CH497366A - Verfahren zum Isomerisieren von Cyclohexen-1,2-dicarbonsäureanhydriden - Google Patents
Verfahren zum Isomerisieren von Cyclohexen-1,2-dicarbonsäureanhydridenInfo
- Publication number
- CH497366A CH497366A CH680968A CH680968A CH497366A CH 497366 A CH497366 A CH 497366A CH 680968 A CH680968 A CH 680968A CH 680968 A CH680968 A CH 680968A CH 497366 A CH497366 A CH 497366A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- anhydride
- cyclohexene
- heated
- dicarboxylic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical class C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 title claims description 10
- 239000000203 mixture Substances 0.000 claims description 21
- 150000008064 anhydrides Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- WRUAHXANJKHFIL-UHFFFAOYSA-N benzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1 WRUAHXANJKHFIL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- ZPBSAMLXSQCSOX-UHFFFAOYSA-N naphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 ZPBSAMLXSQCSOX-UHFFFAOYSA-N 0.000 claims description 3
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 238000006317 isomerization reaction Methods 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 7
- -1 m-benzenedisulfonic acid p-benzenedisulfonic acid 4-bromo-m-benzenedisulfonic acid 5-bromo-m-benzenedisulfonic acid 4-chloro-m-benzenedisulfonic acid Toluene-2,4-disulfonic acid Chemical compound 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012263 liquid product Substances 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- YDPFPDNDNZUKPL-UHFFFAOYSA-N 3-nitronaphthalene-1,5-disulfonic acid Chemical compound C1=C([N+]([O-])=O)C=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O YDPFPDNDNZUKPL-UHFFFAOYSA-N 0.000 description 1
- MXLDGDMDLFFRSO-UHFFFAOYSA-N 3-propan-2-ylcyclohex-4-ene-1,2-dicarboxylic acid Chemical compound C(C)(C)C1C(C(CC=C1)C(=O)O)C(=O)O MXLDGDMDLFFRSO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WANXEWXPCZUFDX-UHFFFAOYSA-N CC(C(S(O)(=O)=O)=CC(Br)=C1)=C1S(O)(=O)=O Chemical compound CC(C(S(O)(=O)=O)=CC(Br)=C1)=C1S(O)(=O)=O WANXEWXPCZUFDX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- MHWVMMHIJHHXQP-UHFFFAOYSA-N benzene-1,2,3-trisulfonic acid Chemical class OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1S(O)(=O)=O MHWVMMHIJHHXQP-UHFFFAOYSA-N 0.000 description 1
- MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000006227 byproduct Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical class C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- ROZRLDJKXCKWCD-UHFFFAOYSA-N naphthalene-1,2,3,4-tetrasulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=C(S(O)(=O)=O)C(S(O)(=O)=O)=C21 ROZRLDJKXCKWCD-UHFFFAOYSA-N 0.000 description 1
- GPUMPJNVOBTUFM-UHFFFAOYSA-N naphthalene-1,2,3-trisulfonic acid Chemical class C1=CC=C2C(S(O)(=O)=O)=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC2=C1 GPUMPJNVOBTUFM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63709067A | 1967-05-09 | 1967-05-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH497366A true CH497366A (de) | 1970-10-15 |
Family
ID=24554496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH680968A CH497366A (de) | 1967-05-09 | 1968-05-07 | Verfahren zum Isomerisieren von Cyclohexen-1,2-dicarbonsäureanhydriden |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3487092A (enExample) |
| CH (1) | CH497366A (enExample) |
| DE (1) | DE1768379A1 (enExample) |
| FR (1) | FR1561836A (enExample) |
| GB (1) | GB1164965A (enExample) |
| NL (1) | NL6806478A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3996249A (en) * | 1971-03-10 | 1976-12-07 | Koppers Company, Inc. | Isomerization process |
| US4273719A (en) * | 1979-11-21 | 1981-06-16 | New Japan Chemical Company, Ltd. | Process for preparing 3,4,5,6-tetrahydrophthalic anhydrides or derivatives thereof |
| FR2472568A1 (fr) * | 1979-11-29 | 1981-07-03 | New Japan Chem Co Ltd | Procede de preparation d'anhydrides 3,4,5,6-tetrahydrophtaliques ou de leurs derives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2959599A (en) * | 1956-11-19 | 1960-11-08 | Allied Chem | Isomerization of cyclohexene-1, 2-dicarboxylic anhydrides |
-
1967
- 1967-05-09 US US637090A patent/US3487092A/en not_active Expired - Lifetime
-
1968
- 1968-04-26 GB GB09943/68A patent/GB1164965A/en not_active Expired
- 1968-05-07 DE DE19681768379 patent/DE1768379A1/de active Pending
- 1968-05-07 CH CH680968A patent/CH497366A/de not_active IP Right Cessation
- 1968-05-08 NL NL6806478A patent/NL6806478A/xx unknown
- 1968-05-08 FR FR1561836D patent/FR1561836A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1768379A1 (de) | 1972-01-13 |
| US3487092A (en) | 1969-12-30 |
| GB1164965A (en) | 1969-09-24 |
| NL6806478A (enExample) | 1968-11-11 |
| FR1561836A (enExample) | 1969-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |