CN103044226B - Method for preparing cyclopentanone from adipic acid - Google Patents
Method for preparing cyclopentanone from adipic acid Download PDFInfo
- Publication number
- CN103044226B CN103044226B CN201210571398.5A CN201210571398A CN103044226B CN 103044226 B CN103044226 B CN 103044226B CN 201210571398 A CN201210571398 A CN 201210571398A CN 103044226 B CN103044226 B CN 103044226B
- Authority
- CN
- China
- Prior art keywords
- cyclopentanone
- composite catalyst
- reaction
- hexanodioic acid
- adipic acid
- 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.)
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- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 title claims abstract description 90
- 238000000034 method Methods 0.000 title claims abstract description 20
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title abstract 8
- 235000011037 adipic acid Nutrition 0.000 title abstract 4
- 239000001361 adipic acid Substances 0.000 title abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 150000002576 ketones Chemical class 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 239000002131 composite material Substances 0.000 claims abstract description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 229910021538 borax Inorganic materials 0.000 claims abstract description 6
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims abstract description 6
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 claims abstract description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims abstract description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims abstract description 6
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims abstract description 6
- 239000004328 sodium tetraborate Substances 0.000 claims abstract description 6
- 235000010339 sodium tetraborate Nutrition 0.000 claims abstract description 6
- 229910000018 strontium carbonate Inorganic materials 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 28
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 12
- 238000009833 condensation Methods 0.000 claims description 10
- 230000005494 condensation Effects 0.000 claims description 10
- 238000010792 warming Methods 0.000 claims description 10
- 239000001569 carbon dioxide Substances 0.000 claims description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 abstract 2
- 238000003763 carbonization Methods 0.000 abstract 1
- 230000005493 condensed matter Effects 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 4
- 238000007599 discharging Methods 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010257 thawing Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-HOSYLAQJSA-N cyclopentanone Chemical group O=[13C]1CCCC1 BGTOWKSIORTVQH-HOSYLAQJSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000001683 mentha spicata herb oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000019721 spearmint oil Nutrition 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210571398.5A CN103044226B (en) | 2012-12-26 | 2012-12-26 | Method for preparing cyclopentanone from adipic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210571398.5A CN103044226B (en) | 2012-12-26 | 2012-12-26 | Method for preparing cyclopentanone from adipic acid |
Publications (2)
Publication Number | Publication Date |
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CN103044226A CN103044226A (en) | 2013-04-17 |
CN103044226B true CN103044226B (en) | 2014-09-03 |
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Family Applications (1)
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CN201210571398.5A Active CN103044226B (en) | 2012-12-26 | 2012-12-26 | Method for preparing cyclopentanone from adipic acid |
Country Status (1)
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CN (1) | CN103044226B (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105195063B (en) * | 2015-09-29 | 2017-10-27 | 山东国润生物医药有限公司 | A kind of decarboxylation device that cyclopentanone is prepared for adipic acid |
CN105418342A (en) * | 2015-11-09 | 2016-03-23 | 贝利化学(张家港)有限公司 | High-temperature decarboxylation method |
CN105585824A (en) | 2016-03-07 | 2016-05-18 | 金发科技股份有限公司 | Biodegradable polyester composition |
CN105585826A (en) | 2016-03-07 | 2016-05-18 | 金发科技股份有限公司 | Biodegradable polyester composition |
CN105585825A (en) | 2016-03-07 | 2016-05-18 | 杨红梅 | Biodegradable polyester composition |
CN105713356B (en) | 2016-03-07 | 2017-05-31 | 杨红梅 | A kind of Biodegradable polyester composition |
CN105585827A (en) | 2016-03-07 | 2016-05-18 | 金发科技股份有限公司 | Biodegradable polyester composition |
CN108912081A (en) * | 2018-06-18 | 2018-11-30 | 苏州盖德精细材料有限公司 | A kind of synthetic method of medicine intermediate Tetrahydro-pyran-4-one |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2705666B1 (en) * | 1993-05-28 | 1995-07-21 | Rhone Poulenc Chimie | Process for the preparation of a cyclic ketone. |
CN1284761C (en) * | 2004-06-21 | 2006-11-15 | 沈阳工业大学 | Method for producing cyclopentanone, cyclopentanol |
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2012
- 2012-12-26 CN CN201210571398.5A patent/CN103044226B/en active Active
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C14 | Grant of patent or utility model | ||
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CP01 | Change in the name or title of a patent holder | ||
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Address after: 223300 No. 216 Changjiang East Road, Huaiyin District, Jiangsu, Huaian Patentee after: Wanxiang Technology Co.,Ltd. Address before: 223300 No. 216 Changjiang East Road, Huaiyin District, Jiangsu, Huaian Patentee before: HUAIAN WAN BANG SPICE INDUSTRY Co.,Ltd. |
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CP03 | Change of name, title or address |
Address after: 223300 No. 216 Changjiang East Road, Huaiyin District, Jiangsu, Huaian Patentee after: Wanxiang Technology Group Co.,Ltd. Country or region after: China Address before: 223300 No. 216 Changjiang East Road, Huaiyin District, Jiangsu, Huaian Patentee before: Wanxiang Technology Co.,Ltd. Country or region before: China |