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Succinic anhydride

HCID 7922
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Basic information

CAS
108-30-5
Standard SMILES
O=C1CCC(=O)O1
InChIKey
RINCXYDBBGOEEQ-UHFFFAOYSA-N
Molecular formula
C4H4O3
Average molar mass
100.07 g/mol
Monoisotopic mass
100.01604399

Overview

Succinic anhydride appears as colorless needles or white crystalline solid. Melting point 237 °F. Sublimes at 239 °F at 5 mmHg pressure; and at 198 °F and 1 mmHg pressure. Moderately toxic and an irritant.

Names & identifiers

Preferred name
Succinic anhydride
IUPAC
oxolane-2,5-dione
English name
Succinic anhydride
Molecular formula
C4H4O3
Molecular weight
100.07

Names & synonyms

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
Show more names
SANsuccinicSAATetrahydrofuran-2,5-dioneSAA15-Furandione,dihydro-2Dihydro-furan-2,5-dione
2,5-DioxotetrahydrofuranTetrahydro-2,5-furandioneNCI-C55696DTXSID70212876RF4O17Z8JNSC-8518DTXCID701287CHEBI:36595

Database identifiers

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

Properties

Computed structural properties

XLogP
-0.5
Topological polar surface area
43.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
7
Formal charge
0
Complexity
102

Experimental & physicochemical properties

PolymersPlastics & Rubber -> Acid Anhydrides, Cyclic
SpringerMaterials PropertiesSchoenflies notation
OdorODORLESS
TasteBURNING TART TASTE
Food AdditivesUse unspecified -> FDA Substance added to food
Density · 5 items

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 items

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 items

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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

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.

Danger

H302 (98.5%): Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 5 items

Chemical: 2,5-Furandione, dihydro-

Hazard Traits - Respiratory Toxicity

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)

REACH registered substance: Succinic anhydride (EC: 203-570-0)

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

Fire Hazards · 2 items

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 HazardsSYMPTOMS: 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.
Hazards Summary

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 6 items

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]

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 items

(1972) No Data

(1975) No Data

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

U.S. Imports · 3 items

(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 items

2023: 50,000 - <250,000 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.

Related reactions

1,303 records
New reaction record
HRID 1267 reaction equation
HRID 1267As reactantuspto-grants-1998_03
HRID 1501 reaction equation
HRID 1501As reactantuspto-grants-1998_03
HRID 1568 reaction equation
HRID 1568As reactantuspto-grants-1998_03
HRID 1716 reaction equation
HRID 1716As reactantuspto-grants-1998_03
HRID 2073 reaction equation
HRID 2073As reactantuspto-grants-1998_03
HRID 2114 reaction equation
HRID 2114As reactantuspto-grants-1998_03
HRID 2240 reaction equation
HRID 2240As reactantuspto-grants-1998_03
HRID 2886 reaction equation
HRID 2886As reactantuspto-grants-1998_03
Page 1 of 163

Compound notes

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

Solubility in water: none

Flash Point · 2 items

157 °C

157 °C

Boiling Point · 4 items

502 °F at 760 mmHg (NTP, 1992)

261 °C at 760 mm Hg

261 °C

261 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Melting Point · 5 items

247.3 °F (NTP, 1992)

119.6 °C

119 °C

119.6 °C

119.6 °C

Physicochemical properties

Melting point
118 · 118-120 °C (lit.)
Boiling point
261 °C · 261 °C (lit.)
Density
1 · 1,572 g/cm3
bulk density
550 · 550-600kg/m3
vapor density
3.5 · 3.5 (vs air)
vapor pressure
1 mm · 1 mm Hg ( 92 °C)
refractive index
1.4688 · 1.4688 (estimate)
Flash point
157 °C · 157°C
storage temp.
30 °C · Store below +30°C.
solubility
62.9 g/l · 62.9g/l Hydrolysis
form
Solid
pka
4.67 · 4.67[at 20 ℃]
color
White to Off-White
Specific Gravity
1.234 · 1.2340 (20℃)
PH
2.7 · 2.7 (10g/l, H2O)
Odor
Odorless
Water Solubility
0.1 g/100 · <0.1 g/100 mL at 21 ºC (decomposes)
Sensitive
Moisture Sensitive
Merck
14 · 14,8870
BRN
108441 · 108441
Stability
Stable. Incompatible with oxidising agents, strong acids, strong bases, alcohols, amines. Avoid exposure to water or moisture.
InChI
1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2
InChIKey
RINCXYDBBGOEEQ-UHFFFAOYSA-N
SMILES
O=C1CCC(=O)O1
LogP
2.44 at · 2.44 at 40℃
Toxicology and Carcinogenesis
Toxicology and Carcinogenesis Studies of Succinic Anhydride (CASRN 108-30-5) in F344/N Rats and B6C3F1 Mice (Gavage Studies)
Substances Added to Food (formerly EAFUS)
SUCCINIC ANHYDRIDE
FDA 21 CFR
175.3 · 175.300; 175.380; 175.390;176.170; 177.1210
CAS DataBase Reference
108 · 108-30-5(CAS DataBase Reference)
EWG's Food Scores
2 · 2
FDA UNII
6 RF4O17Z8J · 6RF4O17Z8J
NIST Chemistry Reference
2 · 2,5-Furandione, dihydro-(108-30-5)
IARC
3 · 3 (Vol. 15, Sup 7) 1987
EPA Substance Registry System
Succinic anhydride (108-30-5)
UNSPSC Code
41116158 · 41116158
NACRES
32 · NA.32
Symbol(GHS)
5 · GHS05
Signal word
Warning
Hazard statements
290 · H290
Precautionary statements
234 · P234-P390
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi,Xn
Risk Statements
36 · 36/37-22
Safety Statements
25 · 25-46
RIDADR
3261 · UN 3261 8 / PGII
WGK Germany
1 · 1
RTECS
875000 · WN0875000
F
21 · 21
Autoignition Temperature
480 °C · 480 °C
TSCA
TSCA listed
HazardClass
8 · 8
HS Code
29171990 · 29171990
Storage Class
8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications
4 OralEye · Acute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1
Hazardous Substances Data
108 · 108-30-5(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: 1510 mg/kg
REACH Registrations
Active
Limited Quantities
1 Kg · 1 Kg (2.2 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
· 1 item

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
EC ClassificationSymbol: Xi; R: 36/37; S: (2)-25
Special ReportsDHHS/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 · 1 item

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 DangersDecomposes on heating. This produces irritating fumes.
Air and Water ReactionsReacts slowly with water. Insoluble in water.
Other Hazardous ReactionsEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.

Safety & protection

Fire Fighting · 2 items

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 items

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 item

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.

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

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.

Disposal Methods · 1 item

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 DisposalPersonal 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 · 3 items

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 PreventionWear safety goggles or eye protection in combination with breathing protection if powder.
Fire PreventionNO open flames.
Inhalation RiskA harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
Skin PreventionProtective gloves.

Toxicology

Environmental Fate · 3 items

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 items

Cough. Shortness of breath. Sore throat.

Redness. Pain.

Diarrhoea. Nausea. Vomiting.

Ongoing Test Status · 1 item

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).
Human Toxicity Excerpts · 2 items

/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 · 1 item

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 · 1 item

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 · 6 items

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

1987

1987

Succinic Anhydride

Environmental Bioconcentration · 1 item

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/SoilHydrolysis 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).

Safety data

F
21
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
WN0875000
ridadr
UN 3261 8 / PGII
hs_code
29171990
Toxicity
LD50 orally in Rabbit: 1510 mg/kg
risk_code
36/37-22
Signal word
Warning
Symbol(GHS)
GHS05
hazard_code
Xi,Xn
safety_code
25-46
hazard_class
8
Storage Class
8A - Combustible corrosive hazardous materials
Hazard statements
H290
Limited Quantities
1 Kg (2.2 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1
Autoignition Temperature
480 °C
Precautionary statements
P234-P390
Hazardous Substances Data
108-30-5(Hazardous Substances Data)
Industry UsesCorrosion inhibitor
Methods of Manufacturing · 4 items

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 · 3 items

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 · 4 items

Plastics Material and Resin 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.

Applications · 6 items

DescriptionSuccinic 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.

UsesIt 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.

UsesSuccinic 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.

UsesSuccinic Anhydride is a useful compound in the paper manufacturing process.

General DescriptionSuccinic 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.

General DescriptionColorless 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.

Preparation methods · 1 item

PreparationA 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%).

Upstream & downstream products

Upstream raw materials

MolybdateMaleic anhydridePhosphorus oxitrichloride1,2,3,4-Tetrahydronaphthalene1,4-DioxaneDehydrolyzing agentHydrogenSuccinic acidAluminum oxide

Downstream products

Ethyl Succinyl ChlorideN-Hydroxysuccinimide4-(2-Thienyl)butyric acid1-Pyrenebutyric acidDICLOMEZINE3-(4-Oxo-3,5,6,7-tetrahydro-4H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-2-yl)propanoic acidErythromycin ethylsuccinate3-(4-Acetylaminobenzoyl)propanoic acid3-(4-Methoxybenzoyl)propionic acidFenbufenArtesunate4-Oxo-4-(2-thienyl)butyric acidSuccinamic acid3-Benzoylpropionic acid4-(4-Methoxyphenyl)butyric acidDiethyl sebacate3-(4-Chlorobenzoyl)propionic acidDaminozideMethyl 4-(4-(bis(2-hydroxyethyl)amino)phenyl)butyrateTrepibutonegamma-Chlorobutyrophenone(4S)-Hydroxy-3-methyl-2-(2-propenyl)-2-cyclopentene-1-oneMono-methyl succinateIMAZODANItaconic acid3-(4-Fluorobenzoyl)propionic acid4-(4-Aminophenyl)butyric acidGamma ButyrolactoneMethyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butyrate

Additional notes

DefinitionChEBI: Succinic anhydride is a cyclic dicarboxylic anhydride and a tetrahydrofurandione. It is functionally related to a succinic acid.