GB1076031A - Improvments in or relating to the reaction between conjugated diolefines and phenols - Google Patents
Improvments in or relating to the reaction between conjugated diolefines and phenolsInfo
- Publication number
- GB1076031A GB1076031A GB17142/64A GB1714264A GB1076031A GB 1076031 A GB1076031 A GB 1076031A GB 17142/64 A GB17142/64 A GB 17142/64A GB 1714264 A GB1714264 A GB 1714264A GB 1076031 A GB1076031 A GB 1076031A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkylated
- acid
- cyclopentadiene
- phenol
- lambda
- 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 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 2
- 230000003197 catalytic effect Effects 0.000 abstract 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 abstract 2
- 238000010494 dissociation reaction Methods 0.000 abstract 2
- 230000005593 dissociations Effects 0.000 abstract 2
- -1 hydroxy aromatic compounds Chemical class 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002015 acyclic group Chemical group 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000004292 cyclic ethers Chemical class 0.000 abstract 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C37/14—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 addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- 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
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for preparing hydroxy aromatic compounds which carry unsaturated side groups comprises reacting together at least one monohydric phenol having no substituents which contain atoms other than carbon and hydrogen and having at least one unsubstituted position ortho or para to the hydroxy group and a conjugated acyclic or cyclic diene having at least 5 carbon atoms in the presence of a catalytic quantity of an acid having a first dissociation constant, K25 DEG c., greater than 7 x 10-2 or phosphoric acid, and a quantity of water which is at least twice the weight of the anhydrous acid present and at least 1% by weight of the phenol to be reacted. In a modification of the process a catalytic amount of a weak acid, other than phosphoric or hydrofluoric acid, having a dissociation constant K25 DEG c. of less than 7 x 10-2 is employed. In examples: phenol is alkylated with liquid and gaseous cyclopentadiene, p-cresol is alkylated with cyclopentadiene, lambda-nonylphenol is alkylated with cyclopentadiene, b -naphthol is alkylated with cyclopentadiene, lambda-cresol is alkylated with cyclo-hexadiene and phenol is alkylated with piperylene. Catalysts specified in examples include lambda-toluene sulphonic acid and sulphuric acid. The production of cyclic ethers as by-products is mentioned.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17142/64A GB1076031A (en) | 1964-04-24 | 1964-04-24 | Improvments in or relating to the reaction between conjugated diolefines and phenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17142/64A GB1076031A (en) | 1964-04-24 | 1964-04-24 | Improvments in or relating to the reaction between conjugated diolefines and phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1076031A true GB1076031A (en) | 1967-07-19 |
Family
ID=10090021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17142/64A Expired GB1076031A (en) | 1964-04-24 | 1964-04-24 | Improvments in or relating to the reaction between conjugated diolefines and phenols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1076031A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932537A (en) * | 1971-09-09 | 1976-01-13 | Reichhold Chemicals, Inc. | Alkylation of phenols |
| EP0148817A4 (en) * | 1983-06-27 | 1985-11-21 | Dow Chemical Co | Phenolic hydroxyl-containing compositions and epoxy resins prepared therefrom and solid compositions prepared therefrom. |
-
1964
- 1964-04-24 GB GB17142/64A patent/GB1076031A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932537A (en) * | 1971-09-09 | 1976-01-13 | Reichhold Chemicals, Inc. | Alkylation of phenols |
| EP0148817A4 (en) * | 1983-06-27 | 1985-11-21 | Dow Chemical Co | Phenolic hydroxyl-containing compositions and epoxy resins prepared therefrom and solid compositions prepared therefrom. |
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