DE2837457A1 - Verfahren zur herstellung von benzoesaeureanhydrid - Google Patents
Verfahren zur herstellung von benzoesaeureanhydridInfo
- Publication number
- DE2837457A1 DE2837457A1 DE19782837457 DE2837457A DE2837457A1 DE 2837457 A1 DE2837457 A1 DE 2837457A1 DE 19782837457 DE19782837457 DE 19782837457 DE 2837457 A DE2837457 A DE 2837457A DE 2837457 A1 DE2837457 A1 DE 2837457A1
- Authority
- DE
- Germany
- Prior art keywords
- benzotrichloride
- reaction
- benzoic acid
- reaction mixture
- process according
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title description 6
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 46
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 239000005711 Benzoic acid Substances 0.000 claims description 22
- 235000010233 benzoic acid Nutrition 0.000 claims description 22
- 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 19
- 239000011541 reaction mixture Substances 0.000 claims description 17
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000011261 inert gas Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 7
- 239000006227 byproduct Substances 0.000 claims description 4
- 238000002360 preparation method Methods 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
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- 238000004821 distillation Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 239000000203 mixture 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
- 238000013459 approach Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000000926 separation method 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-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
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens 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
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- KZEDYLISAAEVLT-UHFFFAOYSA-N 1,2-dichlorobutane Chemical compound [CH2]CC(Cl)CCl KZEDYLISAAEVLT-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- -1 alkyl radicals 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
- 238000012937 correction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009183 running Effects 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 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)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782837457 DE2837457A1 (de) | 1978-08-28 | 1978-08-28 | Verfahren zur herstellung von benzoesaeureanhydrid |
| DE7979103006T DE2960066D1 (en) | 1978-08-28 | 1979-08-17 | Process for the preparation of benzoic acid anhydride |
| EP79103006A EP0008445B1 (de) | 1978-08-28 | 1979-08-17 | Verfahren zur Herstellung von Benzoesäureanhydrid |
| IL58104A IL58104A (en) | 1978-08-28 | 1979-08-24 | Process for the preparation of benzoic ahnydride |
| HU79BA3837A HU180424B (en) | 1978-08-28 | 1979-08-27 | Process for preparing benzoic acid anhydride |
| JP10825279A JPS5533492A (en) | 1978-08-28 | 1979-08-27 | Manufacture of benzoic anhydride |
| DK356779A DK356779A (da) | 1978-08-28 | 1979-08-27 | Femgangsmaade til fremstilling af benzoesyreanhydrid |
| BR7905480A BR7905480A (pt) | 1978-08-28 | 1979-08-27 | Processo para a preparacao de anidrido de acido benzoico |
| CS795846A CS208132B2 (en) | 1978-08-28 | 1979-08-28 | Method of making the anhydride of the benzoic acid |
| US06/703,373 US4562010A (en) | 1978-08-28 | 1985-02-20 | Process for the preparation of benzoic anhydride |
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 |
|---|---|
| DE2837457A1 true DE2837457A1 (de) | 1980-03-20 |
Family
ID=6048062
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782837457 Withdrawn DE2837457A1 (de) | 1978-08-28 | 1978-08-28 | Verfahren zur herstellung von benzoesaeureanhydrid |
| DE7979103006T Expired DE2960066D1 (en) | 1978-08-28 | 1979-08-17 | Process for the preparation of benzoic acid anhydride |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE7979103006T Expired DE2960066D1 (en) | 1978-08-28 | 1979-08-17 | Process for the preparation of 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 EP EP79103006A patent/EP0008445B1/de not_active Expired
- 1979-08-17 DE DE7979103006T patent/DE2960066D1/de not_active Expired
- 1979-08-24 IL IL58104A patent/IL58104A/xx unknown
- 1979-08-27 BR BR7905480A patent/BR7905480A/pt unknown
- 1979-08-27 HU HU79BA3837A patent/HU180424B/hu unknown
- 1979-08-27 JP JP10825279A patent/JPS5533492A/ja active Granted
- 1979-08-27 DK DK356779A patent/DK356779A/da unknown
- 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 |
|---|---|
| DK356779A (da) | 1980-02-29 |
| BR7905480A (pt) | 1980-05-13 |
| EP0008445B1 (de) | 1980-12-10 |
| IL58104A0 (en) | 1979-12-30 |
| EP0008445A1 (de) | 1980-03-05 |
| JPS626698B2 (enExample) | 1987-02-13 |
| CS208132B2 (en) | 1981-08-31 |
| HU180424B (en) | 1983-03-28 |
| JPS5533492A (en) | 1980-03-08 |
| IL58104A (en) | 1982-01-31 |
| US4562010A (en) | 1985-12-31 |
| DE2960066D1 (en) | 1981-02-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |