CH628878A5 - Process for the preparation of 2-cyanohexanoic acid derivatives - Google Patents
Process for the preparation of 2-cyanohexanoic acid derivatives Download PDFInfo
- Publication number
- CH628878A5 CH628878A5 CH825077A CH825077A CH628878A5 CH 628878 A5 CH628878 A5 CH 628878A5 CH 825077 A CH825077 A CH 825077A CH 825077 A CH825077 A CH 825077A CH 628878 A5 CH628878 A5 CH 628878A5
- Authority
- CH
- Switzerland
- Prior art keywords
- general formula
- acid
- preparation
- acid derivatives
- chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 15
- CYYDDSNDKQYALZ-UHFFFAOYSA-N 2-cyanohexanoic acid Chemical class CCCCC(C#N)C(O)=O CYYDDSNDKQYALZ-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- -1 2,2-dichlorovinyl Chemical group 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 244000028419 Styrax benzoin Species 0.000 description 4
- 235000000126 Styrax benzoin Nutrition 0.000 description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 description 4
- 229960002130 benzoin Drugs 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 235000019382 gum benzoic Nutrition 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- IVUPBSLRQYWNKZ-UHFFFAOYSA-N 4,6,6,6-tetrachloro-2-cyano-3,3-dimethylhexanoic acid Chemical compound N#CC(C(O)=O)C(C)(C)C(Cl)CC(Cl)(Cl)Cl IVUPBSLRQYWNKZ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- HDITUCONWLWUJR-UHFFFAOYSA-N diethylazanium;chloride Chemical compound [Cl-].CC[NH2+]CC HDITUCONWLWUJR-UHFFFAOYSA-N 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- KGUVNWFNGFCCKR-UHFFFAOYSA-N 2-cyano-3,3-dimethylpent-4-enoic acid Chemical compound C=CC(C)(C)C(C#N)C(O)=O KGUVNWFNGFCCKR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000251730 Chondrichthyes Species 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002505 iron Chemical class 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 125000005609 naphthenate group Chemical group 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SMGYWFUKXCEIPC-UHFFFAOYSA-N n,n-diethylpropan-1-amine;hydrochloride Chemical compound Cl.CCCN(CC)CC SMGYWFUKXCEIPC-UHFFFAOYSA-N 0.000 description 1
- IUSOXUFUXZORBF-UHFFFAOYSA-N n,n-dioctyloctan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCC[NH+](CCCCCCCC)CCCCCCCC IUSOXUFUXZORBF-UHFFFAOYSA-N 0.000 description 1
- YCGYSDWVARRPFG-UHFFFAOYSA-N n-butylbutan-1-amine;hydrobromide Chemical compound [Br-].CCCC[NH2+]CCCC YCGYSDWVARRPFG-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| GB2826276A GB1580204A (en) | 1976-07-07 | 1976-07-07 | 2-cyanohexanoic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH628878A5 true CH628878A5 (en) | 1982-03-31 |
Family
ID=10272872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH825077A CH628878A5 (en) | 1976-07-07 | 1977-07-05 | Process for the preparation of 2-cyanohexanoic acid derivatives |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS537622A (Direct) |
| BE (1) | BE856490A (Direct) |
| BR (1) | BR7704406A (Direct) |
| CA (1) | CA1094103A (Direct) |
| CH (1) | CH628878A5 (Direct) |
| DE (1) | DE2730359A1 (Direct) |
| DK (1) | DK159265C (Direct) |
| FR (1) | FR2357534A1 (Direct) |
| GB (1) | GB1580204A (Direct) |
| IT (1) | IT1081510B (Direct) |
| MX (1) | MX4912E (Direct) |
| NL (1) | NL7707416A (Direct) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1115730A (en) * | 1978-02-20 | 1982-01-05 | Roger A. Sheldon | Preparation of 2-cyanohexanoic acid derivatives and the derivatives prepared by the process |
| JP4958428B2 (ja) * | 2005-11-25 | 2012-06-20 | Ｆｄｋエナジー株式会社 | アルカリ乾電池 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN142702B (Direct) * | 1974-09-10 | 1977-08-20 | Sagami Chem Res | |
| JPS5159839A (ja) * | 1974-10-23 | 1976-05-25 | Sankyo Co | Shikuropuropankarubonsanjudotaino seizoho |
| LU73349A1 (Direct) * | 1975-09-08 | 1976-04-13 |
-
1976
- 1976-07-07 GB GB2826276A patent/GB1580204A/en not_active Expired
-
1977
- 1977-05-19 CA CA278,776A patent/CA1094103A/en not_active Expired
- 1977-07-05 DE DE19772730359 patent/DE2730359A1/de not_active Withdrawn
- 1977-07-05 BR BR7704406A patent/BR7704406A/pt unknown
- 1977-07-05 IT IT2541077A patent/IT1081510B/it active
- 1977-07-05 JP JP7957777A patent/JPS537622A/ja active Granted
- 1977-07-05 NL NL7707416A patent/NL7707416A/xx not_active Application Discontinuation
- 1977-07-05 BE BE179092A patent/BE856490A/xx not_active IP Right Cessation
- 1977-07-05 MX MX587477U patent/MX4912E/es unknown
- 1977-07-05 FR FR7720605A patent/FR2357534A1/fr active Granted
- 1977-07-05 CH CH825077A patent/CH628878A5/de not_active IP Right Cessation
- 1977-07-05 DK DK302577A patent/DK159265C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE856490A (fr) | 1978-01-05 |
| JPS616814B2 (Direct) | 1986-03-01 |
| DK302577A (da) | 1978-01-08 |
| GB1580204A (en) | 1980-11-26 |
| MX4912E (es) | 1983-01-03 |
| NL7707416A (nl) | 1978-01-10 |
| DE2730359A1 (de) | 1978-01-12 |
| FR2357534B1 (Direct) | 1978-11-03 |
| CA1094103A (en) | 1981-01-20 |
| JPS537622A (en) | 1978-01-24 |
| DK159265C (da) | 1991-02-18 |
| IT1081510B (it) | 1985-05-21 |
| FR2357534A1 (fr) | 1978-02-03 |
| DK159265B (da) | 1990-09-24 |
| BR7704406A (pt) | 1978-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |