adipic acid synthesis mechanism

2018 Oct 23;10(20):4755-4760. doi: 10.1002/cctc.201801151. Properties of Novel Polyesters Made from Renewable 1,4-Pentanediol. The procedure is written for a specific amount of cyclohexene. 11/25/12 Disadvantage of the synthesis. First, O-acetylation of galactaric acid secondary hydroxyl groups was performed using acetic anhydride as a … 1. Then extract … II. 3 Sodium tungstate is soluble in water but the cyclohexene is not. ChemCatChem. Adipic acid can be synthesized by taking cyclohexene as the starting material and exposing it to oxidation-type conditions. All Answers (2) 4th Nov, 2017. Their reactions with bases, called "neutralizations", are accompanied by … The cleavage of double bonds by oxidation is useful in the synthesis of acids and ketones and determining structures. Attach the Dean Stark trap and a reflux condenser. Share . Kindly suggest correct mechanism for oxidation of cyclohexanol to adipic acid using HNO3. Benzene is hydrogenated using Ni-Al2 O 3 catalyst at 370–800 psi to cyclohexane. Nylon 6-6 synthesis is an example of a condensation polymerization, as well as a step-growth polymerization. This pathway was found to be the reverse adipate degradation pathway. Carboxylic acids donate hydrogen ions if a base is present to accept them. Jianzhou Gui, Dan Liu, Xiaohui Cong, Xiaotong Zhang, Heng Jiang, Zhide Hu, Zhaolin Sun. Green adipic acid synthesis by cyclohexene oxidation with hydrogen peroxide in presence of a catalyst. Download Citation | The Kinetics for the Electrochemical Synthesis of Adipic Acid | A new method of synthesis of adipic acid from cyclohexanol was reported. Nearly all commercial adipic acid is produced from cyclohexane. Epub 2013 Nov 12. However, currently there is no suitable bio-adipic acid synthesis process. If your. 16. Where such data are unavailable, it appears that some countries have used plant capacity information as a proxy. Stadler BM, Brandt A, Kux A, Beck H, de Vries JG. Lin J, Song H, Shen X, Wang B, Xie S, Deng W, Wu D, Zhang Q, Wang Y. Chem Commun (Camb). Under the influence of the vanadate the hemihydrate of cyclohexanedione is rapidly converted to adipic acid, whereas in the absence of vanadate this substance is slowly broken down to glutaric acid, succinic acid and oxalic acid. Heat the mixture under reflux. C 25H 54ClN (146.1) C 6H 10O 4 Classification Reaction types and substance classes oxidation, phase transfer catalysis peroxide, alkene, carboxylic acid Work methods developing biobased adipic acid.32,33 Two pathways for the synthesis of diglycidyl adipate were evaluated: (i) the first being by the direct, one pot reaction between adipic acid and epichlorohydrin based on the work by Maerker and coworkers24 and (ii) the second by adipic acid allylation and epoxidation. Polymerization reactions such as that shown for e-aminoca- proic acid (A-B monomer) or adipic acid (A-A monomer) with hexamethylenediamine (B-B monomer) can be written in the general forms, as follows: N0 A-B — A-Bf A-B-}-,v„-2A-B N0 A-A + N0 B-B €* A-ApB-B-A-BdjVo-iB-B where Nn is the number of monomer molecules at the begin- ning of the reaction. Here, 16 different production routes to adipic acid were evaluated using a novel tool for network-embedded thermodynamic analysis of elementary flux modes. 1.5ml C. Procedure: Mix reagents in a 500 mL round bottom flask. The methodology was published by Louis and Mary Fieser in their books. 2.6 million metric tonnes per year of adipic acid is produced from petroleum-derived benzene but current chemical processes operate under harsh conditions (e.g. This is a quantitative reaction that converts a liquid (cyclohexanone) into a solid (adipic acid). For example, humans can only synthesize 11 of the 20 standard amino acids (a.k.a. Adipic acid is the organic compound with the formula (CH2)4(COOH)2. adding two –OH groups to the open valences gives the diacid adipic acid. NIH In this experiment, the oxidative cleavage of cyclohexene will be performed to produce as the only product 1,6-hexanedioic acid (adipic acid), shown in Equation 1 below. x��Y��q��S�K��@:�} @�b�v��id�aP$�8$�%R��|��9�=��s��~]Z]�ˡ�v8�Ӻ.�8O��e��;a�C35MW={U��I=z��z��ɓ�n�'��Y��p�wO?��f�y��4�; ��O�t]�4�׾:�K�$��GP0;�f�n�ô ��&Y��!��*�չ��ڍ�c��CSJ��%��q�.��Ǳm�zn�C4��Y��ɳzh�L��i��V��G�X��`�� In this Video im preparing Adipic acid starting from Cyclohexanol using "green" oxidation. As shown in the Procedure, we will use 2 mL. 1.5 mL C. Procedure: Mix reagents in a 500 mL round bottom flask. 2. << /Length 5 0 R /Filter /FlateDecode >> %PDF-1.3 R 1 = alkyl group; L = leaving group; The group —CH 2 CO 2 H in 2 is contributed by a malonic ester, hence the term malonic ester synthesis. | From the perspective of reaction mechanism, nitrous acid transformed by nitric acid is a crucial reactant involved in the conversion of cyclohexanol and the nitrosation of intermediates. The equations below illustrate the products from cleavage of alkenes: Reaction: HOOQCH^COOH + 2 QHsOH > QHjO-CO^CHJ^CO-OQH; +- 2 H2O B. Reagents: Adipic Acid - 43.8 g, (0.30 mol) Ethanol (95%) - 100 ml Cyclohexane - 30 ml Sulfuric Acid (cone.) Introduction. Lab 7 6 O H H α Step 1 O OH H Step 2 O OH OH Step 3 [O] [O] minus H 2O O O ket one α-h ydr x k et n gem-diol diketone O O diketone [O] Step 4 O HO O OH adipic acid (1,6-hexanedioic acid) Figure 6. Essentially, adipic acid and hexamethylene diamine react together to form a monomer, which is continually reacted with on either side to form a polymer. Synthesis of adipic acid in a microemulsion and recyclability experiments Reactions were carried out in a 0.5 L cylindrical water-jacketed glass reactor equipped with a magnetic stirring bar and a reﬂux condenser. Malonic ester synthesis consists of four consecutive reactions that can be carried out in the same pot. The synthesis is similar to the industrial production of adipic acid wherein a mixture of cyclohexanol and cyclohexanone (called "KA oil) is oxidized with nitric acid to give adipic acid, via a multistep pathway. Can I get some help in figuring out the mechanism for this reaction. Synthesis and Characterization of an Adipic Acid–Derived Epoxy Resin Anthony Maiorana, Bhagyashree Subramaniam, Robert Centore, Xiaorui Han, Robert J. Linhardt, Richard A. 2014), which is shown in Fig. USA.gov. Epub 2018 Sep 25. %�� Quantitative yields (99 %) were achieved for the conversion of mucic acid into muconic acid and adipic acid either in separate sequences or in a one-step process. Get the latest public health information from CDC: https://www.coronavirus.gov, Get the latest research information from NIH: https://www.nih.gov/coronavirus, Find NCBI SARS-CoV-2 literature, sequence, and clinical content: https://www.ncbi.nlm.nih.gov/sars-cov-2/. Traditional feedstock for the synthesis of adipic acid is benzene. of concentrated nitric acid (sp. BenzCl C18 (8.25 g), hydrogen peroxide (30% solution, 132.15 g), sodium tungstate (2.05 g) and sulfuric acid (4.6 g) were added all together. Copper is effective only at higher temperatures where it prevents the further break‐down of unstable intermediates. Adipic acid is one of the most important feedstocks for producing resins, nylons, lubricants, plasticizers. On a balance, tare a small test tube that has been placed in an empty 50 to 100-mL beaker for stabilization. Our main focus is going to be on how adipic acid can be synthesized. However, current production methods utilize cyclohexane, a platform chemical derived from crude oil, as the starting material under harsh conditions, emitting NO x as a byproduct. (��Q%B�F��P'��T��{ cq�u �Rt�3_��NVH��ѿ]��P��e}��>��}��D��"4��r�ݾ��Pu��Y��-\`�X��·~�r٭w�*=o�z��J猷�òଦe>tSa��ͪ��,��s��ű��8-ފ)/yeP8^b�[�ϰ�ə��o]r/\֡ݰ��ju6�c{��qިW|��M*&]�`��˲. Synthesis of Diethyl Adipate A. Bring your solvent product mixture to a boil on your hot plate at your bench. Oxidation Methodology. It is highly desirable to develop sustainable and environmentally friendly processes for the production of adipic acid from renewable feedstocks. Adipic acid is present in some plants and is a chemical in tobacco and tobacco smoke. 2019 Jan 30;9(1):16. doi: 10.1186/s13568-019-0737-1. 2019 Jul 26;20(15):3660. doi: 10.3390/ijms20153660. Facebook. Clipboard, Search History, and several other advanced features are temporarily unavailable. Clean Synthesis of Adipic Acid by Direct Oxidation of Cyclohexene with H 2 O 2 catalysed by Na 2 WO 4 .2H 2 O and Acidic Ionic Liquids. TCC’s Adipic Acid is a mildly toxic, white, crystalline compound. Synthesis of AGA monomer consisted of two steps. A high ω NA is benefit for the enough supply of the nitrous acid, which leads to the formation of AA. Several methods are available including ozonolysis and hot concentrated permanganate. Current industrial petrochemical process, producing adipic acid from KA oil, catalyzed by nitric acid, has a serious pollution to the environment, due to the formation of waste nitrous oxide. Reaction: HOOQCH^COOH + 2 QHsOH > QHjO-CO^CHJ^CO-OQH; +- 2 H2O B. Reagents: Adipic Acid - 43.8 g, (0.30 mol) Ethanol (95%) - 100 ml Cyclohexane - 30 ml Sulfuric Acid (cone.) USE: Adipic acid is a commercially important chemical used during the production of nylon, plastics, lubricants, adhesives, and polyurethane foam. The metabolic pathway producing adipate was proposed based on the analysis of T. fusca pathways by the metabolic model (Vanee et al. density functional calculations; reaction mechanisms; renewable resources; rhenium; sustainable chemistry. /��pܿ� @��7�꡾{i-��{y��;� 1C��5��Ǐ��pO�}:9/�/>�Z��ە�>숽��/F֋珛O\�|�ş��cg�� Identification of adipic acid synthesis pathway. Nitric acid oxidation of cyclohexane accounts for ~95% of the worldwide adipic acid production and is also responsible for ~5 to 8% of the annual worldwide anthropogenic emission of the ozone-depleting greenhouse gas nitrous oxide (N2O). Essentially, adipic acid and hexamethylene diamine react together to form a monomer, which is continually reacted with on either side to form a polymer. Benzene is hydrogenated using Ni-Al2 O 3 catalyst at 370–800 psi to cyclohexane. 2020 Feb 7;13(3):556-563. doi: 10.1002/cssc.201902988. Adipic acid is also used in baking powders instead of … Larson RT, Samant A, Chen J, Lee W, Bohn MA, Ohlmann DM, Zuend SJ, Toste FD. Traditional feedstock for the synthesis of adipic acid is benzene. Production of Hexaric Acids from Biomass. 1.5ml C. Procedure: Mix reagents in a 500 mL round bottom flask. Reddit. 2014;353:163-84. doi: 10.1007/128_2014_537. Early in the reaction, the cyclohexanol is converted to the ketone, releasing nitrous acid: 1.42). 2020 Jul 31;19(1):156. doi: 10.1186/s12934-020-01411-3. For example, epoxidation, dihydroxylation and ozonolysis or oxidative cleavage using potassium permanganate (KMnO 4) of alkenes can all be achieved with the proper choice of reagents. | Engineering marine fungi for conversion of D-galacturonic acid to mucic acid. E210βQ and E210βN enhance adipic acid synthesis. Characterization of diglycidyl adipate by From the simulation results shown in Fig. However, currently there is no suitable bio-adipic acid synthesis process. A method is provided for producing adipic acid. Adipic Acids. Demonstrated herein is the highly efficient synthetic protocol for the conversion of mucic acid into adipic acid through the oxorhenium-complex-catalyzed deoxydehydration (DODH) reaction and subsequent Pt/C-catalyzed transfer hydrogenation. Angew Chem Int Ed Engl. Twitter. This industrial synthesis of adipic acid is detrimental to the environment. Vidgren V, Halinen S, Tamminen A, Olenius S, Wiebe MG. Microb Cell Fact. Synthesis Mechanism and Properties of Epoxy Resins Modified with Adipic Acid 55 a catalyst takes place in two stages. synthesis adipic acid carbon sources derived carbon Prior art date 1993-09-16 Legal status (The legal status is an assumption and is not a legal conclusion. They react in this way with all bases, both organic (for example, the amines) and inorganic. Mechanism. AMB Express. Recrystallize your crude product by placing it in a clean 100 mL beaker and adding 20. mL of a 50% Ethanol-water mixture. Malonic ester synthesis is a synthetic procedure used to convert a compound that has the general structural formula 1 into a carboxylic acid that has the general structural formula 2. Synthesis of adipic acid, a key monomer of nylon-66 and polyurethane, from biomass is highly attractive for establishing green and sustainable chemical processes. Synthesis of Diethyl Adipate A. Top Curr Chem. Adipic acid is one of the most important aliphatic dicarboxylic acids, which is used for the synthesis of Nylon-6,6 polyamide (∼$ 6 billion global market). This site needs JavaScript to work properly. The method comprises the steps of culturing a cell transformant characterized by the constitutive expression of structural genes encoding 3-dehydroshikimate dehydratase, protocatechuate decarboxylase, and catechol 1,2-dioxygenase for a period of time sufficient to convert a carbon source to cis, cis-muconic acid and hydrogenating the cis, … Nylon 6-6 synthesis is an example of a condensation polymerization, as well as a step-growth polymerization. Adipic acid (AA) is a key intermediate in the production of nylon polyurethane and polyester resins, which is also an important link in the chemistry of intermediates for its price and market availability [, , ].Interest in the development of more efficient process has been continuing to inspire researchers to explore new synthesis strategy and resources [, , , , , ]. Experiment 12 Preparation of adipic acid from cyclohexene. The direct synthesis of adipic acid from cyclohexene and hydrogen peroxide by a continuous micro-flow process. Not all organisms are able to synthesize all amino acids. 2013 Aug 20;167(2):75-84. doi: 10.1016/j.jbiotec.2012.07.008. Facebook. Kindly suggest correct mechanism for oxidation of cyclohexanol to adipic acid using HNO3. Synthesis of adipic acid (AA) through the oxidation of cyclohexanol and cyclohexanone (K/A oil) with nitric acid was conducted in a capillary microreactor system. Various adipate diesters were produced in good to excellent yield with high selec-tivity. Procedure 1. gr. The mechanism of diepoxide and adipic acid (AA) reaction in the presence of benzyltriethylammonium chloride and 1,4-diazobicyclo[2,2,2] octane has been proposed. Synthesis of Adipic Acid: On the Way to More Sustainable Production Fabrizio Cavani and Stefano Alini 7.1 Introduction: The Adipic Acid Market Adipic acid (AA) is an important chemical intermediate [1]. Tw��,Gcw��Y�T�¼�Ú�/�"�^j�Ge�/��y�綞��0/�A��!��xj�ދ�jޠ�C�8:Ju Z��A��(=w��h��! Countries should obtain plant-level data on an annual basis. Share . The thermal stability of the oligoester obtained via chemical modification of the dioxydiphenylpropane diglycidyl ether with AA and epoxy-oligoesteric mixtures with its participation has been studied. Adipic acid is produced from a mixture of cyclohexanone and cyclohexanol called KA oil, the abbreviation of ketone-alcohol oil. Twitter. The C6 straight-chain dicarboxylic acid is slightly soluble in water and soluble in alcohol and acetone. Synthesis of Diethyl Adipate A. ChemSusChem. The direct synthesis of adipic acid from cyclohexene and hydrogen peroxide by a continuous micro-flow process Citation for published version (APA): Shang, M. (2016). Microbial hexuronate catabolism in biotechnology. Nylon 6,6- a polymer of adipic acid and 1,6-diaminohexane Adipic acid was commonly obtained by oxidation of castor oil with nitric acid (splitting of the carbon chain close to the OH group), but it is also obtained by oxidation of cyclohexanone or cyclohexene. Please enable it to take advantage of the complete set of features! This video explains synthesis of Adipic Acid by Conventional and Greener Route. Biocatalytic synthesis of adipic acid from glucose eliminates two environmental concerns characteristic of industrial adipic acid manufacture: use of carcinogenic benzene and benzene‐derived chemicals as feedstocks and generation of nitrous oxide as a byproduct of a nitric acid catalyzed oxidation. Amino acid synthesis is the set of biochemical processes (metabolic pathways) by which the amino acids are produced. Without adipic acid, the industrial synthesis of nylon fibers would simply not be practical or even possible. stream Stirring is continued for about one hour after the addition of the last of the cyclohexanol.Then the mixture is cooled to about 0° and the adipic acid is collected on a suction filter, washed with 500 cc. However, the standard route requires large quantities of corrosive nitric acid. A series of copolyanhydrides, consisting of 2,3,4,5-tetra-O-acetylgalactaric acid (AGA) and adipic acid (AA) as monomer units, was polymerized. Adipic acid is a molecule with two carboxylic groups,but I can't see how that happens. The loss in this purification is about 5 per cent. mechanism but a nice way to understand this reaction and other oxidation reactions as well. When cyclohexene and an aqueous solution of sodium tungstate with hydrogen peroxide are mixed, two layers will result and no reaction can occur. R 2 = alkyl, aryl Jan 1974; A. Onopchenko. 2019 Sep 21;55(74):11017-11020. doi: 10.1039/c9cc05413h. Read this document completely, and then answer the prelab questions below. The production of bulk chemicals and fuels from renewable bio-based feedstocks is of significant importance for the sustainability of human society. adipic acid 1,6-diaminohexane H N N H H N O O O O N H Nylon 6,6 Figure 2: Nylon 6,6. Toward biotechnological production of adipic acid and precursors from biorenewables. At any given stage of the reaction, if N Here we report a N2O-free process for adipic acid synthesis. This product is pure enough for most purposes. 4009 Synthesis of adipic acid from cyclohexene HO OH O O + 4 H 2O 2 + 4 H 2O (82.2) (34.0) C 6H 10 + + (404.2) Na 2WO 4 2 H O (329.9) sodium tungstate dihydrate Aliquat 336. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Comment: The authors used kinetic experiments to support the proposed mechanism. Attach the Dean Stark trap and a reflux condenser. Adipic acid and its esters are manufactured on a massive scale, primarily to produce nylon. Heat the mixture under reflux. Synthesis of adipic acid (AA) through the oxidation of cyclohexanol and cyclohexa- none (K/A oil) with nitric acid was conducted in a capillary microreactor system. 2017 Oct 11;139(40):14001-14004. doi: 10.1021/jacs.7b07801. 4009 Synthesis of adipic acid from cyclohexene HO OH O O + 4 H 2O 2 + 4 H 2O (82.2) (34.0) C 6H 10 + + (404.2) Na 2WO 4 2 H O (329.9) sodium tungstate dihydrate Aliquat 336. The total yield of crude adipic acid is 425–440 g. (58–60 per cent of the theoretical amount) (Note 5). J. Yang et al. present an efficient alternative route whereby a palladium catalyst adds carbon monoxide to each end of butadiene (see the Perspective by Schaub). Keywords: 4 0 obj J Am Chem Soc. The specific enzyme activity of E210βN and E210βQ for degrading adipic acid were determined to be 1.95 and 1.84 U/mg, respectively, which compares favorably with the 1.48 U/mg for the wild-type (Fig. 2013 Dec 2;52(49):12905-9. doi: 10.1002/anie.201307564. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.) 2. Almost 90 percent of adipic acid produced is used in the production of nylon 66. The production of Nylon-6,6(forﬁbersandresins)accountsfor63%ofAAconsumption;theﬁbersare National Center for Biotechnology Information, Unable to load your collection due to an error, Unable to load your delegates due to an error. The products obtained depend on the original structure of the olefin. J Biotechnol. The synthesis is similar to the industrial production of adipic acid wherein a mixture of cyclohexanol and cyclohexanone (called "KA oil) is oxidized with nitric acid to give adipic acid, via a multistep pathway. Adipic acid and nitric acid production data are necessary to estimate N2O emissions regardless of the selected estimation method. However, a purer product may be obtained by recrystallizing this crude material from 700 cc. Withdrawn Application number EP94926701A Other languages German (de) French (fr) Other versions EP0722504A1 (en Inventor … Preparation of adipic acid from cyclohexene In this laboratory period the cyclohexene (supposedly) prepared in the previous experiment is oxidized to adipic acid. Zirconia-supported rhenium oxide as an efficient catalyst for the synthesis of biomass-based adipic acid ester. Epub 2019 Aug 19. 11/25/12 fDisadvantage of the synthesis This industrial synthesis of adipic acid is detrimental to the environment. LinkedIn . Synthesis of adipic acid (AA) through the oxidation of cyclohexanol and cyclohexanone (K/A oil) with nitric acid was conducted in a capillary microreactor system. HHS | Synthesis Mechanism and Properties of Epoxy Resins Modified with Adipic Acid @article{Bratychak2019SynthesisMA, title={Synthesis Mechanism and Properties of Epoxy Resins Modified with Adipic Acid}, author={M. Bratychak and B. Bashta and O. Astakhova and O. Shyshchak and Olha Zubal and Prague Czech Republic}, journal={Chemistry and Chemical Technology}, year={2019}, … Expanding the scope of biomass-derived chemicals through tandem reactions based on oxorhenium-catalyzed deoxydehydration. Adipic acid is an important industrial chemical, and approximately 2.5 billion kilograms of this compound are produced each year for the use in the production of the polymer “Nylon 6,6” and is comprised of alternating units of adipic acid and 1,6-diaminohexane. Before coming to the laboratory calculate the amounts of reagents required for the amount of cyclohexene you have available. The substrates for these processes are various compounds in the organism's diet or growth media. Cool this mixture in an ice-water bath and isolate the Adipic acid by vacuum filtration, using your 500 mL filter flask and large buchner funnel. Adipic acid is a monomer for nylon polymers such as polyamide 66. Attach the Dean Stark trap and a reflux condenser. NLM Adipic acid (AA) is a 6-carbon diacid and a building block in the synthesis of Nylon-66. Expt 4: Synthesis of Adipic Acid via Oxidative Cleavage of Cyclohexene INTRODUCTION In CHEM 331, you learned several different ways in which alkenes can be oxidized. My initial thoughts involved that the carbonyl group in cyclohexanone is protonated,but I couldn't get any further as I … COVID-19 is an emerging, rapidly evolving situation. Epub 2019 Dec 30. 17. Adipic acid, a nylon-6,6 precursor, has recently gained popularity in synthetic biology. Epub 2012 Jul 21. Synthesis of Diethyl Adipate Page 2 of 3 Add about an equal amount of ether and extract the mixture three times with aqueous sodium carbonate to remove sulfuric acid and any acidic unreacted adipic acid or any of the half acid ester of adipic acid. ADIPIC ACID is a carboxylic acid. Gross Department of Chemistry and Chemical Biology, New York State Center for Polymer Synthesis, Rensselaer Polytechnic Institute, Troy, New York 12180 Correspondence to: R. A. The tool distinguishes between thermodynamically feasib … Reaction: H+ O H H O O O O HO OH OH O O + + B. Reagents: Adipic Acid - 43.8 g. (0.30 mol) Ethanol (95%) - 100 mL Cyclohexane - 30 mL Sulfuric Acid (conc.) You will be provided with cyclohexene. Int J Mol Sci. Demonstrated herein is the highly efficient synthetic protocol for the conversion of mucic acid into adipic acid through the oxorhenium-complex-catalyzed deoxydehydration (DODH) reaction and subsequent Pt/C-catalyzed transfer hydrogenation. ... Adipic acid synthesis [5] Article. The KA oil is oxidized with nitric acid to give adipic acid, via a multistep pathway. In this laboratory period the cyclohexene prepared in the previous experiment is oxidised to adipic acid. Adipic acid, as one of the most-demanded drop-in chemicals from a bioresource, is used primarily for the large-volume production of nylon-6,6 polyamide. Would you like email updates of new search results? Hydrogen Gas-Mediated Deoxydehydration/Hydrogenation of Sugar Acids: Catalytic Conversion of Glucarates to Adipates. organic chemistry - Mechanism of the reaction of cyclohexanone and nitric acid to form Adipic acid - Chemistry Stack Exchange Mechanism of the reaction of cyclohexanone and nitric acid to … the Synthesis of Adipic Acid Esters Significance: The authors describe a palladium-catalyzed dicarbonylation of 1,3-dienes using car-bon monoxide. Epub 2017 Oct 3. Adipic Acids.