazard class: 8; Labels: 8-Corrosive material.

Purification Methods

Crystallise the acid from acetone/pet ether (b 60-80o) or hot water. Dry it at 100o. [Beilstein 2 H 748, 2 I 303, 2 II 641, 2 III 1911, 2 IV 2199.]

비 호환성

Dust may form explosive mixture with air, 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, amines, reducing agents; alkali metals

비 호환성

Maleic acid can react with oxidizing materials. Aqueous solutions are corrosive to carbon steels.

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. Liquid: incinerate after mixing with a flammable solvent. Use afterburner for complete combustion. Solid: dissolve in a flammable solvent or package in paper and burn. See above

Regulatory Status

Included in the FDA Inactive Ingredients Database (IM and IV injections; oral tablets and capsules; topical applications). Included in nonparenteral and parenteral medicines licensed in the UK.

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