PL445536A1 - Mixed esters and the method of obtaining mixtures of mixed esters in the transesterification process of 2-ethylhexyl esters of tere- and orthophthalic and trimellitic acids and their use - Google Patents

Mixed esters and the method of obtaining mixtures of mixed esters in the transesterification process of 2-ethylhexyl esters of tere- and orthophthalic and trimellitic acids and their use

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Publication number
PL445536A1
PL445536A1 PL445536A PL44553623A PL445536A1 PL 445536 A1 PL445536 A1 PL 445536A1 PL 445536 A PL445536 A PL 445536A PL 44553623 A PL44553623 A PL 44553623A PL 445536 A1 PL445536 A1 PL 445536A1
Authority
PL
Poland
Prior art keywords
esters
terephthalate
ethylhexyl
bis
mixture
Prior art date
Application number
PL445536A
Other languages
Polish (pl)
Inventor
Roman Turczyn
Joanna Czogała
Mieczysław Łapkowski
Ewa Pankalla
Original Assignee
Politechnika Śląska
Grupa Azoty Zakłady Azotowe Kędzierzyn Spółka Akcyjna
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 Politechnika Śląska, Grupa Azoty Zakłady Azotowe Kędzierzyn Spółka Akcyjna filed Critical Politechnika Śląska
Priority to PL445536A priority Critical patent/PL445536A1/en
Publication of PL445536A1 publication Critical patent/PL445536A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • B01J23/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of germanium, tin or lead
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters
    • C07C69/82—Terephthalic acid esters

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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)

Abstract

Przedmiotem zgłoszenia są estry mieszane, które charakteryzują się tym, że zawierają co najmniej 87% wag. mieszaniny dwóch estrów: tereftalanu 1-(6-chloroheksylu)-4-(2-etyloheksylu) oraz tereftalanu bis(6-chloroheksylu, a pozostałość stanowi nieprzereagowany ester (tereftalan bis(2-etyloheksylu)). Estry mieszane zawierają co najmniej 41% wag. mieszaniny dwóch estrów: tereftalanu 1-(8-chlorooktylu)-4-(2-etyloheksylu) oraz tereftalanu bis(8-chlorooktylu), a pozostałość stanowi nieprzereagowany ester (tereftalan bis(2-etyloheksylu)). Estry mieszane zawierają co najmniej 93% wag. mieszaniny dwóch estrów: tereftalanu 1-(6-chloroheksylu)-4-(n-butylu) oraz tereftalanu bis(6-chloroheksylu), a pozostałość stanowi nieprzereagowany ester (tereftalan di(n-butylu). Zgłoszenie obejmuje także sposób otrzymywania mieszanin estrów mieszanych, który cechuje się tym, że jako mieszaninę substratów stosuje się jeden z dwóch chloroalkoholi: 6-chloro-1-heksanol lub 8-chloro-1-oktanol oraz jeden z czterech estrów: tereftalan bis(2-etyloheksylu), tereftalan di(n-butylu), ftalanu bis(2-etyloheksylu) albo trimelitanu tris(2-etyloheksylu) w stosunku molowym od 0,5:1 do 4:1 oraz 0,1 - 0,5% wag., katalizatora - związku cynoorganicznego: tlenku dibutylocyny, tlenku dioktylocyny lub dilaurynianu dibutylocyny i tak sporządzony roztwór substratów umieszcza się w naczyniu reakcyjnym, miesza się na mieszadle z szybkością 400 obr./min przez 1 h - 6 h, utrzymując temperaturę 120°C – 140°C oraz ciśnienie w układzie reakcyjnym w zakresie od atmosferycznego (1.013•105 Pa) do 800 Pa. Przedmiotem zgłoszenia jest także zastosowanie mieszaniny estrów do plastyfikacji polichlorku winylu.The subject of the application are mixed esters, which are characterized in that they contain at least 87% by weight. a mixture of two esters: 1-(6-chlorohexyl)-4-(2-ethylhexyl) terephthalate and bis(6-chlorohexyl) terephthalate, and the remainder is the unreacted ester (bis(2-ethylhexyl)). Mixed esters contain at least 41% by weight of a mixture of two esters: 1-(8-chlorooctyl)-4-(2-ethylhexyl) terephthalate and bis(8-chlorooctyl) terephthalate, and the remainder is the unreacted ester (bis(2-ethylhexyl)). Mixed esters contain at least 93% by weight of a mixture of two esters: 1-(6-chlorohexyl)-4-(n-butyl) terephthalate and bis(6-chlorohexyl) terephthalate, and the remainder is the unreacted ester (di(n-butyl) terephthalate). The application also covers a method for obtaining mixed ester mixtures, which is characterized in that one of two chloroalcohols is used as the substrate mixture: 6-chloro-1-hexanol or 8-chloro-1-octanol and one of four esters: bis(2-ethylhexyl) terephthalate, di(n-butyl) terephthalate, bis(2-ethylhexyl) phthalate or tris(2-ethylhexyl) trimellitate in a molar ratio of 0.5:1 to 4:1 and 0.1 - 0.5 wt.% of the catalyst - an organotin compound: dibutyltin oxide, dioctyltin oxide or dibutyltin dilaurate, and the substrate solution prepared in this way is placed in a reaction vessel, stirred on a stirrer at a speed of 400 rpm for 1 h - 6 h, maintaining the temperature of 120°C - 140°C and the pressure in the reaction system in the range from atmospheric (1.013•105 Pa) to 800 Pa. The subject of the application is also the use of a mixture of esters for the plasticization of polyvinyl chloride.

PL445536A 2023-07-07 2023-07-07 Mixed esters and the method of obtaining mixtures of mixed esters in the transesterification process of 2-ethylhexyl esters of tere- and orthophthalic and trimellitic acids and their use PL445536A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL445536A PL445536A1 (en) 2023-07-07 2023-07-07 Mixed esters and the method of obtaining mixtures of mixed esters in the transesterification process of 2-ethylhexyl esters of tere- and orthophthalic and trimellitic acids and their use

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL445536A PL445536A1 (en) 2023-07-07 2023-07-07 Mixed esters and the method of obtaining mixtures of mixed esters in the transesterification process of 2-ethylhexyl esters of tere- and orthophthalic and trimellitic acids and their use

Publications (1)

Publication Number Publication Date
PL445536A1 true PL445536A1 (en) 2025-01-13

Family

ID=94177722

Family Applications (1)

Application Number Title Priority Date Filing Date
PL445536A PL445536A1 (en) 2023-07-07 2023-07-07 Mixed esters and the method of obtaining mixtures of mixed esters in the transesterification process of 2-ethylhexyl esters of tere- and orthophthalic and trimellitic acids and their use

Country Status (1)

Country Link
PL (1) PL445536A1 (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69628923T2 (en) * 1995-04-11 2004-05-27 Great Lakes Chemical Corp., West Lafayette BENZOATE AS A FLAME RETARDANT
US20080004387A1 (en) * 2006-06-30 2008-01-03 Thomas Weiss Alkyl benzyl esters of polycarboxylic acids
WO2016205210A1 (en) * 2015-06-17 2016-12-22 Dover Chemical Corporation Chlorinated ester polyvinyl-chloride secondary plasticizer and related methods
US20170088691A1 (en) * 2015-09-28 2017-03-30 Evonik Degussa Gmbh Tripentyl esters of trimellitic acid

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69628923T2 (en) * 1995-04-11 2004-05-27 Great Lakes Chemical Corp., West Lafayette BENZOATE AS A FLAME RETARDANT
US20080004387A1 (en) * 2006-06-30 2008-01-03 Thomas Weiss Alkyl benzyl esters of polycarboxylic acids
WO2016205210A1 (en) * 2015-06-17 2016-12-22 Dover Chemical Corporation Chlorinated ester polyvinyl-chloride secondary plasticizer and related methods
US20170088691A1 (en) * 2015-09-28 2017-03-30 Evonik Degussa Gmbh Tripentyl esters of trimellitic acid

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