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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PL
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

Applications Claiming Priority (1)

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

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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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Publication number Priority date Publication date Assignee Title
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
DE19503062A1 (de) 1995-02-01 1996-08-08 Henkel Kgaa Verwendung von Alkoxylierungsprodukten epoxydierter Fettstoffe als Entschäumer
US7691914B2 (en) * 2005-04-25 2010-04-06 Cargill, Incorporated Polyurethane foams comprising oligomeric polyols
WO2009140354A1 (en) * 2008-05-13 2009-11-19 Cargill, Incorporated Polyol made from partially hydrogenated, fully epoxidized natural oils
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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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
H. PAWLIK, A. PROCIAK, J. PIELICHOWSKI: "Czasopismo Techniczne. Chemia, 2009, nr 1-Ch, zeszyt 4, str. 111-117", „SYNTEZA POLIOLI Z OLEJU PALNOWEGO PRZEZNACZONYCH DO OTRZYMYWANIA ELASTYCZNYCH PIANEK POLIURETANOWYCH" *

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