ES268796A1 - Production of phenol - Google Patents
Production of phenolInfo
- Publication number
- ES268796A1 ES268796A1 ES0268796A ES268796A ES268796A1 ES 268796 A1 ES268796 A1 ES 268796A1 ES 0268796 A ES0268796 A ES 0268796A ES 268796 A ES268796 A ES 268796A ES 268796 A1 ES268796 A1 ES 268796A1
- Authority
- ES
- Spain
- Prior art keywords
- phenol
- cyclohexane
- range
- fraction
- temperature
- 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 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000012535 impurity Substances 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 238000007710 freezing Methods 0.000 abstract 1
- 230000008014 freezing Effects 0.000 abstract 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 230000008016 vaporization Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
-
- 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
- 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
- C07C37/07—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 with simultaneous reduction of C=O group in that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Phenol is produced from an oxygenated cyclohexane fraction which contains cyclohexanone and/or cyclohexanol and also contains a (non-phenolic) impurity which boils at about the same temperature as phenol, by vaporizing said fraction and diluting it with hydrogen in an amount in the range of 1 to 15 mols. of hydrogen per mol. of total cyclohexanone and cyclohexanol therein, and contacting the resulting mixture with a dehydrogenation catalyst, such as platinum-on-carbon, at a temperature in the range of 250 degrees to 425 degrees at a liquid hourly space velocity in the range of 0.3 to 2.5 per hour, and recovering phenol product as a distillate free from impurity. The charge stock is suitably a fraction boiling in the range of 54 DEG to 94 DEG C. at 23 mm. Hg, and the reaction temperature preferably 375-385 DEG C., and liquid hourly space velocity 0.7 per hour. Phenol having a freezing point of at least 40.0 DEG C. may be recovered by fractionating the reaction product under reduced pressure conditions such that the highest temperature is not over 150 DEG C. The initial fraction may be obtained by air oxidation of cyclohexane at 125-180 DEG C., preferably 130 DEG C. in the presence of cobalt naphthenate until 10% of the cyclohexane is oxidized. After removal of unreacted cyclohexane the mixture is vacuum distilled to obtain the desired cut. Specifications 929,680, 939,613 and 986,932 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4103060A | 1960-07-06 | 1960-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES268796A1 true ES268796A1 (en) | 1961-12-16 |
Family
ID=21914338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0268796A Expired ES268796A1 (en) | 1960-07-06 | 1961-07-05 | Production of phenol |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE605656A (en) |
| ES (1) | ES268796A1 (en) |
| GB (1) | GB986931A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009134514A1 (en) * | 2008-05-01 | 2009-11-05 | Exxonmobil Chemical Patents Inc. | Process for producing cyclohexanone |
| US8222459B2 (en) | 1997-06-13 | 2012-07-17 | Exxonmobil Chemical Patents Inc. | Process for producing cyclohexanone |
| WO2010024975A1 (en) | 2008-08-29 | 2010-03-04 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| US9061270B2 (en) | 2010-02-05 | 2015-06-23 | Exxonmobil Chemical Patents Inc. | Cyclohexanone dehydrogenation catalyst and process |
| WO2011096990A2 (en) | 2010-02-05 | 2011-08-11 | Exxonmobil Chemical Patents Inc. | Dehydrogenation catalyst and process |
| SG185716A1 (en) | 2010-06-25 | 2012-12-28 | Exxonmobil Chem Patents Inc | Dehydrogenation process |
-
1961
- 1961-07-03 BE BE605656A patent/BE605656A/en unknown
- 1961-07-05 ES ES0268796A patent/ES268796A1/en not_active Expired
- 1961-07-06 GB GB24516/61A patent/GB986931A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB986931A (en) | 1965-03-24 |
| BE605656A (en) | 1961-11-03 |
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