CA1120055A - Procede de production de l'acide carboxylique et de l'acide carboxylique aromatique - Google Patents

Procede de production de l'acide carboxylique et de l'acide carboxylique aromatique

Info

Publication number: CA1120055A
Authority: CA; Canada
Prior art keywords: reagent; carboxylic acid; aromatic carboxylic; aromatic; isomerized
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

CA000322657A

Other languages

English (en)

Inventor

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

1979-03-02

Publication date

1982-03-16

1979-03-02 Application filed by Occidental Research Corp filed Critical Occidental Research Corp

1982-03-16 Application granted granted Critical

1982-03-16 Publication of CA1120055A publication Critical patent/CA1120055A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 119
125000003118 aryl group Chemical group 0.000 title claims abstract description 73
150000001735 carboxylic acids Chemical class 0.000 title abstract description 16
239000003153 chemical reaction reagent Substances 0.000 claims abstract description 184
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 157
239000000203 mixture Substances 0.000 claims abstract description 109
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 106
239000002253 acid Substances 0.000 claims abstract description 95
239000000463 material Substances 0.000 claims abstract description 62
229910052751 metal Inorganic materials 0.000 claims abstract description 54
239000002184 metal Substances 0.000 claims abstract description 54
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 44
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 30
238000004064 recycling Methods 0.000 claims abstract description 27
239000002244 precipitate Substances 0.000 claims abstract description 26
239000003575 carbonaceous material Substances 0.000 claims abstract description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 19
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 15
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 15
229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 15
235000011181 potassium carbonates Nutrition 0.000 claims abstract description 15
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims abstract description 14
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 13
238000010438 heat treatment Methods 0.000 claims abstract description 12
239000011736 potassium bicarbonate Substances 0.000 claims abstract description 11
235000015497 potassium bicarbonate Nutrition 0.000 claims abstract description 11
229910000028 potassium bicarbonate Inorganic materials 0.000 claims abstract description 11
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims abstract description 11
150000001734 carboxylic acid salts Chemical class 0.000 claims abstract description 7
230000001172 regenerating effect Effects 0.000 claims abstract description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 188
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical group [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 140
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 126
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 94
235000011056 potassium acetate Nutrition 0.000 claims description 70
239000003245 coal Substances 0.000 claims description 53
239000001569 carbon dioxide Substances 0.000 claims description 47
229910002092 carbon dioxide Inorganic materials 0.000 claims description 47
229910052700 potassium Inorganic materials 0.000 claims description 47
239000011591 potassium Substances 0.000 claims description 47
-1 potassium aromatic carboxylate Chemical class 0.000 claims description 40
238000007254 oxidation reaction Methods 0.000 claims description 39
150000003839 salts Chemical class 0.000 claims description 37
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 36
230000003647 oxidation Effects 0.000 claims description 35
239000007789 gas Substances 0.000 claims description 30
238000006317 isomerization reaction Methods 0.000 claims description 27
239000003054 catalyst Substances 0.000 claims description 21
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 19
OKIIEJOIXGHUKX-UHFFFAOYSA-L cadmium iodide Chemical group [Cd+2].[I-].[I-] OKIIEJOIXGHUKX-UHFFFAOYSA-L 0.000 claims description 16
239000002802 bituminous coal Substances 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 11
230000001590 oxidative effect Effects 0.000 claims description 10
229940075417 cadmium iodide Drugs 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 6
BWILYWWHXDGKQA-UHFFFAOYSA-M potassium propanoate Chemical group [K+].CCC([O-])=O BWILYWWHXDGKQA-UHFFFAOYSA-M 0.000 claims description 5
WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical group [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 claims description 4
239000004331 potassium propionate Substances 0.000 claims description 4
235000010332 potassium propionate Nutrition 0.000 claims description 4
239000003518 caustics Substances 0.000 claims description 3
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 2
230000001376 precipitating effect Effects 0.000 claims 2
230000003301 hydrolyzing effect Effects 0.000 claims 1
229960000583 acetic acid Drugs 0.000 description 51
239000000243 solution Substances 0.000 description 43
239000007787 solid Substances 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 24
235000007686 potassium Nutrition 0.000 description 24
229960003975 potassium Drugs 0.000 description 24
239000007788 liquid Substances 0.000 description 22
239000000047 product Substances 0.000 description 22
150000007513 acids Chemical class 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000012716 precipitator Substances 0.000 description 18
239000003513 alkali Substances 0.000 description 11
238000004519 manufacturing process Methods 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
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
238000001914 filtration Methods 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
159000000032 aromatic acids Chemical class 0.000 description 7
230000020477 pH reduction Effects 0.000 description 7
238000000926 separation method 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
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
229910052784 alkaline earth metal Inorganic materials 0.000 description 5
235000010233 benzoic acid Nutrition 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000011280 coal tar Substances 0.000 description 5
238000000605 extraction Methods 0.000 description 5
238000002156 mixing Methods 0.000 description 5
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
238000001556 precipitation Methods 0.000 description 5
239000011343 solid material Substances 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
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
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 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
239000003077 lignite Substances 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
239000003415 peat 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
230000008929 regeneration Effects 0.000 description 4
238000011069 regeneration method Methods 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
235000011941 Tilia x europaea Nutrition 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
150000001342 alkaline earth 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
150000001491 aromatic compounds Chemical class 0.000 description 3
229910052793 cadmium Inorganic materials 0.000 description 3
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 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
239000003795 chemical substances by application Substances 0.000 description 3
238000005660 chlorination reaction Methods 0.000 description 3
239000000571 coke Substances 0.000 description 3
238000010924 continuous production Methods 0.000 description 3
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 3
229940093915 gynecological organic acid Drugs 0.000 description 3
229910001385 heavy metal Inorganic materials 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000004571 lime Substances 0.000 description 3
XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 3
239000002609 medium Substances 0.000 description 3
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
238000006396 nitration reaction Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003921 oil Substances 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
159000000001 potassium salts Chemical class 0.000 description 3
230000001737 promoting effect Effects 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
238000000638 solvent extraction Methods 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
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 3
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
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
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 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
229960004365 benzoic acid Drugs 0.000 description 2
YUOUKRIPFJKDJY-UHFFFAOYSA-L beryllium;diacetate Chemical compound [Be+2].CC([O-])=O.CC([O-])=O YUOUKRIPFJKDJY-UHFFFAOYSA-L 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
VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
239000001639 calcium acetate Substances 0.000 description 2
235000011092 calcium acetate Nutrition 0.000 description 2
229960005147 calcium acetate Drugs 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000001816 cooling Methods 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
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 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
XKPJKVVZOOEMPK-UHFFFAOYSA-M lithium;formate Chemical compound [Li+].[O-]C=O XKPJKVVZOOEMPK-UHFFFAOYSA-M 0.000 description 2
AXMOZGKEVIBBCF-UHFFFAOYSA-M lithium;propanoate Chemical compound [Li+].CCC([O-])=O AXMOZGKEVIBBCF-UHFFFAOYSA-M 0.000 description 2
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 2
235000011285 magnesium acetate Nutrition 0.000 description 2
239000011654 magnesium acetate Substances 0.000 description 2
229940069446 magnesium acetate Drugs 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
235000019260 propionic acid Nutrition 0.000 description 2
238000000746 purification Methods 0.000 description 2
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 2
238000011084 recovery Methods 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 2
239000004324 sodium propionate Substances 0.000 description 2
235000010334 sodium propionate Nutrition 0.000 description 2
229960003212 sodium propionate Drugs 0.000 description 2
241000894007 species Species 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance 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
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 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
240000005020 Acaciella glauca Species 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
241001292274 Eumenes Species 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-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
241000212342 Sium Species 0.000 description 1
239000004280 Sodium formate Substances 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
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
125000001931 aliphatic group Chemical group 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
150000001601 aromatic carbocyclic compounds Chemical class 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
150000001555 benzenes Chemical class 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
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
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
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
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 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
GOMCKELMLXHYHH-UHFFFAOYSA-L dipotassium;phthalate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=CC=C1C([O-])=O GOMCKELMLXHYHH-UHFFFAOYSA-L 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
239000005457 ice water Substances 0.000 description 1
238000000622 liquid--liquid extraction Methods 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
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 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
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910017604 nitric acid 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
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-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
239000003495 polar organic solvent Substances 0.000 description 1
239000004300 potassium benzoate Substances 0.000 description 1
235000010235 potassium benzoate Nutrition 0.000 description 1
229940103091 potassium benzoate Drugs 0.000 description 1
235000019396 potassium bromate Nutrition 0.000 description 1
229940094037 potassium bromate Drugs 0.000 description 1
238000011085 pressure filtration Methods 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
239000011833 salt mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000003079 shale oil Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000015424 sodium 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
159000000000 sodium salts Chemical class 0.000 description 1
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 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
239000000725 suspension Substances 0.000 description 1
238000007669 thermal treatment Methods 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 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
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 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
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc 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)

CA000322657A 1978-03-06 1979-03-02 Procede de production de l'acide carboxylique et de l'acide carboxylique aromatique Expired CA1120055A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US88393578A	1978-03-06	1978-03-06
US883,935		1978-03-06

Publications (1)

Publication Number	Publication Date
CA1120055A true CA1120055A (fr)	1982-03-16

Family

ID=25383619

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000322657A Expired CA1120055A (fr)	1978-03-06	1979-03-02	Procede de production de l'acide carboxylique et de l'acide carboxylique aromatique

Country Status (1)

Country	Link
CA (1)	CA1120055A (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
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CN113924282A (zh) *	2019-06-12	2022-01-11	诺力昂化学品国际有限公司	用于从含水侧流中分离羧酸的方法
US11976034B2 (en)	2019-06-12	2024-05-07	Nouryon Chemicals International B.V.	Process for the production of diacyl peroxides
US11976035B2 (en)	2019-06-12	2024-05-07	Nouryon Chemicals International B.V.	Process for the production of diacyl peroxides
US12209065B2 (en)	2019-06-12	2025-01-28	Nouryon Chemicals International B.V.	Process for the production of diacyl peroxides
US12215074B2 (en)	2019-06-12	2025-02-04	Nouryon Chemicals International B.V.	Process for the production of peroxyesters

1979
- 1979-03-02 CA CA000322657A patent/CA1120055A/fr not_active Expired

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113924282A (zh) *	2019-06-12	2022-01-11	诺力昂化学品国际有限公司	用于从含水侧流中分离羧酸的方法
CN113924282B (zh) *	2019-06-12	2023-09-12	诺力昂化学品国际有限公司	用于从含水侧流中分离羧酸的方法
US11976034B2 (en)	2019-06-12	2024-05-07	Nouryon Chemicals International B.V.	Process for the production of diacyl peroxides
US11976035B2 (en)	2019-06-12	2024-05-07	Nouryon Chemicals International B.V.	Process for the production of diacyl peroxides
US12209065B2 (en)	2019-06-12	2025-01-28	Nouryon Chemicals International B.V.	Process for the production of diacyl peroxides
US12215074B2 (en)	2019-06-12	2025-02-04	Nouryon Chemicals International B.V.	Process for the production of peroxyesters

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
US3840641A (en)	1974-10-08	Recovery of bromine from tere-and isophthalic acid process residues
US20250236836A1 (en)	2025-07-24	Method for separating biomass from solid fermentation product
US3484458A (en)	1969-12-16	Trimellitic acid production and recovery of intramolecular anhydride
US4345098A (en)	1982-08-17	Process for producing benzene carboxylic acid salts and their acids
CA1120055A (fr)	1982-03-16	Procede de production de l'acide carboxylique et de l'acide carboxylique aromatique
CA1335690C (fr)	1995-05-30	Procede pour la production d'ammoniac et de dioxyde de soufre
KR20010085545A (ko)	2001-09-07	염-함유 반응 혼합물로부터의 촉매 전이 금속의 회수방법
DE2400012A1 (de)	1974-07-25	Verfahren zur umwandlung eines alkalisalzes einer aromatischen carbonsaeure in eine aromatische polycarbonsaeure
US4625056A (en)	1986-11-25	Process for producing benzene carboxylic acids from aromatic material utilizing an aliphatic organic acid agent
US2930813A (en)	1960-03-29	Process for the preparation of cyclic dicarboxylic acids
KR101943115B1 (ko)	2019-01-28	필터 공급 슬러리중 물의 백분율을 제어함으로써 테레프탈산 퍼지 여과 속도를 개선하는 방법
US4375553A (en)	1983-03-01	Process for producing benzene carboxylic acid salts from aromatic materials
CA1120056A (fr)	1982-03-16	Procede de production d'acide carboxylique aromatique isomerise et d'acide terephtalique
US4294977A (en)	1981-10-13	Process for producing aromatic carboxylic acids
KR101946657B1 (ko)	2019-02-11	필터 공급 슬러리중 물의 백분율을 제어함으로써 테레프탈산 퍼지 여과 속도를 개선하는 방법
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US3780096A (en)	1973-12-18	Process for recovering cobalt and manganese oxidation catalysts
US2723995A (en)	1955-11-15	Process for recovering benzoic and toluic acids
US2938050A (en)	1960-05-24	Process for the recovery of terephthalic acid and alkalies from solutions containing alkali metal salts of terephthalic acid
CA1085879A (fr)	1980-09-16	Separation continue des hydro-carbures qui ne contiennent pas de paraffine de ceux qui en contiennent
CN1040417C (zh)	1998-10-28	一种从变含水氯化物浸提液生成含水氯化物浸提剂的方法
JPS6056127B2 (ja)	1985-12-09	酢酸の回収法
SU495821A3 (ru)	1975-12-15	Способ получени поликарбоновых кислот
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