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5 protocols using pentaethylenehexamine

1

Crude Oil Demulsification Protocol

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Pentaethylene hexamine,
tetraethylene pentamine, triethylene tetramene, and GNPE were purchased
from Aldrich company and used without further purification. Xylene
(99.5%) was purchased from Sinpharm Chemical Reagent Corporation.
ARBREAK 8846 is a commercial demulsifier produced by Baker Petrolite
Corporation. Chemically, ARBREAK 8846 is mainly based on a high-molecular
weight oxyalkylated alkylphenolic resin. Riyadh refinery unit; Aramco
Co. was the supplier for Arabian heavy crude oil with specifications
listed in Table 5.
The heavy crude oil and sea water, gathered from Arabian Gulf at Dammam
coast, were utilized to prepare synthetic emulsions with the ratios
of (90/10, 70/30, and 50/50 vol %) heavy crude oil/water.
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2

Synthesis of Hexapropyl-pentaamine Derivative

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Reagents of trifluoroacetic acid, Zn(OAc)2·2H2O, iodomethane (CH3I), m-chloroperoxybenzoic acid (MCPBA), sodium borohydride, pentaethylene hexamine, n-propionaldehyde, and potassium carbonate were purchased from Aldrich Chemicals and used without further purification. Chlorella powder was purchased from Cellusyn Labs, LLC. Vancomycin hydrochloride was purchased from Gold Biotechnology. Solvents were routinely distilled prior to the use. The reagent N,N′,N,N,N,N-hexapropyl-penta(aminoethyl)amine was prepared by a routine protection-deprotection reaction 39 (link) of one primary amine group of pentaethylene hexamine. It was followed by the conversion of 1° or 2° alkylamines to tertiary amines using n-propionaldehyde, as the capping agent, and sodium borohydride as the reducing agent.40
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3

Bioinspired Silica Synthesis at Scale

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Bioinspired silica was synthesised at 150 mL scale by mixing solutions of sodium silicate pentahydrate (Fisher scientific, technical grade) and pentaethylenehexamine (Sigma–Aldrich, technical grade) in deionised water so that the final concentrations were 30 mm for both Si and N. The mixture was subsequently neutralised using 1 m HCl and allowed to react at pH 7.0±0.05 for 5 min. Particles were isolated by centrifugation for 15 min at 4500 g and washing with deionised water, repeated three times, before being dried in an oven at 85 °C overnight. When performing the reaction on a large scale, a 1 or 5 L Reactor‐ReadyTM system was used either in batch or continuous mode. The reactor stirrer was set to 500 rpm, and other parameters and procedures were as described above. Alternative additives used were diethylenetriamine (Sigma–Aldrich, 99 %) at an N concentration of 30 mm, and poly(ethyleneimine) and permethylated poly(etheleneimine) (Polysciences) at a concentration of 1 mg mL−1.
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4

Functionalization of Desiccated Coconut Waste

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Desiccated coconut waste (DCW) was obtained from the local seller in Perlis. Analytical grade of amines; ethylenediamine (EDA), diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentaamine (TEPA), pentaethylenehexamine (PEHA), ethanol, and toluene were purchased from Sigma-Aldrich (Missouri Mo, USA). CO 2 (99.9% purity) was supplied by Air Product Malaysia. These chemicals were used directly without any further purification. Table S1 shows the structure of the series of amines used for the functionalization procedure.
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5

Characterization of Polyisobutylene Succinic Anhydride

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Chemicals. Acetone (HPLC grade, Caledon), hexane (HPLC grade, Caledon), xylene (reagent grade, 98.5%, EMD), deuterated chloroform (CDCl3, 99.8%, Cambridge Isotope Laboratories, Inc.), tetrahydrofuran (THF, HPLC grade, Caledon), dodecane (anhydrous, 99%, Sigma-Aldrich), ethyl ether (anhydrous, 99% Sigma-Aldrich), ethyl acetate (HPLC, 99.7% Sigma-Aldrich), and 2-dodecanone (GC grade, 97%, Sigma-Aldrich) were used as received. The chemicals hexamethylenediamine (HMDA, 98%), diethylenetriamine (DETA, 99%), triethylenetetramine (TETA, 97%), tetraethylenepentamine (TEPA, technical grade), pentaethylenehexamine (PEHA, technical grade), dibutylamine (DBA, 99.5%), octylamine (99%), N-methylsuccinimide (N-MSI, 99%), butylamine (BUA, 99%), diethylamine (DEA, 99.5%), triethylamine (TEA, 99.5%), ethylene carbonate (EC, 98%), magnesium sulfate anhydrous (97%), and activated charcoal (100 mesh) were purchased from Sigma-Aldrich and were employed without further purification. Polyisobutylene succinic anhydride (PIBSA) was supplied by Imperial Oil. The chemical composition of this sample was characterized by NMR, GPC, and FTIR analysis and found to contain on average one SA unit per 52 ± 2 isobutylene monomers. Assuming one SA moiety per chain, this PIBSA sample would have an Mn of 3,012 g.mol  equivalent to a total acid number (TAN) of 37.2 mg of KOH per gram of PIBSA.
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