CA1120056A - Procede de production d'acide carboxylique aromatique isomerise et d'acide terephtalique - Google Patents

Procede de production d'acide carboxylique aromatique isomerise et d'acide terephtalique

Info

Publication number: CA1120056A
Authority: CA; Canada
Prior art keywords: reagent; carboxylic acid; aromatic carboxylic; isomerized; aromatic
Prior art date: 1978-03-06
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.): Expired

Application number

CA000322877A

Other languages

English (en)

Inventor

Geoffrey E. Dolbear

Raymond A. Schep

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.)

Occidental Research Corp

Original Assignee

Occidental Research Corp

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.)

1978-03-06

Filing date

1979-03-05

Publication date

1982-03-16

1979-03-05 Application filed by Occidental Research Corp filed Critical Occidental Research Corp

1982-03-16 Application granted granted Critical

1982-03-16 Publication of CA1120056A publication Critical patent/CA1120056A/fr

Status Expired legal-status Critical Current

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 181
238000000034 method Methods 0.000 title claims abstract description 117
230000008569 process Effects 0.000 title claims abstract description 115
125000003118 aryl group Chemical group 0.000 title claims abstract description 103
150000001735 carboxylic acids Chemical class 0.000 title abstract description 12
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 270
239000003153 chemical reaction reagent Substances 0.000 claims abstract description 189
239000000203 mixture Substances 0.000 claims abstract description 114
239000002253 acid Substances 0.000 claims abstract description 109
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 98
239000000463 material Substances 0.000 claims abstract description 87
229910052751 metal Inorganic materials 0.000 claims abstract description 55
239000002184 metal Substances 0.000 claims abstract description 55
235000010233 benzoic acid Nutrition 0.000 claims abstract description 50
239000005711 Benzoic acid Substances 0.000 claims abstract description 46
239000001301 oxygen Substances 0.000 claims abstract description 45
229910052760 oxygen Inorganic materials 0.000 claims abstract description 45
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 43
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 17
230000007062 hydrolysis Effects 0.000 claims abstract description 16
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 16
239000012670 alkaline solution Substances 0.000 claims abstract description 14
238000010438 heat treatment Methods 0.000 claims abstract description 14
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims abstract description 13
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 13
229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 12
235000011181 potassium carbonates Nutrition 0.000 claims abstract description 12
235000015497 potassium bicarbonate Nutrition 0.000 claims abstract description 10
239000011736 potassium bicarbonate Substances 0.000 claims abstract description 10
229910000028 potassium bicarbonate Inorganic materials 0.000 claims abstract description 10
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims abstract description 10
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical group [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 120
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 98
235000011056 potassium acetate Nutrition 0.000 claims description 60
239000003245 coal Substances 0.000 claims description 54
238000007254 oxidation reaction Methods 0.000 claims description 50
239000001569 carbon dioxide Substances 0.000 claims description 49
229910002092 carbon dioxide Inorganic materials 0.000 claims description 49
230000003647 oxidation Effects 0.000 claims description 46
150000003839 salts Chemical class 0.000 claims description 46
238000006317 isomerization reaction Methods 0.000 claims description 39
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 32
239000003054 catalyst Substances 0.000 claims description 31
229910052700 potassium Inorganic materials 0.000 claims description 29
239000011591 potassium Substances 0.000 claims description 29
239000007789 gas Substances 0.000 claims description 27
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 claims description 25
238000004064 recycling Methods 0.000 claims description 21
238000002156 mixing Methods 0.000 claims description 19
238000011282 treatment Methods 0.000 claims description 19
OKIIEJOIXGHUKX-UHFFFAOYSA-L cadmium iodide Chemical group [Cd+2].[I-].[I-] OKIIEJOIXGHUKX-UHFFFAOYSA-L 0.000 claims description 16
230000001590 oxidative effect Effects 0.000 claims description 14
239000002802 bituminous coal Substances 0.000 claims description 12
239000003575 carbonaceous material Substances 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 11
229940075417 cadmium iodide Drugs 0.000 claims description 8
239000003518 caustics Substances 0.000 claims description 7
239000007864 aqueous solution Substances 0.000 claims description 6
230000006872 improvement Effects 0.000 claims description 5
JOGSGUQZPZCJCG-UHFFFAOYSA-L cadmium(2+);dibenzoate Chemical group [Cd+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JOGSGUQZPZCJCG-UHFFFAOYSA-L 0.000 claims description 3
230000001376 precipitating effect Effects 0.000 claims 4
230000003301 hydrolyzing effect Effects 0.000 claims 1
230000001172 regenerating effect Effects 0.000 claims 1
239000002244 precipitate Substances 0.000 abstract description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 164
229960000583 acetic acid Drugs 0.000 description 54
239000000243 solution Substances 0.000 description 45
-1 aromatic carboxylic acids Chemical class 0.000 description 35
239000007787 solid Substances 0.000 description 35
229960004365 benzoic acid Drugs 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 29
229960003975 potassium Drugs 0.000 description 27
235000007686 potassium Nutrition 0.000 description 27
150000007513 acids Chemical class 0.000 description 26
239000000047 product Substances 0.000 description 23
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
239000007788 liquid Substances 0.000 description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000012716 precipitator Substances 0.000 description 18
238000002474 experimental method Methods 0.000 description 14
238000004519 manufacturing process Methods 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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
239000003513 alkali Substances 0.000 description 11
QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
238000000926 separation method Methods 0.000 description 9
238000001914 filtration Methods 0.000 description 8
230000020477 pH reduction Effects 0.000 description 8
239000004300 potassium benzoate Substances 0.000 description 8
235000010235 potassium benzoate Nutrition 0.000 description 8
229940103091 potassium benzoate Drugs 0.000 description 8
CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 8
239000007858 starting material Substances 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 7
238000001556 precipitation Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
159000000032 aromatic acids Chemical class 0.000 description 6
230000008901 benefit Effects 0.000 description 6
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 6
238000007323 disproportionation reaction Methods 0.000 description 6
235000011121 sodium hydroxide Nutrition 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
229910052793 cadmium Inorganic materials 0.000 description 5
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 5
150000001734 carboxylic acid salts Chemical class 0.000 description 5
239000011280 coal tar Substances 0.000 description 5
238000001035 drying Methods 0.000 description 5
238000000605 extraction Methods 0.000 description 5
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
230000008929 regeneration Effects 0.000 description 5
238000011069 regeneration method Methods 0.000 description 5
239000011343 solid material Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
150000001491 aromatic compounds Chemical class 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
238000010981 drying operation Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
239000012535 impurity Substances 0.000 description 4
239000002609 medium Substances 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
BPWIVQHIJYRBSR-UHFFFAOYSA-M potassium;hydron;terephthalate Chemical compound [K+].OC(=O)C1=CC=C(C([O-])=O)C=C1 BPWIVQHIJYRBSR-UHFFFAOYSA-M 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
235000008733 Citrus aurantifolia Nutrition 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
235000011941 Tilia x europaea Nutrition 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
RHZUVFJBSILHOK-UHFFFAOYSA-N anthracen-1-ylmethanolate Chemical compound C1=CC=C2C=C3C(C[O-])=CC=CC3=CC2=C1 RHZUVFJBSILHOK-UHFFFAOYSA-N 0.000 description 3
239000003830 anthracite Substances 0.000 description 3
239000001175 calcium sulphate Substances 0.000 description 3
235000011132 calcium sulphate Nutrition 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000010924 continuous production Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
229940093915 gynecological organic acid Drugs 0.000 description 3
229910001385 heavy metal Inorganic materials 0.000 description 3
239000003077 lignite Substances 0.000 description 3
239000004571 lime Substances 0.000 description 3
238000006396 nitration reaction Methods 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
239000003415 peat Substances 0.000 description 3
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 3
159000000001 potassium salts Chemical class 0.000 description 3
230000001737 promoting effect Effects 0.000 description 3
239000011833 salt mixture Substances 0.000 description 3
238000000638 solvent extraction Methods 0.000 description 3
241000894007 species Species 0.000 description 3
230000019635 sulfation Effects 0.000 description 3
238000005670 sulfation reaction Methods 0.000 description 3
239000011269 tar Substances 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
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
150000001601 aromatic carbocyclic compounds Chemical class 0.000 description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
238000010923 batch production Methods 0.000 description 2
UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
239000000571 coke Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
238000010586 diagram Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-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
239000000284 extract Substances 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
239000012263 liquid product Substances 0.000 description 2
XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 2
YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
239000004058 oil shale Substances 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
239000011295 pitch Substances 0.000 description 2
WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 2
235000011118 potassium hydroxide Nutrition 0.000 description 2
229910052939 potassium sulfate Inorganic materials 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000011084 recovery Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
ZUXNHFFVQWADJL-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(2-methoxyethyl)-n-(4-phenyl-1,3-thiazol-2-yl)benzamide Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1N(CCOC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 ZUXNHFFVQWADJL-UHFFFAOYSA-N 0.000 description 1
XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 1
KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000011398 Portland cement Substances 0.000 description 1
239000004153 Potassium bromate Substances 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
241000982035 Sparattosyce Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000004983 alkyl aryl ketones Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
229940112016 barium acetate Drugs 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
YUOUKRIPFJKDJY-UHFFFAOYSA-L beryllium;diacetate Chemical compound [Be+2].CC([O-])=O.CC([O-])=O YUOUKRIPFJKDJY-UHFFFAOYSA-L 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
CXKCTMHTOKXKQT-UHFFFAOYSA-N cadmium oxide Inorganic materials [Cd]=O CXKCTMHTOKXKQT-UHFFFAOYSA-N 0.000 description 1
CFEAAQFZALKQPA-UHFFFAOYSA-N cadmium(2+);oxygen(2-) Chemical compound [O-2].[Cd+2] CFEAAQFZALKQPA-UHFFFAOYSA-N 0.000 description 1
ZOAIGCHJWKDIPJ-UHFFFAOYSA-M caesium acetate Chemical compound [Cs+].CC([O-])=O ZOAIGCHJWKDIPJ-UHFFFAOYSA-M 0.000 description 1
VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
235000011092 calcium acetate Nutrition 0.000 description 1
239000001639 calcium acetate Substances 0.000 description 1
229960005147 calcium acetate Drugs 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
235000012255 calcium oxide Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000003763 carbonization Methods 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
GIGWNNOCCCHECH-UHFFFAOYSA-L dipotassium;benzene-1,3-dicarboxylate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=CC(C([O-])=O)=C1 GIGWNNOCCCHECH-UHFFFAOYSA-L 0.000 description 1
239000011363 dried mixture Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000622 liquid--liquid extraction Methods 0.000 description 1
XKPJKVVZOOEMPK-UHFFFAOYSA-M lithium;formate Chemical compound [Li+].[O-]C=O XKPJKVVZOOEMPK-UHFFFAOYSA-M 0.000 description 1
AXMOZGKEVIBBCF-UHFFFAOYSA-M lithium;propanoate Chemical compound [Li+].CCC([O-])=O AXMOZGKEVIBBCF-UHFFFAOYSA-M 0.000 description 1
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
235000011285 magnesium acetate Nutrition 0.000 description 1
239000011654 magnesium acetate Substances 0.000 description 1
229940069446 magnesium acetate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940071125 manganese acetate Drugs 0.000 description 1
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 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
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
235000019396 potassium bromate Nutrition 0.000 description 1
229940094037 potassium bromate Drugs 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
BWILYWWHXDGKQA-UHFFFAOYSA-M potassium propanoate Chemical compound [K+].CCC([O-])=O BWILYWWHXDGKQA-UHFFFAOYSA-M 0.000 description 1
239000004331 potassium propionate Substances 0.000 description 1
235000010332 potassium propionate Nutrition 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
UNTOVVPYDPRUQE-UHFFFAOYSA-M potassium;propanoate;propanoic acid Chemical compound [K+].CCC(O)=O.CCC([O-])=O UNTOVVPYDPRUQE-UHFFFAOYSA-M 0.000 description 1
238000011085 pressure filtration Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
FOGKDYADEBOSPL-UHFFFAOYSA-M rubidium(1+);acetate Chemical compound [Rb+].CC([O-])=O FOGKDYADEBOSPL-UHFFFAOYSA-M 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000003079 shale oil Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
239000004324 sodium propionate Substances 0.000 description 1
235000010334 sodium propionate Nutrition 0.000 description 1
229960003212 sodium propionate Drugs 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003503 terephthalic acid derivatives Chemical class 0.000 description 1
238000007669 thermal treatment Methods 0.000 description 1
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
HPLPROFFQFFUCO-UHFFFAOYSA-K tripotassium benzene-1,3,5-tricarboxylate Chemical compound [K+].[K+].[K+].[O-]C(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1 HPLPROFFQFFUCO-UHFFFAOYSA-K 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
238000013022 venting Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

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

CA000322877A 1978-03-06 1979-03-05 Procede de production d'acide carboxylique aromatique isomerise et d'acide terephtalique Expired CA1120056A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US88399578A	1978-03-06	1978-03-06
US883,995		1992-05-18

Publications (1)

Publication Number	Publication Date
CA1120056A true CA1120056A (fr)	1982-03-16

Family

ID=25383753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000322877A Expired CA1120056A (fr)	1978-03-06	1979-03-05	Procede de production d'acide carboxylique aromatique isomerise et d'acide terephtalique

Country Status (1)

Country	Link
CA (1)	CA1120056A (fr)

1979
- 1979-03-05 CA CA000322877A patent/CA1120056A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-03-16	MKEX	Expiry

Publication	Publication Date	Title
US3673154A (en)	1972-06-27	Process for the recovery of cobalt catalyst
US3064044A (en)	1962-11-13	Multistage oxidation system for preparing dicarboxylic acid
US3887612A (en)	1975-06-03	Process for preparing high purity terephthalic acid
DE69924523T2 (de)	2006-02-09	Verfahren zur herstellung aromatischer carbonsäuren
KR100282074B1 (ko)	2001-02-15	2,6-나프탈렌디카복실산의제조방법
CA1296742C (fr)	1992-03-03	Methode de preparation d'acides terephtaliques de grande purete
US4356319A (en)	1982-10-26	Method of recovering in active form the catalyst for the terephthalic acid synthesis
CA2284721C (fr)	2007-06-12	Procede de preparation d'acide 2,6-naphtalenedicarboxylique
US3873468A (en)	1975-03-25	Method of removing substance harmful to oxidation reaction in the production of benzenecarboxylic acids by oxidation
US7470370B2 (en)	2008-12-30	Process for removal of impurities from mother liquor in the synthesis of carboxylic acid using pressure filtration
GB2032920A (en)	1980-05-14	Process for preparing terephthalic acid
US4345098A (en)	1982-08-17	Process for producing benzene carboxylic acid salts and their acids
US3873609A (en)	1975-03-25	Continuous slurry process for formation of aromatic polycarboxylic acids
CA1120055A (fr)	1982-03-16	Procede de production de l'acide carboxylique et de l'acide carboxylique aromatique
US4625056A (en)	1986-11-25	Process for producing benzene carboxylic acids from aromatic material utilizing an aliphatic organic acid agent
US3919306A (en)	1975-11-11	Purification of recirculated stream for isophthalic acid production
US4375553A (en)	1983-03-01	Process for producing benzene carboxylic acid salts from aromatic materials
US2930813A (en)	1960-03-29	Process for the preparation of cyclic dicarboxylic acids
US4876386A (en)	1989-10-24	Process for the oxidation of di- or trimethylbenzenes in the presence of cobalt and manganese from oxidation residue incinerator ash
US4294977A (en)	1981-10-13	Process for producing aromatic carboxylic acids
US4786621A (en)	1988-11-22	Process for recovery of cobalt and manganese for oxidation residue incinerator ash
US3064046A (en)	1962-11-13	Oxidation of organic compounds
US3787487A (en)	1974-01-22	Preparation of metal salt slurries from metal salt solutions
CA1085879A (fr)	1980-09-16	Separation continue des hydro-carbures qui ne contiennent pas de paraffine de ceux qui en contiennent
JPS61106535A (ja)	1986-05-24	安息香酸の回収法