JPH0414717B2 - - Google Patents
Info
- Publication number
- JPH0414717B2 JPH0414717B2 JP59249772A JP24977284A JPH0414717B2 JP H0414717 B2 JPH0414717 B2 JP H0414717B2 JP 59249772 A JP59249772 A JP 59249772A JP 24977284 A JP24977284 A JP 24977284A JP H0414717 B2 JPH0414717 B2 JP H0414717B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- heat transfer
- present
- naphthalene
- monoalkylnaphthalene
- 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.)
- Expired - Lifetime
Links
- 238000012546 transfer Methods 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- -1 allyl alkane Chemical class 0.000 description 36
- 239000003921 oil Substances 0.000 description 27
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 16
- 230000003647 oxidation Effects 0.000 description 16
- 238000007254 oxidation reaction Methods 0.000 description 16
- 238000012360 testing method Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- YLZQHQUVNZVGOK-UHFFFAOYSA-N 2-methylnon-1-ene Chemical compound CCCCCCCC(C)=C YLZQHQUVNZVGOK-UHFFFAOYSA-N 0.000 description 3
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- CMMITBUEUSCFJC-UHFFFAOYSA-N 2-(2-methylundecan-2-yl)naphthalene Chemical compound C1=CC=CC2=CC(C(C)(C)CCCCCCCCC)=CC=C21 CMMITBUEUSCFJC-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 description 1
- PVAPJEBDTSVWFD-UHFFFAOYSA-N 2-(2-methylheptan-2-yl)naphthalene Chemical compound C1=CC=CC2=CC(C(C)(C)CCCCC)=CC=C21 PVAPJEBDTSVWFD-UHFFFAOYSA-N 0.000 description 1
- WEPURZXXOSBDLV-UHFFFAOYSA-N 2-(2-methylnonan-2-yl)naphthalene Chemical compound C1=CC=CC2=CC(C(C)(C)CCCCCCC)=CC=C21 WEPURZXXOSBDLV-UHFFFAOYSA-N 0.000 description 1
- RCBGGJURENJHKV-UHFFFAOYSA-N 2-methylhept-1-ene Chemical compound CCCCCC(C)=C RCBGGJURENJHKV-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 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
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000005377 tertiary alkyl halides Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Description
（発明の技術分野）
本発明は新規な熱媒体油に関し、さらに詳しく
は特定の構造を有するモノアルキルナフタレン混
合物からなる、酸化安定性に特に優れた新規な熱
媒体油に関する。
（発明の背景）
最近の化学工業における技術の進歩は著しいも
のがあり、加熱方式においても直接加熱方式に代
わり、熱媒体として油などを用いる間接加熱方式
が繊維、製紙、食品、建築、化学などのあらゆる
産業分野で広範囲に用いられている。
この間接加熱方式の熱媒体としては熱媒体油が
最も一般的に使用されており、この熱媒体は通
常、
(1) 熱安定性に優れている、
(2) 蒸気圧が低く、引火点が高い、
(3) 低温流動性がよい、
(4) 毒性、臭気がない、
(5) 加熱効率がよい、
といつた性状を持つことが要求され、現在では酸
化防止剤を添加した高度精製鉱油をはじめ、フエ
ニルエーテル、ポリフエニル、アリルアルカン、
メチル基、エチル基、プロピル基などを有するア
ルキルナフタレンなどが熱媒体油として広く用い
られている。
この中でアルキルナフタレン系の熱媒体油は毒
性がなく、低粘度、低沸点、高沸点という熱媒体
油としての好ましい条件を兼ね備えたものである
が、その酸化安定性はまだ満足できるものでなか
つた。
本発明者らはアルキルナフタレン系の熱媒体油
に着目し、より高い酸化安定性を有するナフタレ
ン系熱媒体油を開発すべく研究を重ねた結果、特
定の構造を有するモノアルキルナフタレンからな
る熱媒体油が公知のアルキルナフタレン系熱媒体
油と比較して格段に高い酸化安定性を有すること
を見い出し、本発明を完成するに至つた。
（発明の目的）
本発明は特に酸化安定性に優れた熱媒体油を提
供することを目的とする。
（本発明の構成）
本発明の熱媒体油は、一般式
（式中、R1、R2およびR3はそれぞれ炭素数１〜
21のアルキル基であり、かつR1、R2およびR3の
合計炭素数は５〜23である）で表わされるモノア
ルキルナフタレンからなることを特徴とする。
以下、本発明の内容をより詳細に説明する。
本発明の熱媒体油であるアルキルナフタレン
は、
モノアルキルナフタレンであること、
一般式
(Technical Field of the Invention) The present invention relates to a novel heat transfer oil, and more particularly to a new heat transfer oil that is composed of a monoalkylnaphthalene mixture having a specific structure and has particularly excellent oxidation stability. (Background of the invention) Recent advances in technology in the chemical industry have been remarkable, and indirect heating methods that use oil as a heating medium have replaced direct heating methods in textiles, paper manufacturing, food, architecture, chemicals, etc. It is widely used in all industrial fields. The most commonly used heat medium for this indirect heating method is heat transfer oil, which typically has the following characteristics: (1) excellent thermal stability, (2) low vapor pressure, and low flash point. (3) good low-temperature fluidity, (4) no toxicity or odor, and (5) good heating efficiency.Currently, highly refined mineral oils with added antioxidants are required. Including phenyl ether, polyphenyl, allyl alkane,
Alkylnaphthalenes having methyl groups, ethyl groups, propyl groups, etc. are widely used as heat transfer oils. Among these, alkylnaphthalene-based heat transfer oils are non-toxic and have desirable conditions as heat transfer oils such as low viscosity, low boiling point, and high boiling point, but their oxidation stability is still unsatisfactory. Ta. The present inventors focused on alkylnaphthalene-based heat transfer oil, and as a result of repeated research to develop a naphthalene-based heat transfer oil with higher oxidation stability, the inventors found that a heat transfer medium made of monoalkylnaphthalene with a specific structure The present inventors have discovered that the oil has much higher oxidation stability than known alkylnaphthalene heat transfer oils, and have completed the present invention. (Object of the Invention) An object of the present invention is to provide a heat transfer oil having particularly excellent oxidation stability. (Structure of the present invention) The heat transfer oil of the present invention has the general formula (In the formula, R 1 , R 2 and R 3 each have 1 to 1 carbon atoms.
21 alkyl groups, and the total carbon number of R 1 , R 2 and R 3 is 5 to 23). Hereinafter, the content of the present invention will be explained in more detail. The alkylnaphthalene which is the heat transfer oil of the present invention is a monoalkylnaphthalene, and has the following general formula:
【式】で表わされるアルキル基
のR1、R2およびR3の合計炭素数が５〜23であ
ること、
ナフタレン環に直接結合するアルキル基が第
３級アルキル基であること、
の３点を満たすものであることが必要である。上
記３点のうちどれか１点でも要件を満たしていな
いアルキルナフタレンでは、本発明のアルキルナ
フタレンと比べて酸化安定性や熱媒体油としての
物理的特性が劣るため好ましくない。
本発明のモノアルキルナフタレンとしては一般
式
で表わされるα−置換モノアルキルナフタレンで
も、一般式
で表わされるβ−置換モノアルキルナフタレンで
も使用することができるが、入手の容易さ、化合
物としての安定性などの点からβ−置換モノアル
キルナフタレンを用いるのが好ましい。
一方、一般式The total number of carbon atoms in R 1 , R 2 and R 3 of the alkyl group represented by [Formula] is 5 to 23, and the alkyl group directly bonded to the naphthalene ring is a tertiary alkyl group. It is necessary that the requirements are met. Alkylnaphthalenes that do not satisfy any one of the above three requirements are not preferred because they are inferior in oxidation stability and physical properties as a heat transfer oil compared to the alkylnaphthalenes of the present invention. The monoalkylnaphthalene of the present invention has the general formula Even α-substituted monoalkylnaphthalenes represented by the general formula Although β-substituted monoalkylnaphthalenes represented by the formula can also be used, it is preferable to use β-substituted monoalkylnaphthalenes from the viewpoint of ease of availability and stability as a compound. On the other hand, the general formula
【式】で表わされる第３級
アルキル基を構成するR1、R2およびR3はそれぞ
れ炭素数１〜21のアルキル基であり、かつR1、
R2およびR3の合計炭素数が５〜23であることが
必要であるが、モノアルキルナフタレンの熱媒体
油としての物理的特性の面からR1、R2およびR3
が炭素数１〜15のアルキル基であり、かつその合
計炭素数が７〜17が好ましい。またその酸化安定
性の点から、R1、R2およびR3がそれぞれ直鎖ア
ルキル基であるものが好ましい。
本発明のモノアルキルナフタレンにおいて、
R1、R2およびR3としては、具体的には例えば、
メチル基、エチル基、プロピル基、ブチル基、ペ
ンチル基、ヘキシル基、ヘプチル基、オクチル
基、ノニル基、デシル基、ウンデシル基、ドデシ
ル基、トリデシル基、テトラデシル基、ペンタデ
シル基などが好ましく用いられる。
さらに本発明のモノアルキルナフタレンにおい
て、特にR1とR2がメチル基またはエチル基であ
り、R3はR1、R2およびR3の合計炭素が７〜17と
なるような炭素数の直鎖アルキル基であるものが
より好ましい。
本発明のモノアルキルナフタレンの、一般式
で表わされる第３級アルキル基の好ましいものと
しては具体的には、例えば１，１−ジメチルヘキ
シル基、１−エチル−１−メチルペンチル基、
１，１−ジエチルブチル基、１，１−ジメチルヘ
プチル基、１−エチル−１−メチルヘキシル基、
１，１−ジエチルペンチル基、１，１−ジメチル
オクチル基、１−エチル−１−メチルヘプチル
基、１，１−ジエチルヘキシル基、１，１−ジメ
チルノニル基、１−エチル−１−メチルオクチル
基、１，１−ジエチルヘプチル基、１，１−ジメ
チルデシル基、１−エチル−１−メチルノニル
基、１，１−ジエチルオクチル基、１，１−ジメ
チルウンデシル基、１−エチル−１−メチルデシ
ル基、１，１−ジエチルノニル基、１，１−ジメ
チルドデシル基、１−エチル−１−メチルウンデ
シル基、１，１−ジエチルデシル基、１，１−ジ
メチルトリデシル基、１−エチル−１−メチルド
デシル基、１，１−ジエチルウンデシル基、１，
１−ジメチルテトラデシル基、１−エチル−１−
メチルトリデシル基、１，１−ジエチルドデシル
基、１，１−ジメチルペンタデシル基、１−エチ
ル−１−メチルテトラデシル基、１，１−ジエチ
ルトリデシル基、１，１−ジメチルヘキサデシル
基、１−エチル−１−メチルペンタデシル基、
１，１−ジエチルテトラデシル基などが挙げられ
る。
上記第３級アルキル基を有する本発明のモノア
ルキルナフタレンは通常、フリーデル・クラフツ
（Friedel−Crafts）アルキル化反応により合成で
きる。すなわちアルキル源として炭素数６〜24の
第３級アルキルハライド、アルコールや二重結合
位が分枝した炭素上にある炭素数６〜24の分枝モ
ノオレフインのいずれかを、好ましくは分枝モノ
オレフインをナフタレンと塩化アルミニウム、塩
化亜鉛、塩化鉄などの金属ハロゲン化物、硫酸、
リン酸、五酸化リン、フツ酸、フツ化ホウ素、酸
性白土、活性白土などの酸性触媒の存在下で反応
温度０〜250℃で反応させることにより得られる。
しかしフリーデル・クラフツアルキル化反応では
立体障害などの影響で炭素陽イオンの転移が起こ
り、必ずしも第３級アルキル基だけでなく第２級
アルキル基を有するモノアルキルナフタレンも生
成する可能性があるという欠点がある。したがつ
て第３級アルキル基のみを有するモノアルキルナ
フタレンを得るためには、他にナフタレンをアシ
ル化し、この生成物をトリメチルアルミニウムで
徹底メチル化する方法、第２級アルキル基を有す
るモノアルキルナフタレンの分枝位置の炭素原子
に結合した水素原子をハロゲン置換し、トリアル
キルアルミニウムと反応させる方法などもある。
上記のフリーデル・クラフツアルキル化反応で
第３級アルキル基を有するモノアルキルナフタレ
ンを合成する場合、ナフタレン環の８位の水素原
子との立体障害の影響からβ−置換体が主成分と
して生成する。
本発明のモノアルキルナフタレンからなる熱媒
体油は、単独でも通常の熱媒体油に要求される各
種性状とともに酸化安定性が特に良いという優れ
た性状を兼ね備えているが、本発明の熱媒体油に
必要に応じてさらに酸化防止剤、あわ消し剤、清
浄分散剤、さび止め剤あるいは流動点降下剤など
の公知の添加剤を添加してもよい。これら各種の
添加剤の詳細は、例えば“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。
また本発明の熱媒体油はその高い酸化安定性を損
ねない範囲において、必要に応じて鉱油や公知の
合成油を75重量％、好ましくは50重量％以下、特
に好ましくは25重量％以下混合することも可能で
ある。
（発明の実施例）
以下、本発明の内容を実施例および比較例によ
りさらに具体的に説明する。
実施例 １
４つ口フラスコにナフタレン700重量部を秤量
し、窒素雰囲気化で撹拌しながら150℃まで加熱
し、さらに220℃で焼成した活性白土100重量部を
添加して200℃まで加熱した。そこへ２−メチル
−１−ノネン500重量部を４時間かけて少量ずつ
滴下し、その後200℃に保つたまま１時間撹拌を
続け、ナフタレンと２−メチル−１−ノネンを反
応させた。
反応終了後、生成混合物を100℃に冷却してろ
過し、ろ液を減圧蒸溜してβ−（１，１−ジメチ
ルオクチル）ナフタレンを得た。このβ−（１，
１−ジメチルオクチル）ナフタレンの性状を示
す。
粘度：14.86 cSt、＠40℃、
流動点：−45℃以下、
沸点：165℃／１mmHg、
実施例 ２
２−メチル−１−ノネンの代わりに２−メチル
−１−ヘプテンを用い、他は実施例１と同様の手
法でナフタレンのアルキル化を行い、減圧蒸溜に
よりβ−（１，１−ジメチルヘキシル）ナフタレ
ンを得た。このβ−（１，１−ジメチルヘキシル）
ナフタレンの性状を示す。
粘度：10.65 cSt、＠40℃、
流動点：−45℃以下、
沸点：144℃／１mmHg、
実施例 ３
２−メチル−１−ノネンの代りに２−メチル−
１−ウンデセンを用い、他は実施例１と同様の手
法でナフタレンのアルキル化を行い、減圧蒸溜に
よりβ−（１，１−ジメチルデシル）ナフタレン
を得た。このβ−（１，１−ジメチルデシル）ナ
フタレンの性状を示す。
粘度：17.63 cSt、＠40℃、
流動点：−45℃以下、
沸点：185℃／１mmHg、
実験（実施例１〜３および比較例１〜２の化合
物）
上記の実施例１〜３により得られた本発明にか
かるモノアルキルナフタレンおよび比較のため従
来より熱媒体油として知られているナフテン系精
製鉱油（酸化防止剤として２，６−ジ−ｔ−ブチ
ル−４−メチルフエノールを1.0重量％添加；比
較例１）、ジイソプロピルナフタレン（比較例２）
の酸化安定性を評価するため、IP−280に規定さ
れる試験設備を用いて以下の条件で高温酸化試験
を行つた。
試験温度：170℃、
酸素流量：３／hr、
触媒：銅線１mmφ×80cm、
なお、酸化安定性の評価は、試料油の酸価が
1.0mgKOH／ｇとなつた時間を酸化試験寿命と定
義して行つた。その結果を第１表に示す。R 1 , R 2 and R 3 constituting the tertiary alkyl group represented by [Formula] are each an alkyl group having 1 to 21 carbon atoms, and R 1 ,
It is necessary that the total carbon number of R 2 and R 3 is 5 to 23, but from the viewpoint of physical properties of monoalkylnaphthalene as a heat transfer oil, R 1 , R 2 and R 3
is an alkyl group having 1 to 15 carbon atoms, and the total number of carbon atoms is preferably 7 to 17. Further, from the viewpoint of oxidative stability, it is preferable that R 1 , R 2 and R 3 are each a straight-chain alkyl group. In the monoalkylnaphthalene of the present invention,
Specifically, R 1 , R 2 and R 3 are, for example,
Methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc. are preferably used. Furthermore, in the monoalkylnaphthalene of the present invention, in particular, R 1 and R 2 are a methyl group or an ethyl group, and R 3 is a straight carbon number such that the total carbon number of R 1 , R 2 and R 3 is 7 to 17. More preferred are chain alkyl groups. General formula of the monoalkylnaphthalene of the present invention Preferred examples of the tertiary alkyl group represented by include, for example, 1,1-dimethylhexyl group, 1-ethyl-1-methylpentyl group,
1,1-diethylbutyl group, 1,1-dimethylheptyl group, 1-ethyl-1-methylhexyl group,
1,1-diethylpentyl group, 1,1-dimethyloctyl group, 1-ethyl-1-methylheptyl group, 1,1-diethylhexyl group, 1,1-dimethylnonyl group, 1-ethyl-1-methyloctyl group group, 1,1-diethylheptyl group, 1,1-dimethyldecyl group, 1-ethyl-1-methylnonyl group, 1,1-diethyloctyl group, 1,1-dimethylundecyl group, 1-ethyl-1- Methyldecyl group, 1,1-diethylnonyl group, 1,1-dimethyldodecyl group, 1-ethyl-1-methylundecyl group, 1,1-diethyldecyl group, 1,1-dimethyltridecyl group, 1-ethyl -1-methyldodecyl group, 1,1-diethylundecyl group, 1,
1-dimethyltetradecyl group, 1-ethyl-1-
Methyltridecyl group, 1,1-diethyldodecyl group, 1,1-dimethylpentadecyl group, 1-ethyl-1-methyltetradecyl group, 1,1-diethyltridecyl group, 1,1-dimethylhexadecyl group , 1-ethyl-1-methylpentadecyl group,
Examples include 1,1-diethyltetradecyl group. The monoalkylnaphthalene of the present invention having the above tertiary alkyl group can usually be synthesized by a Friedel-Crafts alkylation reaction. That is, as an alkyl source, either a tertiary alkyl halide having 6 to 24 carbon atoms, an alcohol or a branched monoolefin having 6 to 24 carbon atoms in which the double bond position is on a branched carbon, preferably a branched monoolefin. Olefins are combined with naphthalene, metal halides such as aluminum chloride, zinc chloride, iron chloride, sulfuric acid,
It is obtained by reacting at a reaction temperature of 0 to 250°C in the presence of an acidic catalyst such as phosphoric acid, phosphorus pentoxide, hydrofluoric acid, boron fluoride, acid clay, activated clay, or the like.
However, in the Friedel-Crafts alkylation reaction, carbon cations are transferred due to steric hindrance, and it is possible that monoalkylnaphthalenes containing not only tertiary alkyl groups but also secondary alkyl groups are produced. There are drawbacks. Therefore, in order to obtain monoalkylnaphthalenes having only tertiary alkyl groups, another method is to acylate naphthalene and thoroughly methylate this product with trimethylaluminum. There is also a method in which the hydrogen atom bonded to the carbon atom at the branch position is substituted with halogen and reacted with trialkylaluminum. When monoalkylnaphthalenes having a tertiary alkyl group are synthesized by the above Friedel-Crafts alkylation reaction, β-substituted products are produced as the main component due to steric hindrance with the hydrogen atom at the 8-position of the naphthalene ring. . The heat transfer oil made of monoalkylnaphthalene of the present invention has excellent properties such as particularly good oxidation stability as well as various properties required of ordinary heat transfer oils even when used alone. If necessary, known additives such as antioxidants, antifoaming agents, detergent dispersants, rust inhibitors, or pour point depressants may be added. Details of these various additives are described in, for example, "Petroleum Product Additives" edited by Toshio Sakurai (Saiwai Shobo).
In addition, the heat transfer oil of the present invention may be mixed with mineral oil or known synthetic oil in an amount of 75% by weight, preferably 50% by weight or less, particularly preferably 25% by weight or less, as long as its high oxidation stability is not impaired. It is also possible. (Examples of the Invention) Hereinafter, the contents of the present invention will be explained in more detail with reference to Examples and Comparative Examples. Example 1 700 parts by weight of naphthalene was weighed into a four-necked flask and heated to 150°C with stirring in a nitrogen atmosphere. Further, 100 parts by weight of activated clay fired at 220°C was added and heated to 200°C. Thereto, 500 parts by weight of 2-methyl-1-nonene was added dropwise little by little over 4 hours, and stirring was continued for 1 hour while maintaining the temperature at 200°C to cause naphthalene and 2-methyl-1-nonene to react. After the reaction was completed, the resulting mixture was cooled to 100°C and filtered, and the filtrate was distilled under reduced pressure to obtain β-(1,1-dimethyloctyl)naphthalene. This β-(1,
The properties of 1-dimethyloctyl)naphthalene are shown. Viscosity: 14.86 cSt, @40℃, Pour point: -45℃ or less, Boiling point: 165℃/1mmHg, Example 2 2-Methyl-1-heptene was used instead of 2-methyl-1-nonene, and the others were the same. Naphthalene was alkylated in the same manner as in Example 1, and β-(1,1-dimethylhexyl)naphthalene was obtained by distillation under reduced pressure. This β-(1,1-dimethylhexyl)
Shows the properties of naphthalene. Viscosity: 10.65 cSt, @40℃, Pour point: -45℃ or less, Boiling point: 144℃/1mmHg, Example 3 2-Methyl- instead of 2-methyl-1-nonene
Naphthalene was alkylated using 1-undecene in the same manner as in Example 1, and β-(1,1-dimethyldecyl)naphthalene was obtained by distillation under reduced pressure. The properties of this β-(1,1-dimethyldecyl)naphthalene are shown below. Viscosity: 17.63 cSt, @40℃, Pour point: -45℃ or less, Boiling point: 185℃/1mmHg, Experiment (compounds of Examples 1-3 and Comparative Examples 1-2) Obtained according to Examples 1-3 above Monoalkylnaphthalene according to the present invention and naphthenic refined mineral oil conventionally known as a heat transfer oil for comparison (with 1.0% by weight of 2,6-di-t-butyl-4-methylphenol added as an antioxidant) ; Comparative Example 1), diisopropylnaphthalene (Comparative Example 2)
In order to evaluate the oxidation stability of , a high temperature oxidation test was conducted under the following conditions using test equipment specified in IP-280. Test temperature: 170℃, oxygen flow rate: 3/hr, catalyst: copper wire 1mmφ x 80cm, oxidation stability evaluation is based on the acid value of the sample oil.
The oxidation test life was defined as the time when the value reached 1.0 mgKOH/g. The results are shown in Table 1.
【表】
第１表の酸化試験寿命の結果から明らかなよう
に、本発明にかかるモノアルキルナフタレンから
なる熱媒体油は非常に高い高温酸化安定性を示し
ている。それに対して、従来より熱媒体油として
使用されている精製鉱油、アルキルナフタレンな
どの化合物は、酸化試験寿命が本発明の化合物よ
り大きく劣つている。
このように本発明のモノアルキルナフタレンか
らなる熱媒体油は従来公知の鉱油系熱媒体油や他
のアルキルナフタレン系熱媒体油では到達し得な
い高い酸化安定性を有するものである。[Table] As is clear from the oxidation test life results in Table 1, the heat transfer oil comprising monoalkylnaphthalene according to the present invention exhibits extremely high high temperature oxidation stability. On the other hand, compounds such as refined mineral oils and alkylnaphthalenes conventionally used as heat transfer oils have significantly inferior oxidation test life to the compounds of the present invention. As described above, the monoalkylnaphthalene heat transfer oil of the present invention has high oxidation stability that cannot be achieved with conventionally known mineral oil heat transfer oils or other alkylnaphthalene heat transfer oils.
Claims (1)
21のアルキル基であり、かつR1、R2およびR3の
合計炭素数は５〜23である）で表わされるモノア
ルキルナフタレンからなる熱媒体油。 ２ 前記モノアルキルナフタレンが一般式 （式中、R1、R2およびR3はそれぞれ炭素数１〜
21のアルキル基であり、かつR1、R2およびR3の
合計炭素数は５〜23である）で表わされるβ−置
換モノアルキルナフタレンであることを特徴とす
る特許請求の範囲第１項記載の熱媒体油。 ３ 前記R1、R2およびR3がそれぞれ直鎖アルキ
ル基であることを特徴とする特許請求の範囲第１
項または第２項記載の熱媒体油。[Claims] 1. General formula (In the formula, R 1 , R 2 and R 3 each have 1 to 1 carbon atoms.
21 alkyl group, and the total carbon number of R 1 , R 2 and R 3 is 5 to 23). 2 The monoalkylnaphthalene has the general formula (In the formula, R 1 , R 2 and R 3 each have 1 to 1 carbon atoms.
21 alkyl group, and the total carbon number of R 1 , R 2 and R 3 is 5 to 23) The heat transfer oil described. 3. Claim 1, wherein each of R 1 , R 2 and R 3 is a straight-chain alkyl group.
The heat transfer oil according to item 1 or 2.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59249772A JPS61127782A (en) | 1984-11-28 | 1984-11-28 | Heat transfer oil |
| US06/745,576 US4665275A (en) | 1984-07-05 | 1985-06-17 | Thermal medium oils |
| GB08516035A GB2161176B (en) | 1984-07-05 | 1985-06-25 | Thermal medium oils |
| DE3524186A DE3524186C2 (en) | 1984-07-05 | 1985-07-05 | Oils for use as thermal medium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59249772A JPS61127782A (en) | 1984-11-28 | 1984-11-28 | Heat transfer oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61127782A JPS61127782A (en) | 1986-06-16 |
| JPH0414717B2 true JPH0414717B2 (en) | 1992-03-13 |
Family
ID=17197995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59249772A Granted JPS61127782A (en) | 1984-07-05 | 1984-11-28 | Heat transfer oil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61127782A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080234157A1 (en) * | 2007-03-20 | 2008-09-25 | Yoon Beth A | Alkylaromatic lubricant fluids |
-
1984
- 1984-11-28 JP JP59249772A patent/JPS61127782A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61127782A (en) | 1986-06-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0006710B1 (en) | An adduct of a benzotriazole and lubricant compositions containing such adduct | |
| JPS61179296A (en) | Synthetic base oil | |
| GB2168378A (en) | Mixtures of alkylated naphthalenes | |
| JPH02188555A (en) | P,p'-dinonyldiphenylamine and composition mixed with the amine | |
| US3914241A (en) | Oil soluble derivatives of 2,5-di-mercapto-1,3,4-thiadiazole and process for preparation thereof | |
| US5552071A (en) | Alkylated diphenyl ether lubricants | |
| US4737297A (en) | Synthetic lubricating oils | |
| US2723237A (en) | Phosphoric acid esters of diethylene glycol ethers and lubricants containing the same | |
| JPH0242880B2 (en) | ||
| EP0230779A1 (en) | Alkylresorcinol phosphites | |
| US5371248A (en) | Alkylated benzofuran-derived lubricants | |
| US4519928A (en) | Lubricant compositions containing N-tertiary alkyl benzotriazoles | |
| JPH0414717B2 (en) | ||
| GB2161176A (en) | Thermal medium oils | |
| US3499840A (en) | Chlorine derivatives of m-diphenoxybenzene and process of preparation thereof | |
| US3122575A (en) | Diphenyl ether derivatives | |
| US3260672A (en) | Synthetic ester lubricating oil containing certain haloalkyl carboxylic acid esters | |
| JPH0414716B2 (en) | ||
| JPH0414714B2 (en) | ||
| JPH0558039B2 (en) | ||
| JPH0414715B2 (en) | ||
| JP2623111B2 (en) | Heat transfer oil | |
| US4153563A (en) | Lubricant compositions containing benzotriazole-allyl sulfide reaction products | |
| US5990056A (en) | Compositions containing an organo-substituted benzophenone | |
| US4202783A (en) | Antioxidant additives and lubricant compositions containing same |