DE2434966A1 - O,o,o',o'-tetraalkylsubstituierte biscyclohexanole - Google Patents
O,o,o',o'-tetraalkylsubstituierte biscyclohexanoleInfo
- Publication number
- DE2434966A1 DE2434966A1 DE19742434966 DE2434966A DE2434966A1 DE 2434966 A1 DE2434966 A1 DE 2434966A1 DE 19742434966 DE19742434966 DE 19742434966 DE 2434966 A DE2434966 A DE 2434966A DE 2434966 A1 DE2434966 A1 DE 2434966A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- dimethyl
- hydroxycyclohexyl
- carbon atoms
- biscyclohexanols
- 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.)
- Pending
Links
- 229910052760 oxygen Inorganic materials 0.000 title description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 4
- 229930185605 Bisphenol Natural products 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 239000001294 propane Substances 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- -1 1,1 -Bis- (3,5-dimethyl-4-hydroxycyclohexyl) cyclododecane Chemical compound 0.000 description 3
- 229910018182 Al—Cu Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- OFJIEHQLVVQAQF-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylcyclohexyl)methyl]-2,6-dimethylcyclohexan-1-ol Chemical compound C1C(C)C(O)C(C)CC1CC1CC(C)C(O)C(C)C1 OFJIEHQLVVQAQF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229920006305 unsaturated polyester Polymers 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZZWZMUXHALBCQ-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CC=2C=C(C)C(O)=C(C)C=2)=C1 AZZWZMUXHALBCQ-UHFFFAOYSA-N 0.000 description 1
- BWCAVNWKMVHLFW-UHFFFAOYSA-N 4-[1-(4-hydroxy-3,5-dimethylphenyl)cyclohexyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C2(CCCCC2)C=2C=C(C)C(O)=C(C)C=2)=C1 BWCAVNWKMVHLFW-UHFFFAOYSA-N 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- OBZFGWBLZXIBII-UHFFFAOYSA-N 4-[3-(4-hydroxy-3,5-dimethylphenyl)-3-methylbutyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CCC(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 OBZFGWBLZXIBII-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WBMCEBIKKIXVGW-UHFFFAOYSA-N CC1CC(CC(C1O)C)C(CC)C1CC(C(C(C1)C)O)C Chemical compound CC1CC(CC(C1O)C)C(CC)C1CC(C(C(C1)C)O)C WBMCEBIKKIXVGW-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- PCWSNKLABDQTKE-UHFFFAOYSA-N [Ni+2].[O-][Cr]([O-])=O Chemical compound [Ni+2].[O-][Cr]([O-])=O PCWSNKLABDQTKE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
- C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyesters Or Polycarbonates (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742434966 DE2434966A1 (de) | 1974-07-19 | 1974-07-19 | O,o,o',o'-tetraalkylsubstituierte biscyclohexanole |
| NL7508519A NL7508519A (nl) | 1974-07-19 | 1975-07-16 | Werkwijze voor het bereiden van gesubstitueerde biscyclohexanolen. |
| JP8674475A JPS5134133A (ja) | 1974-07-19 | 1975-07-17 | Chikanbisushikurohekisanooruno seizohohoho |
| ES439537A ES439537A1 (es) | 1974-07-19 | 1975-07-17 | Procedimiento para preparar bisciclohexanoles. |
| BE158376A BE831458A (fr) | 1974-07-19 | 1975-07-17 | Bis-cyclohexanols 0,0,0',0'-tetralcoyl-substitues |
| AT554075A ATA554075A (de) | 1974-07-19 | 1975-07-17 | Verfahren zur herstellung von biscyclohexanolen |
| GB3023775A GB1458657A (en) | 1974-07-19 | 1975-07-18 | Substituted biscyclohexanols |
| FR7522570A FR2278665A1 (fr) | 1974-07-19 | 1975-07-18 | Bis-cyclohexanols o,o,o',o'-tetralcoyl-substitues et leur utilisation notamment pour la fabrication de masses de polyesters durcissables |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742434966 DE2434966A1 (de) | 1974-07-19 | 1974-07-19 | O,o,o',o'-tetraalkylsubstituierte biscyclohexanole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2434966A1 true DE2434966A1 (de) | 1976-02-05 |
Family
ID=5921072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742434966 Pending DE2434966A1 (de) | 1974-07-19 | 1974-07-19 | O,o,o',o'-tetraalkylsubstituierte biscyclohexanole |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5134133A (https=) |
| AT (1) | ATA554075A (https=) |
| BE (1) | BE831458A (https=) |
| DE (1) | DE2434966A1 (https=) |
| ES (1) | ES439537A1 (https=) |
| FR (1) | FR2278665A1 (https=) |
| GB (1) | GB1458657A (https=) |
| NL (1) | NL7508519A (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0368604A3 (en) * | 1988-11-09 | 1991-04-17 | Chisso Corporation | New diamino and dinitro compounds and a process for preparing the diamino compounds |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH072659B2 (ja) * | 1986-05-29 | 1995-01-18 | 三井石油化学工業株式会社 | 新規なビスシクロヘキサノール類 |
| JPH072660B2 (ja) * | 1986-05-29 | 1995-01-18 | 三井石油化学工業株式会社 | 新規なビスシクロヘキサノール類 |
-
1974
- 1974-07-19 DE DE19742434966 patent/DE2434966A1/de active Pending
-
1975
- 1975-07-16 NL NL7508519A patent/NL7508519A/xx unknown
- 1975-07-17 AT AT554075A patent/ATA554075A/de not_active Application Discontinuation
- 1975-07-17 JP JP8674475A patent/JPS5134133A/ja active Pending
- 1975-07-17 ES ES439537A patent/ES439537A1/es not_active Expired
- 1975-07-17 BE BE158376A patent/BE831458A/xx unknown
- 1975-07-18 GB GB3023775A patent/GB1458657A/en not_active Expired
- 1975-07-18 FR FR7522570A patent/FR2278665A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0368604A3 (en) * | 1988-11-09 | 1991-04-17 | Chisso Corporation | New diamino and dinitro compounds and a process for preparing the diamino compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7508519A (nl) | 1976-01-21 |
| BE831458A (fr) | 1976-01-19 |
| JPS5134133A (ja) | 1976-03-23 |
| GB1458657A (en) | 1976-12-15 |
| FR2278665A1 (fr) | 1976-02-13 |
| ES439537A1 (es) | 1977-02-16 |
| FR2278665B1 (https=) | 1979-05-11 |
| ATA554075A (de) | 1977-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |