Aliphatic Dicarboxylic Acids From Oil Shale Organic Matter ‒ Historic Review

Veski, R.; Veski, Siim

doi:10.3176/oil.2019.1.06

Cited by 8 publications

(12 citation statements)

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“…3 Its primary use is in the production of nylon-6,6 with a global market size of 3.7 million tons per annum. 4 The current manufacturing of adipic acid depends on petroleum-derived chemicals and emits nitrous oxide (N 2 O). 5 One promising route to renewable adipic acid is from biomassderived C6 carbohydrates.…”

Section: Introductionmentioning

confidence: 99%

A Heterogeneous Pt-ReO_x/C Catalyst for Making Renewable Adipates in One Step from Sugar Acids

Jang¹,

Christopher³

et al. 2020

ACS Catal.

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Renewable adipic acid is a value-added chemical for the production of bioderived nylon. Here, the one-step conversion of mucic acid to adipates was achieved in high yield through deoxydehydration (DODH) and catalytic transfer hydrogenation (CTH) by a bifunctional Pt-ReO x /C heterogeneous catalyst with isopropanol as solvent and reductant. The Pt-ReO x /C catalyst is reusable and was regenerated at least five times. The catalyst exhibits a broad substrate scope of various diols. Spectroscopic studies of Pt-ReO x /C revealed Re VII and Pt 0 as the relevant species for DODH and CTH, respectively. Isotope labeling experiments support a monohydride mechanism for CTH over Pt. This work demonstrates a reusable bifunctional catalyst for a one-step valorization of sugar acids to a practical monomer, which opens the door to multifunctional catalysis streamlining valorization of biomass-derived molecules.

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Section: Introductionmentioning

confidence: 99%

A Heterogeneous Pt-ReO_x/C Catalyst for Making Renewable Adipates in One Step from Sugar Acids

Jang¹,

Christopher³

et al. 2020

ACS Catal.

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“…17 − 19 The developed process, however, was never industrially implemented. 15 In 2001, Bajc et al 20 investigated DCA formation with an alkaline permanganate oxidation method using a 33-step process on a laboratory-scale synthesis. They obtained 40% of different oxidation products (w/w on kerogen), of which 52% were aliphatic DCAs.…”

Section: Introductionmentioning

confidence: 99%

Wet Air Oxidation of Oil Shales: Kerogen Dissolution and Dicarboxylic Acid Formation

et al. 2020

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Until now, the oil shale kukersite has been used mainly for energy and oil production. To broaden the possible applications of oil shales, the wet air oxidation of kukersite (an organic-rich sedimentary rock from Estonia) was studied. Kukersite was oxidized with an oxygen-rich gas in water at temperatures up to 200 °C and pressures up to 60 bar. The efficiency of this batch process was evaluated from organic matter conversion, from the amount of solubilized organics obtained, and from the rate of dicarboxylic acid (DCA) formation. The effect of several reaction parameters—pressure, temperature, time, acid/base additives, substrate concentration, the origin of a substrate and its organic matter content, and so forth—was measured. A conversion of 91% in total organic carbon was achieved at 175 °C with 40 bar of the 1:1 oxygen/nitrogen mixture in 3 h without the presence of any additives. Under basic conditions, high yields (up to 50%) of dissolved organic matter were obtained with 8% of DCA; the best results are obtained with K 2 CO 3 and KOH. The highest DCA outcome (12%) within the 3 h reaction time was obtained in the presence of acetic acid. It was found that temperatures higher than 185 °C, pressures over 30 bar of pO 2 , and long reaction times in the acidic media caused a considerable decrease in the DCA outcome. It was also found that the same process can be applied to shales of different origins, although with lower DCA yields.

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“…The commercial value of organic compounds from oil shale organic matter (kerogen) may be several times higher than that from the current use of oil shale (e.g. shale oil and phenols) [12,13].…”

Section: Introductionmentioning

confidence: 99%

“…It has been shown previously that up to 40% of the kerogen in Kukersite is convertible to a mixture of aliphatic dicarboxylic acids (DCAs) by using oxidative conditions [13,14]. Various processes, such as oxidation with nitric acid [13,[15][16][17] or potassium permanganate [18][19][20], as well as use of a continuous flow of air fed through basic aqueous solutions [21][22][23] have been examined. Unfortunately, most of the cited works date back more than 50 years, and thus there is a lack of information on whether these applications are feasible in a modern industrial environment.…”

Section: Introductionmentioning

confidence: 99%

Aspects of kerogen oxidative dissolution in subcritical water using oxygen from air

Kaldas¹,

Lopp²,

Muldma³

et al. 2021

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Society's growing demands on everyday products and materials are increasingly difficult to meet in an environment that seeks to avoid petroleumbased processes. Instead of abandoning fossil materials altogether, more research should be done on their efficient and clean conversion. One option for this is the oxidative dissolution of kerogen in water under conditions that satisfy the subcritical range (T = 150-200 °C, pO 2 = 0.5-4 MPa). The resulting mixture contains a substantial amount of various aliphatic carboxylic and dicarboxylic acids. Both batch and semi-continuous processes were set up to find the main factors and optimal conditions for the kerogen dissolution process. The rate of transformation of organic carbon to dissolved organic compounds was mainly influenced by elevated temperature and oxygen partial pressure. To obtain high yields of organic carbon dissolution and to avoid the formation of excess CO 2 , the oxidation of kerogen should be carried out fast (< 1 h) and under high oxygen pressure. By employing a temperature of 175 °C and O 2 pressure of 2 MPa, over 65% of the initial organic carbon dissolves in about one hour. Prolonged reaction times or harsher oxidation conditions resulted in a rapid degradation of dissolved matter and also of the valuable products formed. The organic matter content of the initial oil shale had a direct effect on the further degradation of dicarboxylic acid and consequently on the overall yield. The suitability of using a trickle-bed reactor for kerogen dissolution is discussed in detail on the basis of experimental results.

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Aliphatic Dicarboxylic Acids From Oil Shale Organic Matter ‒ Historic Review

Cited by 8 publications

References 0 publications

A Heterogeneous Pt-ReO_x/C Catalyst for Making Renewable Adipates in One Step from Sugar Acids

A Heterogeneous Pt-ReO_x/C Catalyst for Making Renewable Adipates in One Step from Sugar Acids

Wet Air Oxidation of Oil Shales: Kerogen Dissolution and Dicarboxylic Acid Formation

Aspects of kerogen oxidative dissolution in subcritical water using oxygen from air

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Aliphatic Dicarboxylic Acids From Oil Shale Organic Matter ‒ Historic Review

Cited by 8 publications

References 0 publications

A Heterogeneous Pt-ReOx/C Catalyst for Making Renewable Adipates in One Step from Sugar Acids

A Heterogeneous Pt-ReOx/C Catalyst for Making Renewable Adipates in One Step from Sugar Acids

Wet Air Oxidation of Oil Shales: Kerogen Dissolution and Dicarboxylic Acid Formation

Aspects of kerogen oxidative dissolution in subcritical water using oxygen from air

Contact Info

Product

Resources

About

A Heterogeneous Pt-ReO_x/C Catalyst for Making Renewable Adipates in One Step from Sugar Acids

A Heterogeneous Pt-ReO_x/C Catalyst for Making Renewable Adipates in One Step from Sugar Acids