Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Octane | HCID 356 | — |
| Reactant | Acrylic Acid | HCID 6581 | — |
| Reactant | 1,3-Adamantanediol | HCID 573829 | — |
| Reactant | Sodium | HCID 5360545 | — |
| Catalyst | Sulfuric Acid | HCID 1118 | — |
| Catalyst | 4-Methoxyphenol | HCID 9015 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 1-ADAMANTYL ACRYLATE | HCID 11390128 | 79.2% |
Reaction Steps
Adamantyl acrylate is synthesized by the method described in JP-2001-106650-A. That is, 86.4 g (513 mmol) of 1,3-adamantane diol containing sodium in an amount of 0.05% by weight, 400 ml of toluene, 400 ml of n-octane, 108 g (1,500 mmol) of acrylic acid, 1.23 g of strong sulfuric acid, and 0.37 g p-methoxyphenol are placed in a separable flask equipped with a stirrer, a thermometer, a Dean-Stark water separator, a Dimroth condenser, an air introduction tube, and a separating valve provided on the bottom side. Reaction is conducted for five hours in a reflux state at 112° C. while inspiring a small amount of air to the flask. During the reaction, produced water is removed by using the Dean-Stark water separator. The reaction liquid is cooled down to room temperature followed by filtration of insoluble matters. 840 g of 5% by weight sodium hydroxide solution is admixed and separated. Thereafter, the organic phase is washed with 400 ml of water six times. The organic phase is condensed with a reduced pressure, filtered, and dried to obtain 83.8 g of adamantyl acrylate of white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08617778B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-eac53207ef6344e0bfeab26cca3dc5c0 |
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| Source note | uspto-grants-2013_12 |
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