US1931057A - Refining phenols - Google Patents
Refining phenols Download PDFInfo
- Publication number
- US1931057A US1931057A US547790A US54779031A US1931057A US 1931057 A US1931057 A US 1931057A US 547790 A US547790 A US 547790A US 54779031 A US54779031 A US 54779031A US 1931057 A US1931057 A US 1931057A
- Authority
- US
- United States
- Prior art keywords
- refining
- phenols
- cresols
- phenol
- cresol
- 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 - Lifetime
Links
- 238000007670 refining Methods 0.000 title description 8
- 150000002989 phenols Chemical class 0.000 title description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 150000001896 cresols Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 4
- -1 alkaline earth metal carbonates Chemical class 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000350158 Prioria balsamifera Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- C07C37/68—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
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
Definitions
- This invention relates to the refining of cresols or phenols or mixtures thereof such as is ob-v tained, for example, from coal tar distillates,
- the object of this invention is to provide a method of refining crude phenol of the type described whereby a colorless product capable of resisting discoloration even in the presence of sunlight for relatively long periods of time may be obtained.
- One method of proceedingv consists in adding to cresol before or after the phenol has been separated therefrom and which may consist of one or more of the cresol isomers, approximately 1% by weight of soda ash. A slight evolution of carbon dioxide will generally be observed.
- the mixture is distilled according to the usual practice. A small amount of residue remains, which consists large- 1y ofunreacted soda ash together with a small amount of the salts of coal tar acid impurities.
- the product is colorless and does not discolor appreciably-even after several weeks. Without the addition of the soda ash the distilled product retains' a charaeteristicpink or brown coloration even after repeateddistillation and turns a dark 40 red or brown after but a few days.
- alkali metal carbonates and bicarbonates are particularly well suited, a variety of inorganic bases may be employ-ed. including the alkaline earth metal carbonates and bicarbonates, as well aaoxid'es or hydroxides, the alkali metal hydroxides or the alkali metal and alkaline earth metal salts of weak acids, such for example as, sodium cresy lates or phenate, which may be obtained by treatin: cresol or phenol withvcaustic soda.
- the method of refining crude phenols which 55 consists in distilling the same after adding thereto a relatively small quantity as compared to the quantity of phenol being treated of an inorganic base.
- the method of refining crude cresols which consists in distilling the same after adding thereto a relatively small quantity as compared'to the quantity of crude cresol being treated of a material selected from a group consisting of the following: the alkali metal carbonates and hydroxides, the alkaline earth metal carbonates, bicarbon'ates, oxides, hydroxides, the alkali and alkaline earth metal cresylates and the bicarbonates of the alkali and alkaline earth metals.
Description
' Patented .Oct. l7, 1933 REFINING PBENOLS I Erik Clemmensen and Boy M. Miller, St. Louis,
Mo., assignors, by mesne assignments, to Monsanto Chemical Company, a corpora on of Delaware No Drawing. Application June 29, 163i Serial No. 547,790
4 Claims. (01. 202-57) This invention relates to the refining of cresols or phenols or mixtures thereof such as is ob-v tained, for example, from coal tar distillates,
and it has particular application tola method of. 5 refining crude cresols-and/ or phenol whereby one -is enabled to remove the color imparting properties and thereby obtain a colorless product which-is stable even in the presence of strong light-for relatively long periods of time.
The object of this invention is to provide a method of refining crude phenol of the type described whereby a colorless product capable of resisting discoloration even in the presence of sunlight for relatively long periods of time may be obtained. V
We'have found that by distilling phenol or cresols'in the presence of a small amount of inorganic bases, either at atmospheric or subatmospheric pressure a colorless relatively light 2 stable product may be obtained.
One method of proceedingv consists in adding to cresol before or after the phenol has been separated therefrom and which may consist of one or more of the cresol isomers, approximately 1% by weight of soda ash. A slight evolution of carbon dioxide will generally be observed. After agitating the mixture of cresol and soda-ash for a short time to insure uniformdistribut'ion of the soda ash in. the charge and'complete' reaction with impurities present, the mixture is distilled according to the usual practice. A small amount of residue remains, which consists large- 1y ofunreacted soda ash together with a small amount of the salts of coal tar acid impurities. The product is colorless and does not discolor appreciably-even after several weeks. Without the addition of the soda ash the distilled product retains' a charaeteristicpink or brown coloration even after repeateddistillation and turns a dark 40 red or brown after but a few days.
While we have found that the alkali metal carbonates and bicarbonates are particularly well suited, a variety of inorganic bases may be employ-ed. including the alkaline earth metal carbonates and bicarbonates, as well aaoxid'es or hydroxides, the alkali metal hydroxides or the alkali metal and alkaline earth metal salts of weak acids, such for example as, sodium cresy lates or phenate, which may be obtained by treatin: cresol or phenol withvcaustic soda.
From the foregoing. description, it will be apparent that this invention affords a simple and eiiective means of improving the quality oijphenol and cresols, that it does not necessitate the installation of special equipment, nor does it require the supervision of a skilled technician.
Although a specific embodiment of the invention is set forth and several modifications have been indicated, it will be apparent that the invention is susceptible to numerable modifications 5 and variations without departing from the substance thereof and we desire, therefore, that it .be limited only as indicated in the claims. 1' I What we claim is: r
1. The method of refining crude phenols which 55 consists in distilling the same after adding thereto a relatively small quantity as compared to the quantity of phenol being treated of an inorganic base. 2. The method of refining crude cresols, which consists in distilling the same after adding thereto a relatively small quantity as compared'to the quantity of crude cresol being treated of a material selected from a group consisting of the following: the alkali metal carbonates and hydroxides, the alkaline earth metal carbonates, bicarbon'ates, oxides, hydroxides, the alkali and alkaline earth metal cresylates and the bicarbonates of the alkali and alkaline earth metals.
3. The method of refining cresols, which comso J prises distilling the same after adding thereto 'a relatively small quantity of alkali or alkaline nan: CLEMMENSEN. ROYM. muss-
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US547790A US1931057A (en) | 1931-06-29 | 1931-06-29 | Refining phenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US547790A US1931057A (en) | 1931-06-29 | 1931-06-29 | Refining phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1931057A true US1931057A (en) | 1933-10-17 |
Family
ID=24186140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US547790A Expired - Lifetime US1931057A (en) | 1931-06-29 | 1931-06-29 | Refining phenols |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1931057A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2656311A (en) * | 1949-10-31 | 1953-10-20 | Gulf Research Development Co | Stabilization of phenol alkylates |
| US2714087A (en) * | 1949-10-31 | 1955-07-26 | Gulf Research Development Co | Stabilization of phenol alkylates |
| US2985687A (en) * | 1957-09-11 | 1961-05-23 | American Cyanamid Co | Purification of beta-naphthol |
| US5344528A (en) * | 1993-08-04 | 1994-09-06 | Aristech Chemical Corporation | Recovery of phenol from low concentrations with sodium sulfate |
-
1931
- 1931-06-29 US US547790A patent/US1931057A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2656311A (en) * | 1949-10-31 | 1953-10-20 | Gulf Research Development Co | Stabilization of phenol alkylates |
| US2714087A (en) * | 1949-10-31 | 1955-07-26 | Gulf Research Development Co | Stabilization of phenol alkylates |
| US2985687A (en) * | 1957-09-11 | 1961-05-23 | American Cyanamid Co | Purification of beta-naphthol |
| US5344528A (en) * | 1993-08-04 | 1994-09-06 | Aristech Chemical Corporation | Recovery of phenol from low concentrations with sodium sulfate |
| WO1995004582A1 (en) * | 1993-08-04 | 1995-02-16 | Aristech Chemical Corporation | Recovery of phenol from low concentrations with sodium sulfate |
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