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こはく酸無水物
こはく酸無水物 · こはく酸アンヒドリド · ジヒドロフラン-2,5-ジオン · ジヒドロ-2,5-フランジオン · 2,5(3H,4H)-フランジオン · ブタン二酸無水物 · オキソラン-2,5-ジオン · 3,4-ジヒドロフラン-2,5-ジオン
識別子と物理属性
| CAS No. | 108-30-5 |
|---|---|
| 分子式 | C4H4O3 |
| 平均分子量 | 100.07 g/mol |
| 単同位体質量 | 100.01604399 g/mol |
| SMILES | O=C1CCC(=O)O1 |
| InChIKey | RINCXYDBBGOEEQ-UHFFFAOYSA-N |
| PubChem CID | 7922 |
| ChEMBL | CHEMBL1370164 |
| ChEBI | CHEBI:36595 |
| EC No. | 203-570-0 |
| DTXSID | DTXSID7021287 |
| 現地名 | こはく酸無水物 |
化学・物理的性質
| XLogP | -0.5 |
|---|---|
| 極性表面積 | 43.4 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 0 |
| 重原子数 | 7 |
| 形式電荷 | 0 |
| 複雑度 | 102 |
| 臭い | ODORLESS |
| 味 | BURNING TART TASTE |
| 密度 | 1.234 at 68 °F (NTP, 1992) - Denser than waterwill sink1.503 (also given as 1.104 and 1.234)Bulk density: 47.2 lb/cu ftRelative density (water = 1): 1.5031.104 @25 °C1,572 g/cm3 |
| Color/Form | NEEDLES FROM ALCRHOMBIC PYRAMIDS FROM CHLOROFORM OR CARBON TETRACHLORIDECOLORLESS OR LIGHT-COLORED NEEDLES OR FLAKESOrthorhombic prisms from abs alc.Succinic anhydride forms rhombic pyramidal or bipyramidal crystals. |
| 溶解度 | less than 1 mg/mL at 70 °F (NTP, 1992)Insoluble in waterIN ETHANOL AT 25 °C: 2.56 G/100 MLIN ETHER AT 25 °C: 0.64 G/100 MLIN CHLOROFORM AT 25 °C: 0.87 G/100 MLSoluble in chloroform, carbon tetrachloride, alcoholvery slightly soluble in ether and water.Solubility in water: none62.9g/l 加水分解<0.1 g/100 mL at 21 ºC (分解) |
| 引火点 | 157 °C157°C |
| 沸点 | 502 °F at 760 mmHg (NTP, 1992)261 °C at 760 mm Hg261 °C @760 [mm Hg]261 °C (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| 融点 | 247.3 °F (NTP, 1992)119.6 °C119 °C118-120 °C (lit.) |
| 蒸気密度 | 3.7 (NTP, 1992) - Heavier than airwill sink (Relative to Air)Relative vapor density (air = 1): 3.453.5 (vs air) |
| 蒸気圧 | 1 mmHg at 197.6 °F5 mmHg at 239.0 °F10 mmHg at 262.8 °F (NTP, 1992)0.0015 [mmHg]Vapor pressure = 1 mm Hg at 92 °C1.5X10-3 mm Hg at 25 °C (estrapolated)Vapor pressure, kPa at 92 °C: 1.31 [mm Hg] @92 °C1 mm Hg ( 92 °C) |
| Heat of Combustion | -1537.9 kJ/mol |
| 屈折率 | 1.4688 (estimate) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 4.67[at 20 ℃] |
| 色 | ホワイトからオフホワイト |
| 比重 | 1.2340 (20℃) |
| pH | 2.7 (10g/l, H2O) |
| Merck | 14,8870 |
| BRN | 108441 |
| 安定性 | 安定。酸化剤、強酸、強塩基、アルコール、アミンとは相容れない。水や湿気にさらさないでください。 |
| InChI | 1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2 |
| InChIKey | RINCXYDBBGOEEQ-UHFFFAOYSA-N |
| SMILES | O=C1CCC(=O)O1 |
| LogP（分配係数） | 2.44 at 40℃ |
| CAS データベース | 108-30-5(CAS DataBase Reference) |
| NISTの化学物質情報 | 2,5-Furandione, dihydro-(108-30-5) |
| EPAの化学物質情報 | Succinic anhydride (108-30-5) |
化学的特性
fine white crystalline solid
化学的特性
Succinic anhydride is an odourless, colourless needle-like or white crystalline solid natural product. Molecular formula C4H4O3, molecular weight 100.07 g/mol, relative density 1.503, melting point 237 °F. 239 °F at 5 mmHg, 239 °F at 198 °F and 1 mmHg. Soluble in chloroform, carbon tetrachloride, and ethanol; very slightly soluble in ether and water (insoluble in water). Moderately toxic and irritating, emits pungent and irritating fumes when heated to decomposition.
安全性と法規制
| GHS 分類 | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H317: May cause an allergic skin reaction [Warning Sensitization, Skin]H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]H334: May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P342+P316, P362+P364, P363, P403, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.2% (2 of 1275) of reports. |
|---|---|
| 規制情報 | Chemical: 2,5-Furandione, dihydro-Hazard Traits - Respiratory ToxicityAuthoritative List - EC Annex VI Resp. Sens. - Cat. 1Report - if used as a fragrance or flavor ingredient2,5-Furandione, dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,5-Furandione, dihydro- 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: 18-05-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/2061Status: Active Update: 05-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30019Succinic anhydride: Does not have an individual approval but may be used under an appropriate group standard |
| 火災危険 | Flash point data for this compound are not available, however, it is probably combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| 火災の可能性 | Combustible |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this chemical may include eye, skin, mucous membrane and respiratory tract irritationit may blister and burn the skin on contact.ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits acrid smoke and fumes of carbon monoxide and carbon dioxide. It may cause eye, respiratory tract, mucous membrane and skin irritation. It is a suspected carcinogen. (NTP, 1992) |
| 有害性の概要 | A skin, eye, and respiratory tract irritant[HSDB] May cause blisters and burns to skin[CAMEO] The substance is severely irritating to the eyes and is irritating to the respiratory tract. [ICSC] An irritant (severe to eyes)[MSDSonline] See ACID ANHYDRIDES. |
| 反応性グループ | Anhydrides |
| EC 分類 | Symbol: XiR: 36/37S: (2)-25 |
| Special Reports | DHHS/NTPToxicology & Carcinogenesis Studies of Succinic Anhydride in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 373 (1990) NIH Publication No. 90-2828 |
| Reactivity Profile | SUCCINIC ANHYDRIDE reacts exothermically with water. Reactions are usually slow, but might become violent if local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases. |
| Chemical Dangers | Decomposes on heating. This produces irritating fumes. |
| Air and Water Reactions | Reacts slowly with water. Insoluble in water. |
| Other Hazardous Reactions | Evaporation at 20 °C is negligiblea harmful concentration of airborne particles can, however, be reached quickly when dispersed. |
| 消火 | Fires involving this compound should be controlled using a Halon, carbon dioxide, or dry chemical extinguisher. A water spray may also be used. (NTP, 1992)Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| 応急処置措置 | Fresh air, rest.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. |
| 応急処置 | 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.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992) |
| 清掃方法 | Remove all ignition sources. Sweep spilled substance into covered containersif appropriate, moisten first to prevent dusting. |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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.STORAGE PRECAUTIONS: You should store this material at ambient temperatures, and protect it from moisture. (NTP, 1992) |
| 処分方法 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| 漏出処分 | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. |
| Preventive Measures | Prevent dispersion of dust!Inhalation /exposure can be prevented by/ local exhaust or breathing protection. Skin /exposure can be prevented by/ protective gloves. Eye /exposure can be prevented by/ safety goggles, or eye protection in combination with breathing protection if powder. /from table/Do not eat, drink, or smoke during work. /from table/ |
| Eye Prevention | Wear safety goggles or eye protection in combination with breathing protection if powder. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered. |
| Skin Prevention | Protective gloves. |
| 環境中動態 | TERRESTRIAL FATE: The half-life for the hydrolysis of succinic anhydride is 4.3 minutes(SRC), based on a rate constant of 0.0027 1/sec at 25 °C(1). The major fate of succinic anhydride in soil is expected to be hydrolysis (SRC). Succinic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.5X10-3 mm Hg(2).AQUATIC FATE: The half-life for the hydrolysis of succinic anhydride is 4.3 minutes(SRC), based on a rate constant of 0.0027 1/sec at 25 °C(1). The major fate of succinic anhydride in aquatic environments is expected to be hydrolysis(SRC). Bioconcentration of succinic anhydride in aquatic organisms is unlikely due its rapid hydrolysis(SRC). Approximately 78% of the succinic anhydride added to activated sewage sludge was biodegraded within five days(2,3)however, hydrolysis is expected to be the principal fate of succinic anhydride in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), succinic anhydride, which has a vapor pressure of 1.5X10-3 mm Hg at 25 °C(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase succinic anhydride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 70 days (SRC), calculated from its rate constant of 4.56X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). |
| 有害作用 | Dermatotoxin - Skin burns. |
| 暴露経路 | The substance can be absorbed into the body by inhalation and by ingestion. |
| Signs and Symptoms | Cough. Shortness of breath. Sore throat.Redness. Pain.Diarrhoea. Nausea. Vomiting. |
| Ongoing Test Status | 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. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=108-30-5] |
| Soil Adsorption/Mobility | Adsorption of succinic anhydride in soil is unlikely due its rapid hydrolysis(1). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ The substance irritates the eyes, the skin and the respiratory tract./SIGNS AND SYMPTOMS/ Inhalation /may cause/ cough, shortness of breath, sore throat. Skin or eye /exposure may cause/ redness, pain. Ingestion /may cause/ diarrhea, nausea, vomiting. /from table/ |
| Artificial Pollution Sources | Succinic anhydride's production and use as a chemical reactant and intermediate, in the manufacture of pharmaceuticals and esters, as a hardener for resin(1), and as an acidulant in foods(2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Approximately 78% of the succinic anhydride added to activated sewage sludge at 50 ug/L was biodegraded within five days at 25 °C (1,2)however, hydrolysis is expected to be the principal fate of succinic anhydride in water and these results are probably for succinic acid, the hydrolysis product(SRC). |
| Carcinogen Classification | Succinic anhydrideGroup 3: Not classifiable as to its carcinogenicity to humansVolume 15: (1977) Some Fumigants, the Herbicides 2,4-D and 2,4,5-T, Chlorinated Dibenzodioxins and Miscellaneous Industrial ChemicalsVolume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987440 pagesISBN 92-832-1411-0 (out of print) |
| Environmental Bioconcentration | Bioconcentration of succinic anhydride in aquatic organisms is unlikely due its rapid hydrolysis(1). Experimental bioconcentration factors (chemical concentration in fish/chemical concentration in water) of succinic anhydride in fish (Golden ide) were less than 10(2,3). |
| Volatilization from Water/Soil | Hydrolysis is expected to be the predominate fate of succinic anhydride in moist soil and water(1). Succinic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.5X10-3 mm Hg(2). |
| F | 21 |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | WN0875000 |
| 輸送番号（UN） | UN 3261 8 / PGII |
| 毒性 | LD50 orally in Rabbit: 1510 mg/kg |
| 税関コード | 29171990 |
| 危険文句（R） | 36/37-22 |
| 化審法 | (2)-921 |
| 危険表示 | Xi,Xn |
| 安全措置（S） | 25-46 |
| 危険等級 | 8Acute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1 |
| 自然発火温度 | 480 °C |
| 貯蔵分類 | 8A - Combustible corrosive hazardous materials |
| 有害物質データ | 108-30-5(Hazardous Substances Data) |
| 発がん性評価について | IARC 3 |
用途
解説
dihydro-2,5-furandione．C4H4O3(100.07)．コハク酸を無水酢酸，塩化アセチルなどと加熱すると得られる．融点120 ℃，沸点261 ℃，128 ℃(1.33 kPa)．クロロホルム，エタノールに可溶，エーテル，水に微溶．無水コハク酸は，熱水やアルカリ性水溶液によりコハク酸またはその塩になる。無水アルコールと反応してモノエステルを，アミンとの反応でモノアミドが得られる．種々の合成反応原料のほか，アルキド樹脂，接着剤，可塑剤の製造原料としても利用される．森北出版「化学辞典（第2版）
用途
加工食品用酸味料、脱水剤、合成樹脂原料
説明
Succinic anhydride, also called di hydro - 2,5- furandione , is an organic compound with the molecular formula C4H4O3.This colorless solid is the acid anhydride of succinic acid.
使用
Succinic Anhydride is an acidulant that hydrolyzes very slowly to succinic acid in water. it has thermal stability and a low melting point of 118°c which permits it to be used in products at compara- tively low temperatures. it is used as a leavening acidulant for bak- ing powder.
一般的な説明
Colorless needles or white crystalline solid. Melting point 237°F. Sublimes at 239°F at 5 mm Hg pressure; and at 198°F and 1 mm Hg pressure. Moderately toxic and an irritant.
一般的な説明
Succinic anhydride is a cyclic anhydride of succinic acid with a five-membered ring. It is widely used in the manufacture of polymeric materials, pharmaceuticals, agrochemicals, dyes, surface-active agents, and organic flame-retardant materials. It also finds application as a cross-linking agent in ion-exchange membranes and a curing agent for epoxy resins.
使用用途
無水コハク酸は、多様な分野で幅広く使用されています。以下は主な使用用途です。 1. 合成樹脂原料 無水コハク酸は、アルキド樹脂や不飽和ポリエステル樹脂の製造に用いられます。これらの樹脂は、塗料、接着剤、プラスチックなどの製品に使用されています。 特に植物を由来としたコハク酸を用いた樹脂は、生分解性プラスチックとして、資源循環や、の削減に寄与すると期待されています。 2. 有機合成 無水コハク酸は、エステル化剤やアシル化剤として、有機化合物の合成に使用されます。これにより、さまざまな化学製品や中間体の製造が可能になります。医薬品の合成、染料や顔料の製造においても重要な役割を果たす物質です。 特に、Friedel-Crafts条件下でのアシル化にしばしば用いられています。そのほか、アルケニル基を有するアルケニル無水コハク酸 (ASA) は、エポキシ樹脂硬化剤や、製紙用のサイズ剤として用いられています。
製法・合成法
調製方法
The compound is produced from succinic anhydride and hydrogen peroxide . This material must be stabilized by using a dehydrating agent such as disodium sulfate or magnesium sulfate.
製造方法
A solution of succinic acid (500 mg, 42 mmol) and triethylamine (1.23 mL, 42 mmol) in anhydrous THF (120 mL) was allowed to react with triphosgene (42 mg, 7.0 mmol) at ice-water temperature for 10 min. The reaction mixture was subsequently stirred for a further 15 min at room temperature. The solution was then filtered, and the filtrate was concentrated to dryness. The residue was crystallized from ethyl acetate to afford the desired product as white crystals (370 mg, 85%).
製造方法
無水コハク酸の製造方法 無水コハク酸の製造方法はいくつか存在します。工業的に用いられる方法は、メラミン-コハク酸プロセスです。 この方法では、メラミンとコハク酸を反応させて無水コハク酸を生成します。両者を混合し加熱すると、メラミンがコハク酸のカルボキシ基と反応して、中間体となるメラミンコハク酸塩が生成されます。その後、中間体を加熱すると無水コハク酸が生成され、メラミンが再生されます。 このプロセスでは、メラミンが反応後に再生・再利用され、触媒として機能するため、効率的に無水コハク酸を製造可能です。そのほか、を接触的に水素添加して製造する方法も一般的に用いられています。 また、コハク酸の脱水反応でも無水コハク酸を得ることが可能です。コハク酸を加熱し、無水酢酸、リン酸ペンタオキシドなどの適切な脱水剤を加えることで、水分子が除去され、無水コハク酸が生成されます。
純化方法
Crystallise the anhydride from redistilled acetic anhydride or CHCl3, then filter, wash with diethyl ether and dry it in a vacuum. [Beilstein 17 H 606, 17 V 6.]