CA1057311A - Process for manufacture of catechol - Google Patents
Process for manufacture of catecholInfo
- Publication number
- CA1057311A CA1057311A CA235,237A CA235237A CA1057311A CA 1057311 A CA1057311 A CA 1057311A CA 235237 A CA235237 A CA 235237A CA 1057311 A CA1057311 A CA 1057311A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- process according
- vanadium
- cyclohexanol
- group
- 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
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 48
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract description 57
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims abstract description 40
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims description 54
- NTUQPJNKERXQPA-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-5-ol Chemical compound OC1CCCC2OC12 NTUQPJNKERXQPA-UHFFFAOYSA-N 0.000 claims description 21
- 229910052720 vanadium Inorganic materials 0.000 claims description 18
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 239000003446 ligand Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 230000018044 dehydration Effects 0.000 claims description 11
- 238000006297 dehydration reaction Methods 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 11
- 238000005984 hydrogenation reaction Methods 0.000 claims description 10
- 239000007791 liquid phase Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000000129 anionic group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 150000002739 metals Chemical class 0.000 claims description 7
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 230000000737 periodic effect Effects 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000012808 vapor phase Substances 0.000 claims description 6
- 239000010457 zeolite Substances 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 229910021536 Zeolite Inorganic materials 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 4
- 239000010948 rhodium Substances 0.000 claims description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 4
- 239000010439 graphite Substances 0.000 claims 4
- 229910002804 graphite Inorganic materials 0.000 claims 4
- 229910052741 iridium Inorganic materials 0.000 claims 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 4
- 229910052762 osmium Inorganic materials 0.000 claims 4
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 abstract description 10
- 239000003039 volatile agent Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 abstract description 2
- PWVHLUKAENFZIA-UHFFFAOYSA-N cyclohexanol;cyclohexanone Chemical compound OC1CCCCC1.O=C1CCCCC1 PWVHLUKAENFZIA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 10
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 8
- 208000005156 Dehydration Diseases 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- PQANGXXSEABURG-UHFFFAOYSA-N cyclohex-2-en-1-ol Chemical compound OC1CCCC=C1 PQANGXXSEABURG-UHFFFAOYSA-N 0.000 description 3
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RHQKKJPJCHGKQO-UHFFFAOYSA-N [Cu+2].[O-][Cr]([O-])=O Chemical class [Cu+2].[O-][Cr]([O-])=O RHQKKJPJCHGKQO-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ZWAJLVLEBYIOTI-OLQVQODUSA-N (1s,6r)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCC[C@@H]2O[C@@H]21 ZWAJLVLEBYIOTI-OLQVQODUSA-N 0.000 description 1
- QHDHNVFIKWGRJR-UHFFFAOYSA-N 1-cyclohexenol Chemical compound OC1=CCCCC1 QHDHNVFIKWGRJR-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- -1 aralkyl hydrocarbon Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011819 refractory material Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| US05/515,762 US3987112A (en) | 1973-06-29 | 1974-10-17 | Process for manufacture of catechol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1057311A true CA1057311A (en) | 1979-06-26 |
Family
ID=24052634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA235,237A Expired CA1057311A (en) | 1974-10-17 | 1975-09-11 | Process for manufacture of catechol |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5165723A (cg-RX-API-DMAC10.html) |
| BE (1) | BE834522A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1057311A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2546050A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2288076A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1529218A (cg-RX-API-DMAC10.html) |
| IT (1) | IT1043433B (cg-RX-API-DMAC10.html) |
| NL (1) | NL7511554A (cg-RX-API-DMAC10.html) |
-
1975
- 1975-09-11 CA CA235,237A patent/CA1057311A/en not_active Expired
- 1975-10-01 NL NL7511554A patent/NL7511554A/xx not_active Application Discontinuation
- 1975-10-13 JP JP12258275A patent/JPS5165723A/ja active Pending
- 1975-10-14 DE DE19752546050 patent/DE2546050A1/de active Pending
- 1975-10-15 BE BE160944A patent/BE834522A/xx unknown
- 1975-10-16 IT IT2837075A patent/IT1043433B/it active
- 1975-10-17 GB GB4282875A patent/GB1529218A/en not_active Expired
- 1975-10-17 FR FR7531770A patent/FR2288076A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1043433B (it) | 1980-02-20 |
| JPS5165723A (ja) | 1976-06-07 |
| NL7511554A (nl) | 1976-04-21 |
| DE2546050A1 (de) | 1976-04-22 |
| GB1529218A (en) | 1978-10-18 |
| BE834522A (fr) | 1976-04-15 |
| FR2288076A1 (fr) | 1976-05-14 |
| FR2288076B1 (cg-RX-API-DMAC10.html) | 1979-06-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101156312B1 (ko) | 레이니 금속 촉매를 이용한 사이클로헥산디메탄올의 제조방법 | |
| EP1836147B1 (en) | Vapour phase hydrogenation of glycerol | |
| TWI731084B (zh) | 從低丁烯原料混合物製造正戊醛 | |
| EP2736867B1 (en) | Integrated process for the preparation of 1,4-cyclohexanedimethanol from terephthalic acid | |
| EP2736866B1 (en) | Process for the preparation of 1,4-cyclohexanedimethanol from terephthalic acid | |
| EP2736868B1 (en) | Process for the preparation of 1,4-cyclohexanedimethanol | |
| WO2013019442A1 (en) | Process for the preparation of 1,3-cyclohexanedimethanol from isophthalic acid | |
| US4093661A (en) | Catalytic decarbonylation of esters | |
| US3968133A (en) | Carboxylation process for preparing linear fatty acids or esters | |
| US4026960A (en) | 2,7,10,15,18,23-Hexamethyltetra-cosane | |
| US2561984A (en) | Production of primary alcohols and aldehydes | |
| US4656297A (en) | Coproduction of butanediol and tetrahydrofuran and their subsequent separation from the reaction product mixture | |
| EP0023379A2 (en) | Method for the preparation of cyclohexanol and/or cyclohexanone | |
| US3987112A (en) | Process for manufacture of catechol | |
| CA1057311A (en) | Process for manufacture of catechol | |
| US3671603A (en) | Butene recovery | |
| CA1052812A (en) | Hydrogenation process of diacetoxybutene | |
| Ipatieff et al. | CONDENSATION OF KETONES WITH ALCOHOLS IN THE PRESENCE OF MIXED CATALYSTS1 | |
| US3347921A (en) | Preparation of anilines from oxygenated cyclohexanes | |
| US3361822A (en) | Process for the selective hydrogenation of unsaturated ketones | |
| US4035428A (en) | Process for production of orthophenylphenol | |
| US20030158453A1 (en) | Preparation of tetrahydrogeraniol | |
| US3278611A (en) | Hydrogenation of aromatic halides | |
| JP2565561B2 (ja) | ７ーオクテンー１ーアールの製造法 | |
| US3890397A (en) | Process for the preparation of 2-naphthole from the corresponding tetralin-hydroperoxide and 1,2-dialin |