O-kresol

o-kresol
Strukturní vzorec
Strukturní vzorec
Model molekuly
Model molekuly
Obecné
Systematický název2-methylfenol
Ostatní názvyo-kresol, 2-methylhydroxybenzen
Funkční vzorecC6H4OH-2-CH3
Sumární vzorecC7H8O
Vzhledbezbarvá pevná látka[1]
Identifikace
Registrační číslo CAS95-48-7
EC-no (EINECS/ELINCS/NLP)202-423-8
PubChem335
ChEBI28054
SMILESCc1ccccc1O
InChIInChI=1/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3
Číslo RTECSGO6300000
Vlastnosti
Molární hmotnost108,14 g/mol
Teplota tání31 °C (304 K)[1]
Teplota varu191 °C (464 K)[1]
Hustota1,047 g/cm3 (20 °C)[1]
Viskozita3,035 mPa.s (50 °C)[1]
Index lomu1,553 (20 °C)[1]
Disociační konstanta pKa10,287[1]
Rozpustnost ve vodě2,59 g/100 ml[1]
Rozpustnost v polárních
rozpouštědlech		rozpustný v ethanolu, acetonu a chloroformu[1]
Rozpustnost v nepolárních
rozpouštědlech		rozpustný v tetrachlormethanu, benzenu a rostlinných olejích[1]
Tlak páry33 Pa[1]
Měrná magnetická susceptibilita−6,74×105 μm3/g
Povrchové napětí36,90 mN/m (50 °C)[1]
Termodynamické vlastnosti
Standardní molární spalná entalpie ΔH°sp−3696 kJ/mol[1]
Bezpečnost
GHS05 – korozivní a žíravé látky
GHS05
GHS06 – toxické látky
GHS06
[1]
Nebezpečí[1]
H-větyH301 H311 H314[1]
P-větyP260 P264 P270 P280 P301+310 P301+330+331 P302+352 P303+361+353 P304+340 P305+351+338 P310 P312 P321 P322 P330 P361 P363 P405 P501[1]
Teplota vzplanutí81 °C (354 K)[1]
Teplota vznícení555 °C (828 K)[1]
Není-li uvedeno jinak, jsou použity
jednotky SI a STP (25 °C, 100 kPa).
Některá data mohou pocházet z datové položky.

o-Kresol (tj. ortho-kresol; systematický název 2-methylfenol), je organická sloučenina, isomer kresolu (CH3C6H4OH). Tato bezbarvá pevná látka se často používá na přípravu dalších sloučenin. Jedná se o methylovaný derivát fenolu a polohový izomer m-kresolu a p-kresolu.

Výroba

o-Kresol se, spolu s řadou dalších látek, získával z uhelného dehtu, získávaného při výrobě koksu. Vedlejší produkty této výroby obsahují několik procent fenolu a kresolů. Průmyslově se vyrábí methylací fenolu pomocí methanolu za katalýzy oxidy kovů:

C6H5OH + CH3OH → CH3C6H4OH + H2O

Vícenásobnou methylací vznikají xylenoly.

Dalšími způsoby jsou oxidační dekarboxylace kyseliny salicylové, oxygenace toluenu a hydrolýza 2-chlortoluenu.

Použití

o-Kresol se většinou používá na přípravu dalších sloučenin. Chlorací a esterifikací se z něj vyrábějí herbicidy jako jsou kyselina 2-methyl-4-chlorfenoxyoctová. Nitrací vzniká dinitrokresol. Kolbeho–Schmittovou karboxylací se tvoří kyselina o-kresotinová, meziprodukt při výrobě léčiv. Alkylací o-kresolu propenem vzniká karvakrol, složka silice dobromysli.

Výskyt

o-Kresol je obsažen v kastoreu, výměšku análních pachových žláz bobrů. Také se nachází v cigaretovém kouři.[2]

Odkazy

Externí odkazy

Reference

V tomto článku byl použit překlad textu z článku o-Cresol na anglické Wikipedii.

  1. ↑ a b c d e f g h i j k l m n o p q r s o-Cresol. pubchem.ncbi.nlm.nih.gov [online]. PubChem [cit. 2021-05-23]. Dostupné online. (anglicky) 
  2. ↑ R. Talhout; T. Schulz; E. Florek; J. van Benthem; P. Wester; A. Opperhuizen. Hazardous compounds in tobacco smoke. International Journal of Environmental Research and Public Health. 2011, s. 613–628. doi:10.3390/ijerph8020613. PMID 21556207. 

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