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Lewis acids as co-catalysts in Pd-based catalyzed systems of the octene-1 hydroethoxycarbonylation reaction

  • Kairzhan Shalmagambetov , Andrea Vavasori , Gulbanu Zhaksylykova , Fatima Kanapiyeva , Meruyert Zykay and Nurbolat Kudaibergenov EMAIL logo
Published/Copyright: November 16, 2023
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Open Chemistry
From the journal Open Chemistry Volume 21 Issue 1

Abstract

In this work, in order to develop new, efficient, and environmentally friendly methods for the preparation of practically valuable esters of carboxylic acids, the hydroalkoxycarbonylation reaction of octene-1 with various alcohols in the presence of metal–complex catalysts based on palladium phosphine complexes has been studied. Three-component systems based on PdCl2(PPh3)2 containing different ligands as stabilizers and Lewis acids as promoters were studied as catalysts. It is shown that the three-component system PdCl2(PPh3)2–PPh3–AlCl3 has the highest catalytic activity in the reactions studied. It was found that the reaction of hydroalkoxycarbonylation of octene-1 proceeds with the formation of a mixture of linear (ethyl ester of pelargonic acid) and branched (ethyl ester of 2-methylcaprylic acid) products. The influence of the ratio of initial reagents (different olefins and alcohols) and components of catalytic systems (different Pd complexes, ligands, and promoters) on the course of the process has been investigated, in which the conversion of octene-1 reached 88.5%. The optimal parameters of the reactions studied were determined.

Keywords: carbonylation; Reppe synthesis; octene-1; Lewis acids; Pd-complex catalysts

1 Introduction

Currently, the progress in catalytic synthesis indicates that the direction of industrial organic synthesis in the future will greatly depend on the effective advancement of homogeneous catalysis. More specifically, it will rely on the innovation of novel homogeneous metal–complex catalysts, which hold significant promise for addressing critical challenges related to conserving raw materials and reducing energy expenses in large-scale organic synthesis processes [1,2,3,4,5]. The advantage of homogeneous metal–complex catalysts over heterogeneous ones is their high regio-, enantio-, and diastereoselectivity, while they operate under mild conditions, i.e., at low temperatures and pressures with high yields of target products [6,7,8,9,10,11].

The hydroalkoxycarbonylation process presents an appealing and practical approach to the functionalization of olefins. It offers advantages such as cost-effectiveness, resource efficiency, and the ready availability of starting materials (refer to Scheme 1) [12,13,14]. This method is already employed in industrial settings to manufacture methyl propionate by the process known as the alpha process. In the hydroalkoxycarbonylation of olefins, which involves carbon monoxide (CO) and different alcohols (ROH), the effectiveness and specificity of homogeneous metal–complex catalysts can be enhanced by adjusting various factors. These factors include altering the ligands, introducing promoters, adjusting the ratios of components within catalytic systems and starting materials, as well as controlling the reaction pressure, temperature, and reaction duration [15,16,17,18]. The resulting products, particularly esters, have wide-ranging industrial applications and serve as valuable reagents. They have practical applications in manufacturing solvents, scents, aromas, cleaning agents, and surface-active agents [19,20].

Scheme 1 General scheme of the hydroalkoxycarbonylation of terminal olefins.
Scheme 1

General scheme of the hydroalkoxycarbonylation of terminal olefins.

Catalysts derived from transition metal complexes within the VIII group of the periodic table exhibit the highest level of catalytic effectiveness in the hydroalkoxycarbonylation reaction of olefins. The selectivity, endurance, and catalytic activity of these metal-based catalysts within this group depend on several factors. These variables depend on the particular chelating agent used, the makeup of the coordination sphere, process operational parameters, and the incorporation of external stabilizers and promoters. At present, among the most encouraging catalysts are those composed of palladium phosphine complexes, as they exhibit a favorable blend of donor and acceptor characteristics in both zero- and divalent states [15,16]. Within catalytic systems relying on Pd-based phosphine complexes, triphenylphosphine serves as a stabilizing agent. Its ability to provide stability is linked to its role in preserving the integrity of the core complex, thereby preventing the possible deactivation of active complexes during the catalytic reaction cycle caused by ligand exchange reactions. Additionally, different Bronsted acids are frequently used as external enhancers. These promoters assist in promoting the formation of intermediate palladium hydride complexes, which have a central role in the catalytic cycle of the process [21,22,23].

Recently, there has been an increasing focus on investigating Lewis acids in addition to Bronsted acids as catalyst promoters [24,25,26,27,28,29]. Huang and colleagues, for instance, employed cost-effective trivalent iron salts such as Lewis acids in the carbonylation reaction of various aromatic and aliphatic olefins. This approach resulted in the production of carboxylic acids with exceptional regioselectivity and impressive product yields of up to 96% [25]. In a different research investigation, Amezquita-Valencia highlighted the importance of employing a Lewis acid, such as SnCl2 or Ti(OiPr)4, along with a monodentate ligand like CYTOP 292 or P(p-anisyl)3 to improve regioselectivity. This approach led to regioselectivity levels between 70 and 96% for linear isomers [26]. Furthermore, Ferreira and colleagues described the use of borosalicylic acid as an appealing acidic promoter catalyzed with palladium on the ethylene ethoxycarbonylation reaction, employing triphenylphosphine as a ligand [27]. Yang and Yuan also demonstrated that incorporating a Lewis acid with acidity levels similar to p-TsOH significantly enhanced both the rate and yield of the styrene hydroesterification reaction. This approach also led to a substantial reduction in the consumption of phosphine ligands within the catalytic system [28].

In this study, the hydroalkoxycarbonylation reaction of octene-1 was investigated using three-component Pd-catalyzed systems. These systems featured Pd complexes with different ligands for stabilization and Lewis acids as promoters.

2 Materials and methods

2.1 Initial materials and research methods

As initial reagents in the work, (dichlorbis(triphenylphosphine) palladium, dichlorbis(triorthotolyl-phosphine) palladium, dichlorbis(trimetatolylphosphine) palladium, dichlorbis-(triparatolylphosphine) palladium, dichlorbis(triorthomethoxyphenylphosphine) palladium, dichlorbis(tricyclohexylphosphine) palladium, dixlorbis-(triparafluorophenylphosphine) palladium, dibrombis(triphenylphosphine) palladium, diiodbis(triphenylphosphine) palladium, Pd/Amberlyst IRC50, Pd/C 5%, triphenylphosphine, triorthotolylphosphine, trimetatolylphosphine, tripartolylphosphine, triorthomethoxyphenylphosphine, tricyclohexylphosphine, triparfluorophenylphosphine, hexene-1, octene-1, decene-1, cyclohexene, aluminum trichloride, tin dichloride, iron trichloride, indium trichloride, ytterbium triphthalate, lanthanum trichloride heptahydrate, praseodymium trichloride hexahydrate, ytterbium trichloride hexahydrate, samarium trichloride hexahydrate), absolute alcohols (methanol, ethanol, n-propanol, n-butanol), and CO were used without special purification (SIGMA-ALDRISH company).

The experiment procedures were conducted in a stainless steel laboratory apparatus of autoclave type, and no solvents were employed during the process. The olefin conversion and the ratio of isomeric ester products (linear and branched) were carried out by chromatography with an Agilent 7890A/5975C (USA) gas chromatography-mass spectrometer system. The chromatographic conditions were as follows: a gas chromatograph 7890A equipped with a mass-selective detector 5975C from Agilent; the carrier gas used was helium; the evaporator temperature was set at 300°C, with a flow split ratio of 1,000:1; the initial column thermostat temperature was 40°C for 1 min, followed by a temperature ramp of 50°C per min until reaching 250°C, held for 1 min, resulting in a total analysis time of 44 min; and the mass detector was operated in the electron impact ionization mode. A capillary chromatographic column, HP-FFAP, was used with a length of 30 m and an inner diameter of 0.25 mm; the stationary phase consisted of nitroterephthalic acid modified with polyethylene glycol.

The substances generated were subjected to analysis by both infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy methods. For IR spectra, a Nicolet 5700 single-beam infrared spectrometer manufactured by Thermo Electron Corporation (USA) was employed, covering the range from 400 to 4,000 cm−1. For 1H NMR spectra, a Bruker DPX 400 instrument operating at 300 MHz was utilized.

2.2 Carbonylation experiments

Hydroethoxycarbonylation of octene-1. A 100 mL steel autoclave (Figure 1), equipped with a stirrer and CO injection apparatus, was loaded with the following components: 1 mL (0.715 g, 6.37 mmol) of octene-1, 9 mL (7.1 g, 154.4 mmol) of ethanol, 0.008 g (0.0114 mmol) of PdCl2(PPh3)2, 0.036 g (0.1367 mmol) of PPh3, and 0.152 g (1.14 mmol) of AlCl3. The autoclave was sealed and was subjected to three cycles of CO purging to eliminate any air. It was subsequently pressurized with CO to reach a pressure of 3.5 MPa, after which stirring and heating were initiated. The temperature was then gradually increased to 120°C for 1 h. The pressure was adjusted to 5.0 MPa, and under these temperature and pressure conditions, the reaction mixture was stirred for 5 h. Subsequently, stirring and heating were stopped, and the autoclave was allowed to cool to room temperature. Finally, the reaction mixture was analyzed using a gas chromatograph with a mass-selective detector. The conversion of octene-1 was 88.5%, and the ratio of branched/linear products was 1:2.35. The conversion was expressed as [(initial moles of octene-1 − final moles of octene-1)/initial moles of octene-1] × 100. The resulting reaction products (linear (ethyl ester of pelargonic acid) and branched (ethyl ester of 2-methylcaprylic acid)) were separated by fractional vacuum distillation, and experimental data of the boiling point of the products in a vacuum of 10 mmHg are 110–115°C, and literature data at a vacuum of 760 mmHg are 227–228°C.

Figure 1 Schematic diagram of a laboratory autoclave unit for the olefin hydroesterification reaction. 1 – gas cylinder with CO; 2 – autoclave; 3 – electric heater; 4, 6 – microvalves for gas inlet and outlet; 5 – manometer; 7 – magnetic stirrer; 8 – gas and temperature regulator; 9 – reducer.
Figure 1

Schematic diagram of a laboratory autoclave unit for the olefin hydroesterification reaction. 1 – gas cylinder with CO; 2 – autoclave; 3 – electric heater; 4, 6 – microvalves for gas inlet and outlet; 5 – manometer; 7 – magnetic stirrer; 8 – gas and temperature regulator; 9 – reducer.

3 Results and discussion

Our experimental data for the hydroalkoxycarbonylation reaction of octene-1 were divided into the following five sections.

The effects of the molar ratio of AlCl3 on the hydroalkoxycarbonylation reaction of olefins, the nature of precursors, ligands, and promoters of various alcohols, and olefins are summarized in Tables 1–5. The catalytic system composed of PdCl2(PPh3)2–PPh3–AlCl3, with AlCl3 serving as a promoter, was observed to demonstrate remarkable catalytic efficiency. The optimal process conditions and selectivity of conversion of olefins and target products were determined.

Table 1

Effect of the concentration of AlCl3 on the hydroethoxycarbonylation of octene-1

Entry Catalytic system ratio [PdCl2(PPh3)2]/[PPh3]/[AlCl3] (in mmol) Conversion of olefin (%) Selectivity iso:n
1 1:12:8 46.6 1:2.5
2 1:12:16 60.5 1:2.8
3 1:12:32 70.1 1:2.7
4 1:12:100 88.5 1:2.35

Reaction conditions: The reagents [olefin]/[alcohol] and their volume, mL: [octene-1]/ [EtOH] = 1:9. T = 120°C, P CO = 5.0 MPa, and τ = 5 h.

Table 2

Effect of the nature of alcohols on the hydroalkoxycarbonylation of octene-1

Entry Reagents [octene-1]/[alcohol] = 1:9 (in volume, mL) Catalytic system ratio [PdCl2(PPh3)2]/[PPh3]/[promoter] = 1:12:100 (in mmol) Conversion of olefin (%) Selectivity iso:n
1 MeOH AlCl3 45.1 1:1.6
2 EtOH AlCl3 88.5 1:2.35
3 n-PrOH AlCl3 78.6 1.7:1
4 n-BuOH AlCl3 96.2 1:11.15
5 n-BuOH p-PsOH·H2O 84.6 1:9.1

Reaction conditions: T = 120°C, P CO = 5.0 MPa, and τ = 5 h.

Table 3

Hydroethoxycarbonylation of other olefins under the same conditions of octene-1

Entry Reagents [olefin]/[alcohol] (in volume, mL) Conversion of olefin (%) Selectivity iso:n
1 [Hexene-1]/[EtOH] = 0.8:9.2 41.8 1.46:1
2 [Octene-1]/[EtOH] = 1:9 88.5 1:2.35
3 [Decene-1]/[EtOH] = 1.2:8.8 84.4 1:2.48
4 [Cyclohexene]/[EtOH] = 0.65:9.35 21.1 —

Reaction conditions: T = 120°C, P CO = 5.0 MPa, and τ = 5 h. Catalytic system ratio (in mmol): [PdCl2(PPh3)2]/[PPh3]/[AlCl3] = 1:12:100.

Table 4

Effects of different catalyst complexes (C1–C11) and ligands (L1–L8) on the hydroethoxycarbonylation of octene-1

Entry Catalytic system ratio [Pd]/[ligand]/[AlCl3] = 1:12:100 (in mmol) Conversion of olefin (%) Selectivity iso:n
1 [C1]:[L1] 75.5 1.34:1
2 [C2]:[L1] 26.4 3.2:1
3 [C1]:[L2] 66.8 1:1.1
4 [C3]:[L2] 21.5 1.25:1
5 [C1]:[L3] 86.8 1:2.15
6 [C4]:[L3] 70.5 1:2.45
7 [C1]:[L4] 75.0 1.37:1
8 [C5]:[L4] 25.5 1.32:1
9 [C1]:[L5] 82.5 1:1.88
10 [C6]:[L5] 82.8 1:1.56
11 [C1]:[L6] 78.8 1:2.57
12 [C7]:[L6] 77.0 1:2.28
13 [C8]:[L7] 87.1 1:2.4
14 [C9]:[L7] 83.1 1:2.05
15 [C10]:[L7] 53.4 1:2.45
16 [C11]:[L7] 79.8 1:2.37

Reaction conditions: T = 120°C, P CO = 5.0 MPa, and τ = 5 h. Reagent: [octene-1]/[EtOH] = 1:9 (in volume, mL).

Table 5

Effect of various co-catalysts on the hydroethoxycarbonylation of octene-1

Entry Co-catalysts Conversion olefin (%) Selectivity iso:n
1 SnCl2 20.2 1:4.35
2 Yb(OTf3) 22.4 1:5.1
3 FeCl3 73.5 1:2.06
4 InCl3 23.3 1:2.2
5 LaCl3·7H2O 57.8 1:3.1
6 PrCl3·6H2O 76.6 1:2.85
7 YbCl3·6H2O 61.3 1:3.01
8 SmCl3·6H2O 73.4 1:2.74

Reaction conditions: T = 120°C, P CO = 5.0 MPa, and τ = 5 h. Reagent: [octene-1]/[EtOH] = 1:9 (in volume, mL). Catalytic system ratio: [PdCl2(PPh3)2]/[PPh3]/[promoter] = 1:12:100 (in mmol).

In the IR spectrum of the resulting compounds, several notable features were observed, including a prominent absorption peak at 1,737 cm−1 (indicating the presence of a carbonyl (C═O) group in the ester), distinct absorption bands in the 1,033–1,300 cm−1 range (referred to as the “ether band”), and absorption bands corresponding to CH, CH2, and CH3 groups at approximately 729, 1,300–1,462, and 2,800–3,000 cm−1, respectively. The 1H NMR data, recorded in deuterochloroform with tetramethylsilane as the reference, revealed that the products obtained from the hydroethoxycarbonylation of octene-1 consisted of both the primary linear product and a mixture with a branched product. The NMR spectra provided specific information about proton shifts and coupling constants (J values). The methylene group protons of the ethyl radical within the alcohol component appeared at a chemical shift of 4.12 ppm as a quartet (J = 7.3 Hz). Protons from the adjacent methyl group resonated at around 1.25 ppm as a triplet with a J value of 7.3 Hz. Methyl group protons within the acid part of the molecule, with a chemical shift of 0.88 ppm, displayed a triplet with a J value of 5.3 Hz, located in the strongest field of the spectrum. Methylene group protons neighboring the carbonyl group (–CH2–C(O)–O–) were observed as a triplet at 2.28 ppm (J = 7.3 Hz). A multiplet peak at 1.62 ppm was attributed to methylene protons of the carbon atom C5. The remaining methylene protons of carbon atoms C2, C3, and C4 were detected as a multiplet centered at 1.29 ppm. Additionally, the presence of an impurity, specifically the isomeric branched product (ethyl ester of 2-methylcaprylic acid), was identified by distinctive NMR signals, including a doublet signal for methylene protons of carbon atom C5 at 1.13 ppm (J = 6.8 Hz) and a multiplet signal for the methyl proton of the C5 carbon atom at 2.4 ppm (J = 8 Hz). The signals corresponding to other protons of the ethyl ester of 2-methylcaprylic acid were observed along with signals from the corresponding protons of the primary linear product (ethyl ester of pelargonic acid).

3.1 Effect of the [Pd]/[AlCl3] concentration ratio on the hydroethoxycarbonylation of octene-1

The influence of the molar ratio of the promoter (AlCl3) in the component of the catalytic system in the octene-1 hydroethoxycarbonylation reaction at low pressure of CO on the conversion of the initial octene-1 was investigated (Table 1). The ratio [PdCl2(PPh3)2]/[PPh3]/[AlCl3] = 1:12:100 was proved to be the most optimal. Accordingly, the conversion of octene-1 was 88.5%. The ratio of branched/linear products was 1:2.35.

3.2 Influence of the nature of different alcohols on the hydroalkoxycarbonylation reaction of octene-1

In the reaction of hydroalkoxycarbonylation of olefins, we studied how the nature of different aliphatic alcohols affects the conversion of olefins (Table 2). The reaction with methyl alcohol proceeded very intensively. Palladium niello was observed in the reaction product, indicating the possibility of deactivation of the catalytic system. Accordingly, the conversion of octene-1 was low at 45.1%. The ratio of branched/linear products is 1:1.6 (Table 2, e1). Thus, it is established that the reaction of hydroalkoxycarbonylation of octene-1 with n-propanol in the presence of PdCl2(PPh3)2–PPh3–AlCl3 system yields a mixture of products (linear and branched), with the selectivity of the branched product prevailing (Table 2, e3). The hydroalkoxycarbonylation of octene-1 with n-butanol in the presence of PdCl2(PPh3)2–PPh3–AlCl3 also proceeds with the formation of a mixture of linear and branched products, with the selectivity of the linear product predominating (Table 2, e4), and in the case of using p-PsOH·H2O as a promoter, a decrease in the yield of the branched product is observed (Table 2, e5).

3.3 Hydroethoxycarbonylation of hexene-1, decene-1, and cyclohexene similar to the reaction conditions using octene-1

The hydroethoxycarbonylation of hexene-1, decene-1, and cyclohexene with the PdCl2(PPh3)2–PPh3–AlCl3 system was studied in order to determine the influence of the radical size of α-olefins on the conversion of the initial olefins and regioselectivity: [PdCl2(PPh3)2]/[PPh3]/[AlCl3] = 1:12:100, CO pressure 5.0 MPa, temperature 120°C, and duration 5 h. The experimental results obtained are summarized in Table 3. The reaction process also results in the creation of both linear and branched products.

As indicated by the information presented in Table 3, with an increase in the value of the radical of the initial olefin, an increase in the conversion is observed (from 41.8% for hexene-1 to 84.4% for decene-1), and in the case of cyclohexene, an insignificant conversion is observed (21.1%).

3.4 Hydroethoxycarbonylation of octene-1 using various catalytic systems with AlCl3 as a promoter

The optimal properties of palladium in its role as a complex-forming agent are linked to its ability to exhibit a beneficial blend of donor and acceptor characteristics in both its zero-valent and divalent states. Due to this, the palladium center can form relatively stable intermediates with reagents included in its coordination sphere (alkenes, CO), which at the same time have sufficient reactivity for subsequent interactions. Phosphine complexes of palladium (mainly triphenylphosphine complexes of palladium) and systems based on the latter are especially effective as a catalyst for the reaction of hydroalkoxycarbonylation of olefins.

The comparative catalytic activity of a number of phosphine complexes of Pd and free ligands in three-component systems of the reaction of hydroethoxycarbonylation of octene-1 under the optimal conditions (T = 120°C, P CO = 5.0 MPa, τ = 5 h) of the process in the presence of the system PdCl2(PPh3)2–PPh3–AlCl3 was determined. The experimental results obtained are summarized in Table 4. As can be seen from the data in Table 4, the systems PdCl2(PPh3)2–P(m-tolyl)3–AlCl3, PdCl2(PPh3)2–P(p-tolyl)3–AlCl3, and PdCl2(P(p-tolyl)3)2–P(p-tolyl)3–AlCl3 show high catalytic activity, with PdBr2(PPh3)2–PPh3–AlCl3, PdI2(PPh3)2–PPh3–AlCl3 conversion of initial octene-1 exhibiting above 80%, and other catalytic systems showed moderate catalytic activity. At the same time, the catalytic systems are stable and palladium niello release was not observed. The following heterogeneous applied palladium catalysts were used for comparative analysis: Pd/Amberlyst IRC50/5% (C10) and Pd/C 5% (C11) [30].

3.5 Effect of different promoters on the hydroethoxycarbonylation reaction of octene-1

In order to determine the effect of Lewis acids as promoters in the reaction of hydroethoxycarbonylation of octene-1 in the initial catalytic system PdCl2(PPh3)2–PPh3-promoter, the following promoters were used in the initial catalytic system PdCl2(PPh3)2–PPh3-promoter under the optimal conditions: SnCl2, Yb(OTf3), FeCl3, InCl3, LaCl3·7H2O, PrCl3·6H2O, YbCl3·6H2O, and SmCl3·6H2O (Table 5). As can be seen from the data in Table 5, of all the Lewis acids tested, the catalytic systems using FeCl3, PrCl3·6H2O and SmCl3·6H2O as promoters showed the highest catalytic activity. It was found that SnCl2, Yb(OTf3), and InCl3 are less efficient than AlCl3. In particular, 100 mol of AlCl3 is required for the efficient formation of active Pd–H forms. This result is superior to all Lewis acids tested (e.g. FeCl3) in both conversion and regioselectivity. The effect of the critical anion on regioselectivity was elucidated using PdCl2(PPh3)2 as the metal complex. In particular, chloride anions can affect regioselectivity by promoting the formation of iso- and n-isomers, respectively.

In the hydroalkoxycarbonylation reaction of olefins using a palladium-based catalytic system, Lewis acids play a crucial role in promoting the formation of palladium hydride intermediate complexes. This reaction is a fundamental process in organic synthesis for the conversion of olefins into carbonyl compounds (aldehydes or ketones) by incorporating both an alkoxyl and a C═O group into the olefin substrate. Lewis acids, by definition, are electron-pair acceptors, while Brønsted acids are proton (H+) donors. In the hydroalkoxycarbonylation reaction, Lewis acids can coordinate with both the olefin substrate and palladium catalyst, facilitating the necessary interactions for the catalytic cycle. This coordination chemistry allows Lewis acids to activate and stabilize various intermediates and transition states during the reaction. Lewis acids can be more versatile in terms of substrate scope. They can be applied to a wide range of olefins and reaction partners, offering greater flexibility in designing and optimizing catalytic systems for various hydroalkoxycarbonylation reactions.

4 Conclusions

Thus, when using different Lewis acids as promoters in the composition of the catalytic system in the reaction of hydroalkoxycarbonylation of octene-1, the three-component system PdCl2(PPh3)2–PPh3–AlCl3 showed the highest catalytic activity.

Thus, in the context of the hydroalkoxycarbonylation reaction of octene-1, the inclusion of various Lewis acids as promoters within the catalytic system revealed that the three-component system combination of PdCl2(PPh3)2–PPh3–AlCl3 showed the highest catalytic activity. The conversion of octene-1 was 88.5% and the ratio of branched and linear products was 1:2.35. When economical and easily obtainable Lewis acid salts are incorporated into the catalytic system, numerous olefins are transformed into the targeted carboxylic acid esters with substantial conversions and medium to excellent regioselectivity. The influence of the critical anion on the regioselectivity was elucidated using PdCl2(PPh3)2 as a metal complex. In particular, the chloride anions can affect the regioselectivity by promoting the formation of linear and branched isomers, respectively.

For the first time, the comparative catalytic activity of a number of phosphine complexes of Pd and free ligands in three-component systems of the reaction of hydroethoxycarbonylation of octene-1 was carried out under the optimal conditions (T = 120°C, P CO = 5.0 MPa, τ = 5 h) for carrying out the process by using the PdCl2(PPh3)2–PPh3–AlCl3 system.

  1. Funding information: This research was funded by the Science Committee of the Ministry of Education and Science of the Republic of Kazakhstan (Grant No. AP09058656 “Development of scientific foundations for metal complex hydroalkoxycarbonylation of C4–C10 olefins in oil refining”).

  2. Author contributions: K.Sh. and N.K. – conceptualization; K.Sh. and A.V. – methodology; G.Zh. and F.K. – software; M.Z. and F.K. – validation; G.Zh. and N.K. – formal analysis; K.Sh., G.Zh., and N.K. – investigation; N.K. – data curation; K.Sh., A.V., and N.K. – writing – original draft preparation; K.Sh., A.V., and N.K. – writing – review and editing; K.Sh., M.Z., and N.K. – visualization; K.Sh. – supervision; N.Zh. – project administration. All authors have read and agreed to the published version of the manuscript.

  3. Conflict of interest: The authors state no conflict of interest.

  4. Informed consent statement: Not applicable.

  5. Ethical approval: The conducted research is not related to either human or animal use.

  6. Data availability statement: All data generated or analyzed during this study are included in this published article (and its supplementary information files).

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Received: 2023-09-23
Revised: 2023-10-30
Accepted: 2023-10-31
Published Online: 2023-11-16

© 2023 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/chem-2023-0156
Keywords for this article
carbonylation; Reppe synthesis; octene-1; Lewis acids; Pd-complex catalysts
Creative Commons
BY 4.0

Articles in the same Issue

  1. Characteristics, source, and health risk assessment of aerosol polyaromatic hydrocarbons in the rural and urban regions of western Saudi Arabia
  2. Regular Articles
  3. A network-based correlation research between element electronegativity and node importance
  4. Pomegranate attenuates kidney injury in cyclosporine-induced nephrotoxicity in rats by suppressing oxidative stress
  5. Ab initio study of fundamental properties of XInO3 (X = K, Rb, Cs) perovskites
  6. Responses of feldspathic sandstone and sand-reconstituted soil C and N to freeze–thaw cycles
  7. Robust fractional control based on high gain observers design (RNFC) for a Spirulina maxima culture interfaced with an advanced oxidation process
  8. Study on arsenic speciation and redistribution mechanism in Lonicera japonica plants via synchrotron techniques
  9. Optimization of machining Nilo 36 superalloy parameters in turning operation
  10. Vacuum impregnation pre-treatment: A novel method for incorporating mono- and divalent cations into potato strips to reduce the acrylamide formation in French fries
  11. Characterization of effective constituents in Acanthopanax senticosus fruit for blood deficiency syndrome based on the chinmedomics strategy
  12. Comparative analysis of the metabolites in Pinellia ternata from two producing regions using ultra-high-performance liquid chromatography–electrospray ionization–tandem mass spectrometry
  13. The assessment of environmental parameter along the desalination plants in the Kingdom of Saudi Arabia
  14. Effects of harpin and carbendazim on antioxidant accumulation in young jujube leaves
  15. The effects of in ovo injected with sodium borate on hatching performance and small intestine morphology in broiler chicks
  16. Optimization of cutting forces and surface roughness via ANOVA and grey relational analysis in machining of In718
  17. Essential oils of Origanum compactum Benth: Chemical characterization, in vitro, in silico, antioxidant, and antibacterial activities
  18. Translocation of tungsten(vi) oxide/gadolinium(iii) fluoride in tellurite glasses towards improvement of gamma-ray attenuation features in high-density glass shields
  19. Mechanical properties, elastic moduli, and gamma ray attenuation competencies of some TeO2–WO3–GdF3 glasses: Tailoring WO3–GdF3 substitution toward optimum behavioral state range
  20. Comparison between the CIDR or sponge with hormone injection to induce estrus synchronization for twining and sex preselection in Naimi sheep
  21. Exergetic performance analyses of three different cogeneration plants
  22. Psoralea corylifolia (babchi) seeds enhance proliferation of normal human cultured melanocytes: GC–MS profiling and biological investigation
  23. A novel electrochemical micro-titration method for quantitative evaluation of the DPPH free radical scavenging capacity of caffeic acid
  24. Comparative study between supported bimetallic catalysts for nitrate remediation in water
  25. Persicaline, an alkaloid from Salvadora persica, inhibits proliferation and induces apoptosis and cell-cycle arrest in MCF-7 cells
  26. Determination of nicotine content in locally produced smokeless tobacco (Shammah) samples from Jazan region of Saudi Arabia using a convenient HPLC-MS/MS method
  27. Changes in oxidative stress markers in pediatric burn injury over a 1-week period
  28. Integrated geophysical techniques applied for petroleum basins structural characterization in the central part of the Western Desert, Egypt
  29. The impact of chemical modifications on gamma-ray attenuation properties of some WO3-reinforced tellurite glasses
  30. Microwave and Cs+-assisted chemo selective reaction protocol for synthesizing 2-styryl quinoline biorelevant molecules
  31. Structural, physical, and radiation absorption properties of a significant nuclear power plant component: A comparison between REX-734 and 316L SS austenitic stainless steels
  32. Effect of Moringa oleifera on serum YKL-40 level: In vivo rat periodontitis model
  33. Investigating the impact of CO2 emissions on the COVID-19 pandemic by generalized linear mixed model approach with inverse Gaussian and gamma distributions
  34. Influence of WO3 content on gamma rays attenuation characteristics of phosphate glasses at low energy range
  35. Study on CO2 absorption performance of ternary DES formed based on DEA as promoting factor
  36. Performance analyses of detonation engine cogeneration cycles
  37. Sterols from Centaurea pumilio L. with cell proliferative activity: In vitro and in silico studies
  38. Untargeted metabolomics revealing changes in aroma substances in flue-cured tobacco
  39. Effect of pumpkin enriched with calcium lactate on iron status in an animal model of postmenopausal osteoporosis
  40. Energy consumption, mechanical and metallographic properties of cryogenically treated tool steels
  41. Optimization of ultra-high pressure-assisted extraction of total phenols from Eucommia ulmoides leaves by response surface methodology
  42. Harpin enhances antioxidant nutrient accumulation and decreases enzymatic browning in stored soybean sprouts
  43. Physicochemical and biological properties of carvacrol
  44. Radix puerariae in the treatment of diabetic nephropathy: A network pharmacology analysis and experimental validation
  45. Anti-Alzheimer, antioxidants, glucose-6-phosphate dehydrogenase effects of Taverniera glabra mediated ZnO and Fe2O3 nanoparticles in alloxan-induced diabetic rats
  46. Experimental study on photocatalytic CO2 reduction performance of ZnS/CdS-TiO2 nanotube array thin films
  47. Epoxy-reinforced heavy metal oxides for gamma ray shielding purposes
  48. Black mulberry (Morus nigra L.) fruits: As a medicinal plant rich in human health-promoting compounds
  49. Promising antioxidant and antimicrobial effects of essential oils extracted from fruits of Juniperus thurifera: In vitro and in silico investigations
  50. Chloramine-T-induced oxidation of Rizatriptan Benzoate: An integral chemical and spectroscopic study of products, mechanisms and kinetics
  51. Study on antioxidant and antimicrobial potential of chemically profiled essential oils extracted from Juniperus phoenicea (L.) by use of in vitro and in silico approaches
  52. Screening and characterization of fungal taxol-producing endophytic fungi for evaluation of antimicrobial and anticancer activities
  53. Mineral composition, principal polyphenolic components, and evaluation of the anti-inflammatory, analgesic, and antioxidant properties of Cytisus villosus Pourr leaf extracts
  54. In vitro antiproliferative efficacy of Annona muricata seed and fruit extracts on several cancer cell lines
  55. An experimental study for chemical characterization of artificial anterior cruciate ligament with coated chitosan as biomaterial
  56. Prevalence of residual risks of the transfusion-transmitted infections in Riyadh hospitals: A two-year retrospective study
  57. Computational and experimental investigation of antibacterial and antifungal properties of Nicotiana tabacum extracts
  58. Reinforcement of cementitious mortars with hemp fibers and shives
  59. X-ray shielding properties of bismuth-borate glass doped with rare earth ions
  60. Green supported silver nanoparticles over modified reduced graphene oxide: Investigation of its antioxidant and anti-ovarian cancer effects
  61. Orthogonal synthesis of a versatile building block for dual functionalization of targeting vectors
  62. Thymbra spicata leaf extract driven biogenic synthesis of Au/Fe3O4 nanocomposite and its bio-application in the treatment of different types of leukemia
  63. The role of Ag2O incorporation in nuclear radiation shielding behaviors of the Li2O–Pb3O4–SiO2 glass system: A multi-step characterization study
  64. A stimuli-responsive in situ spray hydrogel co-loaded with naringenin and gentamicin for chronic wounds
  65. Assessment of the impact of γ-irradiation on the piperine content and microbial quality of black pepper
  66. Antioxidant, sensory, and functional properties of low-alcoholic IPA beer with Pinus sylvestris L. shoots addition fermented using unconventional yeast
  67. Screening and optimization of extracellular pectinase produced by Bacillus thuringiensis SH7
  68. Determination of polyphenols in Chinese jujube using ultra-performance liquid chromatography–mass spectrometry
  69. Synergistic effects of harpin and NaCl in determining soybean sprout quality under non-sterile conditions
  70. Field evaluation of different eco-friendly alternative control methods against Panonychus citri [Acari: Tetranychidae] spider mite and its predators in citrus orchards
  71. Exploring the antimicrobial potential of biologically synthesized zero valent iron nanoparticles
  72. NaCl regulates goldfish growth and survival at three food supply levels under hypoxia
  73. An exploration of the physical, optical, mechanical, and radiation shielding properties of PbO–MgO–ZnO–B2O3 glasses
  74. A novel statistical modeling of air pollution and the COVID-19 pandemic mortality data by Poisson, geometric, and negative binomial regression models with fixed and random effects
  75. Treatment activity of the injectable hydrogels loaded with dexamethasone In(iii) complex on glioma by inhibiting the VEGF signaling pathway
  76. An alternative approach for the excess lifetime cancer risk and prediction of radiological parameters
  77. Panax ginseng leaf aqueous extract mediated green synthesis of AgNPs under ultrasound condition and investigation of its anti-lung adenocarcinoma effects
  78. Study of hydrolysis and production of instant ginger (Zingiber officinale) tea
  79. Novel green synthesis of zinc oxide nanoparticles using Salvia rosmarinus extract for treatment of human lung cancer
  80. Evaluation of second trimester plasma lipoxin A4, VEGFR-1, IL-6, and TNF-α levels in pregnant women with gestational diabetes mellitus
  81. Antidiabetic, antioxidant and cytotoxicity activities of ortho- and para-substituted Schiff bases derived from metformin hydrochloride: Validation by molecular docking and in silico ADME studies
  82. Antioxidant, antidiabetic, antiglaucoma, and anticholinergic effects of Tayfi grape (Vitis vinifera): A phytochemical screening by LC-MS/MS analysis
  83. Identification of genetic polymorphisms in the stearoyl CoA desaturase gene and its association with milk quality traits in Najdi sheep
  84. Cold-acclimation effect on cadmium absorption and biosynthesis of polyphenolics, and free proline and photosynthetic pigments in Spirogyra aequinoctialis
  85. Analysis of secondary metabolites in Xinjiang Morus nigra leaves using different extraction methods with UPLC-Q/TOF-MS/MS technology
  86. Nanoarchitectonics and performance evaluation of a Fe3O4-stabilized Pickering emulsion-type differential pressure plugging agent
  87. Investigating pyrolysis characteristics of Shengdong coal through Py-GC/MS
  88. Extraction, phytochemical characterization, and antifungal activity of Salvia rosmarinus extract
  89. Introducing a novel and natural antibiotic for the treatment of oral pathogens: Abelmoschus esculentus green-formulated silver nanoparticles
  90. Optimization of gallic acid-enriched ultrasonic-assisted extraction from mango peels
  91. Effect of gamma rays irradiation in the structure, optical, and electrical properties of samarium doped bismuth titanate ceramics
  92. Combinatory in silico investigation for potential inhibitors from Curcuma sahuynhensis Škorničk. & N.S. Lý volatile phytoconstituents against influenza A hemagglutinin, SARS-CoV-2 main protease, and Omicron-variant spike protein
  93. Physical, mechanical, and gamma ray shielding properties of the Bi2O3–BaO–B2O3–ZnO–As2O3–MgO–Na2O glass system
  94. Twofold interpenetrated 3D Cd(ii) complex: Crystal structure and luminescent property
  95. Study on the microstructure and soil quality variation of composite soil with soft rock and sand
  96. Ancient spring waters still emerging and accessible in the Roman Forum area: Chemical–physical and microbiological characterization
  97. Extraction and characterization of type I collagen from scales of Mexican Biajaiba fish
  98. Finding small molecular compounds to decrease trimethylamine oxide levels in atherosclerosis by virtual screening
  99. Prefatory in silico studies and in vitro insecticidal effect of Nigella sativa (L.) essential oil and its active compound (carvacrol) against the Callosobruchus maculatus adults (Fab), a major pest of chickpea
  100. Polymerized methyl imidazole silver bromide (CH3C6H5AgBr)6: Synthesis, crystal structures, and catalytic activity
  101. Using calcined waste fish bones as a green solid catalyst for biodiesel production from date seed oil
  102. Influence of the addition of WO3 on TeO2–Na2O glass systems in view of the feature of mechanical, optical, and photon attenuation
  103. Naringin ameliorates 5-fluorouracil elicited neurotoxicity by curtailing oxidative stress and iNOS/NF-ĸB/caspase-3 pathway
  104. GC-MS profile of extracts of an endophytic fungus Alternaria and evaluation of its anticancer and antibacterial potentialities
  105. Green synthesis, chemical characterization, and antioxidant and anti-colorectal cancer effects of vanadium nanoparticles
  106. Determination of caffeine content in coffee drinks prepared in some coffee shops in the local market in Jeddah City, Saudi Arabia
  107. A new 3D supramolecular Cu(ii) framework: Crystal structure and photocatalytic characteristics
  108. Bordeaux mixture accelerates ripening, delays senescence, and promotes metabolite accumulation in jujube fruit
  109. Important application value of injectable hydrogels loaded with omeprazole Schiff base complex in the treatment of pancreatitis
  110. Color tunable benzothiadiazole-based small molecules for lightening applications
  111. Investigation of structural, dielectric, impedance, and mechanical properties of hydroxyapatite-modified barium titanate composites for biomedical applications
  112. Metal gel particles loaded with epidermal cell growth factor promote skin wound repair mechanism by regulating miRNA
  113. In vitro exploration of Hypsizygus ulmarius (Bull.) mushroom fruiting bodies: Potential antidiabetic and anti-inflammatory agent
  114. Alteration in the molecular structure of the adenine base exposed to gamma irradiation: An ESR study
  115. Comprehensive study of optical, thermal, and gamma-ray shielding properties of Bi2O3–ZnO–PbO–B2O3 glasses
  116. Lewis acids as co-catalysts in Pd-based catalyzed systems of the octene-1 hydroethoxycarbonylation reaction
  117. Synthesis, Hirshfeld surface analysis, thermal, and selective α-glucosidase inhibitory studies of Schiff base transition metal complexes
  118. Protective properties of AgNPs green-synthesized by Abelmoschus esculentus on retinal damage on the virtue of its anti-inflammatory and antioxidant effects in diabetic rat
  119. Effects of green decorated AgNPs on lignin-modified magnetic nanoparticles mediated by Cydonia on cecal ligation and puncture-induced sepsis
  120. Treatment of gastric cancer by green mediated silver nanoparticles using Pistacia atlantica bark aqueous extract
  121. Preparation of newly developed porcelain ceramics containing WO3 nanoparticles for radiation shielding applications
  122. Utilization of computational methods for the identification of new natural inhibitors of human neutrophil elastase in inflammation therapy
  123. Some anticancer agents as effective glutathione S-transferase (GST) inhibitors
  124. Clay-based bricks’ rich illite mineral for gamma-ray shielding applications: An experimental evaluation of the effect of pressure rates on gamma-ray attenuation parameters
  125. Stability kinetics of orevactaene pigments produced by Epicoccum nigrum in solid-state fermentation
  126. Treatment of denture stomatitis using iron nanoparticles green-synthesized by Silybum marianum extract
  127. Characterization and antioxidant potential of white mustard (Brassica hirta) leaf extract and stabilization of sunflower oil
  128. Characteristics of Langmuir monomolecular monolayers formed by the novel oil blends
  129. Strategies for optimizing the single GdSrFeO4 phase synthesis
  130. Oleic acid and linoleic acid nanosomes boost immunity and provoke cell death via the upregulation of beta-defensin-4 at genetic and epigenetic levels
  131. Unraveling the therapeutic potential of Bombax ceiba roots: A comprehensive study of chemical composition, heavy metal content, antibacterial activity, and in silico analysis
  132. Green synthesis of AgNPs using plant extract and investigation of its anti-human colorectal cancer application
  133. The adsorption of naproxen on adsorbents obtained from pepper stalk extract by green synthesis
  134. Treatment of gastric cancer by silver nanoparticles encapsulated by chitosan polymers mediated by Pistacia atlantica extract under ultrasound condition
  135. In vitro protective and anti-inflammatory effects of Capparis spinosa and its flavonoids profile
  136. Wear and corrosion behavior of TiC and WC coatings deposited on high-speed steels by electro-spark deposition
  137. Therapeutic effects of green-formulated gold nanoparticles by Origanum majorana on spinal cord injury in rats
  138. Melanin antibacterial activity of two new strains, SN1 and SN2, of Exophiala phaeomuriformis against five human pathogens
  139. Evaluation of the analgesic and anesthetic properties of silver nanoparticles supported over biodegradable acacia gum-modified magnetic nanoparticles
  140. Review Articles
  141. Role and mechanism of fruit waste polyphenols in diabetes management
  142. A comprehensive review of non-alkaloidal metabolites from the subfamily Amaryllidoideae (Amaryllidaceae)
  143. Discovery of the chemical constituents, structural characteristics, and pharmacological functions of Chinese caterpillar fungus
  144. Eco-friendly green approach of nickel oxide nanoparticles for biomedical applications
  145. Advances in the pharmaceutical research of curcumin for oral administration
  146. Rapid Communication
  147. Determination of the contents of bioactive compounds in St. John’s wort (Hypericum perforatum): Comparison of commercial and wild samples
  148. Retraction
  149. Retraction of “Two mixed-ligand coordination polymers based on 2,5-thiophenedicarboxylic acid and flexible N-donor ligands: The protective effect on periodontitis via reducing the release of IL-1β and TNF-α”
  150. Topical Issue on Phytochemicals, biological and toxicological analysis of aromatic medicinal plants
  151. Anti-plasmodial potential of selected medicinal plants and a compound Atropine isolated from Eucalyptus obliqua
  152. Anthocyanin extract from black rice attenuates chronic inflammation in DSS-induced colitis mouse model by modulating the gut microbiota
  153. Evaluation of antibiofilm and cytotoxicity effect of Rumex vesicarius methanol extract
  154. Chemical compositions of Litsea umbellata and inhibition activities
  155. Green synthesis, characterization of silver nanoparticles using Rhynchosia capitata leaf extract and their biological activities
  156. GC-MS analysis and antibacterial activities of some plants belonging to the genus Euphorbia on selected bacterial isolates
  157. The abrogative effect of propolis on acrylamide-induced toxicity in male albino rats: Histological study
  158. A phytoconstituent 6-aminoflavone ameliorates lipopolysaccharide-induced oxidative stress mediated synapse and memory dysfunction via p-Akt/NF-kB pathway in albino mice
  159. Anti-diabetic potentials of Sorbaria tomentosa Lindl. Rehder: Phytochemistry (GC-MS analysis), α-amylase, α-glucosidase inhibitory, in vivo hypoglycemic, and biochemical analysis
  160. Assessment of cytotoxic and apoptotic activities of the Cassia angustifolia aqueous extract against SW480 colon cancer
  161. Biochemical analysis, antioxidant, and antibacterial efficacy of the bee propolis extract (Hymenoptera: Apis mellifera) against Staphylococcus aureus-induced infection in BALB/c mice: In vitro and in vivo study
  162. Assessment of essential elements and heavy metals in Saudi Arabian rice samples underwent various processing methods
  163. Two new compounds from leaves of Capparis dongvanensis (Sy, B. H. Quang & D. V. Hai) and inhibition activities
  164. Hydroxyquinoline sulfanilamide ameliorates STZ-induced hyperglycemia-mediated amyleoid beta burden and memory impairment in adult mice
  165. An automated reading of semi-quantitative hemagglutination results in microplates: Micro-assay for plant lectins
  166. Inductively coupled plasma mass spectrometry assessment of essential and toxic trace elements in traditional spices consumed by the population of the Middle Eastern region in their recipes
  167. Phytochemical analysis and anticancer activity of the Pithecellobium dulce seed extract in colorectal cancer cells
  168. Impact of climatic disturbances on the chemical compositions and metabolites of Salvia officinalis
  169. Physicochemical characterization, antioxidant and antifungal activities of essential oils of Urginea maritima and Allium sativum
  170. Phytochemical analysis and antifungal efficiency of Origanum majorana extracts against some phytopathogenic fungi causing tomato damping-off diseases
  171. Special Issue on 4th IC3PE
  172. Graphene quantum dots: A comprehensive overview
  173. Studies on the intercalation of calcium–aluminium layered double hydroxide-MCPA and its controlled release mechanism as a potential green herbicide
  174. Synergetic effect of adsorption and photocatalysis by zinc ferrite-anchored graphitic carbon nitride nanosheet for the removal of ciprofloxacin under visible light irradiation
  175. Exploring anticancer activity of the Indonesian guava leaf (Psidium guajava L.) fraction on various human cancer cell lines in an in vitro cell-based approach
  176. The comparison of gold extraction methods from the rock using thiourea and thiosulfate
  177. Special Issue on Marine environmental sciences and significance of the multidisciplinary approaches
  178. Sorption of alkylphenols and estrogens on microplastics in marine conditions
  179. Cytotoxic ketosteroids from the Red Sea soft coral Dendronephthya sp.
  180. Antibacterial and biofilm prevention metabolites from Acanthophora spicifera
  181. Characteristics, source, and health risk assessment of aerosol polyaromatic hydrocarbons in the rural and urban regions of western Saudi Arabia
  182. Special Issue on Advanced Nanomaterials for Energy, Environmental and Biological Applications - Part II
  183. Green synthesis, characterization, and evaluation of antibacterial activities of cobalt nanoparticles produced by marine fungal species Periconia prolifica
  184. Combustion-mediated sol–gel preparation of cobalt-doped ZnO nanohybrids for the degradation of acid red and antibacterial performance
  185. Perinatal supplementation with selenium nanoparticles modified with ascorbic acid improves hepatotoxicity in rat gestational diabetes
  186. Evaluation and chemical characterization of bioactive secondary metabolites from endophytic fungi associated with the ethnomedicinal plant Bergenia ciliata
  187. Enhancing photovoltaic efficiency with SQI-Br and SQI-I sensitizers: A comparative analysis
  188. Nanostructured p-PbS/p-CuO sulfide/oxide bilayer heterojunction as a promising photoelectrode for hydrogen gas generation
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