JPS63141936A - Direct conversion of methane into formaldehyde, formic acid and methanol by photochemical reaction - Google Patents
Direct conversion of methane into formaldehyde, formic acid and methanol by photochemical reactionInfo
- Publication number
- JPS63141936A JPS63141936A JP28994686A JP28994686A JPS63141936A JP S63141936 A JPS63141936 A JP S63141936A JP 28994686 A JP28994686 A JP 28994686A JP 28994686 A JP28994686 A JP 28994686A JP S63141936 A JPS63141936 A JP S63141936A
- Authority
- JP
- Japan
- Prior art keywords
- methanol
- formic acid
- methane
- formaldehyde
- oxygen
- 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.)
- Pending
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 45
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 title claims abstract description 28
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims abstract description 24
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 235000019253 formic acid Nutrition 0.000 title claims abstract description 14
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 title claims abstract description 9
- 238000006552 photochemical reaction Methods 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 title description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000047 product Substances 0.000 abstract description 8
- 239000007789 gas Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052753 mercury Inorganic materials 0.000 abstract description 2
- 238000007599 discharging Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- BHGADZKHWXCHKX-UHFFFAOYSA-N methane;potassium Chemical compound C.[K] BHGADZKHWXCHKX-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
- B01J19/123—Ultraviolet light
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（【７）従来の技術
応させるものである。ギ酸の合成はメタノールを空気と
混合し、白金触媒を用いて行なわれている。また、メタ
ノールは一酸化炭素と水素の混合ガスを３００〜４００
’Ｃ，２５０〜３００気圧で父上１）させて合成してい
る。ポル１１アルデヒドとギ酸の合成はい４゛れもメタ
ノールを出発原料としている。DETAILED DESCRIPTION OF THE INVENTION ([7] This corresponds to the conventional technology. Formic acid is synthesized by mixing methanol with air and using a platinum catalyst. In addition, methanol is a mixed gas of carbon monoxide and hydrogen at 300 to 400
'C, 250 to 300 atmospheres, Father 1) is synthesized. The synthesis of pol-11 aldehyde and formic acid both uses methanol as a starting material.
（ハ）発明が解決しようとする問題点
用（１行なわれているホルムアルデヒド、ギ酸、メタノ
ールの合成は数段の工程を経て行なわれているものであ
り、しかも条件は高温、高圧で１＞る、メタノール合成
のために・ピ・要な−６（化炭素と水素はメタンとｌＫ
蒸気からｊｊ）るＪｊ法が効０気圧、酸化５１４−酸化
；ＢＨＩＨＨ糸の触媒を必要とする。ポルノ、アルデヒ
ドとギ酸の合成のためためにはさらにらう一段の１、稈
を経る必要がある。このような合成法はエイ・ルギー消
費、丁場＼γ地条件、操業コストの点から今後の発展は
望めない。しかるに、石ｔ１１１の涸渇がＩｌ１題とな
る２０〜３０年後において、食料や燃↑１の確保のため
に安価なホルムアルデヒド、ギ酸、メタノールの（ｊｌ
Ｈ給が不可欠で、’Ｐ＋る。(c) For problems to be solved by the invention (1) The synthesis of formaldehyde, formic acid, and methanol is carried out through several steps, and the conditions are high temperature and high pressure. , for the synthesis of methanol, P is necessary -6 (carbon and hydrogen are methane and lK
The Jj method from steam is effective, requires a catalyst of 0 atmospheres, oxidation 514-oxidation; BHIHH yarn. For the synthesis of porn, aldehydes and formic acid, it is necessary to pass through one more stage, the culm. This type of synthesis method cannot be expected to develop in the future due to energy consumption, soil conditions, and operating costs. However, in 20 to 30 years, when the depletion of stone t111 becomes a problem, cheap formaldehyde, formic acid, and methanol (jl1) will be used to secure food and fuel.
H pay is essential, 'P+ru.
（ニ）問題点と解決するための「「ｑ
本発明はこの欠点と除いて、ホルムアルデヒド、ギ酸、
メタノールを掌性にＪｊいてメタンカリｌ、 １１′Ｉ
接合成するものである。メタンは天然ガスとして１Ｆ界
中にぴ富に（ｆ“在している。メタンのイ１−効な利用
性が確立していない４：めにその人：１ニーを廃棄して
いる所すらある０本発明はメタンと水蒸気および空気ま
たは酸素から光化学反応を利用し′（ポルムアルテヒド
２ギ酸、メタノールを直接合成することに成功したムの
で。(d) To solve the problems, the present invention solves the problems by eliminating formaldehyde, formic acid,
The handedness of methanol is Jj, which is methane potassium l, 11'I.
It is used for bonding. Methane exists in the 1F world as natural gas.The effective use of methane has not been established. The present invention has succeeded in directly synthesizing polyalthehyde diformic acid and methanol from methane, water vapor, and air or oxygen using a photochemical reaction.
エネルギー１１“ｉ費が少なく、無触媒反応で、Ｐ）す
、公害物質を排出しないという１１ｒ色をもつものであ
る。It has low energy consumption, non-catalytic reaction, and does not emit any pollutants.
（ホ） （’ｒ：川と実施例
次に、本発明の実施方法とその生成物について実験結果
を例にあげて説明する。(e) ('r: River and Examples Next, the method of carrying out the present invention and its products will be explained using experimental results as examples.
第−例
実施（ＩＡｌは１気圧、９０′Ｃにおいて、メタンと水
蒸気Ｂよび酸にの混合ガスに光を照射して１′）られな
生成物（ｍｉｏｌ）結果である。This is the result of a product (miol) obtained by irradiating a mixed gas of methane, water vapor B, and an acid with light at 90'C and 1 atmosphere of the 1st Example.
実施例１
反応ガス中に占める酸素の％
１７．３ ２３．２ ２９．０ ３５．１ ４７，６ポ
ルムアルデヒド ９．６０ １６．７０ １Ｂ、５０
１９．２５ １６．１１ギ酸 １４ｊ５
１９．４３ ２５．４４ ２２．３６ ２１．９４メタ
ノール １６．７６ １８．７８ １８．１Ｂ
１５．２４ １４．０３過酸化水素 １０．２６
２１．１２ ２６．０ ．２８，１ ２６．９水素
３３．５１ ２１．９２ １０．４６ ８，
６５ ７．９３（ｍｍｏｌ）
実施例１における条件は次の通りである反応槽 液相部
３ｄｍＪ
気相部 １２ｄｍａ
液相の温次 ９（］’Ｃ
光源 １００Ｗ−低圧水銀ランプ
メタンの流速 ＋（Ｉ１１３／分
反応時間 ３時間
反応生成物としてはこのほかにもｅＭのエタノール、ケ
トン、エステルがある。また、水の光分解によって生じ
る水素と過酸化水素も（を在する、メタンがらの生成物
としてはホルムアルデヒド、ギ酸、メタノールが９０％
以上である。ホルムアルデヒド、メタノール、ギ酸の生
成はほぼ等量である。こ〕Ｅｉ１７（７）沸点ｇｉソｔ
Ｌソｈ １９．３’Ｃ、６７１，５′ｃ、１００．
ｌ’ｌｔ’ ト大キ＜異なるので生成物の分＾「は容易
である。Example 1 % of oxygen in reaction gas 17.3 23.2 29.0 35.1 47,6 Polmaldehyde 9.60 16.70 1B, 50
19.25 16.11 Formic acid 14j5
19.43 25.44 22.36 21.94 Methanol 16.76 18.78 18.1B
15.24 14.03 Hydrogen peroxide 10.26
21.12 26.0. 28,1 26.9 hydrogen
33.51 21.92 10.46 8,
65 7.93 (mmol) The conditions in Example 1 are as follows: Reaction tank Liquid phase: 3 dmJ Gas phase: 12 dma Temperature of liquid phase: 9 (]'C Light source: 100 W - low pressure mercury lamp Methane flow rate + (I113 /min Reaction time: 3 hours Other reaction products include eM ethanol, ketones, and esters.Hydrogen and hydrogen peroxide produced by photolysis of water are also produced as methane-like products. is 90% formaldehyde, formic acid, and methanol.
That's all. Formaldehyde, methanol, and formic acid are produced in approximately equal amounts. [This] Ei17 (7) boiling point gi sot
L soh 19.3'C, 671,5'c, 100.
l'lt' It is easy to divide the product because it is different.
第二例
実施例２は酸素の存在率２８尤のときの各反応時間にお
ける生成物の結果である。Second Example Example 2 shows the results of products at each reaction time when the oxygen abundance rate was 28%.
実施ＰＡ２
反応時間
１時間 ２時間 ４時間
ホルムアルデヒド ６．１７ ２０．１９
２２．３７ギ酸 ６．２０
２２．２７ ２８．５６（ｒｒｌｍｏｌ）
実施例２の反応条件は実施例１と同じである。生成物は
反応時間とともに増大している０反応時間４時間におい
て水素が急増しているのは酸素不足によるものである。Implementation PA2 Reaction time 1 hour 2 hours 4 hours Formaldehyde 6.17 20.19
22.37 Formic acid 6.20
22.27 28.56 (rrlmol) The reaction conditions of Example 2 are the same as Example 1. The product increases with the reaction time.The rapid increase in hydrogen at 0 reaction time of 4 hours is due to lack of oxygen.
いずれにしろ、反応生成物は時間とともに増大し、メタ
ンの転換率は５０％以上に達する。In any case, the reaction products increase with time, and the methane conversion rate reaches more than 50%.
（へ）発明の効果(f) Effect of invention
Claims (1)
空気からホルムアルデヒド、ギ酸およびメタノールの直
接合成法。Direct synthesis of formaldehyde, formic acid, and methanol from methane, water vapor, and oxygen or air using photochemical reactions.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28994686A JPS63141936A (en) | 1986-12-04 | 1986-12-04 | Direct conversion of methane into formaldehyde, formic acid and methanol by photochemical reaction |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28994686A JPS63141936A (en) | 1986-12-04 | 1986-12-04 | Direct conversion of methane into formaldehyde, formic acid and methanol by photochemical reaction |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63141936A true JPS63141936A (en) | 1988-06-14 |
Family
ID=17749782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28994686A Pending JPS63141936A (en) | 1986-12-04 | 1986-12-04 | Direct conversion of methane into formaldehyde, formic acid and methanol by photochemical reaction |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63141936A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020002119A (en) * | 2017-12-16 | 2020-01-09 | 国立大学法人大阪大学 | Manufacturing method of oxidation reaction product of hydrocarbon or derivative thereof |
-
1986
- 1986-12-04 JP JP28994686A patent/JPS63141936A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020002119A (en) * | 2017-12-16 | 2020-01-09 | 国立大学法人大阪大学 | Manufacturing method of oxidation reaction product of hydrocarbon or derivative thereof |
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