ES2916712T3 - Método de obtención de ácido tereftálico a partir de residuos de tereftalato de polietileno - Google Patents

Método de obtención de ácido tereftálico a partir de residuos de tereftalato de polietileno Download PDF

Info

Publication number: ES2916712T3
Authority: ES; Spain
Prior art keywords: terephthalic acid; depolymerization; extraction; mixture; phase
Prior art date: 2018-03-12
Legal status (The legal status 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 status listed.): Active

Application number

ES19713676T

Other languages

English (en)

Spanish (es)

Inventor

Jaromir Sramek

Michal Trzewiczek

Karel Travnicek

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

JBPV sro

Original Assignee

JBPV sro

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.)

2018-03-12

Filing date

2019-03-11

Publication date

2022-07-05

2019-03-11 Application filed by JBPV sro filed Critical JBPV sro

2019-03-11 Priority claimed from PCT/CZ2019/000014 external-priority patent/WO2019174656A1/en

2022-07-05 Application granted granted Critical

2022-07-05 Publication of ES2916712T3 publication Critical patent/ES2916712T3/es

Status Active legal-status Critical Current

2039-03-11 Anticipated expiration legal-status Critical

Links

KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims abstract description 107
238000000034 method Methods 0.000 title claims abstract description 43
-1 polyethylene terephthalate residues Polymers 0.000 title claims abstract description 30
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 41
239000012071 phase Substances 0.000 claims abstract description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
239000000203 mixture Substances 0.000 claims abstract description 28
239000011541 reaction mixture Substances 0.000 claims abstract description 17
239000002594 sorbent Substances 0.000 claims abstract description 17
239000008346 aqueous phase Substances 0.000 claims abstract description 9
239000012535 impurity Substances 0.000 claims abstract description 9
238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract description 7
238000000746 purification Methods 0.000 claims abstract description 7
239000000725 suspension Substances 0.000 claims abstract description 7
238000000926 separation method Methods 0.000 claims abstract description 6
238000012691 depolymerization reaction Methods 0.000 claims abstract description 5
239000002244 precipitate Substances 0.000 claims abstract description 5
239000007795 chemical reaction product Substances 0.000 claims abstract description 4
238000010438 heat treatment Methods 0.000 claims abstract description 4
239000007790 solid phase Substances 0.000 claims abstract description 4
239000003960 organic solvent Substances 0.000 claims abstract description 3
230000020477 pH reduction Effects 0.000 claims abstract description 3
239000007792 gaseous phase Substances 0.000 claims abstract 2
238000000605 extraction Methods 0.000 claims description 40
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
239000003795 chemical substances by application Substances 0.000 claims description 18
229910052799 carbon Inorganic materials 0.000 claims description 7
229920006395 saturated elastomer Chemical group 0.000 claims description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
150000001298 alcohols Chemical class 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
238000004061 bleaching Methods 0.000 claims description 4
239000004927 clay Substances 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 3
229920000139 polyethylene terephthalate Polymers 0.000 description 44
239000005020 polyethylene terephthalate Substances 0.000 description 44
239000000243 solution Substances 0.000 description 25
239000002699 waste material Substances 0.000 description 18
230000007062 hydrolysis Effects 0.000 description 14
238000006460 hydrolysis reaction Methods 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
230000005855 radiation Effects 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000013078 crystal Substances 0.000 description 8
238000004064 recycling Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000001556 precipitation Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000005809 transesterification reaction Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
239000000047 product Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
150000008044 alkali metal hydroxides Chemical class 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
VIQSRHWJEKERKR-UHFFFAOYSA-L disodium;terephthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 VIQSRHWJEKERKR-UHFFFAOYSA-L 0.000 description 4
230000034659 glycolysis Effects 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000012266 salt solution Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
239000012190 activator Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000006731 degradation reaction Methods 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
238000005191 phase separation Methods 0.000 description 3
238000012545 processing Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003797 solvolysis reaction Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
150000003503 terephthalic acid derivatives Chemical class 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000012993 chemical processing Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
FFPQSNUAVYJZDH-UHFFFAOYSA-N diazanium;terephthalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 FFPQSNUAVYJZDH-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001125 extrusion Methods 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
239000012451 post-reaction mixture Substances 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
239000010457 zeolite Substances 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241001550224 Apha Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
TXTQARDVRPFFHL-UHFFFAOYSA-N [Sb].[H][H] Chemical compound [Sb].[H][H] TXTQARDVRPFFHL-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000005915 ammonolysis reaction Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
235000013361 beverage Nutrition 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000011437 continuous method Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000005265 energy consumption Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
239000013502 plastic waste Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
UONOETXJSWQNOL-UHFFFAOYSA-N tungsten carbide Chemical compound [W+]#[C-] UONOETXJSWQNOL-UHFFFAOYSA-N 0.000 description 1
229920006337 unsaturated polyester resin Polymers 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910000859 α-Fe Inorganic materials 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyesters Or Polycarbonates (AREA)

ES19713676T 2018-03-12 2019-03-11 Método de obtención de ácido tereftálico a partir de residuos de tereftalato de polietileno Active ES2916712T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CZ201812000		2018-03-12
PCT/CZ2019/000014 WO2019174656A1 (en)	2018-03-12	2019-03-11	Method of obtaining terephthalic acid from waste polyethylene terephthalate

Publications (1)

Publication Number	Publication Date
ES2916712T3 true ES2916712T3 (es)	2022-07-05

Family

ID=82217711

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES19713676T Active ES2916712T3 (es)	2018-03-12	2019-03-11	Método de obtención de ácido tereftálico a partir de residuos de tereftalato de polietileno

Country Status (3)

Country	Link
ES (1)	ES2916712T3 (pl)
HU (1)	HUE058760T2 (pl)
PL (1)	PL3765559T3 (pl)

2019
- 2019-03-11 PL PL19713676.5T patent/PL3765559T3/pl unknown
- 2019-03-11 ES ES19713676T patent/ES2916712T3/es active Active
- 2019-03-11 HU HUE19713676A patent/HUE058760T2/hu unknown

Also Published As

Publication number	Publication date
HUE058760T2 (hu)	2022-09-28
PL3765559T3 (pl)	2022-10-03

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