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5 protocols using 1 nonene

1

Analytical Reagents for Spectroscopy

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Acetonitrile (99.9%), dichloromethane
(99.8%), 1-bromodecane (98%), ethyl acetate (99.5%), 1-methylimidazole
(99%), nonane (99%), 2-hexanone (99%), methyl tiglate (99%), n-hexane (99.7%), 1-hexene (99.8%), cis-1,4-hexadiene (99%), 2.3-dimethyl-1,3-butadiene (98%), 2-hexyne
(99%), benzene (99.8%), toluene (99.5%), o-xylene
(99.8%), m-xylene (99%), p-xylene
(99%), ethylbenzene (99.8%), 1-nonene (96%), and [Ag+][NTf2] (97%) were purchased from Sigma-Aldrich
(St. Louis, MO, USA). Compounds 3-hexyne (99%) and cis-2-hexene (96%) were purchased from Alfa Aesar (Tewksbury, MA, USA).
Lithium bis[(trifluoromethyl)sulfonyl]imide ([Li+][NTf2], 99.5%) salt was purchased from SynQuest
Laboratories (Alachua, FL, USA). Untreated fused silica capillary
tubing (I.D. 250 μm) and naphthalene (98%) were purchased from
Supelco (Bellefonte, PA, USA). Cylinders containing custom gas mixtures
(ultra-high purity, 99.999%) of hydrogen/nitrogen, hydrogen/helium,
and hydrogen/methane/nitrogen were purchased from Airgas, Inc. (Des
Moines, IA, USA). All chemicals were used as received without further
purification.
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2

Procurement of High-Purity Organic Compounds

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Ethyl palmitate (>99.0% purity) was purchased from Dr. Ehrenstorfer GmbH (Augsburg, Germany). Ethyl oleate (>99.0% purity), methyl palmitate (>99.0% purity) and ethyl myristate (>99.0% purity) were purchased from ANPEL (Shanghai, China). 1-nonene (>99.0% purity) was purchased from Sigma-Aldrich (St. Louis, MO, USA). Ethanol (HPLC-grade) and hexane (HPLC-grade) were purchased from Kermel (Tianjin, China).
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3

Biocatalytic Oxidation of Alkene Substrates

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1-Nonene (98%), 1-heptene (97%), styrene (99%), cyclohexene (99%) and 1-methylcyclohexene (97%), cyclohexene oxide (standard), and Chloroform-d were obtained from Sigma-Aldrich, USA. 1-Methylcyclohexene oxide (standard) was bought from Tokyo Chemical Industry, Japan. Chloroform, ethyl acetate, and toluene were purchased from Fisher Scientific, UK. Acetone, H2O2 (30%, w/w), and phenylacetic acid were purchased from Merck, Germany. A commercially known biocatalyst, CALB, immobilised on a macroporous acrylic resin (Novozym 435) was obtained from Novozymes Corporation, Denmark. The standards for 1-Nonene oxide and 1-heptene oxide were prepared and identified as described by Rusch Gen Klaas and Warwel [15 ]. For GC-MS analysis, ethyl acetate and Chloroform HPLC-grade were procured from Fisher Scientific, UK.
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4

Synthesis and Characterization of PHB

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1-Undecene and 1-tridecene were purchased from Alfa Aesar (MA, USA). PHB, benzoic acid, 1-heptene, 1-nonene, benzoic acid and 3-hydroxybutyric acid were purchased from Sigma-Aldrich (MO, USA). Methyl ester of 3-hydroxyoctanoic acid (3-OH C8), 3-hydroxydecanoic acid (3-OH C10), 3-hydroxydodecanoic acid (3-OH C12) and 3-hydoxytetradecanoic acid (3-OH C14) were purchased from Matreya LLC (PA, USA). All solvents and reagents were either of HPLC grade or analytical reagent grade.
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5

Purification of Nonenes and Decaline

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1-Nonene (TCI ≥ 99.5%), cis-4-nonene (TCI ≥ 95%) and decaline (Sigma Aldrich 98%) were distilled from Na, degassed by three consecutive freeze–pump–thaw cycles, filtered through activated alumina, and stored for 4 hours over activated Selexsorb CD® and activated 4 Å molecular sieves.
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