CN103980241A - Delta-valerolactone production method - Google Patents
Delta-valerolactone production method Download PDFInfo
- Publication number
- CN103980241A CN103980241A CN201410162813.0A CN201410162813A CN103980241A CN 103980241 A CN103980241 A CN 103980241A CN 201410162813 A CN201410162813 A CN 201410162813A CN 103980241 A CN103980241 A CN 103980241A
- Authority
- CN
- China
- Prior art keywords
- valerolactone
- production method
- pentanediol
- content
- hydrogen
- 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.)
- Granted
Links
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 title claims abstract description 65
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 11
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 8
- 230000000694 effects Effects 0.000 claims abstract description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 5
- 229910052709 silver Inorganic materials 0.000 claims description 5
- 239000004332 silver Substances 0.000 claims description 5
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 4
- 238000009834 vaporization Methods 0.000 claims description 4
- 230000008016 vaporization Effects 0.000 claims description 4
- 239000006200 vaporizer Substances 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical group O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims 2
- 239000000292 calcium oxide Substances 0.000 claims 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims 2
- 229910052684 Cerium Inorganic materials 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052746 lanthanum Inorganic materials 0.000 claims 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- 229910052814 silicon oxide Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 238000005516 engineering process Methods 0.000 abstract description 5
- 238000011160 research Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 229940043375 1,5-pentanediol Drugs 0.000 abstract 5
- 238000005457 optimization Methods 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 2
- 239000012043 crude product Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 230000003245 working effect Effects 0.000 description 2
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410162813.0A CN103980241B (en) | 2014-04-23 | 2014-04-23 | A kind of production method of δ-valerolactone |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410162813.0A CN103980241B (en) | 2014-04-23 | 2014-04-23 | A kind of production method of δ-valerolactone |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103980241A true CN103980241A (en) | 2014-08-13 |
CN103980241B CN103980241B (en) | 2015-10-21 |
Family
ID=51272436
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410162813.0A Active CN103980241B (en) | 2014-04-23 | 2014-04-23 | A kind of production method of δ-valerolactone |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN103980241B (en) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20010009964A1 (en) * | 2000-01-14 | 2001-07-26 | Dairen Chemical Corporation | Catalyst for preparing lactone and a method for preparing lactone |
CN101977684A (en) * | 2008-03-19 | 2011-02-16 | 巴斯夫欧洲公司 | Use of a supported catalyst containing precious metal for oxidative dehydrogenation |
US20110237806A1 (en) * | 2008-12-05 | 2011-09-29 | Basf Se | Process for preparing delta-valerolactone in the gas phase |
-
2014
- 2014-04-23 CN CN201410162813.0A patent/CN103980241B/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20010009964A1 (en) * | 2000-01-14 | 2001-07-26 | Dairen Chemical Corporation | Catalyst for preparing lactone and a method for preparing lactone |
CN101977684A (en) * | 2008-03-19 | 2011-02-16 | 巴斯夫欧洲公司 | Use of a supported catalyst containing precious metal for oxidative dehydrogenation |
US20110237806A1 (en) * | 2008-12-05 | 2011-09-29 | Basf Se | Process for preparing delta-valerolactone in the gas phase |
Non-Patent Citations (3)
Title |
---|
FUMIYA SATO ET AL.: "Dehydration of 1,5-pentanediol over rare earth oxides", 《APPLIED CATALYSIS A: GENERAL》 * |
K. INUI ET AL.: "Dehydrogenative Esterification over Copper-based Catalyst", 《STUDIES IN SURFACE SCIENCE AND CATALYSIS》 * |
程丹等: "δ-环戊内酯的合成及应用", 《安徽化工》 * |
Also Published As
Publication number | Publication date |
---|---|
CN103980241B (en) | 2015-10-21 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CB03 | Change of inventor or designer information |
Inventor after: Song Guoquan Inventor after: Xiao Qiang Inventor after: Yang Li Inventor after: Yan Guangxue Inventor after: Wu Zhengling Inventor after: Wu Yanbin Inventor before: Xiao Qiang Inventor before: Song Guoquan Inventor before: Yang Li Inventor before: Yan Guangxue |
|
CB03 | Change of inventor or designer information | ||
CP03 | Change of name, title or address |
Address after: 457000 Meiqi Chemical Co., Ltd., West Section of Shengli Road, Puyang City, Henan Province Patentee after: New Maiqi Materials Co.,Ltd. Country or region after: China Address before: 457000 Meiqi Chemical Co., Ltd., West Section of Shengli Road, Puyang City, Henan Province Patentee before: MYJ CHEMICAL CO.,LTD. Country or region before: China |