GB443113A - Improvements in or relating to the manufacture of phenols - Google Patents
Improvements in or relating to the manufacture of phenolsInfo
- Publication number
- GB443113A GB443113A GB2402134A GB2402134A GB443113A GB 443113 A GB443113 A GB 443113A GB 2402134 A GB2402134 A GB 2402134A GB 2402134 A GB2402134 A GB 2402134A GB 443113 A GB443113 A GB 443113A
- Authority
- GB
- United Kingdom
- Prior art keywords
- solution
- benzene
- chlorobenzene
- iso
- hydroxy
- 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
- 150000002989 phenols Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 6
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- DMRKWIRDXBHDBB-UHFFFAOYSA-N 2-but-1-enyl-4-chlorophenol Chemical compound ClC1=CC(=C(C=C1)O)C=CCC DMRKWIRDXBHDBB-UHFFFAOYSA-N 0.000 abstract 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkene compound Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 239000003208 petroleum Substances 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- WNQCXLRQIZKWMD-UHFFFAOYSA-N 2,3-dichloro-4-(3-methylbut-1-enyl)phenol Chemical compound ClC=1C(=C(C=CC1C=CC(C)C)O)Cl WNQCXLRQIZKWMD-UHFFFAOYSA-N 0.000 abstract 1
- GFQXMONTDVLZTO-UHFFFAOYSA-N 2-chloro-4-(3-chlorophenyl)hept-3-en-3-ol Chemical compound C(CC)C(=C(C(C)Cl)O)C1=CC=CC(=C1)Cl GFQXMONTDVLZTO-UHFFFAOYSA-N 0.000 abstract 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 abstract 1
- RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 abstract 1
- GLXDMSOEJKXENG-UHFFFAOYSA-N 4-chloro-2-propylphenol Chemical compound CCCC1=CC(Cl)=CC=C1O GLXDMSOEJKXENG-UHFFFAOYSA-N 0.000 abstract 1
- JUZOIPVKEQIOSJ-UHFFFAOYSA-N BrCCC=CC1=C(C=CC=C1)O Chemical compound BrCCC=CC1=C(C=CC=C1)O JUZOIPVKEQIOSJ-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000012259 ether extract Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 abstract 1
- 229940031826 phenolate Drugs 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 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
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/18—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving halogen atoms of halogenated compounds
-
- 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
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Halogenalkylphenols are prepared by reacting a polyhalogenated alkene compound one halogen atom of which is attached to a doubly linked carbon atom and another halogen atom is attached to a saturated carbon atom which latter is in a -position to a doubly linked carbon atom with a phenolate in the presence of a non-dissociating organic diluent or by rearranging halogen alkenyl ethers of phenols by treatment in the presence of a high boiling organic solvent, preferably a tertiary amine such as dimethylaniline or quinoline. In examples: (1) a solution of potassium hydroxide and p - chlorphenol, 1 - methyl - 2 - hydroxy-5-chlorobenzene or 1-propyl-2-hydroxy-5-chlorobenzene in benzene is treated with 1.3-dichlorbutene-2 and yields, after extraction with petroleum ether, p-chlor-o-butenylphenol, 1-methyl or 1-propyl-2-hydroxy-3-chlorobutenyl-5-chlorobenzene; 3-chlorobutenylphenolether which may be recovered from the petroleum ether extract in example 1 or which may be obtained by the action of 1-3-dichlorobutene-2 upon p-chlorphenol in solution in acetone and in the presence of potassium carbonate is heated in solution in dimethylaniline to yield p-chlor-o-butenylphenol; (2) a solution of m-chlorophenol and potassium hydroxide in benzene is treated with 1.2.3-trichloro-iso-pentane (which forms 1.2-dichloro-iso-pentene-2 in the reaction mixture) to yield m-chloro-o-chloro-iso-pentenylphenol; (3) a solution of sodium phenolate in benzene (prepared by heating a solution of phenol in benzene with sodium) is treated with 1.3-dibromobutene to yield o-bromobutenylphenol. Specifications 389,514 and 428,295 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2402134A GB443113A (en) | 1934-08-20 | 1934-08-20 | Improvements in or relating to the manufacture of phenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2402134A GB443113A (en) | 1934-08-20 | 1934-08-20 | Improvements in or relating to the manufacture of phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB443113A true GB443113A (en) | 1936-02-20 |
Family
ID=10205110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2402134A Expired GB443113A (en) | 1934-08-20 | 1934-08-20 | Improvements in or relating to the manufacture of phenols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB443113A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2515335A (en) * | 1941-01-31 | 1950-07-18 | Bata Narodni Podnik | Method of condensing 1,3-dichlorobutene-2 with aromatic hydrocarbons |
| US4684752A (en) * | 1986-04-30 | 1987-08-04 | The Dow Chemical Company | Di-ortho-substituted di-meta-halogenated para-halomethylphenols |
-
1934
- 1934-08-20 GB GB2402134A patent/GB443113A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2515335A (en) * | 1941-01-31 | 1950-07-18 | Bata Narodni Podnik | Method of condensing 1,3-dichlorobutene-2 with aromatic hydrocarbons |
| US4684752A (en) * | 1986-04-30 | 1987-08-04 | The Dow Chemical Company | Di-ortho-substituted di-meta-halogenated para-halomethylphenols |
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