JPS6124561A - Manufacture of sulfide perbasic salicylate - Google Patents
Manufacture of sulfide perbasic salicylateInfo
- Publication number
- JPS6124561A JPS6124561A JP14760685A JP14760685A JPS6124561A JP S6124561 A JPS6124561 A JP S6124561A JP 14760685 A JP14760685 A JP 14760685A JP 14760685 A JP14760685 A JP 14760685A JP S6124561 A JPS6124561 A JP S6124561A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- product
- salicylic acid
- metal
- salicylate
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Carbonaceous Fuels (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
本発明は、脂肪族炭化水素置換ナリチル酸またＧＪイの
金属１ふ１を硫化することにＪ、るｂ１化された過塩基
の脂肪Ｍ炭化水素置換１ナリチル酸金属場の製造り法、
このｊノ法により製造される生成物、並びにこれら生成
物を含有する油組成物に関するものて゛ある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the sulfurization of aliphatic hydrocarbon-substituted nalycylic acid or GJ-1 metal The manufacturing method of the place,
The present invention relates to products produced by this method as well as oil compositions containing these products.
英国１．ｌ＋ ｉｔｆ第１，２８７，８１２号明１ｉ！
ｔかう、この種のう１、載物Ａ３．よびこれらを洗剤お
Ｊ：び摩耗防止剤として含有づる油組成物が既に知られ
ている。この明細書は、脂肪ＩＭＩ欠化水化水素置換１
ナリチル酸はその金属塩と硫黄元素、アルカリ土類塩基
（たとえば水酸化物）および溶剤（たとえばエチレング
リコール）とを少なくとも１５０℃にて反応させ、ざら
に必要に応じ二酸化炭素と反応ざμることを開示しでい
る。英国待檜第１．１９４．５ｏ、＋＝；明１ｔＩｆｆ
書に−も同様な方法が開示されている。UK 1. l+ itf No. 1,287,812 Mei 1i!
This kind of item is A3. and oil compositions containing these as detergents and antiwear agents are already known. This specification describes the fatty IMI depleted hydrogen hydride substitution 1
Nalicylic acid is prepared by reacting its metal salt with elemental sulfur, an alkaline earth base (e.g. hydroxide) and a solvent (e.g. ethylene glycol) at at least 150°C, and optionally reacting with carbon dioxide. has been disclosed. British waiting tree 1.194.5o, +=; Ming 1tIff
A similar method is also disclosed in the book.
しかしながら、この公知方法は、硫黄元素どの反応に際
し相当程度の脱カルボキシル化が生ずるという欠点を持
つことが判明しｌ〔。However, this known process has been found to have the disadvantage that a considerable degree of decarboxylation occurs during the reaction of the sulfur element.
今回、硫黄元素の代りにハロゲン化硫黄と反応させるこ
とにより、脱力ルボギシル化をづ゛っど低い程度にしう
ろことを付き止めた。This time, by reacting with halogenated sulfur instead of elemental sulfur, we were able to keep the scales from reducing the amount of deactivated rubogysylation.
したがって、本発明は脂肪族炭化水素「ｉ換ザリヂル酸
またはその金属塩をハロゲン化硫黄で硫化し、次いでこ
の反応生成物を過塩基サリブル酸金属塩（二変換りるこ
とを特徴とする、硫化された過塩ζＬの脂肪／Ａ Ｉ）
２化水系尼換リ−リチル酸金属場の製造１ノと人に関す
るもので゛ある。Accordingly, the present invention involves sulfiding an aliphatic hydrocarbon "i-converted salidylic acid or a metal salt thereof with a sulfur halide, and then converting the reaction product into an overbased salivylic acid metal salt (a sulfurized oversalted ζL fat/A I)
This article concerns the manufacturing process and people of a dihydric acid-based dihydric acid metal field.
さらに本発明は、この方法により製造される生成物キ１
＆びにこれら生成物を含有する油組成物にも関り−るｂ
のである。過塩基１ナリチル酸金属塩の適−りる金属は
、たどえばアルカリ金属（たとえば１ｉ、Ｃｓ、Ｎａお
よびＩ＜）、アルカリ土類金属（ＡニドえＩＪ Ｃｊｉ
、 Ｂａ 、 ３ ｒおよびＭｇ）、並びに多価金属
（たとえばＺｎおよびＯｒ）である。Furthermore, the present invention provides a product key 1 produced by this method.
and oil compositions containing these products.
It is. Suitable metals for overbased metal salts of 1-nalycylic acid include alkali metals (such as 1i, Cs, Na, and I<), alkaline earth metals (Ani, IJ, Cji,
, Ba, 3r and Mg), and polyvalent metals (e.g. Zn and Or).
たとえばカルシウム、バリウムあよぴマグネシウムのＪ
、０４Ｌノ′ルカリ土類金属が好適である。For example, calcium, barium ayopi magnesium J
, 04L alkaline earth metals are preferred.
適りる脂肪族炭化水素置換ザリヂル酸は上記英国特許明
Ｉｌｌ由に記載されている。好適なものはＣ８−３０−
フル４−ルサリチル酸である。Suitable aliphatic hydrocarbon-substituted thalidylic acids are described in the above-mentioned British patent. The preferred one is C8-30-
Full 4-rusalicylic acid.
脂肪瓜炭化水素置換ナリチル酸の金属塩としてはアルカ
リ金属塩特にナトリウム塩が好適である。As the metal salt of the fatty melon hydrocarbon-substituted nalicylic acid, alkali metal salts, particularly sodium salts are preferred.
脂肪族炭化水素（たとえば旧−ヘキサジ）のような溶剤
中でハロゲン化硫黄による硫化を行なうのが好ましい。Preferably, the sulfurization is carried out with a sulfur halide in a solvent such as an aliphatic hydrocarbon (for example old-hexadi).
キシレンのような芳香族溶剤の使用は避けるべきである
、１何故なら、これら溶剤−ｂハ［１グン化硫黄（゛硫
化されうるからである。好適なハロゲン化硫黄は塩化硫
黄、たとえば５ｃｐ２および５２ＣＱ２である。The use of aromatic solvents such as xylene should be avoided, since these solvents can be sulfurized. Preferred sulfur halides include sulfur chlorides, such as sulfur chloride and It is 52CQ2.
反応は室温ぐ行なうこともできるが、成る程度の加熱を
行なって、たとえば６０℃まで加熱づることもできる。The reaction can be carried out at room temperature, but can also be carried out with moderate heating, for example up to 60°C.
Ｓ：置換１ナリナル酸もしくはナリｆ−ル酸塩のモル比
はたとえば０．２５〜３、好ましくは０．５〜２である
。The molar ratio of S: substituted 1 nalinal acid or nalinal acid salt is, for example, 0.25-3, preferably 0.5-2.
次いで、反応混合物を必要に応じ酸性化さ口′Ｃ遊離の
硫化した酸を得、これを所望に応じ又ｅ過する。The reaction mixture is then optionally acidified to obtain free sulfurized acid, which is optionally filtered.
潤滑油組成物中Ｃ洗浄特性が良好（・シかも摩耗の少な
い対応の過塩基ナリチル酸塩を製造するのに］Ｉ酸物（
，１使用される。In lubricating oil compositions, C-acid (I) has good cleaning properties (in order to produce a corresponding overbased nalicylate with less wear).
,1 is used.
たとえは英国１１１Ｊｉ／Ｆ第７８６，１６７号明細書
に記載され−（いるＪ、うに、溶剤Ｉことえば炭化水素
溶剤好ましくは１シレンのような芳香族炭化水素溶剤中
で４：／ Ｉ−）れＩ、−タ載物ど塩基性金属化合物（
好ましくは水酸化物） １ｌｊＪ：び−酸化炭素とを反
応さＩ！ｃ過塩基化］稈を１ｉなうことができる。過塩
基化程度は金Ｉｌｌ対すリ１ル酸の当量比として定義さ
れる塩基ａ指数＋１１．１．）としく表わされる。An example is given in UK 111Ji/F No. 786,167 - (J, uni, solvent I, such as a hydrocarbon solvent, preferably 1 in an aromatic hydrocarbon solvent such as cylene:/I-) Basic metal compounds (
Preferably a hydroxide) 1ljJ: Reacts with carbon oxide I! c. Overbasing] The culm can be made 1i. The degree of overbasing is defined as the base a index defined as the equivalent ratio of lylic acid to gold Ill + 11.1. ).
１１１られた反応混合物に軽貝鉱油を加え、次いで炭化
水系溶剤および生成した水を全て蒸留により除去するこ
とがｅきる。Light shell mineral oil can be added to the reacted reaction mixture, and then all the hydrocarbon solvent and water produced can be removed by distillation.
硫化生成物の得られた油溶液を所望に応じてｅ過し、次
いＣｔことえば８１滑油またはガソリンなどの燃料部の
ような油へ添加することができる。The resulting oil solution of the sulfided product can be filtered if desired and then added to an oil such as a Ct 81 oil or a fuel part such as gasoline.
同■４係属中の英国特許出願第ｓ、３３ｏ、４４１号明
細書に記載され−Ｃいるように、硫化前まＩこは硫化後
に、生成物をたとえばｉ酸のようｔ！硼素化合物と反応
さＶることができる。As described in co-pending UK Patent Application No. s, 33o, 441, the product can be prepared, for example, as an acid, before or after sulfurization. Can react with boron compounds.
本発明の反応生成物は、その混合物を含め、油。The reaction products of the present invention include oils, including mixtures thereof.
組成物、特に潤滑油組成物または濃厚物もしくは燃料、
たとえば自動車クランクケース油に全組成物の全量に対
しｏ、ｏｏｉ〜６５重量％、特に０．１〜１５重量％の
範囲の濃度で配合することかできる。compositions, especially lubricating oil compositions or concentrates or fuels,
For example, they can be incorporated into automobile crankcase oils in concentrations ranging from o,ooi to 65% by weight, particularly from 0.1 to 15% by weight, based on the total weight of the entire composition.
本発明の添加物を加えつるｆＰｌ渭油は鉱物潤滑油だけ
でなく合成油をも包含する。合成炭化水素潤滑油も使用
することができ、さらにたとえばジー２−エヂルヘキシ
ルセバシン酸エステル、炭酸エステル、燐酸エスラル、
ハロゲン化炭化水素、ポリシリコーン、ポリグリコール
、例えばテ［・ラエチレングリ］−ルのＣ１３オキソ酸
ジエスｊルのようなグリニ」−ルーエステルなどのニー
塩基壇生酸エスラルを包含する非炭化水素合成油も使用
することができる。これら油の混合物、特に水素化油を
包含りる鉱物潤滑油および合成潤滑油の混合物も使用り
ることができる。The additive fPl oil of the present invention includes not only mineral lubricating oils but also synthetic oils. Synthetic hydrocarbon lubricating oils may also be used, such as di-2-edylhexyl sebacate, carbonate, esral phosphate,
Non-hydrocarbon synthetic oils, including halogenated hydrocarbons, polysilicone, polyglycol, dibasic acid esters such as C13 oxoacid diethyl of tether, etc. can also be used. Mixtures of these oils can also be used, especially mixtures of mineral and synthetic lubricating oils, including hydrogenated oils.
ガソリンまたは燃料油、たとえばディーゼル燃１′８１
など１．゛使用づる場合、−・般に全組成物重量に二対
し＋１．００１−Ｏ，ｈ重量％の反応生成物を使用ツる
。Gasoline or fuel oil, such as diesel fuel 1'81
etc.1. When used, generally +1.001-O,h% by weight of the reaction product is used based on the weight of the total composition.
−・般Ｖ′、炭化水素希釈剤中の１５へ・６５重猷％の
前記反応生成物と８５〜３５重量％の鉱物潤滑油とから
なる淵り物が取り扱いの容易さのため製造される。- General V', a liquid product consisting of 15 to 65% by weight of said reaction product and 85 to 35% by weight of mineral lubricating oil in a hydrocarbon diluent is prepared for ease of handling. .
他の添１１１１物、たとえば染料、流動点降下剤、摩耗
防止剤たとえば燐酸トリクレジル、ジブオ燐酸＋１１艷
鉛、酸化防止剤！ことえばフｒニルーα−ナフブル ７
ミン、ビス−フェノール類たとえば４゜４°−メＦレン
ビス（３，６−ジーｔ−ブチルフェノール） 、Ｎｉｌ
！１指数向」−剤たとえば共役ジエンおよび必要に応じ
ス゛ルンの水素化（共）重合体、エチレンｔ１級Ａレフ
イン共重合体、ポリメチルアクリレート、ポリイソブチ
レンなど、並び【３−無灰分分散剤たとえばポリイソブ
チレンと無水マレイン酸どアミンおよび／またはポリオ
ールどの反応生成物、或いは他の金属含有表面活性剤た
とえば過塩基性金属ザリチル酸塩などを上記組成物中レ
ニ存在さＵることもできる。Other additives such as dyes, pour point depressants, anti-wear agents such as tricresyl phosphate, dibuphosphoric acid + 11 lead, antioxidants! Kotoba r niru α-nafbul 7
Ni, bis-phenols such as 4°4°-methylenebis(3,6-di-t-butylphenol), Nil
! 1 index-directing agents such as hydrogenated (co)polymers of conjugated dienes and optionally sulfur, ethylene t-1 class A reflex copolymers, polymethyl acrylate, polyisobutylene, etc.; and 3- ashless dispersants such as polyester Reaction products such as isobutylene and maleic anhydride and/or polyols, or other metal-containing surfactants such as overbased metal salicylates, may also be present in the compositions.
アミンとホルムアルデヒドとアルキル７１ノールとの反
応生成物（マンニッヒ塩基）−し存在さＵることがて゛
さる。It is known that a reaction product (Mannich base) of amine, formaldehyde and alkyl 71-nor exists.
本発明を以下の実施例により更に説明づる。The invention will be further illustrated by the following examples.
Ｕユ
３５重量％鉱鉱物１滑油中の６５重間％Ｃ１４−１８−
アルキル→ノリデル酸ナトリウム塩（６００ミリ当１４
＞の酸、酸価１．２０ミリ当吊／グ）の濃厚物５００ｇ
に、３６０ミリ肖量（３０！ｌ？）のＳ Ｃｐ２を約２
５℃の温度にて滴加した。添加および後反応の全反応時
間は５時間とした。この反応生成物を濃塩酸で酸性化し
、ジ【１ル［−一−ｊルＣ抽出し、相分離の後にＩ＋’
過し、ぞの後溶剤を蒸発にＪζり除去した。収量：４９
１ｇ。35% by weight of minerals 1 65% by weight in lubricating oil C14-18-
Alkyl → Noriderate sodium salt (14 per 600ml)
> acid, acid value 1.20 mm/g) concentrate 500g
, the S Cp2 of 360 mm (30! l?) is about 2
It was added dropwise at a temperature of 5°C. The total reaction time for addition and post-reaction was 5 hours. The reaction product was acidified with concentrated hydrochloric acid, extracted with di[1-[-1-j]C, and after phase separation, I+'
After filtration, the solvent was removed by evaporation. Yield: 49
1g.
Ｓ ： ３，４１「、吊％、酸１ｆｉｉ１．２４ミリ
当吊／グ（生成物Δ）、。S: 3.41%, acid 1fii 1.24 mm/g (product Δ).
！Ｂ４ｑ薄１ユ
実施例′１のＣ−アルキルナリチル酸ノドリウｌＸＪス
晶の濃厚物５００ｇに、５９０ミリ当昂（１９ｇ＞のＳ
と４５Ｉの１−１−レンゲリコールとを加えた。この８
Ｎ合物を撹拌しながら １２５℃まで加熱し、このンｉ
１１！ １０−１．−、 ’１ ＋＋；“１間保った。! To 500 g of the concentrate of C-alkylnaritylic acid 1
and 45I of 1-1-lengelicol were added. This 8
Heat the N compound to 125°C while stirring, and
11! 10-1. −, '1 ++; “Kept for 1 minute.
次いで、温度を１５０℃まで１冒さｕ１約５５０ｍｍ
ｌ−Ｉ ｇの圧カドでこの温度に１１１′１間保−＞
／ｊ 。次いで、温度を１９５℃まで１’ｊｆさせ、１
１−力を！＋ Ｏ・−６０ｎｔｍ ｌ−１（ＩまＣ低ト
させ、これら条件を２１１、’１間１１持した。次いで
、反応生成物を約１００°Ｃ：１、Ｃ冷却した後、濾過
助剤を通して濾過し、２．９千ｚＩ）％のＳ含有ｈ１と
０．３９ミリ当罪／３の酸価とをイ１りる生成物（生成
物１３） ５５４ｇを得た。Then, the temperature was increased to 150℃ for about 550mm
Maintain this temperature for 111'1 at a pressure of l-I g.
/j. Then, the temperature was increased to 195°C by 1'jf, and
1-Power! The reaction product was then cooled to about 100°C and filtered through a filter aid. Filtration gave 554 g of a product (Product 13) having an S content of 2.9,000 zI)% and an acid value of 0.39 mm/3.
結論＝Ｓ２Ｃｐ２と比較しで、Ｓとの反応では相当程度
の脱カルボキシル化が生じた。Conclusion = A significant degree of decarboxylation occurred in the reaction with S compared to S2Cp2.
支亀五ユ
実施例１にしたがっＵ、 ｉｏｏミリ″！ｉ吊（５１
，８！Ｉ）の純Ｃ１４−１８−アルキルザリヂル酸（酸
価１９３ミリ当ｆｆｌ／ｌに６−Ｆ−ヘキ丈ン中の６０
ミリ当量（４ｇ）の８２Ｃｆ１２を約２５℃に（加えた
。この反応生成物を水洗し、ぞしく相分離の後に溶剤を
蒸発除去した。収量：５２．２ｇ、 Ｓ ： ３．！
ｌ小吊％。According to Embodiment 1, ioo mm''!i hanging (51
,8! I) of pure C14-18-alkylsalidylic acid (acid value 193 mmol/ffl/l and 60% of 6-F-hexane)
Milliequivalents (4 g) of 82Cf12 were added at about 25° C. The reaction product was washed with water and the solvent was evaporated off after proper phase separation. Yield: 52.2 g, S: 3.!
l Small hanging%.
酸価：１９６ミリ当量／９（生成物Ｃ）。Acid value: 196 meq/9 (product C).
批蚊χ差１
実施例２０Ｍ Ｃ１４−１８−アルキルリ゛リチル酸１
９３ミリ当石（ｉｏｏｇ）に、 １９３ミリ当量（６，
１）（１）Ｓと１９３．ｌＪ当量（７，２ｇ）のｃａ（
Ｏｆ−１＞２と１．５ｔＪの１チレングリコールとを加
えた。実施例２にしたがっにの混合物を反応させた。収
量：１０２シ、Ｓ・３．０重量％、酸価： １．４５ミ
リ当聞／Ｓｌ（イＩ Ｉ戊１カ１〕 ） 。Mosquito χ difference 1 Example 20M C14-18-alkyl lyrylic acid 1
93 mm equivalent (ioog), 193 mm equivalent (6,
1) (1) S and 193. lJ equivalent (7,2 g) of ca (
Of-1>2 and 1.5 tJ of 1 tylene glycol were added. The mixture of crabs was reacted according to Example 2. Yield: 102 ml, S・3.0% by weight, acid value: 1.45 mm/Sl (II 1 1/Sl).
結Ｑ ： Ｓ ２ ｃ、ｐ２と比較して、Ｓとの反応ｅ
は相当程度の脱カルボキシル化が生じた、。Connection Q: Reaction e with S compared to S 2 c, p2
A significant degree of decarboxylation occurred.
丈Ｍｌｌ、ＥＬβ−
実施例？の硫化Ｇ １４−１８−アルキルサリチル酸１
１１！＋！ｉ９ （３Ｇ：ｌ（ｉ ミリ当量）をｅ２８
０ｇ（７）キシレンと８０８ＵのメタノールとにＪ、り
希釈した。この混合ｉＶ ４） １１１１０９ （！＋
（１９０ミリ当ｆｉｊ）（ＤＣａ （ＯＨ）２ど１凸’
に ｌｊＴ （１１１５間反応さした。反応生成物を遠
心分１１１１１ Ｌ、、１ ！ｉ ＋１ ＋ｌ ｊｌの
鉱物潤滑油を加え、溶剤を蒸発させ（，２、８４ｆｉ
！４ｉ％のＣａと１．２７（７） Ｂ、 １． 、！：
ライ４−！Ｊ−る油部厚物３７’／Ｊ／を冑た（生成
物１）。Length Mll, ELβ- Example? Sulfide of G 14-18-alkyl salicylic acid 1
11! +! i9 (3G:l (i milliequivalent) to e28
Diluted with 0 g (7) xylene and 808 U of methanol. This mixed iV 4) 111109 (!+
(190 mm per fij) (DCa (OH) 2nd 1 convex'
The reaction product was centrifuged for 11111 L,,1 !i +1 +l jl of mineral lubricating oil was added, and the solvent was evaporated (,2,84fi
! 4i% Ca and 1.27(7) B, 1. ,! :
Rai 4-! J-ru oil part thickness 37'/J/ was removed (Product 1).
犬Ｕ−１１４
４００：／のキシレンおよび６０ｇのメタノール中の実
ｆＡＩ１例２の硫化Ｃ−アルキルサリチル酸２０＋＞７
（３９２ミリ当量）の溶液を６０９（１６２２ミリ当
ｆｆ１） １７）Ｃａ （Ｏｌ−１） ２ Ｆ５５℃ｋ
ｍ ’ｒ １ 時Ｆｍ処３’ｌｌ ｂ ｋ。Dog U-114 400:/Actual fAI 1 Example 2 Sulfurized C-Alkylsalicylic Acid 20+>7 in xylene and 60 g methanol
(392 meq) solution at 609 (1622 meq ff1) 17) Ca (Ol-1) 2 F55℃k
m'r 1 o'clock Fm place 3'll b k.
次い（・、ｌＩｌ、Ｏｓ？ （（１３３ミリ当量）のＣ
Ｏ２を導入しｔ、： 、、 ｑ＋＞処理することにより
、８．５３３重丸のＣａと２１２ΦｌＩｔ％のＳと２．
６のＢ、 １．とを右する生成物２ｈ３．（ｉ！／を観
また（クー酸物Ｆ）。Then (・, lIl, Os? ((133 meq) of C
By introducing O2 and treating with t, : , q+>, 8.533 folds of Ca, 212ΦlIt% of S and 2.
6B, 1. and the product 2h3. (See i!/ again (Chuic acid F).
害−席−１リーＵ
＋０００ｊ／のキシレンと１５０ｇのメタノール中の実
施例２の硫化Ｃ−アルキルサリブール酸５００？？ （
！１ｉｌＯミリｒｉ ｆ＋！ ）の溶液を３４５ｇ（９
３１０ミリ当量）の（’、２＋ （Ｏｌｌ）２で５５℃
にて１時間処理した。次いて・、１５１？Ｊ（６旧連ミ
リ当量）のＣＯ２を導入しに：。後処理Ｊることににす
、１８０８止皐％のＣａと１．８０Ｉｒｉ 、ＩＴＪ
％のＳと７．９の８．１．とを右する生成物８４０ｊを
１９ｋ（生成物Ｇ）。500% of the sulfurized C-alkylsalibulic acid of Example 2 in xylene and 150g of methanol. ? (
! 1ilOmilri f+! ) solution of 345g (9
310 meq) of (', 2+ (Oll)2 at 55 °C
The mixture was treated for 1 hour. Next... 151? J (6 old milliequivalents) of CO2 is introduced:. Post-treatment J, 1808% Ca and 1.80Iri, ITJ
%S and 7.9 of 8.1. and the product 840j to 19k (product G).
Claims (7)
をハロゲン化硫黄で硫化し、次いでこの反応生成物を過
塩基サリチル酸金属塩に変換することを特徴とする、硫
化された過塩基の脂肪族炭化水素置換サリチル酸金属塩
の製造方法。(1) Aliphatic carbonization of a sulfurized overbase, characterized by sulfiding an aliphatic hydrocarbon-substituted salicylic acid or its metal salt with sulfur halide, and then converting the reaction product to an overbased metal salicylate. A method for producing a hydrogen-substituted salicylic acid metal salt.
属である特許請求の範囲第１項に記載の方法。(2) The method according to claim 1, wherein the metal of the overbased salicylic acid metal salt is an alkaline earth metal.
＿０−アルキルサリチル酸である特許請求の範囲第１項
または第２項に記載の方法。(3) Aliphatic hydrocarbon substituted salicylic acid is C_8_-_3
_0-Alkylsalicylic acid, the method according to claim 1 or 2.
比が０．２５〜３である特許請求の範囲第１項乃至第３
項のいずれかに記載の方法。(4) S: Claims 1 to 3 in which the molar ratio of substituted salicylic acid or salicylate is 0.25 to 3.
The method described in any of the paragraphs.
させる特許請求の範囲第１項乃至第４項のいずれかに記
載の方法。(5) The method according to any one of claims 1 to 4, in which the product before or after sulfurization is reacted with a boron compound.
載の方法により製造される生成物。(6) A product produced by the method according to any one of claims 1 to 5.
０１〜６５重量％とからなる油組成物、特に潤滑油組成
物または濃厚物もしくは燃料。(7) Oil and the product according to claim 6 0.0
01 to 65% by weight, especially lubricating oil compositions or concentrates or fuels.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8417298 | 1984-07-06 | ||
| GB848417298A GB8417298D0 (en) | 1984-07-06 | 1984-07-06 | Preparation of sulphurized overbased salicylates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6124561A true JPS6124561A (en) | 1986-02-03 |
| JPH0580518B2 JPH0580518B2 (en) | 1993-11-09 |
Family
ID=10563524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14760685A Granted JPS6124561A (en) | 1984-07-06 | 1985-07-04 | Manufacture of sulfide perbasic salicylate |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0168110B1 (en) |
| JP (1) | JPS6124561A (en) |
| BR (1) | BR8503202A (en) |
| CA (1) | CA1255691A (en) |
| DE (1) | DE3565258D1 (en) |
| GB (1) | GB8417298D0 (en) |
| SG (1) | SG6790G (en) |
| ZA (1) | ZA855047B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6364902U (en) * | 1986-10-16 | 1988-04-28 | ||
| JP2007039457A (en) * | 2005-07-29 | 2007-02-15 | Chevron Oronite Co Llc | Low-sulfur metal-based detergent-dispersant |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2149810B (en) * | 1983-11-15 | 1987-04-08 | Shell Int Research | Borated basic metal salt and oil composition containing it |
| GB8714922D0 (en) * | 1987-06-25 | 1987-07-29 | Shell Int Research | Lubricating oil composition |
| US6828415B2 (en) | 1993-02-19 | 2004-12-07 | Zentaris Gmbh | Oligopeptide lyophilisate, their preparation and use |
| GB201501991D0 (en) | 2015-02-06 | 2015-03-25 | Castrol Ltd | Uses and compositions |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2256441A (en) * | 1940-03-08 | 1941-09-16 | Socony Vacuum Oil Co Inc | Mineral oil composition and improving agent therefor |
| JPS60147497A (en) * | 1984-01-09 | 1985-08-03 | Cosmo Co Ltd | Preparation of salicylate-containing basic alkaline earth metal sulfide phenate type detergent |
| JPS60168793A (en) * | 1984-02-13 | 1985-09-02 | Cosmo Co Ltd | Production of basic sulfurized alkaline earth metal phenate detergent |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2319662A (en) * | 1941-10-31 | 1943-05-18 | American Cyanamid Co | Lubricating oils |
| US2311931A (en) * | 1941-12-27 | 1943-02-23 | American Cyanamid Co | Lubricant |
| USRE22910E (en) * | 1941-12-31 | 1947-09-02 | E-oxcxs-m | |
| US2336074A (en) * | 1942-05-16 | 1943-12-07 | American Cyanamid Co | Lubricating oil |
| GB786167A (en) * | 1954-09-27 | 1957-11-13 | Shell Res Ltd | Improvements in or relating to the preparation of basic oil-soluble polyvalent metalsalts of organic acids and solutions of said basic salts in oils, and the resultingsalts |
| GB825315A (en) * | 1957-02-18 | 1959-12-16 | Socony Mobil Oil Co Inc | Complex carbonated metal salts of alkyl phenol sulphides |
| GB1094609A (en) * | 1965-08-23 | 1967-12-13 | Lubrizol Corp | Oil soluble basic alkaline earth metal salts of phenol sulfides |
| US3595791A (en) * | 1969-03-11 | 1971-07-27 | Lubrizol Corp | Basic,sulfurized salicylates and method for their preparation |
| US3595790A (en) * | 1969-10-22 | 1971-07-27 | Lubrizol Corp | Oil soluble highly basic metal salts of organic acids |
| GB1597482A (en) * | 1977-01-28 | 1981-09-09 | Exxon Research Engineering Co | Metal phenates |
| US4320016A (en) * | 1979-09-24 | 1982-03-16 | Texaco Inc. | Carbon dioxide-blown overbased calcium alkylphenolate lubricating compositions |
-
1984
- 1984-07-06 GB GB848417298A patent/GB8417298D0/en active Pending
-
1985
- 1985-06-17 CA CA000484252A patent/CA1255691A/en not_active Expired
- 1985-07-04 ZA ZA855047A patent/ZA855047B/en unknown
- 1985-07-04 JP JP14760685A patent/JPS6124561A/en active Granted
- 1985-07-04 BR BR8503202A patent/BR8503202A/en not_active IP Right Cessation
- 1985-07-04 DE DE8585201082T patent/DE3565258D1/en not_active Expired
- 1985-07-04 EP EP85201082A patent/EP0168110B1/en not_active Expired
-
1990
- 1990-02-05 SG SG67/90A patent/SG6790G/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2256441A (en) * | 1940-03-08 | 1941-09-16 | Socony Vacuum Oil Co Inc | Mineral oil composition and improving agent therefor |
| JPS60147497A (en) * | 1984-01-09 | 1985-08-03 | Cosmo Co Ltd | Preparation of salicylate-containing basic alkaline earth metal sulfide phenate type detergent |
| JPS60168793A (en) * | 1984-02-13 | 1985-09-02 | Cosmo Co Ltd | Production of basic sulfurized alkaline earth metal phenate detergent |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6364902U (en) * | 1986-10-16 | 1988-04-28 | ||
| JPH059522Y2 (en) * | 1986-10-16 | 1993-03-09 | ||
| JP2007039457A (en) * | 2005-07-29 | 2007-02-15 | Chevron Oronite Co Llc | Low-sulfur metal-based detergent-dispersant |
| JP2014001219A (en) * | 2005-07-29 | 2014-01-09 | Chevron Oronite Co Llc | Low-sulfur metal detergent-dispersants |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8503202A (en) | 1986-03-25 |
| JPH0580518B2 (en) | 1993-11-09 |
| GB8417298D0 (en) | 1984-08-08 |
| EP0168110B1 (en) | 1988-09-28 |
| EP0168110A1 (en) | 1986-01-15 |
| DE3565258D1 (en) | 1988-11-03 |
| SG6790G (en) | 1990-07-13 |
| ZA855047B (en) | 1986-02-26 |
| CA1255691A (en) | 1989-06-13 |
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