(Z)-but-2-enedioic acid

C4H4O4

CAS110-16-7
GHS07 Gefahrensymbol: Gesundheitsschädlich/Reizend – Ausrufezeichen
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Identification

CAS Number
110-16-7
EC Number
203-742-5
UN Number
Index Number
607-095-00-3
PubChem CID
444266

Physical-chemical properties

Molecular Formula
C4H4O4
Molar Mass
116.07 g/mol
IUPAC Name
(Z)-but-2-enedioic acid

Chemical Identifiers

InChI
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
InChI Key
VZCYOOQTPOCHFL-UPHRSURJSA-N

Overview

(Z)-but-2-enedioic acid (CAS 110-16-7) is a dicarboxylic acid with unsaturated carbon chain and cis-configuration geometry. This organic compound, commonly known as maleic acid, represents a fundamental building block in industrial chemistry with the molecular formula C4H4O4 and a molecular weight of 116.07 g/mol. The substance is characterized by its distinctive cis-configuration, where both carboxyl groups are positioned on the same side of the double bond, distinguishing it from its trans-isomer fumaric acid. This geometric arrangement significantly influences its chemical reactivity and industrial applications. From a safety perspective, (Z)-but-2-enedioic acid requires careful handling due to its classification under multiple hazard categories. The substance carries an Acute Toxicity 4 rating and is classified as a skin and eye irritant (categories 2), along with skin sensitization potential (category 1) and specific target organ toxicity (category 3). The GHS07 pictogram and "Warning" signal word reflect these moderate hazard levels, necessitating appropriate personal protective equipment and ventilation during handling. The compound finds extensive use in polymer production, particularly in the manufacture of unsaturated polyester resins and alkyd resins used in coatings and fiberglass applications. It serves as a crucial intermediate in the production of various chemical derivatives and acts as an effective corrosion inhibitor in metal treatment processes. The substance also plays a role in pharmaceutical synthesis, where precise chemical modifications are required. While structurally different from compounds like tetrachlorosilane, (Z)-but-2-enedioic acid shares industrial relevance in specialized chemical manufacturing processes where controlled reactivity is essential. OYSI maintains reliable supply chains for (Z)-but-2-enedioic acid to support diverse European industrial applications.

Safety & Classification

Warning
Classification:

Acute Tox. 4 *; STOT SE 3; Skin Irrit. 2; Eye Irrit. 2; Skin Sens. 1

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H302

Harmful if swallowed.

H335

May cause respiratory irritation.

H315

Causes skin irritation.

H319

Causes serious eye irritation.

H317

May cause an allergic skin reaction.

Classification according to CLP Regulation (EC) No 1272/2008. The complete list of hazard and precautionary statements can be found in the Safety Data Sheet (SDS).

First Aid Measures

Inhalation

Irritant

Measures if vapours or dust are inhaled

First Aid Actions

  • +P304IF INHALED:
  • +P340Remove person to fresh air and keep comfortable for breathing.
  • +P311Call a POISON CENTER/doctor.

Related hazard statements:

Skin Contact

Irritant

Measures if substance contacts the skin

First Aid Actions

  • +P302IF ON SKIN:
  • +P352Wash with plenty of water.
  • +P361Take off immediately all contaminated clothing.
  • +P313Get medical advice/attention.

Related hazard statements:

Eye Contact

Irritant

Measures if substance gets into the eyes

First Aid Actions

  • +P305IF IN EYES:
  • +P351Rinse cautiously with water for several minutes.
  • +P338Remove contact lenses, if present and easy to do. Continue rinsing.
  • +P313Get medical advice/attention.

Related hazard statements:

Ingestion

Harmful

Measures if substance is accidentally swallowed

First Aid Actions

  • +P301IF SWALLOWED:
  • +P330Rinse mouth.
  • +P331Do NOT induce vomiting.
  • +P310Immediately call a POISON CENTER/doctor.

Related hazard statements:

General Measures

Emergency 112 | Poison Control: +49 30 19240 (DE), +33 1 45 42 59 59 (FR), +31 30 274 88 88 (NL)

First aid measures are based on CLP classification and associated P-statements. They do not replace the Safety Data Sheet (SDS). In case of emergency, always consult the full SDS and a physician.

Frequently Asked Questions

What is (Z)-but-2-enedioic acid?

(Z)-but-2-enedioic acid is a dicarboxylic acid commonly known as maleic acid, characterized by its cis-configuration double bond between carbon atoms. With the molecular formula C4H4O4 and CAS number 110-16-7, this compound has a molecular weight of 116.07 g/mol. It is classified as a hazardous substance with moderate toxicity and irritant properties, requiring careful handling in industrial and laboratory applications.

What are the physicochemical properties of (Z)-but-2-enedioic acid?

(Z)-but-2-enedioic acid appears as white crystalline powder or colorless crystals at room temperature. It has a characteristic acidic odor and is highly soluble in water, forming acidic solutions. The compound exhibits good solubility in polar organic solvents like alcohols and acetone. It has a melting point around 130-131°C and decomposes before boiling, making it thermally sensitive under high temperature conditions.

What is (Z)-but-2-enedioic acid used for?

(Z)-but-2-enedioic acid serves as an important intermediate in chemical synthesis and polymer production. It is widely used in the manufacture of unsaturated polyester resins, alkyd resins, and copolymers. The compound also finds applications in the production of fumaric acid, pharmaceuticals, and agricultural chemicals. Additionally, it serves as a chemical reagent in organic synthesis and as an additive in various industrial formulations.

How to handle (Z)-but-2-enedioic acid safely?

(Z)-but-2-enedioic acid requires careful handling due to its irritant and sensitizing properties. Workers must wear appropriate personal protective equipment including chemical-resistant gloves, safety goggles, and protective clothing. Ensure adequate ventilation in work areas and avoid generating dust. Prevent skin and eye contact, and avoid inhalation of vapors or particles. Use in well-ventilated areas or under fume hoods when processing the material.

How to store (Z)-but-2-enedioic acid properly?

(Z)-but-2-enedioic acid should be stored in a cool, dry, well-ventilated area away from heat sources and direct sunlight. Keep containers tightly closed and store in original packaging or compatible containers. Avoid storage near incompatible materials such as strong bases, oxidizing agents, and reducing agents. Maintain storage temperature below 25°C and protect from moisture to prevent degradation and ensure product stability.

What to do in case of contact with (Z)-but-2-enedioic acid?

Immediate action is required upon contact with (Z)-but-2-enedioic acid to minimize harm. For skin contact, remove contaminated clothing and wash affected area thoroughly with soap and water for at least 15 minutes. In case of eye contact, rinse immediately with clean water for 15-20 minutes and remove contact lenses if present. If inhaled, move to fresh air immediately. Seek medical attention if irritation persists or symptoms develop.

How to dispose of (Z)-but-2-enedioic acid properly?

(Z)-but-2-enedioic acid waste must be disposed of according to local and national environmental regulations. The material should not be released into drains, waterways, or the environment. Collect waste in appropriate containers and arrange disposal through licensed waste management companies. Small quantities may be neutralized carefully with appropriate bases before disposal, but this should only be done by trained personnel following proper procedures.

How to transport (Z)-but-2-enedioic acid?

(Z)-but-2-enedioic acid is not specifically classified under ADR regulations for dangerous goods transport, but still requires proper packaging and documentation. Use appropriate containers that are compatible with the chemical and ensure they are properly sealed and labeled. Transport should comply with general chemical transport regulations, including proper documentation, handling instructions, and emergency contact information for safe logistics operations.

Is (Z)-but-2-enedioic acid subject to specific regulations?

(Z)-but-2-enedioic acid is regulated under European CLP regulation due to its hazard classification and requires proper labeling with GHS07 pictogram and Warning signal word. It falls under REACH regulation requiring registration for manufacture or import above certain tonnages. The substance is not currently listed as SVHC (Substance of Very High Concern), but users must comply with occupational safety regulations and provide appropriate safety data sheets.

Where to buy (Z)-but-2-enedioic acid in Europe?

(Z)-but-2-enedioic acid is available through OYSI, a specialized European distributor of technical chemicals. OYSI provides reliable supply of quality chemical products to industrial customers across Europe, ensuring compliance with all relevant regulations and safety standards. As an established chemical distributor, OYSI offers technical support and proper documentation including safety data sheets and certificates of analysis for professional applications.

Data Sources

Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.