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숙신산

숙신산
숙신산 구조식 이미지
카스 번호:
110-15-6
한글명:
숙신산
동의어(한글):
숙신산;호박산;1,2-에탄디카르복실산;아숙신;에틸렌디카본산;에틸렌숙신산;웜우드;암버산;1,2-에탄디카르복실산;에틸렌숙신산;아숙신;웜우드;웜우드산;호박;석시닉애씨드;숙신산
상품명:
Succinic acid
동의어(영문):
SA;Asuccin;A 12084;Wormwood;NSC 25949;Katasuccin;NSC 106449;AMBER ACID;008008-93-3;Sal succini
CBNumber:
CB9852802
분자식:
C4H6O4
포뮬러 무게:
118.08804
MOL 파일:
110-15-6.mol

숙신산 속성

녹는점
185 °C
끓는 점
235 °C
밀도
1.19 g/mL at 25 °C(lit.)
굴절률
n20/D 1.4002(lit.)
FEMA
4719 | SUCCINIC ACID
인화점
>230 °F
저장 조건
Store at RT.
용해도
Soluble in ethanol, ethyl ether, acetone and methanol. Insoluble in toluene, benzene, carbon disulfide, carbon tetrachloride and petroleum ether.
산도 계수 (pKa)
4.16(at 25℃)
물리적 상태
Powder/Solid
색상
White to off-white
수소이온지수(pH)
2.7 (10g/l, H2O, 20℃)
수용성
80 g/L (20 ºC)
Merck
14,8869
BRN
1754069
안정성
Stable. Substances to be avoided include strong bases, strong oxidizing agents. Combustible.
InChIKey
KDYFGRWQOYBRFD-UHFFFAOYSA-N
CAS 데이터베이스
110-15-6(CAS DataBase Reference)
NIST
Butanedioic acid(110-15-6)
EPA
Butanedioic acid(110-15-6)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xi
위험 카페고리 넘버 37/38-41-36/37/38
안전지침서 26-36/37/39-37/39-39
유엔번호(UN No.) UN 3265 8/PG 3
WGK 독일 1
RTECS 번호 WM4900000
자연 발화 온도 470 °C
TSCA Yes
HS 번호 29171990
유해 물질 데이터 110-15-6(Hazardous Substances Data)
독성 LD50 orally in Rabbit: 2260 mg/kg
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H303 삼키면 유해할 수 있음 급성 독성 물질 - 경구 구분 5 P312
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H318 눈에 심한 손상을 일으킴 심한 눈 손상 또는 자극성 물질 구분 1 위험 P280, P305+P351+P338, P310
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.

숙신산 MSDS


1,2-Ethanedicarboxylic acid

숙신산 C화학적 특성, 용도, 생산

물성

석신산은 흰색의 강한 신맛이 나는 냄새가 없는 고체이다.수용액에서 석신산은 쉽게 이온화되어 짝염기인 석시네이트를 형성한다.

화학 반응

석신산은 푸마르산으로 산화되거나 다이에틸석시네이트(diethylsuccinate, (CH2CO2CH2CH3)2)와 같은 다이에스터로 전환될 수 있다. 이러한 다이에틸 에스터(diethyl ester)는 스토브 축합(Stobbe condensation) 반응의 기질이다. 석신산의 탈수는 석신산 무수물을 생성한다. 석신산은 1,4-뷰테인다이올, 말레산 무수물, 석신이미드, 2-피롤리디논 및 테트라하이드로푸란을 유도하는데 사용될 수 있다.

용도

석신산은 일부 폴리에스터의 전구물질이며, 일부 알키드 수지의 구성 성분이다.석신산은 또한 조직공학 분야와 관련이 있는 특정 생분해성 고분자의 기초 역할을 한다.식품 첨가물 및 식이 보충제로서 석신산은 미국 식품의약국에서 GRAS(Generally Recognized As Safe, 식품 첨가물에 대한 미국 식품의약국(FDA)의 합격증)로 인정되었다.

화학적 성질

Succinic acid,C02H(CH2)2C02H, also known as butanedioic acid,butane diacid, and amber acid, is a colorless odorless prisms or white crystalline powder that melts at 185°C (364 of). Soluble in water and alcohol, it is used as a chemical intermediate, Succinic acid is used in lacquers,medicine,dyes,and as a taste modifier.

용도

succinic acid is widely use as organic intermediates for the pharmaceutical, engineering plastics, resins etc.. For the synthesis of sedatives, contraceptives and cancer drugs in the pharmaceutical industry. In the chemical industry for the production of dyes, alkyd resin, glass fiber reinforced plastics, ion exchange resins and pesticides.

용도

Succinic Acid is an acidulant that is commercially prepared by the hydrogenation of maleic or fumaric acid. it is a nonhygroscopic acid but is more soluble in 25°c water than fumaric and adipic acid. it has low acid strength and slow taste build-up; it is not a substitute for normal acidulants. it combines with proteins in modifying the plasticity of bread dough. it functions as an acidulant and flavor enhancer in relishes, beverages, and hot sausages.

정의

A crystalline carboxylic acid, HOOC(CH2)2COOH, that occurs in amber and certain plants. It forms during the fermentation of sugar (sucrose).

정의

ChEBI: An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.

생명 공학 생산

Traditionally, succinic acid is produced by petrochemical synthesis using the precursor maleic acid. However, there are some microorganisms that are able to produce succinic acid (e.g. Actinobacillus succinogenes, Anaerobiospirillum succiniciproducens and Mannheimia succiniciproducens). Maximum product concentrations of 106 g.L-1 with a yield of 1.25 mol of succinic acid per mole of glucose and a productivity of 1.36 g.L-1.h-1 have been achieved by growing A. succinogenes on glucose . A high productivity of 10.40 g.L-1.h-1 has been reached with A. succinogenes growing on a complex medium with glucose in a continuous process with an integrated membrane bioreactor-electrodialysis process. In this process, the product concentration has been 83 g.L-1 . Moreover, metabolic engineering methods were used to develop strains (e.g. C. glutamicum, E. coli, S. cervisiae and Y. lipolytica) with high productivity and titer as well as low byproduct formation. For example, growing C. glutamicum strain DldhA-pCRA717 on a defined medium with glucose, a high productivity of 11.80 g.L-1.h-1 with a yield of 1.37 mol of succinic acid per mole of glucose and a titer of 83 g.L-1 has been reported after 7 h. An extended cultivation resulted in a product concentration of 146 g.L-1 after 46 h.

일반 설명

White crystals or shiny white odorless crystalline powder. pH of 0.1 molar solution: 2.7. Very acid taste.

공기와 물의 반응

Slightly water soluble.

반응 프로필

Succinic acid reacts exothermically to neutralize bases, both organic and inorganic. Can react with active metals to form gaseous hydrogen and a metal salt. Such reactions are slow in the dry, but systems may absorb water from the air to allow corrosion of iron, steel, and aluminum parts and containers. Reacts slowly with cyanide salts to generate gaseous hydrogen cyanide. Reacts with solutions of cyanides to cause the release of gaseous hydrogen cyanide. May generate flammable and/or toxic gases and heat with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. May react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Can be oxidized exothermically by strong oxidizing agents and reduced by strong reducing agents. May initiate polymerization reactions.

화재위험

Flash point data for Succinic acid are not available. Succinic acid is probably combustible.

Biotechnological Applications

Succinic acid and its derivatives are used as flavoring agents for food and beverages. This acid could be used as feedstock for dyes, insecticides, perfumes, lacquers, as well as in the manufacture of clothing, paint, links, and fibers (McKinlay et al. 2007). Succinic acid is widely used in medicine as an antistress, antihypoxic, and immunity-improving agent, in animal diets, and as a stimulator of plant growth. It is also a component of bio-based polymers such as nylons or polyesters (Kamzolova et al. 2012b). Succinate esters are precursors for the known petrochemical products such as 1,4-butanediol, tetrahydrofuran, c-butyrolactone, and various pyrrolidinone derivatives (Bechthold et al. 2008).
Succinic acid production by Y. lipolytica was reported for the first time when it was grown on ethanol under aerobic conditions and nitrogen limitation. Succinic acid amount was 63.4 g/L as the major product of batch fermentation in this process. However, the disadvantage was low yield of succinic acid on ethanol (58 %), and a high cost of production (Kamzolova et al. 2009).
Kamzolova et al. developed a novel process for the production of succinic acid. It includes the synthesis of a-ketoglutaric acid by a thiamine-auxotrophic strain Y. lipolytica VKMY-2412 from n-alkanes, and subsequent oxidation of the acid by hydrogen peroxide to succinic acid. The concentration of succinic acid and its yield were found to be 38.8 g/L and 82.45 % of n-alkane consumed, respectively (Kamzolova et al. 2012b).
Succinic acid production was also studied by genetically modified strains using glucose and glycerol as substrates. Yuzbashev et al. constructed temperaturesensitive mutant strains with mutations in the succinate dehydrogenase encoding gene SDH1 by in vitro mutagenesis-based approach. Then, the mutants were used to optimize the composition of the media for selection of transformants with the deletion in the SDH2 gene. The defects of each succinate dehydrogenase subunit prevented the growth on glucose, but the mutant strains grew on glycerol and produced succinate in the presence of the buffering agent CaCO3. Subsequent selection of the strain with deleted SDH2 gene for increased viability was allowed to obtain a strain that is capable to accumulate succinate at the level of more than 450 g/L with buffering and more than 17 g/L without buffering. Therefore, a reduced succinate dehydrogenase activity can lead to an increased succinate production (Yuzbashev et al. 2010). Y. lipolytica is able to produce succinic acid at low pH values. High amounts of succinate can be achieved by genetic engineering (Otto et al. 2013).

Safety Profile

Moderately toxic by subcutaneous route. A severe eye irritant. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Wash it with diethyl ether. Crystallise it from acetone, distilled water, or tert-butanol. Dry it under vacuum over P2O5 or conc H2SO4. Also purify it by conversion to the disodium salt which, after crystallisation from boiling water (charcoal), is treated with mineral acid to regenerate the succinic acid. The acid is then recrystallised and dried in a vacuum. [Beilstein 2 H 606, 2 IV 1908.]

숙신산 준비 용품 및 원자재

원자재

준비 용품


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