HU180424B - Process for preparing benzoic acid anhydride - Google Patents
Process for preparing benzoic acid anhydride Download PDFInfo
- Publication number
- HU180424B HU180424B HU79BA3837A HUBA003837A HU180424B HU 180424 B HU180424 B HU 180424B HU 79BA3837 A HU79BA3837 A HU 79BA3837A HU BA003837 A HUBA003837 A HU BA003837A HU 180424 B HU180424 B HU 180424B
- Authority
- HU
- Hungary
- Prior art keywords
- benzoic acid
- process according
- reaction
- trichloride
- benzo
- Prior art date
Links
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 31
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 claims description 28
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 claims description 24
- 235000010233 benzoic acid Nutrition 0.000 claims description 23
- 239000005711 Benzoic acid Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 17
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000011261 inert gas Substances 0.000 claims description 9
- 239000006227 byproduct Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- MQTYQCAVOMQEFJ-UHFFFAOYSA-N benzene;trihydrochloride Chemical compound Cl.Cl.Cl.C1=CC=CC=C1 MQTYQCAVOMQEFJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 239000003049 inorganic solvent Substances 0.000 claims 1
- 229910001867 inorganic solvent Inorganic materials 0.000 claims 1
- 238000004821 distillation Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229960002415 trichloroethylene Drugs 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PQBOTZNYFQWRHU-UHFFFAOYSA-N 1,2-dichlorobutane Chemical compound CCC(Cl)CCl PQBOTZNYFQWRHU-UHFFFAOYSA-N 0.000 description 1
- JFEUBLFAZXRIDL-UHFFFAOYSA-N 5-chloro-5-methylcyclohexa-1,3-diene Chemical compound CC1(Cl)CC=CC=C1 JFEUBLFAZXRIDL-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- FDMAWXYJVNHJIG-UHFFFAOYSA-N ethylbenzene;toluene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1.CCC1=CC=CC=C1 FDMAWXYJVNHJIG-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012066 reaction slurry Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- -1 substituted Chemical class 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 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
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
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 |
|---|---|---|---|
| DE19782837457 DE2837457A1 (de) | 1978-08-28 | 1978-08-28 | Verfahren zur herstellung von benzoesaeureanhydrid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU180424B true HU180424B (en) | 1983-03-28 |
Family
ID=6048062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79BA3837A HU180424B (en) | 1978-08-28 | 1979-08-27 | Process for preparing benzoic acid anhydride |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4562010A (enExample) |
| EP (1) | EP0008445B1 (enExample) |
| JP (1) | JPS5533492A (enExample) |
| BR (1) | BR7905480A (enExample) |
| CS (1) | CS208132B2 (enExample) |
| DE (2) | DE2837457A1 (enExample) |
| DK (1) | DK356779A (enExample) |
| HU (1) | HU180424B (enExample) |
| IL (1) | IL58104A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2904313A1 (fr) * | 2006-07-27 | 2008-02-01 | Rhodia Recherches & Tech | Procede de preparation d'un anhydride d'acide sulfonique |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE368340C (de) * | 1920-07-01 | 1923-02-05 | Wacker Chemie Gmbh | Verfahren zur Darstellung von Saeureanhydriden |
| GB280373A (en) * | 1926-11-29 | 1927-11-17 | British Dyestuffs Corp Ltd | Improvements in the manufacture of aromatic acid anhydrides |
| US3438882A (en) * | 1964-09-11 | 1969-04-15 | Pfizer & Co C | Process for the preparation of oxygencontaining chemical compounds |
-
1978
- 1978-08-28 DE DE19782837457 patent/DE2837457A1/de not_active Withdrawn
-
1979
- 1979-08-17 DE DE7979103006T patent/DE2960066D1/de not_active Expired
- 1979-08-17 EP EP79103006A patent/EP0008445B1/de not_active Expired
- 1979-08-24 IL IL58104A patent/IL58104A/xx unknown
- 1979-08-27 HU HU79BA3837A patent/HU180424B/hu unknown
- 1979-08-27 BR BR7905480A patent/BR7905480A/pt unknown
- 1979-08-27 DK DK356779A patent/DK356779A/da unknown
- 1979-08-27 JP JP10825279A patent/JPS5533492A/ja active Granted
- 1979-08-28 CS CS795846A patent/CS208132B2/cs unknown
-
1985
- 1985-02-20 US US06/703,373 patent/US4562010A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE2837457A1 (de) | 1980-03-20 |
| EP0008445B1 (de) | 1980-12-10 |
| IL58104A0 (en) | 1979-12-30 |
| EP0008445A1 (de) | 1980-03-05 |
| US4562010A (en) | 1985-12-31 |
| DE2960066D1 (en) | 1981-02-19 |
| CS208132B2 (en) | 1981-08-31 |
| IL58104A (en) | 1982-01-31 |
| BR7905480A (pt) | 1980-05-13 |
| JPS626698B2 (enExample) | 1987-02-13 |
| DK356779A (da) | 1980-02-29 |
| JPS5533492A (en) | 1980-03-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3182088A (en) | Method of making a tetrabromobisphenol | |
| US3405040A (en) | Method for recovering tolylene diisocyanate | |
| HU180424B (en) | Process for preparing benzoic acid anhydride | |
| US2615049A (en) | Process for producing chloral | |
| US2652432A (en) | Method of making chlokomethyl | |
| US4736062A (en) | Process for preparing methacrylic acid | |
| US3878243A (en) | Process for preparing perchloromethylmercaptane | |
| JP5858830B2 (ja) | ポリクロロプロパンの製造方法 | |
| EP0074162B1 (en) | Process for producing p-cresol | |
| US2815385A (en) | Process for the production of 2-chloroacrolein and derivatives thereof | |
| US2770639A (en) | Method of producing aliphatic and alicyclic carbonates | |
| US2462221A (en) | Process for the production of acetarylamides | |
| US4992585A (en) | Process for producing α-chloroacetoacetic acid monomethylamide | |
| US2580714A (en) | Production of beta-hydroxy carboxylic acid lactones from ketene and aldehyde with clay catalyst | |
| US3322792A (en) | Production of dichloroacetaldehyde cyclic trimer | |
| US2387341A (en) | Bromination of 2,6-nitro chlor toluene | |
| US3268430A (en) | Process for preparing anhydrous chlorooxirane and chloroacetaldehyde | |
| US4125564A (en) | Process for producing chloroprene | |
| US3590104A (en) | Process for preparing 0,0-dialkyl-0-phenyl phosphorothioates | |
| US2980708A (en) | Epoxy nitrile process | |
| CN109734565B (zh) | 一种原甲酸酯生产方法 | |
| US3076042A (en) | Process thermal reaction between carbon tetrachloride and propylene | |
| US3960915A (en) | Process for the preparation of isopropenyl isocyanate | |
| US2900418A (en) | Production of alkyl phenols | |
| JPH01275590A (ja) | アルキルジハロゲノホスファンの製造法 |