US1795382A - Process for obtaining phenols from phenol-bearing industrial liquors - Google Patents
Process for obtaining phenols from phenol-bearing industrial liquors Download PDFInfo
- Publication number
- US1795382A US1795382A US90684A US9068426A US1795382A US 1795382 A US1795382 A US 1795382A US 90684 A US90684 A US 90684A US 9068426 A US9068426 A US 9068426A US 1795382 A US1795382 A US 1795382A
- Authority
- US
- United States
- Prior art keywords
- phenols
- phenol
- liquors
- bases
- obtaining
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title description 21
- 150000002989 phenols Chemical class 0.000 title description 16
- 238000000034 method Methods 0.000 title description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000011269 tar Substances 0.000 description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002641 tar oil Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005292 vacuum distillation 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
- C07C37/005—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from products, waste products or side-products of processes, not directed to the production of phenols, by conversion or working-up
Definitions
- the above mentioned objection is removed by adding to the extraction media hitherto employed tar bases viz., bases of coke-plant tar or of low-temperature distillation tar, such as pyridine, quinoline or their homologues, the
- Example I 500 cubic centimetres of an ammoniacal liquor which as before contains 3.19 grams of phenols per litre is washed three times, each time with. 100 cubic centimetres of bases, which have been obtained from tar oil having a boiling point of from240 C. to 320 C.
- the phenols could be iron I ing treating the said liquors with tar bases.
- a process for obtaining phenols from phenol-bearing industrial liquors comprising treating said liquors with bases from coke-plant tar.
- a process for obtaining phenols from phenol bearing industrial liquors comprising treating said liquors with tar oils from which the phenols have been removed but which still contain bases.
- a process for obtaining phenols from phenol bearing industrial liquors comprising treating the said liquors with a mixture of aromatic hydrocarbons and tar bases.
- a process for obtaining phenols from phenol-bearing industrial liquors comprising treating the said liquors with a mixture of aromatic hydrocarbons and bases from coke plant tar.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Mar. 10, 1931 UNITED STATES P E To Flca IRI'rz ULRIcn, or KARNAZP, NEAR ESSEN-RUHR, GERMANY, AssIeNo ro zEcRE MATHIAS STINNES, or nssE JwnR, GERMANY PROCESS FOR OBTAINING PHENOLS FROM runner-BE RIN INDUSTRIAL LIoUoRs No Drawing. Application filed February 25, 1926, Serial No. 90,684, and in Germany March-13, 1925.
According to the processes hitherto known the washing of phenol-bearing industrial liquors including ammoniacal liquor for the purpose of removing phenol therefrom is efi'ected exclusively by means of benzene or its homologues. This process has the great disadvantage that it does not make it possible to obtain the Whole of the phenols of the ammoniacal liquor and in particular the valuable water-soluble carbolic acid. Many experiments carried out on the basis of this process have yielded the result that on an average only about per cent of the phenols present in the ammoniacal liquor can be recovered economically, while the remaining 35 per cent consisting mainly of carbolic acid is to be abandoned.
According to the present invention the above mentioned objection is removed by adding to the extraction media hitherto employed tar bases viz., bases of coke-plant tar or of low-temperature distillation tar, such as pyridine, quinoline or their homologues, the
boiling point of which is preferably so high that the solubility in water of this class of substances is no longer in evidence. The greater cleansing action which is obtained with such a basic gas-washing oil, readily admits of being explained by the chemical affinity of the bases for the acid phenols. Accordingly the actual washing action in this process is to be attributed to the bases themselves, while benzene and its homologues are to be regarded as solvents or diluents for these substances and may therefore be replaced by petrol or other neutral oils.
Comparative experiments based on the processes hitherto usual and the process forming the subject matter of the present inven tion have given the following results:
Example I centimeters of a washing medium consisting of. 90degree benzene and 10 per cent. bases (boiling point from 200 to 250 0.). The yield of phenolamounts in this case to 82 per cent of the whole quantity of phenols in the ammonical liquor; Theincreased yield of phenol as compared withexperiment (a) Example [I 2 litres of the same ammoniacal liquor are. washed twice with a 20 per cent. quantity (that is, 2 400 cubic centimetres) of washing oil consisting of 90-degree benzene with 20 per cent. of bases boiling at 230 O. From the liquor so treated no perceptible quantities of phenols can be obtained by subsequent extraction with ether. The yield is therefore to be regarded as practically quantitative.
In the'case of a similarly arranged experiment with 90-degree benzene as washing medium, only a yield of about 65 per cent could be obtained. I
E wamplc I l I 500 cubic centimetres of a crude ammoniacal liquor with 3.19 grams of phenols per litre are washed three times with 200 cubic centimetres of a tar, oil from which phenol has been removed and which has a boiling point of from 200 to 250 C. in which 4 per cent of bases as such are contained, which here come into action in a free state. In this way 82 per cent of the phenols could be recovered.
Example I V 500 cubic centimetres of an ammoniacal liquor which as before contains 3.19 grams of phenols per litre is washed three times, each time with. 100 cubic centimetres of bases, which have been obtained from tar oil having a boiling point of from240 C. to 320 C.
About 7 5 per cent of, the phenols could be iron I ing treating the said liquors with tar bases.
2. A process for obtaining phenols from phenol-bearing industrial liquors, comprising treating said liquors with bases from coke-plant tar.
3. A process for obtaining phenols from phenol bearing industrial liquors, comprising treating said liquors with tar oils from which the phenols have been removed but which still contain bases.
4. A process for obtaining phenols from phenol bearing industrial liquors, comprising treating the said liquors with a mixture of aromatic hydrocarbons and tar bases.
5. A process for obtaining phenols from phenol-bearing industrial liquors, comprising treating the said liquors with a mixture of aromatic hydrocarbons and bases from coke plant tar.
In testimony whereof I afiiX my signature.
DooroR FRITZ ULRICH.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1795382X | 1925-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1795382A true US1795382A (en) | 1931-03-10 |
Family
ID=7743638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US90684A Expired - Lifetime US1795382A (en) | 1925-03-13 | 1926-02-25 | Process for obtaining phenols from phenol-bearing industrial liquors |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1795382A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2432062A (en) * | 1943-07-05 | 1947-12-02 | Reilly Tar & Chem Corp | Separation of metacresol from paracresol |
| US2432064A (en) * | 1943-10-20 | 1947-12-02 | Reilly Tar & Chem Corp | Purification of quinaldine |
| US2432065A (en) * | 1943-10-29 | 1947-12-02 | Reilly Tar & Chem Corp | Purification of isoquinoline |
| US2526807A (en) * | 1945-08-20 | 1950-10-24 | Francis E Cislak | Process for separating 1, 3, 4-xylenol and 1, 4, 2-xylenol from mixtures containing the same and organic base complexes derived therefrom |
| US2808375A (en) * | 1954-05-10 | 1957-10-01 | Jones & Laughlin Steel Corp | Phenol removal from phenol-contaminated waste waters |
| US2812305A (en) * | 1954-08-25 | 1957-11-05 | Jones & Laughlin Steel Corp | Phenol removal from phenol-bearing waters |
| US2829175A (en) * | 1953-10-14 | 1958-04-01 | Gulf Research Development Co | Purification of bis-phenols |
-
1926
- 1926-02-25 US US90684A patent/US1795382A/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2432062A (en) * | 1943-07-05 | 1947-12-02 | Reilly Tar & Chem Corp | Separation of metacresol from paracresol |
| US2432064A (en) * | 1943-10-20 | 1947-12-02 | Reilly Tar & Chem Corp | Purification of quinaldine |
| US2432065A (en) * | 1943-10-29 | 1947-12-02 | Reilly Tar & Chem Corp | Purification of isoquinoline |
| US2526807A (en) * | 1945-08-20 | 1950-10-24 | Francis E Cislak | Process for separating 1, 3, 4-xylenol and 1, 4, 2-xylenol from mixtures containing the same and organic base complexes derived therefrom |
| US2829175A (en) * | 1953-10-14 | 1958-04-01 | Gulf Research Development Co | Purification of bis-phenols |
| US2808375A (en) * | 1954-05-10 | 1957-10-01 | Jones & Laughlin Steel Corp | Phenol removal from phenol-contaminated waste waters |
| US2812305A (en) * | 1954-08-25 | 1957-11-05 | Jones & Laughlin Steel Corp | Phenol removal from phenol-bearing waters |
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