JPH0234692A - Manufacture of methyl ester - Google Patents
Manufacture of methyl esterInfo
- Publication number
- JPH0234692A JPH0234692A JP63183048A JP18304888A JPH0234692A JP H0234692 A JPH0234692 A JP H0234692A JP 63183048 A JP63183048 A JP 63183048A JP 18304888 A JP18304888 A JP 18304888A JP H0234692 A JPH0234692 A JP H0234692A
- Authority
- JP
- Japan
- Prior art keywords
- glycerin
- methanol
- methyl ester
- ch3oh
- topping
- 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
- 150000004702 methyl esters Chemical class 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 109
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 98
- 235000011187 glycerol Nutrition 0.000 claims abstract description 50
- 239000002253 acid Substances 0.000 claims abstract description 17
- 239000006227 byproduct Substances 0.000 claims abstract description 15
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 239000000344 soap Substances 0.000 claims abstract description 11
- 239000003921 oil Substances 0.000 claims description 24
- 239000003925 fat Substances 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 19
- 229930195729 fatty acid Natural products 0.000 abstract description 19
- 239000000194 fatty acid Substances 0.000 abstract description 19
- 150000004665 fatty acids Chemical class 0.000 abstract description 18
- 150000002148 esters Chemical class 0.000 abstract description 17
- 125000005456 glyceride group Chemical group 0.000 abstract description 4
- 238000011084 recovery Methods 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 3
- 238000007086 side reaction Methods 0.000 abstract description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 5
- 235000019198 oils Nutrition 0.000 description 23
- 235000019197 fats Nutrition 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000003240 coconut oil Substances 0.000 description 5
- 235000019864 coconut oil Nutrition 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000010446 mirabilite Substances 0.000 description 4
- 238000007670 refining Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000002314 glycerols Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- -1 Fatty acid esters Chemical class 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
ｌ果上夏肌理分災
本発明は油脂にメタノールをアルカリ触媒の存在下に反
応させてメチルエステルを製造する際に、副生ずる石鹸
を含むグリセリン液から色調の良いエステル、脂肪酸及
びグリセリンを高収率で回収できる効率の良いメチルエ
ステルの製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention produces esters with good color from a glycerin solution containing soap, which is produced as a by-product when producing methyl esters by reacting oils and fats with methanol in the presence of an alkaline catalyst. This invention relates to an efficient method for producing methyl esters that can recover fatty acids and glycerin in high yields.
盗沫ノｍ
第２図のメチルエステル化反応フロー概要に示すように
、アルカリ触媒を用いて油脂にメタノールを反応させて
メチルエステル化する工程においては、グリセリン液Ａ
が副生ずる。一般にこのグリセリン液Ａは、第１表に示
す組成を有するほぼ均一層で、波発生量は６６６ｋｇ／
１００１００Ｏ泊程度である。As shown in the outline of the methyl esterification reaction flow in Figure 2, in the process of reacting methanol with fats and oils to methyl esterify them using an alkaline catalyst, glycerin solution A
is a by-product. Generally, this glycerin solution A is a nearly uniform layer having the composition shown in Table 1, and the amount of waves generated is 666 kg/
It is about 100,100 nights.
従来、この副生グリセリン液Ａを精製してエステル、脂
肪酸及びグリセリンを回収することが行なわれており、
従来の回収方法としては上記グリセリン液Ａにまずメタ
ノールトッピング処理（脱メタノール処理）を施して、
第１表に示す組成のグリセリン液Ｂを得、更にこのグリ
セリン液Ｂを硫酸等で処理して石鹸成分等を酸分解し、
分離操作を施すことにより、第２表に示す組成の劣化油
Ｃと粗グリセリンＤを得、次いで粗生成物から各々劣化
油精製工程、グリセリン精製工程を経て。Conventionally, this by-product glycerin liquid A has been purified to recover esters, fatty acids, and glycerin.
As a conventional recovery method, the glycerin solution A is first subjected to methanol topping treatment (demethanol treatment),
A glycerin solution B having the composition shown in Table 1 is obtained, and this glycerin solution B is further treated with sulfuric acid or the like to acidically decompose soap components, etc.
By performing a separation operation, degraded oil C and crude glycerin D having the compositions shown in Table 2 were obtained, and then the crude products were subjected to a degraded oil refining step and a glycerin refining step, respectively.
精製油Ｆと精製グリセリンＥとを回収する方法が採用さ
れている。A method of recovering refined oil F and refined glycerin E is adopted.
が じようとする
しかしながら、メタノールトッピング処理後のグリセリ
ン液Ｂを酸分解するには、高温（１２０〜１３０℃）か
つ強酸性（ＰＨ２〜３）下で長時間（４０〜６０分）に
亘って酸処理することが必要であり、このため得られる
劣化油の色調が著しく悪化してしまうという欠点がある
。それ故、副生じたグリセリン液Ａ中のエステル、油分
９石鹸等の油脂分（含有率５．７％対油脂）は、分離後
に劣化油精製工程を経なければ、その再利用における用
途がかなり制限されてしまい、利用価値の低いものとな
る。However, acid decomposition of glycerin solution B after methanol topping treatment requires a long period of time (40 to 60 minutes) under high temperature (120 to 130°C) and strong acidity (PH 2 to 3). It is necessary to carry out acid treatment, which has the drawback that the color tone of the resulting degraded oil deteriorates significantly. Therefore, the oils and fats such as esters and oils and soaps (content 5.7% vs. oils and fats) in glycerin liquid A that are produced as by-products cannot be used for reuse unless they go through a degraded oil refining process after separation. It is restricted and has low utility value.
更に、メタノールトッピング時や酸分解時には、下記反
応式Ｉ、■で示されるような反応が進んでグリセライド
が副生じ、このため精製グリセリンＥの回収率が約１．
５％（対発生グリセリン）はど低下し、グリセリン回収
率が悪いという問題もある。Furthermore, during methanol topping or acid decomposition, the reaction shown in the following Reaction Formula I, (2) proceeds and glyceride is produced as a by-product, so that the recovery rate of purified glycerin E is about 1.
There is also the problem that the glycerin recovery rate is poor, with a decrease of 5% (based on glycerin generated).
く酸分解時刻反応式Ｉ〉
２Ｓ ０４
２ＲＣ０ＯＮａ＋Ｈ，ＳＯ４２ＲＣＯＯＨ＋Ｎａ２５ｏ
４〈メタノールトッピング時逆反応式■〉〔ＲはＣｎ
Ｈｚｎ＋ｘ （ｎ ＝５ ”’−２５）である。〕この
ように、アルカリ触媒を用いて油脂からメチルエステル
を製造する場合、従来の方法では。Citric acid decomposition time reaction formula I> 2S 04 2RC0ONa+H, SO42RCOOH+Na25o
4〈Reverse reaction formula when topping with methanol ■〉 [R is Cn
Hzn+x (n = 5''-25).] In this way, when producing methyl ester from fats and oils using an alkali catalyst, in the conventional method.
副生物を高品質で収率良く回収、利用することが困難で
、効率が低いものであった６
本発明は上記事情に鑑みなされたもので、副生ずるグリ
セリン液から色調の良いエステル、脂肪酸及びグリセリ
ンを収率良く回収することができる効率的なメチルエス
テルの製造方法を提供することを目的とする。It has been difficult to recover and utilize by-products with high quality and good yield, resulting in low efficiency.6 The present invention was made in view of the above circumstances, and it is possible to extract esters, fatty acids, and fatty acids with good color from glycerin liquid as a by-product. An object of the present invention is to provide an efficient method for producing methyl ester that can recover glycerin in good yield.
題を解 するための手 び作用
本発明者は、上記目的を達成するため鋭意検討を重ねた
結果、油脂からアルカリ触媒を用いてメチルエステルを
製造する方法において、副生ずる石鹸を含むグリセリン
液をメタノールトッピング処理前の過剰のメタノールを
含有する状態において７０℃以下の温度かつｐＨ９２〜
６の酸性条件下、約５〜１０分間の短時間で酸分解処理
し、次いでメタノールトッピング処理した場合、上記副
生グリセリン液から分離されるエステル及び脂肪酸の色
調悪化が可及的に防止され、色調が大幅に向上して、精
製工程を経なくても種々の用途に再使用し得る色調の良
いエステル及び脂肪酸を再生することができると共に、
上記酸分解時副反応Ｉ及びメタノールトッピング時逆反
応■をほぼ完全に抑制し得てグリセライドの副生を防止
でき、このため精製グリセリンを高収率で分離２回収で
きること、従って、副生グリセリン液中のエステル、脂
肪酸及びグリセリンの有効的な再利用が可能で、効率良
くメチルエステルを製造できることを知見し、本発明を
なすに至ったものである。In order to achieve the above object, the inventor of the present invention has made extensive studies and found that, in a method for producing methyl ester from fats and oils using an alkaline catalyst, a glycerin solution containing soap as a by-product is used. In a state containing excess methanol before methanol topping treatment, at a temperature of 70°C or less and a pH of 92 to
When the acid decomposition treatment is carried out for a short time of about 5 to 10 minutes under the acidic conditions of 6, and then the methanol topping treatment is carried out, deterioration of the color tone of the ester and fatty acid separated from the by-product glycerin liquid is prevented as much as possible, The color tone is greatly improved, and esters and fatty acids with good color can be reused for various purposes without going through a refining process.
The above-mentioned side reaction I during acid decomposition and reverse reaction II during methanol topping can be almost completely suppressed, and the by-product of glyceride can be prevented. Therefore, purified glycerin can be separated and recovered in high yield. It was discovered that the esters, fatty acids, and glycerin contained therein can be effectively reused and methyl esters can be produced efficiently, leading to the present invention.
以下、本発明につき更に詳述する。The present invention will be explained in more detail below.
本発明のメチルエステルの製造方法は、上述したように
油脂にメタノールをアルカリ触媒の存在下に反応させて
メチルエステルを装造する方法において、副生ずる石鹸
を含むグリセリン液をメタノールトッピング処理前の過
剰のメタノールを含有する状態において７０℃以下の温
度かつ酸性条件下で触分解処理し、次いでメタノールト
ッピング処理するものである。The method for producing methyl ester of the present invention is to prepare a methyl ester by reacting methanol with fats and oils in the presence of an alkali catalyst as described above. The method involves catalytic decomposition treatment under acidic conditions at a temperature of 70° C. or less in a state containing methanol, followed by methanol topping treatment.
この場合、油脂からメチルエステルを製造する方法とし
ては、第１図のフロー概要に示すように、油脂に対して
メタノールとアルカリ触媒を添加し、アルカリエステル
化反応を進めた後に得られるメチルエステルを分離する
という操作を繰り返すといった通常の方法を採用するこ
とができる。In this case, the method for producing methyl ester from fats and oils is to add methanol and an alkali catalyst to fats and oils, proceed with the alkaline esterification reaction, and then produce the methyl ester, as shown in the flow outline in Figure 1. A normal method such as repeating the separation operation can be adopted.
ここで、原料の油脂には、種々のものを使用し得、具体
的にはパーム油、ヤシ油、パーム核油等の植物油、牛脂
、豚脂等の動物油が例示される。Here, various kinds of fats and oils can be used as the raw material, and specific examples include vegetable oils such as palm oil, coconut oil, and palm kernel oil, and animal oils such as beef tallow and lard.
また、アルカリ触媒としては、例えばＮ ａ ＯＨ。Further, as the alkali catalyst, for example, N a OH.
ＫＯＨ，Ｎａ、ＣＯ２等を用いることができる。KOH, Na, CO2, etc. can be used.
なお、原料油脂へのメタノール及びアルカリ触媒の添加
量は、別に限定されないが、通常油脂全体に対してメタ
ノールは５〜４ｏ％（重量％、以下同様）、アルカリ触
媒は０．１〜０．４％が好適である。Note that the amounts of methanol and alkali catalyst added to the raw material fats and oils are not particularly limited, but usually methanol is 5 to 4% (wt%, hereinafter the same) to the whole fat and oil, and the alkali catalyst is 0.1 to 0.4%. % is preferred.
更に、反応条件は適宜調整し得るが、反応温度６０〜７
０℃、時間５〜６０分が望ましい。Furthermore, although the reaction conditions can be adjusted as appropriate, the reaction temperature is 60 to 7
Preferably, the temperature is 0°C and the time is 5 to 60 minutes.
本発明では、上記メチルエステルの製造工程において、
第１図に示すようにメチルエステル分離時に副生ずるグ
リセリン液Ａ′をまず酸分解し。In the present invention, in the manufacturing process of the above methyl ester,
As shown in FIG. 1, the glycerin solution A' produced as a by-product during methyl ester separation is first decomposed with acid.
その後にメタノールトッピング（脱メタノール）処理を
施し、エステル、脂肪酸と粗グリセリンとを分離９回収
するものである。Thereafter, methanol topping (demethanol removal) treatment is performed to separate and recover esters, fatty acids, and crude glycerin.
ここで、グリセリン液は、成分中のメタノールの除去処
理をせずに過剰のメタノールを含有する状態のままで酸
分解処理するもので、その酸分解処理は、例えば硫酸、
塩酸、リン酸等の酸を添加して、好ましくはＰＨ２〜６
、より好ましくはｐＨ５〜６の条件下で行なう。なお、
酸の添加量は、酸性液となる限りにおいて適宜調整する
ことができる。Here, the glycerin solution is subjected to acid decomposition treatment while still containing excess methanol without removing methanol from its components.
Add an acid such as hydrochloric acid or phosphoric acid to preferably adjust the pH to 2 to 6.
, more preferably under conditions of pH 5 to 6. In addition,
The amount of acid added can be adjusted as appropriate as long as the resulting solution is acidic.
更に、酸分解は７０’Ｃ以下、好ましくは１ｏ〜７０℃
、より好ましくは３０〜５０’Ｃの温度で短時間、好ま
しくは５〜１０分間で行なう。Furthermore, the acid decomposition temperature is below 70'C, preferably from 1o to 70°C.
, more preferably at a temperature of 30-50'C for a short time, preferably 5-10 minutes.
次いで、酸分解後は、析出した芒硝等の不溶化物を分離
、除去し、メタノールトッピング処理を行なう。Next, after acid decomposition, precipitated insolubilized substances such as Glauber's salt are separated and removed, and methanol topping treatment is performed.
メタノールトッピングは、グリセリン液中からメタノー
ルを除去することができれば良く、常法に準じて行なう
。Methanol topping may be performed as long as methanol can be removed from the glycerin solution, and may be performed according to a conventional method.
更に、メタノール処理後は、処理液を通常の方法で分離
することで、エステル、脂肪酸と粗グリセリンとを回収
することができる。Further, after the methanol treatment, the ester, fatty acid, and crude glycerin can be recovered by separating the treatment liquid using a conventional method.
なお、粗グリセリンは、精製した後に再利用することが
好ましいが、エステル、脂肪酸は、精製工程を行なわず
にそのまま再利用することができる。Note that crude glycerin is preferably reused after being purified, but esters and fatty acids can be reused as they are without performing a purification step.
本発明では、石鹸を含むグリセリン液をメタノールトッ
ピング処理前の過剰ａメタノールを含有する状態で酸分
解処理することにより、低温かつ酸性条件下で短時間の
うちに酸分解処理できるもので、この場合、メタノール
５０％、グリセリン２０％、水２３％、エステル類３％
２石＃Ｌ４％等を含有するグリセリン液において、以下
のような現象が生じ、本発明の目的を達成することがで
きるものである。なお、下記は酸として硫酸を用いた場
合を示す。In the present invention, the acid decomposition treatment can be performed in a short time under low temperature and acidic conditions by subjecting the glycerin solution containing soap to the acid decomposition treatment in a state containing excess a-methanol before the methanol topping treatment. , methanol 50%, glycerin 20%, water 23%, esters 3%
In a glycerin solution containing 2 stones #L4%, etc., the following phenomenon occurs, and the object of the present invention can be achieved. In addition, the following shows the case where sulfuric acid is used as the acid.
（イ）石鹸は、下記に示す反応に従って低温がっ短時間
で分解する。(a) Soap decomposes in a short time at low temperatures according to the reaction shown below.
２ＲＣ０ＯＮａ＋Ｈ，５Ｏ４−ｍ−÷２Ｎａ、ＳＯ，＋
ＲＣＯＯＨ（ロ）石鹸分解により得られた脂肪酸は、過
剰メタノール中でメチルエステル化する速度が早く、こ
のためグリセライドの生成が抑えられる。2RC0ONa+H,5O4-m-÷2Na,SO,+
RCOOH (b) Fatty acids obtained by soap decomposition are rapidly converted into methyl esters in excess methanol, thereby suppressing the production of glycerides.
（ハ）芒硝は、過剰メタノール中で不溶化し、析出する
ので、分離すればその後のメタノールトッピングで析出
しない。(c) Glauber's salt is insolubilized and precipitated in excess methanol, so if it is separated, it will not precipitate in the subsequent methanol topping.
（ニ）脂肪酸エステルは、低温での反応のために色調向
上がある。(d) Fatty acid esters improve color tone due to their reaction at low temperatures.
（ホ）石鹸を含まない系（グリセリン−水−油一メタノ
ール）であるため、メタノール除去が簡単になる。(e) Since the system does not contain soap (glycerin-water-oil-methanol), methanol removal becomes easy.
（へ）低濃度グリセリン（２０％）で芒硝除去を行なう
ので、廃棄芒硝中のグリセリンロスの低減になる。(f) Since mirabilite is removed using low concentration glycerin (20%), glycerin loss in waste mirabilite is reduced.
発明の効果
本発明のメチルエステルの製造方法によれば、副生ずる
石鹸を含むグリセリン液から精製工程を経ずに良好な色
調を有するエステル、脂肪酸を再生することができると
共に、精製グリセリンを高収率で回収することができ、
しかもこれらの回収したエステル、脂肪酸及びグリセリ
ンは幅広い用途に再利用することができる。従って１本
発明のメチルエステルの製造方法は、非常に効率が良い
ものである。Effects of the Invention According to the method for producing methyl ester of the present invention, it is possible to regenerate esters and fatty acids with good color tone from a glycerin solution containing by-product soap without going through a purification process, and it is also possible to regenerate purified glycerin in high yield. can be recovered at a rate of
Moreover, these recovered esters, fatty acids, and glycerin can be reused for a wide range of purposes. Therefore, the method for producing methyl ester of the present invention is very efficient.
以下に実施例及び比較例を挙げて本発明を具体的に説明
するが１本発明は下記実施例に制限されるものではない
。The present invention will be specifically described below with reference to Examples and Comparative Examples, but the present invention is not limited to the following Examples.
本性（第１図）に準じ、油脂としてヤシ油を用い、ヤシ
油１０００部に対してメタノール３５０部及びアルカリ
３．５部を添加してアルカリエステル化処理を行ない、
副生じたグリセリン液をｐＨ５，５，２５℃の条件下で
５分間酸分解し、エステル及び脂肪酸（油分）と精製グ
リセリンを再生した（実施例）。According to the nature (Fig. 1), coconut oil was used as the oil and fat, and 350 parts of methanol and 3.5 parts of alkali were added to 1000 parts of coconut oil to perform alkali esterification treatment.
The by-produced glycerin solution was subjected to acid decomposition under conditions of pH 5, 5, and 25° C. for 5 minutes to regenerate esters, fatty acids (oil), and purified glycerin (Example).
また、同様にヤシ油を旧法（第２図）に準じて所定の条
件で処理し、再生物を得た（比較例）。In addition, coconut oil was similarly treated under predetermined conditions according to the old method (Figure 2) to obtain a regenerated product (comparative example).
上記実施例及び比較例で再生物として得られた油の色調
及び反応グリセリン分を４Ｉす定したところ、第３表の
結果を得た。When the color tone and reactive glycerin content of the oils obtained as recycled products in the above Examples and Comparative Examples were determined as 4I, the results shown in Table 3 were obtained.
第３表
注１）各油４ｇを１０ｍＱ四塩化炭素に溶解し、４２０
−で吸光度を測定した。Table 3 Note 1) Dissolve 4g of each oil in 10mQ carbon tetrachloride,
- The absorbance was measured at -.
注２）各油中の反応グリセリン分を測定した。４％差分
はヤシ油理論グリセリン発生量の１．５％に相当する。Note 2) The reactive glycerin content in each oil was measured. A 4% difference corresponds to 1.5% of the theoretical amount of glycerin generated in coconut oil.
第３表の結果より、本発明の製造方法によれば、良好な
色調の油（エステル、脂肪酸）を得ることができ、かつ
精製グリセリンを高収率で回収できることが確認された
。From the results in Table 3, it was confirmed that according to the production method of the present invention, oils (esters, fatty acids) with good color tone could be obtained, and purified glycerin could be recovered in high yield.
第１図は本発明製造方法に係る油脂からメチルエステル
化反応を示す工程図、第２図は、従来の製造方法におい
ての油脂、メチルエステル化反応フローを示す概略図で
ある。
出願人 ラ イ オ ン 株式会社
代理人 弁理士 小 島 隆 司FIG. 1 is a process diagram showing the methyl esterification reaction from fats and oils according to the production method of the present invention, and FIG. 2 is a schematic diagram showing the flow of the methyl esterification reaction from fats and oils in the conventional production method. Applicant Lion Co., Ltd. Agent Patent Attorney Takashi Kojima
Claims (1)
せてメチルエステルを製造する方法において、副生する
石鹸を含むグリセリン液をメタノールトッピング処理前
の過剰のメタノールを含有する状態において７０℃以下
の温度かつ酸性条件下で酸分解し、次いでメタノールト
ッピング処理することを特徴とするメチルエステルの製
造方法。1. In a method for producing methyl ester by reacting methanol with fats and oils in the presence of an alkali catalyst, the glycerin solution containing by-product soap is heated to a temperature of 70°C or less in a state containing excess methanol before methanol topping treatment. A method for producing methyl ester, which comprises acid decomposition under acidic conditions and then methanol topping treatment.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63183048A JP2590538B2 (en) | 1988-07-22 | 1988-07-22 | Method for producing methyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63183048A JP2590538B2 (en) | 1988-07-22 | 1988-07-22 | Method for producing methyl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0234692A true JPH0234692A (en) | 1990-02-05 |
| JP2590538B2 JP2590538B2 (en) | 1997-03-12 |
Family
ID=16128832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63183048A Expired - Lifetime JP2590538B2 (en) | 1988-07-22 | 1988-07-22 | Method for producing methyl ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2590538B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06184024A (en) * | 1992-12-15 | 1994-07-05 | Kao Corp | Production of glycerol |
| WO2006129435A1 (en) * | 2005-06-03 | 2006-12-07 | Lion Corporation | Process for producing lower alkyl ester of fatty acid, lower alkyl ester of fatty acid, and substitute fuel for gas oil |
| WO2007074592A1 (en) * | 2005-12-27 | 2007-07-05 | Lion Corporation | Process for producing lower alkyl ester of fatty acid |
| WO2010129809A3 (en) * | 2009-05-06 | 2011-04-14 | S.I.I., Llc | Glycerin purification |
| WO2021193887A1 (en) * | 2020-03-25 | 2021-09-30 | バイオ燃料技研工業株式会社 | Method for producing biodiesel fuel |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100930050B1 (en) | 2008-03-03 | 2009-12-08 | (주)동양유지 | Purification technology of glycerin, a biodiesel by-product |
-
1988
- 1988-07-22 JP JP63183048A patent/JP2590538B2/en not_active Expired - Lifetime
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06184024A (en) * | 1992-12-15 | 1994-07-05 | Kao Corp | Production of glycerol |
| WO2006129435A1 (en) * | 2005-06-03 | 2006-12-07 | Lion Corporation | Process for producing lower alkyl ester of fatty acid, lower alkyl ester of fatty acid, and substitute fuel for gas oil |
| JP4920583B2 (en) * | 2005-06-03 | 2012-04-18 | ライオン株式会社 | Fatty acid lower alkyl ester and light oil alternative fuel |
| KR101234969B1 (en) * | 2005-06-03 | 2013-02-20 | 라이온 가부시키가이샤 | Process for producing lower alkyl ester of fatty acid, lower alkyl ester of fatty acid, and substitute fuel for gas oil |
| WO2007074592A1 (en) * | 2005-12-27 | 2007-07-05 | Lion Corporation | Process for producing lower alkyl ester of fatty acid |
| JP5005547B2 (en) * | 2005-12-27 | 2012-08-22 | ライオン株式会社 | Method for producing fatty acid lower alkyl ester |
| WO2010129809A3 (en) * | 2009-05-06 | 2011-04-14 | S.I.I., Llc | Glycerin purification |
| WO2021193887A1 (en) * | 2020-03-25 | 2021-09-30 | バイオ燃料技研工業株式会社 | Method for producing biodiesel fuel |
| JPWO2021193887A1 (en) * | 2020-03-25 | 2021-09-30 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2590538B2 (en) | 1997-03-12 |
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