JP3388321B2 - シクロプロピルメチルケトンの製造方法 - Google Patents
シクロプロピルメチルケトンの製造方法Info
- Publication number
- JP3388321B2 JP3388321B2 JP33350292A JP33350292A JP3388321B2 JP 3388321 B2 JP3388321 B2 JP 3388321B2 JP 33350292 A JP33350292 A JP 33350292A JP 33350292 A JP33350292 A JP 33350292A JP 3388321 B2 JP3388321 B2 JP 3388321B2
- Authority
- JP
- Japan
- Prior art keywords
- iodide
- reaction
- solvent
- temperature
- butyrolactone
- 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
- HVCFCNAITDHQFX-UHFFFAOYSA-N 1-cyclopropylethanone Chemical compound CC(=O)C1CC1 HVCFCNAITDHQFX-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 38
- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 claims abstract description 13
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 31
- 238000009835 boiling Methods 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 6
- 238000010924 continuous production Methods 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 230000000717 retained effect Effects 0.000 claims description 3
- 238000006114 decarboxylation reaction Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 abstract description 3
- 150000004820 halides Chemical class 0.000 abstract description 2
- -1 phosphonium halide Chemical class 0.000 abstract description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000005309 metal halides Chemical class 0.000 abstract 1
- 230000000737 periodic effect Effects 0.000 abstract 1
- 230000007306 turnover Effects 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 description 16
- 150000002596 lactones Chemical class 0.000 description 15
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- 241000692885 Nymphalis antiopa Species 0.000 description 1
- 229910001619 alkaline earth metal iodide Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79453691A | 1991-11-19 | 1991-11-19 | |
| US794536 | 1991-11-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05262690A JPH05262690A (ja) | 1993-10-12 |
| JP3388321B2 true JP3388321B2 (ja) | 2003-03-17 |
Family
ID=25162925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP33350292A Expired - Lifetime JP3388321B2 (ja) | 1991-11-19 | 1992-11-19 | シクロプロピルメチルケトンの製造方法 |
Country Status (12)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19503241A1 (de) * | 1995-02-02 | 1996-08-08 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Cyclopropylalkylketonen und 4,5-Dihydroalkylfuranen |
| DE19630449A1 (de) * | 1996-07-27 | 1998-01-29 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Cyclopropylalkylketonen und 4,5-Dihydroalkylfuranen |
| DE19710879A1 (de) * | 1997-03-15 | 1998-09-17 | Huels Chemische Werke Ag | Verfahren zur Herstellung von hochreinem Cyclopropylmethylketon |
| CN105622369B (zh) * | 2015-12-29 | 2018-04-24 | 浙江联盛化学股份有限公司 | 一种环丙基甲基酮的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5811847B2 (ja) * | 1975-03-07 | 1983-03-04 | 武田薬品工業株式会社 | アシルシクロプロパンカゴウブツノ セイゾウホウ |
-
1992
- 1992-10-01 TW TW081107800A patent/TW210999B/zh not_active IP Right Cessation
- 1992-11-10 DK DK92810872.9T patent/DK0552586T3/da active
- 1992-11-10 EP EP92810872A patent/EP0552586B1/en not_active Expired - Lifetime
- 1992-11-10 ES ES92810872T patent/ES2078721T3/es not_active Expired - Lifetime
- 1992-11-10 DE DE69204983T patent/DE69204983T2/de not_active Expired - Lifetime
- 1992-11-10 AT AT92810872T patent/ATE128112T1/de active
- 1992-11-14 KR KR1019920021523A patent/KR100229128B1/ko not_active Expired - Lifetime
- 1992-11-17 IL IL10376592A patent/IL103765A/en not_active IP Right Cessation
- 1992-11-17 CA CA002083113A patent/CA2083113C/en not_active Expired - Lifetime
- 1992-11-19 MX MX9206664A patent/MX9206664A/es unknown
- 1992-11-19 JP JP33350292A patent/JP3388321B2/ja not_active Expired - Lifetime
-
1995
- 1995-09-21 GR GR950402524T patent/GR3017470T3/el unknown
Non-Patent Citations (1)
| Title |
|---|
| Ｍｏｒｉｏ ＡＳＡＯＫＡ ｅｔ ａｌ．，Ｃｈｅｍｉｓｔｒｙ Ｌｅｔｔｅｒｓ，１９７５，ｐ．１１４９−１１５２ |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0552586B1 (en) | 1995-09-20 |
| CA2083113C (en) | 2003-12-30 |
| JPH05262690A (ja) | 1993-10-12 |
| DK0552586T3 (da) | 1995-11-13 |
| EP0552586A1 (en) | 1993-07-28 |
| GR3017470T3 (en) | 1995-12-31 |
| DE69204983T2 (de) | 1996-03-14 |
| ATE128112T1 (de) | 1995-10-15 |
| CA2083113A1 (en) | 1993-05-20 |
| ES2078721T3 (es) | 1995-12-16 |
| IL103765A0 (en) | 1993-04-04 |
| IL103765A (en) | 1996-11-14 |
| MX9206664A (es) | 1993-05-01 |
| DE69204983D1 (de) | 1995-10-26 |
| TW210999B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-08-11 |
| KR100229128B1 (ko) | 1999-11-01 |
| KR930009974A (ko) | 1993-06-21 |
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