WO2001059029A1 - Thermal fluid blends containing 1,2,3,4-tetrahydro(1-phenylethyl)naphthalene - Google Patents
Thermal fluid blends containing 1,2,3,4-tetrahydro(1-phenylethyl)naphthalene Download PDFInfo
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- WO2001059029A1 WO2001059029A1 PCT/US2001/002676 US0102676W WO0159029A1 WO 2001059029 A1 WO2001059029 A1 WO 2001059029A1 US 0102676 W US0102676 W US 0102676W WO 0159029 A1 WO0159029 A1 WO 0159029A1
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- 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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- This invention relates to high temperature thermal (heat transfer) fluids, and more particularly to heat transfer fluids comprising blends of 1 ,2,3,4 tetrahydro( 1 -phenyl- ethyl)naphthalene and an alkyl biphenyl.
- Heat transfer fluids are widely used for temperature control in manufacturing facilities.
- the ability of a heat transfer fluid to resist degradation at elevated temperatures is referenced through a performance property denoted as “thermal stability”.
- thermal stability As a heat transfer fluid undergoes degradation, both volatile materials (which "boil” or evaporate from the fluid) and “heavy” materials (also denoted as “highers” or “residue”) are formed within the heat transfer fluid.
- Such heavy components elevate the heat transfer fluid's viscosity and thereby lead to an increase in film temperature in the portion of heat transfer fluid denoted as the "film” which exists at the interface of the heat transfer fluid and a high temperature (respective to the temperature of the fluid) surface; any such differential in film temperature above the temperature of the less viscous portion of the heat transfer fluid augments the rate of degradation in the heat transfer fluid as a whole insofar as the film portion intermixes with the remainder of the heat transfer fluid.
- polymers formed through the degradation of a heat transfer fluid tend to darken the fluid and ultimately deposit on surfaces in the system; these deposits are detrimental to system efficiency and potentially lead to system failure.
- degraded heat transfer fluid must, therefore, be periodically replaced with fresh or recycled heat transfer fluid.
- This invention is a heat transfer fluid which comprises a mixture of 1 ,2,3,4- tetrahydro(l-phenylethyl)naphthalene (ST-THN) as a first fluid component and an alkyl biphenyl as the second fluid component. It has been discovered, surprisingly, that mixing ST-THN with specific second fluid components as described herein yields a heat transfer fluid with a thermal stability property significantly improved over the thermal stability of either of the components prior to their blending.
- ST-THN 1 ,2,3,4- tetrahydro(l-phenylethyl)naphthalene
- the heat transfer fluid is beneficially admixed from l,2,3,4-tetrahydro(l- phenylethyl)naphthalene; and a second fluid characterized as an aromatic component having alkyl, cyclohexyl, or cyclopentyl linkages; preferably, alkyl linkages.
- the second fluid is preferably other than a degradation product of l,2,3,4-tetrahydro(l- phenylethyl)naphthalene.
- the heat transfer fluid is admixed from: l,2,3,4-tetrahydro(l- phenylethyl)naphthalene; and a second fluid selected from the group consisting of dibenzyl toluene, partially hydrogenated terphenyl, dibenzyl benzene, xylyl toluene, dixylyl toluene, xylyl xylene, dixylyl xylene, diethylbenzene, 1,1-diphenylethane, benzene alkylates, alkylnaphthalenes, alkyl biphenyls, diphenylmethane, cyclohexyl- diphenyl ether, alkyl diphenyl ethers, triphenylmethane, tritolylmethane, and mixtures thereof.
- a second fluid selected from the group consisting of dibenzyl toluene, partially hydrogenated terphenyl,
- the heat transfer fluid is admixed from: l,2,3,4-tetrahydro(l- phenylethyl)naphthalene as a first fluid component and a second fluid component selected from the group consisting of a partially hydrogenated terphenyl, an alkyl biphenyl, and mixtures thereof;
- the alkyl biphenyl is selected from the group consisting of 1,1-diphenylethane, methylbiphenyl, ethylbiphenyl, diethylbiphenyl, triethyl- biphenyl, propylbiphenyl, dipropylbiphenyl, isopropylbiphenyl, diisopropylbiphenyl, butylbiphenyl, dibutylbiphenyl, and mixtures thereof.
- Another embodiment of the present invention is a method for preparing a heat transfer fluid.
- the method comprises admixing a first fluid component of l,2,3,4-tetrahydro(l- phenylethyl)naphthalene with a second fluid component as described above.
- the 1 ,2,3,4-tetrahydro( 1 -phenylethyl)naphthalene component preferably constitutes at least 10 percent by weight of the total heat transfer fluid.
- a further embodiment of the present invention is a method of controlling the temperature of a system.
- the method comprises adding to the system a first fluid component of l,2,3,4-tetrahydro(l-phenylethyl)naphthalene and a second fluid component as described above.
- the l,2,3,4-tetrahydro(l-phenylethyl)naphthalene and the second fluid component are, in one embodiment, added to the system separately, or. in another embodiment, admixed together prior to addition to the system.
- Figures 1 A and IB show fluid degradation of a mixture of l,2,3,4-tetrahydro(l- phenylethyl)naphthalene (ST-THN) and dibenzyl toluene (DBT) compared to the fluid degradation of each component alone when tested at 650°F (343°C) and at 675°F (357°C).
- Figures 2A and 2B show fluid degradation of a mixture of 1 ,2,3,4-tetrahydro( 1 - phenylethyl)naphthalene (ST-THN) and partially hydrogenated terphenyl (HT) compared to the fluid degradation of each component alone when tested at 650°F (343°C) and at 675°F (357°C).
- ST-THN 1 ,2,3,4-tetrahydro( 1 - phenylethyl)naphthalene
- HT partially hydrogenated terphenyl
- Figure 3 shows a Boiling Point - Retention Time relationship for a standard solution of alkyl aromatics.
- Figure 4 presents a Boiling Point - Evaporated Content relationship for DOWTHERMTM RP heat transfer fluid.
- Figure 5 presents a Boiling Point - Evaporated Content relationship for degraded DOWTHERMTM RP heat transfer fluid.
- Figure 6 presents a Boiling Point - Evaporated Content relationship for Partially Hydrogenated Terphenyl Fluid.
- Figure 7 presents a Boiling Point - Evaporated Content relationship for degraded Partially Hydrogenated Terphenyl Fluid.
- Figure 8 presents a Boiling Point - Evaporated Content relationship for Dibenzyltoluene.
- Figure 9 presents a Boiling Point - Evaporated Content relationship for degraded Dibenzyltoluene.
- Figure 10 presents a Boiling Point - Evaporated Content relationship for a 50/50 Blend of ST-THN and a DIPBP Fluid.
- Figure 11 presents a Boiling Point - Evaporated Content relationship for a degraded 50/50 Blend of ST-THN and DIPBP Fluid.
- l,2,3,4-Tetrahydro(l-phenylethyl)naphthalene is also called styrenated tetrahydronaphthalene (ST-THN), or 1 -phenyl- 1- tetrahydronaphthylehane (PTE), and is an isomeric mixture of l,2,3,4-tetrahydro-5-(l- phenylethyl)naphthalene and l,2,3,4-tetrahydro-6-(l-phenylethyl)naphthalene.
- ST-THN styrenated tetrahydronaphthalene
- PTE 1 -phenyl- 1- tetrahydronaphthylehane
- ST- THN may be prepared by reaction of tetralin with styrene as described, for example, in Matsumoto et al., Ind. Eng. Chem., Prod. Res. Dev., Vol. 15, no. 3, 1976, pp. 215-216 ST-THN is also commercially available from The Dow Chemical Company as DOWTHERMTM RP heat transfer fluid
- Useful second fluids may be characterized as a fully aromatic component having alkyl, cyclohexyl, or cyclopentyl linkages, with the proviso that the second fluid is other than a degradation product of l,2,3,4-tetrahydro(l-phenylethyl)naphthalene
- Fully aromatic components include benzene, biphenyl, and naphthalene structures
- Representative alkyl linkages include Cl to C4 linear or branched hydrocarbon moieties
- the heat transfer fluid is admixed from 1 ,2,3,4-tetrahydro( 1 - phenylethyl)naphthalene and an alkyl biphenyl (R(C 6 H 5 ) 2 ) Partially hydrogenated terphenyls (C 6 H 4 (C H 5 )(C 6 Hn)and C 6 H (C6Hn) ), dibenzyl benzene (C 6 H 4 (C 6 H,CH 2 ) 2 ), dibenzyl toluene (C 6 H 3 (C 6 H 5 CH 2 ) 2 (CH 3 )) xylyl toluene (C 6 H 4 (C 6 H 4 (CH 3 )CH 2 )(CH )), dixylyl toluene (C 6 H (C 6 H 4 (CH 3 )CH 2 ) 2 (CH 3 )), xylyl xylene (C 6 H 3 (C 6 H 4 (CH 3 )CH 2 )),
- the heat transfer fluid is admixed from 1 ,2,3,4-tetrahydro(l- phenylethyl)naphthalene and an alkyl biphenyl (R x (C 6 H y ) 2 where x is 1, 2, or 3, y is 3, 4, or 5, and R has, separately in each instance of occurrence of the R moiety in the formula, between 1 and 4 carbon atoms)
- R x (C 6 H y ) 2 where x is 1, 2, or 3, y is 3, 4, or 5, and R has, separately in each instance of occurrence of the R moiety in the formula, between 1 and 4 carbon atoms
- Partially hydrogenated terphenyls C 6 H 5 )(C 6 H 4 )(C 6 H ⁇ ) and (C 6 H 4 )(C 6 H
- methylbiphenyl CH 3 )(C 6 H 4 )(C 6 H 5
- ethylbiphenyl C 2 H 5 )(C 6 H 4
- the second fluid component is isopropylbiphenyl. diisopropylbiphenyl, triethylbiphenyl, a partially hydrogenated terphenyl, 1 ,1-diphenylethane, or a mixture thereof. Most preferably, the second fluid component is isopropylbiphenyl or diisopropylbiphenyl.
- Various heat transfer fluids are well-known in the art and many variations of such heat transfer fluids are, in alternative embodiments, useful in combination with the heat transfer fluid of the present invention.
- the second fluid component is partially hydrogenated terphenyl.
- the partially hydrogenated terphenyl has any combination of ortho-, meta-, and para- isomers.
- Partially hydrogenated terphenyl is commercially available, for example, from The Dow Chemical Company as DOWTHERMTM HT heat transfer fluid, as ThermSTM 900 heat transfer fluid from Nippon Steel Chemical Co., and from Solutia as THERMLNOLTM 66 heat transfer fluid.
- the l,2,3,4-tetrahydro(l-phenylethyl)naphthalene component comprises at least 10 percent by weight of the heat transfer fluid; more preferably, at least 25 percent.
- the l,2,3,4-tetrahydro(l-phenylethyl)naphthalene component comprises less than 90 percent by weight of the heat transfer fluid; more preferably, less than 75 percent. Unless otherwise stated herein, all percentages are given on a weight basis compared to the total weight of the heat transfer fluid.
- Another embodiment of the present invention is a method for preparing a heat transfer fluid.
- the method comprises admixing a first fluid component of 1 ,2,3,4-tetrahydro(l- phenylethyl)naphthalene with an alkyl biphenyl second fluid component as described above.
- a homogeneous heat transfer fluid may be obtained by mixing through any conventional means, such as pumping and recirculating. Ambient temperature and pressure are suitable mixing conditions.
- a preferred embodiment comprises admixing l,2,3,4-tetrahydro(l-phenyl- ethyl)naphthalene with an alkyl biphenyl as described above.
- a highly preferred embodiment comprises admixing at least 10 percent l,2,3,4-tetrahydro(l-phenyl- ethyl)naphthalene by weight with an alkyl biphenyl; more preferably, at least 25 percent l,2,3,4-tetrahydro(l-phenylethyl)naphthalene by weight.
- Another embodiment of the present invention is a method of controlling the temperature of a system.
- the method comprises adding to the system 1,2,3,4- tetrahydro(l-phenylethyl)naphthalene and an alkyl biphenyl as described above.
- alternative suggested second fluids are used in place of or with the alkyl biphenyl.
- Suitable weight percents are as described herein above.
- a preferred embodiment comprises adding at least 25 percent l,2,3,4-tetrahydro(l-phenylethyl)naphthalene by weight and an alkyl biphenyl to a system to control system temperature.
- a first fluid component of l,2,3,4-tetrahydro(l-phenylethyl)naphthalene is, in one embodiment, admixed with the second fluid component prior to addition to the system; in another embodiment, the second fluid component is added to the system separately.
- the blending of l,2,3,4-tetrahydro(l-phenyl- ethyl)naphthalene and an isopropylbiphenyl provides a heat transfer fluid having superior thermal properties to the properties of a heat transfer fluid of either component used individually without the benefit of the other blended component.
- the heat transfer fluid blend of l,2,3,4-tetrahydro(l-phenylethyl)naphthalene with triethylbiphenyl also demonstrates superior thermal properties to the properties of a heat transfer fluid of either component used individually without the benefit of the other blended component.
- blends of l,2,3,4-tetrahydro(l-phenylethyl)naphthalene and 1,1-diphenylethane afford heat transfer fluids with superior thermal properties to the properties of a heat transfer fluid of either component used individually without the benefit of the other blended component.
- diisopropylbiphenyl is blended with partially hydrogenated terphenyls, the resulting heat transfer fluid has excellent thermal properties, superior to the properties of a heat transfer fluid of either component used individually without the benefit of the other blended component.
- the heat transfer fluid blends of the present invention tend to form fewer heavy components, fewer light boiling components, and fewer carbon deposits in the heat exchange system; the heat transfer fluids of the present invention also demonstrate improved thermal stability over the thermal stability of the heat transfer fluid defined by one of the second component fluids prior to the admixing of l,2,3,4-tetrahydro(l-phenylethyl)naphthalene.
- light boiling components are components having boiling points lower than the boiling point of the heat transfer fluid prior to the onset of sustained exposure to temperatures which are expected in heat transfer fluid operational use.
- the second fluid components are either commercially available or are prepared according to published procedures.
- Methylbiphenyl is available from Aldrich Chemical Company, or as SURE SOLTM 177 fluid from Koch Industries.
- Ethylbiphenyl is available from Aldrich Chemical Company or as ThermSTM 600 heat transfer fluid from Nippon Steel Chemical Co.
- Diethylbiphenyl is available as ThermSTM 700 heat transfer fluid from Nippon Steel Chemical Co.
- Triethylbiphenyl is available as ThermSTM 800 heat transfer fluid from Nippon Steel Chemical Co.
- Propylbiphenyl is available from TCI America. Isopropylbiphenyl is available from TCI America.
- Dibenzyltoluene used in some comparative experiments, is available from Nisseki Chemical Texas Inc.
- the xylene derivative fluids may be prepared as described in Informations Chimie, vol. 33, No. 376 (1996) pp.93-96.
- cyclohexyl-diphenyl ether, alkyldiphenylethers, and tritolylmethane are typically prepared according to conventional alkylation procedures.
- Dibenzyl toluene is commercially available from Huls as MARLOTHERMTM SH heat transfer fluid.
- Preparation of a 50/50 mixture of ST-THN and DBT A sample comprising a 1 : 1 weight ratio of ST-THN:dibenzyl toluene was prepared by admixing 550 grams of l,2,3,4-tetrahydro(l-phenylethyl)naphthalene with 550 grams of dibenzyl toluene in a glass container. The mixture was stirred approximately five minutes at ambient pressure and temperature until a homogeneous fluid was obtained.
- Preparation of a 50/50 mixture of ST-THN and HT A sample comprising a 1 : 1 weight ratio of ST-THN:partially hydrogenated terphenyl (HT) was prepared in a similar manner by admixing 580 grams of l,2,3,4-tetrahydro(l-phenylethyl)naphthalene with 580 grams of partially hydrogenated terphenyl.
- Both of these fluid samples were subjected to thermal degradation at 650°F (343°C) and at 675°F (357°C) along with samples of l,2,3,4-tetrahydro(l-phenylethyl)- naphthalene, dibenzyl toluene, and partially hydrogenated terphenyl by placing 40 milliliters of each fluid in a 16 x 1 inch (40.64 x 2.54 cm) carbon steel ampoule which had been evacuated and then purged with nitrogen.
- the fluid samples were heated in a forced air oven (V Series, from Despatch Industries, Inc.) during the experimental timeframe except for weekly removal for testing. Upon removal from the oven, the ampoules were cooled in dry ice before opening.
- the fluid samples were drained into separate containers and heated with heat lamps to complete the recovery of the degraded fluid.
- the resulting fluids were analyzed by gas chromatography to determine the percent of light boiling components in the fluid as an indication of fluid degradation. The lower the percentage of light boiling components, the less the fluid has degraded, therefore, the greater the thermal stability of the fluid.
- Table 1 below shows the results of the degradation tests involving dibenzyl toluene.
- Samples of l,2,3,4-tetrahydro(l-phenylethyl)naphthalene (ST-THN), dibenzyl toluene (DBT), and a 50/50 mixture by weight of l,2,3,4-tetrahydro(l-phenylethyl)naphthalene and dibenzyl toluene were tested at 650°F (343°C) for ten weeks and at 675°F (357°C) for nine weeks in accordance with the procedures described above.
- Tables 3 to 5 provide data obtained from fluid degradation experimental studies in carbon steel. Fluids were degraded by placing about forty grams of fluid in a fourteen inch carbon steel ampoule, sealed under nitrogen, and heated to the indicated temperature. One subset of the fluids were degraded under conditions such that samples were taken out of the oven after each week of degradation. A second subset of the fluids were degraded for a total of 500 hours at the given temperature, then the degradation rate was converted to degradation rate per week. In either case, once the fluids were degraded and taken out of the ampoule, they were analyzed by gas chromatography using ASTM method D2887, "Standard Test method for Boiling Range Distribution of Petroleum Fractions by Gas Chromatography.
- Table 3 shows the results of (a) blending DOWTHERM RP heat transfer fluid, abbreviated as ST-THN, with (1) diisopropylbiphenyls (( ⁇ -Pr) -BP) in the form of SURE SOL 330 ( Trademark of Koch Industries) fluid, and (2) mixtures of monoisopropylbiphenyls (i-Pr-BP) and diisopropylbiphenyls (( ⁇ -Pr) -BP), in the form of SURE SOL 325 fluid, (3) partially hydrogenated terphenyls, denoted as PHT, and (b) degrading the blended fluid at 675°F
- Table 1 examples of the invention are shown with samples labeled ST-THN + ( ⁇ -Pr) 2 -BP, 75/25, ST-THN + ( ⁇ -Pr) 2 -BP, 50/50, ST- THN + ( ⁇ -Pr) 2 -BP, 25/75, and ST-THN + (i-
- Table 4 shows degradation results at a temperature of 667°F. It shows the results of (a) blending DOWTHERM RP heat transfer fluid, abbreviated as ST-THN, with (1) diisopropylbiphenyls ((i-Pr) 2 -BP) in the form of SURE SOL 330 ( Trademark of Koch Industries) fluid, and (2) mixtures of monoisopropylbiphenyls (i-Pr-BP) and diisopropylbiphenyls ((i-Pr) 2 -BP), in the form of SURE SOL 325 fluid, (3) 1 ,1- diphenylethane, abbreviated as 1,1 -DPE, some prepared in the laboratory, denoted as (SYN) and some of it obtained from Nisseki Chemical Texas Inc., and (b) degrading the blended fluid at 667°F.
- DOWTHERM RP heat transfer fluid abbreviated as ST-THN
- ST-THN DOWTHERM RP
- the resulting heat transfer fluid has superior thermal properties to the properties of a heat transfer fluid of either component used individually without the benefit of the second blended component.
- the blended heat transfer fluids further beneficially demonstrate a relatively minor formation of highers (heavy materials or residue).
- Table 4 also shows, in a similar indicative manner, thermal stability comparison results with respect to blends of 1,1-diphenylethane and DOWTHERM RP heat transfer fluid.
- the resulting heat transfer fluid has superior thermal properties to the properties of a heat transfer fluid of either component used individually without the benefit of the second blended component.
- the blends also demonstrate either very minor or essentially no formation of highers or residue.
- Table 5 shows that blends of triethylbiphenyl, as ThermSTM 800 heat transfer fluid from Nippon Steel Chemical Co., and DOWTHERM RP heat transfer fluid also have excellent thermal stability.
- examples of the invention are shown with samples labeled: ST-THN + DBT(N) (50-50); ST-THN + PHT (50-50); ((Et) 3 BP)+ ST-THN (75-25); ((Et) 3 BP)+ ST-THN (50-50); and ((Et) 3 BP)+ ST-THN (25-75).
- the blends demonstrate only minor formation of highers and only a small amount of residue.
- the blends show superior thermal properties to the properties of a heat transfer fluid of either component used individually without the benefit of the second blended component.
- Table 5 also shows that blends of diisopropylbiphenyls, as SURE SOL 330 fluid, and partially hydrogenated terphenyls also demonstrate superior thermal properties to the properties of a heat transfer fluid of either component used individually without the benefit of the second blended component
- the blended cases demonstrate low formation of lights, a very low formation of highers, and a lower formation of residue than demonstrated by either component used individually without the benefit of the second blended component
- dibenzyltoluene was degraded neat and as a blend with diisopropylbiphenyl, as SURE SOL 330, and showed no unusual improvements.
- the degradation of a blend of dibenzyltoluene and l,2,3,4-tetrahydro(l-phenylethyl)- naphthalene is also included for comparison.
- DOWTHERM* RP trademark of the Dow Chemical Company
- partially hydrogenated terphenyl was obtained as Therminol-66(trademark of Solutia) fluid
- dibenzyltoluene was obtained as Marlotherm SH(trademark of Huls) fluid
- diisopropylbiphenyl was obtained as Sure Sol-330 (trademark of Koch Chemical Company) fluid. It contained 90 percent diisopropylbiphenyl and 10 percent other alkylbiphenyls.
- the amount of gas was measured by weighing the degraded fluids in the vessel before and after opening the ampoules.
- Table 6 presents information in gas chromatographic analytical considerations.
- Carrier 1.4 mL/min, 10 psig head pressure
- the sample contained both cyclic styrene dimers and the linear dimer.
- the fluids were analyzed by the same method.
- the starting fluid was then analyzed by gas chromatography.
- the initial boiling point and final boiling point of the fluid are determined by calculating the cumulative area percent of the chromatogram.
- the initial boiling point is the boiling point of the component at 0.5 percent of the cumulative area
- the final boiling point is the boiling point of the component at 99.5 percent of the cumulative area. This determines the boiling range for the new fluid.
- the amount of light boiling products is the amount of components boiling between the initial boiling points of the new and degraded fluids.
- the amount of high boiling products is determined by measuring the area percent of components boiling between the final boiling points of the new and degraded fluids.
- the amount of nonvolatile decomposition products was done by heating 4 g of degraded sample in a ball-tube distillation apparatus slowly to 250°C at 1 mbar. The fluid was heated slowly to 230°C, held there for one hour, then heated to 250°C. and held there for 15 minutes.
- the amount of gaseous products was small, less than 0.5 percent of the total fluid.
- the total degradation measured for l,2,3,4-tetrahydro(l-phenylethyl)naphthalene was 5.7-6.5 percent, that for partially hydrogenated te ⁇ henyl was 9.4-10.3 percent, and 14.2 percent for dibenzyltoluene.
- the 50/50 blend of l,2,3,4-tetrahydro(l- phenylethyl)naphthalene and diisopropylbiphenyl(DIPBP) had a very low total degradation of only 3.4 percent, lower than that of either component fluid. It had no formation of high boiling components, and a low formation of nonvolatile decomposition products.
- the main degradation products were light boiling components. Table 8
- Test temperature 357°C, 675°F 357°C, 675°
- Nonvolatile decomposition products 0.04% (0.02, 0.04, 0.05) 0.04% (0.08, 0.01, 0.02)
- Test temperature 357°C, 675°F 357°C, 675°F
- Nonvolatile decomposition products 1.29% (1.12, 1.35, 1.39) 1.09% (1.05, 1.13. 1.08)
- Test temperature 357°C, 675°F
- Nonvolatile decomposition products 2.77 % (2.58, 2.96)
- Test temperature 357°C, 675°F
- Nonvolatile decomposition products 2.72 % (2.60, 2.84)
- Test temperature 357°C, 675°F
- Nonvolatile decomposition products 0.03 % (0.01, 0.02. 0.07) Total degree of decomposition: 3.4%
- Fluid B partially hydrogenated te ⁇ henyl
- Fluid D diisopropylbiphenyl fluid
- Fluid E a 50/50 blend of l ,2,3,4-tetrahydro(l-phenylethyl)naphthalene and di i sopropylbiphenyl
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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CA002399837A CA2399837A1 (en) | 2000-02-11 | 2001-01-24 | Thermal fluid blends containing 1,2,3,4-tetrahydro(1-phenylethyl)naphthalene |
MXPA02007770A MXPA02007770A (en) | 2000-02-11 | 2001-01-24 | Thermal fluid blends containing 1,2,3,4 tetrahydro(1 phenylethyl)naphthalene. |
EP01903363A EP1261677A1 (en) | 2000-02-11 | 2001-01-24 | Thermal fluid blends containing 1, 2, 3, 4-tetrahydro(1-phenylethyl)naphthalene |
AU2001231191A AU2001231191A1 (en) | 2000-02-11 | 2001-01-24 | Thermal fluid blends containing 1,2,3,4-tetrahydro(1-phenylethyl)naphthalene |
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US18188800P | 2000-02-11 | 2000-02-11 | |
US60/181,888 | 2000-02-11 |
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EP (1) | EP1261677A1 (en) |
KR (1) | KR20030011770A (en) |
AU (1) | AU2001231191A1 (en) |
CA (1) | CA2399837A1 (en) |
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KR100856959B1 (en) | 2001-04-11 | 2008-09-04 | 솔루티아인코포레이티드 | Process for the manufacture of temperature sensitive polymers |
WO2015177000A1 (en) * | 2014-05-21 | 2015-11-26 | Wacker Chemie Ag | Method for operating a system using siloxane high-temperature fluid |
CN113913164A (en) * | 2020-07-09 | 2022-01-11 | 中国石油化工股份有限公司 | High-temperature heat conduction oil and preparation method thereof |
Citations (1)
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WO1998050483A1 (en) * | 1997-05-09 | 1998-11-12 | The Dow Chemical Company | Thermal fluid blends containing 1,2,3,4-tetrahydro(1-phenylethyl)naphthalene |
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2001
- 2001-01-24 CA CA002399837A patent/CA2399837A1/en not_active Abandoned
- 2001-01-24 KR KR1020027010319A patent/KR20030011770A/en not_active Application Discontinuation
- 2001-01-24 EP EP01903363A patent/EP1261677A1/en not_active Withdrawn
- 2001-01-24 AU AU2001231191A patent/AU2001231191A1/en not_active Abandoned
- 2001-01-24 MX MXPA02007770A patent/MXPA02007770A/en not_active Application Discontinuation
- 2001-01-24 WO PCT/US2001/002676 patent/WO2001059029A1/en not_active Application Discontinuation
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WO1998050483A1 (en) * | 1997-05-09 | 1998-11-12 | The Dow Chemical Company | Thermal fluid blends containing 1,2,3,4-tetrahydro(1-phenylethyl)naphthalene |
Non-Patent Citations (1)
Title |
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MATSUMOTO TADASHI ET AL: "THERMAL TRANSFER FLUID: 1-PHENYL-1-TETRAHYDRONAPHTHYLETHANE", INDUSTRIAL AND ENGINEERING CHEMISTRY, PROCESS DESIGN AND DEVELOPMENT,AMERICAN CHEMICAL SOCIETY. WASHINGTON,US, vol. 3, no. 15, 1 September 1976 (1976-09-01), pages 215 - 218, XP002075987 * |
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KR100856959B1 (en) | 2001-04-11 | 2008-09-04 | 솔루티아인코포레이티드 | Process for the manufacture of temperature sensitive polymers |
WO2015177000A1 (en) * | 2014-05-21 | 2015-11-26 | Wacker Chemie Ag | Method for operating a system using siloxane high-temperature fluid |
CN113913164A (en) * | 2020-07-09 | 2022-01-11 | 中国石油化工股份有限公司 | High-temperature heat conduction oil and preparation method thereof |
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EP1261677A1 (en) | 2002-12-04 |
KR20030011770A (en) | 2003-02-11 |
MXPA02007770A (en) | 2004-09-10 |
AU2001231191A1 (en) | 2001-08-20 |
CA2399837A1 (en) | 2001-08-16 |
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