GB641662A - Method for making phenol - Google Patents
Method for making phenolInfo
- Publication number
- GB641662A GB641662A GB20152/47A GB2015247A GB641662A GB 641662 A GB641662 A GB 641662A GB 20152/47 A GB20152/47 A GB 20152/47A GB 2015247 A GB2015247 A GB 2015247A GB 641662 A GB641662 A GB 641662A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzene
- reaction
- proportion
- per cent
- hydrogen
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 18
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 239000000852 hydrogen donor Substances 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- PYLMCYQHBRSDND-SOFGYWHQSA-N (E)-2-ethyl-2-hexenal Chemical compound CCC\C=C(/CC)C=O PYLMCYQHBRSDND-SOFGYWHQSA-N 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- 241000779819 Syncarpia glomulifera Species 0.000 abstract 1
- -1 actaldehyde Chemical compound 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 238000010276 construction Methods 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 239000007792 gaseous phase Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001739 pinus spp. Substances 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000011949 solid catalyst Substances 0.000 abstract 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 abstract 1
- 229940036248 turpentine Drugs 0.000 abstract 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
- C07C37/58—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of molecular oxygen
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/919—Apparatus considerations
- Y10S585/92—Apparatus considerations using apparatus of recited composition
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/919—Apparatus considerations
- Y10S585/921—Apparatus considerations using recited apparatus structure
- Y10S585/924—Reactor shape or disposition
- Y10S585/925—Dimension or proportion
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
In the preparation of phenol by passing benzene vapour and an oxygen containing gas at a pressure of more than 500 lbs./sq. inch through a reaction zone at a temperature between 650 DEG F. and 1225 DEG F. in the absence of solid catalyst, the yield is improved by the addition of a minor proportion, i.e. from 0.2 per cent to about 3.0 per cent by volume based on benzene, of an organic compound containing hydrogen, which under the conditions of the reaction is a better hydrogen donor than benzene and is in the gaseous phase and which has a "potential hydrogen donor ability" value, as defined in the Specification, greater than 2.5. Suitable hydrogen donors are cyclohexanol, cyclohexanone, cyclohexene, tetrahydronaphthalene, 2-ethyl-3-propyl acrolein, actaldehyde, n-hexane, diethyl ether, aniline, turpentine, n-hexene, cracked gasoline and particularly cyclohexane. The invention may also be carried out by partially hydrogenating the benzene prior to the oxidation to produce the desired proportion of hydrogen donors. Optimum reaction times, temperatures, proportions and pressures; the dimensions and construction of the reaction tube and the nature and proportion of the inductor are interdependent. Suitable values for the above are indicated. In a preferred embodiment of the invention, the benzene is separated from the phenol and other oxidation products and recycled with the addition at each recycle stage of a further small amount of the reaction promotor. This may be added as such or may be formed in situ by continuously hydrogenating a proportion of the recycled benzene prior to its admission to the reaction zone sufficient to incorporate 0.2-3.0 per cent by volume of hydrogenated benzene. Specification 459,920 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US565927A US2439812A (en) | 1944-11-30 | 1944-11-30 | Method for making phenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB641662A true GB641662A (en) | 1950-08-16 |
Family
ID=24260671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20152/47A Expired GB641662A (en) | 1944-11-30 | 1947-07-25 | Method for making phenol |
Country Status (3)
| Country | Link |
|---|---|
| US (4) | US2439812A (en) |
| DE (1) | DE896652C (en) |
| GB (1) | GB641662A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE938788C (en) * | 1952-12-28 | 1956-02-09 | Bergwerksverband Zur Verwertun | Process for the production of phenol |
| JPS5344423B1 (en) * | 1971-05-28 | 1978-11-29 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2546640A (en) * | 1948-09-21 | 1951-03-27 | Allied Chem & Dye Corp | Production of phenol by oxidation of benzene |
| US2546639A (en) * | 1948-09-21 | 1951-03-27 | Allied Chem & Dye Corp | Production of phenol by oxidation of benzene |
| NL294400A (en) * | 1962-06-21 | |||
| FR2336364A1 (en) * | 1975-12-24 | 1977-07-22 | Rhone Poulenc Ind | HYDROXYLATION OF AROMATIC COMPOUNDS |
| EP0519084B1 (en) * | 1990-12-26 | 1996-10-23 | MITSUI TOATSU CHEMICALS, Inc. | Process for producing simultaneously an aromatic hydroxy compound and a carbonyl compound |
| US9827602B2 (en) | 2015-09-28 | 2017-11-28 | Tesla, Inc. | Closed-loop thermal servicing of solvent-refining columns |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2223383A (en) * | 1937-10-04 | 1940-12-03 | Solvay Process Co | Oxidation of hydrocarbons to phenols |
-
1944
- 1944-11-30 US US565927A patent/US2439812A/en not_active Expired - Lifetime
- 1944-11-30 US US565928A patent/US2440233A/en not_active Expired - Lifetime
-
1945
- 1945-06-05 US US597657A patent/US2415101A/en not_active Expired - Lifetime
- 1945-06-05 US US597658A patent/US2440234A/en not_active Expired - Lifetime
-
1947
- 1947-07-25 GB GB20152/47A patent/GB641662A/en not_active Expired
-
1950
- 1950-09-27 DE DES19737A patent/DE896652C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE938788C (en) * | 1952-12-28 | 1956-02-09 | Bergwerksverband Zur Verwertun | Process for the production of phenol |
| JPS5344423B1 (en) * | 1971-05-28 | 1978-11-29 |
Also Published As
| Publication number | Publication date |
|---|---|
| US2440233A (en) | 1948-04-20 |
| US2415101A (en) | 1947-02-04 |
| US2439812A (en) | 1948-04-20 |
| US2440234A (en) | 1948-04-20 |
| DE896652C (en) | 1953-11-12 |
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