PL448583A1 - Sposób otrzymywania poliolu z oleju roślinnego, poliol otrzymany tym sposobem i sposób wytwarzania pianki poliuretanowej - Google Patents

Sposób otrzymywania poliolu z oleju roślinnego, poliol otrzymany tym sposobem i sposób wytwarzania pianki poliuretanowej

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Publication number
PL448583A1
PL448583A1 PL448583A PL44858324A PL448583A1 PL 448583 A1 PL448583 A1 PL 448583A1 PL 448583 A PL448583 A PL 448583A PL 44858324 A PL44858324 A PL 44858324A PL 448583 A1 PL448583 A1 PL 448583A1
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Poland
Prior art keywords
polyol
vegetable oil
mixture
organic layer
oil
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PL448583A
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English (en)
Inventor
Anna Smagowicz
Henryk Pawlik
Henryk Wojdyła
Mirosław Płocieniak
Michał Kacperski
Łukasz Makuła
Michał Salasa
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Pcc Rokita Spółka Akcyjna
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Priority to PL448583A priority Critical patent/PL448583A1/pl
Priority to EP25176486.6A priority patent/EP4650378A1/en
Publication of PL448583A1 publication Critical patent/PL448583A1/pl

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
    • C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
    • C08G18/165—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22 covered by C08G18/18 and C08G18/24
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1833—Catalysts containing secondary or tertiary amines or salts thereof having ether, acetal, or orthoester groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
    • C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4288—Polycondensates having carboxylic or carbonic ester groups in the main chain modified by higher fatty oils or their acids or by resin acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/4808—Mixtures of two or more polyetherdiols
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/6696—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0008—Foam properties flexible
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0041—Foam properties having specified density
    • C08G2110/005—< 50kg/m3
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0083—Foam properties prepared using water as the sole blowing agent

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Zgłoszenie dotyczy sposobu otrzymywania poliolu o obniżonej zawartości nukleofila z oleju roślinnego, w którym dostarcza się mieszaninę zawierającą olej roślinny oraz mieszaninę kwasów: 80% kwas octowy i 95% - 98% kwas siarkowy(VI) w proporcjach wagowych odpowiednio 6:1; epoksydacja mieszaniny z etapu a) poprzez dodawanie nadtlenku wodoru przez 90 do 120 minut tak, w stałej temperaturze reakcji 50°C - 65°C i mieszanie kontynuowane jest przez 2 do 6 godzin od zakończenia wprowadzania nadtlenku wodoru; oddzielenie warstwy organicznej zawierającej epoksydowany olej z etapu b) i osuszanie jej poprzez ogrzewanie jej do temperatury 80°C - 90°C pod ciśnieniem poniżej zera manometrycznego z jednoczesnym barbotażem inertnego gazu; kontaktowanie w obecności kwaśnego katalizatora epoksydowanego oleju roślinnego z etapu b) z nukleofilem stosowanym w ilości 0,7 — 1,1 mol. w stosunku do zawartości grup epoksydowych w oleju; neutralizacja mieszaniny z etapu d), następnie przemywanie jej wodą i oddzielenie warstwy organicznej od warstwy wodnej; osuszanie warstwy organicznej poprzez ogrzanie jej do temperatury 80°C - 90°C pod obniżonym ciśnieniem, poniżej zera manometrycznego, z jednoczesnym barbotażem inertnego gazu i następnie odfiltrowanie wytrąconych soli od produktu. Zgłoszenie dotyczy również sposobu wytwarzania pianki poliuretanowej zawierającej ten poliol.
PL448583A 2024-05-16 2024-05-16 Sposób otrzymywania poliolu z oleju roślinnego, poliol otrzymany tym sposobem i sposób wytwarzania pianki poliuretanowej PL448583A1 (pl)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PL448583A PL448583A1 (pl) 2024-05-16 2024-05-16 Sposób otrzymywania poliolu z oleju roślinnego, poliol otrzymany tym sposobem i sposób wytwarzania pianki poliuretanowej
EP25176486.6A EP4650378A1 (en) 2024-05-16 2025-05-14 Method of obtaining polyol from vegetable oil, polyol obtained by this method and its use for polyurethane foam

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PL448583A PL448583A1 (pl) 2024-05-16 2024-05-16 Sposób otrzymywania poliolu z oleju roślinnego, poliol otrzymany tym sposobem i sposób wytwarzania pianki poliuretanowej

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Citations (3)

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PL206376B1 (pl) * 2005-02-04 2010-08-31 Politechnika Krakowska Sposób otrzymywania składnika poliolowego przeznaczonego do syntezy elastycznych, poliuretanowych materiałów porowatych
PL233221B1 (pl) * 2017-09-18 2019-09-30 Univ Kazimierza Wielkiego W Bydgoszczy Sposób otrzymywania surowca poliolowego do syntezy sztywnych pianek poliuretanowo-poliizocyjanurowych oraz sposób syntezy sztywnych pianek poliuretanowo-poliizocyjanurowych
EP4053111A1 (en) * 2021-03-01 2022-09-07 Komagra Spólka Z O.O. The method of producing epoxidised rapeseed oil and method of producing biopolyol using epoxidised rapeseed oil

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GB739609A (en) 1953-07-13 1955-11-02 Fmc Corp Method of epoxidizing organic esters
GB769127A (en) 1954-03-10 1957-02-27 Fmc Corp Epoxidation of fatty acids
GB790063A (en) 1954-06-09 1958-02-05 Rohm & Haas Method of epoxidizing esters of unsaturated fatty acids
GB811852A (en) 1954-08-30 1959-04-15 Rohm & Haas Method of epoxidation of esters
PL112551B1 (en) 1977-05-21 1980-10-31 Narzedzi Chirurgicznych I Dent Grinding machine
DE3630264A1 (de) 1986-09-05 1988-03-17 Henkel Kgaa Verfahren zur herstellung neuer, massiver polyurethanwerkstoffe im giessverfahren
DE3719790A1 (de) 1987-06-13 1988-12-22 Henkel Kgaa Herstellung von langkettigen polyolen aus nachwachsenden rohstoffen
DE4115146A1 (de) 1991-05-08 1992-11-12 Henkel Kgaa Verfahren zur herstellung von epoxid-ringoeffnungsprodukten mit einem definierten rest-epoxidsauerstoffgehalt
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PL206376B1 (pl) * 2005-02-04 2010-08-31 Politechnika Krakowska Sposób otrzymywania składnika poliolowego przeznaczonego do syntezy elastycznych, poliuretanowych materiałów porowatych
PL233221B1 (pl) * 2017-09-18 2019-09-30 Univ Kazimierza Wielkiego W Bydgoszczy Sposób otrzymywania surowca poliolowego do syntezy sztywnych pianek poliuretanowo-poliizocyjanurowych oraz sposób syntezy sztywnych pianek poliuretanowo-poliizocyjanurowych
EP4053111A1 (en) * 2021-03-01 2022-09-07 Komagra Spólka Z O.O. The method of producing epoxidised rapeseed oil and method of producing biopolyol using epoxidised rapeseed oil

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