Xylylene_dichloride

Xylylene dichloride

Xylylene dichloride

Chemical compound

The chemical compound xylylene dichloride (C6H4(CH2Cl)2) is a white to light yellow sandlike solid.[1] This compound can be classified as a benzyl halide.[2][3] Xylylene dichloride is used as a vulcanizing agent to harden rubbers. It catalyzes the crosslinking of phenolic resins.[2]

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Structure and reactivity

The structure of xylylene dichloride is characterized by an benzene ring with two chloromethyl groups and four hydrogen atoms bound to it.[4] The chloromethyl groups can be located on different sites on the ring, leading to a few different possible forms. These forms are:[3]

  • o-xylylene dichloride: 1,2-bis(chloromethyl)benzene
  • m-xylylene dichloride: 1,3-bis(chloromethyl)benzene
  • p-xylylene dichloride: 1,4-bis(chloromethyl)benzene

The reactive groups of xylylene dichloride are the two CH2Cl groups.

Synthesis

Xylylene dichloride can be synthesized from benzenedimethanol by reaction with hydrogen chloride.[5] It has also been produced by photochemical chlorination of ortho-xylene.[6]

References

  1. [1]
    Xylylene dichloride. New Jersey Department of Health and Senior Services
  2. [2]
    "XYLYLENE DICHLORIDE – National Library of Medicine HSDB Database". toxnet.nlm.nih.gov.
  3. [3]
    Pubchem. "1,4-Bis(chloromethyl)benzene". pubchem.ncbi.nlm.nih.gov.
  4. [4]
    Blinnikova, Z. K.; Golding, I. R.; Tsyurupa, M. P.; Fomkin, A. A.; Pulin, A. L.; Davankov, V. A. (1 January 2018). "Hypercrosslinked Polycondensation Networks: Copolymers of p-Xylylene Dichloride". Polymer Science, Series B. 60 (1): 91–98. doi:10.1134/S1560090418010013. S2CID 258701237.
  5. [5]
    "Hydroxyl Group Substitution". Chemistry LibreTexts. 2 October 2013.
  6. [6]
    "1, 4-bis(chloromethyl)benzene synthesis technology" (2015) Chinese patent N105384595A
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