Diepoxybutane (also known as butane diepoxide, butadiene diepoxide, or 1,2:3,4-diepoxybutane) is an

epoxide In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...

which is a colorless liquid at room temperature. Epoxides are very reactive due to

ring strain In organic chemistry, ring strain is a type of instability that exists when bonds in a molecule form angles that are abnormal. Strain is most commonly discussed for small rings such as cyclopropanes and cyclobutanes, whose internal angles ar ...

and diepoxybutane contains two of these groups, so it is highly reactive, more than other

ethers In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R′ r ...

. It is

hydrophilic A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press. In contrast, hydrophobes are n ...

, very flammable and easily ignited by heat or sparks. Diepoxybutane is used as a chemical intermediate, as a cross-linking agent for

polymers A polymer () is a substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeating subunits derived from one or more species of monomers. Due to their broad spectrum of properties, b ...

and textiles, and as a

preservative A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or ...

.Diepoxybutane
''Report on Carcinogens, Twelfth Edition'' (2011)

Structure, reactivity, synthesis

Diepoxybutane occurs as several

enantiomers In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

and a meso form. Diepoxybutane polymerizes in the presence of

catalysts Catalysis () is the increase in reaction rate, rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst ...

or when heated. These polymerization reactions can be violent.

Other Uses

In research diepoxybutane is used as a

chemical intermediate In chemistry, a reaction intermediate, or intermediate, is a molecular entity arising within the sequence of a stepwise chemical reaction. It is formed as the reaction product of an elementary step, from the reactants and/or preceding intermedi ...

, and in medicine for the diepoxybutane (DEB test) to screen for

Fanconi anemia Fanconi anemia (FA) is a rare, autosomal recessive genetic disease characterized by aplastic anemia, congenital defects, endocrinological abnormalities, and an increased incidence of developing cancer. The study of Fanconi anemia has improve ...

(FA) among patients with bone marrow failure syndromes. Although many chemicals are capable of DNA crosslinking, the DEB test is used because it gives fewer false negatives and positives than other chemicals.

Toxicity

Effect on humans

Diepoxybutane irritates the nose, throat and lungs, causing coughing and shortness of breath. Skin exposure can cause

chemical burns A chemical burn occurs when living tissue is exposed to a corrosive substance (such as a strong acid, base or oxidizer) or a cytotoxic agent (such as mustard gas, lewisite or arsine). Chemical burns follow standard burn classification and may ca ...

. Longer exposure periods can cause

pulmonary edema Pulmonary edema (British English: oedema), also known as pulmonary congestion, is excessive fluid accumulation in the tissue or air spaces (usually alveoli) of the lungs. This leads to impaired gas exchange, most often leading to shortness ...

, and damage to the liver and kidneys.New Jersey Department of Health and Senior Services (2000). Hazardous Substances Fact Sheet. 984-2202 (609). Retrieved 2023-03-20. https://nj.gov/health/eoh/rtkweb/documents/fs/0685.pdf.

Carcinogenicity

IARC IARC may refer to: * International Aerial Robotics Competition * International Age Rating Coalition * International Agency for Research on Cancer * International Arctic Research Center * Israel Association of Radio Communication * iArc, South Ko ...

Carcinogen - Class 1: International Agency for Research on Cancer classifies chemicals as established human carcinogens. * NTP Carcinogen - Reasonably anticipated to be a human carcinogen.

Effect on animals

It is experimentally shown that diepoxybutane can cause

tumors A neoplasm () is a type of abnormal and excessive growth of tissue. The process that occurs to form or produce a neoplasm is called neoplasia. The growth of a neoplasm is uncoordinated with that of the normal surrounding tissue, and persists ...

in rodent species at several different tissue sites and by several different exposure routes. Dermal contact with diepoxybutane caused skin tumors in mice. Injection of diepoxybutane into mice and rats caused lung tumors. Furthermore, inhalation exposure to diepoxybutane caused benign Harderian-gland tumors in mice and also increased the size of benign or malignant tumors of the

nasal cavity The nasal cavity is a large, air-filled space above and behind the nose in the middle of the face. The nasal septum divides the cavity into two cavities, also known as fossae. Each cavity is the continuation of one of the two nostrils. The nas ...

References

{{reflist Epoxides Carcinogens