CN1200989C - 具有改善了热稳定性的基于多苯基甲烷的传热流体 - Google Patents
具有改善了热稳定性的基于多苯基甲烷的传热流体 Download PDFInfo
- Publication number
- CN1200989C CN1200989C CN01810395.2A CN01810395A CN1200989C CN 1200989 C CN1200989 C CN 1200989C CN 01810395 A CN01810395 A CN 01810395A CN 1200989 C CN1200989 C CN 1200989C
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- 230000001747 exhibiting effect Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 130
- 239000013529 heat transfer fluid Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims description 81
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical class CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 44
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Substances C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 24
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 17
- 238000005984 hydrogenation reaction Methods 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 9
- 229940073608 benzyl chloride Drugs 0.000 claims description 9
- 229910001502 inorganic halide Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- -1 xylyl phenylmethane Chemical compound 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000005194 fractionation Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- LIJPUYWRAJPDLJ-UHFFFAOYSA-N 1-benzyl-1,2,3,4-tetrahydronaphthalene Chemical compound C1CCC2=CC=CC=C2C1CC1=CC=CC=C1 LIJPUYWRAJPDLJ-UHFFFAOYSA-N 0.000 abstract 1
- 229920006389 polyphenyl polymer Polymers 0.000 abstract 1
- 239000000047 product Substances 0.000 description 22
- 239000003795 chemical substances by application Substances 0.000 description 20
- 238000010438 heat treatment Methods 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 238000010926 purge Methods 0.000 description 7
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- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000010835 comparative analysis Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 3
- GDPISEKNRFFKMM-UHFFFAOYSA-N 1,3-diphenylpropan-2-ylbenzene Chemical class C=1C=CC=CC=1CC(C=1C=CC=CC=1)CC1=CC=CC=C1 GDPISEKNRFFKMM-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical class C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
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- 238000001914 filtration Methods 0.000 description 2
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- 239000012535 impurity Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- PKQYSCBUFZOAPE-UHFFFAOYSA-N 1,2-dibenzyl-3-methylbenzene Chemical compound C=1C=CC=CC=1CC=1C(C)=CC=CC=1CC1=CC=CC=C1 PKQYSCBUFZOAPE-UHFFFAOYSA-N 0.000 description 1
- GNPWYHFXSMINJQ-UHFFFAOYSA-N 1,2-dimethyl-3-(1-phenylethyl)benzene Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=CC=CC=C1 GNPWYHFXSMINJQ-UHFFFAOYSA-N 0.000 description 1
- GPUVIJGDONRCTL-UHFFFAOYSA-N 2-benzyl-1,3,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(CC=2C=CC=CC=2)=C1C GPUVIJGDONRCTL-UHFFFAOYSA-N 0.000 description 1
- PJUAZXJAACRSBB-UHFFFAOYSA-N CClCC1=CC=CC=C1 Chemical compound CClCC1=CC=CC=C1 PJUAZXJAACRSBB-UHFFFAOYSA-N 0.000 description 1
- 101100008046 Caenorhabditis elegans cut-2 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101100137177 Drosophila melanogaster polyph gene Proteins 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/10—Liquid materials
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR00/03944 | 2000-03-29 | ||
| FR0003944A FR2807059B1 (fr) | 2000-03-29 | 2000-03-29 | Fluide de transfert de chaleur a base de polyphenylmethanes ayant une stabilite thermique amelioree |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1432054A CN1432054A (zh) | 2003-07-23 |
| CN1200989C true CN1200989C (zh) | 2005-05-11 |
Family
ID=8848596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN01810395.2A Expired - Fee Related CN1200989C (zh) | 2000-03-29 | 2001-03-27 | 具有改善了热稳定性的基于多苯基甲烷的传热流体 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7011765B2 (enExample) |
| EP (1) | EP1268705B1 (enExample) |
| JP (1) | JP4845319B2 (enExample) |
| CN (1) | CN1200989C (enExample) |
| AT (1) | ATE317885T1 (enExample) |
| AU (1) | AU2001246654A1 (enExample) |
| DE (1) | DE60117243T2 (enExample) |
| ES (1) | ES2258522T3 (enExample) |
| FR (1) | FR2807059B1 (enExample) |
| NO (1) | NO20024655L (enExample) |
| WO (1) | WO2001072924A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100584809C (zh) * | 2006-12-18 | 2010-01-27 | 宝山钢铁股份有限公司 | 1,2,3,4-四氢化萘传热流体的再生利用工艺 |
| US9010318B2 (en) | 2009-09-04 | 2015-04-21 | Wisconsin Alumni Research Foundation | Extended-range heat transfer fluid using variable composition |
| CN104178092A (zh) * | 2013-05-27 | 2014-12-03 | 山东恒导石油化工股份有限公司 | 一种高温有机热载体及其生产工艺 |
| CN106349000B (zh) * | 2015-07-17 | 2018-10-26 | 江苏中能化学科技股份有限公司 | 导热流体1-苯基-1-(环己基甲苯)基乙烷异构体及其合成方法 |
| US10584271B2 (en) * | 2016-12-20 | 2020-03-10 | ORG Chem Group | Heat transfer fluid and process for preparing same |
| FR3077295A1 (fr) | 2018-01-31 | 2019-08-02 | Arkema France | Utilisation d'un compose polyaryle comme fluide de transfert de chaleur |
| FR3106345B1 (fr) * | 2020-01-20 | 2023-07-21 | Arkema France | Utilisation d’une composition de transfert de chaleur pour réguler la température d’une batterie |
| FR3117113B1 (fr) * | 2020-12-09 | 2024-04-12 | Arkema France | Formulation liquide pour stockage d’hydrogène |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5654353B2 (enExample) * | 1973-02-12 | 1981-12-24 | ||
| JPS6169736A (ja) * | 1984-09-14 | 1986-04-10 | Idemitsu Kosan Co Ltd | テトラリン誘導体の製法 |
| JPS62246997A (ja) * | 1986-04-21 | 1987-10-28 | Idemitsu Kosan Co Ltd | トラクシヨンドライブ用流体 |
| JPS62263133A (ja) * | 1986-05-12 | 1987-11-16 | Idemitsu Kosan Co Ltd | ジアラルキル芳香族炭化水素の製造方法 |
| GB8615400D0 (en) * | 1986-06-24 | 1986-07-30 | Isc Chemicals Ltd | Flourinated polycyclic compounds |
| FR2618142B1 (fr) * | 1987-07-16 | 1989-10-06 | Atochem | Compositions d'oligomeres de polyarylalcanes contenant des motifs xylene et leur procede de fabrication |
| US4956120A (en) * | 1987-07-16 | 1990-09-11 | Atochem | Polyarylalkane oligomer compositions and process for their manufacture |
| US5192463A (en) | 1989-02-20 | 1993-03-09 | Atochem | Low temperature, polyphenylmethane-based dielectric compositions |
| FR2643366B1 (fr) * | 1989-02-20 | 1991-09-06 | Atochem | Compositions a base de polyphenylmethanes, leur procede de fabrication et leur application comme dielectrique |
| FR2658812B1 (fr) * | 1990-02-27 | 1992-05-15 | Atochem | Compositions dielectriques a base de benzyltoluene et de (methylbenzyl) xylene. |
| JP2760643B2 (ja) * | 1990-08-03 | 1998-06-04 | 東燃株式会社 | ジフェニルブタンの製造方法 |
| FR2673189A1 (fr) * | 1991-02-22 | 1992-08-28 | Atochem | Utilisation d'isomeres de mono et bis(methylbenzyl)xylene comme fluide de transfert technique. |
| DE69804442T2 (de) * | 1997-05-09 | 2002-08-08 | The Dow Chemical Co., Midland | Wärmetransportflüssigkeitsmischungen enthaltend 1,2,3,4-tetrahydro-(1-phenyl)naphthalen |
-
2000
- 2000-03-29 FR FR0003944A patent/FR2807059B1/fr not_active Expired - Fee Related
-
2001
- 2001-03-27 AT AT01919583T patent/ATE317885T1/de not_active IP Right Cessation
- 2001-03-27 JP JP2001571841A patent/JP4845319B2/ja not_active Expired - Fee Related
- 2001-03-27 EP EP01919583A patent/EP1268705B1/fr not_active Expired - Lifetime
- 2001-03-27 AU AU2001246654A patent/AU2001246654A1/en not_active Abandoned
- 2001-03-27 WO PCT/FR2001/000930 patent/WO2001072924A1/fr not_active Ceased
- 2001-03-27 DE DE60117243T patent/DE60117243T2/de not_active Expired - Lifetime
- 2001-03-27 ES ES01919583T patent/ES2258522T3/es not_active Expired - Lifetime
- 2001-03-27 CN CN01810395.2A patent/CN1200989C/zh not_active Expired - Fee Related
- 2001-03-27 US US10/240,093 patent/US7011765B2/en not_active Expired - Lifetime
-
2002
- 2002-09-27 NO NO20024655A patent/NO20024655L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US7011765B2 (en) | 2006-03-14 |
| DE60117243T2 (de) | 2007-02-15 |
| FR2807059B1 (fr) | 2002-05-17 |
| NO20024655D0 (no) | 2002-09-27 |
| WO2001072924A1 (fr) | 2001-10-04 |
| EP1268705B1 (fr) | 2006-02-15 |
| AU2001246654A1 (en) | 2001-10-08 |
| NO20024655L (no) | 2002-11-01 |
| FR2807059A1 (fr) | 2001-10-05 |
| ATE317885T1 (de) | 2006-03-15 |
| JP4845319B2 (ja) | 2011-12-28 |
| CN1432054A (zh) | 2003-07-23 |
| ES2258522T3 (es) | 2006-09-01 |
| US20040031949A1 (en) | 2004-02-19 |
| DE60117243D1 (de) | 2006-04-20 |
| JP2003528970A (ja) | 2003-09-30 |
| EP1268705A1 (fr) | 2003-01-02 |
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