DE2102476C3 - Verfahren zur Reinigung von o-Hydroxydiphenyl - Google Patents
Verfahren zur Reinigung von o-HydroxydiphenylInfo
- Publication number
- DE2102476C3 DE2102476C3 DE2102476A DE2102476A DE2102476C3 DE 2102476 C3 DE2102476 C3 DE 2102476C3 DE 2102476 A DE2102476 A DE 2102476A DE 2102476 A DE2102476 A DE 2102476A DE 2102476 C3 DE2102476 C3 DE 2102476C3
- Authority
- DE
- Germany
- Prior art keywords
- hydroxydiphenyl
- percent
- weight
- crystallization
- diphenyl
- 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
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 9
- 238000000746 purification Methods 0.000 title description 7
- 238000002425 crystallisation Methods 0.000 claims description 26
- 230000008025 crystallization Effects 0.000 claims description 26
- 235000010290 biphenyl Nutrition 0.000 claims description 19
- 239000004305 biphenyl Substances 0.000 claims description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 19
- 125000006267 biphenyl group Chemical group 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 16
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 claims description 15
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 14
- TYDSIOSLHQWFOU-UHFFFAOYSA-N 2-cyclohexylidenecyclohexan-1-one Chemical compound O=C1CCCCC1=C1CCCCC1 TYDSIOSLHQWFOU-UHFFFAOYSA-N 0.000 claims description 7
- 239000000155 melt Substances 0.000 claims description 7
- DRLVMOAWNVOSPE-UHFFFAOYSA-N 2-phenylcyclohexan-1-one Chemical compound O=C1CCCCC1C1=CC=CC=C1 DRLVMOAWNVOSPE-UHFFFAOYSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- UOBQDYFTAJKQAL-UHFFFAOYSA-N 2-cyclohexylcyclohexan-1-one Chemical compound O=C1CCCCC1C1CCCCC1 UOBQDYFTAJKQAL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- GVNVAWHJIKLAGL-NSHDSACASA-N (2s)-2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCC[C@H]1C1=CCCCC1 GVNVAWHJIKLAGL-NSHDSACASA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 description 15
- 239000013078 crystal Substances 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 10
- 239000012452 mother liquor Substances 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000004508 fractional distillation Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- -1 o-hydroxyphenyl Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000218157 Aquilegia vulgaris Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/868—Chromium copper and chromium
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2102476A DE2102476C3 (de) | 1970-10-10 | 1971-01-20 | Verfahren zur Reinigung von o-Hydroxydiphenyl |
| AU34149/71A AU457367B2 (en) | 1970-10-10 | 1971-10-05 | Process for the manufacture of highly-purified 2-hydroxydiphenyl using a new catalyst |
| CH410275A CH566948A5 (enrdf_load_stackoverflow) | 1970-10-10 | 1971-10-07 | |
| CA124,655A CA952538A (en) | 1970-10-10 | 1971-10-07 | Process for the manufacture of highly-purified 2-hydrozydiphenyl using a new catalyst |
| CH1465171A CH563808A5 (enrdf_load_stackoverflow) | 1970-10-10 | 1971-10-07 | |
| NL7113876.A NL166915C (nl) | 1970-10-10 | 1971-10-08 | Werkwijze voor het bereiden van zeer zuiver 2-hydroxybifenyl door dehydrogenering van geheel of gedeeltelijk gehydrogeneerd 2-hydroxybifenyl onder toe- passing van een nieuwe katalysator. |
| GB4696171A GB1362284A (en) | 1970-10-10 | 1971-10-08 | Process for the production of a catalyst and its use in the produ ction of hydroxy-diphenyls |
| FR7136350A FR2111179A5 (enrdf_load_stackoverflow) | 1970-10-10 | 1971-10-08 | |
| ZA716764A ZA716764B (en) | 1971-01-20 | 1971-10-08 | Process for the purification of o-hydroxydiphenyl |
| FR7136351A FR2122841A5 (enrdf_load_stackoverflow) | 1970-10-10 | 1971-10-08 | |
| GB4696271A GB1340370A (en) | 1970-10-10 | 1971-10-08 | Process for the purification of o-hydroxydiphenyl |
| IT53353/71A IT939518B (it) | 1971-01-20 | 1971-10-08 | Procedimento ed impianto per depurare o idrossidifenile |
| BE773687A BE773687A (en) | 1971-01-20 | 1971-10-08 | Pure 2-hydroxydiphenyl prepn. - by fractional distillation followed by recrystallisation |
| ES395887A ES395887A1 (es) | 1971-01-20 | 1971-10-09 | Procedimiento para la purificacion de o-hidroxidifenilo. |
| JP8010771A JPS541699B1 (enrdf_load_stackoverflow) | 1970-10-10 | 1971-10-11 | |
| GB4270572A GB1362285A (en) | 1970-10-10 | 1972-09-14 | Process for the production of a catalyst and its use in the produc tion of hydroxy-diphenyls |
| US442156A US3923695A (en) | 1970-10-10 | 1974-02-13 | Catalyst for manufacturing highly purified 2-hydroxy-diphenyl catalyst and method of preparing catalyst |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2049809A DE2049809C3 (de) | 1970-10-10 | 1970-10-10 | Dehydrierungskatalysator |
| DE2102476A DE2102476C3 (de) | 1970-10-10 | 1971-01-20 | Verfahren zur Reinigung von o-Hydroxydiphenyl |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2102476A1 DE2102476A1 (de) | 1972-08-03 |
| DE2102476B2 DE2102476B2 (de) | 1973-08-02 |
| DE2102476C3 true DE2102476C3 (de) | 1974-02-28 |
Family
ID=25759865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2102476A Expired DE2102476C3 (de) | 1970-10-10 | 1971-01-20 | Verfahren zur Reinigung von o-Hydroxydiphenyl |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS541699B1 (enrdf_load_stackoverflow) |
| AU (1) | AU457367B2 (enrdf_load_stackoverflow) |
| CA (1) | CA952538A (enrdf_load_stackoverflow) |
| CH (2) | CH566948A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2102476C3 (enrdf_load_stackoverflow) |
| FR (2) | FR2122841A5 (enrdf_load_stackoverflow) |
| GB (2) | GB1340370A (enrdf_load_stackoverflow) |
| NL (1) | NL166915C (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5136445A (en) * | 1974-09-21 | 1976-03-27 | Sumitomo Chemical Co | Oo fuenirufuenooru no seiseiho |
| DE2520893C2 (de) * | 1975-05-10 | 1982-03-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Diphenylamin |
| JPS6129655U (ja) * | 1984-07-28 | 1986-02-22 | 行雄 栗田 | 書画類掲示具 |
| CN102399135A (zh) * | 2010-09-09 | 2012-04-04 | 东营远大化工有限公司 | 一种邻苯基苯酚的制备和分离精制方法 |
| US8884075B2 (en) | 2010-10-11 | 2014-11-11 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| CN115745750B (zh) * | 2022-09-28 | 2023-12-15 | 山东天隅新材料科技有限公司 | 邻苯基苯酚、制备方法及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1108221B (de) * | 1959-03-21 | 1961-06-08 | Bayer Ag | Verfahren zur Lenkung der Wirkungsweise von Dehydrierungskatalysatoren fuer hydroaromatische Verbindungen |
| DE2049809C3 (de) * | 1970-10-10 | 1975-10-30 | Bayer Ag, 5090 Leverkusen | Dehydrierungskatalysator |
-
1971
- 1971-01-20 DE DE2102476A patent/DE2102476C3/de not_active Expired
- 1971-10-05 AU AU34149/71A patent/AU457367B2/en not_active Expired
- 1971-10-07 CA CA124,655A patent/CA952538A/en not_active Expired
- 1971-10-07 CH CH410275A patent/CH566948A5/xx not_active IP Right Cessation
- 1971-10-07 CH CH1465171A patent/CH563808A5/xx not_active IP Right Cessation
- 1971-10-08 FR FR7136351A patent/FR2122841A5/fr not_active Expired
- 1971-10-08 NL NL7113876.A patent/NL166915C/xx not_active IP Right Cessation
- 1971-10-08 GB GB4696271A patent/GB1340370A/en not_active Expired
- 1971-10-08 GB GB4696171A patent/GB1362284A/en not_active Expired
- 1971-10-08 FR FR7136350A patent/FR2111179A5/fr not_active Expired
- 1971-10-11 JP JP8010771A patent/JPS541699B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1340370A (en) | 1973-12-12 |
| JPS541699B1 (enrdf_load_stackoverflow) | 1979-01-27 |
| AU457367B2 (en) | 1975-01-30 |
| CA952538A (en) | 1974-08-06 |
| CH566948A5 (enrdf_load_stackoverflow) | 1975-09-30 |
| CH563808A5 (enrdf_load_stackoverflow) | 1975-07-15 |
| GB1362284A (en) | 1974-08-07 |
| FR2122841A5 (enrdf_load_stackoverflow) | 1972-09-01 |
| NL7113876A (enrdf_load_stackoverflow) | 1972-04-12 |
| DE2102476A1 (de) | 1972-08-03 |
| AU3414971A (en) | 1973-04-19 |
| NL166915B (nl) | 1981-05-15 |
| FR2111179A5 (enrdf_load_stackoverflow) | 1972-06-02 |
| DE2102476B2 (de) | 1973-08-02 |
| NL166915C (nl) | 1981-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |