Deleng sumberé Asem bènzowat

[[Barkas:Benzoic_acid.png|jmpl|Struktur asem bènzowat]]
{{Chembox
| Watchedfields = changed
| verifiedrevid = 476995928
| ImageFileL1 = Benzoesäure.svg
| ImageSizeL1 = 100px
| ImageNameL1 = Skeletal formula
| ImageFileR1 = Benzoic-acid-3D-balls.png
| ImageSizeR1 = 100px
| ImageNameR1 = Ball-and-stick model
| ImageFile2 = Pile of benzoic acid crystals.jpg
| ImageSize2 = 270px
| PIN = Benzoic acid<ref name=iupac2013>{{cite book | title =  Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 745 | doi = 10.1039/9781849733069-00648 | isbn = 978-0-85404-182-4 }}</ref>
| SystematicName = Benzenecarboxylic acid
| OtherNames = {{ubl 
 | Carboxybenzene
 | E210
 | Dracylic acid
 | Phenylmethanoic acid
 | BzOH
}}
|Section1={{Chembox Identifiers
| Abbreviations =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8SKN0B0MIM
| InChIKey = WPYMKLBDIGXBTP-UHFFFAOYAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WPYMKLBDIGXBTP-UHFFFAOYSA-N
| CASNo = 65-85-0
| CASNo_Ref = {{cascite|correct|CAS}}
| EINECS = 200-618-2
| PubChem = 243
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 238
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 541
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB03793
| SMILES = O=C(O)c1ccccc1
| InChI = 1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
| RTECS = DG0875000
| MeSHName = benzoic+acid
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 30746
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00038
| 3DMet = B00053
| Beilstein = 636131
| Gmelin = 2946
}}
|Section2={{Chembox Properties
| C=7 | H=6 | O=2
| Appearance = Colorless crystalline solid
| Odor = Faint, pleasant odor
| Density = 1.2659 g/cm<sup>3</sup> (15&nbsp;°C)<br> 1.0749 g/cm<sup>3</sup> (130&nbsp;°C)<ref name=chemister />
| MeltingPtC = 122
| MeltingPt_ref =<ref name=GESTIS/>
| BoilingPtC = 250
| BoilingPt_ref =<ref name=GESTIS>{{GESTIS|ZVG=22810}}</ref>
| Solubility = 1.7 g/L (0&nbsp;°C)<br> 2.7 g/L (18&nbsp;°C)<br> 3.44 g/L (25&nbsp;°C)<br> 5.51 g/L (40&nbsp;°C)<br> 21.45 g/L (75&nbsp;°C)<br> 56.31 g/L (100&nbsp;°C)<ref name=chemister>{{cite web|url=http://chemister.ru/Database/properties-en.php?dbid=1&id=679|title=benzoic acid|website=chemister.ru|access-date=24 October 2018|archive-date=23 May 2014|archive-url=https://web.archive.org/web/20140523230141/http://chemister.ru/Database/properties-en.php?dbid=1&id=679|url-status=dead}}</ref><ref name=sioc>{{cite book|last1 = Seidell|first1 = Atherton|last2 = Linke|first2 = William F.|year = 1952|title = Solubilities of Inorganic and Organic Compounds|publisher = Van Nostrand|url = https://books.google.com/books?id=k2e5AAAAIAAJ}}</ref>
| pKa = {{ubl 
 | 4.202 (H<sub>2</sub>O)<ref>{{cite book|last=Harris|first=Daniel|title=Quantitative Chemical Analysis|year=2010|publisher=W. H. Freeman and Company|location=New York|isbn=9781429254366|pages=AP12|edition=8}}</ref> 
 | 11.02 (DMSO)<ref>{{cite journal |last1=Olmstead |first1=William N. |last2=Bordwell |first2=Frederick G. |title=Ion-pair association constants in dimethyl sulfoxide |journal=The Journal of Organic Chemistry |date=1980 |volume=45 |issue=16 |pages=3299–3305 |doi=10.1021/jo01304a033}}</ref>
}}
| SolubleOther = soluble in [[acetone]], [[benzene]], [[carbon tetrachloride|CCl<sub>4</sub>]], [[chloroform|CHCl<sub>3</sub>]], [[ethanol|alcohol]], [[ethyl ether]], [[hexane]], [[phenyl]]s, liquid [[ammonia]], [[acetate]]s
| Solubility1 = 30 g/100 g (-18&nbsp;°C)<br> 32.1 g/100 g (-13&nbsp;°C)<br> 71.5 g/100 g (23&nbsp;°C)<ref name=chemister />
| Solvent1 = methanol
| Solubility2 = 25.4 g/100 g (-18&nbsp;°C)<br> 47.1 g/100 g (15&nbsp;°C)<br> 52.4 g/100 g (19.2&nbsp;°C)<br> 55.9 g/100 g (23&nbsp;°C)<ref name=chemister />
| Solvent2 = ethanol
| Solubility3 = 54.2 g/100 g (20&nbsp;°C)<ref name=chemister />
| Solvent3 = acetone
| Solubility4 = 4.22 g/100 g (25&nbsp;°C)<ref name=chemister />
| Solvent4 = olive oil
| Solubility5 = 55.3 g/100 g (25&nbsp;°C)<ref name=chemister />
| Solvent5 = 1,4-Dioxane
| pKb =
| IsoelectricPt =
| LambdaMax =
| Absorbance =
| SpecRotation =
| RefractIndex = 1.5397 (20&nbsp;°C)<br> 1.504 (132&nbsp;°C)<ref name=chemister />
| Viscosity = 1.26 mPa (130&nbsp;°C)
| VaporPressure = 0.16 Pa (25&nbsp;°C)<br> 0.19 kPa (100&nbsp;°C)<br> 22.6 kPa (200&nbsp;°C)<ref name=nist>{{nist|name=Benzoic acid| id= C65850|accessdate=2014-05-23|mask=FFFF|units=SI}}</ref>
| LogP = 1.87
| MagSus = -70.28·10<sup>−6</sup> cm<sup>3</sup>/mol
 }}
|Section3={{Chembox Structure
| CrystalStruct = [[Monoclinic]]
| Coordination =
| MolShape = [[Plane (geometry)|planar]]
| Dipole = 1.72 [[Debye|D]] in [[dioxane]]
 }}
|Section4={{Chembox Thermochemistry
| DeltaHf = -385.2 kJ/mol<ref name=chemister />
| DeltaHc = -3228 kJ/mol<ref name=nist />
| Entropy = 167.6 J/mol·K<ref name=chemister />
| HeatCapacity = 146.7 J/mol·K<ref name=nist />
 }}
|Section7={{Chembox Hazards
| ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/b1356.htm JT Baker]
| GHSPictograms = {{GHS05}}{{GHS07}}<ref name="sigma">{{Sigma-Aldrich| id= w213101|name=Benzoic acid|accessdate=2014-05-23}}</ref>
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|318|335}}<ref name="sigma" />
| PPhrases = {{P-phrases|261|280|305+351+338}}<ref name="sigma" />
| MainHazards = Irritant
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| NFPA-S =
| FlashPtC = 121.5
| FlashPt_ref = <ref name=GESTIS/>
| AutoignitionPtC = 571
| AutoignitionPt_ref = <ref name=GESTIS/>
| ExploLimits =
| PEL =
| LD50 = 1700 mg/kg (rat, oral)
 }}
|Section8={{Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunction = [[Hydroxybenzoic acid]]s<br />[[Aminobenzoic acid]]s,<br />[[Nitrobenzoic acid]]s,<br />[[Phenylacetic acid]]
| OtherFunction_label = [[carboxylic acid]]s
| OtherCompounds = [[Benzaldehyde]],<br />[[Benzyl alcohol]],<br />[[Benzoyl chloride]],<br />[[Benzylamine]],<br />[[Benzamide]]
 }}
}}

'''Asem bènzowat'''  {{IPAc-en|b|ɛ|n|ˈ|z|oʊ|.|ɪ|k}} ya iku zat padhet putih (utawa tanpa warna) kanthi formula C <sub>6</sub> H <sub>5</sub> CO <sub>2</sub> 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 <ref>{{Cite web|url=http://www.purdue.edu/newsroom/releases/2012/Q3/scientists-uncover-last-steps-for-benzoic-acid-creation-in-plants.html|title=Scientists uncover last steps for benzoic acid creation in plants|publisher=Purdue Agriculture News|access-date=2021-04-16|archive-date=2021-01-25|archive-url=https://web.archive.org/web/20210125014732/https://www.purdue.edu/newsroom/releases/2012/Q3/scientists-uncover-last-steps-for-benzoic-acid-creation-in-plants.html|url-status=dead}}</ref> lan dadi penengah ing biosintèsis akèh [[Métabolit sékundèr|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''' {{IPAc-en|ˈ|b|ɛ|n|z|oʊ|.|eɪ|t}}.

== 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). <ref>{{Cite book|title=Römpps Chemie-Lexikon|last=Neumüller O-A|publisher=Frankh'sche Verlagshandlung|year=1988|isbn=978-3-440-04516-9|edition=6|location=Stuttgart|oclc=50969944}}</ref> Justus von Liebig lan Friedrich Wöhler nemtokaké komposisi asem bènzowat. <ref>{{Cite journal|last=Liebig J|author-link=Justus von Liebig|last2=Wöhler F|author-link2=Friedrich Wöhler|year=1832|title=Untersuchungen über das Radikal der Benzoesäure|journal=[[Liebigs Annalen|Annalen der Chemie]]|volume=3|issue=3|pages=249–282|doi=10.1002/jlac.18320030302}}</ref> 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.<ref>{{Cite journal|last=Salkowski E|year=1875|title=(tulung isi paramèter title)|journal=Berl Klin Wochenschr|volume=12|pages=297–298}}</ref>

== 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. <ref>{{Cite book|title=Organic Chemistry|last=Wade|first=Leroy G.|date=2014|publisher=Pearson Education Limited|isbn=978-1-292-02165-2|edition=Pearson new international|location=Harlow|page=985|ref=OrgChem}}</ref> 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 klorid|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.
[[Barkas:Benzoic_acid-chemical-synthesis-1.svg|pus]]

=== Sintésis laboratorium ===
[[Barkas:Sublimation_of_Benzoic_acid.jpg|jmpl|Sublimasi asem bènzowat]]
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 [[Kalor|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%.<ref>{{Cite book|url=https://archive.org/details/purificationofla0000perr_n7w5|title=Purification of Laboratory Chemicals|last=D. D. Perrin|last2=W. L. F. Armarego|publisher=Pergamon Press|year=1988|isbn=978-0-08-034715-8|edition=3rd|pages=[https://archive.org/details/purificationofla0000perr_n7w5/page/94 94]|url-access=registration}}</ref>

=== Saka reagèn Grignard ===
''Bromobenzene'' bisa diowahi dadi asem bènzowat kanthi "karboksilasi" saka ''phenylmagcium bromide'' . <ref>{{Cite book|title=Introduction to Organic Laboratory Techniques: A Small Scale Approach|last=Donald L. Pavia|publisher=Thomson Brooks/Cole|year=2004|isbn=978-0-534-40833-6|pages=312–314}}</ref> Sintèsis iki nawakaké latihan sing trep kanggo siswa nindakaké reaksi Grignard, kelas reaksi ikatan karbon-karbon sing penting ing kimia organik. <ref>{{Cite journal|last=Shirley|first=D. A.|year=1954|title=The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cadmium|journal=[[Org. React.]]|volume=8|pages=28–58}}</ref> <ref>{{Cite book|title=Comprehensive Organic Synthesis, Volume 1: Additions to C&mdash;X π-Bonds, Part 1|last=Huryn|first=D. M.|publisher=[[Elsevier Science]]|year=1991|isbn=978-0-08-052349-1|editor-last=Trost|editor-first=B. M.|editor-link=Barry Trost|pages=49–75|chapter=Carbanions of Alkali and Alkaline Earth Cations: (ii) Selectivity of Carbonyl Addition Reactions|doi=10.1016/B978-0-08-052349-1.00002-0|editor-last2=Fleming|editor-first2=I.|editor-link2=Ian Fleming (chemist)}}</ref> <ref>{{Cite web|url=http://spot.pcc.edu/~chandy/242/PreparationofBenzoicAcid.pdf|title=The Grignard Reaction. Preparation of Benzoic Acid|publisher=Portland Community College|archive-url=https://web.archive.org/web/20150226115836/http://spot.pcc.edu/~chandy/242/PreparationofBenzoicAcid.pdf|archive-date=26 February 2015|access-date=2015-03-12}}</ref> <ref>{{Cite web|url=http://www.chem.wisc.edu/courses/342/Fall2004/Experiment_9.pdf|title=Experiment 9: Synthesis of Benzoic Acid via Carbonylation of a Grignard Reagent|publisher=University of Wisconsin-Madison|archive-url=https://web.archive.org/web/20150923202908/http://www.chem.wisc.edu/courses/342/Fall2004/Experiment_9.pdf|archive-date=23 September 2015|access-date=12 March 2015}}</ref> <ref>{{Cite web|url=http://pages.towson.edu/jdiscord/WWW/332_Lab_Info/332LabsIRPMR/Expt3Grignard.pdf|title=Experiment 3: Preparation of Benzoic Acid|publisher=Towson University|archive-url=https://web.archive.org/web/20150413011353/http://pages.towson.edu/jdiscord/www/332_lab_info/332labsirpmr/expt3grignard.pdf|archive-date=13 April 2015|access-date=2015-03-12}}</ref>

=== Oksidasi senyawa bènzil ===
Alkohol <ref>{{Cite journal|last=Amakawa|first=Kazuhiko|last2=Kolen'Ko|first2=Yury V.|last3=Villa|first3=Alberto|last4=Schuster|first4=Manfred E/|last5=Csepei|first5=Lénárd-István|last6=Weinberg|first6=Gisela|last7=Wrabetz|first7=Sabine|last8=Naumann d'Alnoncourt|first8=Raoul|last9=Girgsdies|first9=Frank|year=2013|title=Multifunctionality of Crystalline MoV(TeNb) M1 Oxide Catalysts in Selective Oxidation of Propane and Benzyl Alcohol|url=https://www.researchgate.net/publication/278196177|journal=ACS Catalysis|volume=3|issue=6|pages=1103–1113|doi=10.1021/cs400010q}}</ref> <ref>{{Cite journal|last=Santonastaso|first=Marco|last2=Freakley|first2=Simon J.|last3=Miedziak|first3=Peter J.|last4=Brett|first4=Gemma L.|last5=Edwards|first5=Jennifer K.|last6=Hutchings|first6=Graham J.|date=2014-11-21|title=Oxidation of Benzyl Alcohol using in Situ Generated Hydrogen Peroxide|journal=Organic Process Research & Development|volume=18|issue=11|pages=1455–1460|doi=10.1021/op500195e|issn=1083-6160}}</ref> lan benzil klorida lan sakbenere kabeh turunan benzil gampang dioksidasi dadi asem bènzowat.

<section data-mw-cx-source="Google" id="cxTargetSection38" rel="cx:Section">
Asem bènzowat alami kanthi alami uga éster ing pirang-pirang spesies tanduran lan kèwan. Jumlah sing bisa ditemokaké ditemokaké ing pirang-pirang woh wohan bèri (udakara 0,05%). Woh-wohan sing mateng saka pirang-pirang ''spesies Vaccinium'' (kayata [[Kranbéri|cranberry]], ''V. vitis macrocarpon'' ; [[Bilbéri|bilberry]], ''V. myrtillus'' ) ngemot 0,03-0,13% asem bènzowat. Asem bènzowat uga dibentuk ing [[apel]] sawisé infeksi jamur ''Nectria galligena'' . Ing antaranè kéwan, asem bènzowat dikenal utamanè ing spesies omnivora utawa fitofagosa, kayata, viscera lan otot ''ptarmigan rock'' ( ''Lagopus muta'' ) uga sekresi kelenjar muskoxen lanang ( ''Ovibos moschatus'' ) utawa gajah Asia ( ''[[Gajah Asia|Elephas maximus]]'' ) . <ref name="concise">{{Cite web|url=http://www.inchem.org/documents/cicads/cicads/cicad26.htm|title=Concise International Chemical Assessment Document 26: BENZOIC ACID AND SODIUM BENZOATE}}</ref> Gum benzoin ngemot nganti 20% asem bènzowat lan 40% ester asem bènzowat. <ref>{{Cite journal|year=1972|title=Direct Colorimetric Determination of Hippuric Acid in Urine|journal=Clin Chem|volume=18|issue=4|pages=349–351|doi=10.1093/clinchem/18.4.349|pmid=5012256}}</ref>. Ing babagan biosintèsis, bènzowat diproduksi ing tanduran saka ''asem cinnamic.'' <ref name="Vogt">{{Cite journal|last=Vogt, T.|year=2010|title=Phenylpropanoid Biosynthesis|journal=Molecular Plant|volume=3|pages=2–20|doi=10.1093/mp/ssp106|pmid=20035037}}</ref> Jalur wis diidentifikasi saka fènol liwat ''4-hydroxybènzoate'' . <ref name="Juteau">{{Cite journal|last=Juteau|first=Pierre|last2=Valérie Côté|last3=Marie-France Duckett|last4=Réjean Beaudet|last5=François Lépine|last6=Richard Villemur|last7=Jean-Guy Bisaillon|date=January 2005|title=Cryptanaerobacter phenolicus gen. nov., sp. nov., an anaerobe that transforms phenol into benzoate via 4-hydroxybenzoate|journal=International Journal of Systematic and Evolutionary Microbiology|volume=55|issue=1|pages=245–250|doi=10.1099/ijs.0.02914-0|pmid=15653882|doi-access=free}}</ref> 
</section>

== Paripustaka ==

[[Kategori:Kimiya]]