Succinic anhydride
- Iupac Name：oxolane-2,5-dione
- CAS No.: 108-30-5
- Molecular Weight：100.07276
- Modify Date.: 2022-11-12 07:47
- Introduction: 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.
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1. Names and Identifiers
- 1.1 Name
- Succinic anhydride
- 1.2 Synonyms
2,5(3H,4H)-Furandione 2,5-Diketotetrahydrofuran 2,5-Furandione, dihydro- 3,4-dihydrofuran-2,5-dione 5-Furandione,dihydro-2 bernsteinsaureanhydrid Bernsteinsaure-anhydrid Butanedioic anhydride Dihydro-2,5-furandione dihydro-5-furandione Dihydro-furan-2,5-dione Dihydrofuran-2,5-dione dihydro-furan-2.5-dione dihydrothran-2,5-dione EINECS 203-570-0 MFCD00005525 NCI-C55696 NSC 8518 Oxolan-2,5-dione Oxolane-2,5-dione Rikacid Rikacid SA SAA Succinic acid anhydride Succinyl anhydride Succinyl oxide succinylanhydride Tetrahydro-2,5-dioxofuran Tetrahydro-2,5-furandione tetrahydrofuran-2,5-dione
- 1.3 CAS No.
- 108-30-5
- 1.4 CID
- 7922
- 1.5 EINECS(EC#)
- 203-570-0
- 1.6 Molecular Formula
- C4H4O3 (isomer)
- 1.7 Inchi
- InChI=1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2
- 1.8 InChkey
- RINCXYDBBGOEEQ-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1CC(=O)OC1=O
- 1.10 Isomers Smiles
- C1CC(=O)OC1=O
2. Properties
- 2.1 Density
- 1.375
- 2.1 Melting point
- 118℃
- 2.1 Boiling point
- 261℃
- 2.1 Refractive index
- 1.497
- 2.1 Flash Point
- 261 °C at 760 mmHg
- 2.2 Precise Quality
- 100.01600
- 2.2 PSA
- 43.37000
- 2.2 logP
- -0.15000
- 2.2 Solubility
- 62.9g/l Hydrolysis
- 2.3 VaporDensity
- 3.5 (vs air)
- 2.4 Appearance
- fine white crystalline solid
- 2.5 Storage
- Moisture Sensitive. Ambient temperatures.
- 2.6 Chemical Properties
- fine white crystalline solid
- 2.7 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.
- 2.8 Decomposition
- When heated to decomposition it emits acrid smoke and irritating fumes.
- 2.9 Heat of Combustion
- -1537.9 kJ/mol
- 2.10 Odor
- ODORLESS
- 2.11 PH
- 2.7 (10g/l, H2O)
- 2.12 Water Solubility
- <0.1 g/100 mL at 21 oC (decomposes)
- 2.13 Spectral Properties
- MAX ABSORPTION (BENZENE): 278 NM (LOG E= 3.15); SADTLER REF NUMBER: 5150 (IR, PRISM)
MASS: 1122 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
IR: 449 (Sadtler Research Laboratories IR grating collection)
NMR: 6779 (Sadtler Research Laboratories spectral collection)
- 2.14 Stability
- Stable. Incompatible with oxidising agents, strong acids, strong bases, alcohols, amines. Avoid exposure to water or moisture.
- 2.15 StorageTemp
- Store below +30°C.
3. Use and Manufacturing
- 3.1 Produe Method
- The compound is produced from succinic anhydride andhydrogen peroxide . This material must be stabilized byusing a dehydrating agent such as disodium sulfate ormagnesium sulfate.
- 3.2 Purification Methods
- 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.] Succinic anhydride Preparation Products And Raw materials Preparation Products
- 3.3 Usage
- It was used in the preparation of covalently cross-linked oxidized-alginate/N-succinyl-chitosan hydrogels, as injectable systems towards tissue engineering.It was also used in preparing functionalized oxide surfaces on a chip.
4. Safety and Handling
- 4.1 Symbol
- GHS05, GHS07, GHS08
- 4.1 Hazard Codes
- Xn
- 4.1 Signal Word
- Danger
- 4.1 Risk Statements
- R22;R36/37
- 4.1 Safety Statements
- S25
- 4.1 Octanol/Water Partition Coefficient
- log Kow = 0.81 (est)
- 4.2 Fire Hazard
- Flash point data for Succinic anhydride are not available, however, Succinic anhydride is probably combustible.
- 4.3 Other Preventative 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/
- 4.4 Hazard Declaration
- H302-H314-H317-H334-H335
- 4.4 Cleanup Methods
- Remove all ignition sources. Sweep spilled substance into covered containers; if appropriate, moisten first to prevent dusting.
- 4.5 DisposalMethods
- 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.
- 4.6 RIDADR
- 25kgs
- 4.6 FirePotential
- Combustible
- 4.7 Safety Profile
- Experimental teratogenic effects. Moderately toxic by ingestion. A severe eye irritant. Mutation data reported. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANHYDRIDES.
- 4.8 Caution Statement
- P260-P280-P284-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338
- 4.8 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
- 4.9 WGK Germany
- 1
- 4.9 RTECS
- WN0875000
- 4.9 Protective Equipment and Clothing
- The substance irritates the eyes, the skin and the respiratory tract.
A severe eye irritant.
- 4.10 Reactivities and Incompatibilities
- Succinic anhydride is dimerized to 1,6-dioxaspiro[4.4]nonane-2,7dione by heating with sodium hydroxide.
- 4.11 Report
-
IARC Cancer Review: Group 3 IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.:?) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 15 ,1977,p. 265.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.:?) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
- 4.12 Skin, Eye, and Respiratory Irritations
- The substance irritates the eyes, the skin and the respiratory tract.
A severe eye irritant.
- 4.13 Safety
-
Experimental teratogenic effects. Moderately toxic by ingestion. A severe eye irritant. Mutation data reported. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANHYDRIDES.
The Hazard Codes of Succinic anhydride (CAS NO.108-30-5):?
Xi,
Xn
The Risk Statements information:
22:? Harmful if swallowed?
36/37:? Irritating to eyes and respiratory system?
The Safety Statements information:
25:? Avoid contact with eyes?
- 4.14 Sensitive
- Moisture Sensitive
- 4.15 Specification
-
?Succinic anhydride , its cas register number is 108-30-5. It also can be called 2,5-Dioxotetrahydrofuran ; Dihydro-2,5-diketotetrahydrofuran ; Dihydro-2,5-furandione ; Butanedioic anhydride ; Succinic acid anhydride ; Succinyloxide ; Tetrahydro-2,5-dioxofuran ; and SAA .
- 4.16 Toxicity
-
| 1. |
??? |
eye-rbt 750?μg SEV
|
??? |
AJOPAA ?? American Journal of Ophthalmology. 29 (1946),1363. |
| 2. |
??? |
mmo-esc 2?g/L
|
??? |
MUREAV ?? Mutation Research. 130 (1984),97. |
| 3. |
??? |
otr-ham:emb 100?μg/L
|
??? |
IJCNAW ?? International Journal of Cancer. 19 (1977),642. |
| 4. |
??? |
scu-rat TDLo:2600?mg/kg/65W-I:NEO
|
??? |
BJCAAI ?? British Journal of Cancer. 19 (1965),392. |
| 5. |
??? |
orl-rat LD50:1510?mg/kg
|
??? |
EPASR* ?? United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401M St., S.W., Washington, DC 20460) History Unknown 8EHQ-0282-0433 . |
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
Eye irritation, Category 2
Specific target organ toxicity \u2013 single exposure, Category 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed H319 Causes serious eye irritation H335 May cause respiratory irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. |
| Storage | P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
108-30-5Total: 13 Synthesis Route
8. Other Information
- 8.0 Usage
- Succinic anhydride is used as a sizing agent and curative for epoxy resin. It acts as an additive in paper production. It is utilized in the preparation of covalently cross-linked oxidized-alginate and N-succinyl-chitosan hydrogels. It serves as an intermediate for functionalized oxide surfaces on a chip and for polyester resins. Further, it finds use in cosmetics, pharmaceuticals and in coatings.
- 8.1 Merck
- 14,8870
- 8.2 BRN
- 108441
- 8.3 Description
- 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.
- 8.4 Chemical Properties
- fine white crystalline solid
- 8.5 Uses
- It was used in the preparation of covalently cross-linked oxidized-alginate/N-succinyl-chitosan hydrogels, as injectable systems towards tissue engineering.It was also used in preparing functionalized oxide surfaces on a chip.
- 8.6 Uses
- 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.
- 8.7 Uses
- Succinic Anhydride is a useful compound in the paper manufacturing process.
- 8.8 Application
- Alkyl succinic anhydride (ASA) is used as a sizing agent or wet strength additive in paper production.
- 8.9 Production Methods
- 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.
- 8.10 Preparation
- 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%).
- 8.11 Synthesis Reference(s)
- Synthetic Communications, 23, p. 419, 1993 DOI: 10.1080/00397919308009796
- 8.12 General Description
- 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.
- 8.13 Air & Water Reactions
- Reacts slowly with water. Insoluble in water.
- 8.14 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.
- 8.15 Fire Hazard
- Flash point data for Succinic anhydride are not available, however, Succinic anhydride is probably combustible.
- 8.16 Safety Profile
- Experimental teratogenic effects. Moderately toxic by ingestion. A severe eye irritant. Mutation data reported. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANHYDRIDES.
- 8.17 Purification Methods
- 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.]
9. Computational chemical data
- Molecular Weight: 100.07276g/mol
- Molecular Formula: C4H4O3
- Compound Is Canonicalized: True
- XLogP3-AA: -0.5
- Exact Mass: 100.016043985
- Monoisotopic Mass: 100.016043985
- Complexity: 102
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 43.4
- Heavy Atom Count: 7
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYBgMAAAAAAAAAAAAAAAAAAAASAAAAAAAAAAAAAAAAAAAAAAGgAAAAAACACAgAAACAAABAAIAACQCAAAAAAAAAAAAAEAAAAAABAAAAACAAAEAAAAAAADAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10. Question & Answer
-
What products will be formed when B r X 2 / K O H " style="position: relative;" tabindex="0" id="MathJax-Element-2-Frame" class="MathJax" B r X 2 / K O H B r X 2 / K O H reacts with the following compound in water at room temperature? Here is what I think is possible: O H X − " style="po...
-
Predict the structures of the intermediates/products in the following reaction sequence: In the first step, I know that aluminium chloride is playing some role, as otherwise hydronium ion would have reacted with succinic anhydride to give succinic acid. I thought of the following two possibilities:...
-
The mechanism shown in the question seems reasonable enough to me. I would note that ring opening before the attack on the π " style="position: relative;" tabindex="0" id="MathJax-Element-4-Frame" class="MathJax" π π -system is likely, but not absolutely necessary. Loss of A l C l X 3 ...
-
Here is my proposed mechanism, something tells me that the intramolecular deprotonation happens after, and that this is not concerted. Is my mechanism correct?
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