CN112661684A - Method for synthesizing long-chain alkyl coenzyme M - Google Patents
Method for synthesizing long-chain alkyl coenzyme M Download PDFInfo
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- CN112661684A CN112661684A CN202011510552.9A CN202011510552A CN112661684A CN 112661684 A CN112661684 A CN 112661684A CN 202011510552 A CN202011510552 A CN 202011510552A CN 112661684 A CN112661684 A CN 112661684A
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Abstract
The invention discloses a synthesis method of long-chain alkyl coenzyme M, designs an artificial synthesis method of a standard substance of the long-chain alkyl coenzyme M, and can be applied to verification of the long-chain alkyl coenzyme M in a microbial sample. A method for synthesizing long-chain alkyl coenzyme M comprises the following steps: the mercapto sodium ethanesulfonate is subjected to iodination reaction with iodinated long-chain alkyl hydrocarbon to synthesize the long-chain alkyl coenzyme M.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of long-chain alkyl coenzyme M.
Background
Methane is the simplest and highest content of hydrocarbons on earth, and both methane and other alkanes can be used by microorganisms as energy and carbon sources. Under aerobic conditions, microorganisms activate alkanes using methane or alkane monooxygenase, which in turn produces methanol or other alcohols as primary intermediates. Under anaerobic conditions, the initial degradation mechanism known so far mainly consists of (1) the fumaric acid addition pathway, an addition reaction combining fumaric acid with aromatic hydrocarbons/alkanes by means of a phenyl/alkylsuccinic acid synthetase (Bss/Ass); (2) carboxylation, which utilizes carbon dioxide or bicarbonate to attack benzene or naphthalene and convert the benzene or naphthalene into benzoic acid or 2-carboxyl naphthalene; (3) hydroxylation, in which molybdenum enzyme attacks and benzene ring branched methylene in the ethylbenzene metabolism process to hydroxylate the benzene ring branched methylene; (4) hydration, water molecules attack unsaturated carbon-carbon bonds under the catalysis of hydratase to generate addition reaction; recently, there has been newly reported (5) a methyl-or alkyl-coenzyme reduction reaction in which a methyl-or alkyl-coenzyme M is formed by methyl-coenzyme M reductase (MCR), activating the reaction in which alkanes participate in anaerobic degradation.
In all anaerobic alkoxylated archaea described so far, the first step in alkane oxidation is the conversion of methane to methyl-coenzyme M by methyl-coenzyme M reductase MCR. In 2016, butyl coenzyme M, an important intermediate metabolite in the anaerobic butane oxidation process, was discovered for the first time by Laso-Perez and the like; in 2019, Chen et al found the presence of ethyl-coenzyme M in the ethane degradation system. They all demonstrated that the alkyl-coenzyme M reductase ACR can convert polycarboalkanes into alkyl-coenzyme M. For the degradation of long chain alkyl, long chain alkyl coenzyme M is a very important evidence as an intermediate metabolite.
Long chain alkyl hydrocarbons and their cyclic compounds are common in petroleum and refined petroleum products, and for complex microbial systems, the presence of long chain alkyl coenzyme M therein is proved to be qualitative work by comparison with artificially synthesized standards. In the prior art, Laso-Perez synthesizes butyl coenzyme M through bromination reaction, and Chen synthesizes ethyl coenzyme M through bromination reaction, and the ethyl coenzyme M can be used as standard substances to verify the existence of butyl coenzyme M and ethyl coenzyme M in a microbial system.
For longer-chain normal alkane coenzyme M, the synthesis cannot adopt bromination reaction through verification. The research of the long-chain alkyl hydrocarbon degradation metabolic pathway by artificially synthesizing the long-chain alkyl coenzyme M is a necessary condition, and the long-chain alkyl coenzyme M is very important for the relevant work of the subsequent metabolic pathway research. The research synthesizes long-chain alkyl coenzyme M, and can realize rapid, accurate and stable large-scale qualitative and quantitative work of various long-chain alkyl coenzyme M compounds in a complex sample by combining LC-MS/MS analysis.
Disclosure of Invention
The invention aims to provide a method for synthesizing long-chain alkyl coenzyme M, which is used for comparing and verifying the long-chain alkyl coenzyme M generated in the microbial metabolism process by artificially synthesizing a standard substance of the long-chain alkyl coenzyme M, thereby facilitating the research on the metabolic pathway of the long-chain alkyl coenzyme M.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a method for synthesizing long-chain alkyl coenzyme M comprises the following steps: the mercapto sodium ethanesulfonate generates long-chain alkyl coenzyme M through iodination reaction.
As a preferred technical scheme, the mercapto sodium ethanesulfonate is subjected to iodination reaction by iodinating long-chain alkyl hydrocarbon to synthesize the long-chain alkyl coenzyme M.
As a preferred technical scheme, the long-chain alkyl coenzyme M is long-chain alkyl mercapto sodium ethanesulfonate or long-chain alkyl mercapto sodium ethanesulfonate with a branched chain.
As a preferred technical scheme, the synthesis method is as follows: the mercapto sodium ethanesulfonate is put into a reaction vessel, ammonia water is added, 1-iodo long-chain alkane or 1-iodo long-chain alkyl with branched chain is added, and reaction is carried out.
As a preferred technical scheme, iodination is carried out, and the reaction temperature is 35-65 ℃. Below 35 ℃ no product can be obtained.
As a preferred technical scheme, the rotation speed of the iodination reaction is 200-400 rpm.
As a preferred technical scheme, the molar ratio of the sodium mercaptoethanesulfonate to the iodo-long-chain alkyl hydrocarbon is 1: 5-1: 10.
As a preferred technical scheme, the iodination reaction time is 10-16 h. Below 10h, the product obtained is insufficient.
The invention has the technical advantages that: the method for artificially synthesizing the long-chain alkyl coenzyme M standard substance is innovatively designed, and can be applied to the verification of the long-chain alkyl coenzyme M in a microorganism sample.
In the present invention, iodo is used to produce long-chain alkyl coenzyme M, which cannot be produced by bromo. The reason for the analysis is presumably as follows: the carbon atom substitution on the iodo long-chain alkyl hydrocarbon is less, so that the reaction is easy to generate nucleophilic reaction; the iodine ions have weaker proton accepting capability than the bromine ions, so the alkalinity is weak, and the nucleophilicity of the iodine ions is stronger; the final experimental result of bromination is that long-chain alkyl coenzyme M cannot be generated. The number of the distribution layers of peripheral electrons of the iodide ions and the bromide ions is different, the negative charge of the iodide ions is more, the electrons on the outer layer are more, the electron cloud radius is large, the change is easy, the bond length of the stroke is longer, the bond is easy to break, so that the substitution reaction is easy to occur, the radius is large after leaving, the negative charge is easy to deform and disperse, the ions are stabilized, and therefore, the leaving group is more stable, so that the iodide can generate long-chain alkyl coenzyme M, but the bromide cannot generate.
Drawings
FIG. 1(a) is a first-order mass spectrum of a synthetic standard n-hexadecane coenzyme M, whose M/z coincides with the theoretical value three positions after the decimal point; FIG. 1(b) shows the measured n-hexadecane coenzyme M in the microbial sample, which is consistent with the synthetic sample.
FIG. 2(a) is a second-order mass spectrum of a synthetic standard n-hexadecane coenzyme M, whose M/z coincides with the theoretical value three positions after the decimal point; FIG. 2(b) shows the fragment ions of n-hexadecane coenzyme M detected in the microbial sample, which is consistent with the synthetic sample.
FIG. 3(a) is a liquid phase chromatogram of a microbial sample with synthesized n-hexadecane coenzyme, the time to peak was completely consistent, and no n-hexadecane coenzyme was present in the solvent; FIG. 3(b) is an XIC pattern of a microbial sample and synthesized n-hexadecane coenzyme, the extracted fragment ion peak time was completely consistent, and n-hexadecane coenzyme was absent from the solvent.
Detailed Description
The present invention is intended to overcome the drawbacks of the prior art and to provide a method for synthesizing a long-chain alkyl coenzyme M, which will be described in further detail with reference to the following examples.
Example 1
A process for synthesizing long-chain alkyl coenzyme M is disclosed, which is the sodium n-hexadecyl mercaptoethanesulfonate or its sodium n-hexadecyl mercaptoethanesulfonate. The structural formula is as follows:
the synthetic route is as follows:
the synthetic process comprises the following steps: weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodohexadecane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
Example 2
A method for synthesizing long-chain alkyl coenzyme M is characterized in that the long-chain alkyl coenzyme M is sodium n-heptadeca-mercaptoethanesulfonate, and the specific synthesis method is as follows:
weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodoheptadecane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The reaction route is as follows:
example 3
A method for synthesizing long-chain alkyl coenzyme M is characterized in that the long-chain alkyl coenzyme M is n-octadecyl mercapto ethanesulfonic acid sodium salt, and the specific synthesis method is as follows:
weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodooctadecane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The synthetic route is as follows:
example 4
A method for synthesizing long-chain alkyl coenzyme M, wherein the long-chain alkyl coenzyme M is nonadecyl mercapto ethanesulfonic acid sodium salt, and the specific synthesis method is as follows:
weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodononadecane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The synthetic route is as follows:
example 5
A process for synthesizing long-chain alkyl coenzyme M is disclosed, which is the sodium n-eicosyl mercaptoethanesulfonate. The structural formula is as follows:
the synthetic route is as follows:
the synthetic process comprises the following steps: weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodoeicosane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
Example 6
A method for synthesizing long-chain alkyl coenzyme M is characterized in that the long-chain alkyl coenzyme M is n-heneicosane mercapto ethanesulfonic acid sodium salt, and the specific synthesis method is as follows:
weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodoheneicosane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The synthetic route is as follows:
example 7
A method for synthesizing long-chain alkyl coenzyme M is disclosed, the long-chain alkyl coenzyme M is sodium n-docosane mercapto ethanesulfonate, and the specific synthesis method is as follows:
weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iododocosane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The synthetic route is as follows:
example 8
A method for synthesizing long-chain alkyl coenzyme M is characterized in that the long-chain alkyl coenzyme M is sodium n-tridecyl mercaptoethanesulfonate, and the method for synthesizing the long-chain alkyl coenzyme M is as follows:
weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 μ L of 1-iodotridecane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The synthetic route is as follows:
example 9
A method for synthesizing long-chain alkyl coenzyme M, wherein the long-chain alkyl coenzyme M is n-tetradecyl mercaptoethanesulfonic acid sodium, and the specific synthesis method is as follows:
weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodotetradecane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The synthetic route is as follows:
example 10
A method for synthesizing long-chain alkyl coenzyme M, wherein the long-chain alkyl coenzyme M is n-pentadecane mercapto sodium ethanesulfonate, and the specific synthesis method is as follows:
weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodopentadecane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The synthetic route is as follows:
example 11
A method for synthesizing long-chain alkyl coenzyme M is characterized in that the long-chain alkyl coenzyme M is n-heneicosane mercapto ethanesulfonic acid sodium salt, and the specific synthesis method is as follows:
weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodoheneicosane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The synthetic route is as follows:
example 12
A method for synthesizing long-chain alkyl coenzyme M is disclosed, the long-chain alkyl coenzyme M is sodium n-docosane mercapto ethanesulfonate, and the specific synthesis method is as follows:
weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iododocosane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The synthetic route is as follows:
example 13
A method for synthesizing long-chain alkyl coenzyme M is characterized in that the long-chain alkyl coenzyme M is n-hexadecyl sodium benzomercaptoethanesulfonate, and the specific synthesis method is as follows:
weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodohexadecylbenzene, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The synthetic route is as follows:
example 14
A method for synthesizing long-chain alkyl coenzyme M is characterized in that the long-chain alkyl coenzyme M is n-hexadecyl cyclohexane mercapto sodium ethanesulfonate, and the specific synthesis method is as follows:
weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodohexadecylcyclohexane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The synthetic route is as follows:
example 15
A process for synthesizing long-chain alkyl coenzyme M is disclosed, which is the sodium n-hexadecyl mercaptoethanesulfonate or its sodium n-hexadecyl mercaptoethanesulfonate. The structural formula is as follows:
the synthetic route is as follows:
the synthetic process comprises the following steps: weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodohexadecane, sealing, and reacting at 35 ℃ and 200-400 rpm for 14 h.
Example 16
A process for synthesizing long-chain alkyl coenzyme M is disclosed, which is the sodium n-hexadecyl mercaptoethanesulfonate or its sodium n-hexadecyl mercaptoethanesulfonate. The structural formula is as follows:
the synthetic route is as follows:
the synthetic process comprises the following steps: weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodohexadecane, sealing, and reacting at 65 ℃ and 200-400 rpm for 14 h.
Comparative example 1
The sodium n-hexadecane mercaptoethanesulfonate was synthesized by the following method.
The synthetic process comprises the following steps: weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-iodohexadecane, sealing, and reacting at the normal temperature and the rotation speed of 200-400 rpm for 14 h.
The data could not be detected, which indicates that n-hexadecyl mercapto sodium ethanesulfonate was not generated, i.e., n-hexadecyl mercapto sodium ethanesulfonate could not be generated at room temperature.
Comparative example 2
The sodium n-hexadecane mercaptoethanesulfonate was synthesized by the following method.
The synthetic process comprises the following steps: weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-bromohexadecane, sealing, and reacting at the normal temperature and the rotating speed of 200-400 rpm for 14 h.
The data cannot be detected, which indicates that the n-hexadecyl mercapto sodium ethanesulfonate is not generated, namely, the long chain is synthesized according to a method for producing the short chain, and the long chain cannot be generated.
Comparative example 3
The sodium n-hexadecane mercaptoethanesulfonate was synthesized by the following method.
The synthetic process comprises the following steps: weighing 0.125g of sodium mercaptoethanesulfonate into a sealable test tube, adding 2mL of 30% ammonia water into a fume hood, adding 500 mu L of 1-bromohexadecane, sealing, and reacting at 55 ℃ and 200-400 rpm for 14 h.
The data can not be detected, which indicates that the n-hexadecyl mercapto sodium ethanesulfonate is not generated, namely, the bromination reaction is carried out, and the n-hexadecyl mercapto sodium ethanesulfonate cannot be generated.
The invention is well implemented in accordance with the above-described embodiments. It should be noted that, based on the above structural design, in order to solve the same technical problems, even if some insubstantial modifications or colorings are made on the present invention, the adopted technical solution is still the same as the present invention, and therefore, the technical solution should be within the protection scope of the present invention.
Claims (8)
1. The synthesis method of the long-chain alkyl coenzyme M is characterized by comprising the following steps: the mercapto sodium ethanesulfonate generates long-chain alkyl coenzyme M through iodination reaction.
2. The method of claim 1, wherein the long-chain alkyl coenzyme M is synthesized by iodinating long-chain alkyl hydrocarbon with sodium mercaptoethanesulfonate.
3. The method for synthesizing long-chain alkyl coenzyme M according to any one of claims 1 to 2, wherein the long-chain alkyl coenzyme M is long-chain alkyl mercapto sodium ethanesulfonate or long-chain alkyl mercapto sodium ethanesulfonate with a branched chain.
4. The method of claim 3, wherein the method comprises the steps of: the mercapto sodium ethanesulfonate is put into a reaction vessel, ammonia water is added, 1-iodo long-chain alkane or 1-iodo long-chain alkyl with branched chain is added, and reaction is carried out.
5. The method of claim 4, wherein the iodination is performed at a temperature of 35-65 ℃.
6. The method of claim 4, wherein the iodination reaction occurs at a speed of 200-400 rpm.
7. The method for synthesizing long-chain alkyl coenzyme M according to claim 2, wherein the molar ratio of the sodium mercaptoethanesulfonate to the iodo long-chain alkyl hydrocarbon is 1:5 to 1: 10.
8. The method for synthesizing long-chain alkyl coenzyme M according to claim 4, wherein the reaction time is 10-16 h.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE823447C (en) * | 1949-05-14 | 1951-12-03 | Henkel & Cie Gmbh | Process for the preparation of mercaptosulphonic acids or their salts which are optionally substituted on sulfur |
| BE842665A (en) * | 1976-06-08 | 1976-12-08 | PROCESS FOR THE PREPARATION OF THIALKANE ALKALINE SULPHONATES |
-
2020
- 2020-12-18 CN CN202011510552.9A patent/CN112661684A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE823447C (en) * | 1949-05-14 | 1951-12-03 | Henkel & Cie Gmbh | Process for the preparation of mercaptosulphonic acids or their salts which are optionally substituted on sulfur |
| BE842665A (en) * | 1976-06-08 | 1976-12-08 | PROCESS FOR THE PREPARATION OF THIALKANE ALKALINE SULPHONATES |
Non-Patent Citations (8)
| Title |
|---|
| C. M. DRAIN 等: "Reactivity of [l,4,7,10,13-Pentaazacyclohexadecane-14,16-dionato(2-)]nickel(II) toward Derivatives of Methyl-Coenzyme M", 《INORG. CHEM.》 * |
| CHEN, SONG-CAN 等: "Anaerobic oxidation of ethane by archaea from a marine hydrocarbon seep", 《NATURE》 * |
| INAMI, AKIRA 等: "Effects of pH on the surface tension of the aqueous solutions of ampholytic surface-active agents", 《OSAKA-FURITSU KOGYO SHOREIKAN HOKOKU》 * |
| LASO-PEREZ, RAFAEL 等: "Thermophilic archaea activate butane via alkyl-coenzyme M formation", 《NATURE》 * |
| REPPE, WALTER 等: "Vinylation. II. Sulfur-containing vinyl compounds", 《JUSTUS LIEBIGS ANNALEN DER CHEMIE》 * |
| 尹小波 等: "辅酶M、甲基辅酶M和辅酶M氧化物的合成研究", 《中国沼气》 * |
| 王志江 等: "《无机化学》", 31 August 2020 * |
| 邢其毅 等: "《基础有机化学 上》", 30 November 1993 * |
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Application publication date: 20210416 |