JPH01308482A - Heat transfer oil - Google Patents
Heat transfer oilInfo
- Publication number
- JPH01308482A JPH01308482A JP63138971A JP13897188A JPH01308482A JP H01308482 A JPH01308482 A JP H01308482A JP 63138971 A JP63138971 A JP 63138971A JP 13897188 A JP13897188 A JP 13897188A JP H01308482 A JPH01308482 A JP H01308482A
- Authority
- JP
- Japan
- Prior art keywords
- oil
- base oil
- heat transfer
- hydrogenated
- 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
- 238000012546 transfer Methods 0.000 title claims abstract description 29
- 239000003921 oil Substances 0.000 claims abstract description 97
- 239000002199 base oil Substances 0.000 claims abstract description 54
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000004508 fractional distillation Methods 0.000 claims abstract description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 8
- 239000011707 mineral Substances 0.000 claims abstract description 8
- 239000003245 coal Substances 0.000 claims description 18
- 239000011269 tar Substances 0.000 claims description 17
- WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 claims description 8
- 235000006173 Larrea tridentata Nutrition 0.000 claims description 7
- 244000073231 Larrea tridentata Species 0.000 claims description 7
- 229960002126 creosote Drugs 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 239000002641 tar oil Substances 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 9
- 239000003575 carbonaceous material Substances 0.000 abstract description 8
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- PLLCCSYEGQDAIW-UHFFFAOYSA-N 5-ethyl-1,6-dimethyl-5-phenylcyclohexa-1,3-diene Chemical compound C=1C=CC=CC=1C1(CC)C=CC=C(C)C1C PLLCCSYEGQDAIW-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002518 antifoaming agent Substances 0.000 abstract description 2
- 229910000480 nickel oxide Inorganic materials 0.000 abstract description 2
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011280 coal tar Substances 0.000 abstract 2
- 239000000470 constituent Substances 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 238000002474 experimental method Methods 0.000 description 11
- 150000002431 hydrogen Chemical class 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 150000004678 hydrides Chemical class 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- -1 alkylnaphthalene Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetraline Natural products C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BDCIZVMGTWOOIY-UHFFFAOYSA-N 1,10-dihydroanthracene Chemical compound C1=CC=C2C=C3CC=CC=C3CC2=C1 BDCIZVMGTWOOIY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 229910001120 nichrome Inorganic materials 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- PJDWNSYGMXODTB-UHFFFAOYSA-N 1,2,3,4,4a,4b,5,6-octahydrophenanthrene Chemical compound C1=CCCC2C(CCCC3)C3=CC=C21 PJDWNSYGMXODTB-UHFFFAOYSA-N 0.000 description 1
- VTIBBOHXBURHMD-UHFFFAOYSA-N 1,2,3,4,4a,5,10,10a-octahydroanthracene Chemical compound C1=CCC2CC(CCCC3)C3=CC2=C1 VTIBBOHXBURHMD-UHFFFAOYSA-N 0.000 description 1
- PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 0.000 description 1
- UXNCDAQNSQBHEN-UHFFFAOYSA-N 1,2,3,4-tetrahydrophenanthrene Chemical compound C1=CC2=CC=CC=C2C2=C1CCCC2 UXNCDAQNSQBHEN-UHFFFAOYSA-N 0.000 description 1
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 1
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
- UMKXSOXZAXIOPJ-UHFFFAOYSA-N 5,6,7,8-tetrahydro-2-naphthol Chemical compound C1CCCC2=CC(O)=CC=C21 UMKXSOXZAXIOPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- GWWAIWVRXPPMOU-UHFFFAOYSA-N [Li].[Pt] Chemical compound [Li].[Pt] GWWAIWVRXPPMOU-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 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
- 239000002270 dispersing agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- PXXKQOPKNFECSZ-UHFFFAOYSA-N platinum rhodium Chemical compound [Rh].[Pt] PXXKQOPKNFECSZ-UHFFFAOYSA-N 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は熱媒体油に関し、詳しくは高温で使用される際
の炭素質の生成が少ない熱媒体油に関する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a heat transfer oil, and more particularly to a heat transfer oil that produces less carbonaceous material when used at high temperatures.
従来の技術
熱媒体油は、間接加熱方式の熱媒体として最も一般的に
使用されている。この熱媒体油の要求性能としては、（
１）熱安定性がよく、高温での長時間使用に耐えること
、（２）比重、粘度、熱伝導度、蒸気圧などの物性値に
問題のないこと、（３）毒性のないこと、（４）腐食性
のないことなどがある。BACKGROUND OF THE INVENTION Heat transfer oil is most commonly used as a heat transfer medium in indirect heating systems. The required performance of this heat transfer oil is (
1) It has good thermal stability and can withstand long-term use at high temperatures; (2) it has no problems with physical properties such as specific gravity, viscosity, thermal conductivity, and vapor pressure; (3) it is non-toxic; 4) It is non-corrosive.
現在、精製鉱油をはじめジフェニル、ジフェニルエーテ
ル、アルキルベンゼン、アルキルナフタレン、１−フェ
ニル−１−キシリルエタンなどが熱媒体油として広く用
いられている。しかし、熱媒体油は一般に高温で使用さ
れるため、長時間使用すると油が劣化し、炭素質が生成
し、これがスラッジ生成の原因となっている。したがっ
て、高温における熱劣化が少なく、炭素質の生成のない
熱媒体油の開発は重要課題となりつつある。Currently, purified mineral oil, diphenyl, diphenyl ether, alkylbenzene, alkylnaphthalene, 1-phenyl-1-xylylethane, and the like are widely used as heat transfer oils. However, heat transfer oil is generally used at high temperatures, so when used for a long time, the oil deteriorates and carbonaceous substances are produced, which causes sludge formation. Therefore, the development of heat transfer oil that exhibits less thermal deterioration at high temperatures and does not generate carbonaceous matter is becoming an important issue.
一方、水素供与性物質の存在は古くから知られており、
石炭液化あるいは重質油分解、ビスブレーキング等にし
ばしば使用されている。水素供与性物質として最も代表
的なものはテトラリン（テトラヒドロナフタレン）であ
るが２環以上の芳香環を有するか芳香環−環と五員環１
個とをともに有する化合物の水素化物が水素供与性を有
することはすでに公知である。On the other hand, the existence of hydrogen-donating substances has been known for a long time.
It is often used for coal liquefaction, heavy oil cracking, visbreaking, etc. The most typical hydrogen-donating substance is tetralin (tetrahydronaphthalene), which has two or more aromatic rings or an aromatic ring and a five-membered ring.
It is already known that a hydride of a compound having both of
発明が解決しようとする課題
しかし、これらの水素供与性物質を熱媒体油使用時にお
ける炭素質１成防止に適用しようという試みはなく、ま
たそのような目的の実験報告もない。本発明者は石炭液
化および重質油分解など分子量の減少を伴なう操作にお
ける炭素質生成機構も熱媒体油使用時における炭素質生
成機構も本質的には同一であることに着目し、熱媒体油
使用時における炭素質生成に対して水素供与性物質の存
在が有効であることを実験により見出し、本発明を完成
するに至った。Problems to be Solved by the Invention However, there has been no attempt to apply these hydrogen-donating substances to the prevention of carbonaceous formation when heat transfer oil is used, nor have there been any experimental reports for such purpose. The present inventor focused on the fact that the carbonaceous production mechanism in operations that involve a reduction in molecular weight, such as coal liquefaction and heavy oil cracking, and the carbonaceous production mechanism in the use of heat transfer oil, are essentially the same. Through experiments, the present inventors discovered that the presence of a hydrogen-donating substance is effective for carbonaceous production when using medium oil, and have completed the present invention.
本発明は、高温使用時において炭素質生成の少ない熱媒
体油を提供することを目的とする。An object of the present invention is to provide a heat transfer oil that generates less carbonaceous material during high-temperature use.
課題を解決するための手段
本発明は、
（ｉ）鉱油系基油及び／または合成系基油１００重量部
に対して、必須成分として、
（ｉｆ）石炭系タールまたはこれを分留して得られる油
を水素化し、３５０℃以上での水素供与性が前記鉱油系
基油及び／または合成系基油の３倍以上である水素化油
０，１〜２０重量部を添加してなる熱媒体油を提供する
ものである。Means for Solving the Problems The present invention provides (i) based on 100 parts by weight of mineral oil base oil and/or synthetic base oil, (if) coal-based tar or obtained by fractional distillation thereof. A heating medium obtained by hydrogenating an oil and adding 0.1 to 20 parts by weight of a hydrogenated oil whose hydrogen donating property at 350°C or higher is three times or more that of the mineral base oil and/or synthetic base oil. It provides oil.
以下、本発明の内容をより詳細に説明する。Hereinafter, the content of the present invention will be explained in more detail.
本発明の鉱油系基油および合成系基油としては、−膜内
に潤滑油として使用されている油と同程度の粘度を有す
る油であれば何を使用してもよい。As the mineral base oil and the synthetic base oil of the present invention, any oil having a viscosity comparable to that of the oil used as a lubricating oil in the membrane may be used.
鉱油系基油としては、具体的には、たとえば、７０ペー
ル油、ＳＡＥ １０．５ＡＥ２０．５ＡＥ３０．５ＡＥ
５０、ブライトストック等の各種グレードのものが使用
される。Specifically, the mineral base oil includes, for example, 70 pale oil, SAE 10.5AE20.5AE30.5AE
Various grades such as 50 and bright stock are used.
また合成系基油としては、具体的には例えばポリブテン
、α−オレフィンオリゴマー、アルキルベンゼン、アル
キルナフタレン、ジエステル、ポリオールエステル、ポ
リグリコール、ポリフェニルエーテル、トリクレジルホ
スフェート、シリコーン油、パーフルオロアルキルエー
テル、ノルマルパラフィン、ジフェニルアルカンなどが
使用される。Specific examples of synthetic base oils include polybutene, α-olefin oligomer, alkylbenzene, alkylnaphthalene, diester, polyol ester, polyglycol, polyphenyl ether, tricresyl phosphate, silicone oil, perfluoroalkyl ether, Normal paraffin, diphenylalkane, etc. are used.
これらの中でジフェニルアルカンの一種である、式
で表される、１−フェニル−１−キシリルエタンは、特
に好ましく使用される。Among these, 1-phenyl-1-xylylethane, which is a type of diphenylalkane and is represented by the formula, is particularly preferably used.
本発明において基油に添加される水素化油は基油に対し
て水素供与性が優れていなければならない。そして高温
下で基油から炭素質物資が生成するかあるいは高分子物
質が生成するような条件下で水素を供与する物質でなけ
ればならない。また、一方、基油は熱媒体油それぞれの
用途に合致した性状のものが選ばれる。基油に対して加
えられる水素化油が多いと基油が本来有している性質が
損われ、熱媒体油としての性能が失われる。したがって
、基油に対して添加される水素化油の量は少なくて効果
のあるものが好ましい。実用的な見地から基油に添加さ
れる水素化油の量は基油１００重量部に対して０．１〜
２０重量部であることが必要であり、好ましくは１〜１
５重量部、更に好ましくは２〜１０重量部である。また
、この場合、基油に対して加えられる水素化油の水素供
与性は基油の３倍以上、好ましくは５倍以上、−さらに
好ましくは１０倍以上であることが必要である。本発明
者は、前述の条件を満たす水素化油として、石炭系ター
ルまたはこれを分留して得られる油を水素化した水素化
油が有効であることを見出した。In the present invention, the hydrogenated oil added to the base oil must have excellent hydrogen donating properties to the base oil. It must be a substance that donates hydrogen under conditions such that carbonaceous substances or polymeric substances are generated from the base oil at high temperatures. On the other hand, the base oil is selected to have properties that match the use of each heat transfer oil. If too much hydrogenated oil is added to the base oil, the inherent properties of the base oil will be impaired and the performance as a heat transfer oil will be lost. Therefore, it is preferable that the amount of hydrogenated oil added to the base oil is small and effective. From a practical standpoint, the amount of hydrogenated oil added to base oil is 0.1 to 100 parts by weight of base oil.
It is necessary that the amount is 20 parts by weight, preferably 1 to 1
The amount is 5 parts by weight, more preferably 2 to 10 parts by weight. Further, in this case, the hydrogen donating property of the hydrogenated oil added to the base oil needs to be at least 3 times, preferably at least 5 times, and more preferably at least 10 times that of the base oil. The present inventors have found that hydrogenated oil obtained by hydrogenating coal-based tar or oil obtained by fractional distillation of coal-based tar is effective as a hydrogenated oil that satisfies the above-mentioned conditions.
この石炭系タールまたはこれを分留して得られる油は、
２環以上の芳香環を有する化合物および芳香環−環と不
飽和五員環１個とをともに有する化合物を多く含有し、
これを水素化することにより水素供与性を有するように
なる。通常基油にも前記多環の芳香族化合物が含まれる
ことが知られているが、良好な水素供与性を有する化合
物の含有量は極めて少なく、基油の水素供与性が極めて
低いことは実験により確かめられている。前記石炭系タ
ールまたはこれを分留して得られる油としては、洗浄油
、アントラセン油、タール油、タール軽油、カルボール
油、ナフタレン油、ピッチ油、クレオソート油、石炭液
化油またはこれらの混合物が例示される
前記石炭系タールまたはこれを分留して得られる油の水
素化方法は任意であるが、通常水素化機能を有する触媒
の存在下で水素ガスにより水素化する方法が用いられる
。水素化機能を有する触媒としては、特に制限はなく、
石油留分の水素化処理に用いる公知の触媒が使用できる
。具体的には、周期律表第Ｖ〜■族から選ばれた少なく
とも一種の金属元素、特にニッケル、コバルト、モリブ
デン、バナジウムおよびタングステンから選ばれる少な
くとも一種の金属元素の硫化物、酸化物等をアルミナ、
シリカ、シリカ舎アルミナ、カチオン置換ゼオライト等
の無機質担体に担持させたものあるいは芳香環核水素化
触媒、例えばニッケル、酸化ニッケル、ニッケルー銅、
白金、酸化白金、白金−ロジウム、白金−リチウム、ロ
ジウム、パラジウム、コバルト、ラネーコバルト、ルテ
ニウム等の金属を活性炭、アルミナ、シリカ−アルミナ
、けいそう土およびゼオライト等の無機質担体に担持さ
せたものが例示される。原料油をこれらの水素化機能を
有する触媒の存在下で水素化する際の条件は、前記石油
留分の水素化処理に用いられる触媒の場合には３００℃
〜４００℃、３０気圧〜１５０気圧であることが好まし
く、また芳香環核水素化触媒の場合には１５０℃〜３０
０℃、３０気圧〜１５０気圧であることが望ましい。反
応装置についてもとくに制限はなく、一般の固定床反応
装置を使用することによって良好な水素供与性を有する
水素化油を調製することができる。This coal-based tar or the oil obtained by fractionating it is
Contains many compounds having two or more aromatic rings and compounds having both an aromatic ring and one unsaturated five-membered ring,
By hydrogenating this, it becomes capable of donating hydrogen. It is known that normal base oils also contain the above-mentioned polycyclic aromatic compounds, but the content of compounds with good hydrogen donating properties is extremely small, and it has been experimentally proven that the hydrogen donating properties of base oils are extremely low. It has been confirmed by. The coal-based tar or the oil obtained by fractional distillation thereof includes washing oil, anthracene oil, tar oil, tar light oil, carbol oil, naphthalene oil, pitch oil, creosote oil, coal liquefied oil, or a mixture thereof. Any method may be used to hydrogenate the coal-based tar or the oil obtained by fractionating it, but a method of hydrogenating with hydrogen gas in the presence of a catalyst having a hydrogenation function is usually used. There are no particular restrictions on the catalyst that has a hydrogenation function.
Known catalysts used for hydrotreating petroleum fractions can be used. Specifically, the sulfide, oxide, etc. of at least one metal element selected from Groups V to II of the periodic table, especially at least one metal element selected from nickel, cobalt, molybdenum, vanadium, and tungsten, is used as alumina. ,
Those supported on inorganic supports such as silica, silica alumina, and cation-substituted zeolites, or aromatic ring hydrogenation catalysts such as nickel, nickel oxide, nickel-copper,
Metals such as platinum, platinum oxide, platinum-rhodium, platinum-lithium, rhodium, palladium, cobalt, Raney cobalt, and ruthenium are supported on inorganic carriers such as activated carbon, alumina, silica-alumina, diatomaceous earth, and zeolite. Illustrated. The conditions for hydrogenating feedstock oil in the presence of these catalysts having a hydrogenation function are 300°C in the case of catalysts used for hydrotreating petroleum fractions.
The temperature is preferably ~400°C and 30 atm to 150 atm, and in the case of an aromatic ring hydrogenation catalyst, the temperature is preferably 150°C to 30 atm.
The temperature is preferably 0°C and 30 to 150 atmospheres. There are no particular restrictions on the reactor, and a hydrogenated oil having good hydrogen-donating properties can be prepared by using a general fixed bed reactor.
かようにして得られた水素化油中には水素供与性物質と
して、具体的には例えば、ジヒドロナフタレン、テトラ
ヒドロナフタレン、ジヒドロアントラセン、ジヒドロフ
ェナントレン、テトラヒドロアントラセン、テトラヒド
ロフェナントレン、オクタヒドロアントラセン、オクタ
ヒドロフェナントレン、５，６，７．８−テトラヒドロ
−２−ナフトール、１，２．３．４−テトラヒドロキノ
リン等が含まれ、これらの物質を単体で使用することも
可能であるが、経済的見地から好ましくない。The thus obtained hydrogenated oil contains hydrogen-donating substances such as dihydronaphthalene, tetrahydronaphthalene, dihydroanthracene, dihydrophenanthrene, tetrahydroanthracene, tetrahydrophenanthrene, octahydroanthracene, and octahydrophenanthrene. , 5,6,7.8-tetrahydro-2-naphthol, 1,2.3.4-tetrahydroquinoline, etc. Although it is possible to use these substances alone, it is preferable from an economic standpoint. do not have.
本願において、これら炭化水素類の水素供与性を評価す
る方法は、以下の方法によって行う。これは、水素受容
体を用いて移行性水素の捕捉量から求める方法である。In the present application, the hydrogen donating properties of these hydrocarbons are evaluated by the following method. This is a method of calculating from the amount of captured migrating hydrogen using a hydrogen acceptor.
すなわち、試料とアントラセン等の水素受容体を一定条
件で反応させ、反応汲水素化された水素受容体の量をガ
スクロマトグラフィー等で分析する。That is, a sample and a hydrogen acceptor such as anthracene are reacted under certain conditions, and the amount of hydrogenated hydrogen acceptor is analyzed by gas chromatography or the like.
具体的には、所定量の炭化水素類試料およびアントラセ
ンを所定ｆｆ１（試料／アントラセン−１／２重量比）
撹拌器付きオートクレーブに収容し、３５０℃以上、た
とえば３５０℃〜４５０℃の温度、圧力５０ｋｇ／ｃｄ
・ｇ （Ｎ２圧）、無触媒で３０分間反応させる。反
応前後の９．１０−ジヒドロアントラセン、１，４，５
．８−テトラヒドロアントラセン、１，２，３．４−テ
トラヒドロアントラセン、１，２，３，４，５．６，７
．８−オクタヒドロアントラセンならびに残存アントラ
センの量をガスクロマトグラフィーで分析する。Specifically, predetermined amounts of a hydrocarbon sample and anthracene were mixed at a predetermined ff1 (sample/anthracene-1/2 weight ratio).
Stored in an autoclave with a stirrer, at a temperature of 350°C or higher, for example, 350°C to 450°C, and a pressure of 50 kg/cd.
・G (N2 pressure), react for 30 minutes without catalyst. 9.10-dihydroanthracene, 1,4,5 before and after reaction
．． 8-tetrahydroanthracene, 1,2,3.4-tetrahydroanthracene, 1,2,3,4,5.6,7
．． The amount of 8-octahydroanthracene and residual anthracene is analyzed by gas chromatography.
これらアントラセンの水素化物生成に使用される水素は
、水素供与性を有する炭化水素類から供給されるので、
これら炭化水素類からアントラセンに移行した水素の量
（水素原子／ＩＩｏｔアントラセン）を求め、これを水
素供与性として測定する。The hydrogen used to produce these anthracene hydrides is supplied from hydrocarbons that have hydrogen donating properties, so
The amount of hydrogen transferred from these hydrocarbons to anthracene (hydrogen atom/IIot anthracene) is determined and measured as hydrogen donating property.
なお、この方法は、Ｙｏｋｏｎｏ Ｔ、、Ｍａｒｓｈ
Ｈ，ａｎｄ Ｙｏｋｏｎｏ Ｍ、、Ｆｕｅ １
，６０，６０７ （１９８１）に記載されている方法に
準じたものである。This method is described by Yokono T., Marsh
H, and Yokono M,, Fue 1
, 60, 607 (1981).
このような物質を基油に加える方法としては製油所で基
油を製造する段階で加えることもできるし、熱媒体油を
使用する段階で使用者側で添加することも可能である。Such a substance can be added to the base oil at the stage of producing the base oil at a refinery, or it can be added by the user at the stage of using the heat transfer oil.
さらには、基油を製造する段階で、石炭系タールまたは
これを分留して得られる２環以上の芳香環を有するかま
たは一環の芳香環と一個の五員環とをともに有する化合
物を含有する油を基油とともに水素化し、基油を製造す
ると同時に水素化物を得ることも可能である。Furthermore, in the step of producing base oil, coal-based tar or a compound obtained by fractional distillation of the tar that has two or more aromatic rings or has both one aromatic ring and one five-membered ring is used. It is also possible to hydrogenate the oil together with the base oil to obtain the hydride at the same time as producing the base oil.
また、普通熱媒体油には各種添加剤を加えてその性能を
向上せしめる。本発明の熱媒体油に対して、このような
添加剤を加えることも何ら支障はない。このような添加
剤としては、たとえば酸化防止剤、清浄分散剤、粘度指
数向上剤、流動点降下剤、腐食防止剤、金属不活性剤、
さび止め剤、消泡剤、着色剤などが挙げられる。これら
各種添加剤の詳細は、例えば“潤滑油学界誌、第１５巻
、第６号”または“桜井俊男編著、「石油製品添加剤」
（幸書房）°などに記載されている。これら各種添加
剤の合計添加量は、基油１００重量部に対して１０ｆｆ
ｉ量部以下、好ましくは５ｆｒｆｆｉ部以下、特に好ま
しくは３重量部以下であるのが望ましい。Additionally, various additives are added to ordinary heat transfer oil to improve its performance. There is no problem in adding such additives to the heat transfer oil of the present invention. Such additives include, for example, antioxidants, detergent dispersants, viscosity index improvers, pour point depressants, corrosion inhibitors, metal deactivators,
Examples include rust inhibitors, antifoaming agents, and coloring agents. Details of these various additives can be found, for example, in "Lubricant Science Journal, Volume 15, No. 6" or "Petroleum Product Additives" edited by Toshio Sakurai.
(Saiwai Shobo) ° etc. The total amount of these various additives added is 10ff per 100 parts by weight of the base oil.
It is desirable that the amount is not more than i parts, preferably not more than 5 parts by weight, particularly preferably not more than 3 parts by weight.
実施例
本発明につき以下の実験、比較実験、実施例、比較例に
より更に詳細に説明する。EXAMPLES The present invention will be explained in more detail by the following experiments, comparative experiments, working examples, and comparative examples.
実験１〜３、比較実験１〜３
熱媒体油基油と水素化油の水素供与性を比較するために
次のような実験を行った。熱媒体油基油としでは、アラ
ビア系原油からの５ＡＥＩＯ１ＳＡＥ３０．５ＡＥ５０
（いずれも水素化精製したもの）を、水素化油の例と
してアントラセン油、クレオソート油およびナフタレン
油の水素化物を使用した。実験方法は前述の方法によっ
て行った。Experiments 1 to 3, Comparative Experiments 1 to 3 The following experiments were conducted to compare the hydrogen donating properties of heat transfer oil base oil and hydrogenated oil. Heat transfer oil base oil is 5AEIO1SAE30.5AE50 from Arabian crude oil.
(all of which were hydrorefined), and hydrogenated products of anthracene oil, creosote oil, and naphthalene oil were used as examples of hydrogenated oils. The experimental method was as described above.
すなわち、試料とアントラセンを一定条件で反応させ、
アントラセンに添加した水素の量から水素移行量を求め
る方法によった。In other words, the sample and anthracene are reacted under certain conditions,
The amount of hydrogen transferred was calculated from the amount of hydrogen added to anthracene.
前記５ＡＥ１０．５ＡＥ３０および５ＡＥ５０の基油を
アントラセンと一定条件（表１）で反応させ、反応後９
．１０−ジヒドロアントラセン、１．２．３．４−テト
ラヒドロアントラセンおよび１，２，３，４，５．６，
７．８−オクタヒドロアントラセンの量をガスクロマト
グラフィーで分析した。この結果、各基油からアントラ
センに移行した水素の量がわかる。結果を表３に示す。The above 5AE10.5AE30 and 5AE50 base oils were reacted with anthracene under certain conditions (Table 1), and after the reaction 9.
．． 10-dihydroanthracene, 1.2.3.4-tetrahydroanthracene and 1,2,3,4,5.6,
The amount of 7.8-octahydroanthracene was analyzed by gas chromatography. As a result, the amount of hydrogen transferred from each base oil to anthracene can be determined. The results are shown in Table 3.
一方、アントラセン油、クレオソート油およびナフタレ
ン油を一定条件（表２）で水素化した水素化物とアント
ラセンを表１の条件で反応させ、反応前後の９，１０−
ジヒドロアントラセン、１゜４．５．８−テトラヒドロ
アントラセン、１．２゜３．４−テトラヒドロアントラ
セン、１．２，３゜４．５．６，７．８−オクタヒドロ
アントラセンならびにアントラセンの量をガスクロマト
グラフィーで分析した。反応前後のこれらの増減を求め
、アントラセン油、クレオソート油およびナフタレン油
水素化物からアントラセンに移行した水素移行量（原子
／ｍｏｌアントラセン）を求めた。各基油からアントラ
センに移行した水素の量ならびにアントラセン油、クレ
オソート油およびナフタレン油の水素化物からアントラ
センに移行した水素の量をまとめて表３に示す。On the other hand, a hydride obtained by hydrogenating anthracene oil, creosote oil, and naphthalene oil under certain conditions (Table 2) was reacted with anthracene under the conditions shown in Table 1.
The amounts of dihydroanthracene, 1゜4.5.8-tetrahydroanthracene, 1.2゜3.4-tetrahydroanthracene, 1.2,3゜4.5.6,7.8-octahydroanthracene and anthracene are Analyzed by chromatography. These increases and decreases before and after the reaction were determined, and the amount of hydrogen transferred from anthracene oil, creosote oil, and naphthalene oil hydride to anthracene (atoms/mol anthracene) was determined. The amounts of hydrogen transferred from each base oil to anthracene and the amounts of hydrogen transferred to anthracene from the hydrides of anthracene oil, creosote oil, and naphthalene oil are summarized in Table 3.
この結果、各基油からの水素の移行量は非常に少なく、
一方、水素化油の例では水素の移行量はかなり大きく、
すなわち、水素供与性は各基油の３倍以上、たとえば１
０〜３０倍あることがわかる。As a result, the amount of hydrogen transferred from each base oil is very small.
On the other hand, in the case of hydrogenated oil, the amount of hydrogen transferred is quite large;
In other words, the hydrogen donating property is more than three times that of each base oil, for example, 1
It can be seen that there are 0 to 30 times more.
表１．水素供与性の実験条件
表２．アントラセン油、クレオソート油およびナフタレ
ン油
の水素化条件
３、水素移行量の実験結果
実施例１、比較例１
、 内容積１００−の内部撹拌型オートクレーブ実験装
置により比較例１では比較実験３に示した５ＡＥ５０基
油、実施例１では同じ５ＡＥ５０基油１００重量部に、
実験１に示した水素化アントラセン油５重量部を加えた
ものを各々上記オートクレーブに入れ、４００℃で７２
時間、内部の撹拌を継続した。なお、気相は窒素で初圧
５ ｋｇ ／ ｃｊ（常温）で加圧してから昇温した。Table 1. Hydrogen donating experimental conditions table 2. Hydrogenation conditions 3 of anthracene oil, creosote oil and naphthalene oil, experimental results of hydrogen transfer amount Example 1, Comparative Example 1 Comparative Example 1 and Comparative Experiment 3 using an internal stirring type autoclave experimental apparatus with an internal volume of 100 5AE50 base oil, in Example 1, 100 parts by weight of the same 5AE50 base oil,
Add 5 parts by weight of the hydrogenated anthracene oil shown in Experiment 1 to each of the above autoclaves, and heat at 400°C for 72 hours.
Internal stirring was continued for an hour. The gas phase was pressurized with nitrogen at an initial pressure of 5 kg/cj (at room temperature) and then heated.
７２時間経過後内容物を取り出し炭素質の生成を観察し
、次いでトルエン不溶分を測定した。結果を表４に示し
た。After 72 hours, the contents were taken out and the formation of carbonaceous matter was observed, and then the toluene insoluble content was measured. The results are shown in Table 4.
実施例２、比較例２
図に示す内部密閉型恒温槽（ステンレス製）中に、比較
例２では比較実験２に示した５ＡＥ３０基油、実施例２
では同じ５ＡＥ３０基油１００重量部に、実験２に示し
た水素化クレオソート油７重量部を加えたものをそれぞ
れ上記内部密閉型恒温槽に入れた。いずれの場合も表面
温度約８００℃のニクロム線を液中に浸し、液は撹拌し
、液の温度は２００℃に保持するよう恒温槽を加熱した
。Example 2, Comparative Example 2 In Comparative Example 2, the 5AE30 base oil shown in Comparative Experiment 2 and Example 2 were placed in an internally sealed constant temperature oven (made of stainless steel) shown in the figure.
Now, 100 parts by weight of the same 5AE30 base oil and 7 parts by weight of the hydrogenated creosote oil shown in Experiment 2 were added to each of the above-mentioned internally sealed thermostats. In each case, a nichrome wire with a surface temperature of about 800°C was immersed in the liquid, the liquid was stirred, and a constant temperature bath was heated to maintain the temperature of the liquid at 200°C.
また、気相は窒素で置換した。この状態を１．５００時
間継続したのち、液のサンプリングを行い、液中の炭素
質の生成を観察し、次いでトルエン不溶分を測定した。In addition, the gas phase was replaced with nitrogen. After this state was continued for 1,500 hours, the liquid was sampled to observe the formation of carbonaceous substances in the liquid, and then toluene insoluble matter was measured.
この結果も表４に示した。The results are also shown in Table 4.
表４ 以上の各実施例から次の点が明らかである。Table 4 The following points are clear from each of the above embodiments.
（１）熱媒体油基油の水素供与性は小さい。(1) The hydrogen donating property of the heat transfer oil base oil is small.
（２）石炭系タールから得られた製品の水素化物の水素
供与性は熱媒体油基油に比較して非常に大きい。(2) The hydrogen donating property of the hydride product obtained from coal-based tar is much greater than that of heat transfer oil base oil.
（３）熱媒体油基油に上記石炭系タールから得られた製
品の水素化物を加えると炭素質の生成が大巾に減少する
。(3) When a hydride of the product obtained from the coal-based tar is added to the heat transfer oil base oil, the formation of carbonaceous substances is greatly reduced.
（４）上記石炭系タールから得られた製品の水素化物は
多くは必要とせず、上記の例では数％で十分効果が発揮
される。(4) A large amount of the hydride of the product obtained from the coal-based tar is not required, and in the above example, a few percent is sufficient to exhibit the effect.
発明の効果
以上のように、石炭系タールまたはこれを分留して得ら
れた油のうち所定の水素供与性を有するものを熱媒体油
に少量加えることによって、熱媒体油使用時における炭
素質の析出が制限され、しかも基油の有する性状を損う
ことなく使用されることがわかる。Effects of the Invention As described above, by adding a small amount of coal-based tar or oil obtained by fractional distillation of coal-based tar, which has a certain hydrogen donating property, to heat transfer oil, carbonaceous material can be reduced when using heat transfer oil. It can be seen that the precipitation of the base oil is restricted and that it can be used without impairing the properties of the base oil.
図は、本発明の実施例において用いる試験装置を示す略
示図である。
（１）ニステンレス製恒温槽、（−２）：撹拌装置、（
３）二ニクロム線、 （４）：温度計。
特許出願人 日本石油株式会社The figure is a schematic diagram showing a test apparatus used in an example of the present invention. (1) Nissin stainless steel constant temperature bath, (-2): Stirring device, (
3) Nichrome wire, (4): Thermometer. Patent applicant Nippon Oil Co., Ltd.
Claims (1)
に対して、必須成分として、 （ｉｉ）石炭系タールまたはこれを分留して得られる油
を水素化し、３５０℃以上での水素供与性が前記鉱油系
基油及び／または合成系基油の３倍以上である水素化油
０．１〜２０重量部 を添加してなる熱媒体油。 〔２〕前記石炭系タールまたはこれを分留して得られる
油が、洗浄油、アントラセン油、タール油、タール軽油
、カルボール油、ナフタレン油、ピッチ油、クレオソー
ト油、石炭液化油またはこれらの混合物である請求項１
に記載の熱媒体油。[Scope of Claims] [1] (i) Based on 100 parts by weight of mineral base oil and/or synthetic base oil, (ii) coal-based tar or oil obtained by fractional distillation thereof; A heat transfer oil obtained by hydrogenating and adding 0.1 to 20 parts by weight of a hydrogenated oil whose hydrogen donating property at 350° C. or higher is three times or more that of the mineral base oil and/or synthetic base oil. [2] The coal-based tar or the oil obtained by fractional distillation thereof may be a cleaning oil, anthracene oil, tar oil, tar light oil, carbol oil, naphthalene oil, pitch oil, creosote oil, coal liquefied oil or any of these. Claim 1: It is a mixture.
The heating medium oil described in .
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63138971A JPH01308482A (en) | 1988-06-06 | 1988-06-06 | Heat transfer oil |
| DE89105829T DE68911356T2 (en) | 1988-04-05 | 1989-04-03 | Oil composition containing hydrogenated oil. |
| EP89105829A EP0338311B1 (en) | 1988-04-05 | 1989-04-03 | Oil composition containing hydrogenated oil |
| CA000595637A CA1327787C (en) | 1988-04-05 | 1989-04-04 | Oil composition containing hydrogenated oil |
| US07/333,706 US5015404A (en) | 1988-04-05 | 1989-04-05 | Oil composition containing hydrogenated oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63138971A JPH01308482A (en) | 1988-06-06 | 1988-06-06 | Heat transfer oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01308482A true JPH01308482A (en) | 1989-12-13 |
| JPH0573796B2 JPH0573796B2 (en) | 1993-10-15 |
Family
ID=15234456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63138971A Granted JPH01308482A (en) | 1988-04-05 | 1988-06-06 | Heat transfer oil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01308482A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4740388B1 (en) * | 2010-08-20 | 2011-08-03 | 株式会社タクトテクノロジ | Heat medium, heat exchange system, and heat storage body |
-
1988
- 1988-06-06 JP JP63138971A patent/JPH01308482A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4740388B1 (en) * | 2010-08-20 | 2011-08-03 | 株式会社タクトテクノロジ | Heat medium, heat exchange system, and heat storage body |
| JP2012041477A (en) * | 2010-08-20 | 2012-03-01 | Takuto Technology:Kk | Heating medium, heat exchange system, and heat storage body |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0573796B2 (en) | 1993-10-15 |
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