こはく酸無水物

Succinic anhydride

HCID 7922CAS 108-30-5

基本情報

標準SMILES
O=C1CCC(=O)O1
InChIKey
RINCXYDBBGOEEQ-UHFFFAOYSA-N
分子式
C4H4O3
平均分子量
100.07 g/mol
単同位体質量
100.01604399

名称と識別子

優先名称
Succinic anhydride
IUPAC
oxolane-2,5-dione
現地名
こはく酸無水物
英語名
Succinic anhydride
分子式
C4H4O3
分子量
100.07

名称と別名

SUCCINIC ANHYDRIDE108-30-5oxolane-2,5-dioneSuccinic acid anhydrideSuccinyl oxideDihydro-2,5-furandione2,5-DiketotetrahydrofuranButanedioic anhydrideSuccinyl anhydride2,5-Furandione, dihydro-Rikacid SATetrahydro-2,5-dioxofuran
名称をさらに表示
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-ジオンテトラヒドロフラン-2,5-ジオン3,4-ジヒドロ-2,5-フランジオン2,5-ジケトテトラヒドロフラン無水コハク酸フラン-2,5(3H,4H)-ジオン水コハク酸2,5-ジオキソテトラヒドロフランSANsuccinicSAATetrahydrofuran-2,5-dioneSAA15-Furandione,dihydro-2Dihydro-furan-2,5-dione
2,5-DioxotetrahydrofuranTetrahydro-2,5-furandioneNCI-C55696DTXSID70212876RF4O17Z8JNSC-8518DTXCID701287CHEBI:36595

データベース識別子

CAS
108-30-5、68412-02-2
PubChem CID
7922
DTXSID
DTXSID7021287
ChEMBL
CHEMBL1370164
ChEBI
CHEBI:36595
UNII
6RF4O17Z8J
EC Number
203-570-0
Nikkaji
J3.248D

物性

構造計算による物性

XLogP
-0.5
極性表面積
43.4 Ų
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

実験および物理化学的性質

OdorODORLESS
TasteBURNING TART TASTE
Density · 5 件

1.234 at 68 °F (NTP, 1992) - Denser than water; will sink

1.503 (also given as 1.104 and 1.234)

Bulk density: 47.2 lb/cu ft

Relative density (water = 1): 1.503

1.104 @25 °C

Color/Form · 4 件

NEEDLES FROM ALC; RHOMBIC PYRAMIDS FROM CHLOROFORM OR CARBON TETRACHLORIDE

COLORLESS OR LIGHT-COLORED NEEDLES OR FLAKES

Orthorhombic prisms from abs alc.

Succinic anhydride forms rhombic pyramidal or bipyramidal crystals.

Solubility · 5 件

less than 1 mg/mL at 70 °F (NTP, 1992)

Insoluble in water

IN ETHANOL AT 25 °C: 2.56 G/100 ML; IN ETHER AT 25 °C: 0.64 G/100 ML; IN CHLOROFORM AT 25 °C: 0.87 G/100 ML

Soluble in chloroform, carbon tetrachloride, alcohol; very slightly soluble in ether and water.

Solubility in water: none

Flash Point · 2 件

157 °C

157 °C

物理化学的性質

融点
118 · 118-120 °C (lit.)
沸点
261 °C · 261 °C (lit.)
比重(密度)
1 · 1,572 g/cm3
蒸気密度
3.5 · 3.5 (vs air)
蒸気圧
1 mm · 1 mm Hg ( 92 °C)
屈折率
1.4688 · 1.4688 (estimate)
化学的性質 · 2 件

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.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H302: 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.

危険有害性情報

Regulatory Information · 5 件

Chemical: 2,5-Furandione, dihydro-

Hazard Traits - Respiratory Toxicity;Authoritative List - EC Annex VI Resp. Sens. - Cat. 1;Report - if used as a fragrance or flavor ingredient

2,5-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/2061;Status: Active Update: 05-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30019

Succinic anhydride: Does not have an individual approval but may be used under an appropriate group standard

Fire Hazards · 2 件

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.

Fire PotentialCombustible
Health Hazards · 1 件

SYMPTOMS: Symptoms of exposure to this chemical may include eye, skin, mucous membrane and respiratory tract irritation; it 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)

Hazards Summary · 1 件

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.

Reactive GroupAnhydrides

安全と保護具

Fire Fighting · 2 件

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.

First Aid Measures · 4 件

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.

First Aid · 1 件

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 area; take 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 used; if 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)

Cleanup MethodsRemove all ignition sources. Sweep spilled substance into covered containers; if appropriate, moisten first to prevent dusting.
Nonfire Spill Response · 1 件

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)

Disposal Methods · 1 件

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 quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

毒性情報

Environmental Fate · 3 件

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).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.
Signs and Symptoms · 3 件

Cough. Shortness of breath. Sore throat.

Redness. Pain.

Diarrhoea. Nausea. Vomiting.

Ongoing Test Status · 1 件

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/MobilityAdsorption of succinic anhydride in soil is unlikely due its rapid hydrolysis(1).

法規制情報

Regulatory Information · 5 件

Chemical: 2,5-Furandione, dihydro-

Hazard Traits - Respiratory Toxicity;Authoritative List - EC Annex VI Resp. Sens. - Cat. 1;Report - if used as a fragrance or flavor ingredient

2,5-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/2061;Status: Active Update: 05-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30019

Succinic anhydride: Does not have an individual approval but may be used under an appropriate group standard

安全データ

F
21
wgk
1
tsca
TSCA listed
rtecs
WN0875000
ridadr
UN 3261 8 / PGII
毒性
LD50 orally in Rabbit: 1510 mg/kg

化学と産業

薬理情報

Cellular LocationsCytoplasm;Extracellular

用途と製造

Uses · 6 件

Used as an acidulant and dehydrating agent (food processing), cross-linking agent (epoxy resins and ion exchange membranes), and in gas and water treatment; Also used to make adhesives, paint drying oils, dyes, pharmaceuticals, esters, elastomers (cable coverings and extruded articles), hardeners for resins, starch modifiers in foods, succinylated monoglyceride food emulsifiers, silver haloid photographic emulsions, detergents, cosmetics, plant growth regulators, textiles, surface-active agents, lubricant additives, fire-retardants for paper, insect repellants, and herbicides; [HSDB]

Textiles (Fiber & Fabric Manufacturing) [Category: Industry];Sewer and Wastewater Treatment [Category: Industry];Plastic Composites Manufacturing [Category: Industry]

Acidulant in processed foods

Dehydrating agent in dry food mixtures

Chemical intermediate for adhesives, dyes; elastomers for special tubings, cable coverings, and extruded articles.

Manufacture of chemicals, pharmaceuticals, esters; hardener for resins, starch modifier in foods.

U.S. Exports · 3 件

(1972) No Data

(1975) No Data

(1984) 2.07X10+8 g /Anhydrides, Acyl Halides, and their derivatives/

U.S. Imports · 3 件

(1972) 4.5X10+6 G (PRINCPL CUSTOMS DISTS)

(1974) 2.7X10+6 G (PRINCPL CUSTOMS DISTS)

(1984) 1.99X10+9 g /Organic acid anhydrides/

U.S. Production · 6 件

2023: 50,000 - <250,000 lb;2022: 1,000,000 - <2,500,000 lb;2021: 400,000 - <550,000 lb;2020: 550,000 - <700,000 lb

2,5-Furandione, dihydro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1975) PROBABLY GREATER THAN 9.08X10+5 G

(1986) No Data

For more U.S. Production (Complete) data for SUCCINIC ANHYDRIDE (9 total), please visit the HSDB record page.

Industry UsesCorrosion inhibitor;Not Known or Reasonably Ascertainable;pH regulating agent;Other
Methods of Manufacturing · 4 件

Hydrogenation of maleic anhydride or fumaric acid; heating of succinic acid at elevated temperature and pressure.

...By treating succinic acid with diketene, succinyl chloride or acetic anhydride, or by reacting diethyl ester with boron chloride.

... Warming succinic acid with acetic anhydride, acetyl chloride, or phosphorus oxychloride.

Succinic anhydride is manufactured by catalytic hydrogenation of maleic anhydride. In the most widely used commercial process this reaction is performed in the liquid phase, at temperatures of 120-180 °C and at moderate pressures, in the range of 500-4000 kPa (72-580 psi). Catalysts mentioned in the patent literature include nickel, Raney nickel, palladium on different carriers, and palladium complexes.

応用分野 · 7 件

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。

調製方法 · 4 件

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.]

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