DE2305265A1 - Verfahren zur herstellung von aromatischen carbonsaeuren - Google Patents
Verfahren zur herstellung von aromatischen carbonsaeurenInfo
- Publication number
- DE2305265A1 DE2305265A1 DE19732305265 DE2305265A DE2305265A1 DE 2305265 A1 DE2305265 A1 DE 2305265A1 DE 19732305265 DE19732305265 DE 19732305265 DE 2305265 A DE2305265 A DE 2305265A DE 2305265 A1 DE2305265 A1 DE 2305265A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrolysis
- nitrile
- equivalents
- mole
- cycle
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title description 6
- 150000004653 carbonic acids Chemical class 0.000 title 1
- 230000007062 hydrolysis Effects 0.000 claims description 28
- 238000006460 hydrolysis reaction Methods 0.000 claims description 28
- 150000002825 nitriles Chemical class 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- -1 aromatic nitrile Chemical class 0.000 claims description 7
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 229920006391 phthalonitrile polymer Polymers 0.000 claims description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000011973 solid acid Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- 239000000047 product Substances 0.000 description 28
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 238000010641 nitrile hydrolysis reaction Methods 0.000 description 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 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 5
- 238000004821 distillation Methods 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- FVUKYCZRWSQGAS-UHFFFAOYSA-N 3-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC(C(O)=O)=C1 FVUKYCZRWSQGAS-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 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 2
- 239000002243 precursor Substances 0.000 description 2
- 239000012066 reaction slurry Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 1
- FUKWTMJZHKZKFA-UHFFFAOYSA-N 4-cyanobenzamide Chemical compound NC(=O)C1=CC=C(C#N)C=C1 FUKWTMJZHKZKFA-UHFFFAOYSA-N 0.000 description 1
- ADCUEPOHPCPMCE-UHFFFAOYSA-N 4-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C=C1 ADCUEPOHPCPMCE-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 101150046432 Tril gene Proteins 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009838 combustion analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- ZBFVJRBOKDTSMO-UHFFFAOYSA-N naphthalene-2,6-dicarbonitrile Chemical compound C1=C(C#N)C=CC2=CC(C#N)=CC=C21 ZBFVJRBOKDTSMO-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 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
- 238000010998 test method Methods 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22330672A | 1972-02-03 | 1972-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2305265A1 true DE2305265A1 (de) | 1973-08-23 |
Family
ID=22835938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732305265 Pending DE2305265A1 (de) | 1972-02-03 | 1973-02-02 | Verfahren zur herstellung von aromatischen carbonsaeuren |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4881828A (cs) |
| BE (1) | BE794910A (cs) |
| CA (1) | CA969555A (cs) |
| DE (1) | DE2305265A1 (cs) |
| FR (1) | FR2169995B1 (cs) |
| GB (1) | GB1377333A (cs) |
| IN (1) | IN138900B (cs) |
| IT (1) | IT978344B (cs) |
| NL (1) | NL7301280A (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN111100022A (zh) * | 2019-10-30 | 2020-05-05 | 石家庄市栾城区华英工贸有限责任公司 | 一种路易斯酸催化腈类化合物水解制备羧酸类化合物的方法 |
-
0
- BE BE794910D patent/BE794910A/xx unknown
-
1972
- 1972-11-22 CA CA157,177A patent/CA969555A/en not_active Expired
-
1973
- 1973-01-22 IT IT19449/73A patent/IT978344B/it active
- 1973-01-29 JP JP48011228A patent/JPS4881828A/ja active Pending
- 1973-01-30 NL NL7301280A patent/NL7301280A/xx not_active Application Discontinuation
- 1973-01-30 FR FR7303148A patent/FR2169995B1/fr not_active Expired
- 1973-02-02 DE DE19732305265 patent/DE2305265A1/de active Pending
- 1973-02-02 GB GB524573A patent/GB1377333A/en not_active Expired
- 1973-04-27 IN IN989/CAL/73A patent/IN138900B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2169995B1 (cs) | 1978-12-01 |
| BE794910A (fr) | 1973-08-02 |
| NL7301280A (cs) | 1973-08-07 |
| FR2169995A1 (cs) | 1973-09-14 |
| CA969555A (en) | 1975-06-17 |
| GB1377333A (en) | 1974-12-11 |
| IT978344B (it) | 1974-09-20 |
| IN138900B (cs) | 1976-04-10 |
| JPS4881828A (cs) | 1973-11-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2705022A1 (de) | Verfahren zur herstellung eines kristallinen l-mgda-trialkalimetallsalzes | |
| DE3011391A1 (de) | Verfahren zur reinigung von rohem acetonitril | |
| DE2343599C2 (de) | Verfahren zur Herstellung von Glycin | |
| DE1493198C3 (de) | Verfahren zur Herstellung eines aliphatischen oder cycloaliphatischen Ketoxims | |
| DE2305265A1 (de) | Verfahren zur herstellung von aromatischen carbonsaeuren | |
| DE2814800A1 (de) | Verfahren zur herstellung von guanidin | |
| DE69105828T2 (de) | Verfahren zur herstellung von oxamid. | |
| EP0712830B1 (de) | Verfahren zur Gewinnung von Adipinsäure | |
| DE2259796A1 (de) | Verfahren zum konzentrieren einer waessrigen acrylamidloesung | |
| DE2635484A1 (de) | Verfahren zur hydrolyse von aromatischen nitrilen zu carbonsaeuren | |
| DE2638170B2 (de) | Kontinuierliches Verfahren von Nicotinsäureamid durch Hydrolyse von Nicotinsäurenitril | |
| DE2627052A1 (de) | Verfahren zur herstellung aromatischer carbonsaeuren | |
| DE2700851B2 (de) | Verfahren zur getrennten Gewinnung geradkettiger und verzweigter Carbonsäuren mit 8 bis 22 Kohlenstoffatomen aus Gemischen wasserlöslicher geradkettiger und verzweigter Carbonsäuren | |
| DE2358497A1 (de) | Verfahren zur herstellung von aromatischen carbonsaeuren | |
| CH634827A5 (en) | Process for the preparation of nitroguanidine from guanidine nitrate by dehydration | |
| DE1518358A1 (de) | Verfahren zur Ausscheidung von Methionin oder eines Methioninsalzes aus einer methioninhaltigen waessrigen Ammoniumsulfatloesung | |
| DE2938424A1 (de) | Verfahren zur abtrenunng von mit destillatdaempfen uebergehenden saeuren und basen | |
| DE2256508C3 (de) | Kontinuierliches Verfahren zur Herstellung von Nicotinsäure | |
| DE1443064C (de) | Verfahren zur Gewinnung von Acrylsaureamid | |
| AT233544B (de) | Verfahren zur Herstellung von α-Nitro-ε-caprolactam | |
| DE1231706B (de) | Verfahren zur Herstellung von Adenin und 4, 5-Dicyanimidazol | |
| DE1543448C (cs) | ||
| DE2421291A1 (de) | Verfahren zur optischen spaltung racemischen lysinsulfanilats | |
| DE1618570C3 (de) | Verfahren zur Reinigung von Adipinsäuredinitril | |
| DD144765A1 (de) | Verfahren zur reinigung von acetonitril |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |