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{{unreferenced|date=May 2011}} |
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{{Chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 444438617 |
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| verifiedrevid = 455206624 |
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| ImageFile = Dodecanedioic acid.svg |
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| ImageFile = Dodecanedioic acid structure.svg |
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| ImageSize = 350px |
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| ImageSize = 250px |
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| IUPACName = dodecanedioic acid |
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| PIN = Dodecanedioic acid |
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| OtherNames = |
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| OtherNames = DDDA |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C02678 |
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| KEGG = C02678 |
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| InChIKey = TVIDDXQYHWJXFK-UHFFFAOYAC |
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| InChIKey = TVIDDXQYHWJXFK-UHFFFAOYAC |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 693-23-2 |
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| CASNo = 693-23-2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 12736 |
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| UNII = 978YU42Q6I |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = 12736 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 12213 |
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| ChemSpiderID = 12213 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 4676 |
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| ChEBI = 4676 |
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| SMILES = O=C(O)CCCCCCCCCCC(=O)O |
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| SMILES = O=C(O)CCCCCCCCCCC(=O)O |
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| InChI = 1/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16) |
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| InChI = 1/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16) |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=12|H=22|O=4 |
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| C=12 | H=22 | O=4 |
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| Appearance = white flakes |
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| Appearance = White flakes |
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| Density = 1.066g/cm3 |
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| Density = 1.066 g/cm<sup>3</sup> |
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| MeltingPt = 127-129°C |
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| MeltingPtC = 127-129 |
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| MeltingPt_notes = |
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| BoilingPt = 245°C |
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| Solubility = ethanol |
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| BoilingPtC = 245 |
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| Solubility = pH dependent |
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}} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = 220°C |
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| Autoignition = |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPtC = 220 |
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| AutoignitionPtC = |
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'''Dodecanedioic acid''' is a ] mainly used in ], top-grade coatings, painting materials, corrosion inhibitor, ], and engineering plastics. |
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'''Dodecanedioic acid''' ('''DDDA''') is a ] with the formula {{chem2|(CH2)10(CO2H)2}}. A white solid, the compound finds a variety of applications ranging from polymers to materials. The unbranched compound is the most commonly encountered C12 dicarboxylic acid. |
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] |
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{{organic-compound-stub}} |
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== Production == |
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] |
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DDDA has traditionally been produced from ] using a multi-step chemical process.<ref name=":0">{{Cite web|url=http://verdezyne.com/products/dodecanedioic-acid-ddda/|title=BIOLON® DDDA|website=verdezyne.com|access-date=2016-09-23|archive-url=https://web.archive.org/web/20160924105309/http://verdezyne.com/products/dodecanedioic-acid-ddda/|archive-date=2016-09-24|url-status=dead}}</ref> Butadiene is first converted to ] through ].<ref name=Weissermel>{{cite book | author = Klaus Weissermel, Hans-Jurgen Arpe | title = Industrial Organic Chemistry | publisher = John Wiley & Sons | edition = 3rd | date = 1997 | isbn = 3-527-28838-4}}</ref> The triene is then hydrogenated to ]. ] by air in the presence of ] gives a mixture of cyclodecanol and the ]. In the final step, this mixture oxidized to the diacid using ]. An alternative route involves ] of cyclododecene.<ref>{{cite book |doi=10.1002/14356007.a08_523.pub3|chapter=Dicarboxylic Acids, Aliphatic |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2014 |last1=Cornils |first1=Boy |last2=Lappe |first2=Peter |last3=By Staff |first3=Updated |pages=1–18 |isbn=9783527306732 }}</ref> |
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:] |
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=== Biological process === |
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] can be converted into DDDA on a laboratory scale<ref>{{Cite web|url=https://www.cathaybiotech.com/en/product.aspx|title=Dibasic acids|website=www.cathaybiotech.com|access-date=2019-03-15|archive-date=2018-10-09|archive-url=https://web.archive.org/web/20181009225209/http://www.cathaybiotech.com/en/product.aspx|url-status=dead}}</ref> with a special strain of '']'' yeast in a multi-step process.<ref>{{cite journal |last1=Kroha |first1=Kyle |title=Industrial biotechnology provides opportunities for commercial production of new long-chain dibasic acids |journal=Inform |volume=15(9) |issue=Sep 2004 |page=568 |url=http://Aocs.files.cms-plus.com/inform/2004/9/dibasicacids.pdf |accessdate=15 March 2019 |publisher=American Oil Chemists Society |archive-url=https://web.archive.org/web/20141006184727/http://aocs.files.cms-plus.com/inform/2004/9/dibasicacids.pdf |archive-date=6 October 2014 |url-status=dead }}</ref> Renewable plant-oil feedstocks sourced from ] could also be used to produce DDDA.<ref name=":0" /> |
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==Uses== |
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DDDA is used in ], top-grade coatings, painting materials, corrosion inhibitors, ]s, and ]s. It is one of two precursors to the ] ] 612.<ref>]</ref> The once commercial nylon called Qiana was produced on scale using DDDA. DDDA ester with ] is a ] of the macrocyclic lactones group commercially marketed as "Arova 16". |
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===Medical=== |
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In type 2 diabetic patients DDDA demonstrated that IV infusion helps to maintain normal blood sugar and energy levels without increasing the blood glucose load in the process.<ref>{{Cite journal |
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| pmid = 9591306 |
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| year = 1998 |
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| last1 = Greco |
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| first1 = A. V. |
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| title = The metabolic effect of dodecanedioic acid infusion in non-insulin-dependent diabetic patients |
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| journal = Nutrition |
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| volume = 14 |
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| issue = 4 |
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| pages = 351–7 |
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| last2 = Mingrone |
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| first2 = G |
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| last3 = Capristo |
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| first3 = E |
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| last4 = Benedetti |
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| first4 = G |
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| last5 = De Gaetano |
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| first5 = A |
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| last6 = Gasbarrini |
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| first6 = G |
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| doi=10.1016/s0899-9007(97)00502-9 |
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}}</ref> |
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== References == |
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<references /> |
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{{Navbox linear saturated dicarboxylic acids}} |
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] |