PL446048A1 - Method for catalytic synthesis of 1,3-dioxolane derivatives and a catalyst for carrying out this method - Google Patents

Method for catalytic synthesis of 1,3-dioxolane derivatives and a catalyst for carrying out this method

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Publication number
PL446048A1
PL446048A1 PL446048A PL44604823A PL446048A1 PL 446048 A1 PL446048 A1 PL 446048A1 PL 446048 A PL446048 A PL 446048A PL 44604823 A PL44604823 A PL 44604823A PL 446048 A1 PL446048 A1 PL 446048A1
Authority
PL
Poland
Prior art keywords
catalyst
ketone
polyalcohol
reactor
reaction mixture
Prior art date
Application number
PL446048A
Other languages
Polish (pl)
Other versions
PL248119B1 (en
Inventor
Maciej Kapkowski
Karina Kocot
Original Assignee
Uniwersytet Śląski W Katowicach
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Uniwersytet Śląski W Katowicach filed Critical Uniwersytet Śląski W Katowicach
Priority to PL446048A priority Critical patent/PL248119B1/en
Publication of PL446048A1 publication Critical patent/PL446048A1/en
Publication of PL248119B1 publication Critical patent/PL248119B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/08—Silica
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/08—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of gallium, indium or thallium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/20—Free hydroxyl or mercaptan

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Przedmiotem zgłoszenia jest sposób katalitycznej syntezy pochodnych 1,3-dioksolanu o strukturze przedstawionej na wzorze ogólnym 1, w którym poszczególne podstawniki R1, R2, R3, R4 oznaczają niezależnie od siebie atom wodoru lub grupę metylową lub grupę etylową lub grupę hydroksymetylową, polegający na tym, że do reaktora wprowadza się heterogeniczny katalizator, polialkohol oraz keton, dobierając ilości składników tak, by stężenie masowe katalizatora w mieszaninie reakcyjnej mieściło się w zakresie od 0,8 mg/mL do 10,5 mg/mL, natomiast stosunek molowy polialkoholu do ketonu był równomolowy lub korzystniej z nadmiarem ketonu, przy czym: jako katalizator stosuje się nośnik z dwutlenku krzemu z naniesioną na nim warstwą aktywną nanocząstek indu, przy czym stężenie nanocząstek indu w masie całego katalizatora wynosi od 0,05% wag. do 4,0% wag., a katalizator ma postać sypkiego proszku albo granulatu, jako polialkohol stosuje się poliol wybrany spośród: glikol propylenowy, glikol etylenowy, gliceryna, jako keton stosuje się 2-butanon albo 3-pentanon albo 1-hydroksyaceton albo 1,3-dihydroksyaceton albo najkorzystniej aceton, następnie reaktor zamyka się, a w kolejnym etapie mieszaninę reakcyjną poddaje się działaniu temperatury o wartości od 25°C do 80°C, w czasie od 5 minut do 150 minut, mieszając jednocześnie reagenty z prędkością od 150 do 300 obr./min, następnie oddziela się katalizator, a z otrzymanej mieszaniny poreakcyjnej, od produktów ubocznych stanowiących pośrednie produkty niedomknięcia pierścienia wydziela się produkty główne, to jest cykliczne ketale, przy czym w wariancie z katalizatorem w postaci sypkiego proszku, po wprowadzeniu składników do reaktora, a przed jego zamknięciem realizuje się proces zawieszenia katalizatora w mieszaninie reakcyjnej. Istotę wynalazku stanowi również katalizator użyty w opisanym sposobie.The subject of the application is a method of catalytic synthesis of 1,3-dioxolane derivatives with the structure presented in general formula 1, wherein the individual substituents R1, R2, R3, R4 independently of each other are a hydrogen atom or a methyl group or an ethyl group or a hydroxymethyl group, consisting in introducing a heterogeneous catalyst, a polyalcohol and a ketone into the reactor, selecting the amounts of components so that the mass concentration of the catalyst in the reaction mixture is in the range from 0.8 mg/mL to 10.5 mg/mL, while the molar ratio of the polyalcohol to the ketone is equimolar or, more preferably, with an excess of ketone, wherein: a silicon dioxide support with an active layer of indium nanoparticles deposited on it is used as the catalyst, wherein the concentration of indium nanoparticles in the mass of the entire catalyst is from 0.05 wt.%. up to 4.0% by weight, and the catalyst is in the form of a loose powder or granulate, a polyol selected from the following is used as the polyalcohol: propylene glycol, ethylene glycol, glycerine, 2-butanone or 3-pentanone or 1-hydroxyacetone or 1,3-dihydroxyacetone or, most preferably, acetone is used as the ketone, then the reactor is closed, and in the next stage the reaction mixture is subjected to a temperature of 25°C to 80°C for 5 minutes to 150 minutes, while mixing the reagents at a speed of 150 to 300 rpm, then the catalyst is separated, and the main products, i.e. cyclic ketals, are separated from the by-products constituting the intermediate products of ring failure, wherein in the variant with a loose powder catalyst, after introducing the components into the reactor and before closing it, the suspension process is carried out catalyst in the reaction mixture. The essence of the invention is also the catalyst used in the described method.

PL446048A 2023-09-07 2023-09-07 A method for the catalytic synthesis of 1,3-dioxolane derivatives and a catalyst for carrying out this method PL248119B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL446048A PL248119B1 (en) 2023-09-07 2023-09-07 A method for the catalytic synthesis of 1,3-dioxolane derivatives and a catalyst for carrying out this method

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL446048A PL248119B1 (en) 2023-09-07 2023-09-07 A method for the catalytic synthesis of 1,3-dioxolane derivatives and a catalyst for carrying out this method

Publications (2)

Publication Number Publication Date
PL446048A1 true PL446048A1 (en) 2025-03-10
PL248119B1 PL248119B1 (en) 2025-10-20

Family

ID=94868625

Family Applications (1)

Application Number Title Priority Date Filing Date
PL446048A PL248119B1 (en) 2023-09-07 2023-09-07 A method for the catalytic synthesis of 1,3-dioxolane derivatives and a catalyst for carrying out this method

Country Status (1)

Country Link
PL (1) PL248119B1 (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL229330B1 (en) * 2016-02-01 2018-07-31 Politechnika Slaska Im Wincent Method for obtaining a cyclic acetals in the reaction of alcohols with ketones
PL238647B1 (en) * 2017-10-27 2021-09-20 Univ Slaski Method for obtaining cyclic acetals or their mixes and their application as fuel additives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL229330B1 (en) * 2016-02-01 2018-07-31 Politechnika Slaska Im Wincent Method for obtaining a cyclic acetals in the reaction of alcohols with ketones
PL238647B1 (en) * 2017-10-27 2021-09-20 Univ Slaski Method for obtaining cyclic acetals or their mixes and their application as fuel additives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
E. RAMOS-RAMIREZ, G. RANGEL-PORRAS, T. LÓPEZ-GOERNE: "Emerging Fields in Sol-Gel Science and Technology, 2003, 203-210", SILICA OBTAINED BY SOL-GEL PROCESSING AND MODIFIED THROUGH INDIUM INCORPORATION *

Also Published As

Publication number Publication date
PL248119B1 (en) 2025-10-20

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