PL97498B1 - Sposob wytwarzania kwasu tereftalowego w fazie polplynnej - Google Patents
Sposob wytwarzania kwasu tereftalowego w fazie polplynnej Download PDFInfo
- Publication number
- PL97498B1 PL97498B1 PL1974167949A PL16794974A PL97498B1 PL 97498 B1 PL97498 B1 PL 97498B1 PL 1974167949 A PL1974167949 A PL 1974167949A PL 16794974 A PL16794974 A PL 16794974A PL 97498 B1 PL97498 B1 PL 97498B1
- Authority
- PL
- Poland
- Prior art keywords
- dispersant
- catalyst
- disproportionation
- alkali metal
- pulp
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 54
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000002253 acid Substances 0.000 title description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 66
- 239000003054 catalyst Substances 0.000 claims description 61
- 239000002270 dispersing agent Substances 0.000 claims description 41
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 40
- 238000007323 disproportionation reaction Methods 0.000 claims description 39
- -1 alkali metal salt Chemical class 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- 239000005711 Benzoic acid Substances 0.000 claims description 28
- 229910052783 alkali metal Inorganic materials 0.000 claims description 28
- 235000010233 benzoic acid Nutrition 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000012071 phase Substances 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 14
- 238000011084 recovery Methods 0.000 claims description 12
- 239000008346 aqueous phase Substances 0.000 claims description 6
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 6
- 239000002609 medium Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 3
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005580 triphenylene group Chemical group 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002612 dispersion medium Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 239000007809 chemical reaction catalyst Substances 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- QMZIDZZDMPWRHM-UHFFFAOYSA-L manganese(2+);dibenzoate Chemical compound [Mn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 QMZIDZZDMPWRHM-UHFFFAOYSA-L 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 18
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000004300 potassium benzoate Substances 0.000 description 11
- 229940103091 potassium benzoate Drugs 0.000 description 11
- 235000010235 potassium benzoate Nutrition 0.000 description 11
- 230000008929 regeneration Effects 0.000 description 11
- 238000011069 regeneration method Methods 0.000 description 11
- 229940050390 benzoate Drugs 0.000 description 8
- 229910044991 metal oxide Inorganic materials 0.000 description 8
- 150000004706 metal oxides Chemical class 0.000 description 8
- 239000011787 zinc oxide Substances 0.000 description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 239000001569 carbon dioxide Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- 239000007790 solid phase Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- LRUDDHYVRFQYCN-UHFFFAOYSA-L dipotassium;terephthalate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 LRUDDHYVRFQYCN-UHFFFAOYSA-L 0.000 description 5
- 238000005649 metathesis reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical class OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- GOMCKELMLXHYHH-UHFFFAOYSA-L dipotassium;phthalate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=CC=C1C([O-])=O GOMCKELMLXHYHH-UHFFFAOYSA-L 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 2
- CHBDXRNMDNRJJC-UHFFFAOYSA-N 1,2,3-triphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CHBDXRNMDNRJJC-UHFFFAOYSA-N 0.000 description 1
- 229920003026 Acene Polymers 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 239000004135 Bone phosphate Substances 0.000 description 1
- WVNQDVFFWZGNQI-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)O.C1(=CC=CC=C1)C=1C(=C(C=CC1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical group C(C1=CC=CC=C1)(=O)O.C1(=CC=CC=C1)C=1C(=C(C=CC1)C1=CC=CC=C1)C1=CC=CC=C1 WVNQDVFFWZGNQI-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- MVWDJLOUEUAWIE-UHFFFAOYSA-N O=C=O.O=C=O Chemical compound O=C=O.O=C=O MVWDJLOUEUAWIE-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000278713 Theora Species 0.000 description 1
- RWYUNGQDYAQZRY-UHFFFAOYSA-N [O-2].[Zn+2].C(C1=CC=CC=C1)(=O)O Chemical compound [O-2].[Zn+2].C(C1=CC=CC=C1)(=O)O RWYUNGQDYAQZRY-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical group O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
- KCNMSAKCTPBRPK-UHFFFAOYSA-N benzoic acid;terephthalic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=C(C(O)=O)C=C1 KCNMSAKCTPBRPK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- OXMLCJOPQGRRKV-UHFFFAOYSA-K chromium(3+);tribenzoate Chemical compound [Cr+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 OXMLCJOPQGRRKV-UHFFFAOYSA-K 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- QWJNFFYFEKXZBF-UHFFFAOYSA-N cyanocyanamide Chemical compound N#CNC#N QWJNFFYFEKXZBF-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/416—Henkel reaction and related reactions, i.e. rearrangement of carboxylate salt groups linked to six-membered aromatic rings, in the absence or in the presence of CO or CO2, (e.g. preparation of terepholates from benzoates); no additional classification for the subsequent hydrolysis of the salt groups has to be given
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US321523A US3873609A (en) | 1973-01-05 | 1973-01-05 | Continuous slurry process for formation of aromatic polycarboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL97498B1 true PL97498B1 (pl) | 1978-02-28 |
Family
ID=23250953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1974167949A PL97498B1 (pl) | 1973-01-05 | 1974-01-06 | Sposob wytwarzania kwasu tereftalowego w fazie polplynnej |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US3873609A (en]) |
| JP (1) | JPS5247451B2 (en]) |
| AR (1) | AR197059A1 (en]) |
| AT (1) | AT331230B (en]) |
| AU (1) | AU5924673A (en]) |
| BE (1) | BE807267A (en]) |
| BG (1) | BG28843A3 (en]) |
| BR (1) | BR7307007D0 (en]) |
| CA (1) | CA999877A (en]) |
| CH (1) | CH584179A5 (en]) |
| CS (1) | CS190398B2 (en]) |
| DD (1) | DD109374A5 (en]) |
| DE (1) | DE2400012B2 (en]) |
| ES (1) | ES421979A1 (en]) |
| FR (1) | FR2213266B1 (en]) |
| GB (1) | GB1436671A (en]) |
| HU (1) | HU168286B (en]) |
| IN (1) | IN139337B (en]) |
| IT (1) | IT1002419B (en]) |
| LU (1) | LU68911A1 (en]) |
| NL (1) | NL171443C (en]) |
| PL (1) | PL97498B1 (en]) |
| RO (1) | RO63027A (en]) |
| SE (1) | SE406760B (en]) |
| ZA (1) | ZA735608B (en]) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2373509A1 (fr) * | 1976-12-09 | 1978-07-07 | Rhone Poulenc Ind | Procede de rearrangement en continu de sel alcalin d'acide carboxylique aromatique sous pression d'anhydride carbonique |
| US4435596A (en) | 1978-04-06 | 1984-03-06 | Phillips Petroleum Company | Process of producing terephthalic acid |
| US4356105A (en) * | 1978-04-06 | 1982-10-26 | Phillips Petroleum Company | Low viscosity slurry and method of preparing same |
| US4430511A (en) | 1978-04-06 | 1984-02-07 | Phillips Petroleum Company | Method for producing terephthalic acid |
| US4357257A (en) * | 1978-04-06 | 1982-11-02 | Phillips Petroleum Company | Low viscosity slurry and method of preparing same |
| US4263451A (en) * | 1979-10-15 | 1981-04-21 | Phillips Petroleum Company | Removing carbonaceous contaminant from zinc oxide |
| JP2545103B2 (ja) * | 1987-12-17 | 1996-10-16 | 三井石油化学工業株式会社 | テレフタル酸スラリ―の分散媒交換方法 |
| FR2672049A1 (fr) * | 1991-01-30 | 1992-07-31 | Benzaria Jacques | Procede de fabrication de terephtalate de metal alcalin ou alcalino-terreux ou de l'acide terephilique de purete elevee. |
| US5580905A (en) * | 1994-04-28 | 1996-12-03 | United Resource Recovery Corporation | Process for recycling polyesters |
| US5958987A (en) | 1996-04-10 | 1999-09-28 | The Coca-Cola Company | Process for separating polyester from other materials |
| ATE497517T1 (de) * | 2001-06-19 | 2011-02-15 | United Resource Recovery Corp | Verfahren zur trennung von polyester von anderen materialien |
| US7098299B1 (en) | 2005-03-16 | 2006-08-29 | United Resource Recovery Corporation | Separation of contaminants from polyester materials |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL206812A (en]) * | 1955-05-04 | |||
| DE1144254B (de) * | 1961-07-08 | 1963-02-28 | Basf Ag | Verfahren zur Herstellung von Alkalisalzen cyclischer Carbonsaeuren aromatischer Natur durch Erhitzen von Alkalisalzen anderer cyclischer Carbonsaeuren |
| BE788647A (fr) * | 1971-06-25 | 1973-03-12 | Phillips Petroleum Co | Procede de production de sels metalliques d'acides carboxyliques aromatiques et de disproportionnement de ces sels et nouveaux produits ainsi obtenus |
| BE788491A (fr) * | 1971-06-25 | 1973-03-07 | Phillips Petroleum Co | Procede de preparation de boues des sels metalliques a partir de solutions de sels metalliques d'acides carboxyliques et nouveaux produits ainsi obtenus |
| US3781341A (en) * | 1971-06-25 | 1973-12-25 | Phillips Petroleum Co | Disproportionation of alkali metal salts of aromatic carboxylic acids |
-
1973
- 1973-01-05 US US321523A patent/US3873609A/en not_active Expired - Lifetime
- 1973-07-16 CA CA176,564A patent/CA999877A/en not_active Expired
- 1973-08-15 AU AU59246/73A patent/AU5924673A/en not_active Expired
- 1973-08-16 ZA ZA735608A patent/ZA735608B/xx unknown
- 1973-08-17 IN IN1905/CAL/73A patent/IN139337B/en unknown
- 1973-09-07 AR AR249971A patent/AR197059A1/es active
- 1973-09-11 BR BR7007/73A patent/BR7307007D0/pt unknown
- 1973-09-12 JP JP48102993A patent/JPS5247451B2/ja not_active Expired
- 1973-11-13 BE BE137704A patent/BE807267A/xx unknown
- 1973-12-03 LU LU68911A patent/LU68911A1/xx unknown
- 1973-12-28 IT IT32385/73A patent/IT1002419B/it active
-
1974
- 1974-01-02 DE DE19742400012 patent/DE2400012B2/de active Granted
- 1974-01-03 ES ES421979A patent/ES421979A1/es not_active Expired
- 1974-01-04 FR FR7400292A patent/FR2213266B1/fr not_active Expired
- 1974-01-04 CH CH6874A patent/CH584179A5/xx not_active IP Right Cessation
- 1974-01-04 SE SE7400079A patent/SE406760B/xx unknown
- 1974-01-04 DD DD175833A patent/DD109374A5/xx unknown
- 1974-01-04 GB GB38674A patent/GB1436671A/en not_active Expired
- 1974-01-04 HU HUPI402A patent/HU168286B/hu unknown
- 1974-01-04 NL NLAANVRAGE7400117,A patent/NL171443C/xx active
- 1974-01-04 AT AT4674*#A patent/AT331230B/de not_active IP Right Cessation
- 1974-01-05 BG BG025438A patent/BG28843A3/xx unknown
- 1974-01-05 RO RO7400077200A patent/RO63027A/ro unknown
- 1974-01-06 PL PL1974167949A patent/PL97498B1/pl unknown
- 1974-01-07 CS CS7485A patent/CS190398B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2400012C3 (en]) | 1978-03-30 |
| HU168286B (en]) | 1976-03-28 |
| DE2400012A1 (de) | 1974-07-25 |
| JPS5247451B2 (en]) | 1977-12-02 |
| AU5924673A (en) | 1974-07-04 |
| DD109374A5 (en]) | 1974-11-05 |
| SE406760B (sv) | 1979-02-26 |
| JPS4995933A (en]) | 1974-09-11 |
| NL7400117A (en]) | 1974-07-09 |
| ATA4674A (de) | 1975-11-15 |
| BG28843A3 (en) | 1980-07-15 |
| AR197059A1 (es) | 1974-03-08 |
| BR7307007D0 (pt) | 1974-10-29 |
| ES421979A1 (es) | 1976-05-01 |
| LU68911A1 (en]) | 1974-02-11 |
| CH584179A5 (en]) | 1977-01-31 |
| NL171443C (nl) | 1983-04-05 |
| IN139337B (en]) | 1976-06-05 |
| CA999877A (en) | 1976-11-16 |
| BE807267A (fr) | 1974-03-01 |
| CS190398B2 (en) | 1979-05-31 |
| FR2213266A1 (en]) | 1974-08-02 |
| FR2213266B1 (en]) | 1976-11-26 |
| US3873609A (en) | 1975-03-25 |
| ZA735608B (en) | 1974-07-31 |
| GB1436671A (en) | 1976-05-19 |
| AT331230B (de) | 1976-08-10 |
| IT1002419B (it) | 1976-05-20 |
| DE2400012B2 (de) | 1977-06-23 |
| RO63027A (fr) | 1978-05-15 |
| AU450229B2 (en]) | 1974-07-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7470370B2 (en) | Process for removal of impurities from mother liquor in the synthesis of carboxylic acid using pressure filtration | |
| CA2059719C (en) | Process for the production of terephthalic acid | |
| PL97498B1 (pl) | Sposob wytwarzania kwasu tereftalowego w fazie polplynnej | |
| US2727926A (en) | Catalytic oxidation of armoatic carboxylic acids to phenols | |
| US3484458A (en) | Trimellitic acid production and recovery of intramolecular anhydride | |
| SU710514A3 (ru) | Способ получени терефталевой кислоты | |
| EP2450342B1 (en) | Process for production of a dried carboxylic acid cake suitable for use in polyester production | |
| US4345098A (en) | Process for producing benzene carboxylic acid salts and their acids | |
| GB2114564A (en) | A process for crystallizing trimellitic acid | |
| PL83682B1 (en]) | ||
| JPH0925271A (ja) | 無水・高圧メラミン合成法 | |
| CA1120055A (en) | Process for producing carboxylic acids and aromatic carboxylic acids | |
| US4695407A (en) | Method for purifying 1-aminoanthraquinone | |
| US3787487A (en) | Preparation of metal salt slurries from metal salt solutions | |
| EP1345846A1 (en) | Crystallisation process for producing highly concentrated hydrogen peroxide | |
| US3872135A (en) | Separation of anthraquinone from a mixture of its vapor with a carrier gas | |
| SU495821A3 (ru) | Способ получени поликарбоновых кислот | |
| US4962274A (en) | Process for separating alkyl-substituted naphthalene derivatives using clathrate complexes | |
| US4375553A (en) | Process for producing benzene carboxylic acid salts from aromatic materials | |
| US4294977A (en) | Process for producing aromatic carboxylic acids | |
| US3031500A (en) | Conversion of ammonium salts | |
| Downs | Oxidation of aromatic hydrocarbons | |
| US5153339A (en) | Process for separation of naphthoquinone and phthalic acid | |
| CA1120056A (en) | Process for producing isomerized aromatic carboxylic acids and terephthalic acid | |
| JPH0455182B2 (en]) |