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 (fr) | 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 (fr) |
| BE (1) | BE729867A (fr) |
| CH (1) | CH536802A (fr) |
| DE (1) | DE1909440A1 (fr) |
| FR (1) | FR2004194A1 (fr) |
| GB (1) | GB1260755A (fr) |
| IE (1) | IE32675B1 (fr) |
| LU (1) | LU58220A1 (fr) |
| NL (1) | NL163205C (fr) |
| SE (1) | SE362869B (fr) |
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 |
| 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 |
| MXPA05006120A (es) | 2002-12-09 | 2005-08-16 | Eastman Chem Co | Proceso para la purificacion oxidativa de acido tereftalico. |
| 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 SE SE377069A patent/SE362869B/xx unknown
- 1969-03-18 IE IE35269A patent/IE32675B1/xx unknown
- 1969-03-18 NL NL6904134A patent/NL163205C/xx not_active IP Right Cessation
- 1969-03-18 FR FR6907791A patent/FR2004194A1/fr not_active Withdrawn
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