| 词条 | Adipic acid |
| 释义 |
| Watchedfields = changed | verifiedrevid = 477242708 | Name = Adipic acid | ImageFile = Adipic acid 200.svg | ImageSize = 230 | ImageAlt = Skeletal formula of adipic acid | ImageFile1 = Adipic acid molecule ball from xtal.png | ImageSize1 = 230 | ImageAlt1 = Ball-and-stick model of the adipic acid molecule | PIN = Hexanedioic acid | SystematicName = | OtherNames = Adipic acid Butane-1,4-dicarboxylic acid Hexane-1,6-dioic acid 1,4-butanedicarboxylic acid | IUPACName = | Section1 = {{Chembox Identifiers | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 76A0JE0FKJ | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D08839 | InChI = 1/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10) | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 30832 | SMILES = O=C(O)CCCCC(=O)O | InChIKey = WNLRTRBMVRJNCN-UHFFFAOYAY | PubChem = 196 | SMILES1 = C(CCC(=O)O)CC(=O)O | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1157 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = WNLRTRBMVRJNCN-UHFFFAOYSA-N | CASNo = 124-04-9 | CASNo_Ref = {{cascite|correct|CAS}} | EC_number = 204-673-3 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 191 | RTECS = AU8400000 | Section2 = {{Chembox Properties | C=6 | H=10 | O=4 | Appearance = White crystals[1] Monoclinic prisms[2] | Odor = Odorless | Density = 1.360 g/cm3 | Solubility = 14 g/L (10 °C) 24 g/L (25 °C) 1600 g/L (100 °C) | SolubleOther = Very soluble in methanol, ethanol soluble in acetone slightly soluble in cyclohexane negligible in benzene, petroleum ether insoluble in acetic acid | MeltingPtC = 152.1 | BoilingPtC = 337.5 | pKa = 4.43, 5.41 | ConjugateBase = Adipate | Viscosity = 4.54 cP (160 °C) | VaporPressure = 0.097 hPa (18.5 °C) = 0.073 mmHg | LogP = 0.08 | Section3 = {{Chembox Structure | CrystalStruct = Monoclinic | Section4 = {{Chembox Thermochemistry | DeltaHf = −994.3 kJ/mol[3] | HeatCapacity = | Section5 = | Section6 = | Section7 = {{Chembox Hazards | ExternalSDS = External MSDS | EUClass = Irritant (Xi) | RPhrases = {{R36}} | NFPA-H = 2 | NFPA-F = 1 | NFPA-R = 0 | NFPA-S = | FlashPtC = 196 | AutoignitionPtC = 422 | LD50 = 3600 mg/kg (rat) | Section8 = {{Chembox Related | OtherFunction_label = dicarboxylic acids | OtherFunction = glutaric acid pimelic acid | OtherCompounds = hexanoic acid adipic acid dihydrazide hexanedioyl dichloride hexanedinitrile hexanediamide }} Adipic acid or hexanedioic acid is the organic compound with the formula (CH2)4(COOH)2. From an industrial perspective, it is the most important dicarboxylic acid: about 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon. Adipic acid otherwise rarely occurs in nature,[4] but it is known as manufactured E number food additive E355. Preparation and reactivityAdipic acid is produced from a mixture of cyclohexanone and cyclohexanol called "KA oil", the abbreviation of ketone-alcohol oil. The KA oil is oxidized with nitric acid to give adipic acid, via a multistep pathway. Early in the reaction, the cyclohexanol is converted to the ketone, releasing nitrous acid: HOC6H11 + HNO3 → OC(CH2)5 + HNO2 + H2O Among its many reactions, the cyclohexanone is nitrosated, setting the stage for the scission of the C-C bond: HNO2 + HNO3 → NO+NO3− + H2O OC6H10 + NO+ → OC6H9-2-NO + H+ Side products of the method include glutaric and succinic acids. Nitrous oxide is produced in about one to one mole ratio to the adipic acid,[5] as well, via the intermediacy of a nitrolic acid.[4] Related processes start from cyclohexanol, which is obtained from the hydrogenation of phenol.[4][6] Alternative methods of productionSeveral methods have been developed by carbonylation of butadiene. For example, the hydrocarboxylation proceeds as follows:[4] CH2=CH−CH=CH2 + 2 CO + 2 H2O → HO2C(CH2)4CO2H Another method is oxidative cleavage of cyclohexene using hydrogen peroxide.[7] The waste product is water. Historically, adipic acid was prepared by oxidation of various fats,[8] thus the name (ultimately from Latin adeps, adipis – "animal fat"; cf. adipose tissue). ReactionsAdipic acid is a dibasic acid (it has two acidic groups). The pKa values for their successive deprotonations are 4.41 and 5.41.[9] With the carboxylate groups separated by four methylene groups, adipic acid is suited for intramolecular condensation reactions. Upon treatment with barium hydroxide at elevated temperatures, it undergoes ketonization to give cyclopentanone.[10] UsesAbout 60% of the 2.5 billion kg of adipic acid produced annually is used as monomer for the production of nylon [11] by a polycondensation reaction with hexamethylene diamine forming nylon 66. Other major applications also involve polymers; it is a monomer for production of polyurethane and its esters are plasticizers, especially in PVC. In medicineAdipic acid has been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidic drugs. It has also been incorporated into the polymeric coating of hydrophilic monolithic systems to modulate the intragel pH, resulting in zero-order release of a hydrophilic drug. The disintegration at intestinal pH of the enteric polymer shellac has been reported to improve when adipic acid was used as a pore-forming agent without affecting release in the acidic media. Other controlled-release formulations have included adipic acid with the intention of obtaining a late-burst release profile.[12] In foodsSmall but significant amounts of adipic acid are used as a food ingredient as a flavorant and gelling aid.[13] It is used in some calcium carbonate antacids to make them tart. As an acidulant in baking powders, it avoids the undesirable hygroscopic properties of tartaric acid.[14] Adipic acid, rare in nature, does occur naturally in beets, but this is not an economical source for commerce compared to industrial synthesis.[15] SafetyAdipic acid, like most carboxylic acids, is a mild skin irritant. It is mildly toxic, with a median lethal dose of 3600 mg/kg for oral ingestion by rats.[4] EnvironmentalThe production of adipic acid is linked to emissions of {{chem|N|2|O}},[16] a potent greenhouse gas and cause of stratospheric ozone depletion. At adipic acid producers DuPont and Rhodia (now Invista and Solvay, respectively), processes have been implemented to catalytically convert the nitrous oxide to innocuous products:[17] 2 N2O → 2 N2 + O2 References1. ^{{cite journal|doi=10.1002/recl.19410600805|title=The crystal structure of adipic acid|journal=Recueil des Travaux Chimiques des Pays-Bas|volume=60|issue=8|pages=605|year=2010|last1=Mac Gillavry|first1=C. H.}} 2. ^{{Cite Merck Index |monograph_id=M1420|title=Adipic Acid|date=2013|access-date=2 March 2017}} 3. ^{{CRC94}} 4. ^1 2 3 4 {{cite book | first = M. T. | last = Musser | chapter = Adipic Acid | title = Ullmann's Encyclopedia of Industrial Chemistry | publisher = Wiley-VCH | location = Weinheim | year = 2005 | doi = 10.1002/14356007.a01_269}} 5. ^{{cite journal |last1=Parmon |first1=V. N. |last2=Panov |first2=G. I. |last3=Uriarte |first3=A. |last4=Noskov |first4=A. S. |title=Nitrous oxide in oxidation chemistry and catalysis application and production |journal=Catalysis Today |volume=100 |issue=2005 |pages=115–131 |doi=10.1016/j.cattod.2004.12.012}} 6. ^{{OrgSynth|author =Ellis, B. A. |year=1925|title=Adipic Acid|volume=5|pages=9|collvol=1|collvolpages=560|prep=CV1P0018}} 7. ^{{cite journal | last1 = Sato | first1 = K. | last2 = Aoki | first2 = M. | authorlink3 = Ryōji Noyori | last3 = Noyori | first3 = R. | title = A "Green" route to adipic acid: direct oxidation of cyclohexenes with 30 percent hydrogen peroxide | journal = Science | volume = 281 | issue = 5383 | pages = 1646–47 | year = 1998 | doi = 10.1126/science.281.5383.1646| bibcode = 1998Sci...281.1646S }} 8. ^{{cite journal|last=Ince|first=Walter|title=Preparation of adipic acid and some of its derivatives|journal=Journal Chemical Society, London|year=1895|volume=67|pages=155|doi=10.1039/CT8956700155|url=https://books.google.com/books?id=BgE3AAAAYAAJ&pg=PA155}} 9. ^Cornils, Boy and Lappe, Peter (2006) "Dicarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a08_523}} 10. ^{{OrgSynth|author =Thorpe, J. F. |author2=Kon, G. A. R. |year=1925|title=Cyclopentanone|volume=5|pages=37|collvol=1|collvolpages=192|prep=CV1P0192}} 11. ^{{cite web |url=http://pcinylon.com/index.php/markets-covered/adipic-acid |title=Archived copy |accessdate=2015-05-09 |deadurl=yes |archiveurl=https://web.archive.org/web/20150518091151/http://pcinylon.com/index.php/markets-covered/adipic-acid |archivedate=2015-05-18 |df= }} PCI abstract for adipic acid 12. ^{{citation | first = Raymond | last = Roew | contribution = Adipic Acid | title = Handbook of Pharmaceutical Excipients | year = 2009 | pages = 11–12}} 13. ^{{cite web | title = Cherry Jell-O Nutrition Facts | publisher = Kraft Foods | url = http://www.kraftbrands.com/Jello/nutritioninfo.aspx?Site=1&Product=4300020003 | accessdate = 21 Mar 2012}} 14. ^{{Cite Merck Index |monograph_id=M1420|title=Adipic Acid|date=2013|access-date=2 March 2017}} 15. ^{{cite web|url=https://www.acs.org/content/acs/en/molecule-of-the-week/archive/a/adipic-acid.html|author=American Chemical Society|title=Molecule of the Week: Adipic Acid|date=9 February 2015}} 16. ^{{cite web|url=http://www.epa.gov/climatechange/Downloads/ghgemissions/US-GHG-Inventory-2013-Chapter-4-Industrial-Processes.pdf|accessdate=2013-11-29|author =US EPA|title=U.S. Greenhouse Gas Inventory Report, Chapter 4. Industrial Processes}} 17. ^{{cite book|chapter=Adipic Acid Industry — N2O Abatement|title= Non-CO2 Greenhouse Gases: Scientific Understanding, Control and Implementation|publisher= Springer|place= Netherlands|year= 2000|pages= 347–358|doi=10.1007/978-94-015-9343-4_56|author1=Reimer, R. A. |author2=Slaten, C. S. |author3=Seapan, M. |author4=Koch, T. A. |author5=Triner, V. G. |isbn=978-94-015-9343-4}} Appendix
External links
6 : Adipates|Commodity chemicals|Dicarboxylic acids|Food acidity regulators|Monomers|E-number additives |
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