Preparation of Macrocyclic Lactones by Depolymerization 1
Abstract
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPreparation of Macrocyclic Lactones by Depolymerization1E. W. Spanagel and W. H. CarothersCite this: J. Am. Chem. Soc. 1936, 58, 4, 654–656Publication Date (Print):April 1, 1936Publication History Published online1 May 2002Published inissue 1 April 1936https://doi.org/10.1021/ja01295a038RIGHTS & PERMISSIONSArticle Views309Altmetric-Citations43LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (275 KB) Get e-Alerts Get e-Alerts
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Depending on the starting polyesters, either cyclic monomer or dimer were obtained in moderate yield (50-70%) and selectivity (50~90%).
“Depending on the starting polyesters, either cyclic monomer or dimer were obtained in moderate yield (50-70%) and selectivity (50 ~ 90%).”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [456]
Back in 1939, Carothers described the selective depolymerization of polydecanoate, polytridecanoate and polytetradecanoate at 270 °C and 1 mm Hg pressure using MgCl2 or SnCl2 as the catalyst.
“Back in 1939, Carothers has described the selective depolymerization of polydecanoate, polytridecanoate and polytetradecanoate at 270 °C and 1 mm Hg pressure using MgCl2 or SnCl2 as the catalyst.456,457”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [456]
Cited by
Sorted by citations
Catalysis as an Enabling Science for Sustainable Polymers
Zhang, X., Fevre, M., Jones, G. O., & Waymouth, R. M. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00329 · Cited by 936 · see citing works
Fráter, G., Bajgrowicz, J. A., & Kraft, P. (1998) · Tetrahedron · doi:10.1016/s0040-4020(98)00199-9 · Cited by 310 · see citing works
Nicolaou, K. C. (1977) · Tetrahedron · doi:10.1016/0040-4020(77)80180-4 · Cited by 295 · see citing works
Rousseau, G. (1995) · Tetrahedron · doi:10.1016/0040-4020(94)01064-7 · Cited by 192 · see citing works
The synthesis of macrocyclic lactones
Back, T. G. (1977) · Tetrahedron · doi:10.1016/0040-4020(77)80449-3 · Cited by 184 · see citing works
Entropically Driven Ring-Opening Polymerization of Strainless Organic Macrocycles
Hodge, P. (2014) · Chemical Reviews · doi:10.1021/cr400222p · Cited by 176 · see citing works
Die konfiguration der carbonestergruppe und die sondereigenschaften der lactone
Huisgen, R., & Ott, H. (1959) · Tetrahedron · doi:10.1016/0040-4020(59)80006-5 · Cited by 174 · see citing works
Cooper, D. R., & Semlyen, J. A. (1973) · Polymer · doi:10.1016/0032-3861(73)90045-1 · Cited by 84 · see citing works
Natural Polyesters: Dufour's Gland Macrocyclic Lactones Form Brood Cell Laminesters in Colletes Bees
Hefetz, A., Fales, H. M., & Batra, S. W. T. (1979) · Science · doi:10.1126/science.204.4391.415 · Cited by 83 · see citing works
Ynamide-Mediated Macrolactonization
Yang, M., Wang, X., & Zhao, J. (2020) · ACS Catalysis · doi:10.1021/acscatal.0c00523 · Cited by 80 · see citing works
Polymerhomologe ringamide in polycaprolactam
Rothe, M. (1958) · Journal of Polymer Science · doi:10.1002/pol.1958.1203012118 · Cited by 69 · see citing works
Direct Macrolactonization of Seco Acids via Hafnium(IV) Catalysis
de Léséleuc, M., & Collins, S. K. (2015) · ACS Catalysis · doi:10.1021/acscatal.5b00082 · Cited by 41 · see citing works
Hodge, P., Yang, Z. L., Ben-Haida, A., & McGrail, C. S. (2000) · Journal of Materials Chemistry · doi:10.1039/b002786n · Cited by 41 · see citing works
Chemie der Geruchs- und Geschmacksstoffe
Ohloff, G. (2006) · Springer eBooks · doi:10.1007/bfb0050693 · Cited by 36 · see citing works
LEDERER, P. E. (1950) · Springer eBooks · doi:10.1007/978-3-7091-7175-2_2 · Cited by 34 · see citing works
Ruddick, C. L., Hodge, P., Zhuo, Y., Beddoes, R. L., & Helliwell, M. (1999) · Journal of Materials Chemistry · doi:10.1039/a903767e · Cited by 34 · see citing works
Die konfiguration der carbonestergruppe und die sondereigenschaften der lactone
Huisgen, R., & Ott, H. (1959) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)70305-4 · Cited by 31 · see citing works
Seebàch, D., Herrmann, G. F., Lengweiler, U. D., et al. (1997) · Helvetica Chimica Acta · doi:10.1002/hlca.19970800402 · Cited by 30 · see citing works
Salomon, G. (1936) · Helvetica Chimica Acta · doi:10.1002/hlca.193601901106 · Cited by 30 · see citing works
Staudinger, H., & Nuss, O. (1941) · Journal für praktische Chemie · doi:10.1002/prac.19411570803 · Cited by 26 · see citing works
Recycling of condensation polymers via ring–chain equilibria
Hodge, P. (2015) · Polymers for Advanced Technologies · doi:10.1002/pat.3469 · Cited by 25 · see citing works
Kraft, P. (2004) · doi:10.1002/9781444305517.ch7 · Cited by 19 · see citing works
From Polymers to Rings and Back Again: Chemical Recycling of Polyesters to Macrolactones
Smith, M. L., McGuire, T. M., Kerr, R. W. F., & Williams, C. K. (2025) · Angewandte Chemie International Edition · doi:10.1002/anie.202423478 · Cited by 19 · see citing works
Über die Dehydratisierung von Thioglykolsäure, deren Kondensationspolymere und über Dithioglykolid
Schöberl, A., & Wiehler, G. (1955) · Justus Liebig s Annalen der Chemie · doi:10.1002/jlac.19555950203 · Cited by 18 · see citing works
Collaud, C. (1942) · Helvetica Chimica Acta · doi:10.1002/hlca.19420250518 · Cited by 17 · see citing works
Mass Spectral Characteristics of Pivalolactone and Polypivalolactone
Wiley, R. H. (1970) · Journal of Macromolecular Science Part A - Chemistry · doi:10.1080/00222337008059522 · Cited by 16 · see citing works
Aliphatic Polyester Formation, Mechanisms of
Duda, A., & Penczek, S. (2002) · Wiley eBooks · doi:10.1002/3527600035.bpol3b12 · Cited by 14 · see citing works
Transannular reaction between ester and amide groups. Formation of a cyclol peptide derivative
Sheppard, R. C. (1963) · Cellular and Molecular Life Sciences · doi:10.1007/bf02171584 · Cited by 14 · see citing works
Chapuis, C., Robvieux, F., Cantatore, C., et al. (2012) · Helvetica Chimica Acta · doi:10.1002/hlca.201100398 · Cited by 12 · see citing works
Darstellung und Konfiguration von Heptanolid und Octanolid
Huisgen, R., & Ott, H. (1958) · Angewandte Chemie · doi:10.1002/ange.19580701009 · Cited by 12 · see citing works
Synthesis of Macrocyclic Oxalactone by Photocyclization.
Kurata, T., & KINOSHITA, R. (2001) · Journal of Oleo Science · doi:10.5650/jos.50.759 · Cited by 9 · see citing works
Stoll, M., & Rouvé, A. (1944) · Helvetica Chimica Acta · doi:10.1002/hlca.194402701199 · Cited by 9 · see citing works
Mass spectral characteristics of poly(2,6‐dimethyl‐1,4‐phenylene ether)
Wiley, R. H. (1971) · Journal of Polymer Science Part A-1 Polymer Chemistry · doi:10.1002/pol.1971.150090111 · Cited by 9 · see citing works
Stoll, M., & Bolle, P. (1948) · Helvetica Chimica Acta · doi:10.1002/hlca.19480310120 · Cited by 8 · see citing works
Preparation of ω‐hydroxynonanoic acid and its ester derivatives
Kula, J., Smigielski, K. B., Quang, T. B., et al. (1999) · Journal of the American Oil Chemists Society · doi:10.1007/s11746-999-0070-y · Cited by 7 · see citing works
Chemistry of Synthetic Musks I. Nonbenzenoid Musks
Wood, T. F. (1982) · Elsevier eBooks · doi:10.1016/b978-0-12-685850-1.50018-8 · Cited by 7 · see citing works
Animalic Compounds as Odorants
Ohloff, G. (1994) · Springer eBooks · doi:10.1007/978-3-642-78418-7_9 · Cited by 5 · see citing works
Rothe, M. (1999) · doi:10.1002/0471532053.bra022 · Cited by 5 · see citing works
New method for the synthesis of macrocyclic compounds
Gol'dfarb, Y. L., Taits, S. Z., Chirkova, T. S., et al. (1964) · Russian Chemical Bulletin · doi:10.1007/bf00844493 · Cited by 4 · see citing works
Beets, M. G. J., & Meerburg, W. (1953) · Recueil des Travaux Chimiques des Pays-Bas · doi:10.1002/recl.19530720506 · Cited by 4 · see citing works
Thermal degradation and cyclodepolymerization of poly(ethylene terephthalate-co-isophthalate)s
Yoo, D. I., Shin, Y., & Youk, J. H. (2001) · Fibers and Polymers · doi:10.1007/bf02875262 · Cited by 3 · see citing works
Animalische Drogen Als Riechstoffe
Ohloff, G. (1990) · Springer eBooks · doi:10.1007/978-3-662-09768-7_9 · Cited by 3 · see citing works
From Polymers to Rings and Back Again: Chemical Recycling of Polyesters to Macrolactones
Smith, M. L., McGuire, T. M., Kerr, R. W. F., & Williams, C. K. (2025) · Angewandte Chemie · doi:10.1002/ange.202423478 · Cited by 2 · see citing works
Macrocyclic musks: Trends in development and synthetic strategies
Gadgil, V. R., Chopada, A., Chavarkar, G. R., et al. (2025) · Tetrahedron · doi:10.1016/j.tet.2025.134767 · Cited by 2 · see citing works
ED-ROP of macrocyclic oligomers: A synthetic tool for multicomponent polymer materials
Stagnaro, P., Brunengo, E., & Conzatti, L. (2021) · ARKIVOC · doi:10.24820/ark.5550190.p011.600 · Cited by 2 · see citing works
“10,11 Aside from the pioneering works of Carothers and collaborators, 12,13 who synthesized aliphatic cyclic oligomeric esters and carbonates by distillative depolymerization of the linear parent polymers, most of the subsequent studies on MCOs up to the 1990s were of academic interest.”
BackgroundMacrocyclic lactones as a source for radiohalogenated fatty acid analogs and their precursors
Dougan, H., Lyster, D. M., & Vincent, J. S. (1985) · Journal of Radioanalytical and Nuclear Chemistry · doi:10.1007/bf02070205 · Cited by 2 · see citing works
Macrocyclic Dilactone. I. The Synthesis of 7-Hydroxyoctanoic Acid Dilactone
Sugiyama, N., Gasha, T., & Kashima, C. (1967) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.40.2713 · Cited by 2 · see citing works
Wallace H. Carothers: Life and Work
Kricheldorf, H. R. (2013) · Springer eBooks · doi:10.1007/978-3-642-39429-4_3 · Cited by 1 · see citing works
Bildung und Spaltung von Organo-oxyden
Klages, F. (1943) · Springer eBooks · doi:10.1007/978-3-7091-5938-5_4 · Cited by 1 · see citing works
Synthesis of 18‐octadecanolide, a major constituent of dufour's gland secretion ofColletes bees
Gangadhar, A., Subbarao, R., & Lakshminarayana, G. (1987) · Journal of the American Oil Chemists Society · doi:10.1007/bf02612989 · Cited by 1 · see citing works
A new method for the synthesis of macrocyclic compounds
Taits, S. Z., Alashev, F. D., & Gol'dfarb, Y. L. (1968) · Russian Chemical Bulletin · doi:10.1007/bf00911609 · Cited by 1 · see citing works
Bildung und Spaltung von Organo-oxyden
Klages, F. (1943) · Springer eBooks · doi:10.1007/978-3-7091-4741-2_4 · Cited by 1 · see citing works
Macrolides from Cyclization of ω‐Bromocarboxylic Acids: 11‐Hydroxyundecanoic Lactone
Galli, C. L., & Mandolini, L. (2003) · Organic Syntheses · doi:10.1002/0471264180.os058.17
A Green Method for Potentially Recycling Condensation Polymers: Ring-Chain Recycling
Hodge, P. (2016) · Springer eBooks · doi:10.1007/978-3-319-30073-3_10
Schäfer, B. (2006) · Springer eBooks · doi:10.1007/978-3-662-61017-6_3
Küchler, L. (1951) · Springer eBooks · doi:10.1007/978-3-662-12725-4_3
10.1016/b978-0-08-022092-5.50009-8
(2000) · Time to knit · doi:10.1016/b978-0-08-022092-5.50009-8
Xiao, J., Wang, M. Y., Lin, X., Dai, S., Guan, S., Ding, Z., & Wang, B. (2026) · Angewandte Chemie · doi:10.1002/ange.8645967
Xiao, J., Wang, M. Y., Lin, X., Dai, S., Guan, S., Ding, Z., & Wang, B. (2026) · Angewandte Chemie International Edition · doi:10.1002/anie.8645967 · Cited by 1 · see citing works
Wang, X., Liu, Z., Wang, J., et al. (2026) · Angewandte Chemie · doi:10.1002/ange.2327181
Wang, G., Li, X., Zhang, Y.-H., Liu, H.-Y., Liu, Z., Ren, B., Liu, Q., Zhang, Q., & Li, J. (2026) · ACS Macro Letters · doi:10.1021/acsmacrolett.6c00401
- Authors
- Spanagel, E. W., & Carothers, W. H.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1936-04
- Volume
- 58
- Issue
- 4
- Pages
- 654-656
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2312603287
- Cited by
- 59
- References
- 0
- Citations by year
- 2026: 4 · 2025: 3 · 2021: 1 · 2020: 1 · 2017: 1 · 2016: 1 · 2015: 2 · 2014: 1 · 2013: 1 · 2012: 1
- FWCI
- 0.84
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer Synthesis and Characterization
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Keywords
- macrocyclic lactones, depolymerization, polyesters, ring-opening polymerization, lactone synthesis
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review