DE3325983C2 - - Google Patents
Info
- Publication number
- DE3325983C2 DE3325983C2 DE3325983A DE3325983A DE3325983C2 DE 3325983 C2 DE3325983 C2 DE 3325983C2 DE 3325983 A DE3325983 A DE 3325983A DE 3325983 A DE3325983 A DE 3325983A DE 3325983 C2 DE3325983 C2 DE 3325983C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- tricyclo
- reaction
- decane
- yield
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 17
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 11
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- ZKDKHHRIOHJUSY-UHFFFAOYSA-N decan-3-yl formate Chemical compound CCCCCCCC(CC)OC=O ZKDKHHRIOHJUSY-UHFFFAOYSA-N 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- JBXYCUKPDAAYAS-UHFFFAOYSA-N methanol;trifluoroborane Chemical compound OC.FB(F)F JBXYCUKPDAAYAS-UHFFFAOYSA-N 0.000 claims description 2
- LKWKIVHUCKVYOA-UHFFFAOYSA-N phosphoric acid;trifluoroborane Chemical compound FB(F)F.OP(O)(O)=O LKWKIVHUCKVYOA-UHFFFAOYSA-N 0.000 claims description 2
- MVJKXJPDBTXECY-UHFFFAOYSA-N trifluoroborane;hydrate Chemical compound O.FB(F)F MVJKXJPDBTXECY-UHFFFAOYSA-N 0.000 claims description 2
- 230000006315 carbonylation Effects 0.000 claims 1
- 238000005810 carbonylation reaction Methods 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 25
- 235000019253 formic acid Nutrition 0.000 description 17
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- SAOSCTYRONNFTC-UHFFFAOYSA-N 2-methyl-decanoic acid Chemical compound CCCCCCCCC(C)C(O)=O SAOSCTYRONNFTC-UHFFFAOYSA-N 0.000 description 7
- -1 formyloxy group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- FKZJBAXKHJIQDU-UHFFFAOYSA-N perhydro-4,7-methanoinden-5-ol Chemical compound C12CCCC2C2CC(O)C1C2 FKZJBAXKHJIQDU-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/12—Saturated polycyclic compounds
- C07C61/125—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system
- C07C61/135—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system having three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57128235A JPS5920245A (ja) | 1982-07-22 | 1982-07-22 | トリシクロ〔５．２．１．０↑２’↑６〕デカン−２−カルボン酸の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3325983A1 DE3325983A1 (de) | 1984-01-26 |
| DE3325983C2 true DE3325983C2 (en, 2012) | 1991-11-28 |
Family
ID=14979829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833325983 Granted DE3325983A1 (de) | 1982-07-22 | 1983-07-19 | Verfahren zur herstellung von tricyclo(5.2.1.0(pfeil hoch)2(pfeil hoch)(pfeil hoch),(pfeil hoch)(pfeil hoch)6(pfeil hoch))decan-2-carbonsaeure |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4602107A (en, 2012) |
| JP (1) | JPS5920245A (en, 2012) |
| CH (1) | CH654291A5 (en, 2012) |
| DE (1) | DE3325983A1 (en, 2012) |
| FR (1) | FR2530621B1 (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3729566A1 (de) * | 1987-09-04 | 1989-03-16 | Zipperling Kessler & Co | Intrinsisch leitfaehiges polymer in form eines dispergierbaren feststoffes, dessen herstellung und dessen verwendung |
| JP2680069B2 (ja) * | 1988-10-07 | 1997-11-19 | 三菱瓦斯化学株式会社 | トリシクロデカンカルボン酸エステルの製造法 |
| JPH073766Y2 (ja) * | 1989-09-05 | 1995-01-30 | 株式会社安田製作所 | 延線車 |
| JPH0652410U (ja) * | 1992-12-24 | 1994-07-19 | セイレイ工業株式会社 | 芝刈機の刈芝収容部構造 |
| JP4725136B2 (ja) * | 2005-03-10 | 2011-07-13 | 三菱瓦斯化学株式会社 | トリシクロ［５．２．１．０２，６］デカン−２−カルボン酸エステルの製造法 |
| JP4725137B2 (ja) * | 2005-03-10 | 2011-07-13 | 三菱瓦斯化学株式会社 | エキソ−トリシクロ［５．２．１．０２，６］デカン−エンド−２−カルボン酸の製造方法 |
| US11225453B2 (en) | 2018-02-16 | 2022-01-18 | Mitsubishi Gas Chemical Company, Inc. | Method for producing tricyclo[5.2.1.02,6]decane-2-carboxylate |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6049169B2 (ja) * | 1978-04-28 | 1985-10-31 | 花王株式会社 | ８−エキソ−ヒドロキシメチル−エンド−トリシクロ〔５．２．１．０↑２，↑６〕デカンエステルおよびエ−テル |
| US4411828A (en) * | 1980-03-14 | 1983-10-25 | Kao Corporation | Fragrant tricyclic carboxylates |
| CH654204A5 (it) * | 1980-03-14 | 1986-02-14 | Kao Corp | Composizioni di profumo e procedimento per la loro preparazione. |
-
1982
- 1982-07-22 JP JP57128235A patent/JPS5920245A/ja active Granted
-
1983
- 1983-07-18 US US06/515,022 patent/US4602107A/en not_active Expired - Lifetime
- 1983-07-19 DE DE19833325983 patent/DE3325983A1/de active Granted
- 1983-07-20 CH CH3977/83A patent/CH654291A5/de not_active IP Right Cessation
- 1983-07-22 FR FR8312135A patent/FR2530621B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH654291A5 (de) | 1986-02-14 |
| FR2530621A1 (fr) | 1984-01-27 |
| JPS5920245A (ja) | 1984-02-01 |
| US4602107A (en) | 1986-07-22 |
| JPS6140658B2 (en, 2012) | 1986-09-10 |
| DE3325983A1 (de) | 1984-01-26 |
| FR2530621B1 (fr) | 1986-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |