CN103755666A - 一种含氧环烷烃的催化合成方法 - Google Patents
一种含氧环烷烃的催化合成方法 Download PDFInfo
- Publication number
- CN103755666A CN103755666A CN201410067473.3A CN201410067473A CN103755666A CN 103755666 A CN103755666 A CN 103755666A CN 201410067473 A CN201410067473 A CN 201410067473A CN 103755666 A CN103755666 A CN 103755666A
- Authority
- CN
- China
- Prior art keywords
- synthetic method
- reaction
- solvent
- butyl
- crassitude
- 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
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000007036 catalytic synthesis reaction Methods 0.000 title claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000001301 oxygen Substances 0.000 title abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 title abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 46
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 28
- 238000010189 synthetic method Methods 0.000 claims description 23
- DMWISQNDYKMXFB-UHFFFAOYSA-N 1-chlorocyclohexan-1-ol Chemical compound OC1(Cl)CCCCC1 DMWISQNDYKMXFB-UHFFFAOYSA-N 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- CNZXJVVYUZDIFM-UHFFFAOYSA-M C1(=CC=CC=C1)[P+](C)(C1=CC=CC=C1)C1=CC=CC=C1.I(=O)(=O)[O-] Chemical group C1(=CC=CC=C1)[P+](C)(C1=CC=CC=C1)C1=CC=CC=C1.I(=O)(=O)[O-] CNZXJVVYUZDIFM-UHFFFAOYSA-M 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000004440 column chromatography Methods 0.000 claims description 8
- -1 ether ring alkane Chemical class 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 239000002608 ionic liquid Substances 0.000 claims description 3
- 150000003235 pyrrolidines Chemical group 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 13
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 239000002131 composite material Substances 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 238000009776 industrial production Methods 0.000 abstract description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 description 7
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 238000007363 ring formation reaction Methods 0.000 description 7
- 239000003513 alkali Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NYEWDMNOXFGGDX-UHFFFAOYSA-N 2-chlorocyclohexan-1-ol Chemical compound OC1CCCCC1Cl NYEWDMNOXFGGDX-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- YSLIEJFPLGXOBP-UHFFFAOYSA-N 2-iodocyclohexan-1-ol Chemical compound OC1CCCCC1I YSLIEJFPLGXOBP-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 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
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002118 epoxides Chemical group 0.000 description 1
- 229920006334 epoxy coating Polymers 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
- C07D301/26—Y being hydrogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410067473.3A CN103755666B (zh) | 2014-02-26 | 2014-02-26 | 一种含氧环烷烃的催化合成方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410067473.3A CN103755666B (zh) | 2014-02-26 | 2014-02-26 | 一种含氧环烷烃的催化合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103755666A true CN103755666A (zh) | 2014-04-30 |
CN103755666B CN103755666B (zh) | 2015-12-02 |
Family
ID=50523027
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410067473.3A Active CN103755666B (zh) | 2014-02-26 | 2014-02-26 | 一种含氧环烷烃的催化合成方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN103755666B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104695023A (zh) * | 2015-02-14 | 2015-06-10 | 河北科技大学 | 一水合四氢吡咯-2-羧酸单晶及其制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102993131A (zh) * | 2012-12-27 | 2013-03-27 | 南京工业大学 | 一种邻氯环己醇环化制备环氧环己烷的方法 |
-
2014
- 2014-02-26 CN CN201410067473.3A patent/CN103755666B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102993131A (zh) * | 2012-12-27 | 2013-03-27 | 南京工业大学 | 一种邻氯环己醇环化制备环氧环己烷的方法 |
Non-Patent Citations (1)
Title |
---|
SHALLU ETC.: "Envirocat (K10-MX)-catalyzed regioselective transformation of alkenes into lodohydrins and lodo ethers and further conversion of lodohydrin to epoxides using Al2O3-Na2CO3 under MWI", 《SYNTHETIC COMMUNICATIONS》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104695023A (zh) * | 2015-02-14 | 2015-06-10 | 河北科技大学 | 一水合四氢吡咯-2-羧酸单晶及其制备方法 |
CN104695023B (zh) * | 2015-02-14 | 2017-02-01 | 河北科技大学 | 一水合四氢吡咯‑2‑羧酸单晶及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN103755666B (zh) | 2015-12-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102728407B (zh) | 一种(S,S)-salen Co(Ⅱ)催化剂的合成方法及其在拆分末端环氧化合物的应用 | |
CN101168493B (zh) | 一种氟代氯苯的制备方法 | |
CN105152922A (zh) | 一种以光照为条件噻吨酮催化合成苯甲酸的方法 | |
CN103193757B (zh) | 质子酸离子液体催化合成环状碳酸酯的方法 | |
CN110872254B (zh) | 吡唑盐类双离子液体以及利用其催化合成环状碳酸酯的方法 | |
CN106045913A (zh) | 一种带有氨基的咪唑高铼酸盐离子液体及其制备方法和应用 | |
CN110078702A (zh) | 一种聚离子液体框架催化剂制备环状碳酸酯的方法 | |
CN103755666B (zh) | 一种含氧环烷烃的催化合成方法 | |
CN102276475A (zh) | 一种合成1,5-二硝基萘和1,8-二硝基萘的方法 | |
CN105642363B (zh) | 用于二氧化碳合成苯乙烯环状碳酸酯的双负载催化剂及制备方法与应用 | |
Hu et al. | Highly efficient synthesis of cyclic carbonates from carbon dioxide and epoxides catalyzed by ionic liquid [Heemim][ZrCl 5] | |
CN107011211B (zh) | 一种对苯二甲腈的制备方法 | |
CN102603564B (zh) | α-氰基丙烯酸酯单体的合成工艺 | |
CN104086509A (zh) | 甲基丙烯酸缩水甘油酯的合成方法 | |
CN103420835A (zh) | 一种利用甲基丙烯醛制备甲基丙烯酸甲酯的方法 | |
CN103172777A (zh) | 一种制备聚丁二烯环氧树脂的方法 | |
CN102850270A (zh) | 一锅法制备羟基取代-3,4-二氢-2(1h)-喹啉酮类化合物的方法 | |
CN106831527A (zh) | 吡咯及其制备方法 | |
CN102408454B (zh) | 一种合成茂金属羰基衍生物的方法 | |
CN103204777B (zh) | 一种催化酯交换的方法 | |
CN104558517A (zh) | 双酚a型环氧树脂合成方法 | |
CN106045933B (zh) | 一种噁唑烷酮的制备方法 | |
CN107445828B (zh) | 合成乙醛酸酯的方法 | |
CN115819188B (zh) | 一种4-叔丁基-2-(α-甲基苄基)苯酚的制备方法 | |
CN104098531B (zh) | 一种1,2-环氧丁烷的合成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20151102 Address after: Gold Tingcun Jinting town construction of 312458 Zhejiang province Shaoxing city Shengzhou City 2 Road No. 7 Applicant after: SHENGZHOU YIYUAN INVESTMENT MANAGEMENT CO.,LTD. Address before: The streets of Sanjiang bay village of Shengzhou city in Zhejiang province Shaoxing city 312499 Applicant before: Zhang Fangjun |
|
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CB03 | Change of inventor or designer information |
Inventor after: Wang Ping Inventor before: Zhang Fangjun |
|
CB03 | Change of inventor or designer information | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20170417 Address after: 361101 Fujian, Xiamen torch hi tech Zone (Xiangan) Industrial Zone Jianye Building D block, Room 502, room 504 Patentee after: XIAMEN OURUIJIE BIOTECHNOLOGY CO.,LTD. Address before: Gold Tingcun Jinting town construction of 312458 Zhejiang province Shaoxing city Shengzhou City 2 Road No. 7 Patentee before: SHENGZHOU YIYUAN INVESTMENT MANAGEMENT CO.,LTD. |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A catalytic synthesis method of oxygenated cycloalkanes Effective date of registration: 20201225 Granted publication date: 20151202 Pledgee: Xiamen finance Company limited by guarantee Pledgor: XIAMEN OURUIJIE BIOTECHNOLOGY Co.,Ltd. Registration number: Y2020980009948 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20231026 Granted publication date: 20151202 Pledgee: Xiamen finance Company limited by guarantee Pledgor: XIAMEN OURUIJIE BIOTECHNOLOGY CO.,LTD. Registration number: Y2020980009948 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A Catalytic Synthesis Method for Oxygenated Cycloalkanes Effective date of registration: 20231031 Granted publication date: 20151202 Pledgee: Bank of China Limited Xiamen Xiang'an sub branch Pledgor: XIAMEN OURUIJIE BIOTECHNOLOGY CO.,LTD. Registration number: Y2023980063461 |