Replacement of Toxic Feedstocks in Chemical Synthesis

Zurück zum Zitat Sartori G, Tundo P (2012) Special topic issue on chlorine free synthesis for green chemistry. Pure Appl Chem 84:411–860CrossRef Sartori G, Tundo P (2012) Special topic issue on chlorine free synthesis for green chemistry. Pure Appl Chem 84:411–860CrossRef

Zurück zum Zitat Cotarca L, Eckert H (2003) Phosgenations – a handbook. Wiley–VCH, WeinheimCrossRef Cotarca L, Eckert H (2003) Phosgenations – a handbook. Wiley–VCH, WeinheimCrossRef

Zurück zum Zitat Tundo P, Musolino M, Aricò F (2018) The reactions of dimethyl carbonate and its derivatives. Green Chem 20:28–85CrossRef Tundo P, Musolino M, Aricò F (2018) The reactions of dimethyl carbonate and its derivatives. Green Chem 20:28–85CrossRef

Zurück zum Zitat Tojo M, Miyaji H (2007) Process for producing dialkyl carbonate and diol. EP1760059B1 Asahi Kasei Chemicals Corp Tojo M, Miyaji H (2007) Process for producing dialkyl carbonate and diol. EP1760059B1 Asahi Kasei Chemicals Corp

Zurück zum Zitat (a) Tundo P, He L-N, Lokteva E, Mota C (2016) Chemistry beyond chlorine. Springer, New York, NY; (b) Garcia-Herrero I, Cuéllar-Franca RM, Enríquez-Gutiérrez VM, Alvarez-Guerra M, Irabien A, Azapagic A (2016) Environmental assessment of dimethyl carbonate production: comparison of a novel electrosynthesis route utilizing CO2 with a commercial oxidative carbonylation process. ACS Sustain Chem Eng 4:2088–2097 (a) Tundo P, He L-N, Lokteva E, Mota C (2016) Chemistry beyond chlorine. Springer, New York, NY; (b) Garcia-Herrero I, Cuéllar-Franca RM, Enríquez-Gutiérrez VM, Alvarez-Guerra M, Irabien A, Azapagic A (2016) Environmental assessment of dimethyl carbonate production: comparison of a novel electrosynthesis route utilizing CO₂ with a commercial oxidative carbonylation process. ACS Sustain Chem Eng 4:2088–2097

Zurück zum Zitat Arico F, Tundo P (2010) Dimethyl carbonate: a modern green reagent and solvent. Russ Chem Rev 79:479–489CrossRef Arico F, Tundo P (2010) Dimethyl carbonate: a modern green reagent and solvent. Russ Chem Rev 79:479–489CrossRef

Zurück zum Zitat (a) Musolino M, Andraos J, Aricò F (2018) An easy scalable approach to HMF employing DMC as reaction media: reaction optimization and comparative environmental assessment. ChemistrySelect 3:2359–2365; (b) Aricò F, Maranzana A, Musolino M, Tundo P (2018) 5-membered cyclic ethers via phenonium ion mediated cyclization through carbonate chemistry. Pure Appl Chem 90:93–107; (c) Aricò F, Aldoshin AS, Musolino M, Crisma M, Tundo P (2018) β–aminocarbonates in regioselective and ring expansion reactions. J Org Chem 83:236–243; (d) Aricò F, Bravo S, Crisma M, Tundo P (2016) 1,3-Oxazinan-2-ones via carbonate chemistry: a facile, high yielding synthetic approach. Pure Appl Chem 88:227–237; (e) Aricò F, Udrea I, Crisma M, Tundo P (2015) Azacrown ethers from mustard carbonate analogues. ChemPlusChem 80:471–474; (f) Aricò F, Evaristo S, Tundo P (2015) Synthesis of five- and six-membered heterocycles by dimethyl carbonate with catalytic amounts of nitrogen bicyclic bases. Green Chem 17:1176–1185; (g) Toniolo S, Aricò F, Tundo P (2014) A comparative environmental assessment for the synthesis of 1,3-Oxazin-2-one by metrics: greenness evaluation and blind spots. ACS Sustain Chem Eng 2:1056–1062; (h) Aricò F, Tundo P (2012) Dimethyl carbonate as a sacrificial molecule for the synthesis of 5-memebered N– and O–heterocycles. J Chin Chem Soc 59:1375–1384; (i) McElroy CR, Aricò F, Tundo P (2012) 1,3-Oxazinan-2-ones from amines and 1,3-diols through dialkyl carbonate chemistry. Synlett 23:1809–1815; (j) Aricò F, Toniolo U, Tundo P (2012) 5-membered N-heterocyclic compounds by dimethyl carbonate chemistry. Green Chem 14:58–61; (k) McElroy CR, Aricò F, Benetollo F, Tundo P (2012) Cyclization reaction of amines with dialkyl carbonates to yield 1,3-oxazinan-2-ones. Pure Appl Chem 84:707–719; (l) Aricò F, Tundo P (2012) Dimethyl carbonate as a sacrificial molecule for the synthesis of 5–memebered N– and O–heterocycles. J Chin Chem Soc 59:1375–1384; (m) Aricò F, Tundo P, Maranzana A, Tonachini G (2012) 5-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate. ChemSusChem 5:1578–1586 (a) Musolino M, Andraos J, Aricò F (2018) An easy scalable approach to HMF employing DMC as reaction media: reaction optimization and comparative environmental assessment. ChemistrySelect 3:2359–2365; (b) Aricò F, Maranzana A, Musolino M, Tundo P (2018) 5-membered cyclic ethers via phenonium ion mediated cyclization through carbonate chemistry. Pure Appl Chem 90:93–107; (c) Aricò F, Aldoshin AS, Musolino M, Crisma M, Tundo P (2018) β–aminocarbonates in regioselective and ring expansion reactions. J Org Chem 83:236–243; (d) Aricò F, Bravo S, Crisma M, Tundo P (2016) 1,3-Oxazinan-2-ones via carbonate chemistry: a facile, high yielding synthetic approach. Pure Appl Chem 88:227–237; (e) Aricò F, Udrea I, Crisma M, Tundo P (2015) Azacrown ethers from mustard carbonate analogues. ChemPlusChem 80:471–474; (f) Aricò F, Evaristo S, Tundo P (2015) Synthesis of five- and six-membered heterocycles by dimethyl carbonate with catalytic amounts of nitrogen bicyclic bases. Green Chem 17:1176–1185; (g) Toniolo S, Aricò F, Tundo P (2014) A comparative environmental assessment for the synthesis of 1,3-Oxazin-2-one by metrics: greenness evaluation and blind spots. ACS Sustain Chem Eng 2:1056–1062; (h) Aricò F, Tundo P (2012) Dimethyl carbonate as a sacrificial molecule for the synthesis of 5-memebered N– and O–heterocycles. J Chin Chem Soc 59:1375–1384; (i) McElroy CR, Aricò F, Tundo P (2012) 1,3-Oxazinan-2-ones from amines and 1,3-diols through dialkyl carbonate chemistry. Synlett 23:1809–1815; (j) Aricò F, Toniolo U, Tundo P (2012) 5-membered N-heterocyclic compounds by dimethyl carbonate chemistry. Green Chem 14:58–61; (k) McElroy CR, Aricò F, Benetollo F, Tundo P (2012) Cyclization reaction of amines with dialkyl carbonates to yield 1,3-oxazinan-2-ones. Pure Appl Chem 84:707–719; (l) Aricò F, Tundo P (2012) Dimethyl carbonate as a sacrificial molecule for the synthesis of 5–memebered N– and O–heterocycles. J Chin Chem Soc 59:1375–1384; (m) Aricò F, Tundo P, Maranzana A, Tonachini G (2012) 5-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate. ChemSusChem 5:1578–1586

Zurück zum Zitat (a) Tundo P, Bressanello S, Loris A, Sathicq G (2005) Direct synthesis of N-methylurethanes from primary amines with dimethyl carbonates. Pure Appl Chem 77:1719–1725; (b) Mertes H, Wilmes O, Nachtkamp K, Dahmer J, Meyn J (1995) Prodn. of 1,4-butylene di:isocyanate from 1,4-butane-di:amine. DE 4413580 Bayer A.G (a) Tundo P, Bressanello S, Loris A, Sathicq G (2005) Direct synthesis of N-methylurethanes from primary amines with dimethyl carbonates. Pure Appl Chem 77:1719–1725; (b) Mertes H, Wilmes O, Nachtkamp K, Dahmer J, Meyn J (1995) Prodn. of 1,4-butylene di:isocyanate from 1,4-butane-di:amine. DE 4413580 Bayer A.G

Zurück zum Zitat Tundo P, Aricò F, Rosamilia A, Grego S, Rossi L (2008) Dimethyl carbonate: green solvent and Ambidentreagent. Green Chem React 206:201–220 Tundo P, Aricò F, Rosamilia A, Grego S, Rossi L (2008) Dimethyl carbonate: green solvent and Ambidentreagent. Green Chem React 206:201–220

Zurück zum Zitat Porta E, Cenni S, Pizzotti M, Crotti C (1985) Gazz Chim Ital 115:275 Porta E, Cenni S, Pizzotti M, Crotti C (1985) Gazz Chim Ital 115:275

Zurück zum Zitat Curini M, Epifano F, Maltese F, Rosati O (2002) Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis. Tetrahedron Lett 43:4895–4897CrossRef Curini M, Epifano F, Maltese F, Rosati O (2002) Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis. Tetrahedron Lett 43:4895–4897CrossRef

Zurück zum Zitat Distaso M, Quaranta E (2004) Group 3 metal (Sc, La) triflates as catalysts for the carbomethoxylation of aliphatic amines with dimethylcarbonate under mild conditions. Tetrahedron 60:1531–1539CrossRef Distaso M, Quaranta E (2004) Group 3 metal (Sc, La) triflates as catalysts for the carbomethoxylation of aliphatic amines with dimethylcarbonate under mild conditions. Tetrahedron 60:1531–1539CrossRef

Zurück zum Zitat Han C, Porco JA (2007) Synthesis of carbamates and ureas using Zr(IV)-catalyzed exchange processes. Org Lett 9:1517–1520CrossRef Han C, Porco JA (2007) Synthesis of carbamates and ureas using Zr(IV)-catalyzed exchange processes. Org Lett 9:1517–1520CrossRef

Zurück zum Zitat For reports on Ti–(IV)–catalyzed transamidation, see: (a) Eldred S E, Stone D A, Gellman S H, Stahl S S (2003) Catalytic transamidation under moderate conditions. J Am Chem Soc 125:3422–3423; (b) Kissounko DA, Hoerter JM, Guzei IA, Cui Q, Gellman SH, Stahl SS (2007) TiIV-mediated reactions between primary amines and secondary carboxamides: amidine formation versus transamidation. J Am Chem Soc 129:1776–1783 For reports on Ti–(IV)–catalyzed transamidation, see: (a) Eldred S E, Stone D A, Gellman S H, Stahl S S (2003) Catalytic transamidation under moderate conditions. J Am Chem Soc 125:3422–3423; (b) Kissounko DA, Hoerter JM, Guzei IA, Cui Q, Gellman SH, Stahl SS (2007) Ti^IV-mediated reactions between primary amines and secondary carboxamides: amidine formation versus transamidation. J Am Chem Soc 129:1776–1783

Zurück zum Zitat Han C, Lee JP, Lobkovsky E, Porco JAJ (2005) Catalytic ester-amide exchange using group (IV) metal Alkoxide-activator complexes. J Am Chem Soc 127:10039–11044CrossRef Han C, Lee JP, Lobkovsky E, Porco JAJ (2005) Catalytic ester-amide exchange using group (IV) metal Alkoxide-activator complexes. J Am Chem Soc 127:10039–11044CrossRef

Zurück zum Zitat (a) Aresta M, Quaranta E (1991) Mechanistic studies on the role of carbon dioxide in the synthesis of methylcarbamates from amines and dimethylcarbonate in the presence of CO2. Tetrahedron 47:9489; (b) Aresta M, Dibenedetto A, Quaranta E, Boscolo M, Larrson R (2001) The kinetics and mechanism of the reaction between carbon dioxide and a series of amines: observation and interpretation of an isokinetic effect. J Mol Catal 174:7–13 (a) Aresta M, Quaranta E (1991) Mechanistic studies on the role of carbon dioxide in the synthesis of methylcarbamates from amines and dimethylcarbonate in the presence of CO₂. Tetrahedron 47:9489; (b) Aresta M, Dibenedetto A, Quaranta E, Boscolo M, Larrson R (2001) The kinetics and mechanism of the reaction between carbon dioxide and a series of amines: observation and interpretation of an isokinetic effect. J Mol Catal 174:7–13

Zurück zum Zitat Selva M, Tundo P, Perosa A (2002) The synthesis of alkyl carbamates from primary aliphatic amines and dialkyl carbonates in supercritical carbon dioxide. Tetrahedron Lett 43:1217–1219CrossRef Selva M, Tundo P, Perosa A (2002) The synthesis of alkyl carbamates from primary aliphatic amines and dialkyl carbonates in supercritical carbon dioxide. Tetrahedron Lett 43:1217–1219CrossRef

Zurück zum Zitat Juárez R, Corma A, García A (2012) Activity of ceria and ceria–supported gold nanoparticles for the carbamoylation of aliphatic amines by dimethyl carbonate. Pure Appl Chem 84:685–694CrossRef Juárez R, Corma A, García A (2012) Activity of ceria and ceria–supported gold nanoparticles for the carbamoylation of aliphatic amines by dimethyl carbonate. Pure Appl Chem 84:685–694CrossRef

Zurück zum Zitat Carloni S, De Vos DE, Jacobs PA, Maggi R, Sartori G, Sartorio R (2002) Catalytic activity of MCM-41–TBD in the selective preparation of carbamates and unsymmetrical alkyl carbonates from diethyl carbonate. J Cat 205:199–204CrossRef Carloni S, De Vos DE, Jacobs PA, Maggi R, Sartori G, Sartorio R (2002) Catalytic activity of MCM-41–TBD in the selective preparation of carbamates and unsymmetrical alkyl carbonates from diethyl carbonate. J Cat 205:199–204CrossRef

Zurück zum Zitat (a) Barcelo G, Grenouillat D, Senet J-P, Sennyey G (1990) Pentaalkylguanidines as etherification and esterification catalysts. Tetrahedron 46:1839–1848; (b) Rao SYV, De Vos DE, Jacobs PA (1997) 1,5,7-Triazabicyclo[4.4.0]dec-5-ene immobilized in MCM-41: a strongly basic porous catalyst. Angew Chem Int Ed Engl 36:2661–2663; (c) Blanc A, Macquarrie DJ, Valle S, Renard G, Quinn CR, Brunel D (2000) The preparation and use of novel immobilised guanidine catalysts in base-catalysed epoxidation and condensation reactions. Green Chem 2:283–288 (a) Barcelo G, Grenouillat D, Senet J-P, Sennyey G (1990) Pentaalkylguanidines as etherification and esterification catalysts. Tetrahedron 46:1839–1848; (b) Rao SYV, De Vos DE, Jacobs PA (1997) 1,5,7-Triazabicyclo[4.4.0]dec-5-ene immobilized in MCM-41: a strongly basic porous catalyst. Angew Chem Int Ed Engl 36:2661–2663; (c) Blanc A, Macquarrie DJ, Valle S, Renard G, Quinn CR, Brunel D (2000) The preparation and use of novel immobilised guanidine catalysts in base-catalysed epoxidation and condensation reactions. Green Chem 2:283–288

Zurück zum Zitat Dunetz JR, Ciccolini RP, Froling M, Paap SM, Allen AJ, Holmes AB, Tester JW, Danheiser RL (2005) Pictet–Spengler reactions in multiphasic supercritical carbon dioxide/CO2-expanded liquid media. In situ generation of carbamates as a strategy for reactions of amines in supercritical carbon dioxide. Chem Commun 0:4465–4467CrossRef Dunetz JR, Ciccolini RP, Froling M, Paap SM, Allen AJ, Holmes AB, Tester JW, Danheiser RL (2005) Pictet–Spengler reactions in multiphasic supercritical carbon dioxide/CO₂-expanded liquid media. In situ generation of carbamates as a strategy for reactions of amines in supercritical carbon dioxide. Chem Commun 0:4465–4467CrossRef

Zurück zum Zitat Tundo P, McElroy CR, Aricò F, Rigo M (2010) Carbamates from reactions of amines with dialkylcarbonates: a study of leaving and entering groups. Synlett 10:1567–1571CrossRef Tundo P, McElroy CR, Aricò F, Rigo M (2010) Carbamates from reactions of amines with dialkylcarbonates: a study of leaving and entering groups. Synlett 10:1567–1571CrossRef

Zurück zum Zitat Zeng R, Bao L, Sheng H, Sun L, Chen M, Feng Y, Zhu M (2016) Heterobimetallic dinuclear lanthanide alkoxide complexes as acid-base bifunctional catalysts for synthesis of carbamates under solvent–free conditions. RSC Adv 6:78576–78584CrossRef Zeng R, Bao L, Sheng H, Sun L, Chen M, Feng Y, Zhu M (2016) Heterobimetallic dinuclear lanthanide alkoxide complexes as acid-base bifunctional catalysts for synthesis of carbamates under solvent–free conditions. RSC Adv 6:78576–78584CrossRef

Zurück zum Zitat Distaso M, Quaranta E (2006) Highly selective carbamation of aliphatic diamines under mild conditions using Sc(OTf)3 as catalyst and dimethyl carbonate as a phosgene substitute. Appl Catal B Environ 66:72–80CrossRef Distaso M, Quaranta E (2006) Highly selective carbamation of aliphatic diamines under mild conditions using Sc(OTf)₃ as catalyst and dimethyl carbonate as a phosgene substitute. Appl Catal B Environ 66:72–80CrossRef

Zurück zum Zitat Distaso M, Quaranta E (2008) Sc(OTf)3-catalyzed carbomethoxylation of aliphatic amines with dimethyl carbonate (DMC): DMC activation by η1-O (CO) coordination to Sc (III) and its relevance to catalysis. J Catal 253:278–288CrossRef Distaso M, Quaranta E (2008) Sc(OTf)₃-catalyzed carbomethoxylation of aliphatic amines with dimethyl carbonate (DMC): DMC activation by η1-O (CO) coordination to Sc (III) and its relevance to catalysis. J Catal 253:278–288CrossRef

Zurück zum Zitat Deleon RG, Kobayashi A, Yamauchi T, Ooishi J, Baba T, Sasaki M, Hiarata F (2002) Catalytic Methoxycarbonylation of 1,6-hexanediamine with dimethyl carbonate to Dimethylhexane-1,6-dicarbamate using bi(NO3)3. Appl Catal A Gen 225:43–49CrossRef Deleon RG, Kobayashi A, Yamauchi T, Ooishi J, Baba T, Sasaki M, Hiarata F (2002) Catalytic Methoxycarbonylation of 1,6-hexanediamine with dimethyl carbonate to Dimethylhexane-1,6-dicarbamate using bi(NO₃)₃. Appl Catal A Gen 225:43–49CrossRef

Zurück zum Zitat Li H-Q, Cao Y, Li X-T, Wang L-G, Li F-J, Zhu GY (2014) Heterogeneous catalytic methoxycarbonylation of 1,6-Hexanediamine by dimethyl carbonate to dimethylhexane-1,6-dicarbamate. Ind Eng Chem Res 53:626–634CrossRef Li H-Q, Cao Y, Li X-T, Wang L-G, Li F-J, Zhu GY (2014) Heterogeneous catalytic methoxycarbonylation of 1,6-Hexanediamine by dimethyl carbonate to dimethylhexane-1,6-dicarbamate. Ind Eng Chem Res 53:626–634CrossRef

Zurück zum Zitat (a) Vauthey I, Falot V, Gozzi C, Fache F, Lemaire M (2000) An environmentally benign access to carbamates and ureas. Tetrahedron Lett 41:6347–6350; (b) Baba T, Fujiwara M, Oosaku A, Kobayashi A, Deleon RG, Ono Y (2002) Catalytic synthesis of N-alkyl carbamates by methoxycaronylation of alkylamines with dimethyl carbonate using Pb(NO3)2. Appl Catal A Gen 227:1–6 (a) Vauthey I, Falot V, Gozzi C, Fache F, Lemaire M (2000) An environmentally benign access to carbamates and ureas. Tetrahedron Lett 41:6347–6350; (b) Baba T, Fujiwara M, Oosaku A, Kobayashi A, Deleon RG, Ono Y (2002) Catalytic synthesis of N-alkyl carbamates by methoxycaronylation of alkylamines with dimethyl carbonate using Pb(NO₃)₂. Appl Catal A Gen 227:1–6

Zurück zum Zitat Wang P, Fei Y, Li Q, Deng Y (2016) Effective synthesis of dimethylhexane-1,6-dicarbamate from 1,6-hexanediamine and dimethyl carbonate using 3-amino-1,2,4-triazole potassium as a solid base catalyst at ambient temperature. Green Chem 18:6681–6686CrossRef Wang P, Fei Y, Li Q, Deng Y (2016) Effective synthesis of dimethylhexane-1,6-dicarbamate from 1,6-hexanediamine and dimethyl carbonate using 3-amino-1,2,4-triazole potassium as a solid base catalyst at ambient temperature. Green Chem 18:6681–6686CrossRef

Zurück zum Zitat Belfadhel HA, Brack H-P, Godoy-Lopez R, Willemse DJPM (2010) Method for making carbamates, ureas and isocyanates. US2010113819 Sabic Innovative Plastics Belfadhel HA, Brack H-P, Godoy-Lopez R, Willemse DJPM (2010) Method for making carbamates, ureas and isocyanates. US2010113819 Sabic Innovative Plastics

Zurück zum Zitat (a) Gupte SP, Shivarkar AB, Chaudhari RV (2001) Carbamate synthesis by solid-base catalyzed reaction of disubstituted ureas and carbonates. Chem Commun 0:2620–2621; (b) Gupte SP, Chaudari RV, Anandkumar BS, Mulla SA (2005) Process for preparing carbamates. WO2005063698 Council of Scientific & Industrial Research (a) Gupte SP, Shivarkar AB, Chaudhari RV (2001) Carbamate synthesis by solid-base catalyzed reaction of disubstituted ureas and carbonates. Chem Commun 0:2620–2621; (b) Gupte SP, Chaudari RV, Anandkumar BS, Mulla SA (2005) Process for preparing carbamates. WO2005063698 Council of Scientific & Industrial Research

Zurück zum Zitat Schweitzer C (1944) Chemical process and products. US2409712 Du Pont de Nemours & Co. Schweitzer C (1944) Chemical process and products. US2409712 Du Pont de Nemours & Co.

Zurück zum Zitat (a) Kim H S, Kim H, Oh J Y, Shin S, Kim S S, Lim K S, Choi J D (2014) Method for Preparing aliphatic diisocyanate. University-Industry Cooperation Group of Kyung Hee University US2014303399; (b) Shinohata M, Miyake N (2009) Process for producing isocyanate. EP2088138 Asahi Kasei Chemicals Corporation; (c) Shinohata M, Miyake N (2010) Method for production of isocyanate using composition comprising carbamic acid ester and aromatic hydroxy compound, and composition for transport or storage of carbamic acid ester. EP2147909 Asahi Kasei Chemicals Corporation (a) Kim H S, Kim H, Oh J Y, Shin S, Kim S S, Lim K S, Choi J D (2014) Method for Preparing aliphatic diisocyanate. University-Industry Cooperation Group of Kyung Hee University US2014303399; (b) Shinohata M, Miyake N (2009) Process for producing isocyanate. EP2088138 Asahi Kasei Chemicals Corporation; (c) Shinohata M, Miyake N (2010) Method for production of isocyanate using composition comprising carbamic acid ester and aromatic hydroxy compound, and composition for transport or storage of carbamic acid ester. EP2147909 Asahi Kasei Chemicals Corporation

Zurück zum Zitat (a) Cui M, Chen X, Yang Y, Tang J, Qiao X, Fei Z (2016) Synthetic method of isophorone diamino methyl formate. CN103980160 Nanjing University of Technology; (b) Yamamoto Y, Yoshida Y, Araki M (2012) Process for preparing a carbamate compound US2012302782; (c) Suzuki K, Araki M, Yoshida Y (2015) Method for producing a carbamate compound. CN104837813 Ube Industries Ltd. (a) Cui M, Chen X, Yang Y, Tang J, Qiao X, Fei Z (2016) Synthetic method of isophorone diamino methyl formate. CN103980160 Nanjing University of Technology; (b) Yamamoto Y, Yoshida Y, Araki M (2012) Process for preparing a carbamate compound US2012302782; (c) Suzuki K, Araki M, Yoshida Y (2015) Method for producing a carbamate compound. CN104837813 Ube Industries Ltd.

Zurück zum Zitat Kumar S, Jain SL (2013) L-Proline-TBAB-catalyzed phosgene free synthesis of methyl carbamates from amines and dimethyl carbonate. New J Chem 37:2935–2938CrossRef Kumar S, Jain SL (2013) L-Proline-TBAB-catalyzed phosgene free synthesis of methyl carbamates from amines and dimethyl carbonate. New J Chem 37:2935–2938CrossRef

Zurück zum Zitat Deng Y, Guo X, Shi F, Zhang Q, Ma X, Lu L, Li J, Tian X, Ma Y, Shang J, Cui X, Wang LL, Zhang H (2011) Method for preparing isocyanates by liquid-phase thermal cracking. US2011/21810 Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences Deng Y, Guo X, Shi F, Zhang Q, Ma X, Lu L, Li J, Tian X, Ma Y, Shang J, Cui X, Wang LL, Zhang H (2011) Method for preparing isocyanates by liquid-phase thermal cracking. US2011/21810 Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences

Zurück zum Zitat Grego S, Aricò F, Tundo P (2012) Highly selective phosgene-free carbamoylation of aniline by dimethyl carbonate under continuous-flow conditions. Pure Appl Chem 84(3):695–705CrossRef Grego S, Aricò F, Tundo P (2012) Highly selective phosgene-free carbamoylation of aniline by dimethyl carbonate under continuous-flow conditions. Pure Appl Chem 84(3):695–705CrossRef

Zurück zum Zitat Fu Z-H, Ono Y (1994) Synthesis of methyl N-phenyl carbamate by methoxycarbonylation of aniline with dimethyl carbonate using Pb compounds as catalysts. J Mol Catal 91:399–405CrossRef Fu Z-H, Ono Y (1994) Synthesis of methyl N-phenyl carbamate by methoxycarbonylation of aniline with dimethyl carbonate using Pb compounds as catalysts. J Mol Catal 91:399–405CrossRef

Zurück zum Zitat Ono Y (1997) Catalysis in the production and reactions of dimethyl carbonate, an environmentally benign building block. Appl Catal A Gen 155:133–166CrossRef Ono Y (1997) Catalysis in the production and reactions of dimethyl carbonate, an environmentally benign building block. Appl Catal A Gen 155:133–166CrossRef

Zurück zum Zitat (a) Zhao X, Wang Y, Wang S, Yang H, Zhang J (2002) Synthesis of MDI from dimethyl carbonate over solid catalysts. Ind Eng Chem Res 41:5139–5144; (b) Wang Y, Zhao X, Li F, Wang S, Zhang J (2001) Catalytic synthesis of toluene-2,4-diisocyanate from dimethyl carbonate. J Chem Technol Biotechnol 76:857–861; (c) Juarez R, Conception P, Corma A, Fornes V, Garcia H (2010) Gold–catalyzed phosgene–free synthesis of polyurethane precursors. Angew Chem Int Ed 49:1286–1290 (a) Zhao X, Wang Y, Wang S, Yang H, Zhang J (2002) Synthesis of MDI from dimethyl carbonate over solid catalysts. Ind Eng Chem Res 41:5139–5144; (b) Wang Y, Zhao X, Li F, Wang S, Zhang J (2001) Catalytic synthesis of toluene-2,4-diisocyanate from dimethyl carbonate. J Chem Technol Biotechnol 76:857–861; (c) Juarez R, Conception P, Corma A, Fornes V, Garcia H (2010) Gold–catalyzed phosgene–free synthesis of polyurethane precursors. Angew Chem Int Ed 49:1286–1290

Zurück zum Zitat Grego S, Aricò F, Tundo P (2013) Highly selective phosgene-free carbamoylation of aniline by dimethyl carbonate under continuous-flow conditions. Org Process Res Dev 17:679–683CrossRef Grego S, Aricò F, Tundo P (2013) Highly selective phosgene-free carbamoylation of aniline by dimethyl carbonate under continuous-flow conditions. Org Process Res Dev 17:679–683CrossRef

Zurück zum Zitat Tundo P, Grego S, Rigo M, Paludetto R (2009) Process for the production of aromatic urethanes. EP 2199278A1 Tundo P, Grego S, Rigo M, Paludetto R (2009) Process for the production of aromatic urethanes. EP 2199278A1

Zurück zum Zitat Matsunaga F, Yasuhara M (1992) Method of condensing N-phenyl carbamates. EP0410684 Matsunaga F, Yasuhara M (1992) Method of condensing N-phenyl carbamates. EP0410684

Zurück zum Zitat Clerici G M, Bellussi G, Romano U (1993) Process for preparation of 4,4′-diaminodiphenyl-methane and its derivatives. US5241119 Clerici G M, Bellussi G, Romano U (1993) Process for preparation of 4,4′-diaminodiphenyl-methane and its derivatives. US5241119

Zurück zum Zitat Sundermann R, Konig K, Engbert T, Becher G, Hammen G (1983) Process for the preparation of polyisocyanates. US4388246 Sundermann R, Konig K, Engbert T, Becher G, Hammen G (1983) Process for the preparation of polyisocyanates. US4388246

Zurück zum Zitat Qiu Z, Wang J, Kang M, Li Q, Wang X (2008) Formation of intermediate and by-products in synthesis of 4,4′-methylenedimethyldiphenylcarbamate. Catal Lett 124:243–247CrossRef Qiu Z, Wang J, Kang M, Li Q, Wang X (2008) Formation of intermediate and by-products in synthesis of 4,4′-methylenedimethyldiphenylcarbamate. Catal Lett 124:243–247CrossRef

Zurück zum Zitat (a) Shinohata M, Miyake N (2011) Process for producing isocyanate using diaryl carbonate. EP2275405 Asahi Kasei Chemicals Corporation; (b) Shinohata M, Miyake N (2011) Process for producing isocyanate using Diaryl carbonate. US2011054211 Asahi Kasei Chemicals Corporation (a) Shinohata M, Miyake N (2011) Process for producing isocyanate using diaryl carbonate. EP2275405 Asahi Kasei Chemicals Corporation; (b) Shinohata M, Miyake N (2011) Process for producing isocyanate using Diaryl carbonate. US2011054211 Asahi Kasei Chemicals Corporation

Zurück zum Zitat Baba T, Kobayashi A, Yamauchi T, Tanaka H, Aso S, Inomata M, Kawanami Y (2002) Catalytic methoxycarbonylation of aromatic diamines with dimethyl carbonate to their dicarbamates using zinc acetate. Catal Lett 82:193–197CrossRef Baba T, Kobayashi A, Yamauchi T, Tanaka H, Aso S, Inomata M, Kawanami Y (2002) Catalytic methoxycarbonylation of aromatic diamines with dimethyl carbonate to their dicarbamates using zinc acetate. Catal Lett 82:193–197CrossRef

Zurück zum Zitat Juarez R, Padilla A, Corma A, Garcıa H (2008) Organocatalysts for the reaction of dimethyl carbonate with 2,4-Diaminotoluene. Ind Eng Chem Res 47:8043–8047CrossRef Juarez R, Padilla A, Corma A, Garcıa H (2008) Organocatalysts for the reaction of dimethyl carbonate with 2,4-Diaminotoluene. Ind Eng Chem Res 47:8043–8047CrossRef

Zurück zum Zitat (a) Simon L, Goodman JM (2007) The mechanism of TBD-catalyzed ring opening polymerization of cyclic esters. J Org Chem 72:9656–9662; (b) Pratt RC, Lohmeijer BGG, Long DA, Waymouth RM, Hedrick JL (2006) Triazabicyclodecene: a simple bifunctional organocatalyst for acyl transfer and ring-opening polymerization of cyclic esters. J Am Chem Soc 128:4556–4557 (a) Simon L, Goodman JM (2007) The mechanism of TBD-catalyzed ring opening polymerization of cyclic esters. J Org Chem 72:9656–9662; (b) Pratt RC, Lohmeijer BGG, Long DA, Waymouth RM, Hedrick JL (2006) Triazabicyclodecene: a simple bifunctional organocatalyst for acyl transfer and ring-opening polymerization of cyclic esters. J Am Chem Soc 128:4556–4557

Zurück zum Zitat (a) Mukherjee S, Yang JW, Hoffmann S, List B (2007) Asymmetric enamine catalysis. Chem Rev 107:5471–5569; (b) Chen XH, Luo SW, Tang Z, Cun LF, Mi AQ, Jiang YZ, Gong LZ (2007) Chem Eur J 13:689–701; (c) Limbach M (2005) ‘Five at one stroke’: proline and small peptides in the stereoselective de novo synthesis and enantiotopic functionalization of carbohydrates. Chem Biodivers 2:825–836 (a) Mukherjee S, Yang JW, Hoffmann S, List B (2007) Asymmetric enamine catalysis. Chem Rev 107:5471–5569; (b) Chen XH, Luo SW, Tang Z, Cun LF, Mi AQ, Jiang YZ, Gong LZ (2007) Chem Eur J 13:689–701; (c) Limbach M (2005) ‘Five at one stroke’: proline and small peptides in the stereoselective de novo synthesis and enantiotopic functionalization of carbohydrates. Chem Biodivers 2:825–836

Zurück zum Zitat Aresta M, Dibenedetto A, Quaranta E (1998) Reaction of aromatic diamines with diphenyl carbonate catalyzed by phosphorus acids: a new clean synthetic route to mono- and dicarbamates. Tetrahedron 54:14145–14156CrossRef Aresta M, Dibenedetto A, Quaranta E (1998) Reaction of aromatic diamines with diphenyl carbonate catalyzed by phosphorus acids: a new clean synthetic route to mono- and dicarbamates. Tetrahedron 54:14145–14156CrossRef

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Zurück zum Zitat (a) Rosamilia AE, Aricò F, Tundo P (2008) Reaction of the ambident electrophile dimethyl carbonate with the ambident nucleophile phenylhydrazine. J Org Chem 73:1559–1562; (b) Rosamilia AE, Aricò F, Tundo P (2008) Insight into the hard−soft acid−base properties of differently substituted phenylhydrazines in reactions with dimethyl carbonate. J Phys Chem B 112:14525–14529 (a) Rosamilia AE, Aricò F, Tundo P (2008) Reaction of the ambident electrophile dimethyl carbonate with the ambident nucleophile phenylhydrazine. J Org Chem 73:1559–1562; (b) Rosamilia AE, Aricò F, Tundo P (2008) Insight into the hard−soft acid−base properties of differently substituted phenylhydrazines in reactions with dimethyl carbonate. J Phys Chem B 112:14525–14529

Zurück zum Zitat Carafa M, Distaso M, Mele V, Trani F, Quaranta E (2008) Superbase-promoted direct N-carbonylation of pyrrole with carbonic acid diesters. Tetrahedron Lett 49:3691–3696CrossRef Carafa M, Distaso M, Mele V, Trani F, Quaranta E (2008) Superbase-promoted direct N-carbonylation of pyrrole with carbonic acid diesters. Tetrahedron Lett 49:3691–3696CrossRef

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Zurück zum Zitat (a) Voit BI, Lederer A (2009) Hyperbranched and highly branched polymer architectures – synthetic strategies and major characterization aspects. Chem Rev 109:5924–5973; (b) Kreye O, Mutlu H, Meier MAR (2013) Sustainable routes to polyurethane precursors. Green Chem 15:1431–1435 (a) Voit BI, Lederer A (2009) Hyperbranched and highly branched polymer architectures – synthetic strategies and major characterization aspects. Chem Rev 109:5924–5973; (b) Kreye O, Mutlu H, Meier MAR (2013) Sustainable routes to polyurethane precursors. Green Chem 15:1431–1435

Zurück zum Zitat (a) Murdock KC (1968) 2-Oxazolidinones from an N-dealkylation reaction of phosgene with dialkylaminoalkanols. Isolation and reactivities of an N-acyl quaternary ammonium intermediate. J Org Chem 33:1367–1371; (b) Trifunovic S, Dimitrijevic D, Vasic G, Vukicevic RD, Radulovic N, Vukicevic M, Heinemann FW (2010) New simple synthesis of N-substituted 1,3-oxazinan-2-ones. Synthesis 6:943–946; (c) Shibata I, Nakamura K, Baba A, Matsuda H (1989) Formation of N-Tributylstannyl heterocycle from bis(tributyltin) oxide and ω-haloalkyl isocyanate. One-pot convenient synthesis of 2-oxazolidinones and tetrahydro-2H-1,3-oxazin-2-one. Bull Chem Soc Jpn 62:853–859; (d) Mangelinckx S, Nural Y, Dondas HA, Denolf B, Sillanpaa R, De Kimpe N (2010) Diastereoselective synthesis of 6-functionalized 4-aryl-1,3-oxazinan-2-ones and their application in the synthesis of 3-aryl-1,3-aminoalcohols and 6-arylpiperidine-2,4-diones. Tetrahedron 66:4115–4124 (a) Murdock KC (1968) 2-Oxazolidinones from an N-dealkylation reaction of phosgene with dialkylaminoalkanols. Isolation and reactivities of an N-acyl quaternary ammonium intermediate. J Org Chem 33:1367–1371; (b) Trifunovic S, Dimitrijevic D, Vasic G, Vukicevic RD, Radulovic N, Vukicevic M, Heinemann FW (2010) New simple synthesis of N-substituted 1,3-oxazinan-2-ones. Synthesis 6:943–946; (c) Shibata I, Nakamura K, Baba A, Matsuda H (1989) Formation of N-Tributylstannyl heterocycle from bis(tributyltin) oxide and ω-haloalkyl isocyanate. One-pot convenient synthesis of 2-oxazolidinones and tetrahydro-2H-1,3-oxazin-2-one. Bull Chem Soc Jpn 62:853–859; (d) Mangelinckx S, Nural Y, Dondas HA, Denolf B, Sillanpaa R, De Kimpe N (2010) Diastereoselective synthesis of 6-functionalized 4-aryl-1,3-oxazinan-2-ones and their application in the synthesis of 3-aryl-1,3-aminoalcohols and 6-arylpiperidine-2,4-diones. Tetrahedron 66:4115–4124