AU2021101234A4 - Cyclopentadienyl three-membered ring fuel, preparation method and application thereof, and airospace aircraft fuel - Google Patents
Cyclopentadienyl three-membered ring fuel, preparation method and application thereof, and airospace aircraft fuel Download PDFInfo
- Publication number
- AU2021101234A4 AU2021101234A4 AU2021101234A AU2021101234A AU2021101234A4 AU 2021101234 A4 AU2021101234 A4 AU 2021101234A4 AU 2021101234 A AU2021101234 A AU 2021101234A AU 2021101234 A AU2021101234 A AU 2021101234A AU 2021101234 A4 AU2021101234 A4 AU 2021101234A4
- Authority
- AU
- Australia
- Prior art keywords
- metal
- cyclopentadienyl
- membered ring
- fuel
- reaction
- 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.)
- Ceased
Links
- 239000000446 fuel Substances 0.000 title claims abstract description 57
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims abstract description 58
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 47
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 29
- 239000002184 metal Substances 0.000 claims description 26
- 229910052751 metal Inorganic materials 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 11
- 239000007848 Bronsted acid Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 238000005888 cyclopropanation reaction Methods 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- NFQIAEMCQGTTIR-UHFFFAOYSA-N Repirinast Chemical compound C12=CC=C(C)C(C)=C2NC(=O)C2=C1OC(C(=O)OCCC(C)C)=CC2=O NFQIAEMCQGTTIR-UHFFFAOYSA-N 0.000 claims description 7
- GUOAPVPPPVLIQQ-UHFFFAOYSA-N dimethyldicyclopentadiene Chemical compound C1=CC2CC1C1C2C(C)C(C)=C1 GUOAPVPPPVLIQQ-UHFFFAOYSA-N 0.000 claims description 7
- 229950009147 repirinast Drugs 0.000 claims description 7
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
- 229910001507 metal halide Inorganic materials 0.000 claims description 6
- 150000005309 metal halides Chemical group 0.000 claims description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- IPSRAFUHLHIWAR-UHFFFAOYSA-N zinc;ethane Chemical compound [Zn+2].[CH2-]C.[CH2-]C IPSRAFUHLHIWAR-UHFFFAOYSA-N 0.000 claims description 3
- -1 4,8-dimethylpentacyclo [6.3.1.02,7.03,5.09,11] dodecane Chemical compound 0.000 claims description 2
- 230000008014 freezing Effects 0.000 abstract description 5
- 238000007710 freezing Methods 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 3
- 239000003380 propellant Substances 0.000 abstract description 2
- ONGINTAPNDPCQW-UHFFFAOYSA-N 2-methylspiro[cyclopropane-1,6'-tricyclo[3.2.1.02,4]octane] Chemical compound CC1CC11C2C3CC3C(C1)C2 ONGINTAPNDPCQW-UHFFFAOYSA-N 0.000 abstract 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 72
- 125000003963 dichloro group Chemical group Cl* 0.000 description 50
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 6
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 5
- 239000002828 fuel tank Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- PPKPKFIWDXDAGC-IHWYPQMZSA-N (z)-1,2-dichloroprop-1-ene Chemical compound C\C(Cl)=C\Cl PPKPKFIWDXDAGC-IHWYPQMZSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- HPYIUKIBUJFXII-UHFFFAOYSA-N Cyclopentadienyl radical Chemical class [CH]1C=CC=C1 HPYIUKIBUJFXII-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L2270/00—Specifically adapted fuels
- C10L2270/04—Specifically adapted fuels for turbines, planes, power generation
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010402286.1 | 2020-05-13 | ||
| CN202010402286.1A CN111548830B (zh) | 2020-05-13 | 2020-05-13 | 环戊二烯基三元环燃料及其制备方法、用途和航空航天飞行器燃料 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2021101234A4 true AU2021101234A4 (en) | 2021-05-06 |
Family
ID=72008155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2021101234A Ceased AU2021101234A4 (en) | 2020-05-13 | 2021-03-10 | Cyclopentadienyl three-membered ring fuel, preparation method and application thereof, and airospace aircraft fuel |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN111548830B (zh) |
| AU (1) | AU2021101234A4 (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117821133A (zh) * | 2024-01-12 | 2024-04-05 | 中国人民解放军军事科学院系统工程研究院 | 一种液体高热值碳氢燃料 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102627535A (zh) * | 2012-03-31 | 2012-08-08 | 天津药物研究院 | 含1,1-二苯基环丙基结构的化合物的制备方法 |
| CN106905285A (zh) * | 2017-05-08 | 2017-06-30 | 华宝香精股份有限公司 | 一种环丙香豆素的合成方法 |
| CN107987107B (zh) * | 2017-12-15 | 2020-03-20 | 上海克琴科技有限公司 | 钌卡宾催化剂及其催化的降冰片烯开环易位聚合反应 |
| CN109970505B (zh) * | 2019-04-19 | 2021-09-21 | 天津大学 | 一种三环丙基化合物、其制备方法及用途 |
-
2020
- 2020-05-13 CN CN202010402286.1A patent/CN111548830B/zh active Active
-
2021
- 2021-03-10 AU AU2021101234A patent/AU2021101234A4/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CN111548830B (zh) | 2021-09-21 |
| CN111548830A (zh) | 2020-08-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGI | Letters patent sealed or granted (innovation patent) |