DE1909440C - - Google Patents
Info
- Publication number
- DE1909440C DE1909440C DE19691909440 DE1909440A DE1909440C DE 1909440 C DE1909440 C DE 1909440C DE 19691909440 DE19691909440 DE 19691909440 DE 1909440 A DE1909440 A DE 1909440A DE 1909440 C DE1909440 C DE 1909440C
- Authority
- DE
- Germany
- Prior art keywords
- line
- hydrolysis
- water
- temperature
- terephthalic acid
- Prior art date
- 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
Links
- 238000006460 hydrolysis reaction Methods 0.000 claims description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 61
- 239000002002 slurry Substances 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 150000002825 nitriles Chemical class 0.000 claims description 14
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 11
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000011780 sodium chloride Substances 0.000 claims description 10
- -1 aromatic carboxylic acids Chemical class 0.000 claims description 9
- 230000000875 corresponding Effects 0.000 claims description 9
- 150000003863 ammonium salts Chemical class 0.000 claims description 8
- 230000003197 catalytic Effects 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 31
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- 150000007513 acids Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000012535 impurity Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
- 229920005554 polynitrile Polymers 0.000 description 5
- 235000012970 cakes Nutrition 0.000 description 4
- 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 4
- PCTJSEBRJCZFAQ-UHFFFAOYSA-O C(C1=CC=C(C(=O)N)C=C1)(=O)N.[NH4+] Chemical compound C(C1=CC=C(C(=O)N)C=C1)(=O)N.[NH4+] PCTJSEBRJCZFAQ-UHFFFAOYSA-O 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N Phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- FFPQSNUAVYJZDH-UHFFFAOYSA-N diazanium;terephthalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 FFPQSNUAVYJZDH-UHFFFAOYSA-N 0.000 description 3
- VIQSRHWJEKERKR-UHFFFAOYSA-L disodium;terephthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 VIQSRHWJEKERKR-UHFFFAOYSA-L 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N Benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- RXFTYYPTRLKQEY-UHFFFAOYSA-N C(C1=CC=C(C(=O)N)C=C1)(=O)N.[Na] Chemical compound C(C1=CC=C(C(=O)N)C=C1)(=O)N.[Na] RXFTYYPTRLKQEY-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-M 1-naphthoate Chemical compound C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-M 0.000 description 1
- CYMRPDYINXWJFU-UHFFFAOYSA-N 2-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC=C1C(O)=O CYMRPDYINXWJFU-UHFFFAOYSA-N 0.000 description 1
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 1
- JMHSCWJIDIKGNZ-UHFFFAOYSA-N 4-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=C(C(O)=O)C=C1 JMHSCWJIDIKGNZ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N Isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N Phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 210000004915 Pus Anatomy 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- WUICPPBYLKNKNS-UHFFFAOYSA-N benzene-1,2,3-tricarbonitrile Chemical compound N#CC1=CC=CC(C#N)=C1C#N WUICPPBYLKNKNS-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000001419 dependent Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- AZKDTTQQTKDXLH-UHFFFAOYSA-N naphthalene-2-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CC=C21 AZKDTTQQTKDXLH-UHFFFAOYSA-N 0.000 description 1
- JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71393168A | 1968-03-18 | 1968-03-18 | |
| US71393168 | 1968-03-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1909440A1 DE1909440A1 (de) | 1969-11-13 |
| DE1909440C true DE1909440C (uk) | 1973-07-26 |
Family
ID=24868125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691909440 Granted DE1909440A1 (de) | 1968-03-18 | 1969-02-25 | Verfahren zur Herstellung von aromatischen Carbonsaeuren |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5215588B1 (uk) |
| BE (1) | BE729867A (uk) |
| CH (1) | CH536802A (uk) |
| DE (1) | DE1909440A1 (uk) |
| FR (1) | FR2004194A1 (uk) |
| GB (1) | GB1260755A (uk) |
| IE (1) | IE32675B1 (uk) |
| LU (1) | LU58220A1 (uk) |
| NL (1) | NL163205C (uk) |
| SE (1) | SE362869B (uk) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5763652A (en) * | 1995-03-08 | 1998-06-09 | Daicel Chemical Industries, Ltd. | Process for producing a carboxylic acid |
| FR2764600B1 (fr) * | 1997-06-16 | 1999-08-20 | Atochem Elf Sa | Procede continu de fabrication de solutions aqueuses de sels alcalins d'acides arylacetiques |
| US6075117A (en) * | 1998-12-21 | 2000-06-13 | E.I. Dupont De Nemours & Company | Process for the hydrolysis of adiponitrile and the production of nylon 6,6 using dicarboxylic acids as the sole catalyst |
| US6103863A (en) * | 1998-12-22 | 2000-08-15 | E. I. Dupont De Nemours & Company | Process for preparation of polyamide from dinitrile and diamine |
| US6084056A (en) * | 1998-12-22 | 2000-07-04 | E. I. Dupont De Nemours & Company | Process for the hydrolysis of adiponitrile and the production of nylon 6,6 utilizing low catalyst levels |
| BR0316462A (pt) | 2002-12-09 | 2005-10-11 | Eastman Chem Co | Processos para reduzir uma suspensão de ácido carboxìlico purificado, para purificar um produto de oxidação em estágios, para produzir um produto de ácido carboxìlico purificado, e, suspensão de ácido carboxìlico purificado |
| US7132566B2 (en) | 2003-09-22 | 2006-11-07 | Eastman Chemical Company | Process for the purification of a crude carboxylic acid slurry |
| US7074954B2 (en) | 2002-12-09 | 2006-07-11 | Eastman Chemical Company | Process for the oxidative purification of terephthalic acid |
| US7546747B2 (en) * | 2004-01-15 | 2009-06-16 | Eastman Chemical Company | Process for production of a dried carboxylic acid cake suitable for use in polyester production |
| US8614350B2 (en) | 2008-01-15 | 2013-12-24 | Eastman Chemical Company | Carboxylic acid production process employing solvent from esterification of lignocellulosic material |
| US8455680B2 (en) | 2008-01-15 | 2013-06-04 | Eastman Chemical Company | Carboxylic acid production process employing solvent from esterification of lignocellulosic material |
| CN110590532A (zh) * | 2019-08-14 | 2019-12-20 | 兄弟科技股份有限公司 | 一种芳香酸的绿色合成方法 |
-
1969
- 1969-02-25 DE DE19691909440 patent/DE1909440A1/de active Granted
- 1969-02-28 GB GB1079269A patent/GB1260755A/en not_active Expired
- 1969-03-10 JP JP1828369A patent/JPS5215588B1/ja active Pending
- 1969-03-13 CH CH378169A patent/CH536802A/de not_active IP Right Cessation
- 1969-03-14 BE BE729867D patent/BE729867A/xx not_active IP Right Cessation
- 1969-03-17 LU LU58220D patent/LU58220A1/xx unknown
- 1969-03-18 FR FR6907791A patent/FR2004194A1/fr not_active Withdrawn
- 1969-03-18 IE IE35269A patent/IE32675B1/xx unknown
- 1969-03-18 SE SE377069A patent/SE362869B/xx unknown
- 1969-03-18 NL NL6904134A patent/NL163205C/xx not_active IP Right Cessation
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