Asam p-toluenasulfonat

Asam p-toluenasulfonat[1]
P-Toluenesulfonic acid
Nama
Nama IUPAC
asam 4-metilbenzenasulfonat
Nama lain
asam tosilat
asam p-toluenasulfonat
asam tosat
PTSA
Penanda
Model 3D (JSmol)
3DMet {{{3DMet}}}
Nomor EC
Nomor RTECS {{{value}}}
  • Cc1ccc(S(=O)(O)=O)cc1
Sifat
C7H8O3S
Massa molar 172,20 g/mol
190,22 g/mol (monohidrat)
Penampilan padatan tidak berwarna (putih)
Titik lebur 106-107 °C
103-106 °C (monohidrat)
Titik didih 140 °C pada 20 mmHg
67g/100 ml
Keasaman (pKa) -2,8
Struktur
tetrahedral pada S
Bahaya
Bahaya utama iritasi kulit
Frasa-R 36/37/38
Frasa-S 26
Senyawa terkait
Kecuali dinyatakan lain, data di atas berlaku pada suhu dan tekanan standar (25 °C [77 °F], 100 kPa).
Referensi

Asam p-toluenasulfonat (PTSA), atau disingkat TsOH, adalah senyawa organik yang memiliki rumus CH3C6H4SO3H. Ia berupa padatan berwarna putih yang larut dalam air, alkohol, dan pelarut organik polar lainnya. Seringkali, TsOH merujuk pada senyawa monohidratnya, TsOH.H2O.

TsOH adalah asam organik yang kuat, satu juta kali lebih kuat daripada asam benzoat. Ia merupakan salah satu asam kuat yang berupa zat padat, sehingga mudah ditimbang. Selain itu, berbeda dengan asam mineral kuat lainnya (terutama asam nitrat, asam sulfat, dan asam perklorat), TsOH bersifat non-oksidator.

Pembuatan dan penanganan

Pada skala industri, TsOH dibuat dari sulfonasi toluena. Ia berhidrasi dengan cepat. Umumnya terdapat pula sebagian kecil asam benzenasulfonat dan asam sulfat yang dihasilkan. Ketidakmurnian ini dapat dipisahkan dengan rekristalisasi dari asam klorida, kemudian diikuti dengan pengeringan azeotropik.[2]

TsOH berguna dalam sintesis organik sebagai katalis asam yang larut dalam pelarut organik. Contoh penggunaan asam ini adalah :

Reaksi

Asam p-toluenasulfonat dapat diubah menjadi p-toluenasulfonat anhidrida dengan memanaskannya dengan fosfor pentoksida.[6]

Lihat pula

Referensi

  1. ^ Merck Index, 11th Edition, 9459.
  2. ^ Perrin, D. D. and Armarego, W. L. F., Purification of Laboratory Chemicals, Pergamon Press: Oxford, 1988.
  3. ^ H. Griesser, H.; Öhrlein, R.; Schwab, W.; Ehrler, R.; Jäger, V. (2004). "3-Nitropropanal, 3-Nitropropanol, and 3-Nitropropanal Dimethyl Acetal". Org. Synth.; Coll. Vol. 10: 577. 
  4. ^ Furuta, K. Gao, Q.-z.; Yamamoto, H. (1998). "Chiral (Acyloxy)borane Complex-catalyzed Asymmetric Diels-Alder Reaction: (1R)-1,3,4-Trimethyl-3-cyclohexene-1-carboxaldehyde". Org. Synth.; Coll. Vol. 9: 722. 
  5. ^ Imwinkelried, R.; Schiess, M.; Seebach, D. (1993). "Diisopropyl (2S,3S)-2,3-O-isopropylidenetartrate". Org. Synth.; Coll. Vol. 8: 201. 
  6. ^ L. Field and J. W. McFarland (1963). "p-Toluenesulfonic Anhydride". Org. Synth.; Coll. Vol. 4: 940. 

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