结构:O=C1CCC(=O)O1
HCID7922

Succinic anhydride

oxolane-2,5-dione

C4H4O3100.07 g/molCAS 108-30-5

IDENTITY

结构与身份

标准 SMILES
O=C1CCC(=O)O1
InChIKey
RINCXYDBBGOEEQ-UHFFFAOYSA-N
分子式
C4H4O3
平均分子量
100.07 g/mol
单同位素质量
100.01604399

COMPUTED

结构计算性质

已同步
XLogP
-0.5
极性表面积
43.4 Ų
氢键供体
0
氢键受体
3
可旋转键
0
重原子
7
形式电荷
0
复杂度
102

PROPERTIES

实验与物化性质

来源:PubChem
Odor

ODORLESS

Taste

BURNING TART TASTE

Density

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

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

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

157 °C

157 °C

Boiling Point

502 °F at 760 mmHg (NTP, 1992)

261 °C at 760 mm Hg

261 °C

261 °C @760 [mm Hg]

Decomposition

When heated to decomposition it emits acrid smoke and irritating fumes.

Melting Point

247.3 °F (NTP, 1992)

119.6 °C

119 °C

119.6 °C

119.6 °C

Vapor Density

3.7 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

Relative vapor density (air = 1): 3.45

Vapor Pressure

1 mmHg at 197.6 °F ; 5 mmHg at 239.0 °F; 10 mmHg at 262.8 °F (NTP, 1992)

0.0015 [mmHg]

Vapor pressure = 1 mm Hg at 92 °C

1.5X10-3 mm Hg at 25 °C (estrapolated)

Vapor pressure, kPa at 92 °C: 1.3

1 [mm Hg] @92 °C

Heat of Combustion

-1537.9 kJ/mol

GHS

GHS 分类

来源:PubChem
GHS Classification

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.

HAZARDS

危害信息

来源:PubChem
Regulatory Information

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

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 Potential

Combustible

Health Hazards

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

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 Group

Anhydrides

EC Classification

Symbol: Xi; R: 36/37; S: (2)-25

Special Reports

DHHS/NTP; Toxicology & 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 negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.

SAFETY

安全与防护

来源:PubChem
Fire Fighting

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

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

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 Methods

Remove all ignition sources. Sweep spilled substance into covered containers; if appropriate, moisten first to prevent dusting.

Nonfire Spill Response

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

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.

Spillage Disposal

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.

TOXICITY

毒理信息

来源:PubChem
Environmental Fate

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 Effects

Dermatotoxin - Skin burns.

Exposure Routes

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 anhydride

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 15: (1977) Some Fumigants, the Herbicides 2,4-D and 2,4,5-T, Chlorinated Dibenzodioxins and Miscellaneous Industrial Chemicals;Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

1987

1987

Succinic Anhydride

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).

REGULATORY

法规信息

来源:PubChem
Regulatory Information

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

PHARMACOLOGY

药理信息

来源:PubChem
Cellular Locations

Cytoplasm;Extracellular

USES

用途与制造

来源:PubChem
Uses

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

(1972) No Data

(1975) No Data

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

U.S. Imports

(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

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 Uses

Corrosion inhibitor;Not Known or Reasonably Ascertainable;pH regulating agent;Other

Methods of Manufacturing

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.

Formulations/Preparations

Grade: distilled.

...Available in US as commercial grade containing at least 99.5% of pure chemical, with maximum of 0.5% unsaturated compound...0.15% chlorides, 0.04% sulfates...and 20 mg/kg heavy metals.

Flake

General Manufacturing Information

Plastics Material and Resin Manufacturing;Not Known or Reasonably Ascertainable;Textiles, apparel, and leather manufacturing;Asphalt Paving, Roofing, and Coating Materials Manufacturing

2,5-Furandione, dihydro-: ACTIVE

Anhydrous dentifrices containing an acid anhydride to maintain sweetener stability reported. Toothpaste containing 0.50 parts succinic anhydride is an example.

Succinic anhydride is...very useful dehydrating agent for removal of small amounts of moisture in...dry food mixtures which are later to be admixed with water. ...It is capable of taking up 20% of its weight of water, and the acid formed is desirable flavoring agent in many foods.

ALIASES

名称与别名

101
SUCCINIC ANHYDRIDE108-30-5oxolane-2,5-dioneSuccinic acid anhydrideSuccinyl oxideDihydro-2,5-furandione2,5-DiketotetrahydrofuranButanedioic anhydrideSuccinyl anhydride2,5-Furandione, dihydro-Rikacid SATetrahydro-2,5-dioxofuran2,5-DioxotetrahydrofuranTetrahydro-2,5-furandioneNCI-C55696DTXSID70212876RF4O17Z8JNSC-8518DTXCID701287CHEBI:36595

REACTIONS

参与反应

1,283