Asem bènzowat

Asem bènzowat
Gambar	Gambar
	Jeneng liya Carboxybenzene; E210; Dracylic acid; Phenylmethanoic acid; BzOH;
Identifikasi
Nomor CAS	[65-85-0]
PubChem	243
Nomer EINECS	200-618-2
KEGG	D00038
MeSH	benzoic+acid
ChEBI	CHEBI:30746
Nomer RTECS	DG0875000
SMILES	O=C(O)c1ccccc1
InChI	1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
Réferènsi Baeilstein	636131
Réferènsi Gmelin	2946
3DMet	B00053
Sifat
Rumus kimia	C7H6O2
Massa molar	122.12 g mol−1
Panampilan	Colorless crystalline solid
Ambu	Faint, pleasant odor
Densitas	1.2659 g/cm3 (15 °C); 1.0749 g/cm3 (130 °C)
Titik leleh	122 °C, 395 K, 252 °F
Titik umob	250 °C, 523 K, 482 °F
Kelarutan dalam air	1.7 g/L (0 °C); 2.7 g/L (18 °C); 3.44 g/L (25 °C); 5.51 g/L (40 °C); 21.45 g/L (75 °C); 56.31 g/L (100 °C)
Kelarutan	soluble in acetone, benzene, CCl4, CHCl3, alcohol, ethyl ether, hexane, phenyls, liquid ammonia, acetates
Kelarutan dalam methanol	30 g/100 g (-18 °C); 32.1 g/100 g (-13 °C); 71.5 g/100 g (23 °C)
Kelarutan dalam ethanol	25.4 g/100 g (-18 °C); 47.1 g/100 g (15 °C); 52.4 g/100 g (19.2 °C); 55.9 g/100 g (23 °C)
Kelarutan dalam acetone	54.2 g/100 g (20 °C)
Kelarutan dalam olive oil	4.22 g/100 g (25 °C)
Kelarutan dalam 1,4-Dioxane	55.3 g/100 g (25 °C)
log P	1.87
Penetan uwab	0.16 Pa (25 °C); 0.19 kPa (100 °C); 22.6 kPa (200 °C)
Kaasaman (pKa)	4.202 (H2O); 11.02 (DMSO);
Viskositas	1.26 mPa (130 °C)
Struktur
Struktur kristal	Monoclinic
Wangun molekul	planar
Momen dipol	1.72 D in dioxane
Termokimia
Entalpi; pambentukan; standar (ΔfHo298)	-385.2 kJ/mol
Entalpi; pangobongan; standar ΔcHo298	-3228 kJ/mol
Entropi molar; standar So298	167.6 J/mol·K
Kapasitas panas, C	{{{HeactCapacity}}}
Bahaya
Bebaya utama	Irritant
NFPA 704	1 2 0
	Kejaba ditélakaké suwaliké, data ing ndhuwur kanggo; ing suhu lan tekanan standar (25°C, 100 kPa); Sangkalan lan referensi

Cithakan:Chembox Nama Sistematis Cithakan:Chembox MagSus Cithakan:Chembox RefractIndex Cithakan:Chembox LD50

Asem bènzowat /bɛnˈzoʊ.ɪk/ ya iku zat padhet putih (utawa tanpa warna) kanthi formula C ₆ H ₅ CO ₂ H. Iki minangka asem karboksilat aromatik sing paling gampang. Jeneng kasebut asalé saka permèn karèt benzoin, sing wis suwé mung siji-sijinè. Asem bènzowat ana alami ing pirang-pirang tanduran ^[6] lan dadi penengah ing biosintèsis akèh métabolit sekundér. Garam asem bènzowat digunakaké minangka pengawèt panganan. Asem bènzowat minangka prekursor penting kanggo sintèsis industri kanggo akèh zat organik liyané. Uyah lan èster saka asem bènzowat dikenal minangka bènzoates /ˈbɛnzoʊ.eɪt/.

Sejarah asem bènzowat

Asem bènzowat ditemokaké ing abad kaping nembelas. Penyulingan permen karet benzoin pisanan diterangaké dening Nostradamus (1556), lan banjur dening Alexius Pedemontanus (1560) lan Blaise de Vigenère (1596). ^[7] Justus von Liebig lan Friedrich Wöhler nemtokaké komposisi asem bènzowat. ^[8] Sing pungkasan iki uga nyelidiki babagan caranè hubungan asem hippuric karo asem bènzowat. Ing taun 1875 Salkowski nemokaké kemampuan antijamur saka asem bènzowat, sing digunakaké suwè kanggo ngreksa woh-wohan cloudberry sing ana bènzowat.^[9]

Prodhuksi asem bènzowat

Persiapan industri

Asem bènzowat diprodhuksi kanthi komersial kanthi oksidasi parsial toluene karo oksigèn . Proses kasebut dikatalisis dening kobalt utawa naphthenates mangan. Prosés kasebut nggunakaké bahan sing akèh, lan panèn ngasilaké dhuwur. ^[10] Proses industri kaping pisanan yaiku reaksi benzotrichloride (trichloromethyl benzene) karo kalsium hidroksida ing banyu, nggunakaké uyah wesi utawa zat besi minangka katalis . Kalsium bènzowat sing diasilaké diowahi dadi asem bènzowat karo asem hidroklorat . Produk kasebut ngemot turunan asem bènzowat klorida sing akèh. Amarga iku, asem bènzowat kanggo konsumsi manungsa dipikolehi kanthi distilasi garing saka permen karet benzoin. Asem bènzowat tingkat panganan saiki diproduksi kanthi sintètis.

Sintésis laboratorium

Asem bènzowat murah lan gampang kasedhiya, mula sintèsis laboratorium asem bènzowat umume ditindakaké kanggo nilai pedagogis. Iki minangka persiapan kang umum. Asem bènzowat bisa diresiki kanthi rekristalisasi saka banyu amarga larut ing banyu panas lan larut ing banyu adhem sing kurang. Nyingkiri pelarut organik kanggo rekristalisasi ndadekaké eksperimèn kasebut aman. Proses iki biasanè menehi asil panènan udakara 65%.^[11]

Saka reagèn Grignard

Bromobenzene bisa diowahi dadi asem bènzowat kanthi "karboksilasi" saka phenylmagcium bromide . ^[12] Sintèsis iki nawakaké latihan sing trep kanggo siswa nindakaké reaksi Grignard, kelas reaksi ikatan karbon-karbon sing penting ing kimia organik. ^[13] ^[14] ^[15] ^[16] ^[17]

Oksidasi senyawa bènzil

Alkohol ^[18] ^[19] lan benzil klorida lan sakbenere kabeh turunan benzil gampang dioksidasi dadi asem bènzowat.

Paripustaka

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "benzoic acid". chemister.ru. Diarsip saka sing asli ing 23 May 2014. Dibukak ing 24 October 2018.
↑ Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand.
↑ ^a ^b ^c Cithakan:Nist
↑ Harris, Daniel (2010). Quantitative Chemical Analysis (édhisi ka-8). New York: W. H. Freeman and Company. kc. AP12. ISBN 9781429254366.
↑ Olmstead, William N.; Bordwell, Frederick G. (1980). "Ion-pair association constants in dimethyl sulfoxide". The Journal of Organic Chemistry. 45 (16): 3299–3305. doi:10.1021/jo01304a033.
↑ "Scientists uncover last steps for benzoic acid creation in plants". Purdue Agriculture News. Diarsip saka sing asli ing 2021-01-25. Dibukak ing 2021-04-16.
↑ Neumüller O-A (1988). Römpps Chemie-Lexikon (édhisi ka-6). Stuttgart: Frankh'sche Verlagshandlung. ISBN 978-3-440-04516-9. OCLC 50969944.
↑ Liebig J; Wöhler F (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Chemie. 3 (3): 249–282. doi:10.1002/jlac.18320030302.
↑ Salkowski E (1875). "(tulung isi paramèter title)". Berl Klin Wochenschr. 12: 297–298.
↑ Wade, Leroy G. (2014). Organic Chemistry (édhisi ka-Pearson new international). Harlow: Pearson Education Limited. kc. 985. ISBN 978-1-292-02165-2.
↑ D. D. Perrin; W. L. F. Armarego (1988). Purification of Laboratory Chemicals (édhisi ka-3rd). Pergamon Press. kc. 94. ISBN 978-0-08-034715-8.
↑ Donald L. Pavia (2004). Introduction to Organic Laboratory Techniques: A Small Scale Approach. Thomson Brooks/Cole. kc. 312–314. ISBN 978-0-534-40833-6.
↑ Shirley, D. A. (1954). "The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cadmium". Org. React. 8: 28–58.
↑ Huryn, D. M. (1991). "Carbanions of Alkali and Alkaline Earth Cations: (ii) Selectivity of Carbonyl Addition Reactions". Ing Trost, B. M.; Fleming, I. (èd.). Comprehensive Organic Synthesis, Volume 1: Additions to C—X π-Bonds, Part 1. Elsevier Science. kc. 49–75. doi:10.1016/B978-0-08-052349-1.00002-0. ISBN 978-0-08-052349-1.
↑ "The Grignard Reaction. Preparation of Benzoic Acid" (PDF). Portland Community College. Diarsip saka sing asli (PDF) ing 26 February 2015. Dibukak ing 2015-03-12.
↑ "Experiment 9: Synthesis of Benzoic Acid via Carbonylation of a Grignard Reagent" (PDF). University of Wisconsin-Madison. Diarsip saka sing asli (PDF) ing 23 September 2015. Dibukak ing 12 March 2015.
↑ "Experiment 3: Preparation of Benzoic Acid" (PDF). Towson University. Diarsip saka sing asli (PDF) ing 13 April 2015. Dibukak ing 2015-03-12.
↑ Amakawa, Kazuhiko; Kolen'Ko, Yury V.; Villa, Alberto; Schuster, Manfred E/; Csepei, Lénárd-István; Weinberg, Gisela; Wrabetz, Sabine; Naumann d'Alnoncourt, Raoul; Girgsdies, Frank (2013). "Multifunctionality of Crystalline MoV(TeNb) M1 Oxide Catalysts in Selective Oxidation of Propane and Benzyl Alcohol". ACS Catalysis. 3 (6): 1103–1113. doi:10.1021/cs400010q.
↑ Santonastaso, Marco; Freakley, Simon J.; Miedziak, Peter J.; Brett, Gemma L.; Edwards, Jennifer K.; Hutchings, Graham J. (2014-11-21). "Oxidation of Benzyl Alcohol using in Situ Generated Hydrogen Peroxide". Organic Process Research & Development. 18 (11): 1455–1460. doi:10.1021/op500195e. ISSN 1083-6160.

[chemister-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "benzoic acid". chemister.ru. Diarsip saka sing asli ing 23 May 2014. Dibukak ing 24 October 2018.

[sioc-2] Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand.

[nist-3] Cithakan:Nist

[4] Harris, Daniel (2010). Quantitative Chemical Analysis (édhisi ka-8). New York: W. H. Freeman and Company. kc. AP12. ISBN 9781429254366.

[5] Olmstead, William N.; Bordwell, Frederick G. (1980). "Ion-pair association constants in dimethyl sulfoxide". The Journal of Organic Chemistry. 45 (16): 3299–3305. doi:10.1021/jo01304a033.

[6] "Scientists uncover last steps for benzoic acid creation in plants". Purdue Agriculture News. Diarsip saka sing asli ing 2021-01-25. Dibukak ing 2021-04-16.

[7] Neumüller O-A (1988). Römpps Chemie-Lexikon (édhisi ka-6). Stuttgart: Frankh'sche Verlagshandlung. ISBN 978-3-440-04516-9. OCLC 50969944.

[8] Liebig J; Wöhler F (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Chemie. 3 (3): 249–282. doi:10.1002/jlac.18320030302.

[9] Salkowski E (1875). "(tulung isi paramèter title)". Berl Klin Wochenschr. 12: 297–298.

[10] Wade, Leroy G. (2014). Organic Chemistry (édhisi ka-Pearson new international). Harlow: Pearson Education Limited. kc. 985. ISBN 978-1-292-02165-2.

[11] D. D. Perrin; W. L. F. Armarego (1988). Purification of Laboratory Chemicals (édhisi ka-3rd). Pergamon Press. kc. 94. ISBN 978-0-08-034715-8.

[12] Donald L. Pavia (2004). Introduction to Organic Laboratory Techniques: A Small Scale Approach. Thomson Brooks/Cole. kc. 312–314. ISBN 978-0-534-40833-6.

[13] Shirley, D. A. (1954). "The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cadmium". Org. React. 8: 28–58.

[14] Huryn, D. M. (1991). "Carbanions of Alkali and Alkaline Earth Cations: (ii) Selectivity of Carbonyl Addition Reactions". Ing Trost, B. M.; Fleming, I. (èd.). Comprehensive Organic Synthesis, Volume 1: Additions to C—X π-Bonds, Part 1. Elsevier Science. kc. 49–75. doi:10.1016/B978-0-08-052349-1.00002-0. ISBN 978-0-08-052349-1.

[15] "The Grignard Reaction. Preparation of Benzoic Acid" (PDF). Portland Community College. Diarsip saka sing asli (PDF) ing 26 February 2015. Dibukak ing 2015-03-12.

[16] "Experiment 9: Synthesis of Benzoic Acid via Carbonylation of a Grignard Reagent" (PDF). University of Wisconsin-Madison. Diarsip saka sing asli (PDF) ing 23 September 2015. Dibukak ing 12 March 2015.

[17] "Experiment 3: Preparation of Benzoic Acid" (PDF). Towson University. Diarsip saka sing asli (PDF) ing 13 April 2015. Dibukak ing 2015-03-12.

[18] Amakawa, Kazuhiko; Kolen'Ko, Yury V.; Villa, Alberto; Schuster, Manfred E/; Csepei, Lénárd-István; Weinberg, Gisela; Wrabetz, Sabine; Naumann d'Alnoncourt, Raoul; Girgsdies, Frank (2013). "Multifunctionality of Crystalline MoV(TeNb) M1 Oxide Catalysts in Selective Oxidation of Propane and Benzyl Alcohol". ACS Catalysis. 3 (6): 1103–1113. doi:10.1021/cs400010q.

[19] Santonastaso, Marco; Freakley, Simon J.; Miedziak, Peter J.; Brett, Gemma L.; Edwards, Jennifer K.; Hutchings, Graham J. (2014-11-21). "Oxidation of Benzyl Alcohol using in Situ Generated Hydrogen Peroxide". Organic Process Research & Development. 18 (11): 1455–1460. doi:10.1021/op500195e. ISSN 1083-6160.

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