JPH0228397B2 - - Google Patents
Info
- Publication number
- JPH0228397B2 JPH0228397B2 JP7162285A JP7162285A JPH0228397B2 JP H0228397 B2 JPH0228397 B2 JP H0228397B2 JP 7162285 A JP7162285 A JP 7162285A JP 7162285 A JP7162285 A JP 7162285A JP H0228397 B2 JPH0228397 B2 JP H0228397B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- reaction
- added
- lactam
- raw water
- 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 20
- 238000000855 fermentation Methods 0.000 claims description 10
- 230000004151 fermentation Effects 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 10
- 150000003951 lactams Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000010802 sludge Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 230000029087 digestion Effects 0.000 description 3
- 239000010800 human waste Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000002309 gasification Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- ZVNUABIDENQZES-UHFFFAOYSA-N 1-(3-phenylpropanoyl)piperidin-2-one Chemical compound C1CCCC(=O)N1C(=O)CCC1=CC=CC=C1 ZVNUABIDENQZES-UHFFFAOYSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical class ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salts Chemical class 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/30—Fuel from waste, e.g. synthetic alcohol or diesel
Landscapes
- Purification Treatments By Anaerobic Or Anaerobic And Aerobic Bacteria Or Animals (AREA)
- Treatment Of Sludge (AREA)
Description
本発明はメタン醗酵促進剤に関する。
石油シヨツク以降、農畜、林産廃棄物、食生活
廃棄物等廃棄物の浄化と同時に熱エネルギー源と
しての回収法としてのメタン醗酵が注目されてい
る。
殊に、し尿、下水処理施設の普及に伴つて、高
濃度処理が可能であり、汚泥発生量が少ない等の
利点を有する嫌気性消化処理法が発達している
が、反面、消化温度を高さるため加温を必要と
し、消化期間や長期間に及ぶなどの欠点を有す
る。
例えば、ある嫌気性消化試験では、10℃ではガ
ス化が90％進行するに90日を要し、30℃では28
日、また、汚泥グラム当り、ガス発生量は10℃で
450mlに対し、30℃では760mlを極めて温度依存性
が高く、従つて実操業では30〜40℃で行われ、ま
た消化日数も通常20〜30日を要している。
このような現状に鑑み、常温に於ては勿論、低
温に於てもガス化速度が大きく、メタンガス発生
量を増加させる方法について、種々検討を行つた
結果、以下に詳記する本発明を完成したものであ
る。
即ち、本発明は
一般式
（但し、Ｒは−CH2−、−CH2−CH2−、または
−CH＝CH−を示し、ｎ＝３〜５である）で示
されるＮ−アシルラクタム類化合物からなるメタ
ン醗酵促進剤に関する。
本発明化合物の製造方法は既に周知の方法であ
り、例えば、以下の方法により製造することがで
きる。
(1)ラクタムと酸無水物の反応、(2)ラクタムと酸
クロリドの直接反応、(3)３級アミン類あるいはジ
メチルホルムアミド存在下でのラクタムと酸塩化
物との反応、(4)ラクタムのアルカリ金属塩と酸塩
化物との反応、(5)ラクチムエーテルと酸塩化物と
の反応、(6)トリメチルシリル化ラクタムを経由し
た酸クロリドとの反応、(7)２−クロロピリジニウ
ム塩による酸との中間体とラクタムとの反応など
により容易に製造することができる。
例えば、ラクタムと酸クロリドとの直接反応法
で製造する方法について云えば、フエニル酢酸、
フエニルプロピオン酸、桂皮酸を塩化チオニル、
五塩化リン、三塩化リン、塩化オキサリル等で、
酸クロリド化した後、２−ピロリドン、２−ピペ
リドン、ε−カプロラクタムと反応させることに
より、それぞれ前記一般式中に於けるＲが−CH2
−、−CH2−CH2、−CH2＝CH2−のＮ−アシルラ
クタム類化合物を容易に製造することができる。
本発明促進剤は、一般にはメタン醗酵槽に添加
するが、メタン醗酵原料の有機物に添加しても良
いし、醗酵中の槽に単味で添加してもよい。
促進剤の添加形態としては、液状であつても粉
末状であつてもよく、その使用割合は特段限定さ
れないが、有機物100重量部に対して0.01〜0.1重
量部が好ましい。
以下に本発明を実施例により更に説明する。
製造例
３−フエニルプロピオン酸１ｇに塩化チオニル
３ｇを加え５時間80℃に保持し、減圧下で発生ガ
ス及び残存塩化チオニルを除去する。
この反応物に、５mlの無水ピリジンに２−ピペ
リドン0.7ｇを溶解した液を添加し、５時間80〜
90℃に保持し、反応混合物にエーテルを加えて、
有機溶媒層を分取し、これを1N塩酸溶液、1N水
酸化ナトリウム溶液、水で順次洗浄し、芒硝で脱
水後溶媒を留去する。残渣を酢酸エチル、ｎ−ヘ
キサンの混合溶媒に溶解後結晶化を行ない１−
（３−フエニルプロパノイル）−２−ピペリドン
1.86ｇを得た。
また上記と同様の方法により、下表に示すメタ
ン醗酵促進剤を製造した。以下にその物質名及び
以後使用する試料記号を記載する。
The present invention relates to a methane fermentation promoter. Since oil shock, methane fermentation has been attracting attention as a method for purifying waste such as agricultural and livestock waste, forest product waste, and dietary waste, as well as recovering it as a thermal energy source. In particular, with the spread of human waste and sewage treatment facilities, anaerobic digestion methods have been developed that enable high concentration treatment and have the advantage of generating less sludge. It has drawbacks such as requiring heating and a long digestion period. For example, in an anaerobic digestion test, it took 90 days for 90% gasification to occur at 10°C, and 28 days at 30°C.
per day and per gram of sludge, the amount of gas generated is 10℃
Compared to 450 ml, 760 ml is extremely temperature dependent at 30°C, so in actual operation it is carried out at 30 to 40°C, and it usually takes 20 to 30 days to digest. In view of this current situation, we conducted various studies on methods to increase the gasification rate and increase the amount of methane gas generated not only at room temperature but also at low temperatures, and as a result, we completed the present invention as detailed below. This is what I did. That is, the present invention has the general formula (However, R represents -CH2- , -CH2 -CH2- , or -CH=CH-, and n=3 to 5) A methane fermentation promoter consisting of an N-acyllactam compound Regarding. The compound of the present invention can be produced by a well-known method, for example, by the following method. (1) Reaction of lactam with acid anhydride, (2) Direct reaction of lactam with acid chloride, (3) Reaction of lactam with acid chloride in the presence of tertiary amines or dimethylformamide, (4) Reaction of lactam with acid chloride, (4) Reaction of lactam with acid chloride in the presence of tertiary amines or dimethylformamide, Reaction of alkali metal salts with acid chlorides, (5) Reaction of lactim ether with acid chlorides, (6) Reaction with acid chlorides via trimethylsilylated lactams, (7) Acid reactions with 2-chloropyridinium salts. It can be easily produced by reacting an intermediate with a lactam. For example, regarding the production method using the direct reaction method of lactam and acid chloride, phenyl acetic acid,
Phenylpropionic acid, cinnamic acid, thionyl chloride,
Phosphorus pentachloride, phosphorus trichloride, oxalyl chloride, etc.
After acid chloridation, by reacting with 2-pyrrolidone, 2-piperidone, and ε-caprolactam, each R in the above general formula is converted to -CH 2
-, -CH2 - CH2 , -CH2 = CH2- N-acyllactam compounds can be easily produced. The accelerator of the present invention is generally added to a methane fermentation tank, but it may also be added to the organic matter of the raw material for methane fermentation, or it may be added alone to the tank during fermentation. The accelerator may be added in a liquid or powder form, and its usage ratio is not particularly limited, but is preferably 0.01 to 0.1 parts by weight per 100 parts by weight of the organic substance. The present invention will be further explained below with reference to Examples. Production Example 3 g of thionyl chloride was added to 1 g of 3-phenylpropionic acid, kept at 80°C for 5 hours, and the generated gas and residual thionyl chloride were removed under reduced pressure. A solution of 0.7 g of 2-piperidone in 5 ml of anhydrous pyridine was added to this reaction mixture for 5 hours.
Hold at 90 °C and add ether to the reaction mixture.
Separate the organic solvent layer, wash it sequentially with 1N hydrochloric acid solution, 1N sodium hydroxide solution, and water, dehydrate with sodium sulfate, and then evaporate the solvent. The residue was dissolved in a mixed solvent of ethyl acetate and n-hexane and crystallized to give 1-
(3-phenylpropanoyl)-2-piperidone
1.86g was obtained. In addition, methane fermentation promoters shown in the table below were produced by the same method as above. The name of the substance and the sample symbol used hereinafter are listed below.
【表】【table】
【表】
実施例 １
第１表に示すメタン菌培地において消化スラツ
ジ（し尿処理場）を約２ケ月間にわたり馴養後植
種用液とした。第３表に示した物質１mgを１mlの
メタノールに溶解後、10μをセプタム付きスク
リユーバイアルビン（５ml）に添加し、減圧でメ
タノールを除去後、第２表に示す減菌済み試験用
培地１に前記植種用液を20ml添加し、バイアル
ビンに５mlづつ分注し、30℃で培養を行なつた。
本試験はすべて嫌気培養器（タバイ）で行なつ
た。
ヘツドスペースガス中のメタン濃度の変化をガ
スクロマトグラフで測定した結果を第３表に示し
た。[Table] Example 1 Digested sludge (human waste treatment plant) was acclimatized for about 2 months in the methane bacteria culture medium shown in Table 1, and then used as a seeding solution. Dissolve 1 mg of the substances shown in Table 3 in 1 ml of methanol, add 10μ to a screw vial with a septum (5 ml), remove methanol under reduced pressure, and sterilize the test medium 1 shown in Table 2. 20 ml of the above-mentioned inoculation solution was added to the solution, and 5 ml each was dispensed into vials and cultured at 30°C.
All tests were conducted in an anaerobic incubator (Tabai). Table 3 shows the results of measuring changes in methane concentration in the headspace gas using a gas chromatograph.
【表】【table】
【表】【table】
【表】
※ 第１表と同組成
[Table] * Same composition as Table 1
【表】
実施例 ２
し尿処理場嫌気醗酵汚泥を種汚泥とし、第４表
に示す〜の原水に対する醗酵試験を行なつ
た。初発有機物負荷10Kg／m2で行ない、無撹拌で
30℃に保つた。試料添加量を１mg／．回として
開始時、５日目、15日目に添加した。結果を第５
表に示す。[Table] Example 2 Using anaerobic fermentation sludge from a human waste treatment plant as seed sludge, a fermentation test was conducted on raw water shown in Table 4. Performed at an initial organic load of 10Kg/ m2 , without stirring.
It was kept at 30℃. The amount of sample added was 1 mg/. It was added at the beginning, on the 5th day, and on the 15th day. 5th result
Shown in the table.
【表】【table】
【表】【table】
【表】
無添加時発生量
実施例 ３
実施例２と同じ試験を原水．に対し継続撹
拌下30℃で行つた。その結果を第６、７表に示
す。第６表は原水に対する効果、第７表は原水
に対する効果である。[Table] Example 3 of amount generated without additives The same test as in Example 2 was conducted using raw water. The test was carried out at 30°C under continuous stirring. The results are shown in Tables 6 and 7. Table 6 shows the effect on raw water, and Table 7 shows the effect on raw water.
【表】
活性度＊：第５表参照
[Table] Activity * : See Table 5
【表】
活性度＊：第５表参照
実施例 ４
実施例２と同じ試験を20℃で行つた。結果を第
８表及び第９表に示す。第８表は原水に対する
効果、第９表は原水に対する効果である。[Table] Activity * : See Table 5 Example 4 The same test as in Example 2 was conducted at 20°C. The results are shown in Tables 8 and 9. Table 8 shows the effect on raw water, and Table 9 shows the effect on raw water.
【表】【table】
Claims (1)
CH＝CH−を示し、ｎ＝３〜５である）で示さ
れるＮ−アシルラクタム類化合物からなるメタン
醗酵促進剤。[Claims] 1. General formula (However, R is -CH 2 -, -CH 2 -CH 2 - or -
A methane fermentation promoter comprising an N-acyllactam compound represented by CH=CH- and n=3 to 5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60071622A JPS61230798A (en) | 1985-04-03 | 1985-04-03 | Methane fermentation promotor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60071622A JPS61230798A (en) | 1985-04-03 | 1985-04-03 | Methane fermentation promotor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61230798A JPS61230798A (en) | 1986-10-15 |
| JPH0228397B2 true JPH0228397B2 (en) | 1990-06-22 |
Family
ID=13465932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60071622A Granted JPS61230798A (en) | 1985-04-03 | 1985-04-03 | Methane fermentation promotor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61230798A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0647120B2 (en) * | 1988-03-07 | 1994-06-22 | 新技術事業団 | Fast methane fermentation method |
| CA2165919A1 (en) | 1994-12-26 | 1996-06-27 | Koichi Katsuyama | Agents for inhibiting the production of il-1.beta. and the release of tnf. |
-
1985
- 1985-04-03 JP JP60071622A patent/JPS61230798A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61230798A (en) | 1986-10-15 |
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