JP6844981B2 - Neutralization method of acidic oil and oil with reduced corrosiveness - Google Patents
Neutralization method of acidic oil and oil with reduced corrosiveness Download PDFInfo
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- 230000002378 acidificating effect Effects 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 23
- 238000006386 neutralization reaction Methods 0.000 title description 13
- 150000001412 amines Chemical class 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 230000003472 neutralizing effect Effects 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 7
- 150000003141 primary amines Chemical class 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 4
- 230000002209 hydrophobic effect Effects 0.000 claims description 4
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003921 oil Substances 0.000 description 46
- 235000019198 oils Nutrition 0.000 description 46
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 14
- 238000005260 corrosion Methods 0.000 description 11
- 230000007797 corrosion Effects 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- 229910052742 iron Inorganic materials 0.000 description 7
- 238000000197 pyrolysis Methods 0.000 description 7
- 239000002699 waste material Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000295 fuel oil Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical group C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 230000001603 reducing effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- -1 that is Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005536 corrosion prevention Methods 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- 238000004231 fluid catalytic cracking Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
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- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Description
本発明は、酸性油の中和方法、及び該方法によって得られる腐食性が低減した油に関する。 The present invention relates to a method for neutralizing an acidic oil and an oil having reduced corrosiveness obtained by the method.
現在、広く工業界で用いられている化石原料、特に石炭・石油系の原料油は、昨今の不安定な世界情勢や将来における埋蔵量を考慮すると、その供給が長期に亘って安定であるとは言えず、代替原料等の検討が行われてきた。
例えば非化石原料、即ち動植物油又はその改質品に関する検討が行われており、タイヤの原料等の広い分野に応用されている。また、ナフテン酸等の有機酸を含む低品質の重質油、高分子廃棄物である廃プラスチックや廃ゴムなどを不活性雰囲気下で熱分解することにより得られる熱分解油の利用の検討も行われており、マテリアルリサイクルの面からもより環境に配慮した手法として注目されている。
しかし、上記重質油や一部の熱分解油は酸性物質を多く含有することから、熱交換器、受入タンク、配管等の各種設備に対して強い腐食性を有するため、機器の損耗、破壊を引き起こすといった問題がある。
The supply of fossil raw materials widely used in the industry at present, especially coal and petroleum-based raw materials, is said to be stable for a long period of time in view of the recent unstable world situation and future reserves. However, alternative raw materials have been studied.
For example, studies have been conducted on non-fossil raw materials, that is, animal and vegetable oils or modified products thereof, and they are applied to a wide range of fields such as tire raw materials. We are also considering the use of pyrolysis oil obtained by thermally decomposing low-quality heavy oil containing organic acids such as naphthenic acid, waste plastics and waste rubber, which are polymer wastes, in an inert atmosphere. It is being carried out and is attracting attention as a more environmentally friendly method from the aspect of material recycling.
However, since the above-mentioned heavy oil and some pyrolysis oils contain a large amount of acidic substances, they are highly corrosive to various equipment such as heat exchangers, receiving tanks, and piping, so that the equipment is worn or destroyed. There is a problem such as causing.
これらの問題に対し、種々の化合物による中和反応を利用した腐食の低減が検討されており、リン酸化合物（特許文献１）、チオール類（特許文献２）、各種アミン（特許文献３）等が報告されている。
しかし、これらの技術には様々な問題があり、例えばリン酸化合物は毒性が高く、取扱いに制限が生じるといった問題があるし、チオール類の腐食低減効果は十分でなく、且つ比較的処理時間が長いため、効率的な手法とは言えない。また、各種アミンは種々の形態があるため広く検討されており、シクロヘキシルアミン、トリブチルアミン等が取り上げられているが、やはり腐食低減効果が不十分な事例が多く、そのため多量に用いる必要があって効率的でない。また、手法によっては水溶液添加であるため油水分離工程が必要であり、更なる改良が求められている。
To solve these problems, reduction of corrosion by utilizing a neutralization reaction with various compounds has been studied, and phosphoric acid compounds (Patent Document 1), thiols (Patent Document 2), various amines (Patent Document 3), etc. Has been reported.
However, these techniques have various problems, for example, phosphoric acid compounds are highly toxic and have problems in handling, the corrosion reducing effect of thiols is not sufficient, and the treatment time is relatively long. It is not an efficient method because it is long. In addition, various amines have been widely studied because they have various forms, and cyclohexylamine, tributylamine, etc. have been taken up, but there are many cases where the corrosion reducing effect is insufficient, and therefore it is necessary to use a large amount. Inefficient. Further, depending on the method, an oil-water separation step is required because the aqueous solution is added, and further improvement is required.
本発明は、酸性油の簡便かつ効果的な中和方法、及び該方法によって得られる腐食性が低減した油の提供を目的とする。 An object of the present invention is to provide a simple and effective neutralization method for an acidic oil, and an oil having reduced corrosiveness obtained by the method.
本発明者らは、酸性物質を多く含有する所謂酸性油の効率的な中和方法について検討した結果、特定の化学構造及び物性を備えたアミンを用いると、従来の中和方法に見られる加熱や加圧、及び油水分離工程が不要となり、また、酸性油に対し油中の酸と等しい化学当量のアミンを添加するだけで十分に腐食性が低減した油が得られることを見出した。
即ち、上記課題は、次の１）〜４）の発明によって解決される。
１） 酸性油に対し、分子内に脂環式の６員環を２つ有し、疎水性で沸点が１００℃以上の一級アミンを添加することを特徴とする酸性油の中和方法。
２） 前記アミンが、４，４′−メチレンビス（シクロヘキシルアミン）、又は、４，４′−メチレンビス（２−メチルシクロヘキシルアミン）であることを特徴とする１）に記載の酸性油の中和方法。
３） 酸性油中の酸と等しい化学当量のアミンを添加することを特徴とする１）又は２）に記載の酸性油の中和方法。
４） １）〜３）のいずれかに記載の酸性油の中和方法によって得られる腐食性が低減した油。
As a result of investigating an efficient neutralization method for so-called acidic oil containing a large amount of acidic substances, the present inventors have found that when an amine having a specific chemical structure and physical properties is used, the heating seen in the conventional neutralization method is used. It has been found that the steps of pressurization, pressurization, and oil-water separation are not required, and that an oil having sufficiently reduced corrosiveness can be obtained simply by adding an amine having a chemical equivalent equivalent to the acid in the oil to the acidic oil.
That is, the above problems are solved by the following inventions 1) to 4).
1) A method for neutralizing an acidic oil, which comprises adding a primary amine having two alicyclic 6-membered rings in the molecule, which is hydrophobic and has a boiling point of 100 ° C. or higher, with respect to the acidic oil.
2) The method for neutralizing an acidic oil according to 1), wherein the amine is 4,4'-methylenebis (cyclohexylamine) or 4,4'-methylenebis (2-methylcyclohexylamine). ..
3) The method for neutralizing an acidic oil according to 1) or 2), which comprises adding an amine having a chemical equivalent equivalent to that of the acid in the acidic oil.
4) An oil with reduced corrosiveness obtained by the method for neutralizing an acidic oil according to any one of 1) to 3).
本発明によれば、酸性油の簡便かつ効果的な中和方法を提供できるとともに、該手法により腐食性が低減した油を得ることができる。また、各種設備に腐食対策を行うことなく熱分解油などの酸性油を用いることが可能となり、マテリアルサイクルの構築や安定した原料供給を実現できるので、工業上極めて有用である。 According to the present invention, it is possible to provide a simple and effective neutralization method for acidic oils, and it is possible to obtain oils with reduced corrosiveness by this method. In addition, it is possible to use acidic oil such as pyrolysis oil for various equipment without taking measures against corrosion, and it is possible to construct a material cycle and stably supply raw materials, which is extremely useful in industry.
以下、本発明について詳しく説明する。
本発明の対象となる酸性油とは酸性物質を含有する油のことであり、その例としては、ナフテン酸等の有機酸を含む低品質の重質油、廃プラスチックや廃ゴムを不活性雰囲気下で熱分解することにより得られる熱分解油の一部などが挙げられる。これらの油は酸性物質を多く含有することから、熱交換器、受入タンク、配管等の各種設備に対して強い腐食性を有し、機器の損耗、破壊を引き起こすため、酸性物質を中和する必要がある。
Hereinafter, the present invention will be described in detail.
The acidic oil which is the subject of the present invention is an oil containing an acidic substance, and examples thereof include low-quality heavy oil containing an organic acid such as naphthenic acid, waste plastic and waste rubber in an inert atmosphere. A part of the pyrolysis oil obtained by thermally decomposing below can be mentioned. Since these oils contain a large amount of acidic substances, they are highly corrosive to various equipment such as heat exchangers, receiving tanks, and piping, and cause wear and tear of the equipment, thus neutralizing the acidic substances. There is a need.
本発明では中和用のアミンとして、分子内に脂環式の６員環を２つ有し、疎水性で沸点が１００℃以上の一級アミンを用いる。その例としては、４，４′−メチレンビス（シクロヘキシルアミン）、４，４′−メチレンビス（２−メチルシクロヘキシルアミン）などが挙げられる。
なお、「疎水性」とは、分子構造等に由来して、水に対する親和性が低く混和しにくい性質のことであるが、一般的には水に対する溶解度が１ｇ／１００ｍＬ以下程度の物質を疎水性物質と呼んでいる。
一級アミンを用いると高い中和効果が得られるのは、立体障害が少なく中和反応が速やかに進行するためであると考えられる。また、分子内に脂環式の６員環を２つ有するアミンは、酸性油との親和性が高く容易に分散するので、腐食原因物質の酸との反応が効率よく進行すると推測される。更に、沸点が１００℃以上であると、高温条件での中和反応に耐えることができるし、工業プラントでは重質油が１００℃近い温度で保管されていることも考慮すると、沸点が１００℃以上であることが好ましい。なお、沸点の上限は特にないが、実用可能な一級アミンの沸点は最高でも４００℃程度である。
In the present invention, as the amine for neutralization, a primary amine having two alicyclic 6-membered rings in the molecule, which is hydrophobic and has a boiling point of 100 ° C. or higher is used. Examples thereof include 4,4'-methylenebis (cyclohexylamine) and 4,4'-methylenebis (2-methylcyclohexylamine).
In addition, "hydrophobicity" is a property that has low affinity for water and is difficult to mix due to its molecular structure, etc., but in general, a substance having a solubility in water of about 1 g / 100 mL or less is hydrophobic. We call it a sex substance.
It is considered that the high neutralization effect can be obtained by using the primary amine because the steric hindrance is small and the neutralization reaction proceeds rapidly. Further, since an amine having two alicyclic 6-membered rings in the molecule has a high affinity with an acidic oil and is easily dispersed, it is presumed that the reaction of the corrosion-causing substance with the acid proceeds efficiently. Further, when the boiling point is 100 ° C. or higher, the neutralization reaction under high temperature conditions can be withstood, and considering that heavy oil is stored at a temperature close to 100 ° C. in an industrial plant, the boiling point is 100 ° C. The above is preferable. Although there is no particular upper limit on the boiling point, the boiling point of a practical primary amine is about 400 ° C. at the maximum.
本発明における中和操作は、油の流動性が保たれ均一な反応が進行するように留意すること以外に特に留意点はなく、アミンを適宜混合撹拌すればよい。
具体的には、まず中和対象となる酸性油に含まれる酸の量〔ＴＡＮ（全酸価）値〕を測定する。測定方法は公知の方法、例えば全酸価測定法（ＪＩＳ Ｋ２５０１）などを採用すればよい。
次いで、適当な反応容器に酸性油を入れ、そこに酸性油中の酸と等しい化学当量のアミンを添加して十分に混合撹拌する。混合撹拌の時間は酸性油の量などに応じて変わるので特定できないが、要するに酸とアミンの中和反応が完了すればよく、通常は１〜２分程度である。なお、上記「酸性油中の酸と等しい化学当量」とは、化学量論的に厳密に等しい量である必要はなく、実際の操作では多少の増減は問題ない。しかしアミンを過剰に添加すればアミンが無駄になるし、アミンが少なすぎると中和されない酸が増えて十分な腐食防止効果が得られない惧れもあるので、できるだけ「酸性油中の酸と等しい化学当量」とすることが好ましい。
そして、後述する実施例、比較例から分かるように、本発明に係る一級アミンの場合は顕著な効果が得られるが、比較例で用いたアミンでは酸と等しい量を加えても腐食を防止することはできない。
In the neutralization operation in the present invention, there are no particular points to be noted except that the fluidity of the oil is maintained and a uniform reaction proceeds, and amines may be appropriately mixed and stirred.
Specifically, first, the amount of acid [TAN (total acid value) value] contained in the acidic oil to be neutralized is measured. As the measuring method, a known method, for example, a total acid value measuring method (JIS K2501) or the like may be adopted.
Then, an acidic oil is placed in a suitable reaction vessel, a chemical equivalent of amine equal to the acid in the acidic oil is added thereto, and the mixture is sufficiently mixed and stirred. The mixing and stirring time cannot be specified because it changes depending on the amount of acidic oil and the like, but in short, it suffices if the neutralization reaction between the acid and the amine is completed, and it is usually about 1 to 2 minutes. The above-mentioned "chemical equivalent equivalent to the acid in the acidic oil" does not have to be an amount that is strictly stoichiometrically equal, and there is no problem in actual operation. However, if an excessive amount of amine is added, the amine will be wasted, and if the amount of amine is too small, the amount of unneutralized acid may increase and a sufficient corrosion prevention effect may not be obtained. It is preferable that the chemical equivalents are equal.
As can be seen from Examples and Comparative Examples described later, a remarkable effect can be obtained in the case of the primary amine according to the present invention, but the amine used in the Comparative Example prevents corrosion even when an amount equal to that of the acid is added. It is not possible.
以下、実施例及び比較例を示して本発明を更に具体的に説明するが、本発明はこれらの実施例により限定されるものではない。 Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.
実施例１〜２、比較例１〜７
廃ゴム１、及び廃ゴム２を、ロータリーキルン内で６００℃×２時間加熱処理した後、軽質分を抜いて熱分解油１（ＴＡＮ値：１１．５）、熱分解油２（ＴＡＮ値：０．５８）を得た。
また、ＦＣＣ油（流動接触分解油）に、ナフタレンカルボン酸とシクロヘキサンカルボン酸を加えてＴＡＮ値を調整し、酸性油１（ＴＡＮ値：７．１）、酸性油２（ＴＡＮ値：２．２）を得た。
また、課粒状のポリスチレン（ＰＳ）とポリエチレンテレフタレート（ＰＥＴ）の重量比５：１の混合物を熱分解して、ＰＳ／ＰＥＴ熱分解油（ＴＡＮ値：２０．５）を得た。
上記各酸性油を用い、表１の実施例１〜２の一級アミン、及び、比較例１〜６の各欄に示すアミン（本発明の条件を一つ以上満たさないアミン）を用いて中和反応を行った後、鉄片を用いて腐食の程度を調べた。
まず、全酸価測定法（ＪＩＳ Ｋ２５０１）により各酸性油中の酸の量を測定した。
次いで、５０ｍＬのガラス瓶に各酸性油を３０ｇ入れ、該油中の酸と等しい化学当量のアミンを添加して十分に混合撹拌した。得られた混合物に鉄片（２０ｍｍ×２４ｍｍ×３ｍｍ）を浸漬した後、ガラス瓶ごとオイルバスで９０℃×４５日間加熱した。
その後、鉄片を取り出し、油分を除去し洗浄した後、重量を測定し、下記式により重量減少率を算出した。
また、比較例７として、アミンを添加することなく同様にテストを行った。
結果を表１に示すが、重量減少率が大きい程、鉄片の腐食が進行していることになる。
重量減少率（％）＝〔（浸漬前鉄片重量−浸漬後鉄片重量）／浸漬前鉄片重量〕×１００
Examples 1-2, Comparative Examples 1-7
Waste rubber 1 and waste rubber 2 are heat-treated in a rotary kiln at 600 ° C. for 2 hours, and then the light components are removed to remove pyrolysis oil 1 (TAN value: 11.5) and pyrolysis oil 2 (TAN value: 0). .58) was obtained.
Further, naphthalenecarboxylic acid and cyclohexanecarboxylic acid were added to FCC oil (fluid catalytic cracking oil) to adjust the TAN value, and acidic oil 1 (TAN value: 7.1) and acidic oil 2 (TAN value: 2.2) were adjusted. ) Was obtained.
Further, a mixture of polystyrene (PS) and polyethylene terephthalate (PET) having a weight ratio of 5: 1 was thermally decomposed to obtain PS / PET pyrolysis oil (TAN value: 20.5).
Neutralize with each of the above acidic oils using the primary amines of Examples 1 and 2 in Table 1 and the amines shown in the columns of Comparative Examples 1 to 6 (amines that do not satisfy one or more of the conditions of the present invention). After the reaction was carried out, the degree of corrosion was examined using iron pieces.
First, the amount of acid in each acidic oil was measured by the total acid value measurement method (JIS K2501).
Next, 30 g of each acidic oil was placed in a 50 mL glass bottle, a chemical equivalent of amine equal to the acid in the oil was added, and the mixture was sufficiently mixed and stirred. After immersing an iron piece (20 mm × 24 mm × 3 mm) in the obtained mixture, the whole glass bottle was heated in an oil bath at 90 ° C. × 45 days.
Then, the iron piece was taken out, the oil content was removed and washed, and then the weight was measured, and the weight loss rate was calculated by the following formula.
Moreover, as Comparative Example 7, the same test was carried out without adding amine.
The results are shown in Table 1. The larger the weight loss rate, the more the iron pieces are corroded.
Weight reduction rate (%) = [(Weight of iron piece before immersion-Weight of iron piece after immersion) / Weight of iron piece before immersion] x 100
表１から分かるように、実施例の減少率は、どの酸性油についても０％であり、腐食が全く生じなかった。これに対し比較例では、効果にバラツキがあるものの、いずれも腐食低減効果は不十分であった。
なお、アミンを添加しない比較例７よりも腐食が進行した比較例があるが、これは、各アミンに特有の腐食に対する悪影響によるものと推測される。つまり、アミンによる中和反応が常に腐食に対してプラスの効果があるわけではなく、アミンの種類によっては却って悪影響を及ぼす場合もあり、アミンの選択は非常に重要且つ微妙であることが分かる。
As can be seen from Table 1, the reduction rate of the examples was 0% for all acidic oils, and no corrosion occurred. On the other hand, in the comparative examples, although the effects varied, the corrosion reduction effect was insufficient in all cases.
In addition, there is a comparative example in which corrosion progressed more than in Comparative Example 7 to which no amine was added, but it is presumed that this is due to an adverse effect on corrosion peculiar to each amine. In other words, it can be seen that the neutralization reaction with amines does not always have a positive effect on corrosion, and depending on the type of amine, it may have an adverse effect on the contrary, and the selection of amines is very important and delicate.
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