GB885044A - A process for the production of carvomenthene oxide - Google Patents
A process for the production of carvomenthene oxideInfo
- Publication number
- GB885044A GB885044A GB16508/59A GB1650859A GB885044A GB 885044 A GB885044 A GB 885044A GB 16508/59 A GB16508/59 A GB 16508/59A GB 1650859 A GB1650859 A GB 1650859A GB 885044 A GB885044 A GB 885044A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxide
- carvomenthene
- catalyst
- hydrogen
- platinum
- 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
- WSHVHJSDSVPPIV-UHFFFAOYSA-N 6-methyl-3-propan-2-yl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C(C)C)CCC2(C)OC21 WSHVHJSDSVPPIV-UHFFFAOYSA-N 0.000 title abstract 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 6
- 239000003054 catalyst Substances 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- CCEFMUBVSUDRLG-UHFFFAOYSA-N limonene-1,2-epoxide Chemical compound C1C(C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-UHFFFAOYSA-N 0.000 abstract 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 229910052697 platinum Inorganic materials 0.000 abstract 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000003822 epoxy resin Substances 0.000 abstract 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 abstract 2
- 229920000647 polyepoxide Polymers 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 abstract 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- -1 aliphatic peracids Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 229940106691 bisphenol a Drugs 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 229940087305 limonene Drugs 0.000 abstract 1
- 235000001510 limonene Nutrition 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 abstract 1
- 229910003446 platinum oxide Inorganic materials 0.000 abstract 1
- 229920000768 polyamine Polymers 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 150000007519 polyprotic acids Polymers 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000012262 resinous product Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/145—Compounds containing one epoxy group
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A cured epoxy resinous product is prepared by mixing together an epoxy resin, carvomenthene oxide (which has been prepared by reacting limonene monoxide with hydrogen in the presence of a finely divided platinum-containing catalyst) and a curing agent, allowing the compounds to react on each other and then heating to complete the curing. Suitable curing agents are polyamines, polybasic acids or anhydrides. In an example, carvomenthene oxide is dissolved in a condensation polymer of epichlorohydrin and bisphenol-A and the solution is mixed with diethylene triamine, kept at 23 DEG to 27 DEG C. for 20 hours then heated for 2 hours at 100 DEG C. to form a cured product.ALSO:The invention comprises carvomenthene oxide which may be produced by reacting limonene monoxide with hydrogen in the presence of a finely divided platinum-containing catalyst until 1 mole of hydrogen has been reacted per mole of limonene monoxide. The hydrogenation may be conducted at 25 DEG C. to 45 DEG C. at a hydrogen pressure of 1 to 15 atmospheres, in the presence or absence of an inert organic solvent, such as methanol, ethanol or isopropanol. The catalyst may be platinum or platinum oxide and may be deposited on a carrier such as calcium carbonate or aluminium oxide. The reaction may be conducted by passing the reaction mixture through a fixed bed of catalyst or by employing a fluidised dispersion of the catalyst in the reaction mixture. Carvomenthene oxide is useful as a reactive diluent for epoxy resins (see Group IV(a)). The limonene monoxide may be produced by reaction of limonene with peracetic or other aliphatic peracids or perbenzoic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US885044XA | 1958-05-19 | 1958-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB885044A true GB885044A (en) | 1961-12-20 |
Family
ID=22211756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16508/59A Expired GB885044A (en) | 1958-05-19 | 1959-05-14 | A process for the production of carvomenthene oxide |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB885044A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4352937A (en) * | 1976-08-09 | 1982-10-05 | Shell Oil Company | Cyclohexane derivatives |
| US4582915A (en) * | 1983-10-11 | 1986-04-15 | Merck & Co., Inc. | Process for C-methylation of 2-methylbutyrates |
| US4584389A (en) * | 1983-10-11 | 1986-04-22 | Merck & Co., Inc. | Processes for preparing 6(R)-[2-[8(S)(2,2-dimethylbutyryloxy)-2(S),6(S)-dimethyl-1,2,3,4,4a(S),5,6,7,8,8a(S)-decahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one |
| EP0137444A3 (en) * | 1983-10-11 | 1988-03-02 | Merck & Co. Inc. | Processes for preparing 6(r)-û2-û8(s)(2,2-dimethylbutyryloxy)-2(s),6(s)-dimethyl-1,2,3,4,4a(s),5,6,7,8,8a(s)-decahydronaphthyl-1(s)¨ethyl¨-4(r)-hydroxy-3,4,5,6-tetrahydro-2h-pyran-2-one |
-
1959
- 1959-05-14 GB GB16508/59A patent/GB885044A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4352937A (en) * | 1976-08-09 | 1982-10-05 | Shell Oil Company | Cyclohexane derivatives |
| US4582915A (en) * | 1983-10-11 | 1986-04-15 | Merck & Co., Inc. | Process for C-methylation of 2-methylbutyrates |
| US4584389A (en) * | 1983-10-11 | 1986-04-22 | Merck & Co., Inc. | Processes for preparing 6(R)-[2-[8(S)(2,2-dimethylbutyryloxy)-2(S),6(S)-dimethyl-1,2,3,4,4a(S),5,6,7,8,8a(S)-decahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one |
| EP0137444A3 (en) * | 1983-10-11 | 1988-03-02 | Merck & Co. Inc. | Processes for preparing 6(r)-û2-û8(s)(2,2-dimethylbutyryloxy)-2(s),6(s)-dimethyl-1,2,3,4,4a(s),5,6,7,8,8a(s)-decahydronaphthyl-1(s)¨ethyl¨-4(r)-hydroxy-3,4,5,6-tetrahydro-2h-pyran-2-one |
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