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Streets, Jessica, Proust, Nicolas, Parmar, Dixit, Walker, Gary, Licence, Peter 
ORCID: https://orcid.org/0000-0003-2992-0153 and Woodward, Simon
(2022)
Rate of Formation of Industrial Lubricant Additive Precursors from Maleic Anhydride and Polyisobutylene.
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 26 (9).
pp. 2749-2755.
ISSN 1083-6160
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Abstract
The Alder-ene reaction of neat polyisobutylene (PIB) and maleic anhydride (MAA) to produce the industrially important lubricant additive precursor polyisobutylene succinic anhydride (PIBSA) is studied at 150-180 °C. Under anaerobic conditions with [PIB] ∼1.24 M (550 g mol-1 grade, >80% exo alkene) and [MAA] ∼1.75 M, conversion of exo-PIB and MAA follows second-order near-equal rate laws with kobs up to 5 × 10-5 M-1 s-1 for both components. The exo-alkene-derived primary product PIBSA-I is formed at an equivalent rate. The less reactive olefinic protons of exo-PIB also react with MAA to form isomeric PIBSA-II (kobs up to 6 × 10-5 M-1 s-1). Some exo-PIB is converted to endo-PIB (containing trisubstituted alkene) in a first-order process (kobs ∼1 × 10-5 s-1), while PIBSA-I is difunctionalized by MAA to bis-PIBSAs very slowly. The MAA- and PIB-derived activation parameter ΔG‡(150 °C) 34.3 ± 0.3 kcal mol-1 supports a concerted process, with that of PIBSA-I suggesting a late (product-like) transition state.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | kinetics,ene reaction,thermal,mechanism,energetics,lubricant |
| Faculty \ School: | Faculty of Science > School of Chemistry, Pharmacy and Pharmacology |
| Related URLs: | |
| Depositing User: | LivePure Connector |
| Date Deposited: | 28 Oct 2026 15:16 |
| Last Modified: | 28 Oct 2026 15:16 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/104900 |
| DOI: | 10.1021/acs.oprd.2c00207 |
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