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Terephthalate Herstellung Von Di-(2-Ethylhexyl)-Terephthalat Production De Di-(2-Ethylhexyle) Terephthalate

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Terephthalate Herstellung Von Di-(2-Ethylhexyl)-Terephthalat Production De Di-(2-Ethylhexyle) Terephthalate (19) TZZ__ _T (11) EP 1 912 929 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: B01J 31/04 (2006.01) C07C 67/08 (2006.01) 08.01.2014 Bulletin 2014/02 (86) International application number: (21) Application number: 06788502.0 PCT/US2006/028942 (22) Date of filing: 26.07.2006 (87) International publication number: WO 2007/021475 (22.02.2007 Gazette 2007/08) (54) PRODUCTION OF DI-(2-ETHYLHEXYL) TEREPHTHALATE HERSTELLUNG VON DI-(2-ETHYLHEXYL)-TEREPHTHALAT PRODUCTION DE DI-(2-ETHYLHEXYLE) TEREPHTHALATE (84) Designated Contracting States: (56) References cited: AT BE BG CH CY CZ DE DK EE ES FI FR GB GR • DATABASE WPI Week 200142 Derwent HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI Publications Ltd., London, GB; AN 2001-392553 SK TR XP002413852 & JP 2001 031794 A (HOKOKU SEIYU KK) 6 February 2001 (2001-02-06) (30) Priority: 12.08.2005 US 202975 • DATABASECA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; ZENG, (43) Date of publication of application: CHONGYU: "Study on esterification rule in DOTP 23.04.2008 Bulletin 2008/17 preparation" XP002413815 retrieved from STN Databaseaccession no. 1995: 468078& "Studyon (73) Proprietor: EASTMAN CHEMICAL COMPANY esterification rule in DOTP preparation" Kingsport TN 37660 (US) NANJING HUAGONG XUEYUAN XUEBAO , 1 CODEN: NAXUEI; ISSN: 1000-5994, vol. 16, no. 4, (72) Inventors: 1994, pages 69-72, • COOK, Steven, Leroy • DATABASECA [Online] CHEMICAL ABSTRACTS Kingsport, TN 37660 (US) SERVICE, COLUMBUS, OHIO, US; JIANG, • TOMLIN, Christopher, Fletcher PINPING: "Synthesis of DOTP plasticizer by Kingsport, TN 37660-5630 (US) esterification" XP002413816 retrieved from STN • TURNER, Philip, Wayne Database accession no. 1995:454573 & Blountville, TN 37617 (US) "Synthesis of DOTP plasticizer by esterification" HUAXUE SHIJIE , CODEN: HUAKAB; ISSN: (74) Representative: Brown, Fraser Gregory James et 0367-6358, vol. 35, no. 8, 1994, pages 411-415, al • DATABASE WPI Week 200003 Derwent Cleveland Publications Ltd., London, GB; AN 2000-036530 10 Fetter Lane XP002413844 & RU 2 114 100 C1 (KHIMPLAST London EC4A 1BR (GB) STOCK CO) 27 June 1998 (1998-06-27) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 912 929 B1 Printed by Jouve, 75001 PARIS (FR) 1 EP 1 912 929 B1 2 Description DETAILED DESCRIPTION FIELD OF THE INVENTION [0004] The esterification process of the present inven- tion is carried out in a reaction zone comprising a pres- [0001] This invention pertains to the preparation of 5 sure vessel while maintaining the EH:TPA mole ratio at di-(2-ethylhexyl) terephthalate from terephthalic acid 2:1 to 2.5:1 The pressure and temperature within the re- (TPA). More specifically, this invention pertains to a proc- action zone are maintained at 100 to 400 kPa gauge (1 ess for the preparation of di-(2-ethylhexyl) terephthalate to 4 bar gauge (barg)) and 180 to 270°C. Preferred pres- by the esterification of TPA with 2-ethylhexanol (EH) at sure and temperature ranges are 200 to 350 kPa gauge elevated temperature and pressure while removing the 10 (2 to 3.5 barg) and 180 to 260°C. water of reaction from the reaction mixture. [0005] An important feature of the present invention is the removal of water of reaction along with EH during the BACKGROUND OF THE INVENTION esterification process. The maintenance of the EH:TPA mole ratio at 2:1 to 2.5:1 requires the addition of EH to [0002] Di-(2-ethylhexyl) terephthalate, also known as 15 the reaction vessel during the process. The EH/water dioctyl terephthalate or DOTP, is used as a plasticizer in mixture or azeotrope removed from the reaction zone a variety of polymeric materials such as polyvinyl chlo- may beallowed toseparate into an EH- richorganic phase ride. DOTP can be prepared by the titanate-catalyzed and an aqueous phase and the EH-rich organic phase transesterification of dimethyl terephthalate (DMT) with can be returned to the reaction zone. Alternatively, the EH. Direct esterifications of TPA with EH under condi- 20 EH:TPA mole ratio may be maintained at 2:1 to 2.5: by tions similar to those used for the transesterification of the addition of fresh EH. DMT have produced slow reaction rates and sporadic [0006] The removal of water of reaction from the reac- problems with foaming. US-2002028963-A1 discloses tion zone is assisted by passing an inert gas through the an esterification process wherein water is removed by TPA/EH reaction mixture in the reaction zone. Nitrogen azeotropic distillation together with an alcohol. JP-25 is the least expensive and thus is the preferred inert gas. 60004151-A (JP-03004052-B) discloses the reaction of The inert gas typically is fed below the surface of the TPA and EH under elevated pressures and tempera- TPA/EH reaction mixture by means of a conventional tures. JP-2001031794-A discloses the preparation of conduit or via a gas sparging device. While the inert gas terephthalic acid esters by reacting at least one of C9- C may be fed intermittently or discontinuously, it preferably 18 monohydric alcohol and 2-ethylhexanol with tereph- 30 is fed continuously at the commencement of the esteri- thalic acid. Water formed during the reaction was re- fication reaction. The amount of gas passed through the moved and the alcohol was separated and recirculated TPA/EH reaction mixture may vary significantly but typ- to the system. Finally, US-5,532,495 discloses a multi- ically is in the range of 2 to 5 volumes of gas per volume step esterification process that includes removing water of reaction mixture per hour. and a portion of the alcohol reactant from the reaction 35 [0007] The titanium catalyst may be any titanium com- mixture. pound soluble in the reaction mixture, i.e., soluble in EH and the di-(2-ethylhexyl) terephthalate product. An ex- BRIEF SUMMARY OF THE INVENTION ample of suitable titanium compounds include titanium tetraalkoxides having the formula Ti(OR)4 wherein R is [0003] We have developed a process for the prepara- 40 an alkyl group of 1 to 8 carbon atoms. The catalytically- tion of di-(2- ethylhexyl) terephthalate by the esterification effective amount of the titanium compound generally is of TPA with EH at elevated pressure and temperature an amount which provides a titanium [Ti] concentration wherein the water of reaction and some of the EH is re- of 50 to 200 parts per million by weight in the reaction moved during the esterification process. The present mixture. The process of the present invention may be invention therefore provides a process 45 carried out in a batch, semi-continuous or continuous for the preparation of di-(2-ethylhexyl) terephthalate mode. In the batch mode, an agitated pressure vessel is which comprises contacting TPA with EH in the presence charged with TPA, EH and catalyst, heated and pressu- of a titanium catalyst in a reaction zone wherein the total rized and the esterification is carried out while passing pressure is maintained at 100 to 400 kPa gauge (1 to 4 an inert gas through the reaction mixture. An EH/water bar gauge), the temperature is maintained at 180° to50 mixture is removed and EH is fed to the reaction vessel 270°C, the EH: TPA mole ratio is maintained at 2: 1 to 2.5: over the course of the process. At the conclusion of the 1, and an inert gas is passed through the TPA/EH reac- process, the di-(2- ethylhexyl) terephthalate product is re- tion mixture in the reaction zone to cause a mixture of covered from the vessel and purified according to con- water and EH to be removed from the reaction zone dur- ventional procedures. Continuous operation involves ing the preparation of di-(2- ethylhexyl) terephthalate. Our 55 continuously or intermittently feeding TPA, EH and cat- novel process provides the desired diester product at alyst to and continuously or intermittently removing EH, good reaction rates with high conversions of the TPA water and product-containing reaction mixture from a reactant with no observable foaming problems. pressure vessel maintained at a predetermined temper- 2 3 EP 1 912 929 B1 4 ature, pressure and liquid level. The product-containing with the recycled EH to facilitate removal of water. Total reaction mixture may be fed to one or more secondary reaction time was 10.5 hours at a maximum temperature reaction vessels wherein conversion of TPA and/or TPA of 260°C and a maximum autoclave pressure of approx- half-ester to the diester product is completed. imately 300 kPa gauge (3 barg). Unreacted TPA (14 g) [0008] In the simplest embodiment, the reaction vessel 5 was recovered by filtration. The crude product then was may be fitted with one inlet for EH reactant return and a neutralized with 2.5% aqueous NaOH, washed with wa- control valve to remove volatiles in lieu of a fractionation ter and filtered. Excess EH was stripped off at reduced column. The reactor is charged with terephthalic acid, pressure and the residue then steam stripped. The excess 2-ethylhexanol, and a catalytic amount of a tita- stripped product was treated with activated carbon at nium catalyst such as titanium tetraisopropoxide (TIPT). 10 90°C for one hour then filtered through a filter aid to give Heating and stirring of the mixture results in both an in- 136.6 g of product ∼(80% conversion).
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